dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d25aea702e9447dabf441251e5cc1cd6 | CC(C)(C)OC(=O)N1CCC(C=O)CC1.CSc1ccc(Br)s1>>CSc1ccc(C(O)C2CCN(C(=O)OC(C)(C)C)CC2)s1 | C(CCC)[Li].[Cl-].[NH4+].C(=O)C1CCN(CC1)C(=O)OC(C)(C)C.BrC=1SC(=CC1)SC>>OC(C1CCN(CC1)C(=O)OC(C)(C)C)C=1SC(=CC1)SC | [CH:7](=[O:8])[CH:9]1[CH2:10][CH2:11][N:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:20][CH2:21]1.Br[c:6]1[cH:5][cH:4][c:3]([S:2][CH3:1])[s:22]1>>[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([OH:8])[CH:9]2[CH2:10][CH2:11][N:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:20][CH2:21]2)... | CC(C)(C)OC(=O)N1CCC(C=O)CC1.CSc1ccc(Br)s1 | CSc1ccc(C(O)C2CCN(C(=O)OC(C)(C)C)CC2)s1 | null | null | O1CCCC1.CCCCCC.O | C-C Coupling | Grignard_alcohol | 0ff768a6f231e6dfabb774fd9a3011bcb9799ec2dfd02b8c4b5457c7896d7f05 | 1c0bd0afc1d5e370e3c8193faf738f03752295e40fa0eb99c756011e9a4be26b | c1csc(CC2CCNCC2)c1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[c:5]:1.[C:6]-[C:7](-[CH;D2;+0:8]=[O;H0;D1;+0:9])-[C:10]>>[C:6]-[C:7](-[CH;D3;+0:8](-[OH;D1;+0:9])-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[c:5]:1)-[C:10] | 73 | [{"value": 73.0, "product": "OC(C1CCN(CC1)C(=O)OC(C)(C)C)C=1SC(=CC1)SC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | 1.2 g of 2-bromo-5-(methylsulfanyl)thiophen (compound in Production Example 45) was dissolved in 20 mL anhydrous tetrahydrofuran, and 3.72 mL solution of 1.59 M n-butyl lithium in hexane was added dropwise there to at −70° C. After the mixture was stirred for 1 hour, 6 ml solution of 1.2 g t-butyl 4-formyl-piperidine-1... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aldehyde | Secondary alcohol | c1ccsc1 | c1ccsc1 | c1ccsc1.C1CC[NH]CC1 | Br- | O1CCCC1.CCCCCC.O | 0 | 1 | CC(C)(C)OC(=O)N1CCC(C=O)CC1.CSc1ccc(Br)s1>O1CCCC1.CCCCCC.O>CSc1ccc(C(O)C2CCN(C(=O)OC(C)(C)C)CC2)s1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d751c0626a6448e78cef8dabd2d464de | CSc1ccc(C(O)C2CCN(C(=O)OC(C)(C)C)CC2)s1>>CSc1ccc(C(=O)C2CCN(C(=O)OC(C)(C)C)CC2)s1 | OC(C1CCN(CC1)C(=O)OC(C)(C)C)C=1SC(=CC1)SC>>CSC1=CC=C(S1)C(=O)C1CCN(CC1)C(=O)OC(C)(C)C | [CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([OH:8])[CH:9]2[CH2:10][CH2:11][N:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:20][CH2:21]2)[s:22]1>>[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[CH:9]2[CH2:10][CH2:11][N:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:20][CH2:21]2)[s:2... | CSc1ccc(C(O)C2CCN(C(=O)OC(C)(C)C)CC2)s1 | CSc1ccc(C(=O)C2CCN(C(=O)OC(C)(C)C)CC2)s1 | null | [O-2].[O-2].[Mn+4] | CC(=O)C | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C(c1cccs1)C1CCNCC1 | [C:1]-[C:2](-[CH;D3;+0:3](-[OH;D1;+0:4])-[c:5](:[c:6]):[#16;a:7]:[c:8])-[C:9]>>[C:1]-[C:2](-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[c:5](:[c:6]):[#16;a:7]:[c:8])-[C:9] | 81.3 | [{"value": 81.3, "product": "CSC1=CC=C(S1)C(=O)C1CCN(CC1)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | 1.41 g of t-butyl 4-[hydroxy-(5-methylsulfanylthiophen-2-yl)-methyl]-piperidine-1-carboxylate (compound in Production Example 389) was dissolved in 40 mL acetone, and 14 g manganese dioxide was added thereto and stirred at room temperature for 24 hours. The reaction mixture was filtered through Celite, then the solvent... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | c1ccsc1.C1CC[NH]CC1 | null | [O-2].[O-2].[Mn+4].CC(=O)C | null | 24 | CSc1ccc(C(O)C2CCN(C(=O)OC(C)(C)C)CC2)s1>[O-2].[O-2].[Mn+4].CC(=O)C>CSc1ccc(C(=O)C2CCN(C(=O)OC(C)(C)C)CC2)s1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e61ef03a6a7048389b3fabfde9a97bb5 | ClCCCBr.Sc1cccs1>>ClCCCSc1cccs1 | BrCCCCl.S1C(=CC=C1)S.C([O-])([O-])=O.[K+].[K+].CN(C=O)C>>ClCCCSC=1SC=CC1 | Br[CH2:4][CH2:3][CH2:2][Cl:1].[SH:5][c:6]1[cH:7][cH:8][cH:9][s:10]1>>[Cl:1][CH2:2][CH2:3][CH2:4][S:5][c:6]1[cH:7][cH:8][cH:9][s:10]1 | ClCCCBr.Sc1cccs1 | ClCCCSc1cccs1 | null | null | O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 26df88c6a3f5f203c89584658be4e126cb42994c98a2e16bc812e1036cdae857 | 8b2f52296c3a93039174c980b6042ba15754e04d6892a1284c3a32985220b214 | c1ccsc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[SH;D1;+0:4]-[c:5](:[c:6]):[#16;a:7]:[c:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:4]-[c:5](:[c:6]):[#16;a:7]:[c:8] | null | [] | null | null | 2 | HOUR | 2.7 mL 1-bromo-3-chloropropane was added to a mixture of 2 mL thiophen-2-thiol, 5.86 g potassium carbonate and 40 mL N,N-dimethylformamide under ice-cooling and then stirred at room temperature for 2 hours. Ethyl acetate and water were added to the reaction solution, and the organic layer was separated, washed with wat... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic thiol | Monosulfide | null | null | c1ccsc1 | HBr | O.C(C)(=O)OCC | null | 2 | ClCCCBr.Sc1cccs1>O.C(C)(=O)OCC>ClCCCSc1cccs1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b96e73a1e56e4329afd9d3fefcac5524 | COC(=O)c1ncnc2ccc(Br)cc12.NN>>NNC(=O)c1ncnc2ccc(Br)cc12 | BrC=1C=C2C(=NC=NC2=CC1)C(=O)OC.O.NN>>BrC=1C=C2C(=NC=NC2=CC1)C(=O)NN | CO[C:3](=[O:4])[c:5]1[n:6][cH:7][n:8][c:9]2[cH:10][cH:11][c:12]([Br:13])[cH:14][c:15]12.[NH2:1][NH2:2]>>[NH2:1][NH:2][C:3](=[O:4])[c:5]1[n:6][cH:7][n:8][c:9]2[cH:10][cH:11][c:12]([Br:13])[cH:14][c:15]12 | COC(=O)c1ncnc2ccc(Br)cc12.NN | NNC(=O)c1ncnc2ccc(Br)cc12 | null | null | CO | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | c1ccc2ncncc2c1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1.[N;D1;H2:9]-[NH2;D1;+0:10]>>[N;D1;H2:9]-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1 | null | [] | null | null | 30 | MINUTE | A mixture of 961 mg methyl 6-bromoquinazoline-4-carboxylate (compound in Production Example 413), 0.9 mL hydrazine monohydrate and 70 mL methanol was stirred at room temperature for 30 minutes, and the precipitated crystals were collected by filtration. The filtrate was evaporated to give additional crystals. The title... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | c1ccc2ncncc2c1 | HO- | CO | null | 0.5 | COC(=O)c1ncnc2ccc(Br)cc12.NN>CO>NNC(=O)c1ncnc2ccc(Br)cc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fc0e7eb3edef41c09384c426ffb901b6 | NNC(=O)c1ncnc2ccc(Br)cc12.O=C(Cl)C1CC1>>Brc1ccc2ncnc(-c3nnc(C4CC4)o3)c2c1 | C1(CC1)C(=O)Cl.BrC=1C=C2C(=NC=NC2=CC1)C(=O)NN.C([O-])(O)=O.[Na+].C([O-])(O)=O.[Na+].C([O-])(O)=O.[Na+].FC(S(=O)(=O)OS(=O)(=O)C(F)(F)F)(F)F.C([O-])(O)=O.[Na+].C1(CC1)C(=O)Cl>>BrC=1C=C2C(=NC=NC2=CC1)C=1OC(=NN1)C1CC1 | [Br:1][c:2]1[cH:3][cH:4][c:5]2[n:6][cH:7][n:8][c:9]([C:10]([NH:11][NH2:12])=[O:17])[c:18]2[cH:19]1.O=[C:13](Cl)[CH:14]1[CH2:15][CH2:16]1>>[Br:1][c:2]1[cH:3][cH:4][c:5]2[n:6][cH:7][n:8][c:9](-[c:10]3[n:11][n:12][c:13]([CH:14]4[CH2:15][CH2:16]4)[o:17]3)[c:18]2[cH:19]1 | NNC(=O)c1ncnc2ccc(Br)cc12.O=C(Cl)C1CC1 | Brc1ccc2ncnc(-c3nnc(C4CC4)o3)c2c1 | null | null | O.ClCCl.C(C)(=O)OCC.N1=CC=CC=C1.O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | 7b22eb68ec5345f7f4cdc12268e6dd899694812e04be4ec0a8725f54e8c7e6aa | d63ffdf77bc32b2859f63e1bbc219ac80e6aac3351af5f8cc8edf61f1355bec5 | c1ccc2c(-c3nnc(C4CC4)o3)ncnc2c1 | Cl-[C;H0;D3;+0:1](=O)-[C:2]1-[C:3]-[C:4]-1.[NH2;D1;+0:5]-[NH;D2;+0:6]-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-[c;H0;D3;+0:9]1:[#7;a:10]:[c:11]:[#7;a:12]:[c:13](:[c:14]):[c:15]:1:[c:16]>>[c:16]:[c:15]1:[c:13](:[c:14]):[#7;a:12]:[c:11]:[#7;a:10]:[c;H0;D3;+0:9]:1-[c;H0;D3;+0:7]1:[n;H0;D2;+0:6]:[n;H0;D2;+0:5]:[c;H0;D3;+0:1](-[C:2]... | null | [] | null | null | 1 | HOUR | 0.4 mL cyclopropane carbonyl chloride was added to a mixture of 796 mg of 6-bromoquinazoline-4-carboxylic acid hydrazide (compound in Production Example 414), 380 mg sodium bicarbonate, 15 mL tetrahydrofuran and 15 mL water, and the mixture was stirred at room temperature for 1 hour. 130 mg sodium bicarbonate and 0.13 ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acylhydrazine | null | null | c1nnco1 | c1ccc2ncncc2c1.c1nnco1.C1CC1 | HCl | O.ClCCl.C(C)(=O)OCC.N1=CC=CC=C1.O1CCCC1 | null | 1 | NNC(=O)c1ncnc2ccc(Br)cc12.O=C(Cl)C1CC1>O.ClCCl.C(C)(=O)OCC.N1=CC=CC=C1.O1CCCC1>Brc1ccc2ncnc(-c3nnc(C4CC4)o3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-55df594452ee4740a10f16d5383c63b8 | NC1CC1.O=[N+]([O-])c1cccc(S(=O)(=O)Cl)c1>>Nc1cccc(S(=O)(=O)NC2CC2)c1 | [N+](=O)([O-])C=1C=C(C=CC1)S(=O)(=O)Cl.C1(CC1)N.O1CCCC1>>NC=1C=C(C=CC1)S(=O)(=O)NC1CC1 | [NH2:10][CH:11]1[CH2:12][CH2:13]1.O=[N+:1]([O-])[c:2]1[cH:3][cH:4][cH:5][c:6]([S:7](Cl)(=[O:8])=[O:9])[cH:14]1>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]([S:7](=[O:8])(=[O:9])[NH:10][CH:11]2[CH2:12][CH2:13]2)[cH:14]1 | NC1CC1.O=[N+]([O-])c1cccc(S(=O)(=O)Cl)c1 | Nc1cccc(S(=O)(=O)NC2CC2)c1 | null | null | O | Acylation | OtherReaction | 32e63a5c7250f494145cad2adf79ccc80d279700c6f7969f4ada2d999986b234 | 7303abf85651d19b55f8b79e7f4480561113e4a46119b4ce872616e21eb733a4 | O=S(=O)(NC1CC1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[c:7](-[N+;H0;D3:8](=O)-[O-]):[c:9].[NH2;D1;+0:10]-[C:11]1-[C:12]-[C:13]-1>>[NH2;D1;+0:8]-[c:7](:[c:9]):[c:6]:[c:4](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[NH;D2;+0:10]-[C:11]1-[C:12]-[C:13]-1):[c:5] | 78.3 | [{"value": 78.3, "product": "NC=1C=C(C=CC1)S(=O)(=O)NC1CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A mixture of 2.0 g 3-nitrobenzene sulfonyl chloride, 1.8 g cyclopropyl amine and 50 mL tetrahydrofuran was stirred for 30 minutes under ice-cooling. Water was added to the mixture which was then extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Primary amine.Sulfonyl halide | Sulfonamide.Primary amine | null | null | c1ccccc1.C1CC1 | Other | O | null | 0.5 | NC1CC1.O=[N+]([O-])c1cccc(S(=O)(=O)Cl)c1>O>Nc1cccc(S(=O)(=O)NC2CC2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-170f2caf988e4501a2abbd5de84e3884 | CC(C)(C)OC(=O)N1CCNCC1.COc1cccc(CCl)c1>>COc1cccc(CN2CCNCC2)c1 | COC=1C=C(CCl)C=CC1.C(=O)(OC(C)(C)C)N1CCNCC1.C(C)N(CC)CC>>COC=1C=C(CN2CCNCC2)C=CC1 | CC(C)(C)OC(=O)[N:9]1[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]1.Cl[CH2:8][c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:15]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][N:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]2)[cH:15]1 | CC(C)(C)OC(=O)N1CCNCC1.COc1cccc(CCl)c1 | COc1cccc(CN2CCNCC2)c1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | db6fe90819b01acc1d77ac8161baa790f936d0aa5f5bc8fa21ee086aa22fc16b | a8bb195a563e3d75cf4b5698f17ee0104c6036dda9c0d819e472675fa1d5becb | c1ccc(CN2CCNCC2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.Cl-[CH2;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[c:9]:[c:8](-[CH2;D2;+0:7]-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1):[c:10] | 91.1 | [{"value": 91.1, "product": "COC=1C=C(CN2CCNCC2)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | A mixture of 2.0 g 3-methoxy benzylchloride, 2.9 g 1-Boc piperazine, 5 mL triethylamine, and 20 mL tetrahydrofuran was stirred at room temperature for 20 minutes. The mixture was concentrated, and the residue was added to 20 mL trifluoroacetic acid and stirred at room temperature for 20 minutes. The trifluoroacetic aci... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbamic ester.Ether.Boc | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CCN1 | c1ccccc1.C1C[NH]CCN1 | HCl | O1CCCC1 | null | 0.333333 | CC(C)(C)OC(=O)N1CCNCC1.COc1cccc(CCl)c1>O1CCCC1>COc1cccc(CN2CCNCC2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-55b308ab717d4f438e10bc8c641a8222 | COCOc1ccc(Br)cc1F.CSC>>COCOc1ccc(SC)cc1F | [Cl-].[NH4+].C(CCC)[Li].BrC1=CC(=C(C=C1)OCOC)F.CSC>>FC1=C(C=CC(=C1)SC)OCOC | Br[c:8]1[cH:7][cH:6][c:5]([O:4][CH2:3][O:2][CH3:1])[c:12]([F:13])[cH:11]1.C[S:9][CH3:10]>>[CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([S:9][CH3:10])[cH:11][c:12]1[F:13] | COCOc1ccc(Br)cc1F.CSC | COCOc1ccc(SC)cc1F | null | null | O1CCCC1.O | Heteroatom Alkylation and Arylation | OtherReaction | 8c6dc51512ab28d4cb9441689ce7cb87249900712ea999d5c69c20b93d2b2353 | c58e6934d5c82ddec3b0774dc166fdbb9c9ad3acfbb76cde182cbe53c5c1e68c | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C-[S;H0;D2;+0:6]-[C;D1;H3:7]>>[C;D1;H3:7]-[S;H0;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | 0 | CELSIUS | 1 | HOUR | 5 g of 4-bromo-2-fluoro-1-methoxymethoxybenzene was dissolved in 50 mL anhydrous tetrahydrofuran, and 13.4 mL n-butyl lithium (1.59 M hexane solution) was added dropwise thereto at −70° C. After the mixture was stirred for 1 hour, 2.1 ml dimethyl sulfide was added dropwise thereto and stirred at −70° C. for 1 hour, and... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Monosulfide | Monosulfide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | O1CCCC1.O | 0 | 1 | COCOc1ccc(Br)cc1F.CSC>O1CCCC1.O>COCOc1ccc(SC)cc1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-50f4f6bd9881428ba5ec86cc61370138 | CC(C)(C)OC(=O)N1CCC(O)CC1.CSc1ccc(O)c(F)c1>>CSc1ccc(OC2CCN(C(=O)OC(C)(C)C)CC2)c(F)c1 | N(=NC(=O)OCC)C(=O)OCC.FC1=C(C=CC(=C1)SC)O.OC1CCN(CC1)C(=O)OC(C)(C)C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>FC1=C(OC2CCN(CC2)C(=O)OC(C)(C)C)C=CC(=C1)SC | O[CH:8]1[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]1.[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[c:21]([F:22])[cH:23]1>>[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH:8]2[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]2)[c:21... | CC(C)(C)OC(=O)N1CCC(O)CC1.CSc1ccc(O)c(F)c1 | CSc1ccc(OC2CCN(C(=O)OC(C)(C)C)CC2)c(F)c1 | null | null | O1CCCC1.O | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | a9e936b0e9135225700edbab1c7696738b7f1f0756494b6ceeeda63b184d572f | 776ba735002e33225fbc578943016110c2c43efefd97bfeea4ec3cc2e2e1532f | c1ccc(OC2CCNCC2)cc1 | O-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[c:9]:[c:8](-[O;H0;D2;+0:7]-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1):[c:10] | 64.9 | [{"value": 64.9, "product": "FC1=C(OC2CCN(CC2)C(=O)OC(C)(C)C)C=CC(=C1)SC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 1.01 g 2-fluoro-4-methylsulfanyl phenol (compound in Production Example D088), 1.28 g t-butyl 4-hydroxy-1-piperidinecarboxylate, 2.5 g triphenylphosphine and 4.2 g diethyl azodicarboxylate (40% toluene solution) in anhydrous tetrahydrofuran (30 mL) was heated for 8 hours under reflux in a stream of nitrog... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Aromatic alcohol | Ether | C1CC[NH]CC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1 | HO- | O1CCCC1.O | null | null | CC(C)(C)OC(=O)N1CCC(O)CC1.CSc1ccc(O)c(F)c1>O1CCCC1.O>CSc1ccc(OC2CCN(C(=O)OC(C)(C)C)CC2)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-974ff422334b47ba88b6df9ed7b633cf | CC(C)(C)OC(=O)N1CCC(O)CC1.Oc1ccc(SC(F)(F)F)cc1>>CC(C)(C)OC(=O)N1CCC(Oc2ccc(SC(F)(F)F)cc2)CC1 | FC(F)(F)SC1=CC=C(C=C1)O.OC1CCN(CC1)C(=O)OC(C)(C)C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.N(=NC(=O)OCC)C(=O)OCC>>FC(F)(F)SC1=CC=C(OC2CCN(CC2)C(=O)OC(C)(C)C)C=C1 | O[CH:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:25][CH2:24]1.[OH:12][c:13]1[cH:14][cH:15][c:16]([S:17][C:18]([F:19])([F:20])[F:21])[cH:22][cH:23]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([O:12][c:13]2[cH:14][cH:15][c:16]([S:17][C:18]([F:19])([F:2... | CC(C)(C)OC(=O)N1CCC(O)CC1.Oc1ccc(SC(F)(F)F)cc1 | CC(C)(C)OC(=O)N1CCC(Oc2ccc(SC(F)(F)F)cc2)CC1 | null | null | O1CCCC1.O | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | a9e936b0e9135225700edbab1c7696738b7f1f0756494b6ceeeda63b184d572f | 776ba735002e33225fbc578943016110c2c43efefd97bfeea4ec3cc2e2e1532f | c1ccc(OC2CCNCC2)cc1 | O-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[c:9]:[c:8](-[O;H0;D2;+0:7]-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1):[c:10] | 79.1 | [{"value": 79.1, "product": "FC(F)(F)SC1=CC=C(OC2CCN(CC2)C(=O)OC(C)(C)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2 g 4-trifluoromethylsulfanyl-phenol, 2.07 g t-butyl 4-hydroxy-1-piperidinecarboxylate, 3.2 g triphenyl phosphine and 5.4 g diethyl azodicarboxylate (40% toluene solution) in anhydrous tetrahydrofuran (40 mL) was heated for 24 hours under reflux in a stream of nitrogen. Water was added thereto, and the re... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Aromatic alcohol | Ether | C1CC[NH]CC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1 | HO- | O1CCCC1.O | null | null | CC(C)(C)OC(=O)N1CCC(O)CC1.Oc1ccc(SC(F)(F)F)cc1>O1CCCC1.O>CC(C)(C)OC(=O)N1CCC(Oc2ccc(SC(F)(F)F)cc2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7db1e17f438440e89fa606a0b0807925 | CC(C)(C)OC(=O)N1CCC(Oc2ccc(SC(F)(F)F)cc2)CC1.O>>CC(C)(C)OC(=O)N1CCC(Oc2ccc(S(=O)(=O)C(F)(F)F)cc2)CC1 | I(=O)(=O)(=O)[O-].[Na+].FC(F)(F)SC1=CC=C(OC2CCN(CC2)C(=O)OC(C)(C)C)C=C1.C([O-])(O)=O.[Na+].O>>FC(S(=O)(=O)C1=CC=C(OC2CCN(CC2)C(=O)OC(C)(C)C)C=C1)(F)F | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([O:12][c:13]2[cH:14][cH:15][c:16]([S:17][C:20]([F:21])([F:22])[F:23])[cH:24][cH:25]2)[CH2:26][CH2:27]1.[OH2:19]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([O:12][c:13]2[cH:14][cH:15][c:16]([S:17](=[O:18])(=[O... | CC(C)(C)OC(=O)N1CCC(Oc2ccc(SC(F)(F)F)cc2)CC1.O | CC(C)(C)OC(=O)N1CCC(Oc2ccc(S(=O)(=O)C(F)(F)F)cc2)CC1 | null | O.[Ru](Cl)(Cl)Cl | null | Oxidation | OtherReaction | 20dd6d48007b4fe7cd760226f21413eb5e71e6468db112596c2e7ea4858c8ac1 | 5cedc1bf0f43f21d78a249521ecfcec19fc5ac4895c41eed0e84f0c2618149fa | c1ccc(OC2CCNCC2)cc1 | [F;D1;H0:1]-[C:2](-[F;D1;H0:3])(-[F;D1;H0:4])-[S;H0;D2;+0:5]-[c:6](:[c:7]):[c:8].[OH2;D0;+0:9]>>[F;D1;H0:1]-[C:2](-[F;D1;H0:3])(-[F;D1;H0:4])-[S;H0;D4;+0:5](=[O;D1;H0:10])(=[O;H0;D1;+0:9])-[c:6](:[c:7]):[c:8] | null | [] | null | null | null | null | 2.55 g sodium periodate and 0.4 mg ruthenium (III) chloride hydrate were added to 60 mL solution mixture (carbon tetrachloride/acetonitrile/water=1:1:2) of 1.5 g t-butyl 4-(4-trifluoromethylsulfanyl-phenoxy)piperidine-1-carboxylate (compound in Production Example 454) with stirring under ice-cooling, and the mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfone | null | null | C1CC[NH]CC1.c1ccccc1 | null | O.[Ru](Cl)(Cl)Cl | null | null | CC(C)(C)OC(=O)N1CCC(Oc2ccc(SC(F)(F)F)cc2)CC1.O>O.[Ru](Cl)(Cl)Cl>CC(C)(C)OC(=O)N1CCC(Oc2ccc(S(=O)(=O)C(F)(F)F)cc2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7db04d89c66a42aab25295c376d9c7a8 | Nc1ccc(F)cc1.O=C(O)C1CCN(c2ccnc3ccc(Br)cc23)CC1>>O=C(Nc1ccc(F)cc1)C1CCN(c2ccnc3ccc(Br)cc23)CC1 | C(C)N(CC)CC.ClC(=O)OCC(C)C.BrC=1C=C2C(=CC=NC2=CC1)N1CCC(CC1)C(=O)O.FC1=CC=C(N)C=C1>>FC1=CC=C(C=C1)NC(=O)C1CCN(CC1)C1=CC=NC2=CC=C(C=C12)Br | [NH2:3][c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][cH:10]1.O[C:2](=[O:1])[CH:11]1[CH2:12][CH2:13][N:14]([c:15]2[cH:16][cH:17][n:18][c:19]3[cH:20][cH:21][c:22]([Br:23])[cH:24][c:25]23)[CH2:26][CH2:27]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][cH:10]1)[CH:11]1[CH2:12][CH2:13][N:14]([c:15]2[cH:16][cH:17][n:18][c:1... | Nc1ccc(F)cc1.O=C(O)C1CCN(c2ccnc3ccc(Br)cc23)CC1 | O=C(Nc1ccc(F)cc1)C1CCN(c2ccnc3ccc(Br)cc23)CC1 | null | null | O1CCCC1.O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)C1CCN(c2ccnc3ccccc23)CC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[C:5] | null | [] | null | null | null | null | 0.34 mL triethylamine and 0.13 mL isobutyl chloroformate were added to a solution of 50 mg 1-(6-bromo-4-quinolyl)-4-piperidinecarboxylic acid in tetrahydrofuran (5 mL) with stirring under ice-cooling, and the mixture was stirred for 0.5 hour in a stream of nitrogen. To this solution was added a solution of 1.5 mL 4-flu... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccc2ncccc2c1 | HO- | O1CCCC1.O | null | null | Nc1ccc(F)cc1.O=C(O)C1CCN(c2ccnc3ccc(Br)cc23)CC1>O1CCCC1.O>O=C(Nc1ccc(F)cc1)C1CCN(c2ccnc3ccc(Br)cc23)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-505d1b14e7004be6bcec09611ab16457 | COC(=O)c1ccc(Br)cc1C.NCc1ccc(F)cc1>>O=C1c2ccc(Br)cc2CN1Cc1ccc(F)cc1 | BrN1C(CCC1=O)=O.FC1=CC=C(CN)C=C1.BrC1=CC(=C(C(=O)OC)C=C1)C.BrN1C(CCC1=O)=O.N(=NC(C#N)(C)C)C(C#N)(C)C>>BrC=1C=C2CN(C(C2=CC1)=O)CC1=CC=C(C=C1)F | CO[C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6]([Br:7])[cH:8][c:9]1[CH3:10].[NH2:11][CH2:12][c:13]1[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][c:6]([Br:7])[cH:8][c:9]2[CH2:10][N:11]1[CH2:12][c:13]1[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]1 | COC(=O)c1ccc(Br)cc1C.NCc1ccc(F)cc1 | O=C1c2ccc(Br)cc2CN1Cc1ccc(F)cc1 | null | null | C(C)N(CC)CC.CO.C(Cl)(Cl)(Cl)Cl | Acylation | OtherReaction | c927e4dc75eb4bac7b1153d8d080e9dcff38b7568211d5590ee7aa8324db2e95 | ab33057bb8fb2c9dad5b018a4f87637d8c1c3babde576dc33e825e140481b8d2 | O=C1c2ccccc2CN1Cc1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[CH3;D1;+0:6]):[c:7].[NH2;D1;+0:8]-[C:9]-[c:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[N;H0;D3;+0:8](-[C:9]-[c:10])-[CH2;D2;+0:6]-[c:5](:[c:7]):[c:3]-1:[c:4] | 34.2 | [{"value": 34.2, "product": "BrC=1C=C2CN(C(C2=CC1)=O)CC1=CC=C(C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 458 mg methyl 4-bromo-2-methylbenzoate, 427 mg N-bromosuccinimide, 25 mg α,α′-azobisisobutyronitrile and 10 mL carbon tetrachloride was heated for 30 minutes under reflux. 50 mg N-bromosuccinimide was added thereto, and the mixture was further heated for 30 minutes under reflux. The reaction solution was c... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Tertiary amide | null | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.c1ccccc1 | HO- | C(C)N(CC)CC.CO.C(Cl)(Cl)(Cl)Cl | null | null | COC(=O)c1ccc(Br)cc1C.NCc1ccc(F)cc1>C(C)N(CC)CC.CO.C(Cl)(Cl)(Cl)Cl>O=C1c2ccc(Br)cc2CN1Cc1ccc(F)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-adb0227557f042d48c4b0bb45bdb7e7a | CCO.COCCOCC(=O)O>>CCOC(=O)COCCOC | COCCOCC(=O)O.S(O)(O)(=O)=O.C(C)O>>COCCOCC(=O)OCC | [CH3:1][CH2:2][OH:3].O[C:4](=[O:5])[CH2:6][O:7][CH2:8][CH2:9][O:10][CH3:11]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][CH2:8][CH2:9][O:10][CH3:11] | CCO.COCCOCC(=O)O | CCOC(=O)COCCOC | null | null | null | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | null | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4].[C;D1;H3:5]-[C:6]-[OH;D1;+0:7]>>[#8:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C:6]-[C;D1;H3:5] | null | [] | null | null | null | null | 150 mL solution of 10 g (2-methoxyethoxy)acetic acid and 1 mL conc. sulfuric acid in ethanol was heated for 3 hours under reflux, and then the solvent was removed. The resulting residue was diluted with ethyl acetate and washed with an aqueous saturated sodium bicarbonate solution and brine. The organic layer was dried... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | null | HO- | null | null | null | CCO.COCCOCC(=O)O>>CCOC(=O)COCCOC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9ea422943cb34707b6430d78d4335819 | Nc1ccc(Cl)cn1.O=[N+]([O-])c1ccccc1F>>O=[N+]([O-])c1ccccc1Nc1ccc(Cl)cn1 | O.[OH-].[K+].FC1=C(C=CC=C1)[N+](=O)[O-].ClC=1C=CC(=NC1)N>>ClC=1C=CC(=NC1)NC1=C(C=CC=C1)[N+](=O)[O-] | [NH2:10][c:11]1[cH:12][cH:13][c:14]([Cl:15])[cH:16][n:17]1.F[c:9]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][cH:6][cH:7][cH:8]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[NH:10][c:11]1[cH:12][cH:13][c:14]([Cl:15])[cH:16][n:17]1 | Nc1ccc(Cl)cn1.O=[N+]([O-])c1ccccc1F | O=[N+]([O-])c1ccccc1Nc1ccc(Cl)cn1 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccccn2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[#7;a:10]:[c:11]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[#7;a:10]:[c:11]):[c:2]:[c:3] | 68 | [{"value": 68.0, "product": "ClC=1C=CC(=NC1)NC1=C(C=CC=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 4 | HOUR | 9.9 g potassium hydroxide powder and 5.0 g 1-fluoro-2-nitrobenzene were added little by little in this order to a solution of 5.8 g 5-chloro-2-aminopyridine in dimethyl sulfoxide (100 mL), and the mixture was stirred at 20° C. for 4 hours under nitrogen atmosphere. The reaction solution was poured into iced water and e... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccncc1 | HF | CS(=O)C | 20 | 4 | Nc1ccc(Cl)cn1.O=[N+]([O-])c1ccccc1F>CS(=O)C>O=[N+]([O-])c1ccccc1Nc1ccc(Cl)cn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b768aa0dff7c4a4d88657967b41208c1 | Fc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4cccs4)n3c2)cc1.O=C1CCC(=O)N1Br>>Fc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccc(Br)s4)n3c2)cc1 | S(=S)(=O)([O-])[O-].[Na+].[Na+].BrN1C(CCC1=O)=O.FC1=CC=C(C=C1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)C=2SC=CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2>>BrC1=CC=C(S1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(C=C2)F | [F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][n:8]([C:9]([c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)([c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[c:22]3[cH:23][cH:24][cH:25][cH:26][cH:27]3)[cH:28][c:29]2-[c:30]2[cH:31][cH:32][c:33]3[n:34][cH:35][c:36](-[c:37]4[cH:38][cH:39][cH:40][s:42]4)[n:43]3[cH:44]2)[cH:45][cH:46]1.O=... | Fc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4cccs4)n3c2)cc1.O=C1CCC(=O)N1Br | Fc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccc(Br)s4)n3c2)cc1 | null | null | CN(C=O)C | Functional Group Interconversion | Bromination | a42d5393618d10b862dd7bd471fa3f4459c31017c8714cafb4e591f8ed4a8052 | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4cccs4)n3c2)cc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#16;a:2]1:[c:3]:[c:4]:[c:5]:[cH;D2;+0:6]:1>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:6]1:[#16;a:2]:[c:3]:[c:4]:[c:5]:1 | 108.2 | [{"value": 108.2, "product": "BrC1=CC=C(S1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(C=C2)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 160 mg N-bromosuccinimide was added to 5 mL solution of 500 mg 6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]-3-(2-thienyl)imidazo[1,2-a]pyridine obtained in Example 3 in N,N-dimethylformamide, and the mixture was stirred for 1 hour. An aqueous sodium thiosulfate solution was added thereto and stirred for 30 minutes, a... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1ccsc1.C1CCNC1 | c1ccsc1 | c1ccccc1.c1c[nH]nc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccn2ccnc2c1.c1ccsc1 | HO- | CN(C=O)C | null | 1 | Fc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4cccs4)n3c2)cc1.O=C1CCC(=O)N1Br>CN(C=O)C>Fc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccc(Br)s4)n3c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-beca258f008742348208e589e2ecd2f0 | CC1(C)OB(c2ccc(C(N)=O)cc2)OC1(C)C.Fc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(I)n3c2)cc1>>NC(=O)c1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1 | FC1=CC=C(C=C1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)I)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2.P(=O)([O-])([O-])[O-].