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-0387783899c642a8b7eb4ba379bcdf5d | ord-38c286fad8704ea9a9b77b748682d288 | O=C(CCl)CCl.O=C(N[C@@H](Cc1ccccc1)C(=O)O)OCc1ccccc1>>O=C(N[C@@H](Cc1ccccc1)[C@H](O)CCl)OCc1ccccc1 | ClCC(=O)CCl.C(C1=CC=CC=C1)OC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O.[BH4-].[Na+]>>C(C1=CC=CC=C1)OC(=O)N[C@H]([C@@H](CCl)O)CC1=CC=CC=C1 | O=C(CCl)[CH2:14][Cl:15].O=[C:12]([C@@H:4]([NH:3][C:2](=[O:1])[O:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1)[CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[OH:13]>>[O:1]=[C:2]([NH:3][C@@H:4]([CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[C@H:12]([OH:13])[CH2:14][Cl:15])[O:16][CH2:17][c:18]1[cH:19][cH:20][cH... | O=C(CCl)CCl.O=C(N[C@@H](Cc1ccccc1)C(=O)O)OCc1ccccc1 | O=C(N[C@@H](Cc1ccccc1)[C@H](O)CCl)OCc1ccccc1 | null | null | CO.O1CCCC1 | C-C Coupling | OtherReaction | be975736ea4dc284d6befa072d9777b891132a86c932e209ec3849b788893253 | 1c7c048f8a75ee2977c3642525e5bc0c5f72d9781847729e637668c64f734260 | O=C(NCCc1ccccc1)OCc1ccccc1 | Cl-C-C(=O)-[CH2;D2;+0:1]-[Cl;D1;H0:2].O=[C;H0;D3;+0:3](-[O;D1;H1:4])-[C:5](-[C:6])-[#7:7]-[C:8]=[O;D1;H0:9]>>[C:6]-[C:5](-[#7:7]-[C:8]=[O;D1;H0:9])-[C@H;D3;+0:3](-[O;D1;H1:4])-[CH2;D2;+0:1]-[Cl;D1;H0:2] | 48.4 | [{"value": 43.0, "product": "C(C1=CC=CC=C1)OC(=O)N[C@H]([C@@H](CCl)O)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.4, "product": "C(C1=CC=CC=C1)OC(=O)N[C@H]([C@@H](CCl)O)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of N-benzyloxycarbonyl-L-phenylalanine chloromethyl ketone (75 g, 0.2 mol) in a mixture of 800 mL of methanol and 800 mL of tetrahydrofuran was added sodium borohydride (13.17 g, 0.348 mol, 1.54 equiv.) over 100 min. The solution was stirred at room temperature for 2 hours and then concentrated in vacuo. ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Carboxylic acid.Ketone | Primary halide.Secondary alcohol | null | null | c1ccccc1.c1ccccc1 | HCl | CO.O1CCCC1 | null | 2 | O=C(CCl)CCl.O=C(N[C@@H](Cc1ccccc1)C(=O)O)OCc1ccccc1>CO.O1CCCC1>O=C(N[C@@H](Cc1ccccc1)[C@H](O)CCl)OCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ebe0473e580140e698140eacd97e4263 | O=C(N[C@@H](Cc1ccccc1)[C@H](O)CCl)OCc1ccccc1>>O=C(N[C@@H](Cc1ccccc1)[C@H]1CO1)OCc1ccccc1 | [OH-].[K+].C(C1=CC=CC=C1)OC(=O)N[C@H]([C@@H](CCl)O)CC1=CC=CC=C1>>C(C1=CC=CC=C1)OC(=O)N[C@H]([C@H]1CO1)CC1=CC=CC=C1 | Cl[CH2:13][C@H:12]([C@@H:4]([NH:3][C:2](=[O:1])[O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[OH:14]>>[O:1]=[C:2]([NH:3][C@@H:4]([CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[C@H:12]1[CH2:13][O:14]1)[O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1 | O=C(N[C@@H](Cc1ccccc1)[C@H](O)CCl)OCc1ccccc1 | O=C(N[C@@H](Cc1ccccc1)[C@H]1CO1)OCc1ccccc1 | null | null | ClCCl.C(C)O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis (intra to epoxy) | ebf120e9288f48b61f87dafb00b4bacd480e273fa54208a20ed1d8b8a8581b3e | 9d3e82e8fa4f4bc62c1019e0bd869bdb0cf4748977f3c0b945b8ffdfc70126be | O=C(N[C@@H](Cc1ccccc1)[C@H]1CO1)OCc1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2](-[C:3])-[OH;D1;+0:4]>>[C:3]-[C:2]1-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-1 | 77.3 | [{"value": 77.0, "product": "C(C1=CC=CC=C1)OC(=O)N[C@H]([C@H]1CO1)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.3, "product": "C(C1=CC=CC=C1)OC(=O)N[C@H]([C@H]1CO1)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A solution of potassium hydroxide (6.52 g, 0.116 mol, 1.2 equiv.) in 970 mL of absolute ethanol was treated with N-benzyloxycarbonyl-3(S)-amino-1-chloro-4-phenyl-2(S)-butanol (32.3 g, 0.097 mol). This solution was stirred at room temperature for 15 minutes and then concentrated in vacuo to give a white solid. The solid... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary alcohol | Ether | null | C1CO1 | c1ccccc1.C1CO1.c1ccccc1 | HCl | ClCCl.C(C)O | null | 0.25 | O=C(N[C@@H](Cc1ccccc1)[C@H](O)CCl)OCc1ccccc1>ClCCl.C(C)O>O=C(N[C@@H](Cc1ccccc1)[C@H]1CO1)OCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7c7f331849e741a384a746489950e6cd | O=S(=O)(Cl)Cl.c1ccc2c(c1)OCO2>>O=S(=O)(Cl)c1ccc2c(c1)OCO2 | O1COC2=C1C=CC=C2.S(=O)(=O)(Cl)Cl>>O1COC2=C1C=CC(=C2)S(=O)(=O)Cl | Cl[S:2](=[O:1])(=[O:3])[Cl:4].[cH:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[O:11][CH2:12][O:13]2>>[O:1]=[S:2](=[O:3])([Cl:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[O:11][CH2:12][O:13]2 | O=S(=O)(Cl)Cl.c1ccc2c(c1)OCO2 | O=S(=O)(Cl)c1ccc2c(c1)OCO2 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 3fc054f75f198b89d74fcdf05cd9e4e02a6088859e93e9ad89302c849c196bc8 | d32b60b8f9bfd187c6c9f1eef6a22a00f53525a7532b83aba763d5389c9e4280 | c1ccc2c(c1)OCO2 | Cl-[S;H0;D4;+0:1](-[Cl;D1;H0:2])(=[O;D1;H0:3])=[O;D1;H0:4].[#8:5]-[c:6]:[c:7]:[cH;D2;+0:8]:[c:9]:[c:10]>>[#8:5]-[c:6]:[c:7]:[c;H0;D3;+0:8](-[S;H0;D4;+0:1](-[Cl;D1;H0:2])(=[O;D1;H0:3])=[O;D1;H0:4]):[c:9]:[c:10] | 16.3 | [{"value": 16.3, "product": "O1COC2=C1C=CC(=C2)S(=O)(=O)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 15 | MINUTE | To a solution of 4.25 g of anhydrous N,N-dimethylformamide at 0° C. under nitrogen was added 7.84 g of sulfuryl chloride, whereupon a solid formed. After stirring for 15 minutes, 6.45 g of 1,3-benzodioxole was added, and the mixture heated at 100° C. for 2 hours. The reaction was cooled, poured into ice water, extracte... | 10.6084/m9.figshare.5104873.v1 | null | null | Sulfonyl halide | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | HCl | CN(C=O)C | 100 | 0.25 | O=S(=O)(Cl)Cl.c1ccc2c(c1)OCO2>CN(C=O)C>O=S(=O)(Cl)c1ccc2c(c1)OCO2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-372ffc0225a54493ac8ac28a26c543d8 | CC(C)CN(C[C@@H](O)[C@H](Cc1ccccc1)N(Cc1ccccc1)Cc1ccccc1)S(=O)(=O)c1ccc2c(c1)OCO2>>CC(C)CN(C[C@@H](O)[C@@H](N)Cc1ccccc1)S(=O)(=O)c1ccc2c(c1)OCO2 | O.O1COC2=C1C=CC(=C2)S(=O)(=O)N(CC(C)C)C[C@H]([C@H](CC2=CC=CC=C2)N(CC2=CC=CC=C2)CC2=CC=CC=C2)O.O.CS(=O)(=O)O>>O1COC2=C1C=CC(=C2)S(=O)(=O)N(CC(C)C)C[C@H]([C@H](CC2=CC=CC=C2)N)O | c1ccc(C[N:10](Cc2ccccc2)[C@H:9]([C@@H:7]([CH2:6][N:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[S:18](=[O:19])(=[O:20])[c:21]2[cH:22][cH:23][c:24]3[c:25]([cH:26]2)[O:27][CH2:28][O:29]3)[OH:8])[CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)cc1>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]([CH2:6][C@@H:7]([OH:8])[C@@H:9]([NH2:10])[CH2:1... | CC(C)CN(C[C@@H](O)[C@H](Cc1ccccc1)N(Cc1ccccc1)Cc1ccccc1)S(=O)(=O)c1ccc2c(c1)OCO2 | CC(C)CN(C[C@@H](O)[C@@H](N)Cc1ccccc1)S(=O)(=O)c1ccc2c(c1)OCO2 | null | [OH-].