[K+].[K+].[K+].CC1(OB(OC1(C)C)C1=CC=C(C(=O)N)C=C1)C>>FC1=CC=C(C=C1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)C2=CC=C(C(=O)N)C=C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2 | CC1(C)OB([c:7]2[cH:6][cH:5][c:4]([C:2]([NH2:1])=[O:3])[cH:49][cH:48]2)OC1(C)C.I[c:8]1[cH:9][n:10][c:11]2[cH:12][cH:13][c:14](-[c:15]3[cH:16][n:17]([C:18]([c:19]4[cH:20][cH:21][cH:22][cH:23][cH:24]4)([c:25]4[cH:26][cH:27][cH:28][cH:29][cH:30]4)[c:31]4[cH:32][cH:33][cH:34][cH:35][cH:36]4)[n:37][c:38]3-[c:39]3[cH:40][cH:4... | CC1(C)OB(c2ccc(C(N)=O)cc2)OC1(C)C.Fc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(I)n3c2)cc1 | NC(=O)c1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | CN(C=O)C | C-C Coupling | Suzuki coupling with boronic esters | dcda447711556696a2b0cc312b40d9049503597a5d54a34fea6736b791985a24 | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccc4)n3c2)cc1 | C-C1(-C)-O-B(-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-O-C-1(-C)-C.I-[c;H0;D3;+0:6]1:[c:7]:[#7;a:8]:[c:9](:[c:10]):[#7;a:11]:1:[c:12]>>[c:10]:[c:9]1:[#7;a:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[#7;a:11]:1:[c:12] | 43.2 | [{"value": 43.2, "product": "FC1=CC=C(C=C1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)C2=CC=C(C(=O)N)C=C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 222 mg of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide prepared according to T. Ishiyama et al., J. Org. Chem., 60, 7508 (1995), 323 mg of 6-[3-(4-fluorophenyl)-1-trityl-1H-pyrazolyl]-3-iodoimidazo[1,2-a]pyridine (compound in Production Example 39), 200 mg tripotassium phosphate, 30 mg tetrakis(triphenylpho... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | B1OCCO1.c1ccccc1.c1ccn2ccnc2c1 | c1ccccc1.c1ccn2ccnc2c1 | c1ccccc1.c1ccn2ccnc2c1.c1cn[nH]c1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HI.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.CN(C=O)C | null | null | CC1(C)OB(c2ccc(C(N)=O)cc2)OC1(C)C.Fc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(I)n3c2)cc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.CN(C=O)C>NC(=O)c1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc... |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-80dfa5754aae434986bc35ed32398ad0 | [N-]=[N+]=NCCCOc1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1>>NCCCOc1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1 | O.S(=O)(=O)([O-])[O-].[Na+].[Na+].FC1=CC=C(C=C1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)C2=CC=C(OCCCN=[N+]=[N-])C=C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2.C(CCC)P>>FC1=CC=C(C=C1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)C2=CC=C(OCCCN)C=C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2 | [N-]=[N+]=[N:1][CH2:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9](-[c:10]2[cH:11][n:12][c:13]3[cH:14][cH:15][c:16](-[c:17]4[cH:18][n:19]([C:20]([c:21]5[cH:22][cH:23][cH:24][cH:25][cH:26]5)([c:27]5[cH:28][cH:29][cH:30][cH:31][cH:32]5)[c:33]5[cH:34][cH:35][cH:36][cH:37][cH:38]5)[n:39][c:40]4-[c:41]4[cH:42][cH:43][c:44]([F... | [N-]=[N+]=NCCCOc1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1 | NCCCOc1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1 | null | null | O1CCCC1.C(C)(=O)OCC | Reduction | Azide to amine reduction (Staudinger) | 4c9e4990dae2bb965dec06bd45e318560989ee3681b61e443f7aa363b7cfa222 | cd009d687d606bf351eac9390a176d16be38f2c8216a599b398641009c215027 | c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccc4)n3c2)cc1 | [C:1]-[C:2]-[N;H0;D2;+0:3]=[N+]=[N-]>>[C:1]-[C:2]-[NH2;D1;+0:3] | 84.9 | [{"value": 84.9, "product": "FC1=CC=C(C=C1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)C2=CC=C(OCCCN)C=C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of 351 mg 3-(4-{6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]imidazo[1,2-a]pyridin-3-yl}phenoxy)-propyl azide obtained in Example 15 in 10 mL tetrahydrofuran was stirred at room temperature in a stream of nitrogen, 0.15 mL n-butyl phosphine was added thereto and stirred for 2 hours. Then, 2 mL water was add... | 10.6084/m9.figshare.5104873.v1 | null | Azide | Primary amine | null | null | c1ccccc1.c1ccn2ccnc2c1.c1cn[nH]c1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | Other | O1CCCC1.C(C)(=O)OCC | null | 2 | [N-]=[N+]=NCCCOc1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1>O1CCCC1.C(C)(=O)OCC>NCCCOc1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1d936ddfd3c54eee965be322edd313ac | CC(=O)OC(C)=O.NCCCOc1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1>>CC(=O)NCCCOc1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1 | FC1=CC=C(C=C1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)C2=CC=C(OCCCN)C=C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2.C(C)N(CC)CC.C(C)(=O)OC(C)=O.C([O-])(O)=O.[Na+]>>FC1=CC=C(C=C1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)C2=CC=C(OCCCNC(C)=O)C=C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2 | CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][CH2:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12](-[c:13]2[cH:14][n:15][c:16]3[cH:17][cH:18][c:19](-[c:20]4[cH:21][n:22]([C:23]([c:24]5[cH:25][cH:26][cH:27][cH:28][cH:29]5)([c:30]5[cH:31][cH:32][cH:33][cH:34][cH:35]5)[c:36]5[cH:37][cH:38][cH:39][cH:40][cH:41]5)[n:42][c:43]4-[c:44]4... | CC(=O)OC(C)=O.NCCCOc1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1 | CC(=O)NCCCOc1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1 | null | null | ClCCl.C(C)(=O)OCC | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccc4)n3c2)cc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5]-[NH2;D1;+0:6]>>[C:4]-[C:5]-[NH;D2;+0:6]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | null | [] | null | null | 1 | HOUR | While 5 mL solution of 37 mg 3-(4-{6-[3-(4-Fluorophenyl)-1-trityl-1H-4-pyrazolyl]imidazo[1,2-a]pyridin-3-yl}phenoxy)-propylamine obtained in Example 16 and 20 mg triethylamine in dichloromethane was stirred under ice-coolingd water in a stream of nitrogen, 9 μL acetic anhydride was added thereto and stirred for 1 hour.... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccn2ccnc2c1.c1cn[nH]c1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | ClCCl.C(C)(=O)OCC | null | 1 | CC(=O)OC(C)=O.NCCCOc1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1>ClCCl.C(C)(=O)OCC>CC(=O)NCCCOc1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7a3962de839644cbaf8196ec8b4dba5b | COC(=O)CCC(=O)Cl.NCCCOc1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1>>COC(=O)CCC(=O)NCCCOc1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1 | FC1=CC=C(C=C1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)C2=CC=C(OCCCN)C=C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2.ClC(CCC(=O)OC)=O>>FC1=CC=C(C=C1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)C2=CC=C(OCCCNC(CCC(=O)OC)=O)C=C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2 | Cl[C:7]([CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])=[O:8].[NH2:9][CH2:10][CH2:11][CH2:12][O:13][c:14]1[cH:15][cH:16][c:17](-[c:18]2[cH:19][n:20][c:21]3[cH:22][cH:23][c:24](-[c:25]4[cH:26][n:27]([C:28]([c:29]5[cH:30][cH:31][cH:32][cH:33][cH:34]5)([c:35]5[cH:36][cH:37][cH:38][cH:39][cH:40]5)[c:41]5[cH:42][cH:43][cH:44][cH:4... | COC(=O)CCC(=O)Cl.NCCCOc1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1 | COC(=O)CCC(=O)NCCCOc1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccc4)n3c2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[C:5](-[#8:6])=[O;D1;H0:7].[C:8]-[C:9]-[NH2;D1;+0:10]>>[#8:6]-[C:5](=[O;D1;H0:7])-[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[C:9]-[C:8] | null | [] | null | null | null | null | 41 mg of 3-(4-{6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]imidazo[1,2-a]pyridin-3-yl}phenoxy)propylamine obtained in Example 16 and 12 μL methyl 4-chloro-4-oxobutyrate were reacted in the same manner as in Example 17, to give 24 mg of the title compound as a colorless amorphous.
Conditions: See reaction.notes.proced... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccn2ccnc2c1.c1cn[nH]c1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HCl | null | null | null | COC(=O)CCC(=O)Cl.NCCCOc1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1>>COC(=O)CCC(=O)NCCCOc1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-864de2facee847e2a759f4c38964c169 | CS(=O)(=O)Cl.Nc1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1>>CS(=O)(=O)Nc1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1 | FC1=CC=C(C=C1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)C2=CC=C(N)C=C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2.C(C)N(CC)CC.CS(=O)(=O)Cl.O>>FC1=CC=C(C=C1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)C2=CC=C(C=C2)NS(=O)(=O)C)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2 | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[NH2:5][c:6]1[cH:7][cH:8][c:9](-[c:10]2[cH:11][n:12][c:13]3[cH:14][cH:15][c:16](-[c:17]4[cH:18][n:19]([C:20]([c:21]5[cH:22][cH:23][cH:24][cH:25][cH:26]5)([c:27]5[cH:28][cH:29][cH:30][cH:31][cH:32]5)[c:33]5[cH:34][cH:35][cH:36][cH:37][cH:38]5)[n:39][c:40]4-[c:41]4[cH:42][cH:43][c:44]([F:45... | CS(=O)(=O)Cl.Nc1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1 | CS(=O)(=O)Nc1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1 | null | null | ClCCl | Miscellaneous | Sulfonamide synthesis (Schotten-Baumann) primary amine | a86b0632821e188c0a5dc5a5a2aac298ab3eccaee8a52ba46078c3d5975a290d | 50f8fbf3d327483c3eeff8f6cbd4065e4c7600bb501fbe08958a5c79a0926428 | c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccc4)n3c2)cc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | 3 | HOUR | While 7 mL solution of 68 mg 4-{6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]imidazo[1,2-a]pyridin-3-yl}aniline obtained in Example 19 and 34 mg triethylamine in dichloromethane was stirred in a stream of nitrogen, 20 μL methylsulfonyl chloride was added thereto. Then, the mixture was stirred at room temperature for 3... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccn2ccnc2c1.c1cn[nH]c1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HCl | ClCCl | null | 3 | CS(=O)(=O)Cl.Nc1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1>ClCCl>CS(=O)(=O)Nc1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ce600d8bef3f43d48a6b925f547a42ac | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccccn1.Fc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccc(Br)s4)n3c2)cc1>>Fc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccc(-c5ccccn5)s4)n3c2)cc1 | BrC1=CC=C(S1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(C=C2)F.C(CCC)[Sn](C1=NC=CC=C1)(CCCC)CCCC>>FC1=CC=C(C=C1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)C=2SC(=CC2)C2=NC=CC=C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c:41]1[cH:42][cH:43][cH:44][cH:45][n:46]1.Br[c:40]1[cH:39][cH:38][c:37](-[c:36]2[cH:35][n:34][c:33]3[cH:32][cH:31][c:30](-[c:29]4[c:6](-[c:5]5[cH:4][cH:3][c:2]([F:1])[cH:51][cH:50]5)[n:7][n:8]([C:9]([c:10]5[cH:11][cH:12][cH:13][cH:14][cH:15]5)([c:16]5[cH:17][cH:18][cH:19][cH:20][cH:21]5... | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccccn1.Fc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccc(Br)s4)n3c2)cc1 | Fc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccc(-c5ccccn5)s4)n3c2)cc1 | null | null | null | C-C Coupling | Stille reaction_aryl | 3425d5ef474ac492d729217c828778be98425b4bb83e1deca75d3993966cee49 | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccc(-c5ccccn5)s4)n3c2)cc1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[c:5]:1.C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[c;H0;D3;+0:6](:[#7;a:7]:[c:8]):[c:9]:[c:10]>>[c:10]:[c:9]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[c:5]:1):[#7;a:7]:[c:8] | null | [] | null | null | null | null | 150 mg of 3-(5-bromo-2-thienyl)-6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]imidazo[1,2-a]pyridine obtained in Example 4 and 0.13 mL of 2-(tri-n-butylstannyl)pyridine were reacted in the same manner as in Example 21, to give 137 mg of the title compound as a yellow amorphous.
Conditions: See reaction.notes.procedure_... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1ccncc1.c1ccsc1 | c1ccsc1.c1ccncc1 | c1ccccc1.c1c[nH]nc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccn2ccnc2c1.c1ccsc1.c1ccncc1 | HBr.Sn | null | null | null | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccccn1.Fc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccc(Br)s4)n3c2)cc1>>Fc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccc(-c5ccccn5)s4)n3c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e0a40e1389a5425c8e20f1e27a7c1270 | CSc1ccc(-c2cnc3ccc(Br)cn23)s1.OB(O)c1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)nc1-c1ccc(F)cc1>>CSc1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)s1 | FC1=CC=C(C=C1)C1=NN(C=C1B(O)O)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.BrC=1C=CC=2N(C1)C(=CN2)C=2SC(=CC2)SC.C1(=CC=CC=C1)C.C([O-])([O-])=O.[Na+].[Na+]>>FC1=CC=C(C=C1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)C=2SC(=CC2)SC)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2 | Br[c:13]1[cH:12][cH:11][c:10]2[n:9][cH:8][c:7](-[c:6]3[cH:5][cH:4][c:3]([S:2][CH3:1])[s:47]3)[n:46]2[cH:45]1.OB(O)[c:14]1[cH:15][n:16]([C:17]([c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)([c:24]2[cH:25][cH:26][cH:27][cH:28][cH:29]2)[c:30]2[cH:31][cH:32][cH:33][cH:34][cH:35]2)[n:36][c:37]1-[c:38]1[cH:39][cH:40][c:41]([F:... | CSc1ccc(-c2cnc3ccc(Br)cn23)s1.OB(O)c1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)nc1-c1ccc(F)cc1 | CSc1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)s1 | null | null | C(C)O | C-C Coupling | Suzuki coupling with boronic acids | 4a9aa793a206991f9635e02534e1ad0504f7e731cb01a80b0b0ca55413841f06 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4cccs4)n3c2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:2:[c:9]:1.O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[#7;a:12](-[C:13]):[#7;a:14]:[c:15]:1-[c:16]>>[C:13]-[#7;a:12]1:[#7;a:14]:[c:15](-[c:16]):[c;H0;D3;+0:10](-[c;H0;D3;+0:1]2:[c:2]:[c:3]:[c:4]3:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:3:[c:9]:2):[c:11]:1 | 64.3 | [{"value": 64.3, "product": "FC1=CC=C(C=C1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)C=2SC(=CC2)SC)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 736 mg 3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolylboronic acid (compound in Production Example 25), 550 mg 6-bromo-3-[5-(methylsulfanyl)-2-thienyl]imidazo[1,2-a]-pyridine (compound in Production Example 58) and 100 mg tetrakis (triphenylphosphine)palladium were stirred at 80° C. for 3 hours in a solution mixture of 5 mL... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccn2ccnc2c1.c1cn[nH]c1 | c1ccn2ccnc2c1.c1cn[nH]c1 | c1ccsc1.c1ccn2ccnc2c1.c1cn[nH]c1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HBr.B | C(C)O | null | null | CSc1ccc(-c2cnc3ccc(Br)cn23)s1.OB(O)c1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)nc1-c1ccc(F)cc1>C(C)O>CSc1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)s1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1435329b8b3e46a5a161aba6177db323 | N#Cc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccc(CN5CCC[C@H]5CC(N)=O)s4)n3c2)cc1>>N#Cc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccc(CN5CCC[C@H]5C#N)s4)n3c2)cc1 | C(#N)C1=CC=C(C=C1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)C2=CC=C(S2)CN2[C@@H](CCC2)CC(=O)N)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2.N1=CC=CC=C1.FC(C(=O)OC(C(F)(F)F)=O)(F)F>>C(#N)C1=CC=C(C=C1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)C2=CC=C(S2)CN2[C@@H](CCC2)C#N)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2 | O=C([CH2:48][C@H:47]1[N:43]([CH2:42][c:41]2[cH:40][cH:39][c:38](-[c:37]3[cH:36][n:35][c:34]4[cH:33][cH:32][c:31](-[c:30]5[c:7](-[c:6]6[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:54][cH:53]6)[n:8][n:9]([C:10]([c:11]6[cH:12][cH:13][cH:14][cH:15][cH:16]6)([c:17]6[cH:18][cH:19][cH:20][cH:21][cH:22]6)[c:23]6[cH:24][cH:25][cH:26][cH:2... | N#Cc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccc(CN5CCC[C@H]5CC(N)=O)s4)n3c2)cc1 | N#Cc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccc(CN5CCC[C@H]5C#N)s4)n3c2)cc1 | null | null | O1CCCC1 | Miscellaneous | OtherReaction | 5094e9d814705bbdc421edbf7e9198e499e70e93916e2cec6eefbc82d1ba5440 | 32b9893bcb5223559a9d02852f8392cf6473aacfb044a52ba4e9cb9c29edb170 | c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccc(CN5CCCC5)s4)n3c2)cc1 | O=C(-[NH2;D1;+0:1])-[CH2;D2;+0:2]-[C:3](-[C:4])-[#7:5](-[C:6])-[C:7]>>[C:6]-[#7:5](-[C:7])-[C:3](-[C;H0;D2;+0:2]#[N;H0;D1;+0:1])-[C:4] | null | [] | null | null | 30 | MINUTE | While 144 mg of (2S)-1-[(5-{6-[3-(4-cyanophenyl)-1-trityl-1H-4-pyrazolyl]imidazo[1,2-a]pyridin-3-yl}-2-thienyl)methyl]tetrahydro-1H-2-pyrrole carboxyamide obtained in Example 35 was cooled in 1 mL tetrahydrofuran under ice-cooling, 0.05 mL pyridine and 0.57 mL trifluoroacetic anhydride were added thereto, and the mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide | Nitrile | null | null | c1ccccc1.c1c[nH]nc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccn2ccnc2c1.c1ccsc1.C1CC[NH]C1 | HO- | O1CCCC1 | null | 0.5 | N#Cc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccc(CN5CCC[C@H]5CC(N)=O)s4)n3c2)cc1>O1CCCC1>N#Cc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccc(CN5CCC[C@H]5C#N)s4)n3c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e731a84609504c2dbead9bf2573f28a6 | O=C(O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1.[NH4+]>>NC(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 | F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N2CCCC2)(N2CCCC2)N2CCCC2.O.ON1N=NC2=C1C=CC=C2.C(C)(C)N(CC)C(C)C.[Cl-].[NH4+].N1=C(C=CC=C1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(C(=O)O)C=C2>>N1=C(C=CC=C1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(C(=O... | O[C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[n:9][n:10]([C:11]([c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)([c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[c:24]3[cH:25][cH:26][cH:27][cH:28][cH:29]3)[cH:30][c:31]2-[c:32]2[cH:33][cH:34][c:35]3[n:36][cH:37][c:38](-[c:39]4[cH:40][cH:41][cH:42][cH:43][n:44]4)[n:45]3[cH:46]2)... | O=C(O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1.[NH4+] | NC(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 | null | null | O.CN(C=O)C.C(C)(=O)OCC | Acylation | Carboxylic acid to amide conversion | 1283aef55d7ee699f097a8e5267689198c76ba671644401547f902657820236d | cb0a71c3fb37a76e96fbd81aae6f95a28398a03d1ad2c8e877085e735efb98f1 | c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH4+;D0:6]>>[NH2;D1;+0:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 114.2 | [{"value": 114.2, "product": "N1=C(C=CC=C1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(C(=O)N)C=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 125 mg benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate, 1-hydroxy-1H-benzotriazole monohydrate, 83 mg diisopropylethylamine, and 18 mg ammonium chloride were added in this order to a mixture of 100 mg 4-{4-[3-(2-pyridyl)imidazo[1,2-a]pyridin-6-yl]-1-trityl-1H-3-pyrazolyl} benzoic acid obtained in Exam... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | c1ccccc1.c1c[nH]nc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccn2ccnc2c1.c1ccncc1 | HO- | O.CN(C=O)C.C(C)(=O)OCC | null | 2 | O=C(O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1.[NH4+]>O.CN(C=O)C.C(C)(=O)OCC>NC(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1612ef01a6a24b24a4a1a3a81af688e4 | C1COCCN1.O=C(O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1>>O=C(c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1)N1CCOCC1 | CN1CCOCC1.O.ON1N=NC2=C1C=CC=C2.N1=C(C=CC=C1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(C(=O)O)C=C2.N1CCOCC1.Cl.C(C)N=C=NCCCN(C)C>>O1CCN(CC1)C(=O)C1=CC=C(C=C1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)C2=NC=CC=C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2 | [NH:48]1[CH2:49][CH2:50][O:51][CH2:52][CH2:53]1.O[C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][n:9]([C:10]([c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)([c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[c:23]3[cH:24][cH:25][cH:26][cH:27][cH:28]3)[cH:29][c:30]2-[c:31]2[cH:32][cH:33][c:34]3[n:35][cH:36][c:37](-[c:38]4[cH:3... | C1COCCN1.O=C(O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 | O=C(c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1)N1CCOCC1 | null | null | O.CN(C=O)C.C(C)(=O)OCC | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | 2ef483949e7ba3e5f888cf14cdce25fa611f75be09fdf1854a473be519821b59 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1)N1CCOCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#8:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#8:6]-[C:11]-[C:10]-1)-[c:3](:[c:4]):[c:5] | 93.6 | [{"value": 93.6, "product": "O1CCN(CC1)C(=O)C1=CC=C(C=C1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)C2=NC=CC=C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 17 mg N-methyl morpholine and 13 mg 1-hydroxy-1H-benzotriazole monohydrate were added in this order at room temperature to a mixture of 50 mg 4-{4-[3-(2-pyridyl)imidazo[1,2-a]pyridin-6-yl]-1-trityl-1H-3-pyrazolyl} benzoic acid obtained in Example 46, 7.7 mg morpholine, 17 mg 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimi... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1COCCN1 | C1COCC[NH]1 | c1ccccc1.c1c[nH]nc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccn2ccnc2c1.c1ccncc1.C1COCC[NH]1 | HO- | O.CN(C=O)C.C(C)(=O)OCC | null | null | C1COCCN1.O=C(O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1>O.CN(C=O)C.C(C)(=O)OCC>O=C(c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1)N1CCOCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5856381ae3f04a8089fe7703c3c8e459 | O=C(O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>>Nc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 | N1=C(C=CC=C1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(C(=O)O)C=C2.C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)N=[N+]=[N-].C([O-])([O-])=O.[K+].[K+].CN(C=O)C>>N1=C(C=CC=C1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(N)C=C2 | O=C(O)[c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][n:8]([C:9]([c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)([c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[c:22]3[cH:23][cH:24][cH:25][cH:26][cH:27]3)[cH:28][c:29]2-[c:30]2[cH:31][cH:32][c:33]3[n:34][cH:35][c:36](-[c:37]4[cH:38][cH:39][cH:40][cH:41][n:42]4)[n:43]3[cH:44]2)[cH:45][cH... | O=C(O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1 | Nc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 | null | null | O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 1669d6f6b21474b6c6672f2d5188f5d88e1ec82f458d78237613d514f0e1abdc | c4869b2e15981984090372c3f8725c0a3f1a2d8cd3a4eec59edd04a0d3b2a386 | c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 | O-C(=O)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O=P(-[N;H0;D2;+0:6]=[N+]=[N-])(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[NH2;D1;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 31.5 | [{"value": 31.5, "product": "N1=C(C=CC=C1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(N)C=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 6 | HOUR | A mixture of 100 mg 4-{4-[3-(2-pyridyl)imidazo[1,2-a]pyridin-6-yl]-1-trityl-1H-3-pyrazolyl}benzoic acid obtained in Example 48, 44 mg diphenyl phosphoryl azide, 23 mg potassium carbonate, and 4 mL N,N-dimethylformamide was stirred at 80° C. for 6 hours. Ethyl acetate and water were added to the reaction solution, and t... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Azide | Primary amine | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1c[nH]nc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccn2ccnc2c1.c1ccncc1 | HO- | O.C(C)(=O)OCC | 80 | 6 | O=C(O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>O.C(C)(=O)OCC>Nc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-de203dd9b1d74014a54716b53a9de7c2 | CS(=O)(=O)Cl.Nc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1>>CS(=O)(=O)Nc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 | N1=C(C=CC=C1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(N)C=C2.CS(=O)(=O)Cl>>N1=C(C=CC=C1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(C=C2)NS(=O)(=O)C | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[NH2:5][c:6]1[cH:7][cH:8][c:9](-[c:10]2[n:11][n:12]([C:13]([c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)([c:20]3[cH:21][cH:22][cH:23][cH:24][cH:25]3)[c:26]3[cH:27][cH:28][cH:29][cH:30][cH:31]3)[cH:32][c:33]2-[c:34]2[cH:35][cH:36][c:37]3[n:38][cH:39][c:40](-[c:41]4[cH:42][cH:43][cH:44][cH:4... | CS(=O)(=O)Cl.Nc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 | CS(=O)(=O)Nc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 | null | null | null | Miscellaneous | Sulfonamide synthesis (Schotten-Baumann) primary amine | a86b0632821e188c0a5dc5a5a2aac298ab3eccaee8a52ba46078c3d5975a290d | 50f8fbf3d327483c3eeff8f6cbd4065e4c7600bb501fbe08958a5c79a0926428 | c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | null | null | 26 mg 4-{4-[3-(2-pyridyl)imidazo[1,2-a]pyridin-6-yl]-1-trityl-1H-3-pyrazolyl}aniline obtained in Example 49 and 9 μL methyl sulfonyl chloride were reacted in the same manner as in Example 20, to give 14 mg of the title compound as a colorless amorphous.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1c[nH]nc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccn2ccnc2c1.c1ccncc1 | HCl | null | null | null | CS(=O)(=O)Cl.Nc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1>>CS(=O)(=O)Nc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cd4666a33ca84b58a1bda57659621282 | Fc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(I)n3c2)cc1.N#Cc1cccc(B(O)O)c1>>N#Cc1cccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)c1 | C(#N)C=1C=C(C=CC1)B(O)O.FC1=CC=C(C=C1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)I)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2>>FC1=CC=C(C=C1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)C=2C=C(C#N)C=CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2 | I[c:8]1[cH:9][n:10][c:11]2[cH:12][cH:13][c:14](-[c:15]3[cH:16][n:17]([C:18]([c:19]4[cH:20][cH:21][cH:22][cH:23][cH:24]4)([c:25]4[cH:26][cH:27][cH:28][cH:29][cH:30]4)[c:31]4[cH:32][cH:33][cH:34][cH:35][cH:36]4)[n:37][c:38]3-[c:39]3[cH:40][cH:41][c:42]([F:43])[cH:44][cH:45]3)[cH:46][n:47]12.OB(O)[c:7]1[cH:6][cH:5][cH:4][... | Fc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(I)n3c2)cc1.N#Cc1cccc(B(O)O)c1 | N#Cc1cccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)c1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 6d2f92e38cbc7faf246cda8a4b8669001b5c18f23ff87160bd75535916dab019 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccc4)n3c2)cc1 | I-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4](:[c:5]):[#7;a:6]:1:[c:7].O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[c:5]:[c:4]1:[#7;a:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[#7;a:6]:1:[c:7] | 87.8 | [{"value": 87.8, "product": "FC1=CC=C(C=C1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)C=2C=C(C#N)C=CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 46 mg 3-cyanophenylboronic acid and 161 mg 6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]-3-iodoimidazo[1,2-a]pyridine (compound in Production Example 39) were reacted in the same manner as in Example 3, to give 136 mg 3-{6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]imidazo[1,2-a]pyridin-3-yl} benzonitrile as colorles... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccn2ccnc2c1.c1ccccc1 | c1ccccc1.c1ccn2ccnc2c1 | c1ccccc1.c1ccn2ccnc2c1.c1cn[nH]c1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HI.B | null | null | null | Fc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(I)n3c2)cc1.N#Cc1cccc(B(O)O)c1>>N#Cc1cccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5e44504fea6949a9aea92f49e40b8f89 | NS(=O)(=O)c1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1>>Cl.NS(=O)(=O)c1ccc(-c2cnc3ccc(-c4c[nH]nc4-c4ccc(F)cc4)cn23)cc1 | FC1=CC=C(C=C1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)C2=CC=C(C=C2)S(=O)(=O)N)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2.Cl>>Cl.Cl.FC1=CC=C(C=C1)C1=NNC=C1C=1C=CC=2N(C1)C(=CN2)C2=CC=C(C=C2)S(=O)(=O)N | c1ccc(C(c2ccccc2)(c2ccccc2)[n:20]2[cH:19][c:18](-[c:17]3[cH:16][cH:15][c:14]4[n:13][cH:12][c:11](-[c:10]5[cH:9][cH:8][c:7]([S:4]([NH2:3])(=[O:5])=[O:6])[cH:33][cH:32]5)[n:31]4[cH:30]3)[c:22](-[c:23]3[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]3)[n:21]2)cc1>>[ClH:2].[NH2:3][S:4](=[O:5])(=[O:6])[c:7]1[cH:8][cH:9][c:10](-[c... | NS(=O)(=O)c1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1 | Cl.NS(=O)(=O)c1ccc(-c2cnc3ccc(-c4c[nH]nc4-c4ccc(F)cc4)cn23)cc1 | null | null | O1CCCC1.CO | Functional Group Interconversion | OtherReaction | f8945b6c47d2fe181548474e648e16cfeefa7d5db2d97918e7510aa55a3c60d6 | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | c1ccc(-c2n[nH]cc2-c2ccc3ncc(-c4ccccc4)n3c2)cc1 | [#7;a:1]1:[c:2]:[c:3]:[c:4]:[n;H0;D3;+0:5]:1-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#7;a:1]1:[c:2]:[c:3]:[c:4]:[nH;D2;+0:5]:1 | null | [] | null | null | 3 | HOUR | 185 mg 4-{6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]imidazo[1,2-a]pyridin-3-yl}-1-benzene sulfonamide obtained in Example 11 was dissolved in 3.5 mL solvent mixture of tetrahydrofuran and methanol (1:1), then 3.5 mL of 5 N hydrochloric acid was added thereto, and the mixture was stirred at room temperature for 3 ho... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1cn[nH]c1 | c1cn[nH]c1 | c1ccccc1.c1ccn2ccnc2c1.c1cn[nH]c1.c1ccccc1 | Other | O1CCCC1.CO | null | 3 | NS(=O)(=O)c1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1>O1CCCC1.CO>Cl.NS(=O)(=O)c1ccc(-c2cnc3ccc(-c4c[nH]nc4-c4ccc(F)cc4)cn23)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-081d62b82af24a3a9c58599dd0049bb0 | Fc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1>>Fc1ccc(-c2n[nH]cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 | [OH-].[Na+].FC1=CC=C(C=C1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)C2=NC=CC=C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2.Cl.O1CCCC1>>FC1=CC=C(C=C1)C1=NNC=C1C=1C=CC=2N(C1)C(=CN2)C2=NC=CC=C2 | c1ccc(C(c2ccccc2)(c2ccccc2)[n:8]2[n:7][c:6](-[c:5]3[cH:4][cH:3][c:2]([F:1])[cH:27][cH:26]3)[c:10](-[c:11]3[cH:12][cH:13][c:14]4[n:15][cH:16][c:17](-[c:18]5[cH:19][cH:20][cH:21][cH:22][n:23]5)[n:24]4[cH:25]3)[cH:9]2)cc1>>[F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][nH:8][cH:9][c:10]2-[c:11]2[cH:12][cH:13][c:14]3[n:15][cH:1... | Fc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 | Fc1ccc(-c2n[nH]cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 | null | null | O.CO.C(C)(=O)OCC | Deprotection | OtherReaction | 92b7543875cfe438a4c5cf3faf8e6c828b5eea356096f8ebdcd8d3241dc18933 | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | c1ccc(-c2n[nH]cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 | [#7;a:1]1:[c:2]:[c:3]:[c:4]:[n;H0;D3;+0:5]:1-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#7;a:1]1:[c:2]:[c:3]:[c:4]:[nH;D2;+0:5]:1 | 44.6 | [{"value": 44.6, "product": "FC1=CC=C(C=C1)C1=NNC=C1C=1C=CC=2N(C1)C(=CN2)C2=NC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 147 mg 6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]-3-(2-pyridyl)imidazo[1,2-a]pyridine obtained in Example 22, 1.8 mL of 5 N hydrochloric acid, 4 ml tetrahydrofuran and 4 mL methanol were stirred overnight at room temperature. The reaction solution was cooled and then basified with 5 N aqueous sodium hydroxide, foll... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1cn[nH]c1 | c1cn[nH]c1 | c1ccccc1.c1cn[nH]c1.c1ccn2ccnc2c1.c1ccncc1 | Other | O.CO.C(C)(=O)OCC | null | null | Fc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1>O.CO.C(C)(=O)OCC>Fc1ccc(-c2n[nH]cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3f3a3ddd8e994a8ea7894fc41e311a1d | CS(=O)(=O)Nc1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1>>CS(=O)(=O)Nc1ccc(-c2cnc3ccc(-c4c[nH]nc4-c4ccc(F)cc4)cn23)cc1 | [OH-].[Na+].FC1=CC=C(C=C1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)C2=CC=C(C=C2)NS(=O)(=O)C)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2.FC(C(=O)O)(F)F.ClCCl>>FC1=CC=C(C=C1)C1=NNC=C1C=1C=CC=2N(C1)C(=CN2)C2=CC=C(C=C2)NS(=O)(=O)C | c1ccc(C(c2ccccc2)(c2ccccc2)[n:19]2[cH:18][c:17](-[c:16]3[cH:15][cH:14][c:13]4[n:12][cH:11][c:10](-[c:9]5[cH:8][cH:7][c:6]([NH:5][S:2]([CH3:1])(=[O:3])=[O:4])[cH:32][cH:31]5)[n:30]4[cH:29]3)[c:21](-[c:22]3[cH:23][cH:24][c:25]([F:26])[cH:27][cH:28]3)[n:20]2)cc1>>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9](-... | CS(=O)(=O)Nc1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1 | CS(=O)(=O)Nc1ccc(-c2cnc3ccc(-c4c[nH]nc4-c4ccc(F)cc4)cn23)cc1 | null | null | O.C(C)(=O)OCC | Deprotection | OtherReaction | 92b7543875cfe438a4c5cf3faf8e6c828b5eea356096f8ebdcd8d3241dc18933 | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | c1ccc(-c2n[nH]cc2-c2ccc3ncc(-c4ccccc4)n3c2)cc1 | [#7;a:1]1:[c:2]:[c:3]:[c:4]:[n;H0;D3;+0:5]:1-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#7;a:1]1:[c:2]:[c:3]:[c:4]:[nH;D2;+0:5]:1 | 71.6 | [{"value": 71.6, "product": "FC1=CC=C(C=C1)C1=NNC=C1C=1C=CC=2N(C1)C(=CN2)C2=CC=C(C=C2)NS(=O)(=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of 71 mg N-(4-{6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]imidazo[1,2-a]pyridin-3-yl}phenyl)-methane sulfonamide obtained in Example 20, 0.36 mL trifluoroacetic acid and 5 mL dichloromethane was stirred overnight at room temperature. The reaction solution was cooled and made weakly alkaline with 5 N aqueou... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1cn[nH]c1 | c1cn[nH]c1 | c1ccccc1.c1ccn2ccnc2c1.c1cn[nH]c1.c1ccccc1 | Other | O.C(C)(=O)OCC | null | 8 | CS(=O)(=O)Nc1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1>O.C(C)(=O)OCC>CS(=O)(=O)Nc1ccc(-c2cnc3ccc(-c4c[nH]nc4-c4ccc(F)cc4)cn23)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5dad66efd2fb425cb879754685a99574 | NCCCNC(=O)c1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1>>NCCCNC(=O)c1ccc(-c2cnc3ccc(-c4c[nH]nc4-c4ccc(F)cc4)cn23)cc1 | NCCCNC(C1=CC=C(C=C1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(C=C2)F)=O.O1CCCC1.Cl>>NCCCNC(C1=CC=C(C=C1)C1=CN=C2N1C=C(C=C2)C=2C(=NNC2)C2=CC=C(C=C2)F)=O | c1ccc(C(c2ccccc2)(c2ccccc2)[n:21]2[cH:20][c:19](-[c:18]3[cH:17][cH:16][c:15]4[n:14][cH:13][c:12](-[c:11]5[cH:10][cH:9][c:8]([C:6]([NH:5][CH2:4][CH2:3][CH2:2][NH2:1])=[O:7])[cH:34][cH:33]5)[n:32]4[cH:31]3)[c:23](-[c:24]3[cH:25][cH:26][c:27]([F:28])[cH:29][cH:30]3)[n:22]2)cc1>>[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:... | NCCCNC(=O)c1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1 | NCCCNC(=O)c1ccc(-c2cnc3ccc(-c4c[nH]nc4-c4ccc(F)cc4)cn23)cc1 | null | null | CO | Deprotection | OtherReaction | 92b7543875cfe438a4c5cf3faf8e6c828b5eea356096f8ebdcd8d3241dc18933 | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | c1ccc(-c2n[nH]cc2-c2ccc3ncc(-c4ccccc4)n3c2)cc1 | [#7;a:1]1:[c:2]:[c:3]:[c:4]:[n;H0;D3;+0:5]:1-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#7;a:1]1:[c:2]:[c:3]:[c:4]:[nH;D2;+0:5]:1 | 46 | [{"value": 46.0, "product": "NCCCNC(C1=CC=C(C=C1)C1=CN=C2N1C=C(C=C2)C=2C(=NNC2)C2=CC=C(C=C2)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 50 mg N1-(3-aminopropyl)-4-{6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]imidazo[1,2-a]pyridin-3-yl}benzamide obtained in Example 43 in a solvent mixture of 1.5 mL tetrahydrofuran, 1.5 mL methanol and 1.5 mL of 5 N hydrochloric acid was left at room temperature for 1 hour. The mixture was washed with eth... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1cn[nH]c1 | c1cn[nH]c1 | c1ccccc1.c1ccn2ccnc2c1.c1cn[nH]c1.c1ccccc1 | Other | CO | null | 1 | NCCCNC(=O)c1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1>CO>NCCCNC(=O)c1ccc(-c2cnc3ccc(-c4c[nH]nc4-c4ccc(F)cc4)cn23)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0afd9286cd364dabbada624a7974cb1d | CC(=O)OC(C)=O.NCCCNC(=O)c1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1>>CC(=O)NCCCNC(=O)c1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1 | C(C)(=O)OC(C)=O.NCCCNC(C1=CC=C(C=C1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(C=C2)F)=O.O1CCCC1.N1=CC=CC=C1>>C(C)(=O)NCCCNC(C1=CC=C(C=C1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(C=C2)F)=O | CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14](-[c:15]2[cH:16][n:17][c:18]3[cH:19][cH:20][c:21](-[c:22]4[cH:23][n:24]([C:25]([c:26]5[cH:27][cH:28][cH:29][cH:30][cH:31]5)([c:32]5[cH:33][cH:34][cH:35][cH:36][cH:37]5)[c:38]5[cH:39][cH:40][cH:41][cH:42][cH:43]5)[n:44... | CC(=O)OC(C)=O.NCCCNC(=O)c1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1 | CC(=O)NCCCNC(=O)c1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1 | null | null | O | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccc4)n3c2)cc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5]-[NH2;D1;+0:6]>>[C:4]-[C:5]-[NH;D2;+0:6]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | null | [] | null | null | 1 | HOUR | 0.014 mL acetic anhydride was added to a solution mixture of 50 mg N1-(3-aminopropyl)-4-{6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]imidazo[1,2-a]pyridin-3-yl}benzamide obtained in Example 43, 0.4 mL tetrahydrofuran and 0.2 mL pyridine under ice-cooling. The mixture was stirred at room temperature for 1 hour, water ... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccn2ccnc2c1.c1cn[nH]c1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | O | null | 1 | CC(=O)OC(C)=O.NCCCNC(=O)c1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1>O>CC(=O)NCCCNC(=O)c1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-896734599f244f34b0c84bd5a29ad4fd | Fc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(I)n3c2)cc1.NC(=O)c1ccc(Br)s1>>NC(=O)c1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)s1 | FC1=CC=C(C=C1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)I)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2.C(CCC)[Sn](CCCC)(CCCC)Cl.BrC1=CC=C(S1)C(=O)N>>FC1=CC=C(C=C1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)C2=CC=C(S2)C(=O)N)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2 | I[c:8]1[cH:9][n:10][c:11]2[cH:12][cH:13][c:14](-[c:15]3[cH:16][n:17]([C:18]([c:19]4[cH:20][cH:21][cH:22][cH:23][cH:24]4)([c:25]4[cH:26][cH:27][cH:28][cH:29][cH:30]4)[c:31]4[cH:32][cH:33][cH:34][cH:35][cH:36]4)[n:37][c:38]3-[c:39]3[cH:40][cH:41][c:42]([F:43])[cH:44][cH:45]3)[cH:46][n:47]12.Br[c:7]1[cH:6][cH:5][c:4]([C:2... | Fc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(I)n3c2)cc1.NC(=O)c1ccc(Br)s1 | NC(=O)c1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)s1 | null | null | C=1(C(=CC=CC1)C)C | C-C Coupling | Negishi | 3d61aa42036707a754960c0adf2ca7739fc8b9ab88b93eae61ee8ce326009e6a | a7a4ce9a92e2f8a62d28956a69a5cc384426ab72416e87d68c6a3feb23c22d66 | c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4cccs4)n3c2)cc1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](-[C:4](-[N;D1;H2:5])=[O;D1;H0:6]):[c:7]:[c:8]:1.I-[c;H0;D3;+0:9]1:[c:10]:[#7;a:11]:[c:12](:[c:13]):[#7;a:14]:1:[c:15]>>[N;D1;H2:5]-[C:4](=[O;D1;H0:6])-[c:3]1:[#16;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:9]2:[c:10]:[#7;a:11]:[c:12](:[c:13]):[#7;a:14]:2:[c:15]):[c:8]:[c:7]:1 | null | [] | 120 | CELSIUS | 2 | HOUR | A mixture of 200 mg 6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]-3-(1,1,1-tributylstannyl)imidazo[1,2-a]-pyridine prepared from 6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]-3-iodoimidazo[1,2-a]pyridine (compound in Production Example 39) and tributyltin chloride by the same method as in Production Example 48, 51 mg... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide | null | c1ccn2ccnc2c1.c1ccsc1 | c1ccsc1.c1ccn2ccnc2c1 | c1ccsc1.c1ccn2ccnc2c1.c1cn[nH]c1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | Br-.I- | C=1(C(=CC=CC1)C)C | 120 | 2 | Fc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(I)n3c2)cc1.NC(=O)c1ccc(Br)s1>C=1(C(=CC=CC1)C)C>NC(=O)c1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)s1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-136669f5a3144fd993ca58fd135d8a87 | CCC[CH2][Sn]([Cl])([CH2]CCC)[CH2]CCC.CN1CCN(c2cccc(Br)n2)CC1>>CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cccc(N2CCN(C)CC2)n1 | BrC1=CC=CC(=N1)N1CCN(CC1)C.C(CCC)[Sn](CCCC)(CCCC)Cl>>CN1CCN(CC1)C1=NC(=CC=C1)[Sn](CCCC)(CCCC)CCCC | [Cl][Sn:5]([CH2:4][CH2:3][CH2:2][CH3:1])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:10][CH2:11][CH2:12][CH3:13].Br[c:14]1[cH:15][cH:16][cH:17][c:18]([N:19]2[CH2:20][CH2:21][N:22]([CH3:23])[CH2:24][CH2:25]2)[n:26]1>>[CH3:1][CH2:2][CH2:3][CH2:4][Sn:5]([CH2:6][CH2:7][CH2:8][CH3:9])([CH2:10][CH2:11][CH2:12][CH3:13])[c:14]1[cH:15][c... | CCC[CH2][Sn]([Cl])([CH2]CCC)[CH2]CCC.CN1CCN(c2cccc(Br)n2)CC1 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cccc(N2CCN(C)CC2)n1 | null | null | null | Functional Group Interconversion | OtherReaction | 595ac0abb5e92435d058c6ee48fc895ec9c292bdbe417f57a54b9f065eff0354 | d9bf9bd3fc00efb5d713d9ac7f168986c2c94f1f455d32bdc9901567c1014c76 | c1ccc(N2CCNCC2)nc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[Sn;H0;D4;+0:8](-[Cl])(-[C:9]-[C:10])-[C:11]-[C:12]>>[C:6]-[C:7]-[Sn;H0;D4;+0:8](-[C:9]-[C:10])(-[C:11]-[C:12])-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | null | null | 190 mg 1-methyl-4-(6-tributylstannyl-2-pyridyl)-piperazine obtained from 1-(6-bromo-2-pyridyl)-4-methyl piperazine and tributyltin chloride by the same method as in Production Method 46 was reacted in the same manner as in Example 21 with 129 mg 6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]-3-iodoimidazo[1,2-a]pyridin... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | Tin | c1ccncc1 | c1ccncc1 | c1ccncc1.C1C[NH]CC[NH]1 | Br- | null | null | null | CCC[CH2][Sn]([Cl])([CH2]CCC)[CH2]CCC.CN1CCN(c2cccc(Br)n2)CC1>>CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cccc(N2CCN(C)CC2)n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5164d061d2834a26818985e1695dbc41 | COc1cccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)n1>>O=c1cccc(-c2cnc3ccc(-c4c[nH]nc4-c4ccc(F)cc4)cn23)[nH]1 | FC1=CC=C(C=C1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)C2=NC(=CC=C2)OC)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2.Br.[OH-].[Na+]>>FC1=CC=C(C=C1)C1=NNC=C1C=1C=CC=2N(C1)C(=CN2)C2=CC=CC(N2)=O | C[O:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[cH:8][n:9][c:10]3[cH:11][cH:12][c:13](-[c:14]4[cH:15][n:16](C(c5ccccc5)(c5ccccc5)c5ccccc5)[n:17][c:18]4-[c:19]4[cH:20][cH:21][c:22]([F:23])[cH:24][cH:25]4)[cH:26][n:27]23)[n:28]1>>[O:1]=[c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[cH:8][n:9][c:10]3[cH:11][cH:12][c:13](-[c:14]4[cH:15... | COc1cccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)n1 | O=c1cccc(-c2cnc3ccc(-c4c[nH]nc4-c4ccc(F)cc4)cn23)[nH]1 | null | null | C(C)(=O)O | Miscellaneous | OtherReaction | 57f3a3eebec0f02e9092974fdbfccc684b7275ffd27b1461457668ab7883bd0a | 291cad8b6dfbbd2c823b5c9d45efc37a166dc3454a9f151ac48cb357f4bc155f | O=c1cccc(-c2cnc3ccc(-c4c[nH]nc4-c4ccccc4)cn23)[nH]1 | C-[O;H0;D2;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[c:5]:[c:6](-[c:7](:[#7;a:8]):[c:9]:[#7;a:10]):[n;H0;D2;+0:11]:1.[#7;a:12]1:[c:13]:[c:14]:[c:15]:[n;H0;D3;+0:16]:1-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#7;a:12]1:[c:13]:[c:14]:[c:15]:[nH;D2;+0:16]:1.[#7;a:8]:[c:7](-[c:6]1:[c:5]:[c:4]:[c:3]:[c;H0;D3;+0:2](=[O;... | 16.9 | [{"value": 16.9, "product": "FC1=CC=C(C=C1)C1=NNC=C1C=1C=CC=2N(C1)C(=CN2)C2=CC=CC(N2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A mixture of 54 mg 6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]-3-(6-methoxy-2-pyridyl)imidazo[1,2-a]pyridine obtained in Example 23, 2 mL of 48% hydrobromic acid and 2 mL acetic acid was stirred at room temperature for 4 hours and then heated for 10 minutes under reflux. The reaction solution was cooled and neutrali... | 10.6084/m9.figshare.5104873.v1 | null | Ether | null | c1ccncc1.c1cn[nH]c1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccn1.c1cn[nH]c1 | c1ccccn1.c1ccn2ccnc2c1.c1cn[nH]c1.c1ccccc1 | Other | C(C)(=O)O | null | 4 | COc1cccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)n1>C(C)(=O)O>O=c1cccc(-c2cnc3ccc(-c4c[nH]nc4-c4ccc(F)cc4)cn23)[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-543c024e55e247aa8686db2a50819f6a | CS(=O)(=O)c1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4C(=O)O)cn23)s1.[NH4+]>>CS(=O)(=O)c1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4C(N)=O)cn23)s1 | CS(=O)(=O)C1=CC=C(S1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C(=O)O.Cl.C(C)N=C=NCCCN(C)C.[Cl-].[NH4+].C(C)N(CC)CC>>CS(=O)(=O)C1=CC=C(S1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C(=O)N | O[C:40]([c:39]1[c:16](-[c:15]2[cH:14][cH:13][c:12]3[n:11][cH:10][c:9](-[c:8]4[cH:7][cH:6][c:5]([S:2]([CH3:1])(=[O:3])=[O:4])[s:45]4)[n:44]3[cH:43]2)[cH:17][n:18]([C:19]([c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)([c:26]2[cH:27][cH:28][cH:29][cH:30][cH:31]2)[c:32]2[cH:33][cH:34][cH:35][cH:36][cH:37]2)[n:38]1)=[O:42].[N... | CS(=O)(=O)c1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4C(=O)O)cn23)s1.[NH4+] | CS(=O)(=O)c1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4C(N)=O)cn23)s1 | null | null | CN(C=O)C | Acylation | Carboxylic acid to amide conversion | 1283aef55d7ee699f097a8e5267689198c76ba671644401547f902657820236d | cb0a71c3fb37a76e96fbd81aae6f95a28398a03d1ad2c8e877085e735efb98f1 | c1ccc(C(c2ccccc2)(c2ccccc2)n2cc(-c3ccc4ncc(-c5cccs5)n4c3)cn2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[#7;a:5](-[C:6]):[c:7]:[c:8]:1.[NH4+;D0:9]>>[C:6]-[#7;a:5]1:[#7;a:4]:[c:3](-[C;H0;D3;+0:1](-[NH2;D1;+0:9])=[O;D1;H0:2]):[c:8]:[c:7]:1 | 55.1 | [{"value": 55.1, "product": "CS(=O)(=O)C1=CC=C(S1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of 40 mg 4-{3-[5-(methylsulfonyl)-2-thienyl]imidazo[1,2-a]pyridin-6-yl}-1-trityl-1H-3-pyrazole carboxylic acid, 37 mg 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride, 26 mg 1-oxybenzotriazole, 17 mg ammonium chloride, 0.077 mL triethylamine and 3 mL N,N-dimethylformamide was left overnight at roo... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | c1ccsc1.c1ccn2ccnc2c1.c1cn[nH]c1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | CN(C=O)C | null | 8 | CS(=O)(=O)c1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4C(=O)O)cn23)s1.[NH4+]>CN(C=O)C>CS(=O)(=O)c1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4C(N)=O)cn23)s1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ec86ff751bfe49ec8abc8dd454631803 | CCSc1nc2ccc(-c3cn(C(c4ccccc4)(c4ccccc4)c4ccccc4)nc3-c3ccc(F)cc3)cc2n1-c1ccc(F)cc1>>CCSc1nc2ccc(-c3c[nH]nc3-c3ccc(F)cc3)cc2n1-c1ccc(F)cc1.Cl | C(C)SC1=NC2=C(N1C1=CC=C(C=C1)F)C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(C=C2)F.Cl>>Cl.Cl.C(C)SC1=NC2=C(N1C1=CC=C(C=C1)F)C=C(C=C2)C=2C(=NNC2)C2=CC=C(C=C2)F | c1ccc(C(c2ccccc2)(c2ccccc2)[n:12]2[cH:11][c:10](-[c:9]3[cH:8][cH:7][c:6]4[n:5][c:4]([S:3][CH2:2][CH3:1])[n:24](-[c:25]5[cH:26][cH:27][c:28]([F:29])[cH:30][cH:31]5)[c:23]4[cH:22]3)[c:14](-[c:15]3[cH:16][cH:17][c:18]([F:19])[cH:20][cH:21]3)[n:13]2)cc1>>[CH3:1][CH2:2][S:3][c:4]1[n:5][c:6]2[cH:7][cH:8][c:9](-[c:10]3[cH:11]... | CCSc1nc2ccc(-c3cn(C(c4ccccc4)(c4ccccc4)c4ccccc4)nc3-c3ccc(F)cc3)cc2n1-c1ccc(F)cc1 | CCSc1nc2ccc(-c3c[nH]nc3-c3ccc(F)cc3)cc2n1-c1ccc(F)cc1.Cl | null | null | null | Functional Group Interconversion | OtherReaction | f8945b6c47d2fe181548474e648e16cfeefa7d5db2d97918e7510aa55a3c60d6 | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | c1ccc(-c2n[nH]cc2-c2ccc3ncn(-c4ccccc4)c3c2)cc1 | [#7;a:1]1:[c:2]:[c:3]:[c:4]:[n;H0;D3;+0:5]:1-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#7;a:1]1:[c:2]:[c:3]:[c:4]:[nH;D2;+0:5]:1 | null | [] | null | null | null | null | A solution mixture of 7.2 g 2-(ethylsulfanyl)-6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]-1H-benzo[d]imidazole obtained in Production Example 73, 3.5 g 4-fluorophenylboronic acid, 3.4 g copper (II) acetate, 2.0 mL pyridine, 4.6 g of 4 Å molecular sieves and 140 mL dichloromethane was stirred at room temperature for ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1cn[nH]c1 | c1cn[nH]c1 | c1ccc2[nH]cnc2c1.c1cn[nH]c1.c1ccccc1.c1ccccc1 | Other | null | null | null | CCSc1nc2ccc(-c3cn(C(c4ccccc4)(c4ccccc4)c4ccccc4)nc3-c3ccc(F)cc3)cc2n1-c1ccc(F)cc1>>CCSc1nc2ccc(-c3c[nH]nc3-c3ccc(F)cc3)cc2n1-c1ccc(F)cc1.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d201edef8d884917a5cf9d2b6e8988bb | CCS(=O)(=O)c1nc2ccc(-c3cn(C(c4ccccc4)(c4ccccc4)c4ccccc4)nc3-c3ccc(F)cc3)cc2n1-c1ccc(F)cc1>>COc1nc2ccc(-c3cn(C(c4ccccc4)(c4ccccc4)c4ccccc4)nc3-c3ccc(F)cc3)cc2n1-c1ccc(F)cc1 | C(C)S(=O)(=O)C1=NC2=C(N1C1=CC=C(C=C1)F)C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(C=C2)F.O.C(C)(=O)OCC.[H-].[Na+]>>FC1=CC=C(C=C1)N1C(=NC2=C1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(C=C2)F)OC | O=S(C[CH3:1])(=[O:2])[c:3]1[n:4][c:5]2[cH:6][cH:7][c:8](-[c:9]3[cH:10][n:11]([C:12]([c:13]4[cH:14][cH:15][cH:16][cH:17][cH:18]4)([c:19]4[cH:20][cH:21][cH:22][cH:23][cH:24]4)[c:25]4[cH:26][cH:27][cH:28][cH:29][cH:30]4)[n:31][c:32]3-[c:33]3[cH:34][cH:35][c:36]([F:37])[cH:38][cH:39]3)[cH:40][c:41]2[n:42]1-[c:43]1[cH:44][c... | CCS(=O)(=O)c1nc2ccc(-c3cn(C(c4ccccc4)(c4ccccc4)c4ccccc4)nc3-c3ccc(F)cc3)cc2n1-c1ccc(F)cc1 | COc1nc2ccc(-c3cn(C(c4ccccc4)(c4ccccc4)c4ccccc4)nc3-c3ccc(F)cc3)cc2n1-c1ccc(F)cc1 | null | null | O1CCCC1.CO | Miscellaneous | OtherReaction | 943d2963f13bae6123aa1b802d963bd23cf8da2c641cf7958e8f186dbc7cefb8 | 7a704b7b635b5a2792712202f58df48c6edd92c83bc73653aebcfab4358f37fa | c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncn(-c4ccccc4)c3c2)cc1 | O=S(=[O;H0;D1;+0:1])(-C-[CH3;D1;+0:2])-[c;H0;D3;+0:3]1:[#7;a:4]:[c:5]:[c:6]:[#7;a:7]:1-[c:8]>>[CH3;D1;+0:2]-[O;H0;D2;+0:1]-[c;H0;D3;+0:3]1:[#7;a:4]:[c:5]:[c:6]:[#7;a:7]:1-[c:8] | null | [] | null | null | null | null | 50 mg 2-(ethylsulfonyl)-1-(4-fluorophenyl)-6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]-1H-benzo[d]imidazole obtained in Example 138 was dissolved in 0.5 mL tetrahydrofuran and 3 mL methanol, then 28 mg sodium hydride was added thereto, and the mixture was heated for 3 hours under reflux under nitrogen atmosphere. Af... | 10.6084/m9.figshare.5104873.v1 | null | Sulfone | Ether | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1.c1cn[nH]c1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | O1CCCC1.CO | null | null | CCS(=O)(=O)c1nc2ccc(-c3cn(C(c4ccccc4)(c4ccccc4)c4ccccc4)nc3-c3ccc(F)cc3)cc2n1-c1ccc(F)cc1>O1CCCC1.CO>COc1nc2ccc(-c3cn(C(c4ccccc4)(c4ccccc4)c4ccccc4)nc3-c3ccc(F)cc3)cc2n1-c1ccc(F)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f2facef0fc7d47cfa2f2bb2ba67f9cbb | COc1nc2ccc(-c3c[nH]nc3-c3ccc(F)cc3)cc2n1-c1ccc(F)cc1>>Cl.Oc1nc2ccc(-c3c[nH]nc3-c3ccc(F)cc3)cc2n1-c1ccc(F)cc1 | FC1=CC=C(C=C1)N1C(=NC2=C1C=C(C=C2)C=2C(=NNC2)C2=CC=C(C=C2)F)OC.Cl.C(C)(=O)OCC>>Cl.Cl.FC1=CC=C(C=C1)N1C(=NC2=C1C=C(C=C2)C=2C(=NNC2)C2=CC=C(C=C2)F)O | C[O:3][c:4]1[n:5][c:6]2[cH:7][cH:8][c:9](-[c:10]3[cH:11][nH:12][n:13][c:14]3-[c:15]3[cH:16][cH:17][c:18]([F:19])[cH:20][cH:21]3)[cH:22][c:23]2[n:24]1-[c:25]1[cH:26][cH:27][c:28]([F:29])[cH:30][cH:31]1>>[ClH:2].[OH:3][c:4]1[n:5][c:6]2[cH:7][cH:8][c:9](-[c:10]3[cH:11][nH:12][n:13][c:14]3-[c:15]3[cH:16][cH:17][c:18]([F:19... | COc1nc2ccc(-c3c[nH]nc3-c3ccc(F)cc3)cc2n1-c1ccc(F)cc1 | Cl.Oc1nc2ccc(-c3c[nH]nc3-c3ccc(F)cc3)cc2n1-c1ccc(F)cc1 | null | null | CO | Functional Group Interconversion | Cleavage of methoxy ethers to alcohols | ca281afd6d837c7f54335da1f9ec9599389be19f9cfd143c483e4390084d9929 | fd883926c7ec011ca4a7b6ae0a1a6704668b3871fe0830f6768470d15ab35863 | c1ccc(-c2n[nH]cc2-c2ccc3ncn(-c4ccccc4)c3c2)cc1 | C-[O;H0;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[#7;a:6]:1-[c:7]>>[OH;D1;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[#7;a:6]:1-[c:7] | null | [] | null | null | null | null | 15 mg 1-(4-fluorophenyl)-6-[3-(4-fluorophenyl)-1H-4-pyrazolyl]-2-methoxy-1H-benzo [d] imidazole obtained in Example 139 was dissolved in methanol, then 2 mL of 4 N hydrochloric acid/ethyl acetate was added thereto, and the solvent was evaporated. The residue was crystallized from methanol/ether and then washed with eth... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccc2[nH]cnc2c1.c1cn[nH]c1.c1ccccc1.c1ccccc1 | null | CO | null | null | COc1nc2ccc(-c3c[nH]nc3-c3ccc(F)cc3)cc2n1-c1ccc(F)cc1>CO>Cl.Oc1nc2ccc(-c3c[nH]nc3-c3ccc(F)cc3)cc2n1-c1ccc(F)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8e0af78fa06349efb58c30d6665a5b1c | CCS(=O)(=O)c1nc2ccc(-c3cn(C(c4ccccc4)(c4ccccc4)c4ccccc4)nc3-c3ccc(F)cc3)cc2n1-c1ccc(F)cc1.NCc1ccccc1>>Fc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3nc(NCc4ccccc4)n(-c4ccc(F)cc4)c3c2)cc1 | C(C1=CC=CC=C1)N.C(C)S(=O)(=O)C1=NC2=C(N1C1=CC=C(C=C1)F)C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(C=C2)F>>C(C1=CC=CC=C1)NC1=NC2=C(N1C1=CC=C(C=C1)F)C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(C=C2)F | CCS(=O)(=O)[c:35]1[n:34][c:33]2[cH:32][cH:31][c:30](-[c:29]3[c:6](-[c:5]4[cH:4][cH:3][c:2]([F:1])[cH:55][cH:54]4)[n:7][n:8]([C:9]([c:10]4[cH:11][cH:12][cH:13][cH:14][cH:15]4)([c:16]4[cH:17][cH:18][cH:19][cH:20][cH:21]4)[c:22]4[cH:23][cH:24][cH:25][cH:26][cH:27]4)[cH:28]3)[cH:53][c:52]2[n:44]1-[c:45]1[cH:46][cH:47][c:48... | CCS(=O)(=O)c1nc2ccc(-c3cn(C(c4ccccc4)(c4ccccc4)c4ccccc4)nc3-c3ccc(F)cc3)cc2n1-c1ccc(F)cc1.NCc1ccccc1 | Fc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3nc(NCc4ccccc4)n(-c4ccc(F)cc4)c3c2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | bf5a8f040c1921c6a77342213d57051c5d0f84b395a4083cf97442509b3d3776 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | c1ccc(CNc2nc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccccc4)cc3n2-c2ccccc2)cc1 | C-C-S(=O)(=O)-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:1-[c:6].[NH2;D1;+0:7]-[C:8]-[c:9]>>[c:9]-[C:8]-[NH;D2;+0:7]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:1-[c:6] | null | [] | 150 | CELSIUS | 24 | HOUR | 1 mL benzyl amine was added to 40 mg 2-(ethylsulfonyl)-1-(4-fluorophenyl)-6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]-1H-benzo[d]imidazole obtained in Example 138, and then stirred at 150° C. for 24 hours. The reaction product was purified by silica gel chromatography (hexane/ethyl acetate) to give 26 mg N2-benzyl-1... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1 | c1ccccc1.c1c[nH]nc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2[nH]cnc2c1.c1ccccc1.c1ccccc1 | HO- | null | 150 | 24 | CCS(=O)(=O)c1nc2ccc(-c3cn(C(c4ccccc4)(c4ccccc4)c4ccccc4)nc3-c3ccc(F)cc3)cc2n1-c1ccc(F)cc1.NCc1ccccc1>>Fc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3nc(NCc4ccccc4)n(-c4ccc(F)cc4)c3c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f6bf2872e08f4d34b21a5120fce59da9 | CCS(=O)(=O)c1nc2ccc(-c3cn(C(c4ccccc4)(c4ccccc4)c4ccccc4)nc3-c3ccc(F)cc3)cc2n1-c1ccc(F)cc1.Cc1ncccc1O>>Cc1ncccc1Oc1nc2ccc(-c3cn(C(c4ccccc4)(c4ccccc4)c4ccccc4)nc3-c3ccc(F)cc3)cc2n1-c1ccc(F)cc1 | O.[H-].[Na+].C(C)S(=O)(=O)C1=NC2=C(N1C1=CC=C(C=C1)F)C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(C=C2)F.CC1=NC=CC=C1O>>FC1=CC=C(C=C1)N1C(=NC2=C1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(C=C2)F)OC=2C(=NC=CC2)C | CCS(=O)(=O)[c:9]1[n:10][c:11]2[cH:12][cH:13][c:14](-[c:15]3[cH:16][n:17]([C:18]([c:19]4[cH:20][cH:21][cH:22][cH:23][cH:24]4)([c:25]4[cH:26][cH:27][cH:28][cH:29][cH:30]4)[c:31]4[cH:32][cH:33][cH:34][cH:35][cH:36]4)[n:37][c:38]3-[c:39]3[cH:40][cH:41][c:42]([F:43])[cH:44][cH:45]3)[cH:46][c:47]2[n:48]1-[c:49]1[cH:50][cH:51... | CCS(=O)(=O)c1nc2ccc(-c3cn(C(c4ccccc4)(c4ccccc4)c4ccccc4)nc3-c3ccc(F)cc3)cc2n1-c1ccc(F)cc1.Cc1ncccc1O | Cc1ncccc1Oc1nc2ccc(-c3cn(C(c4ccccc4)(c4ccccc4)c4ccccc4)nc3-c3ccc(F)cc3)cc2n1-c1ccc(F)cc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | ce784a740a6490d0661f8d3c488672eed3d401019f1f96cc16ef39490bafcd02 | 5df75ac15caf6173d8206dd70d45a57321a6ccb2169690bfa04f02c58252d4f1 | c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3nc(Oc4cccnc4)n(-c4ccccc4)c3c2)cc1 | C-C-S(=O)(=O)-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:1-[c:6].[C;D1;H3:7]-[c:8](:[#7;a:9]:[c:10]):[c:11](-[OH;D1;+0:12]):[c:13]>>[C;D1;H3:7]-[c:8](:[#7;a:9]:[c:10]):[c:11](-[O;H0;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:1-[c:6]):[c:13] | null | [] | null | null | 20 | MINUTE | 40 mg 2-(ethylsulfonyl)-1-(4-fluorophenyl)-6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]-1H-benzo[d]imidazole obtained in Example 138 was dissolved in 2 mL N,N-dimethylformamide, then 6.8 mg sodium hydride was added thereto and stirred for 20 minutes, and 3 mL 2-methyl-3-pyridinol was added thereto and stirred at 80° ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Sulfone | Ether | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1 | c1ccncc1.c1ccc2[nH]cnc2c1.c1cn[nH]c1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | CN(C=O)C | null | 0.333333 | CCS(=O)(=O)c1nc2ccc(-c3cn(C(c4ccccc4)(c4ccccc4)c4ccccc4)nc3-c3ccc(F)cc3)cc2n1-c1ccc(F)cc1.Cc1ncccc1O>CN(C=O)C>Cc1ncccc1Oc1nc2ccc(-c3cn(C(c4ccccc4)(c4ccccc4)c4ccccc4)nc3-c3ccc(F)cc3)cc2n1-c1ccc(F)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c0e1d0e4a59f4295acd2db9dfad47ffc | CSc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncn(-c4ccc(C(N)=O)cn4)c3c2)cc1>>CS(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncn(-c4ccc(C(N)=O)cn4)c3c2)cc1 | S(=S)(=O)([O-])[O-].[Na+].[Na+].OOS(=O)[O-].[K+].CSC1=CC=C(C=C1)C1=NN(C=C1C=1C=CC2=C(N(C=N2)C2=NC=C(C(=O)N)C=C2)C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CSC1=CC=C(C=C1)C1=NN(C=C1C1=CC2=C(N(C=N2)C2=NC=C(C(=O)N)C=C2)C=C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.BrC=1C=CC2=C(N(C=N2)C2=NC=C(C(=O)N)C=C2)C1.BrC1=CC2=C(N(C=N2)... | [CH3:1][S:2][c:4]1[cH:5][cH:6][c:7](-[c:8]2[n:9][n:10]([C:11]([c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)([c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[c:24]3[cH:25][cH:26][cH:27][cH:28][cH:29]3)[cH:30][c:31]2-[c:32]2[cH:33][cH:34][c:35]3[n:36][cH:37][n:38](-[c:39]4[cH:40][cH:41][c:42]([C:43](=[O:3])[NH2:44])[cH:46][n:... | CSc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncn(-c4ccc(C(N)=O)cn4)c3c2)cc1 | CS(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncn(-c4ccc(C(N)=O)cn4)c3c2)cc1 | null | null | O1CCCC1.O.CO | Oxidation | Sulfanyl to sulfinyl | 29f9bfffa47040c72099618afef54fdb7408eeb2164b3ee44fc19259d57189bc | 0d8384798e99186622a84703631ad842e5f2f23e733bf981900c452ba16d76ee | c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncn(-c4ccccn4)c3c2)cc1 | [C;D1;H3:1]-[S;H0;D2;+0:2]-[c:3](:[c:4]):[c:5].[N;D1;H2:6]-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-[c:9](:[c:10]):[c:11]:[#7;a:12]:[c:13]>>[C;D1;H3:1]-[S;H0;D3;+0:2](=[O;H0;D1;+0:8])-[c:3](:[c:4]):[c:5].[N;D1;H2:6]-[C;H0;D3;+0:7](=[O;D1;H0:14])-[c:9](:[c:10]):[c:11]:[#7;a:12]:[c:13] | null | [] | null | null | 2 | HOUR | 0.2 g of the mixture of 6-(6-bromo-1H-benzo [d] imidazol-1-yl)nicotinic acid amide and 6-(5-bromo-1H-benzo [d] imidazol-1-yl)nicotinic acid amide as positional isomers in a ratio of 1:1, prepared from 5-bromo-1H-benzo[d]imidazole and 6-chloronicotinic acid amide by the same method as in Production Example 105, and 0.36... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide.Monosulfide | Primary amide.Sulfoxide | null | null | c1ccccc1.c1c[nH]nc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2[nH]cnc2c1.c1ccncc1 | null | O1CCCC1.O.CO | null | 2 | CSc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncn(-c4ccc(C(N)=O)cn4)c3c2)cc1>O1CCCC1.O.CO>CS(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncn(-c4ccc(C(N)=O)cn4)c3c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a36c3c8fa62e43eab30a7845e1565d40 | CSc1ccc(-c2ccnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4C)cc23)s1>>Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(-c3ccc(S(C)(=O)=O)s3)c2c1 | OOS(=O)[O-].[K+].OOS(=O)[O-].[K+].CSC1=CC=C(S1)C1=CC=NC2=CC=C(C=C12)C=1C(=NN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C.C([O-])(O)=O.[Na+].S(=S)(=O)([O-])[O-].[Na+].[Na+]>>CS(=O)(=O)C1=CC=C(S1)C1=CC=NC2=CC=C(C=C12)C=1C(=NN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C | [CH3:1][c:2]1[n:3][n:4]([C:5]([c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)([c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[cH:24][c:25]1-[c:26]1[cH:27][cH:28][c:29]2[n:30][cH:31][cH:32][c:33](-[c:34]3[cH:35][cH:36][c:37]([S:38][CH3:39])[s:42]3)[c:43]2[cH:44]1>>[CH3:1][c:2]1[n:3][n:4... | CSc1ccc(-c2ccnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4C)cc23)s1 | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(-c3ccc(S(C)(=O)=O)s3)c2c1 | null | null | O1CCCC1.O.C(C)(=O)OCC | Oxidation | OtherReaction | 20dd6d48007b4fe7cd760226f21413eb5e71e6468db112596c2e7ea4858c8ac1 | 5cedc1bf0f43f21d78a249521ecfcec19fc5ac4895c41eed0e84f0c2618149fa | c1ccc(C(c2ccccc2)(c2ccccc2)n2cc(-c3ccc4nccc(-c5cccs5)c4c3)cn2)cc1 | [C;D1;H3:1]-[S;H0;D2;+0:2]-[c:3](:[c:4]):[#16;a:5]:[c:6]>>[C;D1;H3:1]-[S;H0;D4;+0:2](=[O;D1;H0:7])(=[O;D1;H0:8])-[c:3](:[c:4]):[#16;a:5]:[c:6] | null | [] | null | null | 1 | HOUR | 1 mL aqueous solution of 86 mg oxone was added at room temperature to a solution of 67 mg 4-[5-(methylsulfanyl)-2-thienyl]-6-(3-methyl-1-trityl-1H-4-pyrazolyl)quinoline obtained in Example 155 in tetrahydrofuran, and the mixture was stirred for 1 hour. Further, 60 mg oxone was added thereto and stirred overnight. An aq... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfone | null | null | c1c[nH]nc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.c1ccsc1 | null | O1CCCC1.O.C(C)(=O)OCC | null | 1 | CSc1ccc(-c2ccnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4C)cc23)s1>O1CCCC1.O.C(C)(=O)OCC>Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(-c3ccc(S(C)(=O)=O)s3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-94404d995661477994379b6f2373c5b6 | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(-c3ccc(O)cc3)c2c1>>Cc1n[nH]cc1-c1ccc2nccc(-c3ccc(O)cc3)c2c1 | C([O-])(O)=O.[Na+].CC1=NN(C=C1C=1C=C2C(=CC=NC2=CC1)C1=CC=C(C=C1)O)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.Cl.[OH-].[Na+]>>CC1=NNC=C1C=1C=C2C(=CC=NC2=CC1)C1=CC=C(C=C1)O | c1ccc(C(c2ccccc2)(c2ccccc2)[n:4]2[n:3][c:2]([CH3:1])[c:6](-[c:7]3[cH:8][cH:9][c:10]4[n:11][cH:12][cH:13][c:14](-[c:15]5[cH:16][cH:17][c:18]([OH:19])[cH:20][cH:21]5)[c:22]4[cH:23]3)[cH:5]2)cc1>>[CH3:1][c:2]1[n:3][nH:4][cH:5][c:6]1-[c:7]1[cH:8][cH:9][c:10]2[n:11][cH:12][cH:13][c:14](-[c:15]3[cH:16][cH:17][c:18]([OH:19])[... | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(-c3ccc(O)cc3)c2c1 | Cc1n[nH]cc1-c1ccc2nccc(-c3ccc(O)cc3)c2c1 | null | null | O1CCCC1.O.CO.C(C)(=O)OCC | Deprotection | OtherReaction | 92b7543875cfe438a4c5cf3faf8e6c828b5eea356096f8ebdcd8d3241dc18933 | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | c1ccc(-c2ccnc3ccc(-c4cn[nH]c4)cc23)cc1 | [#7;a:1]1:[c:2]:[c:3]:[c:4]:[n;H0;D3;+0:5]:1-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#7;a:1]1:[c:2]:[c:3]:[c:4]:[nH;D2;+0:5]:1 | 76 | [{"value": 76.0, "product": "CC1=NNC=C1C=1C=C2C(=CC=NC2=CC1)C1=CC=C(C=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of 9.5 mg 4-[6-(3-methyl-1-trityl-1H-4-pyrazolyl)-4-quinolyl]phenol obtained in Example 153, 0.13 mL of 5 N hydrochloric acid, 1 mL tetrahydrofuran, and 1 mL methanol was stirred overnight at room temperature. The reaction solution was cooled and then neutralized with 2 N aqueous sodium hydroxide and an aqueo... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1cn[nH]c1 | c1cn[nH]c1 | c1cn[nH]c1.c1ccc2ncccc2c1.c1ccccc1 | Other | O1CCCC1.O.CO.C(C)(=O)OCC | null | 8 | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(-c3ccc(O)cc3)c2c1>O1CCCC1.O.CO.C(C)(=O)OCC>Cc1n[nH]cc1-c1ccc2nccc(-c3ccc(O)cc3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-af1ed52550ec4c7c9bccbce765ce14d9 | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(-c3ccccn3)c2c1>>Cc1n[nH]cc1-c1ccc2nccc(-c3ccccn3)c2c1.Cl | [OH-].[Na+].CC1=NN(C=C1C=1C=C2C(=CC=NC2=CC1)C1=NC=CC=C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.Cl.O1CCCC1>>Cl.Cl.CC1=NNC=C1C=1C=C2C(=CC=NC2=CC1)C1=NC=CC=C1 | c1ccc(C(c2ccccc2)(c2ccccc2)[n:4]2[n:3][c:2]([CH3:1])[c:6](-[c:7]3[cH:8][cH:9][c:10]4[n:11][cH:12][cH:13][c:14](-[c:15]5[cH:16][cH:17][cH:18][cH:19][n:20]5)[c:21]4[cH:22]3)[cH:5]2)cc1>>[CH3:1][c:2]1[n:3][nH:4][cH:5][c:6]1-[c:7]1[cH:8][cH:9][c:10]2[n:11][cH:12][cH:13][c:14](-[c:15]3[cH:16][cH:17][cH:18][cH:19][n:20]3)[c:... | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(-c3ccccn3)c2c1 | Cc1n[nH]cc1-c1ccc2nccc(-c3ccccn3)c2c1.Cl | null | null | O.CO.C(C)(=O)OCC | Functional Group Interconversion | OtherReaction | f8945b6c47d2fe181548474e648e16cfeefa7d5db2d97918e7510aa55a3c60d6 | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | c1ccc(-c2ccnc3ccc(-c4cn[nH]c4)cc23)nc1 | [#7;a:1]1:[c:2]:[c:3]:[c:4]:[n;H0;D3;+0:5]:1-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#7;a:1]1:[c:2]:[c:3]:[c:4]:[nH;D2;+0:5]:1 | null | [] | null | null | 8 | HOUR | A mixture of 33 mg 6-(3-methyl-1-trityl-1H-pyrazolyl)-4-(2-pyridyl)quinoline obtained in Example 154, 0.48 mL of 5 N hydrochloric acid, 3 mL tetrahydrofuran, and 3 mL methanol was stirred overnight at room temperature. The reaction solution was cooled with iced water and basified with 5N aqueous sodium hydroxide, then ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1cn[nH]c1 | c1cn[nH]c1 | c1cn[nH]c1.c1ccc2ncccc2c1.c1ccncc1 | Other | O.CO.C(C)(=O)OCC | null | 8 | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(-c3ccccn3)c2c1>O.CO.C(C)(=O)OCC>Cc1n[nH]cc1-c1ccc2nccc(-c3ccccn3)c2c1.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-edb59f1adaa647fa87ca9cb6a0dd350f | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(-c3ccc(S(C)(=O)=O)s3)c2c1.ClCCl>>Cc1n[nH]cc1-c1ccc2nccc(-c3ccc(S(C)(=O)=O)s3)c2c1.Cl | [OH-].[Na+].CS(=O)(=O)C1=CC=C(S1)C1=CC=NC2=CC=C(C=C12)C=1C(=NN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C.FC(C(=O)O)(F)F.ClCCl>>Cl.CC1=NNC=C1C=1C=C2C(=CC=NC2=CC1)C=1SC(=CC1)S(=O)(=O)C | c1ccc(C(c2ccccc2)(c2ccccc2)[n:4]2[n:3][c:2]([CH3:1])[c:6](-[c:7]3[cH:8][cH:9][c:10]4[n:11][cH:12][cH:13][c:14](-[c:15]5[cH:16][cH:17][c:18]([S:19]([CH3:20])(=[O:21])=[O:22])[s:23]5)[c:24]4[cH:25]3)[cH:5]2)cc1.ClC[Cl:26]>>[CH3:1][c:2]1[n:3][nH:4][cH:5][c:6]1-[c:7]1[cH:8][cH:9][c:10]2[n:11][cH:12][cH:13][c:14](-[c:15]3[c... | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(-c3ccc(S(C)(=O)=O)s3)c2c1.ClCCl | Cc1n[nH]cc1-c1ccc2nccc(-c3ccc(S(C)(=O)=O)s3)c2c1.Cl | null | null | O.C(C)(=O)OCC | Miscellaneous | OtherReaction | fb44b82bd181fddf36fd45bbc4bb51cbf1867a3abca895408058755e68302696 | 65e22ac5ac73e4dc94c17b99f93076354fa5a281d80003bd5a6c5af277cafff7 | c1csc(-c2ccnc3ccc(-c4cn[nH]c4)cc23)c1 | Cl-C-[Cl;H0;D1;+0:1].[#7;a:2]1:[c:3]:[c:4]:[c:5]:[n;H0;D3;+0:6]:1-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#7;a:2]1:[c:3]:[c:4]:[c:5]:[nH;D2;+0:6]:1.[ClH;D0;+0:1] | null | [] | null | null | 8 | HOUR | A mixture of 33 mg 4-[5-(methylsulfonyl)-2-thienyl]-6-(3-methyl-1-trityl-1H-4-pyrazolyl)quinoline obtained in Example 156, 0.5 mL trifluoroacetic acid and 2 mL dichloromethane was stirred overnight at room temperature. The reaction solution was cooled with iced water and basified with 5 N aqueous sodium hydroxide, then... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide | null | c1ccccc1.c1ccccc1.c1ccccc1.c1cn[nH]c1 | c1cn[nH]c1 | c1cn[nH]c1.c1ccc2ncccc2c1.c1ccsc1 | HCl | O.C(C)(=O)OCC | null | 8 | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(-c3ccc(S(C)(=O)=O)s3)c2c1.ClCCl>O.C(C)(=O)OCC>Cc1n[nH]cc1-c1ccc2nccc(-c3ccc(S(C)(=O)=O)s3)c2c1.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8e9681b48a2a4fe0a4a041faf7fe326a | CS(=O)(=O)c1ccc(-c2ccnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4C(F)(F)F)cc23)s1>>CS(=O)(=O)c1ccc(-c2ccnc3ccc(-c4c[nH]nc4C(F)(F)F)cc23)s1 | [OH-].[Na+].CS(=O)(=O)C1=CC=C(S1)C1=CC=NC2=CC=C(C=C12)C=1C(=NN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C(F)(F)F.FC(C(=O)O)(F)F.ClCCl>>CS(=O)(=O)C1=CC=C(S1)C1=CC=NC2=CC=C(C=C12)C=1C(=NNC1)C(F)(F)F | c1ccc(C(c2ccccc2)(c2ccccc2)[n:19]2[cH:18][c:17](-[c:16]3[cH:15][cH:14][c:13]4[n:12][cH:11][cH:10][c:9](-[c:8]5[cH:7][cH:6][c:5]([S:2]([CH3:1])(=[O:3])=[O:4])[s:28]5)[c:27]4[cH:26]3)[c:21]([C:22]([F:23])([F:24])[F:25])[n:20]2)cc1>>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][n:12][c:13]3[cH:... | CS(=O)(=O)c1ccc(-c2ccnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4C(F)(F)F)cc23)s1 | CS(=O)(=O)c1ccc(-c2ccnc3ccc(-c4c[nH]nc4C(F)(F)F)cc23)s1 | null | null | O.C(C)(=O)OCC | Deprotection | OtherReaction | 92b7543875cfe438a4c5cf3faf8e6c828b5eea356096f8ebdcd8d3241dc18933 | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | c1csc(-c2ccnc3ccc(-c4cn[nH]c4)cc23)c1 | [#7;a:1]1:[c:2]:[c:3]:[c:4]:[n;H0;D3;+0:5]:1-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#7;a:1]1:[c:2]:[c:3]:[c:4]:[nH;D2;+0:5]:1 | 48.8 | [{"value": 48.8, "product": "CS(=O)(=O)C1=CC=C(S1)C1=CC=NC2=CC=C(C=C12)C=1C(=NNC1)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of 58 mg 4-(5-methylsulfonyl 2-thienyl)-6-(3-trifluoromethyl-1-trityl-1H-4-pyrazolyl)qui noline obtained in Example 158, 1 mL trifluoroacetic acid and 3 mL dichloromethane was stirred overnight at room temperature. The reaction solution was cooled with iced water and basified with 5 N aqueous sodium hydroxide... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1cn[nH]c1 | c1cn[nH]c1 | c1ccsc1.c1ccc2ncccc2c1.c1cn[nH]c1 | Other | O.C(C)(=O)OCC | null | 8 | CS(=O)(=O)c1ccc(-c2ccnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4C(F)(F)F)cc23)s1>O.C(C)(=O)OCC>CS(=O)(=O)c1ccc(-c2ccnc3ccc(-c4c[nH]nc4C(F)(F)F)cc23)s1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3181d23a9dd14fb98bb8fba7495710e3 | Fc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3nccc(-c4ccccn4)c3c2)cc1>>Fc1ccc(-c2n[nH]cc2-c2ccc3nccc(-c4ccccn4)c3c2)cc1 | FC1=CC=C(C=C1)C1=NN(C=C1C=1C=C2C(=CC=NC2=CC1)C1=NC=CC=C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.Cl>>FC1=CC=C(C=C1)C1=NNC=C1C=1C=C2C(=CC=NC2=CC1)C1=NC=CC=C1 | c1ccc(C(c2ccccc2)(c2ccccc2)[n:8]2[n:7][c:6](-[c:5]3[cH:4][cH:3][c:2]([F:1])[cH:28][cH:27]3)[c:10](-[c:11]3[cH:12][cH:13][c:14]4[n:15][cH:16][cH:17][c:18](-[c:19]5[cH:20][cH:21][cH:22][cH:23][n:24]5)[c:25]4[cH:26]3)[cH:9]2)cc1>>[F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][nH:8][cH:9][c:10]2-[c:11]2[cH:12][cH:13][c:14]3[n:1... | Fc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3nccc(-c4ccccn4)c3c2)cc1 | Fc1ccc(-c2n[nH]cc2-c2ccc3nccc(-c4ccccn4)c3c2)cc1 | null | null | null | Deprotection | OtherReaction | 92b7543875cfe438a4c5cf3faf8e6c828b5eea356096f8ebdcd8d3241dc18933 | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | c1ccc(-c2n[nH]cc2-c2ccc3nccc(-c4ccccn4)c3c2)cc1 | [#7;a:1]1:[c:2]:[c:3]:[c:4]:[n;H0;D3;+0:5]:1-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#7;a:1]1:[c:2]:[c:3]:[c:4]:[nH;D2;+0:5]:1 | 52.7 | [{"value": 52.7, "product": "FC1=CC=C(C=C1)C1=NNC=C1C=1C=C2C(=CC=NC2=CC1)C1=NC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 63 mg 6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]-4-(2-pyridyl)quinoline obtained in Example 159 and 0.82 mL of 5 N hydrochloric acid were reacted in the same manner as in Example 162, to give 20 mg of the title compound as a colorless amorphous.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1cn[nH]c1 | c1cn[nH]c1 | c1ccccc1.c1cn[nH]c1.c1ccc2ncccc2c1.c1ccncc1 | Other | null | null | null | Fc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3nccc(-c4ccccn4)c3c2)cc1>>Fc1ccc(-c2n[nH]cc2-c2ccc3nccc(-c4ccccn4)c3c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-95ef89c048094408b4b9ce7fb4060e93 | CS(=O)(=O)c1ccc(-c2ccnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cc23)s1>>CS(=O)(=O)c1ccc(-c2ccnc3ccc(-c4c[nH]nc4-c4ccc(F)cc4)cc23)s1 | FC1=CC=C(C=C1)C1=NN(C=C1C=1C=C2C(=CC=NC2=CC1)C=1SC(=CC1)S(=O)(=O)C)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.FC(C(=O)O)(F)F>>FC1=CC=C(C=C1)C1=NNC=C1C=1C=C2C(=CC=NC2=CC1)C=1SC(=CC1)S(=O)(=O)C | c1ccc(C(c2ccccc2)(c2ccccc2)[n:19]2[cH:18][c:17](-[c:16]3[cH:15][cH:14][c:13]4[n:12][cH:11][cH:10][c:9](-[c:8]5[cH:7][cH:6][c:5]([S:2]([CH3:1])(=[O:3])=[O:4])[s:31]5)[c:30]4[cH:29]3)[c:21](-[c:22]3[cH:23][cH:24][c:25]([F:26])[cH:27][cH:28]3)[n:20]2)cc1>>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][... | CS(=O)(=O)c1ccc(-c2ccnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cc23)s1 | CS(=O)(=O)c1ccc(-c2ccnc3ccc(-c4c[nH]nc4-c4ccc(F)cc4)cc23)s1 | null | null | null | Deprotection | OtherReaction | 92b7543875cfe438a4c5cf3faf8e6c828b5eea356096f8ebdcd8d3241dc18933 | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | c1ccc(-c2n[nH]cc2-c2ccc3nccc(-c4cccs4)c3c2)cc1 | [#7;a:1]1:[c:2]:[c:3]:[c:4]:[n;H0;D3;+0:5]:1-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#7;a:1]1:[c:2]:[c:3]:[c:4]:[nH;D2;+0:5]:1 | 55.2 | [{"value": 55.2, "product": "FC1=CC=C(C=C1)C1=NNC=C1C=1C=C2C(=CC=NC2=CC1)C=1SC(=CC1)S(=O)(=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 39 mg 6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]-4-(5-methylsulfonyl 2-thienyl)quinoline obtained in Example 167 and 0.5 mL trifluoroacetic acid were reacted in the same manner as in Example 165, to give 14 mg of the title compound as pale yellow crystals.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1cn[nH]c1 | c1cn[nH]c1 | c1ccsc1.c1ccc2ncccc2c1.c1cn[nH]c1.c1ccccc1 | Other | null | null | null | CS(=O)(=O)c1ccc(-c2ccnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cc23)s1>>CS(=O)(=O)c1ccc(-c2ccnc3ccc(-c4c[nH]nc4-c4ccc(F)cc4)cc23)s1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-83099ed2ec08478b8244911b8743b6fd | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCNCC3)c2c1.NS(N)(=O)=O>>Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3C=CN(S(N)(=O)=O)C=C3)c2c1 | CC1=NN(C=C1C=1C=C2C(=CC=NC2=CC1)N1CCNCC1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.S(=O)(=O)(N)N>>CC1=NN(C=C1C=1C=C2C(=CC=NC2=CC1)N1C=CN(C=C1)S(=O)(=O)N)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | [CH3:1][c:2]1[n:3][n:4]([C:5]([c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)([c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[cH:24][c:25]1-[c:26]1[cH:27][cH:28][c:29]2[n:30][cH:31][cH:32][c:33]([N:34]3[CH2:35][CH2:36][NH:37][CH2:42][CH2:43]3)[c:44]2[cH:45]1.N[S:38]([NH2:39])(=[O:40])=... | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCNCC3)c2c1.NS(N)(=O)=O | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3C=CN(S(N)(=O)=O)C=C3)c2c1 | null | null | O1CCOCC1 | Miscellaneous | OtherReaction | ae329cb099decbcefe7e32bde860b8e1a84134f974a853791f55581fe5c15c93 | 2945f125abdcdcdf3f7aba64afb45e89ccc08b097f9c3ec192eb9ea89b3eabdb | C1=CN(c2ccnc3ccc(-c4cnn(C(c5ccccc5)(c5ccccc5)c5ccccc5)c4)cc23)C=CN1 | N-[S;H0;D4;+0:1](-[N;D1;H2:2])(=[O;D1;H0:3])=[O;D1;H0:4].[c:5]-[#7:6]1-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[NH;D2;+0:9]-[CH2;D2;+0:10]-[CH2;D2;+0:11]-1>>[N;D1;H2:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[N;H0;D3;+0:9]1-[CH;D2;+0:8]=[CH;D2;+0:7]-[#7:6](-[c:5])-[CH;D2;+0:11]=[CH;D2;+0:10]-1 | 73.1 | [{"value": 73.1, "product": "CC1=NN(C=C1C=1C=C2C(=CC=NC2=CC1)N1C=CN(C=C1)S(=O)(=O)N)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 54 mg 6-(3-methyl-1-trityl-1H-4-pyrazolyl)-4-piperazin-1-yl-quinoline obtained in Example 187, 96 mg sulfamide, and 5 mL dioxane was heated for 4 hours under reflux. The reaction solution was evaporated, then ethyl acetate and water were added to the residue, and the organic layer was separated, then washe... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Sulfonamide.Secondary amine | Enamine.Enamine.Enamine.Sulfonamide | C1C[NH]CCN1 | C1=C[NH]C=C[NH]1 | c1c[nH]nc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.C1=C[NH]C=C[NH]1 | Other | O1CCOCC1 | null | null | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCNCC3)c2c1.NS(N)(=O)=O>O1CCOCC1>Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3C=CN(S(N)(=O)=O)C=C3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7a8d08b950614f38a4875328e9f0b75e | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCNCC3)c2c1.NC(=O)CCl>>Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(CC(N)=O)CC3)c2c1 | CC1=NN(C=C1C=1C=C2C(=CC=NC2=CC1)N1CCNCC1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.ClCC(=O)N.C([O-])([O-])=O.[K+].[K+].CN(C=O)C.ClCC(=O)N>>CC1=NN(C=C1C=1C=C2C(=CC=NC2=CC1)N1CCN(CC1)CC(=O)N)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | [CH3:1][c:2]1[n:3][n:4]([C:5]([c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)([c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[cH:24][c:25]1-[c:26]1[cH:27][cH:28][c:29]2[n:30][cH:31][cH:32][c:33]([N:34]3[CH2:35][CH2:36][NH:37][CH2:42][CH2:43]3)[c:44]2[cH:45]1.Cl[CH2:38][C:39]([NH2:40])=... | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCNCC3)c2c1.NC(=O)CCl | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(CC(N)=O)CC3)c2c1 | null | null | O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b703623ddc3b029d4716c15f5414f41773434bcc7e3f3853faf62273596bed77 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(C(c2ccccc2)(c2ccccc2)n2cc(-c3ccc4nccc(N5CCNCC5)c4c3)cn2)cc1 | Cl-[CH2;D2;+0:1]-[C:2](-[N;D1;H2:3])=[O;D1;H0:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[N;D1;H2:3]-[C:2](=[O;D1;H0:4])-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#7:5]-[C:10]-[C:9]-1 | 68.8 | [{"value": 68.8, "product": "CC1=NN(C=C1C=1C=C2C(=CC=NC2=CC1)N1CCN(CC1)CC(=O)N)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 115 | CELSIUS | 5 | HOUR | A mixture of 54 mg 6-(3-methyl-1-trityl-1H-4-pyrazolyl)-4-piperazin-1-yl-quinoline obtained in Example 187, 9.4 mg 2-chloroacetamide, 16 mg potassium carbonate and 3 mL dimethylformamide was stirred at 115° C. for 5 hours. 3 mg of 2-chloroacetamide was added thereto, and the mixture was stirred at the same temperature ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | c1c[nH]nc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.C1C[NH]CC[NH]1 | HCl | O.C(C)(=O)OCC | 115 | 5 | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCNCC3)c2c1.NC(=O)CCl>O.C(C)(=O)OCC>Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(CC(N)=O)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-888c2a221b0c44a3928bacdd8dce1ae0 | CN(C)C(=O)CCl.Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCNCC3)c2c1>>Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(CC(=O)N(C)C)CC3)c2c1 | CC1=NN(C=C1C=1C=C2C(=CC=NC2=CC1)N1CCNCC1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CN(C(CCl)=O)C>>CN(C(CN1CCN(CC1)C1=CC=NC2=CC=C(C=C12)C=1C(=NN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C)=O)C | Cl[CH2:38][C:39](=[O:40])[N:41]([CH3:42])[CH3:43].[CH3:1][c:2]1[n:3][n:4]([C:5]([c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)([c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[cH:24][c:25]1-[c:26]1[cH:27][cH:28][c:29]2[n:30][cH:31][cH:32][c:33]([N:34]3[CH2:35][CH2:36][NH:37][CH2:44][CH... | CN(C)C(=O)CCl.Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCNCC3)c2c1 | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(CC(=O)N(C)C)CC3)c2c1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b703623ddc3b029d4716c15f5414f41773434bcc7e3f3853faf62273596bed77 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(C(c2ccccc2)(c2ccccc2)n2cc(-c3ccc4nccc(N5CCNCC5)c4c3)cn2)cc1 | Cl-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[C;D1;H3:5])-[C;D1;H3:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[C;D1;H3:5]-[#7:4](-[C;D1;H3:6])-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1 | 90.6 | [{"value": 90.6, "product": "CN(C(CN1CCN(CC1)C1=CC=NC2=CC=C(C=C12)C=1C(=NN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 80 mg 6-(3-methyl-1-trityl-1H-4-pyrazolyl)-4-piperazin-1-yl-quinoline obtained in Example 187 and 27 mg N,N-dimethyl-2-chloroacetamide were reacted in the same manner as in Example 190, to give 84 mg of the title compound as a pale yellow amorphous.