[OH-].[Pd+2] | C1CCOC1 | Deprotection | OtherReaction | 2d0141567e42eb1f1e525678ba93b1f94e67edd4ce8af946d59aa7922040fcc6 | 09463156f8971f4e8007d84d8ed410eed1d618bdb6ba7dd05b4970ff2019f62b | O=S(=O)(NCCCCc1ccccc1)c1ccc2c(c1)OCO2 | [C:1]-[C:2](-[C:3])-[N;H0;D3;+0:4](-C-c1:c:c:c:c:c:1)-C-c1:c:c:c:c:c:1>>[C:1]-[C:2](-[C:3])-[NH2;D1;+0:4] | null | [] | null | null | 16 | HOUR | Part B: To the THF solution of crude 1-[N-[(1,3-benzodioxol-5-yl)sulfonyl]-N-(2-methylpropyl)amino]-3(S)-[bis(phenylmethyl)amino]-4-phenyl-2(R)-butanol was added water (500 mL) followed by methane sulfonic acid (531 g, 5.5 moles). The solution was stirred to insure complete mixing and added to a 5 gallon autoclave. Pea... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Primary amine | c1ccccc1.c1ccccc1 | null | c1ccccc1.c1ccc2c(c1)OCO2 | Other | [OH-].[OH-].[Pd+2].C1CCOC1 | null | 16 | CC(C)CN(C[C@@H](O)[C@H](Cc1ccccc1)N(Cc1ccccc1)Cc1ccccc1)S(=O)(=O)c1ccc2c(c1)OCO2>[OH-].[OH-].[Pd+2].C1CCOC1>CC(C)CN(C[C@@H](O)[C@@H](N)Cc1ccccc1)S(=O)(=O)c1ccc2c(c1)OCO2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-65102f31262e4021b5784cb373f3c5c1 | O=S(=O)(O)c1ccc2ncsc2c1.O=S(Cl)Cl>>O=S(=O)(Cl)c1ccc2ncsc2c1 | S(=O)(Cl)Cl.S1C=NC2=C1C=C(C=C2)S(=O)(=O)O.CN(C=O)C>>ClS(=O)(=O)C1=CC2=C(N=CS2)C=C1 | O[S:2](=[O:1])(=[O:3])[c:5]1[cH:6][cH:7][c:8]2[n:9][cH:10][s:11][c:12]2[cH:13]1.O=S(Cl)[Cl:4]>>[O:1]=[S:2](=[O:3])([Cl:4])[c:5]1[cH:6][cH:7][c:8]2[n:9][cH:10][s:11][c:12]2[cH:13]1 | O=S(=O)(O)c1ccc2ncsc2c1.O=S(Cl)Cl | O=S(=O)(Cl)c1ccc2ncsc2c1 | null | null | ClC(C)Cl | Functional Group Interconversion | OtherReaction | 1d60417dbcce8291d459a7fb34824cf29ea6f69a30ac46aeb585ac8e7b69013e | 4a93b4a9749514113cd3dffa44b64f21b1f88d26b8739299bcad711fe7a13a1b | c1ccc2scnc2c1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[S;H0;D4;+0:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5](:[c:6]):[c:7]:[c:8]:[#16;a:9]>>[#16;a:9]:[c:8]:[c:7]:[c:5](-[S;H0;D4;+0:2](-[Cl;H0;D1;+0:1])(=[O;D1;H0:3])=[O;D1;H0:4]):[c:6] | null | [] | null | null | 1.5 | HOUR | Thionyl chloride (4 mL) was added to a suspension of the benzothiazole-6-sulfonic acid (0.60 g, 2.79 mmol) in dichloroethane (15 mL) and the reaction mixture was heated at reflux and dimethylformamide (5 mL) was added to the reaction mixture to yield a clear solution. After 1.5 hr. at reflux, the solvent was removed in... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonic acid | Sulfonyl halide | null | null | c1ccc2scnc2c1 | HCl | ClC(C)Cl | null | 1.5 | O=S(=O)(O)c1ccc2ncsc2c1.O=S(Cl)Cl>ClC(C)Cl>O=S(=O)(Cl)c1ccc2ncsc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ec436e219a7b4e779e97414f5d0737fc | COC(=O)Nc1nc2ccccc2[nH]1.O=S(=O)(O)Cl>>COC(=O)Nc1nc2ccc(S(=O)(=O)Cl)cc2[nH]1 | C(=O)(OC)NC=1NC2=C(N1)C=CC=C2.ClS(=O)(=O)O>>ClS(=O)(=O)C1=CC2=C(N=C(N2)NC(=O)OC)C=C1 | [CH3:1][O:2][C:3](=[O:4])[NH:5][c:6]1[n:7][c:8]2[cH:9][cH:10][cH:11][cH:16][c:17]2[nH:18]1.O=[S:12]([OH:13])(=[O:14])[Cl:15]>>[CH3:1][O:2][C:3](=[O:4])[NH:5][c:6]1[n:7][c:8]2[cH:9][cH:10][c:11]([S:12](=[O:13])(=[O:14])[Cl:15])[cH:16][c:17]2[nH:18]1 | COC(=O)Nc1nc2ccccc2[nH]1.O=S(=O)(O)Cl | COC(=O)Nc1nc2ccc(S(=O)(=O)Cl)cc2[nH]1 | null | null | null | Protection | Aromatic sulfonyl chlorination | 44a9386249fb09c227c1bade83a10e6d0e50059a06b5b8449d6ef54b8e158ff5 | c731d053565135be022f3edbe36cf28a9b4364ca579bdb183b2db9578bab4695 | c1ccc2[nH]cnc2c1 | O=[S;H0;D4;+0:1](-[Cl;D1;H0:2])(=[O;D1;H0:3])-[OH;D1;+0:4].[#7;a:5]1:[c:6]:[#7;a:7]:[c:8]2:[c:9]:[c:10]:[cH;D2;+0:11]:[c:12]:[c:13]:1:2>>[Cl;D1;H0:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;H0;D1;+0:4])-[c;H0;D3;+0:11]1:[c:10]:[c:9]:[c:8]2:[#7;a:7]:[c:6]:[#7;a:5]:[c:13]:2:[c:12]:1 | 78 | [{"value": 78.0, "product": "ClS(=O)(=O)C1=CC2=C(N=C(N2)NC(=O)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A solution of 2-carbomethoxyamino-benzimidazole (5.0 g, 0.026 mole) in chlorosulfonic acid (35.00 mL) was stirred at 0° C. for 30 minutes and at room temperature for 3 hours. The resulting dark colored reaction mixture was poured into an ice-water mixture (200 mL), and stirred at room temperature for 30 minutes. The re... | 10.6084/m9.figshare.5104873.v1 | null | null | Sulfonyl halide | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1 | HO- | null | null | 0.5 | COC(=O)Nc1nc2ccccc2[nH]1.O=S(=O)(O)Cl>>COC(=O)Nc1nc2ccc(S(=O)(=O)Cl)cc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8394ae5dca82428d92de21fda8556ee3 | Cn1c(N)cc(=O)[nH]c1=O.O=C1CCC(=O)N1Br>>Cn1c(N)c(Br)c(=O)[nH]c1=O | NC1=CC(NC(N1C)=O)=O.BrN1C(CCC1=O)=O>>NC1=C(C(NC(N1C)=O)=O)Br | [CH3:1][n:2]1[c:3]([NH2:4])[cH:5][c:7](=[O:8])[nH:9][c:10]1=[O:11].O=C1CCC(=O)N1[Br:6]>>[CH3:1][n:2]1[c:3]([NH2:4])[c:5]([Br:6])[c:7](=[O:8])[nH:9][c:10]1=[O:11] | Cn1c(N)cc(=O)[nH]c1=O.O=C1CCC(=O)N1Br | Cn1c(N)c(Br)c(=O)[nH]c1=O | null | null | CN(C)C=O | Functional Group Interconversion | Bromination | c1f267498588fdc78d70fa059a48254fc6fd3441a5bb656fda4935ce99f2babe | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=c1cc[nH]c(=O)[nH]1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[C;D1;H3:2]-[#7;a:3]1:[c:4]:[#7;a:5]:[c:6](=[O;D1;H0:7]):[cH;D2;+0:8]:[c:9]:1-[N;D1;H2:10]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:8]1:[c:9](-[N;D1;H2:10]):[#7;a:3](-[C;D1;H3:2]):[c:4]:[#7;a:5]:[c:6]:1=[O;D1;H0:7] | 83 | [{"value": 83.0, "product": "NC1=C(C(NC(N1C)=O)=O)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.8, "product": "NC1=C(C(NC(N1C)=O)=O)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A mixture of 6-amino-1-methyluracil (14.0 g, 100 mmol), N-bromosuccinimide (21.0 g, 118 mmol), and dry DMF (250 mL) was heated at 80° C. for 3 h. The reaction mixture was evaporated in vacuo and the residue was slurried with ice-cold 50% aqueous ethanol (150 mL) and filtered. The resulting off-white solid was washed wi... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1ccncn1.C1CCNC1 | c1cncnc1 | c1cncnc1 | HO- | CN(C)C=O | 80 | null | Cn1c(N)cc(=O)[nH]c1=O.O=C1CCC(=O)N1Br>CN(C)C=O>Cn1c(N)c(Br)c(=O)[nH]c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-46b5a06419784ab4aa0ab701d258a09a | CCC(N)C(=O)O.CCCC(=O)Cl>>CCCC(=O)NC(CC)C(=O)O | C(CCC)(=O)Cl.NC(C(=O)O)CC.C(C)N(CC)CC.[OH-].[Na+].C[Si](C)(C)Cl>>C(CCC)(=O)NC(C(=O)O)CC | [NH2:6][CH:7]([CH2:8][CH3:9])[C:10](=[O:11])[OH:12].Cl[C:4]([CH2:3][CH2:2][CH3:1])=[O:5]>>[CH3:1][CH2:2][CH2:3][C:4](=[O:5])[NH:6][CH:7]([CH2:8][CH3:9])[C:10](=[O:11])[OH:12] | CCC(N)C(=O)O.CCCC(=O)Cl | CCCC(=O)NC(CC)C(=O)O | null | null | ClCCl.O | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | null | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6](-[NH2;D1;+0:7])-[C:8](=[O;D1;H0:9])-[O;D1;H1:10]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6](-[C:5])-[C:8](=[O;D1;H0:9])-[O;D1;H1:10] | null | [] | 0 | CELSIUS | 1 | HOUR | 25.78 g of 2-aminobutyric acid (250 mmol) and 55.66 g (550 mmol) of triethylamine are dissolved in 250 ml of dichloromethane, and the solution is cooled to 0° C. 59.75 g (550 mmol) of trimethylsilyl chloride are added dropwise, and the solution is stirred at room temperature for 1 hour and at 40° C. for one hour. After... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | null | HCl | ClCCl.O | 0 | 1 | CCC(N)C(=O)O.CCCC(=O)Cl>ClCCl.O>CCCC(=O)NC(CC)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-70857ecec3d74fcaa02f50c4f69e4351 | CCCCCCC(=O)Cl.COC(=O)C(C)N>>CCCCCCC(=O)NC(C)C(=O)O | Cl.COC(C(N)C)=O.C(CCCCCC)(=O)Cl.O.[OH-].[Na+]>>C(CCCCCC)(=O)NC(C(=O)O)C | Cl[C:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:8].C[O:14][C:12]([CH:10]([NH2:9])[CH3:11])=[O:13]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7](=[O:8])[NH:9][CH:10]([CH3:11])[C:12](=[O:13])[OH:14] | CCCCCCC(=O)Cl.COC(=O)C(C)N | CCCCCCC(=O)NC(C)C(=O)O | null | null | C(Cl)Cl | Protection | OtherReaction | 38d0ee372433fbbe336780b47adc73f08791f5521c108d354eaa542b2747a5b4 | 88f5d7ff84f4ba180aefa4ce7745e5509dd1a3deb0add33de7fca1d17a38ff92 | null | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](-[C;D1;H3:5])-[NH2;D1;+0:6].Cl-[C;H0;D3;+0:7](=[O;D1;H0:8])-[C:9]-[C:10]>>[C:10]-[C:9]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[NH;D2;+0:6]-[C:4](-[C;D1;H3:5])-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | 2 | HOUR | 30 g (291 mmol) of D,L-alanine methyl ester hydrochloride and 64.77 g (640 mmol) of triethyl)amine are initially charged in 300 ml of dry methylene chloride at 0° C. 43.24 g (291 mmol) of heptanoyl chloride in 50 ml of methylene chloride are added dropwise. The mixture is allowed to warm to RT and stirred at this tempe... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ester.Primary amine | Carboxylic acid.Secondary amide | null | null | null | HCl | C(Cl)Cl | null | 2 | CCCCCCC(=O)Cl.COC(=O)C(C)N>C(Cl)Cl>CCCCCCC(=O)NC(C)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6ee13a8e601e4d21be3558a4c3597e8a | CCCCCCCCCC(=O)Cl.COC(=O)C(C)N>>CCCCCCCCCC(=O)NC(C)C(=O)O | Cl.COC(C(N)C)=O.C(CCCCCCCCC)(=O)Cl>>C(CCCCCCCCC)(=O)NC(C(=O)O)C | Cl[C:10]([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:11].C[O:17][C:15]([CH:13]([NH2:12])[CH3:14])=[O:16]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10](=[O:11])[NH:12][CH:13]([CH3:14])[C:15](=[O:16])[OH:17] | CCCCCCCCCC(=O)Cl.COC(=O)C(C)N | CCCCCCCCCC(=O)NC(C)C(=O)O | null | null | null | Protection | OtherReaction | 38d0ee372433fbbe336780b47adc73f08791f5521c108d354eaa542b2747a5b4 | 88f5d7ff84f4ba180aefa4ce7745e5509dd1a3deb0add33de7fca1d17a38ff92 | null | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](-[C;D1;H3:5])-[NH2;D1;+0:6].Cl-[C;H0;D3;+0:7](=[O;D1;H0:8])-[C:9]-[C:10]>>[C:10]-[C:9]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[NH;D2;+0:6]-[C:4](-[C;D1;H3:5])-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | null | null | The preparation is carried out analogously to the procedure of example 4A using 19.0 g (184 mmol) of D,L-alanine methyl ester hydrochloride and 35.14 g (184 mmol) of decanoyl chloride.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ester.Primary amine | Carboxylic acid.Secondary amide | null | null | null | HCl | null | null | null | CCCCCCCCCC(=O)Cl.COC(=O)C(C)N>>CCCCCCCCCC(=O)NC(C)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e518c5dd9fa5486fbc329b8f5d12c6b8 | CC(N)C(=O)O.CCCCCCC(CC)C(=O)Cl>>CCCCCCC(CC)C(=O)NC(C)C(=O)O | NC(C)C(=O)O.C(C)N(CC)CC.C(C)C(C(=O)Cl)CCCCCC.C[Si](C)(C)Cl>>CCC(C(=O)NC(C(=O)O)C)CCCCCC | [NH2:12][CH:13]([CH3:14])[C:15](=[O:16])[OH:17].Cl[C:10]([CH:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[CH2:8][CH3:9])=[O:11]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]([CH2:8][CH3:9])[C:10](=[O:11])[NH:12][CH:13]([CH3:14])[C:15](=[O:16])[OH:17] | CC(N)C(=O)O.CCCCCCC(CC)C(=O)Cl | CCCCCCC(CC)C(=O)NC(C)C(=O)O | null | null | ClCCl.O | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | null | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[C;D1;H3:6]-[C:7](-[NH2;D1;+0:8])-[C:9](=[O;D1;H0:10])-[O;D1;H1:11]>>[C:4]-[C:3](-[C:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C:7](-[C;D1;H3:6])-[C:9](=[O;D1;H0:10])-[O;D1;H1:11] | null | [] | null | null | 1 | HOUR | 18.6 g (0.211 mol) of D,L-alanine and 46.6 g (0.41 mol) of triethylamine are initially charged in 300 ml of dichloromethane. At 0° C. 50.09 g (0.461 mol) of trimethylsilyl chloride are added dropwise, and the mixture is stirred at room temperature for 1 h and then at 40° C. for 1 h. The solution is cooled to −10° C., a... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | null | HCl | ClCCl.O | null | 1 | CC(N)C(=O)O.CCCCCCC(CC)C(=O)Cl>ClCCl.O>CCCCCCC(CC)C(=O)NC(C)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d94f79942acd4abda53fdab727364607 | CC(N)C(=O)O.O=C(Cl)C1CCCC1>>CC(NC(=O)C1CCCC1)C(=O)O | C1(CCCC1)C(=O)Cl.NC(C)C(=O)O.C(C)N(CC)CC.C[Si](C)(C)Cl>>C1(CCCC1)C(=O)NC(C(=O)O)C | [CH3:1][CH:2]([NH2:3])[C:11](=[O:12])[OH:13].Cl[C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10]1>>[CH3:1][CH:2]([NH:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10]1)[C:11](=[O:12])[OH:13] | CC(N)C(=O)O.O=C(Cl)C1CCCC1 | CC(NC(=O)C1CCCC1)C(=O)O | null | null | ClCCl.O | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | C1CCCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[C;D1;H3:6]-[C:7](-[NH2;D1;+0:8])-[C:9](=[O;D1;H0:10])-[O;D1;H1:11]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C:7](-[C;D1;H3:6])-[C:9](=[O;D1;H0:10])-[O;D1;H1:11])-[C:5] | null | [] | null | null | 1 | HOUR | 16.8 g (0.189 mol) of D,L-alanine and 41.98 g (0.415 mol) of triethylamine are initially charged in 200 ml of dichloromethane. At 0° C. 45.07 g (0.415 mol) of trimethylsilyl chloride are added dropwise, and the mixture is stirred at room temperature for 1 h and then at 40° C. for 1 h. The solution is cooled to −10° C.,... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CCCC1 | HCl | ClCCl.O | null | 1 | CC(N)C(=O)O.O=C(Cl)C1CCCC1>ClCCl.O>CC(NC(=O)C1CCCC1)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-97843fa2913f49ca9a50bf40eb014f8f | COC(=O)C(C)N.O=C(Cl)C1CCCCCC1>>CC(NC(=O)C1CCCCCC1)C(=O)O | Cl.COC(C(N)C)=O.C1(CCCCCC1)C(=O)Cl>>C1(CCCCCC1)C(=O)NC(C(=O)O)C | C[O:15][C:13]([CH:2]([CH3:1])[NH2:3])=[O:14].Cl[C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1>>[CH3:1][CH:2]([NH:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1)[C:13](=[O:14])[OH:15] | COC(=O)C(C)N.O=C(Cl)C1CCCCCC1 | CC(NC(=O)C1CCCCCC1)C(=O)O | null | null | null | Acylation | OtherReaction | ef24946e812c58ec5646342efa5dafd5ed10bf586e98ff0052340ef0daf33e7e | 5dbbcac586755560aba4a2c29e7a14cbdd68815807327d0e3fd0dd155b11b926 | C1CCCCCC1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](-[C;D1;H3:5])-[NH2;D1;+0:6].Cl-[C;H0;D3;+0:7](=[O;D1;H0:8])-[C:9](-[C:10])-[C:11]>>[C:10]-[C:9](-[C;H0;D3;+0:7](=[O;D1;H0:8])-[NH;D2;+0:6]-[C:4](-[C;D1;H3:5])-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1])-[C:11] | null | [] | null | null | null | null | The preparation is carried out analogously to the procedure of example 4A using 20 g (143 mmol) of D,L-alanine methyl ester hydrochloride and 23.02 g (143 mmmol) of cycloheptanoyl chloride.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ester.Primary amine | Carboxylic acid.Secondary amide | null | null | C1CCCCCC1 | HCl | null | null | null | COC(=O)C(C)N.O=C(Cl)C1CCCCCC1>>CC(NC(=O)C1CCCCCC1)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b6831fca491149af9b43e92a72273938 | CCBr.N#Cc1ccccc1O>>CCOc1ccccc1C#N | OC1=C(C#N)C=CC=C1.C([O-])([O-])=O.[K+].[K+].C(C)Br>>C(C)OC1=C(C#N)C=CC=C1 | Br[CH2:2][CH3:1].[OH:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[C:10]#[N:11]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[C:10]#[N:11] | CCBr.N#Cc1ccccc1O | CCOc1ccccc1C#N | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C;D1;H3:2].[OH;D1;+0:3]-[c:4](:[c:5]):[c:6]>>[C;D1;H3:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:3]-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | 25 g (210 mmol) of 2-hydroxybenzonitrile, 87 g of potassium carbonate and 34.3 g (314.8 mmol) of ethyl bromide are refluxed in 500 ml of acetone overnight. The solid is filtered off, the solvent is removed under reduced pressure and the residue is distilled under reduced pressure. This gives 30.0 g (97%) of a colorless... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | CC(=O)C | null | null | CCBr.N#Cc1ccccc1O>CC(=O)C>CCOc1ccccc1C#N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b97f90e65b064970a2b84bf42bde3570 | CCOc1ccc(OCc2ccccc2)cc1C#N.[Cl-].[NH4+]>>CCOc1ccc(OCc2ccccc2)cc1C(=N)N.Cl | [Cl-].[NH4+].C(C1=CC=CC=C1)OC=1C=CC(=C(C#N)C1)OCC.C[Al](C)C.CCCCCC>>Cl.C(C1=CC=CC=C1)OC=1C=C(C(=N)N)C(=CC1)OCC | [CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16][c:17]1[C:18]#[N:19].[Cl-:21].[NH4+:20]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16][c:17]1[C:18](=[NH:19])[NH2:20].[ClH:21] | CCOc1ccc(OCc2ccccc2)cc1C#N.[Cl-].[NH4+] | CCOc1ccc(OCc2ccccc2)cc1C(=N)N.Cl | null | null | ClCCl.C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | 3b047a13c16a607c445b1c419e256808e8c9a0097d8fb9efd4e7970deb782b70 | 2882e57127fc469aa16ca9a2fd53388b6d97c74c76c010e6eb01be5726f46aa5 | c1ccc(COc2ccccc2)cc1 | [Cl-;H0;D0:1].[N;H0;D1;+0:2]#[C;H0;D2;+0:3]-[c:4](:[c:5]):[c:6].[NH4+;D0:7]>>[ClH;D0;+0:1].[NH2;D1;+0:7]-[C;H0;D3;+0:3](=[NH;D1;+0:2])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | 46.46 g of ammonium chloride (868.5 mol) are suspended in 650 ml of toluene, and the mixture is cooled to 0–5° C. Trimethylaluminum is added dropwise as a 2M solution in hexane (445 ml, 888.3 mmol), and the mixture is then stirred at room temperature until the evolution of gas has ceased. 5-Benzyloxy-2-ethoxybenzonitri... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccccc1.c1ccccc1 | null | ClCCl.C1(=CC=CC=C1)C | null | null | CCOc1ccc(OCc2ccccc2)cc1C#N.[Cl-].[NH4+]>ClCCl.C1(=CC=CC=C1)C>CCOc1ccc(OCc2ccccc2)cc1C(=N)N.Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-508ee62d64134b1dba54107904fed0f8 | CCOc1ccc(OCc2ccccc2)cc1C#N>>CCOc1ccc(O)cc1C#N | C(C1=CC=CC=C1)OC=1C=CC(=C(C#N)C1)OCC>>C(C)OC1=C(C#N)C=C(C=C1)O | c1ccc(C[O:8][c:7]2[cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[c:10]([C:11]#[N:12])[cH:9]2)cc1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([OH:8])[cH:9][c:10]1[C:11]#[N:12] | CCOc1ccc(OCc2ccccc2)cc1C#N | CCOc1ccc(O)cc1C#N | null | [Pd] | CO | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccccc1 | [c:1]:[c:2](-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[OH;D1;+0:3]-[c:2](:[c:1]):[c:4] | null | [] | null | null | 4 | HOUR | 40.02 g of 5-benzyloxy-2-ethoxybenizonitrile (158 mmol) (example 32A) and 5% Pd/C (4.0 g) are initially charged in 1 l of methanol. The mixture is then hydrogenated under an atmosphere of hydrogen (1 atm) for about 4 h. The mixture is filtered through kieselguhr and evaporated and the crystalline residue is dried under... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccccc1 | Other | [Pd].CO | null | 4 | CCOc1ccc(OCc2ccccc2)cc1C#N>[Pd].CO>CCOc1ccc(O)cc1C#N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a4f97ceaf626467dba55ac336b431903 | C=CCBr.CCOc1ccc(O)cc1C#N>>C=CCOc1ccc(OCC)c(C#N)c1 | C(C)OC1=C(C#N)C=C(C=C1)O.C([O-])([O-])=O.[K+].[K+].C(C=C)Br>>C(C=C)OC=1C=CC(=C(C#N)C1)OCC | Br[CH2:3][CH:2]=[CH2:1].[OH:4][c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH3:11])[c:12]([C:13]#[N:14])[cH:15]1>>[CH2:1]=[CH:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH3:11])[c:12]([C:13]#[N:14])[cH:15]1 | C=CCBr.CCOc1ccc(O)cc1C#N | C=CCOc1ccc(OCC)c(C#N)c1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H2:3]=[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | 25 g of 2-ethoxy-5-hydroxybenzonitrile (153.2 mmol) (example 36A) and potassium carbonate (63.52 g, 459.6 mmol) are initially charged in 750 ml of acetone, 19.9 ml of allyl bromide (229.8 mmol) are added, and the mixture is stirred under reflux overnight. The mixture is filtered off and concentrated giving a mobile ora... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | CC(=O)C | null | null | C=CCBr.CCOc1ccc(O)cc1C#N>CC(=O)C>C=CCOc1ccc(OCC)c(C#N)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ebb0166aad5942ed9b0e31b364855402 | CCOc1ccccc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1.O=[N+]([O-])O>>CCOc1ccc([N+](=O)[O-])cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 | C([O-])(O)=O.