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | c1c[nH]nc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.C1C[NH]CC[NH]1 | HCl | null | null | null | CN(C)C(=O)CCl.Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCNCC3)c2c1>>Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(CC(=O)N(C)C)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f00ccef1a08c41548613b5663786598e | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCNCC3)c2c1.O=C1c2ccccc2C(=O)N1CCBr>>Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(CCN4C(=O)c5ccccc5C4=O)CC3)c2c1 | CC1=NN(C=C1C=1C=C2C(=CC=NC2=CC1)N1CCNCC1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.BrCCN1C(C=2C(C1=O)=CC=CC2)=O.C([O-])([O-])=O.[Na+].[Na+].C(C)#N>>CC1=NN(C=C1C=1C=C2C(=CC=NC2=CC1)N1CCN(CC1)CCN1C(C=2C(C1=O)=CC=CC2)=O)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2 | [CH3:1][c:2]1[n:3][n:4]([C:5]([c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)([c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[cH:24][c:25]1-[c:26]1[cH:27][cH:28][c:29]2[n:30][cH:31][cH:32][c:33]([N:34]3[CH2:35][CH2:36][NH:37][CH2:51][CH2:52]3)[c:53]2[cH:54]1.Br[CH2:38][CH2:39][N:40]1[C... | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCNCC3)c2c1.O=C1c2ccccc2C(=O)N1CCBr | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(CCN4C(=O)c5ccccc5C4=O)CC3)c2c1 | null | null | O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b703623ddc3b029d4716c15f5414f41773434bcc7e3f3853faf62273596bed77 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1c2ccccc2C(=O)N1CCN1CCN(c2ccnc3ccc(-c4cnn(C(c5ccccc5)(c5ccccc5)c5ccccc5)c4)cc23)CC1 | Br-[CH2;D2;+0:1]-[C:2]-[#7:3](-[C:4]=[O;D1;H0:5])-[C:6]=[O;D1;H0:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[O;D1;H0:5]=[C:4]-[#7:3](-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#7:8]-[C:13]-[C:12]-1)-[C:6]=[O;D1;H0:7] | 57.6 | [{"value": 57.6, "product": "CC1=NN(C=C1C=1C=C2C(=CC=NC2=CC1)N1CCN(CC1)CCN1C(C=2C(C1=O)=CC=CC2)=O)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 80 mg 6-(3-methyl-1-trityl-1H-4-pyrazolyl)-4-piperazin-1-yl-quinoline obtained in Example 187, 46 mg N-(2-bromoethyl)phthalimide, 19 mg sodium carbonate, and 8 mL acetonitrile was heated overnight under reflux. Ethyl acetate and water were added to the reaction solution, and the organic layer was separated... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | c1c[nH]nc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.C1C[NH]CC[NH]1.c1ccc2c(c1)C[NH]C2 | HBr | O.C(C)(=O)OCC | null | null | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCNCC3)c2c1.O=C1c2ccccc2C(=O)N1CCBr>O.C(C)(=O)OCC>Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(CCN4C(=O)c5ccccc5C4=O)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5227e25de751439ba43db5c57969150f | FC(F)(F)c1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCNCC3)c2c1.O=C(Cl)N1CCOCC1>>O=C(N1CCOCC1)N1CCN(c2ccnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4C(F)(F)F)cc23)CC1 | N1(CCNCC1)C1=CC=NC2=CC=C(C=C12)C=1C(=NN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C(F)(F)F.C(C)N(CC)CC.C(C)(=O)OCC.N1(CCOCC1)C(=O)Cl>>O1CCN(CC1)C(=O)N1CCN(CC1)C1=CC=NC2=CC=C(C=C12)C=1C(=NN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C(F)(F)F | [NH:9]1[CH2:10][CH2:11][N:12]([c:13]2[cH:14][cH:15][n:16][c:17]3[cH:18][cH:19][c:20](-[c:21]4[cH:22][n:23]([C:24]([c:25]5[cH:26][cH:27][cH:28][cH:29][cH:30]5)([c:31]5[cH:32][cH:33][cH:34][cH:35][cH:36]5)[c:37]5[cH:38][cH:39][cH:40][cH:41][cH:42]5)[n:43][c:44]4[C:45]([F:46])([F:47])[F:48])[cH:49][c:50]23)[CH2:51][CH2:52... | FC(F)(F)c1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCNCC3)c2c1.O=C(Cl)N1CCOCC1 | O=C(N1CCOCC1)N1CCN(c2ccnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4C(F)(F)F)cc23)CC1 | null | null | ClCCl.O | Acylation | N-alkylation of secondary amines with alkyl halides | 9f480cf7d56f704fd9b7f19410e93a0b335ca09273ad87dbe310c5462f719bdc | 353c6e1db25433862a8bcf26ca332f6abeb45cb685806584bc65f8cfcb712540 | O=C(N1CCOCC1)N1CCN(c2ccnc3ccc(-c4cnn(C(c5ccccc5)(c5ccccc5)c5ccccc5)c4)cc23)CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C:4])-[C:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[C:4]-[#7:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1)-[C:5] | null | [] | null | null | 8 | HOUR | While a solution of 118 mg 4-piperazin-1-yl-6-[3-(trifluoromethyl)-1-trityl-1H-4-pyrazolyl]quinoline obtained in Example 188 and 61 mg triethylamine in dichloromethane was stirred under ice-cooling in a stream of nitrogen, 35 μL 4-morpholine carbonyl chloride was added thereto, and the mixture was stirred overnight at ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amide.Secondary amine | Urea | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1COCC[NH]1.C1C[NH]CC[NH]1.c1ccc2ncccc2c1.c1cn[nH]c1.c1ccccc1.c1ccccc1.c1ccccc1 | HCl | ClCCl.O | null | 8 | FC(F)(F)c1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCNCC3)c2c1.O=C(Cl)N1CCOCC1>ClCCl.O>O=C(N1CCOCC1)N1CCN(c2ccnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4C(F)(F)F)cc23)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-668dc14ba70349838cac034d9938ccbf | FC(F)(F)c1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCNCC3)c2c1.O=C(Cl)N1CCCC1>>O=C(N1CCCC1)N1CCN(c2ccnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4C(F)(F)F)cc23)CC1 | N1(CCNCC1)C1=CC=NC2=CC=C(C=C12)C=1C(=NN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C(F)(F)F.N1(CCCC1)C(=O)Cl>>N1(CCCC1)C(=O)N1CCN(CC1)C1=CC=NC2=CC=C(C=C12)C=1C(=NN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C(F)(F)F | [NH:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][cH:14][n:15][c:16]3[cH:17][cH:18][c:19](-[c:20]4[cH:21][n:22]([C:23]([c:24]5[cH:25][cH:26][cH:27][cH:28][cH:29]5)([c:30]5[cH:31][cH:32][cH:33][cH:34][cH:35]5)[c:36]5[cH:37][cH:38][cH:39][cH:40][cH:41]5)[n:42][c:43]4[C:44]([F:45])([F:46])[F:47])[cH:48][c:49]23)[CH2:50][CH2:51]... | FC(F)(F)c1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCNCC3)c2c1.O=C(Cl)N1CCCC1 | O=C(N1CCCC1)N1CCN(c2ccnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4C(F)(F)F)cc23)CC1 | null | null | null | Acylation | N-alkylation of secondary amines with alkyl halides | 9f480cf7d56f704fd9b7f19410e93a0b335ca09273ad87dbe310c5462f719bdc | 353c6e1db25433862a8bcf26ca332f6abeb45cb685806584bc65f8cfcb712540 | O=C(N1CCCC1)N1CCN(c2ccnc3ccc(-c4cnn(C(c5ccccc5)(c5ccccc5)c5ccccc5)c4)cc23)CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C:4])-[C:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[C:4]-[#7:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:9]1-[C:10]-[C:11]-[#7:6]-[C:7]-[C:8]-1)-[C:5] | null | [] | null | null | null | null | 118 mg 4-piperazin-1-yl-6-(3-trifluoromethyl-1-trityl-1H-4-pyrazolyl)quinoline obtained in Example 188 and 33 μL 1-pyrrolidine carbonyl chloride were reacted in the same manner as in Example 193, to give 126 mg of the title compound as a colorless amorphous.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amide.Secondary amine | Urea | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1CC[NH]C1.C1C[NH]CC[NH]1.c1ccc2ncccc2c1.c1cn[nH]c1.c1ccccc1.c1ccccc1.c1ccccc1 | HCl | null | null | null | FC(F)(F)c1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCNCC3)c2c1.O=C(Cl)N1CCCC1>>O=C(N1CCCC1)N1CCN(c2ccnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4C(F)(F)F)cc23)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b803d90731a84642baa04a272586fc69 | C1COCCN1.Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(C(=O)n4ccnc4)CC3)c2c1>>Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(C(=O)N4CCOCC4)CC3)c2c1 | N1(C=NC=C1)C(=O)N1CCN(CC1)C1=CC=NC2=CC=C(C=C12)C=1C(=NN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C.N1CCOCC1.C(C)(=O)OCC>>CC1=NN(C=C1C=1C=C2C(=CC=NC2=CC1)N1CCN(CC1)C(=O)N1CCOCC1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | [NH:40]1[CH2:41][CH2:42][O:43][CH2:44][CH2:45]1.c1cn([C:38]([N:37]2[CH2:36][CH2:35][N:34]([c:33]3[cH:32][cH:31][n:30][c:29]4[cH:28][cH:27][c:26](-[c:25]5[c:2]([CH3:1])[n:3][n:4]([C:5]([c:6]6[cH:7][cH:8][cH:9][cH:10][cH:11]6)([c:12]6[cH:13][cH:14][cH:15][cH:16][cH:17]6)[c:18]6[cH:19][cH:20][cH:21][cH:22][cH:23]6)[cH:24]... | C1COCCN1.Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(C(=O)n4ccnc4)CC3)c2c1 | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(C(=O)N4CCOCC4)CC3)c2c1 | null | null | O | Acylation | OtherReaction | f54acadad036c500d6610215cce6f718854c3259cc8fcc05b90bb94bc34f15db | 4adc50dc91067f77b20cc47184a449c49aec5b129f1e8bdc4ffeeb83a1690373 | O=C(N1CCOCC1)N1CCN(c2ccnc3ccc(-c4cnn(C(c5ccccc5)(c5ccccc5)c5ccccc5)c4)cc23)CC1 | [#8:1]1-[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6]-1.[C:7]-[#7:8](-[C;H0;D3;+0:9](=[O;D1;H0:10])-n1:c:c:n:c:1)-[C:11]>>[C:7]-[#7:8](-[C;H0;D3;+0:9](=[O;D1;H0:10])-[N;H0;D3;+0:4]1-[C:3]-[C:2]-[#8:1]-[C:6]-[C:5]-1)-[C:11] | null | [] | 140 | CELSIUS | 8 | HOUR | A mixture of 100 mg 1H-1-imidazolyl{4-[6-(3-methyl-1-trityl-1H-pyrazolyl)-4-quinolyl]piperazin-1-yl}methanone obtained in Example 195 and 1 mL morpholine was stirred overnight at 140° C. Ethyl acetate and water were added to the reaction solution, and the organic layer was separated, washed with brine and dried over an... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Secondary amine | Urea | C1COCCN1.c1c[nH]cn1 | C1COCC[NH]1 | c1c[nH]nc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.C1C[NH]CC[NH]1.C1COCC[NH]1 | Other | O | 140 | 8 | C1COCCN1.Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(C(=O)n4ccnc4)CC3)c2c1>O>Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(C(=O)N4CCOCC4)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b5fe881050714fe1ab8d15203f94e7b7 | CN(C)CCN.Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(C(=O)n4ccnc4)CC3)c2c1>>Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(C(=O)NCCN(C)C)CC3)c2c1 | N1(C=NC=C1)C(=O)N1CCN(CC1)C1=CC=NC2=CC=C(C=C12)C=1C(=NN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C.CN(CCN)C>>CN(CCNC(=O)N1CCN(CC1)C1=CC=NC2=CC=C(C=C12)C=1C(=NN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C)C | [NH2:40][CH2:41][CH2:42][N:43]([CH3:44])[CH3:45].c1cn([C:38]([N:37]2[CH2:36][CH2:35][N:34]([c:33]3[cH:32][cH:31][n:30][c:29]4[cH:28][cH:27][c:26](-[c:25]5[c:2]([CH3:1])[n:3][n:4]([C:5]([c:6]6[cH:7][cH:8][cH:9][cH:10][cH:11]6)([c:12]6[cH:13][cH:14][cH:15][cH:16][cH:17]6)[c:18]6[cH:19][cH:20][cH:21][cH:22][cH:23]6)[cH:24... | CN(C)CCN.Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(C(=O)n4ccnc4)CC3)c2c1 | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(C(=O)NCCN(C)C)CC3)c2c1 | null | null | null | Acylation | OtherReaction | da95d866f0b94870e0cd2d353311103013a93ac1cd41390d4d995e6b8ffafcfd | 60ad1d96378892e2d73f7f438183ffba245ba6472cdcd5667e3ffdb87e1ff406 | c1ccc(C(c2ccccc2)(c2ccccc2)n2cc(-c3ccc4nccc(N5CCNCC5)c4c3)cn2)cc1 | [C:1]-[#7:2](-[C;H0;D3;+0:3](=[O;D1;H0:4])-n1:c:c:n:c:1)-[C:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:1]-[#7:2](-[C;H0;D3;+0:3](=[O;D1;H0:4])-[NH;D2;+0:8]-[C:7]-[C:6])-[C:5] | null | [] | null | null | null | null | 60 mg 1H-1-imidazolyl{4-[6-(3-methyl-1-trityl-1H-pyrazolyl)-4-quinolyl]piperazin-1-yl)methanone obtained in Example 195 and 1 mL N,N-dimethylethylene diamine were reacted in the same manner as in Example 196, to give 29 mg of the title compound as a pale yellow oil.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Primary amine | Urea | c1c[nH]cn1 | null | c1c[nH]nc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.C1C[NH]CC[NH]1 | Other | null | null | null | CN(C)CCN.Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(C(=O)n4ccnc4)CC3)c2c1>>Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(C(=O)NCCN(C)C)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-86b144d1260a4ebc92968a75d0aa8754 | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(C)CC3)c2c1>>Cc1n[nH]cc1-c1ccc2nccc(N3CCN(C)CC3)c2c1.Cl | CN1CCN(CC1)C1=CC=NC2=CC=C(C=C12)C=1C(=NN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C.Cl>>Cl.Cl.CN1CCN(CC1)C1=CC=NC2=CC=C(C=C12)C=1C(=NNC1)C | c1ccc(C(c2ccccc2)(c2ccccc2)[n:4]2[n:3][c:2]([CH3:1])[c:6](-[c:7]3[cH:8][cH:9][c:10]4[n:11][cH:12][cH:13][c:14]([N:15]5[CH2:16][CH2:17][N:18]([CH3:19])[CH2:20][CH2:21]5)[c:22]4[cH:23]3)[cH:5]2)cc1>>[CH3:1][c:2]1[n:3][nH:4][cH:5][c:6]1-[c:7]1[cH:8][cH:9][c:10]2[n:11][cH:12][cH:13][c:14]([N:15]3[CH2:16][CH2:17][N:18]([CH3... | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(C)CC3)c2c1 | Cc1n[nH]cc1-c1ccc2nccc(N3CCN(C)CC3)c2c1.Cl | null | null | null | Functional Group Interconversion | OtherReaction | f8945b6c47d2fe181548474e648e16cfeefa7d5db2d97918e7510aa55a3c60d6 | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | c1cc(N2CCNCC2)c2cc(-c3cn[nH]c3)ccc2n1 | [#7;a:1]1:[c:2]:[c:3]:[c:4]:[n;H0;D3;+0:5]:1-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#7;a:1]1:[c:2]:[c:3]:[c:4]:[nH;D2;+0:5]:1 | null | [] | null | null | null | null | 247 mg 4-(4-methylpiperazin-1-yl)-6-(3-methyl-1-trityl-1H-4-pyrazolyl)quinoline obtained in Example 168 and 3.4 mL of 5 N hydrochloric acid were reacted in the same manner as in Example 163, to give 147 mg of the title compound as yellow crystals.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1cn[nH]c1 | c1cn[nH]c1 | c1cn[nH]c1.c1ccc2ncccc2c1.C1C[NH]CC[NH]1 | Other | null | null | null | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(C)CC3)c2c1>>Cc1n[nH]cc1-c1ccc2nccc(N3CCN(C)CC3)c2c1.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c4378fe124074f00830690e19d019395 | CN1CCN(c2ccnc3ccc(-c4cnn(C(c5ccccc5)(c5ccccc5)c5ccccc5)c4)cc23)CC1>>CN1CCN(c2ccnc3ccc(-c4cn[nH]c4)cc23)CC1.Cl | CN1CCN(CC1)C1=CC=NC2=CC=C(C=C12)C=1C=NN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.Cl>>Cl.Cl.CN1CCN(CC1)C1=CC=NC2=CC=C(C=C12)C=1C=NNC1 | c1ccc(C(c2ccccc2)(c2ccccc2)[n:17]2[n:16][cH:15][c:14](-[c:13]3[cH:12][cH:11][c:10]4[n:9][cH:8][cH:7][c:6]([N:5]5[CH2:4][CH2:3][N:2]([CH3:1])[CH2:22][CH2:21]5)[c:20]4[cH:19]3)[cH:18]2)cc1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][n:9][c:10]3[cH:11][cH:12][c:13](-[c:14]4[cH:15][n:16][nH:17][cH:18]4)[cH:19][c:2... | CN1CCN(c2ccnc3ccc(-c4cnn(C(c5ccccc5)(c5ccccc5)c5ccccc5)c4)cc23)CC1 | CN1CCN(c2ccnc3ccc(-c4cn[nH]c4)cc23)CC1.Cl | null | null | null | Functional Group Interconversion | OtherReaction | f8945b6c47d2fe181548474e648e16cfeefa7d5db2d97918e7510aa55a3c60d6 | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | c1cc(N2CCNCC2)c2cc(-c3cn[nH]c3)ccc2n1 | [#7;a:1]1:[c:2]:[c:3]:[c:4]:[n;H0;D3;+0:5]:1-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#7;a:1]1:[c:2]:[c:3]:[c:4]:[nH;D2;+0:5]:1 | null | [] | null | null | null | null | 186 mg 4-(4-methylpiperazin-1-yl)-6-(1-trityl-1H-4-pyrazolyl)quinoline obtained in Example 169 and 2.6 mL of 5 N hydrochloric acid were reacted in the same manner as in Example 163, to give 127 mg of the title compound as yellow crystals.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1cn[nH]c1 | c1cn[nH]c1 | C1C[NH]CC[NH]1.c1ccc2ncccc2c1.c1cn[nH]c1 | Other | null | null | null | CN1CCN(c2ccnc3ccc(-c4cnn(C(c5ccccc5)(c5ccccc5)c5ccccc5)c4)cc23)CC1>>CN1CCN(c2ccnc3ccc(-c4cn[nH]c4)cc23)CC1.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3c7208a5cea642e29aa21bdb58cb18d5 | CN1CCN(c2ccnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4C(F)(F)F)cc23)CC1>>CN1CCN(c2ccnc3ccc(-c4c[nH]nc4CF)cc23)CC1 | CN1CCN(CC1)C1=CC=NC2=CC=C(C=C12)C=1C(=NN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C(F)(F)F.FC(C(=O)O)(F)F>>CN1CCN(CC1)C1=CC=NC2=CC=C(C=C12)C=1C(=NNC1)CF | F[C:19](F)([c:18]1[c:14](-[c:13]2[cH:12][cH:11][c:10]3[n:9][cH:8][cH:7][c:6]([N:5]4[CH2:4][CH2:3][N:2]([CH3:1])[CH2:24][CH2:23]4)[c:22]3[cH:21]2)[cH:15][n:16](C(c2ccccc2)(c2ccccc2)c2ccccc2)[n:17]1)[F:20]>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][n:9][c:10]3[cH:11][cH:12][c:13](-[c:14]4[cH:15][nH:16][n:17][c:... | CN1CCN(c2ccnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4C(F)(F)F)cc23)CC1 | CN1CCN(c2ccnc3ccc(-c4c[nH]nc4CF)cc23)CC1 | null | null | null | Deprotection | OtherReaction | 3a14dbd48873cb40745eaf7ebb437211fc8a06ac975abe18a781c37f89521ac1 | b7a748fb775d0f63d50dfef2dd4c80133835052887144b61d6cde7223b7c9347 | c1cc(N2CCNCC2)c2cc(-c3cn[nH]c3)ccc2n1 | F-[C;H0;D4;+0:1](-F)(-[F;D1;H0:2])-[c:3]1:[#7;a:4]:[n;H0;D3;+0:5](-C(-c2:c:c:c:c:c:2)(-c2:c:c:c:c:c:2)-c2:c:c:c:c:c:2):[c:6]:[c:7]:1>>[F;D1;H0:2]-[CH2;D2;+0:1]-[c:3]1:[#7;a:4]:[nH;D2;+0:5]:[c:6]:[c:7]:1 | 52.8 | [{"value": 52.8, "product": "CN1CCN(CC1)C1=CC=NC2=CC=C(C=C12)C=1C(=NNC1)CF", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 123 mg 4-(4-methylpiperazin-1-yl)-6-(3-trifluoromethyl-1-trityl-1H-4-pyrazolyl)quinoline obtained in Example 170 and 0.7 mL trifluoroacetic acid were reacted in the same manner as in Example 165, to give 35 mg of the title compound as pale yellow crystals.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group | Primary halide | c1cn[nH]c1.c1ccccc1.c1ccccc1.c1ccccc1 | c1cn[nH]c1 | C1C[NH]CC[NH]1.c1ccc2ncccc2c1.c1cn[nH]c1 | HF | null | null | null | CN1CCN(c2ccnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4C(F)(F)F)cc23)CC1>>CN1CCN(c2ccnc3ccc(-c4c[nH]nc4CF)cc23)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d2be783263524ecc8467214297962b5e | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)c(C)c1-c1ccc2nccc(N3CCN(C)CC3)c2c1>>Cc1n[nH]c(C)c1-c1ccc2nccc(N3CCN(C)CC3)c2c1.Cl | CC1=NN(C(=C1C=1C=C2C(=CC=NC2=CC1)N1CCN(CC1)C)C)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.Cl>>Cl.Cl.CC1=NNC(=C1C=1C=C2C(=CC=NC2=CC1)N1CCN(CC1)C)C | c1ccc(C(c2ccccc2)(c2ccccc2)[n:4]2[n:3][c:2]([CH3:1])[c:7](-[c:8]3[cH:9][cH:10][c:11]4[n:12][cH:13][cH:14][c:15]([N:16]5[CH2:17][CH2:18][N:19]([CH3:20])[CH2:21][CH2:22]5)[c:23]4[cH:24]3)[c:5]2[CH3:6])cc1>>[CH3:1][c:2]1[n:3][nH:4][c:5]([CH3:6])[c:7]1-[c:8]1[cH:9][cH:10][c:11]2[n:12][cH:13][cH:14][c:15]([N:16]3[CH2:17][CH... | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)c(C)c1-c1ccc2nccc(N3CCN(C)CC3)c2c1 | Cc1n[nH]c(C)c1-c1ccc2nccc(N3CCN(C)CC3)c2c1.Cl | null | null | null | Functional Group Interconversion | OtherReaction | f8945b6c47d2fe181548474e648e16cfeefa7d5db2d97918e7510aa55a3c60d6 | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | c1cc(N2CCNCC2)c2cc(-c3cn[nH]c3)ccc2n1 | [C;D1;H3:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[n;H0;D3;+0:6]:1-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C;D1;H3:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[nH;D2;+0:6]:1 | null | [] | null | null | null | null | 75 mg 6-(3,5-dimethyl-1-trityl-1H-pyrazolyl)-4-(4-methylpiperazin-1-yl)quinoline obtained in Example 171 and 1 mL of 5 N hydrochloric acid were reacted in the same manner as in Example 163, to give 147 mg of the title compound as pale yellow crystals.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1cn[nH]c1 | c1cn[nH]c1 | c1cn[nH]c1.c1ccc2ncccc2c1.C1C[NH]CC[NH]1 | Other | null | null | null | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)c(C)c1-c1ccc2nccc(N3CCN(C)CC3)c2c1>>Cc1n[nH]c(C)c1-c1ccc2nccc(N3CCN(C)CC3)c2c1.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-06da356feb9d45e7b65ac008980ac74b | CN1CCN(c2ccnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cc23)CC1>>CN1CCN(c2ccnc3ccc(-c4c[nH]nc4-c4ccc(F)cc4)cc23)CC1.Cl | FC1=CC=C(C=C1)C1=NN(C=C1C=1C=C2C(=CC=NC2=CC1)N1CCN(CC1)C)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.Cl>>Cl.Cl.FC1=CC=C(C=C1)C1=NNC=C1C=1C=C2C(=CC=NC2=CC1)N1CCN(CC1)C | c1ccc(C(c2ccccc2)(c2ccccc2)[n:16]2[cH:15][c:14](-[c:13]3[cH:12][cH:11][c:10]4[n:9][cH:8][cH:7][c:6]([N:5]5[CH2:4][CH2:3][N:2]([CH3:1])[CH2:29][CH2:28]5)[c:27]4[cH:26]3)[c:18](-[c:19]3[cH:20][cH:21][c:22]([F:23])[cH:24][cH:25]3)[n:17]2)cc1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][n:9][c:10]3[cH:11][cH:12][c:... | CN1CCN(c2ccnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cc23)CC1 | CN1CCN(c2ccnc3ccc(-c4c[nH]nc4-c4ccc(F)cc4)cc23)CC1.Cl | null | null | null | Functional Group Interconversion | OtherReaction | f8945b6c47d2fe181548474e648e16cfeefa7d5db2d97918e7510aa55a3c60d6 | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | c1ccc(-c2n[nH]cc2-c2ccc3nccc(N4CCNCC4)c3c2)cc1 | [#7;a:1]1:[c:2]:[c:3]:[c:4]:[n;H0;D3;+0:5]:1-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#7;a:1]1:[c:2]:[c:3]:[c:4]:[nH;D2;+0:5]:1 | null | [] | null | null | null | null | 371 mg 6-[3-(4-fluorophenyl)-1-trityl-1H-pyrazolyl]-4-(4-methylpiperazin-1-yl)quinoline obtained in Example 172 and 4.5 mL of 5 N hydrochloric acid were reacted in the same manner as in Example 163, to give 201 mg of the title compound as pale yellow crystals.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1cn[nH]c1 | c1cn[nH]c1 | C1C[NH]CC[NH]1.c1ccc2ncccc2c1.c1cn[nH]c1.c1ccccc1 | Other | null | null | null | CN1CCN(c2ccnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cc23)CC1>>CN1CCN(c2ccnc3ccc(-c4c[nH]nc4-c4ccc(F)cc4)cc23)CC1.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b5e3293d59c64c3fac06886202154089 | FC(F)(F)c1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCOCC3)c2c1>>FC(F)(F)c1n[nH]cc1-c1ccc2nccc(N3CCOCC3)c2c1 | FC(C1=NN(C=C1C=1C=C2C(=CC=NC2=CC1)N1CCOCC1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)(F)F.FC(C(=O)O)(F)F>>FC(C1=NNC=C1C=1C=C2C(=CC=NC2=CC1)N1CCOCC1)(F)F | c1ccc(C(c2ccccc2)(c2ccccc2)[n:7]2[n:6][c:5]([C:2]([F:1])([F:3])[F:4])[c:9](-[c:10]3[cH:11][cH:12][c:13]4[n:14][cH:15][cH:16][c:17]([N:18]5[CH2:19][CH2:20][O:21][CH2:22][CH2:23]5)[c:24]4[cH:25]3)[cH:8]2)cc1>>[F:1][C:2]([F:3])([F:4])[c:5]1[n:6][nH:7][cH:8][c:9]1-[c:10]1[cH:11][cH:12][c:13]2[n:14][cH:15][cH:16][c:17]([N:1... | FC(F)(F)c1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCOCC3)c2c1 | FC(F)(F)c1n[nH]cc1-c1ccc2nccc(N3CCOCC3)c2c1 | null | null | null | Deprotection | OtherReaction | 92b7543875cfe438a4c5cf3faf8e6c828b5eea356096f8ebdcd8d3241dc18933 | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | c1cc(N2CCOCC2)c2cc(-c3cn[nH]c3)ccc2n1 | [#7;a:1]1:[c:2]:[c:3]:[c:4]:[n;H0;D3;+0:5]:1-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#7;a:1]1:[c:2]:[c:3]:[c:4]:[nH;D2;+0:5]:1 | 79.2 | [{"value": 79.2, "product": "FC(C1=NNC=C1C=1C=C2C(=CC=NC2=CC1)N1CCOCC1)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 122 mg 4-[6-(3-trifluoromethyl-1-trityl-1H-4-pyrazolyl)-4-quinolyl]morpholine obtained in Example 174 and 1.5 mL trifluoroacetic acid were reacted in the same manner as in Example 165, to give 57 mg of the title compound as pale yellow crystals.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1cn[nH]c1 | c1cn[nH]c1 | c1cn[nH]c1.c1ccc2ncccc2c1.C1COCC[NH]1 | Other | null | null | null | FC(F)(F)c1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCOCC3)c2c1>>FC(F)(F)c1n[nH]cc1-c1ccc2nccc(N3CCOCC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-69fe0d25ba7b4eaf8d68e3a44e389760 | FC(F)(F)c1cccc(N2CCN(c3ccnc4ccc(-c5cnn(C(c6ccccc6)(c6ccccc6)c6ccccc6)c5)cc34)CC2)c1>>Cl.FC(F)(F)c1cccc(N2CCN(c3ccnc4ccc(-c5cn[nH]c5)cc34)CC2)c1 | FC(C=1C=C(C=CC1)N1CCN(CC1)C1=CC=NC2=CC=C(C=C12)C=1C=NN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)(F)F.Cl>>Cl.Cl.N1N=CC(=C1)C=1C=C2C(=CC=NC2=CC1)N1CCN(CC1)C1=CC(=CC=C1)C(F)(F)F | c1ccc(C(c2ccccc2)(c2ccccc2)[n:27]2[n:26][cH:25][c:24](-[c:23]3[cH:22][cH:21][c:20]4[n:19][cH:18][cH:17][c:16]([N:15]5[CH2:14][CH2:13][N:12]([c:11]6[cH:10][cH:9][cH:8][c:7]([C:4]([F:3])([F:5])[F:6])[cH:33]6)[CH2:32][CH2:31]5)[c:30]4[cH:29]3)[cH:28]2)cc1>>[ClH:2].[F:3][C:4]([F:5])([F:6])[c:7]1[cH:8][cH:9][cH:10][c:11]([N... | FC(F)(F)c1cccc(N2CCN(c3ccnc4ccc(-c5cnn(C(c6ccccc6)(c6ccccc6)c6ccccc6)c5)cc34)CC2)c1 | Cl.FC(F)(F)c1cccc(N2CCN(c3ccnc4ccc(-c5cn[nH]c5)cc34)CC2)c1 | null | null | null | Functional Group Interconversion | OtherReaction | f8945b6c47d2fe181548474e648e16cfeefa7d5db2d97918e7510aa55a3c60d6 | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | c1ccc(N2CCN(c3ccnc4ccc(-c5cn[nH]c5)cc34)CC2)cc1 | [#7;a:1]1:[c:2]:[c:3]:[c:4]:[n;H0;D3;+0:5]:1-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#7;a:1]1:[c:2]:[c:3]:[c:4]:[nH;D2;+0:5]:1 | null | [] | null | null | null | null | 104 mg 4-[4-(3-trifluoromethylphenyl)piperazin-1-yl]-6-(1-trityl-1H-4-pyrazolyl) quinoline obtained in Example 175 and 1.2 mL of 5 N hydrochloric acid were reacted in the same manner as in Example 163, to give 74 mg of the title compound as yellowish orange crystals.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1cn[nH]c1 | c1cn[nH]c1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccc2ncccc2c1.c1cn[nH]c1 | Other | null | null | null | FC(F)(F)c1cccc(N2CCN(c3ccnc4ccc(-c5cnn(C(c6ccccc6)(c6ccccc6)c6ccccc6)c5)cc34)CC2)c1>>Cl.FC(F)(F)c1cccc(N2CCN(c3ccnc4ccc(-c5cn[nH]c5)cc34)CC2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a77d00bc0b204e07806b806be3665099 | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(c4cccc(C(F)(F)F)c4)CC3)c2c1>>Cc1n[nH]cc1-c1ccc2nccc(N3CCN(c4cccc(C(F)(F)F)c4)CC3)c2c1.Cl | CC1=NN(C=C1C=1C=C2C(=CC=NC2=CC1)N1CCN(CC1)C1=CC(=CC=C1)C(F)(F)F)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.Cl>>Cl.Cl.CC1=NNC=C1C=1C=C2C(=CC=NC2=CC1)N1CCN(CC1)C1=CC(=CC=C1)C(F)(F)F | c1ccc(C(c2ccccc2)(c2ccccc2)[n:4]2[n:3][c:2]([CH3:1])[c:6](-[c:7]3[cH:8][cH:9][c:10]4[n:11][cH:12][cH:13][c:14]([N:15]5[CH2:16][CH2:17][N:18]([c:19]6[cH:20][cH:21][cH:22][c:23]([C:24]([F:25])([F:26])[F:27])[cH:28]6)[CH2:29][CH2:30]5)[c:31]4[cH:32]3)[cH:5]2)cc1>>[CH3:1][c:2]1[n:3][nH:4][cH:5][c:6]1-[c:7]1[cH:8][cH:9][c:1... | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(c4cccc(C(F)(F)F)c4)CC3)c2c1 | Cc1n[nH]cc1-c1ccc2nccc(N3CCN(c4cccc(C(F)(F)F)c4)CC3)c2c1.Cl | null | null | null | Functional Group Interconversion | OtherReaction | f8945b6c47d2fe181548474e648e16cfeefa7d5db2d97918e7510aa55a3c60d6 | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | c1ccc(N2CCN(c3ccnc4ccc(-c5cn[nH]c5)cc34)CC2)cc1 | [#7;a:1]1:[c:2]:[c:3]:[c:4]:[n;H0;D3;+0:5]:1-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#7;a:1]1:[c:2]:[c:3]:[c:4]:[nH;D2;+0:5]:1 | null | [] | null | null | null | null | 115 mg 6-(3-methyl-1-trityl-1H-4-pyrazolyl)-4-[4-(3-trifluoromethylphenyl)piperazin-1-yl]quinoline obtained in Example 176 and 1.3 mL of 5 N hydrochloric acid were reacted in the same manner as in Example 163, to give 68 mg of the title compound as yellowish orange crystals.
Conditions: See reaction.notes.procedure_det... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1cn[nH]c1 | c1cn[nH]c1 | c1cn[nH]c1.c1ccc2ncccc2c1.C1C[NH]CC[NH]1.c1ccccc1 | Other | null | null | null | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(c4cccc(C(F)(F)F)c4)CC3)c2c1>>Cc1n[nH]cc1-c1ccc2nccc(N3CCN(c4cccc(C(F)(F)F)c4)CC3)c2c1.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0c3b30bb85944f5b82385e78c33a431a | COc1cccc(N2CCN(c3ccnc4ccc(-c5cn(C(c6ccccc6)(c6ccccc6)c6ccccc6)nc5C)cc34)CC2)n1>>COc1cccc(N2CCN(c3ccnc4ccc(-c5c[nH]nc5C)cc34)CC2)n1.Cl.Cl | COC1=CC=CC(=N1)N1CCN(CC1)C1=CC=NC2=CC=C(C=C12)C=1C(=NN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C.Cl>>Cl.Cl.Cl.COC1=CC=CC(=N1)N1CCN(CC1)C1=CC=NC2=CC=C(C=C12)C=1C(=NNC1)C | c1ccc(C(c2ccccc2)(c2ccccc2)[n:22]2[cH:21][c:20](-[c:19]3[cH:18][cH:17][c:16]4[n:15][cH:14][cH:13][c:12]([N:11]5[CH2:10][CH2:9][N:8]([c:7]6[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[n:30]6)[CH2:29][CH2:28]5)[c:27]4[cH:26]3)[c:24]([CH3:25])[n:23]2)cc1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([N:8]2[CH2:9][CH2:10][N:11]([c:1... | COc1cccc(N2CCN(c3ccnc4ccc(-c5cn(C(c6ccccc6)(c6ccccc6)c6ccccc6)nc5C)cc34)CC2)n1 | COc1cccc(N2CCN(c3ccnc4ccc(-c5c[nH]nc5C)cc34)CC2)n1.Cl.Cl | null | null | null | Functional Group Interconversion | OtherReaction | f8945b6c47d2fe181548474e648e16cfeefa7d5db2d97918e7510aa55a3c60d6 | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | c1ccc(N2CCN(c3ccnc4ccc(-c5cn[nH]c5)cc34)CC2)nc1 | [#7;a:1]1:[c:2]:[c:3]:[c:4]:[n;H0;D3;+0:5]:1-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#7;a:1]1:[c:2]:[c:3]:[c:4]:[nH;D2;+0:5]:1 | null | [] | null | null | null | null | 120 mg 4-[4-(6-methoxy-2-pyridyl)piperazin-1-yl]-6-(3-methyl-1-trityl-1H-4-pyrazolyl)quinoline obtained in Example 178 and 1.4 mL of 5 N— hydrochloric acid were reacted in the same manner as in Example 163, to give 87 mg of the title compound as pale yellow crystals.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1cn[nH]c1 | c1cn[nH]c1 | c1ccncc1.C1C[NH]CC[NH]1.c1ccc2ncccc2c1.c1cn[nH]c1 | Other | null | null | null | COc1cccc(N2CCN(c3ccnc4ccc(-c5cn(C(c6ccccc6)(c6ccccc6)c6ccccc6)nc5C)cc34)CC2)n1>>COc1cccc(N2CCN(c3ccnc4ccc(-c5c[nH]nc5C)cc34)CC2)n1.Cl.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e54decf0ba884e2fac60d8d3fd7aa45c | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(C(N)=O)CC3)c2c1>>Cc1n[nH]cc1-c1ccc2nccc(N3CCN(C(N)=O)CC3)c2c1 | CC1=NN(C=C1C=1C=C2C(=CC=NC2=CC1)N1CCN(CC1)C(=O)N)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.Cl>>CC1=NNC=C1C=1C=C2C(=CC=NC2=CC1)N1CCN(CC1)C(=O)N | c1ccc(C(c2ccccc2)(c2ccccc2)[n:4]2[n:3][c:2]([CH3:1])[c:6](-[c:7]3[cH:8][cH:9][c:10]4[n:11][cH:12][cH:13][c:14]([N:15]5[CH2:16][CH2:17][N:18]([C:19]([NH2:20])=[O:21])[CH2:22][CH2:23]5)[c:24]4[cH:25]3)[cH:5]2)cc1>>[CH3:1][c:2]1[n:3][nH:4][cH:5][c:6]1-[c:7]1[cH:8][cH:9][c:10]2[n:11][cH:12][cH:13][c:14]([N:15]3[CH2:16][CH2... | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(C(N)=O)CC3)c2c1 | Cc1n[nH]cc1-c1ccc2nccc(N3CCN(C(N)=O)CC3)c2c1 | null | null | null | Deprotection | OtherReaction | 92b7543875cfe438a4c5cf3faf8e6c828b5eea356096f8ebdcd8d3241dc18933 | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | c1cc(N2CCNCC2)c2cc(-c3cn[nH]c3)ccc2n1 | [#7;a:1]1:[c:2]:[c:3]:[c:4]:[n;H0;D3;+0:5]:1-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#7;a:1]1:[c:2]:[c:3]:[c:4]:[nH;D2;+0:5]:1 | 42.1 | [{"value": 42.1, "product": "CC1=NNC=C1C=1C=C2C(=CC=NC2=CC1)N1CCN(CC1)C(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 94 mg 4-[6-(3-methyl-1-trityl-1H-4-pyrazolyl)-4-quinolyl]-1-piperazine carboxamide obtained in Example 179 and 1.3 mL of 5 N hydrochloric acid were reacted in the same manner as in Example 162, to give 23 mg of the title compound as a pale yellow solid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1cn[nH]c1 | c1cn[nH]c1 | c1cn[nH]c1.c1ccc2ncccc2c1.C1C[NH]CC[NH]1 | Other | null | null | null | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(C(N)=O)CC3)c2c1>>Cc1n[nH]cc1-c1ccc2nccc(N3CCN(C(N)=O)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-db04afed677749f3810ef391a58a6385 | CCNC(=O)N1CCN(c2ccnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4C)cc23)CC1>>CCNC(=O)N1CCN(c2ccnc3ccc(-c4c[nH]nc4C)cc23)CC1.Cl | C(C)NC(=O)N1CCN(CC1)C1=CC=NC2=CC=C(C=C12)C=1C(=NN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C.Cl>>Cl.Cl.C(C)NC(=O)N1CCN(CC1)C1=CC=NC2=CC=C(C=C12)C=1C(=NNC1)C | c1ccc(C(c2ccccc2)(c2ccccc2)[n:20]2[cH:19][c:18](-[c:17]3[cH:16][cH:15][c:14]4[n:13][cH:12][cH:11][c:10]([N:9]5[CH2:8][CH2:7][N:6]([C:4]([NH:3][CH2:2][CH3:1])=[O:5])[CH2:27][CH2:26]5)[c:25]4[cH:24]3)[c:22]([CH3:23])[n:21]2)cc1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][N:9]([c:10]2[cH:11][cH:12][n:13][c:14]3... | CCNC(=O)N1CCN(c2ccnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4C)cc23)CC1 | CCNC(=O)N1CCN(c2ccnc3ccc(-c4c[nH]nc4C)cc23)CC1.Cl | null | null | null | Functional Group Interconversion | OtherReaction | f8945b6c47d2fe181548474e648e16cfeefa7d5db2d97918e7510aa55a3c60d6 | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | c1cc(N2CCNCC2)c2cc(-c3cn[nH]c3)ccc2n1 | [#7;a:1]1:[c:2]:[c:3]:[c:4]:[n;H0;D3;+0:5]:1-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#7;a:1]1:[c:2]:[c:3]:[c:4]:[nH;D2;+0:5]:1 | null | [] | null | null | null | null | 118 mg N-ethyl-4-[6-(3-methyl-1-trityl-1H-pyrazolyl)-4-quinolyl]-1-piperazine carboxamide obtained in Example 180 and 1.5 mL of 5 N hydrochloric acid were reacted in the same manner as in Example 163, to give 72 mg of the title compound as a pale yellow solid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1cn[nH]c1 | c1cn[nH]c1 | C1C[NH]CC[NH]1.c1ccc2ncccc2c1.c1cn[nH]c1 | Other | null | null | null | CCNC(=O)N1CCN(c2ccnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4C)cc23)CC1>>CCNC(=O)N1CCN(c2ccnc3ccc(-c4c[nH]nc4C)cc23)CC1.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e8583160cece4bc5b5113fa62fcc4dba | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(C(=O)Nc4ccccc4)CC3)c2c1>>Cc1n[nH]cc1-c1ccc2nccc(N3CCN(C(=O)Nc4ccccc4)CC3)c2c1.Cl | C1(=CC=CC=C1)NC(=O)N1CCN(CC1)C1=CC=NC2=CC=C(C=C12)C=1C(=NN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C.Cl>>Cl.Cl.C1(=CC=CC=C1)NC(=O)N1CCN(CC1)C1=CC=NC2=CC=C(C=C12)C=1C(=NNC1)C | c1ccc(C(c2ccccc2)(c2ccccc2)[n:4]2[n:3][c:2]([CH3:1])[c:6](-[c:7]3[cH:8][cH:9][c:10]4[n:11][cH:12][cH:13][c:14]([N:15]5[CH2:16][CH2:17][N:18]([C:19](=[O:20])[NH:21][c:22]6[cH:23][cH:24][cH:25][cH:26][cH:27]6)[CH2:28][CH2:29]5)[c:30]4[cH:31]3)[cH:5]2)cc1>>[CH3:1][c:2]1[n:3][nH:4][cH:5][c:6]1-[c:7]1[cH:8][cH:9][c:10]2[n:1... | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(C(=O)Nc4ccccc4)CC3)c2c1 | Cc1n[nH]cc1-c1ccc2nccc(N3CCN(C(=O)Nc4ccccc4)CC3)c2c1.Cl | null | null | null | Functional Group Interconversion | OtherReaction | f8945b6c47d2fe181548474e648e16cfeefa7d5db2d97918e7510aa55a3c60d6 | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | O=C(Nc1ccccc1)N1CCN(c2ccnc3ccc(-c4cn[nH]c4)cc23)CC1 | [#7;a:1]1:[c:2]:[c:3]:[c:4]:[n;H0;D3;+0:5]:1-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#7;a:1]1:[c:2]:[c:3]:[c:4]:[nH;D2;+0:5]:1 | null | [] | null | null | null | null | 63 mg N1-phenyl-4-[6-(3-methyl-1-trityl-1H-pyrazolyl)-4-quinolyl]-1-piperazine carboxamide obtained in Example 181 and 0.7 mL of 5 N hydrochloric acid were reacted in the same manner as in Example 163, to give 30 mg of the title compound as pale yellow crystals.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1cn[nH]c1 | c1cn[nH]c1 | c1cn[nH]c1.c1ccc2ncccc2c1.C1C[NH]CC[NH]1.c1ccccc1 | Other | null | null | null | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(C(=O)Nc4ccccc4)CC3)c2c1>>Cc1n[nH]cc1-c1ccc2nccc(N3CCN(C(=O)Nc4ccccc4)CC3)c2c1.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5f2bbce63b7b434e86998dcb5ac0ff9f | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(C(=O)N(C)C)CC3)c2c1>>Cc1n[nH]cc1-c1ccc2nccc(N3CCN(C(=O)N(C)C)CC3)c2c1 | CN(C(=O)N1CCN(CC1)C1=CC=NC2=CC=C(C=C12)C=1C(=NN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C)C.FC(C(=O)O)(F)F>>CN(C(=O)N1CCN(CC1)C1=CC=NC2=CC=C(C=C12)C=1C(=NNC1)C)C | c1ccc(C(c2ccccc2)(c2ccccc2)[n:4]2[n:3][c:2]([CH3:1])[c:6](-[c:7]3[cH:8][cH:9][c:10]4[n:11][cH:12][cH:13][c:14]([N:15]5[CH2:16][CH2:17][N:18]([C:19](=[O:20])[N:21]([CH3:22])[CH3:23])[CH2:24][CH2:25]5)[c:26]4[cH:27]3)[cH:5]2)cc1>>[CH3:1][c:2]1[n:3][nH:4][cH:5][c:6]1-[c:7]1[cH:8][cH:9][c:10]2[n:11][cH:12][cH:13][c:14]([N:... | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(C(=O)N(C)C)CC3)c2c1 | Cc1n[nH]cc1-c1ccc2nccc(N3CCN(C(=O)N(C)C)CC3)c2c1 | null | null | null | Deprotection | OtherReaction | 92b7543875cfe438a4c5cf3faf8e6c828b5eea356096f8ebdcd8d3241dc18933 | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | c1cc(N2CCNCC2)c2cc(-c3cn[nH]c3)ccc2n1 | [#7;a:1]1:[c:2]:[c:3]:[c:4]:[n;H0;D3;+0:5]:1-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#7;a:1]1:[c:2]:[c:3]:[c:4]:[nH;D2;+0:5]:1 | 70.1 | [{"value": 70.1, "product": "CN(C(=O)N1CCN(CC1)C1=CC=NC2=CC=C(C=C12)C=1C(=NNC1)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 38 mg N,N-dimethyl 4-[6-(3-methyl-1-trityl-1H-pyrazolyl)-4-quinolyl]-1-piperazine carboxamide obtained in Example 182 and 0.2 mL trifluoroacetic acid were reacted in the same manner as in Example 165, to give 16 mg of the title compound as pale yellow crystals.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1cn[nH]c1 | c1cn[nH]c1 | c1cn[nH]c1.c1ccc2ncccc2c1.C1C[NH]CC[NH]1 | Other | null | null | null | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(C(=O)N(C)C)CC3)c2c1>>Cc1n[nH]cc1-c1ccc2nccc(N3CCN(C(=O)N(C)C)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-10d1169e32a1472798369eb75577d4b3 | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(S(=O)(=O)N(C)C)CC3)c2c1>>Cc1n[nH]cc1-c1ccc2nccc(N3CCN(S(=O)(=O)N(C)C)CC3)c2c1 | CN(S(=O)(=O)N1CCN(CC1)C1=CC=NC2=CC=C(C=C12)C=1C(=NN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C)C.FC(C(=O)O)(F)F>>CN(S(=O)(=O)N1CCN(CC1)C1=CC=NC2=CC=C(C=C12)C=1C(=NNC1)C)C | c1ccc(C(c2ccccc2)(c2ccccc2)[n:4]2[n:3][c:2]([CH3:1])[c:6](-[c:7]3[cH:8][cH:9][c:10]4[n:11][cH:12][cH:13][c:14]([N:15]5[CH2:16][CH2:17][N:18]([S:19](=[O:20])(=[O:21])[N:22]([CH3:23])[CH3:24])[CH2:25][CH2:26]5)[c:27]4[cH:28]3)[cH:5]2)cc1>>[CH3:1][c:2]1[n:3][nH:4][cH:5][c:6]1-[c:7]1[cH:8][cH:9][c:10]2[n:11][cH:12][cH:13][... | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(S(=O)(=O)N(C)C)CC3)c2c1 | Cc1n[nH]cc1-c1ccc2nccc(N3CCN(S(=O)(=O)N(C)C)CC3)c2c1 | null | null | null | Deprotection | OtherReaction | 92b7543875cfe438a4c5cf3faf8e6c828b5eea356096f8ebdcd8d3241dc18933 | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | c1cc(N2CCNCC2)c2cc(-c3cn[nH]c3)ccc2n1 | [#7;a:1]1:[c:2]:[c:3]:[c:4]:[n;H0;D3;+0:5]:1-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#7;a:1]1:[c:2]:[c:3]:[c:4]:[nH;D2;+0:5]:1 | 69.4 | [{"value": 69.4, "product": "CN(S(=O)(=O)N1CCN(CC1)C1=CC=NC2=CC=C(C=C12)C=1C(=NNC1)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 37 mg N,N-dimethyl-4-[6-(3-methyl-1-trityl-1H-pyrazolyl)-4-quinolyl]-1-piperazine sulfonamide obtained in Example 183 and 0.2 mL trifluoroacetic acid were reacted in the same manner as in Example 165, to give 16 mg of the title compound as pale yellow crystals.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1cn[nH]c1 | c1cn[nH]c1 | c1cn[nH]c1.c1ccc2ncccc2c1.C1C[NH]CC[NH]1 | Other | null | null | null | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(S(=O)(=O)N(C)C)CC3)c2c1>>Cc1n[nH]cc1-c1ccc2nccc(N3CCN(S(=O)(=O)N(C)C)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1d559674856444ba825aab478da27af6 | CN(C)S(=O)(=O)N1CCN(c2ccnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4C(F)(F)F)cc23)CC1>>CN(C)S(=O)(=O)N1CCN(c2ccnc3ccc(-c4c[nH]nc4C(F)(F)F)cc23)CC1 | CN(S(=O)(=O)N1CCN(CC1)C1=CC=NC2=CC=C(C=C12)C=1C(=NN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C(F)(F)F)C.FC(C(=O)O)(F)F>>CN(S(=O)(=O)N1CCN(CC1)C1=CC=NC2=CC=C(C=C12)C=1C(=NNC1)C(F)(F)F)C | c1ccc(C(c2ccccc2)(c2ccccc2)[n:21]2[cH:20][c:19](-[c:18]3[cH:17][cH:16][c:15]4[n:14][cH:13][cH:12][c:11]([N:10]5[CH2:9][CH2:8][N:7]([S:4]([N:2]([CH3:1])[CH3:3])(=[O:5])=[O:6])[CH2:31][CH2:30]5)[c:29]4[cH:28]3)[c:23]([C:24]([F:25])([F:26])[F:27])[n:22]2)cc1>>[CH3:1][N:2]([CH3:3])[S:4](=[O:5])(=[O:6])[N:7]1[CH2:8][CH2:9][... | CN(C)S(=O)(=O)N1CCN(c2ccnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4C(F)(F)F)cc23)CC1 | CN(C)S(=O)(=O)N1CCN(c2ccnc3ccc(-c4c[nH]nc4C(F)(F)F)cc23)CC1 | null | null | null | Deprotection | OtherReaction | 92b7543875cfe438a4c5cf3faf8e6c828b5eea356096f8ebdcd8d3241dc18933 | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | c1cc(N2CCNCC2)c2cc(-c3cn[nH]c3)ccc2n1 | [#7;a:1]1:[c:2]:[c:3]:[c:4]:[n;H0;D3;+0:5]:1-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#7;a:1]1:[c:2]:[c:3]:[c:4]:[nH;D2;+0:5]:1 | 65.9 | [{"value": 65.9, "product": "CN(S(=O)(=O)N1CCN(CC1)C1=CC=NC2=CC=C(C=C12)C=1C(=NNC1)C(F)(F)F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 107 mg N1,N1-dimethyl-4-[6-(3-trifluoromethyl-1-trityl-1H-4-pyrazolyl)-4-quinolyl]-1-piperazine sulfonamide obtained in Example 186 and 1 mL trifluoroacetic acid were reacted in the same manner as in Example 165, to give 46 mg of the title compound as pale yellow crystals.