[Na+].ClCCl.C(C)OC1=C(C=CC=C1)C1=NN2C(C(N1)=O)=C(N=C2C2CCCC2)C.[N+](=O)(O)[O-]>>C(C)OC1=C(C=C(C=C1)[N+](=O)[O-])C1=NN2C(C(N1)=O)=C(N=C2C2CCCC2)C | [CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][cH:7][cH:11][c:12]1-[c:13]1[n:14][n:15]2[c:16]([CH:17]3[CH2:18][CH2:19][CH2:20][CH2:21]3)[n:22][c:23]([CH3:24])[c:25]2[c:26](=[O:27])[nH:28]1.O[N+:8](=[O:9])[O-:10]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][c:12]1-[c:13]1[n:14][n:15]2[c:16]([CH:17]3[... | CCOc1ccccc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1.O=[N+]([O-])O | CCOc1ccc([N+](=O)[O-])cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 | null | null | C(=O)(C(F)(F)F)O.FC(C(=O)O)(F)F | Functional Group Addition | Aromatic nitration with HNO3 | 53848b8b2bb4e867226e49db2e60519b24be9379900e3ad7c56af54fe8fde7a5 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | O=c1[nH]c(-c2ccccc2)nn2c(C3CCCC3)ncc12 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]>>[O;-;D1;H0:2]-[N+;H0;D3:1](=[O;D1;H0:3])-[c;H0;D3;+0:6](:[c:5]:[c:4]):[c:7]:[c:8] | null | [] | 0 | CELSIUS | 20 | HOUR | Using an ice-acetone bath, 48.6 ml of trifluoroacetic acid (TFA and 12.1 ml of 70% strength nitric acid are cooled to −10° C., 3.0 g (8.86 mmol) of the compound from example 25A, dissolved in 7 ml of TFA are added dropwise, and the mixture is stirred at 0° C. for 20 hours. The reaction solution is stirred into 400 ml o... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CCCC1.c1ncc2cncn2n1 | HO- | C(=O)(C(F)(F)F)O.FC(C(=O)O)(F)F | 0 | 20 | CCOc1ccccc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1.O=[N+]([O-])O>C(=O)(C(F)(F)F)O.FC(C(=O)O)(F)F>CCOc1ccc([N+](=O)[O-])cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d357c1218dbf48bba5a042e2f55bdc08 | CCOc1ccc([N+](=O)[O-])cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1>>CCOc1ccc(N)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 | O1CCCC1.C(C)OC1=C(C=C(C=C1)[N+](=O)[O-])C1=NN2C(C(N1)=O)=C(N=C2C2CCCC2)C>>NC=1C=CC(=C(C1)C1=NN2C(C(N1)=O)=C(N=C2C2CCCC2)C)OCC | O=[N+:8]([O-])[c:7]1[cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[c:10](-[c:11]2[n:12][n:13]3[c:14]([CH:15]4[CH2:16][CH2:17][CH2:18][CH2:19]4)[n:20][c:21]([CH3:22])[c:23]3[c:24](=[O:25])[nH:26]2)[cH:9]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([NH2:8])[cH:9][c:10]1-[c:11]1[n:12][n:13]2[c:14]([CH:15]3[CH2:16][CH2:17][CH2:18... | CCOc1ccc([N+](=O)[O-])cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 | CCOc1ccc(N)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=c1[nH]c(-c2ccccc2)nn2c(C3CCCC3)ncc12 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | In 86 ml of ethanol and 86 ml of tetrahydrofuran 2.56 g (6.68 mmol) of the compound from example 41A are stirred in the presence of 288 mg of Pd/C (10%) under an H2 atmosphere for 20 hours. The reaction solution is filtered with suction through 30 ml of silica gel, the filter cake is washed with ethanol/tetrahydrofuran... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.C1CCCC1.c1ncc2cncn2n1 | Other | [Pd].C(C)O | null | null | CCOc1ccc([N+](=O)[O-])cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1>[Pd].C(C)O>CCOc1ccc(N)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3609d8295c624050ac05778cb451d5f2 | CCCOc1ccccc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1.O=[N+]([O-])O>>CCCOc1ccc([N+](=O)[O-])cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 | C(CC)OC1=C(C=CC=C1)C1=NN2C(C(N1)=O)=C(N=C2C2CCCC2)C.[N+](=O)(O)[O-]>>[N+](=O)([O-])C=1C=CC(=C(C1)C1=NN2C(C(N1)=O)=C(N=C2C2CCCC2)C)OCCC | [CH3:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][cH:7][cH:8][cH:12][c:13]1-[c:14]1[n:15][n:16]2[c:17]([CH:18]3[CH2:19][CH2:20][CH2:21][CH2:22]3)[n:23][c:24]([CH3:25])[c:26]2[c:27](=[O:28])[nH:29]1.O[N+:9](=[O:10])[O-:11]>>[CH3:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][c:13]1-[c:14]1[n:15][n:16]2... | CCCOc1ccccc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1.O=[N+]([O-])O | CCCOc1ccc([N+](=O)[O-])cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 | null | null | FC(C(=O)O)(F)F | Functional Group Addition | Aromatic nitration with HNO3 | 53848b8b2bb4e867226e49db2e60519b24be9379900e3ad7c56af54fe8fde7a5 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | O=c1[nH]c(-c2ccccc2)nn2c(C3CCCC3)ncc12 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]>>[O;-;D1;H0:2]-[N+;H0;D3:1](=[O;D1;H0:3])-[c;H0;D3;+0:6](:[c:5]:[c:4]):[c:7]:[c:8] | null | [] | null | null | null | null | Analogously to the procedure of example 41A, 10.0 g (28.4 mmol) of the compound from example 26A are nitrated in 160 ml of trifluoroacetic acid and 40 ml of 70% strength nitric acid. The product is purified by silica gel chromatography using toluene and ethyl acetate in a gradient system.
Conditions: See reaction.notes... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CCCC1.c1ncc2cncn2n1 | HO- | FC(C(=O)O)(F)F | null | null | CCCOc1ccccc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1.O=[N+]([O-])O>FC(C(=O)O)(F)F>CCCOc1ccc([N+](=O)[O-])cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4282992d9f884e20a0f83bdc2c8a2c5d | CCCOc1ccc([N+](=O)[O-])cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1>>CCCOc1ccc(N)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 | [N+](=O)([O-])C=1C=CC(=C(C1)C1=NN2C(C(N1)=O)=C(N=C2C2CCCC2)C)OCCC>>NC=1C=CC(=C(C1)C1=NN2C(C(N1)=O)=C(N=C2C2CCCC2)C)OCCC | O=[N+:9]([O-])[c:8]1[cH:7][cH:6][c:5]([O:4][CH2:3][CH2:2][CH3:1])[c:11](-[c:12]2[n:13][n:14]3[c:15]([CH:16]4[CH2:17][CH2:18][CH2:19][CH2:20]4)[n:21][c:22]([CH3:23])[c:24]3[c:25](=[O:26])[nH:27]2)[cH:10]1>>[CH3:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([NH2:9])[cH:10][c:11]1-[c:12]1[n:13][n:14]2[c:15]([CH:16]3[CH2:17... | CCCOc1ccc([N+](=O)[O-])cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 | CCCOc1ccc(N)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 | null | [Pd] | O1CCCC1.C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=c1[nH]c(-c2ccccc2)nn2c(C3CCCC3)ncc12 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | Analogously to the procedure of example 42A, 5.13 g (12.96 mmol) of the compound from example 43A are hydrogenated in tetrahydrofuran/ethanol (1:1) using 1.11 g of 10% Pd/C. The product is purified by silica gel chromalography using toluene and ethyl acetate as solvent gradient.