Conditions: See reaction.notes.procedure_detai... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1cn[nH]c1 | c1cn[nH]c1 | C1C[NH]CC[NH]1.c1ccc2ncccc2c1.c1cn[nH]c1 | Other | null | null | null | CN(C)S(=O)(=O)N1CCN(c2ccnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4C(F)(F)F)cc23)CC1>>CN(C)S(=O)(=O)N1CCN(c2ccnc3ccc(-c4c[nH]nc4C(F)(F)F)cc23)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fb29228e8a37487cad26081daebb10c4 | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3C=CN(S(N)(=O)=O)C=C3)c2c1>>Cc1n[nH]cc1-c1ccc2nccc(N3C=CN(S(N)(=O)=O)C=C3)c2c1 | CC1=NN(C=C1C=1C=C2C(=CC=NC2=CC1)N1C=CN(C=C1)S(=O)(=O)N)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.Cl>>CC1=NNC=C1C=1C=C2C(=CC=NC2=CC1)N1C=CN(C=C1)S(=O)(=O)N | c1ccc(C(c2ccccc2)(c2ccccc2)[n:4]2[n:3][c:2]([CH3:1])[c:6](-[c:7]3[cH:8][cH:9][c:10]4[n:11][cH:12][cH:13][c:14]([N:15]5[CH:16]=[CH:17][N:18]([S:19]([NH2:20])(=[O:21])=[O:22])[CH:23]=[CH:24]5)[c:25]4[cH:26]3)[cH:5]2)cc1>>[CH3:1][c:2]1[n:3][nH:4][cH:5][c:6]1-[c:7]1[cH:8][cH:9][c:10]2[n:11][cH:12][cH:13][c:14]([N:15]3[CH:1... | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3C=CN(S(N)(=O)=O)C=C3)c2c1 | Cc1n[nH]cc1-c1ccc2nccc(N3C=CN(S(N)(=O)=O)C=C3)c2c1 | null | null | null | Deprotection | OtherReaction | 92b7543875cfe438a4c5cf3faf8e6c828b5eea356096f8ebdcd8d3241dc18933 | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | C1=CN(c2ccnc3ccc(-c4cn[nH]c4)cc23)C=CN1 | [#7;a:1]1:[c:2]:[c:3]:[c:4]:[n;H0;D3;+0:5]:1-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#7;a:1]1:[c:2]:[c:3]:[c:4]:[nH;D2;+0:5]:1 | 58 | [{"value": 58.0, "product": "CC1=NNC=C1C=1C=C2C(=CC=NC2=CC1)N1C=CN(C=C1)S(=O)(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 40 mg 4-[6-(3-methyl-1-trityl-1H-4-pyrazolyl)-4-quinolyl]-1-pyrazine sulfonamide obtained in Example 189 and 0.5 mL of 5 N hydrochloric acid were reacted in the same manner as in Example 162, to give 14 mg of the title compound as white crystals.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1cn[nH]c1 | c1cn[nH]c1 | c1cn[nH]c1.c1ccc2ncccc2c1.C1=C[NH]C=C[NH]1 | Other | null | null | null | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3C=CN(S(N)(=O)=O)C=C3)c2c1>>Cc1n[nH]cc1-c1ccc2nccc(N3C=CN(S(N)(=O)=O)C=C3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-eb96437062ab4d75bb126321ca9d71d6 | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(CC(N)=O)CC3)c2c1>>Cc1n[nH]cc1-c1ccc2nccc(N3CCN(CC(N)=O)CC3)c2c1 | CC1=NN(C=C1C=1C=C2C(=CC=NC2=CC1)N1CCN(CC1)CC(=O)N)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.FC(C(=O)O)(F)F>>CC1=NNC=C1C=1C=C2C(=CC=NC2=CC1)N1CCN(CC1)CC(=O)N | c1ccc(C(c2ccccc2)(c2ccccc2)[n:4]2[n:3][c:2]([CH3:1])[c:6](-[c:7]3[cH:8][cH:9][c:10]4[n:11][cH:12][cH:13][c:14]([N:15]5[CH2:16][CH2:17][N:18]([CH2:19][C:20]([NH2:21])=[O:22])[CH2:23][CH2:24]5)[c:25]4[cH:26]3)[cH:5]2)cc1>>[CH3:1][c:2]1[n:3][nH:4][cH:5][c:6]1-[c:7]1[cH:8][cH:9][c:10]2[n:11][cH:12][cH:13][c:14]([N:15]3[CH2... | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(CC(N)=O)CC3)c2c1 | Cc1n[nH]cc1-c1ccc2nccc(N3CCN(CC(N)=O)CC3)c2c1 | null | null | null | Deprotection | OtherReaction | 92b7543875cfe438a4c5cf3faf8e6c828b5eea356096f8ebdcd8d3241dc18933 | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | c1cc(N2CCNCC2)c2cc(-c3cn[nH]c3)ccc2n1 | [#7;a:1]1:[c:2]:[c:3]:[c:4]:[n;H0;D3;+0:5]:1-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#7;a:1]1:[c:2]:[c:3]:[c:4]:[nH;D2;+0:5]:1 | 34.7 | [{"value": 34.7, "product": "CC1=NNC=C1C=1C=C2C(=CC=NC2=CC1)N1CCN(CC1)CC(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 39 mg 2-{4-[6-(3-methyl-1-trityl-1H-4-pyrazolyl)-4-quinolyl]piperazin-1-yl}acetamide obtained in Example 190 and 1 mL trifluoroacetic acid were reacted in the same manner as in Example 165, to give 8 mg of the title compound as a pale yellow solid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1cn[nH]c1 | c1cn[nH]c1 | c1cn[nH]c1.c1ccc2ncccc2c1.C1C[NH]CC[NH]1 | Other | null | null | null | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(CC(N)=O)CC3)c2c1>>Cc1n[nH]cc1-c1ccc2nccc(N3CCN(CC(N)=O)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a10340c9c9cf4b83b77c8347d8763718 | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(CC(=O)N(C)C)CC3)c2c1>>Cc1n[nH]cc1-c1ccc2nccc(N3CCN(CC(=O)N(C)C)CC3)c2c1 | CN(C(CN1CCN(CC1)C1=CC=NC2=CC=C(C=C12)C=1C(=NN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C)=O)C.FC(C(=O)O)(F)F>>CN(C(CN1CCN(CC1)C1=CC=NC2=CC=C(C=C12)C=1C(=NNC1)C)=O)C | c1ccc(C(c2ccccc2)(c2ccccc2)[n:4]2[n:3][c:2]([CH3:1])[c:6](-[c:7]3[cH:8][cH:9][c:10]4[n:11][cH:12][cH:13][c:14]([N:15]5[CH2:16][CH2:17][N:18]([CH2:19][C:20](=[O:21])[N:22]([CH3:23])[CH3:24])[CH2:25][CH2:26]5)[c:27]4[cH:28]3)[cH:5]2)cc1>>[CH3:1][c:2]1[n:3][nH:4][cH:5][c:6]1-[c:7]1[cH:8][cH:9][c:10]2[n:11][cH:12][cH:13][c... | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(CC(=O)N(C)C)CC3)c2c1 | Cc1n[nH]cc1-c1ccc2nccc(N3CCN(CC(=O)N(C)C)CC3)c2c1 | null | null | null | Deprotection | OtherReaction | 92b7543875cfe438a4c5cf3faf8e6c828b5eea356096f8ebdcd8d3241dc18933 | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | c1cc(N2CCNCC2)c2cc(-c3cn[nH]c3)ccc2n1 | [#7;a:1]1:[c:2]:[c:3]:[c:4]:[n;H0;D3;+0:5]:1-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#7;a:1]1:[c:2]:[c:3]:[c:4]:[nH;D2;+0:5]:1 | 16 | [{"value": 16.0, "product": "CN(C(CN1CCN(CC1)C1=CC=NC2=CC=C(C=C12)C=1C(=NNC1)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 82 mg N,N-dimethyl-2-{4-[6-(3-methyl-1-trityl-1H-4-pyrazolyl)-4-quinolyl]piperazin-1-yl}acetamide obtained in Example 191 and 1 mL trifluoroacetic acid were reacted in the same manner as in Example 165, to give 8 mg of the title compound as pale yellow crystals.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1cn[nH]c1 | c1cn[nH]c1 | c1cn[nH]c1.c1ccc2ncccc2c1.C1C[NH]CC[NH]1 | Other | null | null | null | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(CC(=O)N(C)C)CC3)c2c1>>Cc1n[nH]cc1-c1ccc2nccc(N3CCN(CC(=O)N(C)C)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3fe30596bbcc4fbfb0b9dde94216350a | O=C(N1CCOCC1)N1CCN(c2ccnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4C(F)(F)F)cc23)CC1>>O=C(N1CCOCC1)N1CCN(c2ccnc3ccc(-c4c[nH]nc4C(F)(F)F)cc23)CC1 | O1CCN(CC1)C(=O)N1CCN(CC1)C1=CC=NC2=CC=C(C=C12)C=1C(=NN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C(F)(F)F.FC(C(=O)O)(F)F>>O1CCN(CC1)C(=O)N1CCN(CC1)C1=CC=NC2=CC=C(C=C12)C=1C(=NNC1)C(F)(F)F | c1ccc(C(c2ccccc2)(c2ccccc2)[n:23]2[cH:22][c:21](-[c:20]3[cH:19][cH:18][c:17]4[n:16][cH:15][cH:14][c:13]([N:12]5[CH2:11][CH2:10][N:9]([C:2](=[O:1])[N:3]6[CH2:4][CH2:5][O:6][CH2:7][CH2:8]6)[CH2:33][CH2:32]5)[c:31]4[cH:30]3)[c:25]([C:26]([F:27])([F:28])[F:29])[n:24]2)cc1>>[O:1]=[C:2]([N:3]1[CH2:4][CH2:5][O:6][CH2:7][CH2:8... | O=C(N1CCOCC1)N1CCN(c2ccnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4C(F)(F)F)cc23)CC1 | O=C(N1CCOCC1)N1CCN(c2ccnc3ccc(-c4c[nH]nc4C(F)(F)F)cc23)CC1 | null | null | null | Deprotection | OtherReaction | 92b7543875cfe438a4c5cf3faf8e6c828b5eea356096f8ebdcd8d3241dc18933 | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | O=C(N1CCOCC1)N1CCN(c2ccnc3ccc(-c4cn[nH]c4)cc23)CC1 | [#7;a:1]1:[c:2]:[c:3]:[c:4]:[n;H0;D3;+0:5]:1-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#7;a:1]1:[c:2]:[c:3]:[c:4]:[nH;D2;+0:5]:1 | 81.9 | [{"value": 81.9, "product": "O1CCN(CC1)C(=O)N1CCN(CC1)C1=CC=NC2=CC=C(C=C12)C=1C(=NNC1)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 123 mg morpholino{4-[6-(3-trifluoromethyl-1-trityl-1H-pyrazolyl)-4-quinolyl]piperazin-1-yl}methanone obtained in Example 193 and 1.5 mL trifluoroacetic acid were reacted in the same manner as in Example 165, to give 66 mg of the title compound as a pale yellow amorphous.
Conditions: See reaction.notes.procedure_details... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1cn[nH]c1 | c1cn[nH]c1 | C1COCC[NH]1.C1C[NH]CC[NH]1.c1ccc2ncccc2c1.c1cn[nH]c1 | Other | null | null | null | O=C(N1CCOCC1)N1CCN(c2ccnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4C(F)(F)F)cc23)CC1>>O=C(N1CCOCC1)N1CCN(c2ccnc3ccc(-c4c[nH]nc4C(F)(F)F)cc23)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-adf4bd1ca14c45bcb01b1ed112ba5ae0 | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(C(=O)N4CCOCC4)CC3)c2c1>>Cc1n[nH]cc1-c1ccc2nccc(N3CCN(C(=O)N4CCOCC4)CC3)c2c1 | CC1=NN(C=C1C=1C=C2C(=CC=NC2=CC1)N1CCN(CC1)C(=O)N1CCOCC1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.Cl>>Cl.CC1=NNC=C1C=1C=C2C(=CC=NC2=CC1)N1CCN(CC1)C(=O)N1CCOCC1 | c1ccc(C(c2ccccc2)(c2ccccc2)[n:4]2[n:3][c:2]([CH3:1])[c:6](-[c:7]3[cH:8][cH:9][c:10]4[n:11][cH:12][cH:13][c:14]([N:15]5[CH2:16][CH2:17][N:18]([C:19](=[O:20])[N:21]6[CH2:22][CH2:23][O:24][CH2:25][CH2:26]6)[CH2:27][CH2:28]5)[c:29]4[cH:30]3)[cH:5]2)cc1>>[CH3:1][c:2]1[n:3][nH:4][cH:5][c:6]1-[c:7]1[cH:8][cH:9][c:10]2[n:11][c... | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(C(=O)N4CCOCC4)CC3)c2c1 | Cc1n[nH]cc1-c1ccc2nccc(N3CCN(C(=O)N4CCOCC4)CC3)c2c1 | null | null | null | Deprotection | OtherReaction | 92b7543875cfe438a4c5cf3faf8e6c828b5eea356096f8ebdcd8d3241dc18933 | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | O=C(N1CCOCC1)N1CCN(c2ccnc3ccc(-c4cn[nH]c4)cc23)CC1 | [#7;a:1]1:[c:2]:[c:3]:[c:4]:[n;H0;D3;+0:5]:1-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#7;a:1]1:[c:2]:[c:3]:[c:4]:[nH;D2;+0:5]:1 | null | [] | null | null | null | null | 90 mg 4-[6-(3-methyl-1-trityl-1H-4-pyrazolyl)-4-quinolyl]piperazin-1-yl-(morpholino)methanone obtained in Example 196 and 1 mL of 5 N hydrochloric acid were reacted in the same manner as in Example 163, to give 36 mg of the title compound as a yellow solid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1cn[nH]c1 | c1cn[nH]c1 | c1cn[nH]c1.c1ccc2ncccc2c1.C1C[NH]CC[NH]1.C1COCC[NH]1 | Other | null | null | null | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(C(=O)N4CCOCC4)CC3)c2c1>>Cc1n[nH]cc1-c1ccc2nccc(N3CCN(C(=O)N4CCOCC4)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e0b88ebbfed6437a920d36f3366795aa | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(C(=O)NCCN(C)C)CC3)c2c1>>Cc1n[nH]cc1-c1ccc2nccc(N3CCN(C(=O)NCCN(C)C)CC3)c2c1 | CN(CCNC(=O)N1CCN(CC1)C1=CC=NC2=CC=C(C=C12)C=1C(=NN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C)C.Cl>>CN(CCNC(=O)N1CCN(CC1)C1=CC=NC2=CC=C(C=C12)C=1C(=NNC1)C)C | c1ccc(C(c2ccccc2)(c2ccccc2)[n:4]2[n:3][c:2]([CH3:1])[c:6](-[c:7]3[cH:8][cH:9][c:10]4[n:11][cH:12][cH:13][c:14]([N:15]5[CH2:16][CH2:17][N:18]([C:19](=[O:20])[NH:21][CH2:22][CH2:23][N:24]([CH3:25])[CH3:26])[CH2:27][CH2:28]5)[c:29]4[cH:30]3)[cH:5]2)cc1>>[CH3:1][c:2]1[n:3][nH:4][cH:5][c:6]1-[c:7]1[cH:8][cH:9][c:10]2[n:11][... | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(C(=O)NCCN(C)C)CC3)c2c1 | Cc1n[nH]cc1-c1ccc2nccc(N3CCN(C(=O)NCCN(C)C)CC3)c2c1 | null | null | null | Deprotection | OtherReaction | 92b7543875cfe438a4c5cf3faf8e6c828b5eea356096f8ebdcd8d3241dc18933 | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | c1cc(N2CCNCC2)c2cc(-c3cn[nH]c3)ccc2n1 | [#7;a:1]1:[c:2]:[c:3]:[c:4]:[n;H0;D3;+0:5]:1-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#7;a:1]1:[c:2]:[c:3]:[c:4]:[nH;D2;+0:5]:1 | 9.4 | [{"value": 9.4, "product": "CN(CCNC(=O)N1CCN(CC1)C1=CC=NC2=CC=C(C=C12)C=1C(=NNC1)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 27 mg N-[2-(dimethylamino)ethyl]-4-[6-(3-methyl-1-trityl-1H-4-pyrazolyl)-4-quinolyl]-1-piperazine carboxamide obtained in Example 197 and 0.32 mL of 5 N hydrochloric acid were reacted in the same manner as in Example 162, to give 1.6 mg of the title compound as a pale yellow solid.
Conditions: See reaction.notes.proced... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1cn[nH]c1 | c1cn[nH]c1 | c1cn[nH]c1.c1ccc2ncccc2c1.C1C[NH]CC[NH]1 | Other | null | null | null | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(C(=O)NCCN(C)C)CC3)c2c1>>Cc1n[nH]cc1-c1ccc2nccc(N3CCN(C(=O)NCCN(C)C)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9164d306f0164298ac7f831a50b2bef4 | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(C(=O)N(C)CCN(C)C)CC3)c2c1>>Cc1n[nH]cc1-c1ccc2nccc(N3CCN(C(=O)N(C)CCN(C)C)CC3)c2c1.Cl | CN(CCN(C(=O)N1CCN(CC1)C1=CC=NC2=CC=C(C=C12)C=1C(=NN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C)C)C.Cl>>Cl.Cl.CN(CCN(C(=O)N1CCN(CC1)C1=CC=NC2=CC=C(C=C12)C=1C(=NNC1)C)C)C | c1ccc(C(c2ccccc2)(c2ccccc2)[n:4]2[n:3][c:2]([CH3:1])[c:6](-[c:7]3[cH:8][cH:9][c:10]4[n:11][cH:12][cH:13][c:14]([N:15]5[CH2:16][CH2:17][N:18]([C:19](=[O:20])[N:21]([CH3:22])[CH2:23][CH2:24][N:25]([CH3:26])[CH3:27])[CH2:28][CH2:29]5)[c:30]4[cH:31]3)[cH:5]2)cc1>>[CH3:1][c:2]1[n:3][nH:4][cH:5][c:6]1-[c:7]1[cH:8][cH:9][c:10... | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(C(=O)N(C)CCN(C)C)CC3)c2c1 | Cc1n[nH]cc1-c1ccc2nccc(N3CCN(C(=O)N(C)CCN(C)C)CC3)c2c1.Cl | null | null | null | Functional Group Interconversion | OtherReaction | f8945b6c47d2fe181548474e648e16cfeefa7d5db2d97918e7510aa55a3c60d6 | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | c1cc(N2CCNCC2)c2cc(-c3cn[nH]c3)ccc2n1 | [#7;a:1]1:[c:2]:[c:3]:[c:4]:[n;H0;D3;+0:5]:1-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#7;a:1]1:[c:2]:[c:3]:[c:4]:[nH;D2;+0:5]:1 | null | [] | null | null | null | null | 67 mg N-[2-(dimethylamino)ethyl]-N-methyl-4-[6-(3-methyl-1-trityl-1H-4-pyrazolyl)-4-quinolyl]-1-piperazine carboxamide obtained in Example 198 and 0.72 mL of 5 N hydrochloric acid were reacted in the same manner as in Example 163, to give 37 mg of the title compound as pale yellow crystals.
Conditions: See reaction.not... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1cn[nH]c1 | c1cn[nH]c1 | c1cn[nH]c1.c1ccc2ncccc2c1.C1C[NH]CC[NH]1 | Other | null | null | null | Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2nccc(N3CCN(C(=O)N(C)CCN(C)C)CC3)c2c1>>Cc1n[nH]cc1-c1ccc2nccc(N3CCN(C(=O)N(C)CCN(C)C)CC3)c2c1.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b74ac904e2ff44ee99694a628a6a8b7a | C[Si](C)(C)CCOCOc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1>>Oc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 | C(C)(=O)OCC.[Cl-].[NH4+].N1=C(C=CC=C1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(C=C2)OCOCC[Si](C)(C)C.CN(P(N(C)C)N(C)C)C>>N1=C(C=CC=C1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(C=C2)O | C[Si](C)(C)CCOC[O:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][n:8]([C:9]([c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)([c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[c:22]3[cH:23][cH:24][cH:25][cH:26][cH:27]3)[cH:28][c:29]2-[c:30]2[cH:31][cH:32][c:33]3[n:34][cH:35][c:36](-[c:37]4[cH:38][cH:39][cH:40][cH:41][n:42]4)[n:43]3[cH:4... | C[Si](C)(C)CCOCOc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 | Oc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 | null | [Cl-].C(CCC)[N+](CCCC)(CCCC)CCCC | O | Reduction | OtherReaction | a260d395a4136e742da746d9351956bea79eaaca1eba544334ae1b2e0c6ec072 | e0b1422bef25db45aecd1b91d52276549faecdaa4ba19e30ce4bb80cad333481 | c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 | C-[Si](-C)(-C)-C-C-O-C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 100.1 | [{"value": 100.1, "product": "N1=C(C=CC=C1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(C=C2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 2 | HOUR | A mixture of 1.23 g 3-(pyridin-2-yl)-6-{3-[4-(2-trimethylsilanylethoxymethoxy)phenyl]-1-trityl-1H-pyrazol-4-yl}imidazo[1,2-a]pyridin (compound in Example 352), 8.5 mL tetrabutylammoniumchloride (1 M tetrahydrofuran solution) and 10 mL hexamethyl phosphorous acid triamide was stirred at 80° C. for 2 hours. Ethyl acetate... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Silyl protective group | Aromatic alcohol | null | null | c1ccccc1.c1c[nH]nc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccn2ccnc2c1.c1ccncc1 | HO- | [Cl-].C(CCC)[N+](CCCC)(CCCC)CCCC.O | 80 | 2 | C[Si](C)(C)CCOCOc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1>[Cl-].C(CCC)[N+](CCCC)(CCCC)CCCC.O>Oc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-733d40a2b793406098e5007d03145a8b | CN(C)C(=O)CCl.Oc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1>>CN(C)C(=O)COc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 | N1=C(C=CC=C1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(C=C2)O.ClCC(=O)N(C)C>>CN(C(COC1=CC=C(C=C1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)C2=NC=CC=C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=O)C | Cl[CH2:6][C:4]([N:2]([CH3:1])[CH3:3])=[O:5].[OH:7][c:8]1[cH:9][cH:10][c:11](-[c:12]2[n:13][n:14]([C:15]([c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)([c:22]3[cH:23][cH:24][cH:25][cH:26][cH:27]3)[c:28]3[cH:29][cH:30][cH:31][cH:32][cH:33]3)[cH:34][c:35]2-[c:36]2[cH:37][cH:38][c:39]3[n:40][cH:41][c:42](-[c:43]4[cH:44][cH:4... | CN(C)C(=O)CCl.Oc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 | CN(C)C(=O)COc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 | Cl-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[C;D1;H3:5])-[C;D1;H3:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C;D1;H3:5]-[#7:4](-[C;D1;H3:6])-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10] | 77.8 | [{"value": 77.8, "product": "CN(C(COC1=CC=C(C=C1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)C2=NC=CC=C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 90 mg 4-{4-[3-(pyridin-2-yl)imidazo[1,2-a]pyridin-6-yl]-1-trityl-1H-pyrazol-3-yl}phenol (compound in Example 353) and 28 mg 2-chloro-N,N-dimethylacetamide were reacted under the same conditions as in Example 190, to give 80 mg of the title compound as a pale yellow amorphous matter.
Conditions: See reaction.notes.proce... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1c[nH]nc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccn2ccnc2c1.c1ccncc1 | HCl | null | null | null | CN(C)C(=O)CCl.Oc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1>>CN(C)C(=O)COc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7b9e373061c54e4fbb41b4aba55e3137 | ClCCN1CCOCC1.Oc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1>>c1ccc(C(c2ccccc2)(c2ccccc2)n2cc(-c3ccc4ncc(-c5ccccn5)n4c3)c(-c3ccc(OCCN4CCOCC4)cc3)n2)cc1 | N1=C(C=CC=C1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(C=C2)O.Cl.ClCCN1CCOCC1>>N1(CCOCC1)CCOC1=CC=C(C=C1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)C2=NC=CC=C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2 | Cl[CH2:42][CH2:43][N:44]1[CH2:45][CH2:46][O:47][CH2:48][CH2:49]1.[cH:1]1[cH:2][cH:3][c:4]([C:5]([c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)([c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[n:18]2[cH:19][c:20](-[c:21]3[cH:22][cH:23][c:24]4[n:25][cH:26][c:27](-[c:28]5[cH:29][cH:30][cH:31][cH:32][n:33]5)[n:34]4[cH:35]3)[c:36](-[... | ClCCN1CCOCC1.Oc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 | c1ccc(C(c2ccccc2)(c2ccccc2)n2cc(-c3ccc4ncc(-c5ccccn5)n4c3)c(-c3ccc(OCCN4CCOCC4)cc3)n2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(C(c2ccccc2)(c2ccccc2)n2cc(-c3ccc4ncc(-c5ccccn5)n4c3)c(-c3ccc(OCCN4CCOCC4)cc3)n2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 58.8 | [{"value": 58.8, "product": "N1(CCOCC1)CCOC1=CC=C(C=C1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)C2=NC=CC=C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 90 mg 4-{4-[3-(pyridin-2-yl)imidazo[1,2-a]pyridin-6-yl]-1-trityl-1H-pyrazol-3-yl}phenol (compound in Example 353) and 42 mg N-(2-chloroethyl)morpholine hydrochloride were reacted under the same conditions as in Example 190, to give 63 mg of the title compound as a colorless amorphous matter.
Conditions: See reaction.no... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1cn[nH]c1.c1ccn2ccnc2c1.c1ccncc1.c1ccccc1.C1COCC[NH]1 | HCl | null | null | null | ClCCN1CCOCC1.Oc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1>>c1ccc(C(c2ccccc2)(c2ccccc2)n2cc(-c3ccc4ncc(-c5ccccn5)n4c3)c(-c3ccc(OCCN4CCOCC4)cc3)n2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dc1802b6f513472bae8855d9e31bf0c9 | CI.O=C(Nc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1)N1CCOCC1>>CN(C(=O)N1CCOCC1)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 | [H-].[Na+].O.N1=C(C=CC=C1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(C=C2)NC(=O)N2CCOCC2.CI>>CN(C(=O)N1CCOCC1)C1=CC=C(C=C1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)C2=NC=CC=C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2 | I[CH3:1].[NH:2]([C:3](=[O:4])[N:5]1[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1)[c:11]1[cH:12][cH:13][c:14](-[c:15]2[n:16][n:17]([C:18]([c:19]3[cH:20][cH:21][cH:22][cH:23][cH:24]3)([c:25]3[cH:26][cH:27][cH:28][cH:29][cH:30]3)[c:31]3[cH:32][cH:33][cH:34][cH:35][cH:36]3)[cH:37][c:38]2-[c:39]2[cH:40][cH:41][c:42]3[n:43][cH:44][c:4... | CI.O=C(Nc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1)N1CCOCC1 | CN(C(=O)N1CCOCC1)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 13a6df5c30362480aaf35df663931fc9e05b0e4795988833791ca09b44bcf7cb | 4cfa26ee27b218487d99804efc5ef484ef0015788159cacae14b57c0fb8e7fb5 | O=C(Nc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1)N1CCOCC1 | I-[CH3;D1;+0:1].[C:2]-[#7:3](-[C:4](=[O;D1;H0:5])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[C:10]>>[C:2]-[#7:3](-[C:4](=[O;D1;H0:5])-[N;H0;D3;+0:6](-[CH3;D1;+0:1])-[c:7](:[c:8]):[c:9])-[C:10] | null | [] | null | null | 20 | MINUTE | 6 mg sodium hydride was suspended in 2 mL N,N-dimethylformamide, then 3 mL of 64 mg morpholine-4-carboxylic acid {4-[4-(3-pyridin-2-ylimidazo[1,2-a]-pyridin-6-yl)-1-trityl-1H-pyrazol-3-yl]phenyl}amide (compound in Example 357) in N,N-dimethylformamide was added thereto under ice-coolingd water in a stream of nitrogen, ... | 10.6084/m9.figshare.5104873.v1 | null | Urea | Urea | null | null | C1COCC[NH]1.c1ccccc1.c1c[nH]nc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccn2ccnc2c1.c1ccncc1 | HI | CN(C=O)C.C(C)(=O)OCC | null | 0.333333 | CI.O=C(Nc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1)N1CCOCC1>CN(C=O)C.C(C)(=O)OCC>CN(C(=O)N1CCOCC1)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-97113197092d4cb7b2ccc7d93b9455fb | CCOC(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2B2OC(C)(C)C(C)(C)O2)cc1.COC(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1>>CCOC(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 | BrC=1C=CC=2N(C1)C(=CN2)C2=NC=CC=C2.CC1(OB(OC1(C)C)C=1C(=NN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=C(C(=O)OC)C=C1)C.CC1(OB(OC1(C)C)C=1C(=NN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=C(C(=O)OCC)C=C1)C.N1=C(C=CC=C1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(C(=O)OC)C=C2>>N... | CC1(C)OB([c:33]2[c:10](-[c:9]3[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:50][cH:49]3)[n:11][n:12]([C:13]([c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)([c:20]3[cH:21][cH:22][cH:23][cH:24][cH:25]3)[c:26]3[cH:27][cH:28][cH:29][cH:30][cH:31]3)[cH:32]2)OC1(C)C.COC(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-... | CCOC(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2B2OC(C)(C)C(C)(C)O2)cc1.COC(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 | CCOC(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 | null | null | null | C-C Coupling | C-methylation | ab41afcc079fcc0b26e73e85c8a5361c76133b05823bffbfeb43182a7190a730 | a4a0ce4ded919d3fef2bba82b7959d06b55c29d0a47e267a7ef1d83e16635a8b | c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 | C-C1(-C)-O-B(-[c;H0;D3;+0:1]2:[c:2]:[#7;a:3](-[C:4]):[#7;a:5]:[c:6]:2-[c:7])-O-C-1(-C)-C.C-O-C(=O)-c1:c:c:c(-c2:n:n(-C(-c3:c:c:c:c:c:3)(-c3:c:c:c:c:c:3)-c3:c:c:c:c:c:3):c:c:2-[c;H0;D3;+0:8]2:[c:9]:[c:10]:[c:11]3:[#7;a:12]:[c:13]:[c:14]:[#7;a:15]:3:[c:16]:2):c:c:1>>[C:4]-[#7;a:3]1:[#7;a:5]:[c:6](-[c:7]):[c;H0;D3;+0:1](-... | null | [] | null | null | null | null | 2 g 6-bromo-3-(2-pyridyl)imidazo[1,2-a]pyridine (compound in Production Example 63) and 5 g mixture of methyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-trityl-1H-3-pyrazolyl]benzoate and ethyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-trityl-1H-3-pyrazolyl]benzoate were reacted in the same manner ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boronic ester | null | B1OCCO1.c1c[nH]nc1.c1ccccc1.c1cn[nH]c1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccn2ccnc2c1 | c1c[nH]nc1.c1ccn2ccnc2c1 | c1ccccc1.c1c[nH]nc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccn2ccnc2c1.c1ccncc1 | HO-.B | null | null | null | CCOC(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2B2OC(C)(C)C(C)(C)O2)cc1.COC(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1>>CCOC(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ddfccf8ab1374fd687a6ff99a69c6290 | CCOC(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1>>OCc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 | O.N1=C(C=CC=C1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(C(=O)OCC)C=C2.[H-].[Al+3].[Li+].[H-].[H-].[H-].[F-].[Na+].O>>N1=C(C=CC=C1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(C=C2)CO | CCO[C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][n:9]([C:10]([c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)([c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[c:23]3[cH:24][cH:25][cH:26][cH:27][cH:28]3)[cH:29][c:30]2-[c:31]2[cH:32][cH:33][c:34]3[n:35][cH:36][c:37](-[c:38]4[cH:39][cH:40][cH:41][cH:42][n:43]4)[n:44]3[cH:45]2... | CCOC(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 | OCc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 | null | null | O1CCCC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | 49.9 | [{"value": 49.9, "product": "N1=C(C=CC=C1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(C=C2)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 2 | HOUR | 2 g 6-bromo-3-(2-pyridyl)imidazo[1,2-a]pyridine (compound in Production Example 63) and 5 g mixture of methyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-trityl-1H-3-pyrazolyl]benzoate and ethyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-trityl-1H-3-pyrazolyl]benzoate were reacted in the same manner ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1.c1c[nH]nc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccn2ccnc2c1.c1ccncc1 | HO- | O1CCCC1 | 50 | 2 | CCOC(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1>O1CCCC1>OCc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6f2625f410d3427fb21178384597dbb8 | CNC.OCc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1>>CN(C)Cc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 | N1=C(C=CC=C1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(C=C2)CO.CNC>>CN(CC1=CC=C(C=C1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)C2=NC=CC=C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C | [CH3:1][NH:2][CH3:3].O[CH2:4][c:5]1[cH:6][cH:7][c:8](-[c:9]2[n:10][n:11]([C:12]([c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)([c:19]3[cH:20][cH:21][cH:22][cH:23][cH:24]3)[c:25]3[cH:26][cH:27][cH:28][cH:29][cH:30]3)[cH:31][c:32]2-[c:33]2[cH:34][cH:35][c:36]3[n:37][cH:38][c:39](-[c:40]4[cH:41][cH:42][cH:43][cH:44][n:45]4)... | CNC.OCc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 | CN(C)Cc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 | null | [O-2].[Mn+4].[O-2] | C(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | f33a8d71b7dbaa463dcb87d1e5073e084c21a5fbc935ce82a22b6d65293f45d1 | 87693a475e46c41583976158ec46dcaf8be8cc05c5635654a6a68033770f8d5c | c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7]>>[C;D1;H3:5]-[N;H0;D3;+0:6](-[C;D1;H3:7])-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | A mixture of 296 mg {4-[4-(3-pyridin-2-ylimidazo[1,2-a]pyridin-6-yl)-1-trityl-1H-pyrazol-3-yl]phenyl}methanol (compound in Example 359), 844 mg manganese (IV) oxide and 20 mL chloroform was heated for 1 hour under reflux. The reaction solution was cooled to remove insolubles, and the filtrate was evaporated. 264 mg cru... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Secondary amine | Tertiary amine | null | null | c1ccccc1.c1c[nH]nc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccn2ccnc2c1.c1ccncc1 | HO- | [O-2].