Conditions: See reaction.notes.procedure... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.C1CCCC1.c1ncc2cncn2n1 | Other | [Pd].O1CCCC1.C(C)O | null | null | CCCOc1ccc([N+](=O)[O-])cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1>[Pd].O1CCCC1.C(C)O>CCCOc1ccc(N)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-beb9284104874dccbc49023925c5f0f0 | CCCCCC(CC)Cc1nc(C)c2c(=O)[nH]c(-c3cc([N+](=O)[O-])ccc3OCC)nn12>>CCCCCC(CC)Cc1nc(C)c2c(=O)[nH]c(-c3cc(N)ccc3OCC)nn12 | C(C)OC1=C(C=C(C=C1)[N+](=O)[O-])C1=NN2C(C(N1)=O)=C(N=C2CC(CCCCC)CC)C.C1CCCCC1.C(C)(=O)OCC>>NC=1C=CC(=C(C1)C1=NN2C(C(N1)=O)=C(N=C2CC(CCCCC)CC)C)OCC | O=[N+:22]([O-])[c:21]1[cH:20][c:19](-[c:18]2[nH:17][c:15](=[O:16])[c:14]3[c:12]([CH3:13])[n:11][c:10]([CH2:9][CH:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[CH2:7][CH3:8])[n:30]3[n:29]2)[c:25]([O:26][CH2:27][CH3:28])[cH:24][cH:23]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([CH2:7][CH3:8])[CH2:9][c:10]1[n:11][c:12]([CH3:13... | CCCCCC(CC)Cc1nc(C)c2c(=O)[nH]c(-c3cc([N+](=O)[O-])ccc3OCC)nn12 | CCCCCC(CC)Cc1nc(C)c2c(=O)[nH]c(-c3cc(N)ccc3OCC)nn12 | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=c1[nH]c(-c2ccccc2)nn2cncc12 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | Analogously to the procedure of example 42A, 1.95 g (4.42 mmol) of the compound from example 49A are hydrogenated in 120 g of ethanol using 200 mg of 10% Pd/C. Chromatography on 400 ml of silica gel using cyclohexane and ethyl acetate in a gradient system from 90:10 to 40:60 gives 1.26 g (69.4% of theory).
Conditions: ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ncc2cncn2n1.c1ccccc1 | Other | [Pd].C(C)O | null | null | CCCCCC(CC)Cc1nc(C)c2c(=O)[nH]c(-c3cc([N+](=O)[O-])ccc3OCC)nn12>[Pd].C(C)O>CCCCCC(CC)Cc1nc(C)c2c(=O)[nH]c(-c3cc(N)ccc3OCC)nn12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1a9df976ff5240b3a21e1366d2833d10 | CCCc1nc(CC)c2c(=O)[nH]c(-c3ccccc3OCC)nn12.O=C(Br)CBr>>CCCc1nc(CC)c2c(=O)[nH]c(-c3cc(C(=O)CBr)ccc3OCC)nn12 | BrCC(=O)Br.C(C)OC1=C(C=CC=C1)C1=NN2C(C(N1)=O)=C(N=C2CCC)CC.[Al+3].[Cl-].[Cl-].[Cl-]>>BrCC(=O)C=1C=CC(=C(C1)C1=NN2C(C(N1)=O)=C(N=C2CCC)CC)OCC | [CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]([CH2:7][CH3:8])[c:9]2[c:10](=[O:11])[nH:12][c:13](-[c:14]3[cH:15][cH:16][cH:21][cH:22][c:23]3[O:24][CH2:25][CH3:26])[n:27][n:28]12.Br[C:17](=[O:18])[CH2:19][Br:20]>>[CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]([CH2:7][CH3:8])[c:9]2[c:10](=[O:11])[nH:12][c:13](-[c:14]3[cH:15][c:16]([C:17](... | CCCc1nc(CC)c2c(=O)[nH]c(-c3ccccc3OCC)nn12.O=C(Br)CBr | CCCc1nc(CC)c2c(=O)[nH]c(-c3cc(C(=O)CBr)ccc3OCC)nn12 | null | null | C(Cl)Cl | C-C Coupling | Friedel-Crafts acylation | 55541449ad4f182ef3dc0497085b282b1dcb76e0fb5ed140dc4eab4973eacb28 | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | O=c1[nH]c(-c2ccccc2)nn2cncc12 | Br-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Br;D1;H0:4].[c:5]:[c:6]:[cH;D2;+0:7]:[c:8]:[c:9]>>[Br;D1;H0:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:7](:[c:6]:[c:5]):[c:8]:[c:9] | null | [] | null | null | null | null | A solution, cooled to 0° C., of 1 g (3.1 mmol) of the compound from example 17A in 80 ml of CH2Cl2 was admixed dropwise with 1.2 g (6.1 mmol) of bromoacetyl bromide and a little at a time with 1.2 g (9.1 mmol) of AlCl3. The reaction mixture was warmed to room temperature (30 min.) and then heated at reflux for 2 h and ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccccc1 | c1ccccc1 | c1ncc2cncn2n1.c1ccccc1 | HBr | C(Cl)Cl | null | null | CCCc1nc(CC)c2c(=O)[nH]c(-c3ccccc3OCC)nn12.O=C(Br)CBr>C(Cl)Cl>CCCc1nc(CC)c2c(=O)[nH]c(-c3cc(C(=O)CBr)ccc3OCC)nn12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e437a9002e724c88bacab9094317fea1 | CCOc1ccccc1-c1nn2c(C3CCCCCC3)nc(C)c2c(=O)[nH]1.O=C(Br)CBr>>CCOc1ccc(C(=O)CBr)cc1-c1nn2c(C3CCCCCC3)nc(C)c2c(=O)[nH]1 | C(C)OC1=C(C=CC=C1)C1=NN2C(C(N1)=O)=C(N=C2C2CCCCCC2)C.BrCC(=O)Br.[Cl-].[Cl-].[Cl-].[Al+3]>>BrCC(=O)C=1C=CC(=C(C1)C1=NN2C(C(N1)=O)=C(N=C2C2CCCCCC2)C)OCC | [CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][cH:7][cH:12][c:13]1-[c:14]1[n:15][n:16]2[c:17]([CH:18]3[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]3)[n:25][c:26]([CH3:27])[c:28]2[c:29](=[O:30])[nH:31]1.Br[C:8](=[O:9])[CH2:10][Br:11]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[CH2:10][Br:11])[cH:12][c:13]1-[c:14... | CCOc1ccccc1-c1nn2c(C3CCCCCC3)nc(C)c2c(=O)[nH]1.O=C(Br)CBr | CCOc1ccc(C(=O)CBr)cc1-c1nn2c(C3CCCCCC3)nc(C)c2c(=O)[nH]1 | null | null | CCOCC | C-C Coupling | Friedel-Crafts acylation | 55541449ad4f182ef3dc0497085b282b1dcb76e0fb5ed140dc4eab4973eacb28 | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | O=c1[nH]c(-c2ccccc2)nn2c(C3CCCCCC3)ncc12 | Br-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Br;D1;H0:4].[c:5]:[c:6]:[cH;D2;+0:7]:[c:8]:[c:9]>>[Br;D1;H0:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:7](:[c:6]:[c:5]):[c:8]:[c:9] | 66.5 | [{"value": 66.3, "product": "BrCC(=O)C=1C=CC(=C(C1)C1=NN2C(C(N1)=O)=C(N=C2C2CCCCCC2)C)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.5, "product": "BrCC(=O)C=1C=CC(=C(C1)C1=NN2C(C(N1)=O)=C(N=C2C2CCCCCC2)C)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Analogously to example 57A, 1.36 g (3.7 mmol) of the compound from example 28A were reacted with 1.5 g (7.4 mmol) of bromoacetyl bromide and 1.48 g (1.1 mmol) of aluminum trichloride. Trituration with ether gave 1.2 g (66.3%) of the desired product.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CCCCCC1.c1ncc2cncn2n1 | HBr | CCOCC | null | null | CCOc1ccccc1-c1nn2c(C3CCCCCC3)nc(C)c2c(=O)[nH]1.O=C(Br)CBr>CCOCC>CCOc1ccc(C(=O)CBr)cc1-c1nn2c(C3CCCCCC3)nc(C)c2c(=O)[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-19738cf49f484ac1b29bcf3080bba171 | CCCCOc1ccc(S(=O)(=O)Cl)cc1.CCOc1ccc(N)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1>>CCCCOc1ccc(S(=O)(=O)Nc2ccc(OCC)c(-c3nn4c(C5CCCC5)nc(C)c4c(=O)[nH]3)c2)cc1 | NC=1C=CC(=C(C1)C1=NN2C(C(N1)=O)=C(N=C2C2CCCC2)C)OCC.C(CCC)OC1=CC=C(C=C1)S(=O)(=O)Cl.N1=CC=CC=C1>>C(CCC)OC1=CC=C(C=C1)S(=O)(=O)NC=1C=CC(=C(C1)C1=NN2C(C(N1)=O)=C(N=C2C2CCCC2)C)OCC | Cl[S:10]([c:9]1[cH:8][cH:7][c:6]([O:5][CH2:4][CH2:3][CH2:2][CH3:1])[cH:40][cH:39]1)(=[O:11])=[O:12].[NH2:13][c:14]1[cH:15][cH:16][c:17]([O:18][CH2:19][CH3:20])[c:21](-[c:22]2[n:23][n:24]3[c:25]([CH:26]4[CH2:27][CH2:28][CH2:29][CH2:30]4)[n:31][c:32]([CH3:33])[c:34]3[c:35](=[O:36])[nH:37]2)[cH:38]1>>[CH3:1][CH2:2][CH2:3]... | CCCCOc1ccc(S(=O)(=O)Cl)cc1.CCOc1ccc(N)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 | CCCCOc1ccc(S(=O)(=O)Nc2ccc(OCC)c(-c3nn4c(C5CCCC5)nc(C)c4c(=O)[nH]3)c2)cc1 | null | null | O1CCCC1 | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=c1[nH]c(-c2cccc(NS(=O)(=O)c3ccccc3)c2)nn2c(C3CCCC3)ncc12 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | 150 mg (0.424 mmol) of the compound from example 42A are reacted with 186 mg (0.747 mmol) of 4-(n-butoxy)-benzenesulfonyl chloride and 0.34 g (4.30 mmol) of pyridine in 6 ml of tetrahydrofuran.