[Mn+4].[O-2].C(Cl)(Cl)Cl | null | null | CNC.OCc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1>[O-2].[Mn+4].[O-2].C(Cl)(Cl)Cl>CN(C)Cc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccn4)n3c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4cb83f7b081542a18c833fe5a28d29f9 | COC(=O)c1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2ncc(-c3ccccn3)n2c1>>O=C(O)c1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2ncc(-c3ccccn3)n2c1 | N1=C(C=CC=C1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C(=O)OC.[OH-].[Na+].CO.[Cl-].[NH4+]>>N1=C(C=CC=C1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C(=O)O | C[O:3][C:2](=[O:1])[c:4]1[n:5][n:6]([C:7]([c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)([c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[cH:26][c:27]1-[c:28]1[cH:29][cH:30][c:31]2[n:32][cH:33][c:34](-[c:35]3[cH:36][cH:37][cH:38][cH:39][n:40]3)[n:41]2[cH:42]1>>[O:1]=[C:2]([OH:3])[c:4... | COC(=O)c1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2ncc(-c3ccccn3)n2c1 | O=C(O)c1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2ncc(-c3ccccn3)n2c1 | null | null | O1CCCC1.O.C(C)(=O)OCC | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(C(c2ccccc2)(c2ccccc2)n2cc(-c3ccc4ncc(-c5ccccn5)n4c3)cn2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#7;a:5]:[#7;a:6]>>[#7;a:6]:[#7;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 77.4 | [{"value": 77.4, "product": "N1=C(C=CC=C1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 4 | HOUR | A mixture of 228 mg methyl 4-[3-(pyridin-2-yl)imidazo-[1,2-a]pyridin-6-yl]-1-trityl-1H-pyrazole-3-carboxylate (compound in Example 366), 0.8 mL of 1 N aqueous sodium hydroxide, 5 mL methanol and 3 mL tetrahydrofuran was stirred at 50° C. for 4 hours. Saturated ammonium chloride, ethyl acetate and water were added to th... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1c[nH]nc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccn2ccnc2c1.c1ccncc1 | Other | O1CCCC1.O.C(C)(=O)OCC | 50 | 4 | COC(=O)c1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2ncc(-c3ccccn3)n2c1>O1CCCC1.O.C(C)(=O)OCC>O=C(O)c1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1-c1ccc2ncc(-c3ccccn3)n2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8283f3caa79d40a494434f9ecf3a4b04 | COC(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccc(SC)s4)n3c2)cc1.CSc1ccc(-c2cnc3ccc(Br)cn23)s1>>CCOC(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccc(SC)s4)n3c2)cc1 | BrC=1C=CC=2N(C1)C(=CN2)C=2SC(=CC2)SC.CC1(OB(OC1(C)C)C=1C(=NN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=C(C(=O)OC)C=C1)C.CC1(OB(OC1(C)C)C=1C(=NN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=C(C(=O)OC)C=C1)C.CSC1=CC=C(S1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(C(=O)OC)C=C2>>... | c1cc2ncc(-c3ccc(S[CH3:1])s3)n2cc1-[c:33]1[c:10](-[c:9]2[cH:8][cH:7][c:6]([C:4]([O:3][CH3:2])=[O:5])[cH:51][cH:50]2)[n:11][n:12]([C:13]([c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)([c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[c:26]2[cH:27][cH:28][cH:29][cH:30][cH:31]2)[cH:32]1.Br[c:34]1[cH:35][cH:36][c:37]2[n:38][cH:39]... | COC(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccc(SC)s4)n3c2)cc1.CSc1ccc(-c2cnc3ccc(Br)cn23)s1 | CCOC(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccc(SC)s4)n3c2)cc1 | null | null | null | C-C Coupling | C-methylation | 2bb3c86bf6cdf9ae1a0dd3efc320615ac6b484f69e5e6af560fede1dca0be410 | 966413f7a968ef97666549a121e5611ef8ff9a1971a51d137266f1c00cd0abd8 | c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4cccs4)n3c2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:2:[c:9]:1.[CH3;D1;+0:10]-[#8:11]-[C:12](=[O;D1;H0:13])-[c:14].[C:15]-[#7;a:16]1:[#7;a:17]:[c:18](-[c:19]):[c;H0;D3;+0:20](-c2:c:c:c3:n:c:c(-c4:c:c:c(-S-[CH3;D1;+0:21]):s:4):n:3:c:2):[c:22]:1>>[CH3;D1;+0:21]-[CH2;D2;+0:10]-[#8:11]-[C:12](=[O;D1;H0:13])-... | null | [] | null | null | null | null | 260 mg 6-bromo-3-[5-(methylsulfanyl)-2-thienyl]imidazo[1,2-a]pyridine (compound in Production Example 58) and 1 g mixture of methyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-trityl-1H-3-pyrazolyl]benzoate and methyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-trityl-1H-3-pyrazolyl]benzoate were reac... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Monosulfide | Ester | c1ccn2ccnc2c1.c1ccsc1.c1c[nH]nc1.c1ccn2ccnc2c1 | c1c[nH]nc1.c1ccn2ccnc2c1 | c1ccccc1.c1c[nH]nc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccn2ccnc2c1.c1ccsc1 | HBr | null | null | null | COC(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccc(SC)s4)n3c2)cc1.CSc1ccc(-c2cnc3ccc(Br)cn23)s1>>CCOC(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccc(SC)s4)n3c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bc57ab5fcfb14623a8ba0cbfcc62fd66 | CCOC(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccc(SC)s4)n3c2)cc1>>CSc1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(CO)cc4)cn23)s1 | CSC1=CC=C(S1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(C(=O)OC)C=C2.CSC1=CC=C(S1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(C(=O)OCC)C=C2>>CSC1=CC=C(S1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(C=C2)CO | CCO[C:42]([c:41]1[cH:40][cH:39][c:38](-[c:37]2[c:14](-[c:13]3[cH:12][cH:11][c:10]4[n:9][cH:8][c:7](-[c:6]5[cH:5][cH:4][c:3]([S:2][CH3:1])[s:48]5)[n:47]4[cH:46]3)[cH:15][n:16]([C:17]([c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)([c:24]3[cH:25][cH:26][cH:27][cH:28][cH:29]3)[c:30]3[cH:31][cH:32][cH:33][cH:34][cH:35]3)[n:36... | CCOC(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccc(SC)s4)n3c2)cc1 | CSc1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(CO)cc4)cn23)s1 | null | null | null | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4cccs4)n3c2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | 124 mg of the title compound was obtained as a pale yellow solid by the same method as in Example 359 from 196 mg of the mixture of methyl 4-{4-[3-(5-methylsulfanylthiophen-2-yl)-imidazo[1,2-a]pyridin-6-yl]-1-trityl-1H-pyrazol-3-yl}benzoate and ethyl 4-{4-[3-(5-methylsulfanylthiophen-2-yl)imidazo[1,2-a]pyridin-6-yl]-1-... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccsc1.c1ccn2ccnc2c1.c1cn[nH]c1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CCOC(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccc(SC)s4)n3c2)cc1>>CSc1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(CO)cc4)cn23)s1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-500e04ed0fc24c0e9e738faa257c8af8 | CCOC(=O)CCCCCCBr.Oc1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1>>CCOC(=O)CCCCCCOc1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1 | FC1=CC=C(C=C1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)C2=CC=C(C=C2)O)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2.BrCCCCCCC(=O)OCC.I(=O)(=O)[O-].[Na+].C([O-])([O-])=O.[K+].[K+]>>FC1=CC=C(C=C1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)C2=CC=C(OCCCCCCC(=O)OCC)C=C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2 | Br[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[OH:12][c:13]1[cH:14][cH:15][c:16](-[c:17]2[cH:18][n:19][c:20]3[cH:21][cH:22][c:23](-[c:24]4[cH:25][n:26]([C:27]([c:28]5[cH:29][cH:30][cH:31][cH:32][cH:33]5)([c:34]5[cH:35][cH:36][cH:37][cH:38][cH:39]5)[c:40]5[cH:41][cH:42][cH:43][cH:44][cH:... | CCOC(=O)CCCCCCBr.Oc1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1 | CCOC(=O)CCCCCCOc1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1 | null | null | O.CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4ccccc4)n3c2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 62.6 | [{"value": 62.6, "product": "FC1=CC=C(C=C1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)C2=CC=C(OCCCCCCC(=O)OCC)C=C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 8 | HOUR | A mixture of 200 mg 4-{6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]imidazo[1,2-a]pyridin-3-yl}phenol (compound in Example 14), 232 mg ethyl 7-bromoheptanoate, 6 mg sodium iodate, 68 mg potassium carbonate, and 15 mL N,N-dimethylformamide was stirred overnight at 80° C. Ethyl acetate and water were added to the reacti... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccn2ccnc2c1.c1cn[nH]c1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HBr | O.CN(C=O)C.C(C)(=O)OCC | 80 | 8 | CCOC(=O)CCCCCCBr.Oc1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1>O.CN(C=O)C.C(C)(=O)OCC>CCOC(=O)CCCCCCOc1ccc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9f9a04dd3f434f1c9a3c9edb8338bd2d | CI.NNC(=O)c1cnc2ccc(-c3cn(C(c4ccccc4)(c4ccccc4)c4ccccc4)nc3-c3ccc(F)cc3)cn12.S=C=S>>CSc1nnc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)o1 | C([O-])([O-])=O.[K+].[K+].CI.[Cl-].[NH4+].FC1=CC=C(C=C1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)C(=O)NN)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2.[OH-].[Na+].C(=S)=S>>FC1=CC=C(C=C1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)C=2OC(=NN2)SC)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2 | I[CH3:1].[NH2:4][NH:5][C:6]([c:7]1[cH:8][n:9][c:10]2[cH:11][cH:12][c:13](-[c:14]3[cH:15][n:16]([C:17]([c:18]4[cH:19][cH:20][cH:21][cH:22][cH:23]4)([c:24]4[cH:25][cH:26][cH:27][cH:28][cH:29]4)[c:30]4[cH:31][cH:32][cH:33][cH:34][cH:35]4)[n:36][c:37]3-[c:38]3[cH:39][cH:40][c:41]([F:42])[cH:43][cH:44]3)[cH:45][n:46]12)=[O:... | CI.NNC(=O)c1cnc2ccc(-c3cn(C(c4ccccc4)(c4ccccc4)c4ccccc4)nc3-c3ccc(F)cc3)cn12.S=C=S | CSc1nnc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)o1 | null | null | O.C(C)(=O)OCC.O1CCCC1.CN(C=O)C.C(C)O | Aromatic Heterocycle Formation | OtherReaction | a15f2bb205835a52a07e1d5735ecf8c10312f9f9f9bd5bc3c4fe361d9edeb208 | 2490f837e85471307bcfdf18fc468adc3367e4e60eef0d0c8d14c76d34701a72 | c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4nnco4)n3c2)cc1 | I-[CH3;D1;+0:1].S=[C;H0;D2;+0:2]=[S;H0;D1;+0:3].[NH2;D1;+0:4]-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-[c;H0;D3;+0:8]1:[c:9]:[#7;a:10]:[c:11](:[c:12]):[#7;a:13]:1:[c:14]>>[CH3;D1;+0:1]-[S;H0;D2;+0:3]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:4]:[n;H0;D2;+0:5]:[c;H0;D3;+0:6](-[c;H0;D3;+0:8]2:[c:9]:[#7;a:10]:[c:11](:[c:12]):[#7;a:... | null | [] | null | null | 10 | MINUTE | A mixture of 283 mg 6-[3-(4-fluorophenyl)-1-trityl-1H-pyrazol-4-yl]imidazo[1,2-a]pyridine-3-carboxylic acid hydrazide (compound in Production Example 274), 38 mg carbon disulfide, 20 mg sodium hydroxide, 5 mL ethanol and 5 mL water was heated for 4 hours under reflux. Ethyl acetate, tetrahydrofuran and an aqueous satur... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine | Monosulfide | null | c1nnco1 | c1nnco1.c1ccn2ccnc2c1.c1cn[nH]c1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HI | O.C(C)(=O)OCC.O1CCCC1.CN(C=O)C.C(C)O | null | 0.166667 | CI.NNC(=O)c1cnc2ccc(-c3cn(C(c4ccccc4)(c4ccccc4)c4ccccc4)nc3-c3ccc(F)cc3)cn12.S=C=S>O.C(C)(=O)OCC.O1CCCC1.CN(C=O)C.C(C)O>CSc1nnc(-c2cnc3ccc(-c4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)nc4-c4ccc(F)cc4)cn23)o1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-867b0a31188c4f479c781a6d85d46632 | Fc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2cc(Cl)c3ncc(-c4nccs4)n3c2)cc1>>N#Cc1cc(-c2cn(C(c3ccccc3)(c3ccccc3)c3ccccc3)nc2-c2ccc(F)cc2)cn2c(-c3nccs3)cnc12 | ClC=1C=2N(C=C(C1)C=1C(=NN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=C(C=C1)F)C(=CN2)C=2SC=CN2.CN(C(C)=O)C>>FC1=CC=C(C=C1)C1=NN(C=C1C=1C=C(C=2N(C1)C(=CN2)C=2SC=CN2)C#N)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2 | Cl[c:3]1[cH:4][c:5](-[c:6]2[cH:7][n:8]([C:9]([c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)([c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[c:22]3[cH:23][cH:24][cH:25][cH:26][cH:27]3)[n:28][c:29]2-[c:30]2[cH:31][cH:32][c:33]([F:34])[cH:35][cH:36]2)[cH:37][n:38]2[c:39](-[c:40]3[n:41][cH:42][cH:43][s:44]3)[cH:45][n:46][c:47]1... | Fc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2cc(Cl)c3ncc(-c4nccs4)n3c2)cc1 | N#Cc1cc(-c2cn(C(c3ccccc3)(c3ccccc3)c3ccccc3)nc2-c2ccc(F)cc2)cn2c(-c3nccs3)cnc12 | null | [C-]#N.[Zn+2].[C-]#N.[Zn].C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)[C-]1C=CC=C1.[CH-]1C=CC=C1.[Fe+2] | O.C(C)(=O)OCC | Miscellaneous | OtherReaction | d74ca4eb01de054d853964e9e783237743e5ce2dbe3364089208cc9279fe54a1 | 73a96fe5e833259ca394a42f82d6cc2ee7231bcde92d95030d2893b90c3fef76 | c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4nccs4)n3c2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]2:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:1>>[N;D1;H0:10]#[C:11]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]2:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:1 | null | [] | 150 | CELSIUS | null | null | A solution of 213 mg 2-{8-chloro-6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]imidazo[1,2-a]pyridin-3-yl}-1,3-thiazole obtained in Example 404 in 2 mL N,N-dimethylacetamide, together with 24 mg zinc cyanide, 6 mg zinc powder, 12 mg tris(dibenzylidene acetone)dipalladium (0) and 15 mg diphenylphosphinoferrocene, was he... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1ccn2ccnc2c1 | c1ccn2ccnc2c1 | c1cn[nH]c1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1cscn1.c1ccn2ccnc2c1 | null | [C-]#N.[Zn+2].[C-]#N.[Zn].C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)[C-]1C=CC=C1.[CH-]1C=CC=C1.[Fe+2].O.C(C)(=O)OCC | 150 | null | Fc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2cc(Cl)c3ncc(-c4nccs4)n3c2)cc1>[C-]#N.[Zn+2].[C-]#N.[Zn].C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)[C-]1C=CC=C1.[CH-]1C=CC=C1.[Fe+2].O.C(C)(=O)OCC>N#Cc1cc(-c... |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a60b2d0c17744fa783349fd6aea95e60 | Brc1ccc2ncc(-c3noc(C4CC4)n3)n2c1.COc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2B2OC(C)(C)C(C)(C)O2)c(F)c1>>COc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4noc(C5CC5)n4)n3c2)c(F)c1 | O.BrC=1C=CC=2N(C1)C(=CN2)C2=NOC(=N2)C2CC2.FC1=C(C=CC(=C1)OC)C1=NN(C=C1B1OC(C(O1)(C)C)(C)C)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.O.P(=O)([O-])([O-])[O-].[K+].[K+].[K+]>>C1(CC1)C1=NC(=NO1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=C(C=C(C=C2)OC)F | Br[c:31]1[cH:32][cH:33][c:34]2[n:35][cH:36][c:37](-[c:38]3[n:39][o:40][c:41]([CH:42]4[CH2:43][CH2:44]4)[n:45]3)[n:46]2[cH:47]1.CC1(C)OB([c:30]2[c:7](-[c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:50][c:48]3[F:49])[n:8][n:9]([C:10]([c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)([c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[c:23... | Brc1ccc2ncc(-c3noc(C4CC4)n3)n2c1.COc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2B2OC(C)(C)C(C)(C)O2)c(F)c1 | COc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4noc(C5CC5)n4)n3c2)c(F)c1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | CN(C=O)C.C(C)(=O)OCC | C-C Coupling | Suzuki coupling with boronic esters | f0a81b46b65bd661906d6acd7a929547dd2c9e1627a7618688b4369c11b8233f | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4noc(C5CC5)n4)n3c2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:2:[c:9]:1.C-C1(-C)-O-B(-[c;H0;D3;+0:10]2:[c:11]:[#7;a:12](-[C:13]):[#7;a:14]:[c:15]:2-[c:16])-O-C-1(-C)-C>>[C:13]-[#7;a:12]1:[#7;a:14]:[c:15](-[c:16]):[c;H0;D3;+0:10](-[c;H0;D3;+0:1]2:[c:2]:[c:3]:[c:4]3:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:3:[c:9]:2):[c:11]:1 | 73.4 | [{"value": 73.4, "product": "C1(CC1)C1=NC(=NO1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=C(C=C(C=C2)OC)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 82 mg 6-bromo-3-(5-cyclopropyl-[1,2,4]oxadiazol-3-yl)-imidazo[1,2-a]pyridine (compound in Production Example 255), 227 mg 3-(2-fluoro-4-methoxyphenyl)-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-trityl-1H-pyrazole (compound in Production Example 185), 86 mg tripotassium phosphate hydrate and 31 mg tetrakis(triph... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | c1ccn2ccnc2c1.B1OCCO1.c1c[nH]nc1 | c1c[nH]nc1.c1ccn2ccnc2c1 | c1ccccc1.c1c[nH]nc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccn2ccnc2c1.c1ncon1.C1CC1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.CN(C=O)C.C(C)(=O)OCC | null | null | Brc1ccc2ncc(-c3noc(C4CC4)n3)n2c1.COc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2B2OC(C)(C)C(C)(C)O2)c(F)c1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.CN(C=O)C.C(C)(=O)OCC>COc1ccc(-c2nn(C(c3ccc... |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3fc754ced135477ab9603d9cc21b95dc | N#Cc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4nccs4)n3c2)s1.[N-]=[N+]=[N-]>>c1ccc(C(c2ccccc2)(c2ccccc2)n2cc(-c3ccc4ncc(-c5nccs5)n4c3)c(-c3ccc(-c4nnn[nH]4)s3)n2)cc1 | O.[N-]=[N+]=[N-].[Na+].[Cl-].[NH4+].[N-]=[N+]=[N-].[Na+].[Cl-].[NH4+].S1C(=NC=C1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(S2)C#N>>N1N=NN=C1C1=CC=C(S1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)C=2SC=CN2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2 | [cH:1]1[cH:2][cH:3][c:4]([C:5]([c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)([c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[n:18]2[cH:19][c:20](-[c:21]3[cH:22][cH:23][c:24]4[n:25][cH:26][c:27](-[c:28]5[n:29][cH:30][cH:31][s:32]5)[n:33]4[cH:34]3)[c:35](-[c:36]3[cH:37][cH:38][c:39]([C:40]#[N:41])[s:45]3)[n:46]2)[cH:47][cH:48]1.... | N#Cc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4nccs4)n3c2)s1.[N-]=[N+]=[N-] | c1ccc(C(c2ccccc2)(c2ccccc2)n2cc(-c3ccc4ncc(-c5nccs5)n4c3)c(-c3ccc(-c4nnn[nH]4)s3)n2)cc1 | null | null | CN(C=O)C | Aromatic Heterocycle Formation | OtherReaction | 237b84aaa459abf427f233dc6a07a1d9de824f980714e458423189bb68f60f12 | d8c808528b7ee68720aaeebd35cb6a2a30e344748d0066102cdae99843b93cf0 | c1ccc(C(c2ccccc2)(c2ccccc2)n2cc(-c3ccc4ncc(-c5nccs5)n4c3)c(-c3ccc(-c4nnn[nH]4)s3)n2)cc1 | [N-;H0;D1:1]=[N+;H0;D2:2]=[N-;H0;D1:3].[N;H0;D1;+0:4]#[C;H0;D2;+0:5]-[c;H0;D3;+0:6]1:[#16;a:7]:[c:8]:[c:9]:[c:10]:1>>[#16;a:7]1:[c:8]:[c:9]:[c:10]:[c;H0;D3;+0:6]:1-[c;H0;D3;+0:5]1:[n;H0;D2;+0:4]:[n;H0;D2;+0:1]:[n;H0;D2;+0:2]:[nH;D2;+0:3]:1 | 56.1 | [{"value": 56.1, "product": "N1N=NN=C1C1=CC=C(S1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)C=2SC=CN2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 18 | HOUR | 100 mg 5-[4-(3-thiazol-2-yl-imidazo[1,2-a]pyridin-6-yl)-1-trityl-1H-pyrazol-3-yl]-thiophen-2-carbonitrile (compound in Example 440) was dissolved in 3 mL N,N-dimethylformamide, and 12 mg sodium azide and 9.5 mg ammonium chloride were added thereto and stirred at 100° C. for 18 hours in a stream of nitrogen. 24 mg sodiu... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | null | null | c1nnn[nH]1 | c1ccccc1.c1ccccc1.c1ccccc1.c1cn[nH]c1.c1ccn2ccnc2c1.c1cscn1.c1ccsc1.c1nnn[nH]1 | null | CN(C=O)C | 100 | 18 | N#Cc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4nccs4)n3c2)s1.[N-]=[N+]=[N-]>CN(C=O)C>c1ccc(C(c2ccccc2)(c2ccccc2)n2cc(-c3ccc4ncc(-c5nccs5)n4c3)c(-c3ccc(-c4nnn[nH]4)s3)n2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c453be8c9efc4469a0508b0dcac3dd58 | Brc1ccc2ncc(-c3nccs3)n2c1.COC(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2B2OC(C)(C)C(C)(C)O2)s1>>COC(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4nccs4)n3c2)s1 | CC1(OB(OC1(C)C)C=1C(=NN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=C(S1)C(=O)OC)C.BrC=1C=CC=2N(C1)C(=CN2)C=2SC=CN2.P(=O)([O-])([O-])[O-].[K+].[K+].[K+]>>S1C(=NC=C1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(S2)C(=O)OC | Br[c:33]1[cH:34][cH:35][c:36]2[n:37][cH:38][c:39](-[c:40]3[n:41][cH:42][cH:43][s:44]3)[n:45]2[cH:46]1.CC1(C)OB([c:32]2[c:9](-[c:8]3[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[s:47]3)[n:10][n:11]([C:12]([c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)([c:19]3[cH:20][cH:21][cH:22][cH:23][cH:24]3)[c:25]3[cH:26][cH:27][cH:28]... | Brc1ccc2ncc(-c3nccs3)n2c1.COC(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2B2OC(C)(C)C(C)(C)O2)s1 | COC(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4nccs4)n3c2)s1 | null | null | CN(C=O)C | C-C Coupling | Suzuki coupling with boronic esters | f0a81b46b65bd661906d6acd7a929547dd2c9e1627a7618688b4369c11b8233f | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | c1ccc(C(c2ccccc2)(c2ccccc2)n2cc(-c3ccc4ncc(-c5nccs5)n4c3)c(-c3cccs3)n2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:2:[c:9]:1.C-C1(-C)-O-B(-[c;H0;D3;+0:10]2:[c:11]:[#7;a:12](-[C:13]):[#7;a:14]:[c:15]:2-[c:16]:[#16;a:17])-O-C-1(-C)-C>>[#16;a:17]:[c:16]-[c:15]1:[#7;a:14]:[#7;a:12](-[C:13]):[c:11]:[c;H0;D3;+0:10]:1-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[#7;a:5]:[c:6]:[c:7... | 86.2 | [{"value": 86.2, "product": "S1C(=NC=C1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(S2)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1.6 g methyl 5-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-trityl-1H-3-pyrazolyl]-2-thiophene carboxylate (compound in Production Example 117), 0.6 g 2-(6-bromoimidazo[1,2-a]pyridin-3-yl)-1,3-thiazole (compound in Production Example 57), 0.68 g tripotassium phosphate, 0.12 g tetrakis (triphenylphosphine)palladiu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | c1ccn2ccnc2c1.B1OCCO1.c1c[nH]nc1 | c1c[nH]nc1.c1ccn2ccnc2c1 | c1ccsc1.c1c[nH]nc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccn2ccnc2c1.c1cscn1 | HBr.B | CN(C=O)C | null | null | Brc1ccc2ncc(-c3nccs3)n2c1.COC(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2B2OC(C)(C)C(C)(C)O2)s1>CN(C=O)C>COC(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4nccs4)n3c2)s1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0775a214685d4d79b73aba71e9b6fd1b | COC(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4nccs4)n3c2)s1>>O=C(O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4nccs4)n3c2)s1 | S1C(=NC=C1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(S2)C(=O)OC.[OH-].[Li+].C(C)O.Cl>>S1C(=NC=C1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(S2)C(=O)O | C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[n:9][n:10]([C:11]([c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)([c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[c:24]3[cH:25][cH:26][cH:27][cH:28][cH:29]3)[cH:30][c:31]2-[c:32]2[cH:33][cH:34][c:35]3[n:36][cH:37][c:38](-[c:39]4[n:40][cH:41][cH:42][s:43]4)[n:44]3[cH:45]2)[s:... | COC(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4nccs4)n3c2)s1 | O=C(O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4nccs4)n3c2)s1 | null | null | O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(C(c2ccccc2)(c2ccccc2)n2cc(-c3ccc4ncc(-c5nccs5)n4c3)c(-c3cccs3)n2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#16;a:5]>>[#16;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 92 | [{"value": 92.0, "product": "S1C(=NC=C1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(S2)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1.20 g methyl 5-{4-[3-(1,3-thiazol-2-yl)imidazo-[1,2-a)pyridin-6-yl]-1-trityl-1H-3-pyrazolyl}-2-thiophene carboxylate obtained in Example 442, 0.16 g lithium hydroxide, 30 mL ethanol and 15 mL water were heated at 85° C. for 5 hours. Under ice-cooling, the reaction solution was neutralized by adding water and 1 N aqueo... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccsc1.c1c[nH]nc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccn2ccnc2c1.c1cscn1 | Other | O | null | null | COC(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4nccs4)n3c2)s1>O>O=C(O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4nccs4)n3c2)s1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7f5fc539321f45eca307cded64465912 | CNC.O=C(O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4nccs4)n3c2)s1>>CN(C)C(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4nccs4)n3c2)s1 | CNC.S1C(=NC=C1)C1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(S2)C(=O)O.C(C)N(CC)CC.ClC(=O)OCC(C)C.O1CCCC1>>CN(C(=O)C=1SC(=CC1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)C=2SC=CN2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C | [CH3:1][NH:2][CH3:3].O[C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9](-[c:10]2[n:11][n:12]([C:13]([c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)([c:20]3[cH:21][cH:22][cH:23][cH:24][cH:25]3)[c:26]3[cH:27][cH:28][cH:29][cH:30][cH:31]3)[cH:32][c:33]2-[c:34]2[cH:35][cH:36][c:37]3[n:38][cH:39][c:40](-[c:41]4[n:42][cH:43][cH:44][s:45]4)[... | CNC.O=C(O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4nccs4)n3c2)s1 | CN(C)C(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4nccs4)n3c2)s1 | null | null | O | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | c1ccc(C(c2ccccc2)(c2ccccc2)n2cc(-c3ccc4ncc(-c5nccs5)n4c3)c(-c3cccs3)n2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#16;a:5]:[c:6].[C;D1;H3:7]-[NH;D2;+0:8]-[C;D1;H3:9]>>[C;D1;H3:7]-[N;H0;D3;+0:8](-[C;D1;H3:9])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#16;a:5]:[c:6] | null | [] | null | null | 3 | HOUR | 100 mg 5-{4-[3-(1,3-thiazol-2-yl)imidazo[1,2-a]pyridin-6-yl]-1-trityl-1H-3-pyrazolyl}-2-thiophene carboxylic acid (compound in Example 443), together with 66 μL triethylamine and 25 μL isobutyl chloroformate, was stirred for 30 minutes in 4 mL tetrahydrofuran under ice-cooling in a stream of nitrogen, and then 0.79 mL ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | c1ccsc1.c1c[nH]nc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccn2ccnc2c1.c1cscn1 | HO- | O | null | 3 | CNC.O=C(O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4nccs4)n3c2)s1>O>CN(C)C(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(-c4nccs4)n3c2)s1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5ebccfcfbcdc44148db4c42f0d9dc9ea | Cc1csc(N)n1.O=C(O)c1ccc(-c2cnc3ccc(-c4cnn(C(c5ccccc5)(c5ccccc5)c5ccccc5)c4)cn23)cc1F>>Cc1csc(NC(=O)c2ccc(-c3cnc4ccc(-c5cnn(C(c6ccccc6)(c6ccccc6)c6ccccc6)c5)cn34)cc2F)n1 | FC1=C(C(=O)O)C=CC(=C1)C1=CN=C2N1C=C(C=C2)C=2C=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2.NC=1SC=C(N1)C.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C.C(C)N(CC)CC>>CC=1N=C(SC1)NC(C1=C(C=C(C=C1)C1=CN=C2N1C=C(C=C2)C=2C=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)F)=O | [CH3:1][c:2]1[cH:3][s:4][c:5]([NH2:6])[n:49]1.O[C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12](-[c:13]2[cH:14][n:15][c:16]3[cH:17][cH:18][c:19](-[c:20]4[cH:21][n:22][n:23]([C:24]([c:25]5[cH:26][cH:27][cH:28][cH:29][cH:30]5)([c:31]5[cH:32][cH:33][cH:34][cH:35][cH:36]5)[c:37]5[cH:38][cH:39][cH:40][cH:41][cH:42]5)[cH:43]4)[cH:44]... | Cc1csc(N)n1.O=C(O)c1ccc(-c2cnc3ccc(-c4cnn(C(c5ccccc5)(c5ccccc5)c5ccccc5)c4)cn23)cc1F | Cc1csc(NC(=O)c2ccc(-c3cnc4ccc(-c5cnn(C(c6ccccc6)(c6ccccc6)c6ccccc6)c5)cn34)cc2F)n1 | null | null | ClCCl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1nccs1)c1ccc(-c2cnc3ccc(-c4cnn(C(c5ccccc5)(c5ccccc5)c5ccccc5)c4)cn23)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7]1:[#16;a:8]:[c:9]:[c:10]:[#7;a:11]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7]1:[#16;a:8]:[c:9]:[c:10]:[#7;a:11]:1)-[c:3](:[c:4]):[c:5] | 84.9 | [{"value": 84.9, "product": "CC=1N=C(SC1)NC(C1=C(C=C(C=C1)C1=CN=C2N1C=C(C=C2)C=2C=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 170 mg 2-fluoro-4-[6-(1-trityl-1H-4-pyrazolyl)imidazo-[1,2-a]pyridin-3-yl]benzoic acid (compound in Example 472) and 34.4 mg 2-amino-4-methyl-1,3-thiazole were allowed to react overnight with 146 mg benzotriazol-1-yloxy-tris-(dimethylamino)phosphonium hexafluorophosphate and 50 μL triethylamine in 6 mL dichloromethane.... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1cscn1.c1ccccc1.c1ccn2ccnc2c1.c1cn[nH]c1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | ClCCl | null | null | Cc1csc(N)n1.O=C(O)c1ccc(-c2cnc3ccc(-c4cnn(C(c5ccccc5)(c5ccccc5)c5ccccc5)c4)cn23)cc1F>ClCCl>Cc1csc(NC(=O)c2ccc(-c3cnc4ccc(-c5cnn(C(c6ccccc6)(c6ccccc6)c6ccccc6)c5)cn34)cc2F)n1 |
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