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccccc1.C1CCCC1.c1ncc2cncn2n1 | HCl | O1CCCC1 | null | null | CCCCOc1ccc(S(=O)(=O)Cl)cc1.CCOc1ccc(N)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1>O1CCCC1>CCCCOc1ccc(S(=O)(=O)Nc2ccc(OCC)c(-c3nn4c(C5CCCC5)nc(C)c4c(=O)[nH]3)c2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7afd0643970c4a04875dffee36f30101 | CCOc1ccc(N)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1.Cn1cnc(S(=O)(=O)Cl)c1>>CCOc1ccc(NS(=O)(=O)c2cn(C)cn2)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 | NC=1C=CC(=C(C1)C1=NN2C(C(N1)=O)=C(N=C2C2CCCC2)C)OCC.CN1C=NC(=C1)S(=O)(=O)Cl.N1=CC=CC=C1>>C(C)OC1=C(C=C(C=C1)NS(=O)(=O)C=1N=CN(C1)C)C1=NN2C(C(N1)=O)=C(N=C2C2CCCC2)C | [CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([NH2:8])[cH:18][c:19]1-[c:20]1[n:21][n:22]2[c:23]([CH:24]3[CH2:25][CH2:26][CH2:27][CH2:28]3)[n:29][c:30]([CH3:31])[c:32]2[c:33](=[O:34])[nH:35]1.Cl[S:9](=[O:10])(=[O:11])[c:12]1[cH:13][n:14]([CH3:15])[cH:16][n:17]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([NH:8][S:9](=[O:10... | CCOc1ccc(N)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1.Cn1cnc(S(=O)(=O)Cl)c1 | CCOc1ccc(NS(=O)(=O)c2cn(C)cn2)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 | null | null | O1CCCC1 | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=c1[nH]c(-c2cccc(NS(=O)(=O)c3c[nH]cn3)c2)nn2c(C3CCCC3)ncc12 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4]1:[#7;a:5]:[c:6]:[#7;a:7](-[C;D1;H3:8]):[c:9]:1.[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C;D1;H3:8]-[#7;a:7]1:[c:9]:[c:4](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[#7;a:5]:[c:6]:1 | null | [] | null | null | null | null | 150 mg (0.424 mmol) of the compound from example 42A are reacted with 307 mg (1.70 mmol) of 1-methylimidazole-4-sulfonyl chloride and 0.34 ml (4.24 mmol) of pyridine in 5 ml of tetrahydrofuran.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1c[nH]cn1.C1CCCC1.c1ncc2cncn2n1 | HCl | O1CCCC1 | null | null | CCOc1ccc(N)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1.Cn1cnc(S(=O)(=O)Cl)c1>O1CCCC1>CCOc1ccc(NS(=O)(=O)c2cn(C)cn2)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4248acda9a694d5a88d9c4ff651bf639 | CCOc1ccc(N)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1.CN1CCN(S(=O)(=O)Cl)CC1>>CCOc1ccc(NS(=O)(=O)N2CCN(C)CC2)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 | NC=1C=CC(=C(C1)C1=NN2C(C(N1)=O)=C(N=C2C2CCCC2)C)OCC.CN1CCN(CC1)S(=O)(=O)Cl.N1=CC=CC=C1>>C(C)OC1=C(C=C(C=C1)NS(=O)(=O)N1CCN(CC1)C)C1=NN2C(C(N1)=O)=C(N=C2C2CCCC2)C | [CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([NH2:8])[cH:19][c:20]1-[c:21]1[n:22][n:23]2[c:24]([CH:25]3[CH2:26][CH2:27][CH2:28][CH2:29]3)[n:30][c:31]([CH3:32])[c:33]2[c:34](=[O:35])[nH:36]1.Cl[S:9](=[O:10])(=[O:11])[N:12]1[CH2:13][CH2:14][N:15]([CH3:16])[CH2:17][CH2:18]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([NH:8]... | CCOc1ccc(N)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1.CN1CCN(S(=O)(=O)Cl)CC1 | CCOc1ccc(NS(=O)(=O)N2CCN(C)CC2)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 | null | null | null | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 731ba8580d0b94af4c14395b28b15497fe9415881ff628fde46704f5dae9f0c1 | 0b04d60f6facec6a1319012378dc8ef969e966b0415fc012b8d425ffe424c0be | O=c1[nH]c(-c2cccc(NS(=O)(=O)N3CCNCC3)c2)nn2c(C3CCCC3)ncc12 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[#7:4](-[C:5])-[C:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C:5]-[#7:4](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10])-[C:6] | null | [] | null | null | null | null | 120 mg (0.34 mmol) of the compound from example 42A are reacted with 319 mg (1.36 mmol) of 4-methyl-1-piperazinesulfonyl chloride in 8 ml (98.9 mmol) of pyridine overnight.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonamide | null | null | c1ccccc1.C1C[NH]CC[NH]1.C1CCCC1.c1ncc2cncn2n1 | HCl | null | null | null | CCOc1ccc(N)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1.CN1CCN(S(=O)(=O)Cl)CC1>>CCOc1ccc(NS(=O)(=O)N2CCN(C)CC2)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8f314dafc04e4e4c80a2a27202844908 | CCCOc1ccc(N)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1.O=S(=O)(Cl)CCCCl>>CCCOc1ccc(NS(=O)(=O)CCCCl)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 | NC=1C=CC(=C(C1)C1=NN2C(C(N1)=O)=C(N=C2C2CCCC2)C)OCCC.ClCCCS(=O)(=O)Cl.N1=CC=CC=C1>>ClCCCS(=O)(=O)NC=1C=CC(=C(C1)C1=NN2C(C(N1)=O)=C(N=C2C2CCCC2)C)OCCC | [CH3:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([NH2:9])[cH:17][c:18]1-[c:19]1[n:20][n:21]2[c:22]([CH:23]3[CH2:24][CH2:25][CH2:26][CH2:27]3)[n:28][c:29]([CH3:30])[c:31]2[c:32](=[O:33])[nH:34]1.Cl[S:10](=[O:11])(=[O:12])[CH2:13][CH2:14][CH2:15][Cl:16]>>[CH3:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([NH:9][S:10](=[O... | CCCOc1ccc(N)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1.O=S(=O)(Cl)CCCCl | CCCOc1ccc(NS(=O)(=O)CCCCl)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 | null | null | ClCCl | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=c1[nH]c(-c2ccccc2)nn2c(C3CCCC3)ncc12 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4]-[C:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C:5]-[C:4]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | null | [] | null | null | null | null | 368 mg (1.0 mmol) of the compound from example 44A are reacted with 266 mg (1.5 mmol) of 3-chloropropanesulfonyl chloride and 0.81 ml (10.0 mmol) of pyridine in 12 ml of dichloromethane for 3 hours.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.C1CCCC1.c1ncc2cncn2n1 | HCl | ClCCl | null | null | CCCOc1ccc(N)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1.O=S(=O)(Cl)CCCCl>ClCCl>CCCOc1ccc(NS(=O)(=O)CCCCl)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-83fb6179414c4b0e8890d174f5a96b0d | CCCOc1ccc(N)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1.O=S(=O)(Cl)c1cccc2cccnc12>>CCCOc1ccc(NS(=O)(=O)c2cccc3cccnc23)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 | NC=1C=CC(=C(C1)C1=NN2C(C(N1)=O)=C(N=C2C2CCCC2)C)OCCC.N1=CC=CC2=CC=CC(=C12)S(=O)(=O)Cl.N1=CC=CC=C1>>N1=CC=CC2=CC=CC(=C12)S(=O)(=O)NC=1C=CC(=C(C1)C1=NN2C(C(N1)=O)=C(N=C2C2CCCC2)C)OCCC | [CH3:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([NH2:9])[cH:23][c:24]1-[c:25]1[n:26][n:27]2[c:28]([CH:29]3[CH2:30][CH2:31][CH2:32][CH2:33]3)[n:34][c:35]([CH3:36])[c:37]2[c:38](=[O:39])[nH:40]1.Cl[S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][cH:16][c:17]2[cH:18][cH:19][cH:20][n:21][c:22]12>>[CH3:1][CH2:2][CH2:3][O:4][... | CCCOc1ccc(N)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1.O=S(=O)(Cl)c1cccc2cccnc12 | CCCOc1ccc(NS(=O)(=O)c2cccc3cccnc23)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 | null | null | O1CCCC1 | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=c1[nH]c(-c2cccc(NS(=O)(=O)c3cccc4cccnc34)c2)nn2c(C3CCCC3)ncc12 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6](:[c:7]):[#7;a:8]:[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13])-[c:4](:[c:5]):[c:6](:[c:7]):[#7;a:8]:[c:9] | null | [] | null | null | null | null | 150 mg (0.408 mmol) of the compound from example 44A are reacted with 221 mg (0.96 mmol) of quinoline-8-sulfonyl chloride and 0.33 ml (4.08 mmol) of pyridine in 8 ml of tetrahydrofuran overnight.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccc2ncccc2c1.C1CCCC1.c1ncc2cncn2n1 | HCl | O1CCCC1 | null | null | CCCOc1ccc(N)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1.O=S(=O)(Cl)c1cccc2cccnc12>O1CCCC1>CCCOc1ccc(NS(=O)(=O)c2cccc3cccnc23)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-aacadcb6d93f471ea0451491c2eeebae | CCCOc1ccc(N)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1.CN1CCN(S(=O)(=O)Cl)CC1>>CCCOc1ccc(NS(=O)(=O)N2CCN(C)CC2)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 | NC=1C=CC(=C(C1)C1=NN2C(C(N1)=O)=C(N=C2C2CCCC2)C)OCCC.CN1CCN(CC1)S(=O)(=O)Cl.N1=CC=CC=C1>>CN1CCN(CC1)S(=O)(=O)NC=1C=CC(=C(C1)C1=NN2C(C(N1)=O)=C(N=C2C2CCCC2)C)OCCC | [CH3:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([NH2:9])[cH:20][c:21]1-[c:22]1[n:23][n:24]2[c:25]([CH:26]3[CH2:27][CH2:28][CH2:29][CH2:30]3)[n:31][c:32]([CH3:33])[c:34]2[c:35](=[O:36])[nH:37]1.Cl[S:10](=[O:11])(=[O:12])[N:13]1[CH2:14][CH2:15][N:16]([CH3:17])[CH2:18][CH2:19]1>>[CH3:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][cH... | CCCOc1ccc(N)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1.CN1CCN(S(=O)(=O)Cl)CC1 | CCCOc1ccc(NS(=O)(=O)N2CCN(C)CC2)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 | null | null | null | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 731ba8580d0b94af4c14395b28b15497fe9415881ff628fde46704f5dae9f0c1 | 0b04d60f6facec6a1319012378dc8ef969e966b0415fc012b8d425ffe424c0be | O=c1[nH]c(-c2cccc(NS(=O)(=O)N3CCNCC3)c2)nn2c(C3CCCC3)ncc12 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[#7:4](-[C:5])-[C:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C:5]-[#7:4](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10])-[C:6] | null | [] | null | null | null | null | 150 mg (0.408 mmol) of the compound from example 44A are treated with 576 mg (2.45 mmol) of 4-methyl-1-piperazinesulfonyl chloride in 6.6 ml (81.6 mmol) of pyridine for 3.5 hours.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonamide | null | null | c1ccccc1.C1C[NH]CC[NH]1.C1CCCC1.c1ncc2cncn2n1 | HCl | null | null | null | CCCOc1ccc(N)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1.CN1CCN(S(=O)(=O)Cl)CC1>>CCCOc1ccc(NS(=O)(=O)N2CCN(C)CC2)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3f190f042da046bd91a26572743fe5ea | CCCOc1ccc(N)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1.N#Cc1cccc(S(=O)(=O)Cl)c1>>CCCOc1ccc(NS(=O)(=O)c2cccc(C#N)c2)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 | NC=1C=CC(=C(C1)C1=NN2C(C(N1)=O)=C(N=C2C2CCCC2)C)OCCC.C(#N)C=1C=C(C=CC1)S(=O)(=O)Cl.N1=CC=CC=C1>>C(#N)C=1C=C(C=CC1)S(=O)(=O)NC=1C=CC(=C(C1)C1=NN2C(C(N1)=O)=C(N=C2C2CCCC2)C)OCCC | [CH3:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([NH2:9])[cH:21][c:22]1-[c:23]1[n:24][n:25]2[c:26]([CH:27]3[CH2:28][CH2:29][CH2:30][CH2:31]3)[n:32][c:33]([CH3:34])[c:35]2[c:36](=[O:37])[nH:38]1.Cl[S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][cH:16][c:17]([C:18]#[N:19])[cH:20]1>>[CH3:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][c... | CCCOc1ccc(N)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1.N#Cc1cccc(S(=O)(=O)Cl)c1 | CCCOc1ccc(NS(=O)(=O)c2cccc(C#N)c2)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 | null | null | O1CCCC1 | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=c1[nH]c(-c2cccc(NS(=O)(=O)c3ccccc3)c2)nn2c(C3CCCC3)ncc12 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | 200 mg (0.566 mmol) of the compound from example 44A are reaccted with 342 mg (1.70 mmol) of 3-cyanobenzenesulfonyl chloride and 0.46 ml (5.66 mmol) of pyridine in 15 ml of tetrahydrofuran overnight.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccccc1.C1CCCC1.c1ncc2cncn2n1 | HCl | O1CCCC1 | null | null | CCCOc1ccc(N)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1.N#Cc1cccc(S(=O)(=O)Cl)c1>O1CCCC1>CCCOc1ccc(NS(=O)(=O)c2cccc(C#N)c2)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4d9e804f0b394eed9538aa87ee8da3d0 | CCCOc1ccc(N)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1.CCCS(=O)(=O)Cl>>CCCOc1ccc(NS(=O)(=O)CCC)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 | NC=1C=CC(=C(C1)C1=NN2C(C(N1)=O)=C(N=C2C2CCCC2)C)OCCC.C(CC)S(=O)(=O)Cl.C(C)N(CC)CC>>C(CC)OC1=C(C=C(C=C1)NS(=O)(=O)CCC)C1=NN2C(C(N1)=O)=C(N=C2C2CCCC2)C | [CH3:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([NH2:9])[cH:16][c:17]1-[c:18]1[n:19][n:20]2[c:21]([CH:22]3[CH2:23][CH2:24][CH2:25][CH2:26]3)[n:27][c:28]([CH3:29])[c:30]2[c:31](=[O:32])[nH:33]1.Cl[S:10](=[O:11])(=[O:12])[CH2:13][CH2:14][CH3:15]>>[CH3:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([NH:9][S:10](=[O:11])(=... | CCCOc1ccc(N)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1.CCCS(=O)(=O)Cl | CCCOc1ccc(NS(=O)(=O)CCC)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 | null | null | O1CCCC1 | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=c1[nH]c(-c2ccccc2)nn2c(C3CCCC3)ncc12 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4]-[C:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C:5]-[C:4]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | null | [] | null | null | null | null | 150 mg (0.408 mmol) of the compound from example 44A are treated with 116 mg (0.816 mmol) of 1-propanesulfonyl chloride and 87 mg (0.816 mmol) of triethylamine in 15 ml of tetrahydrofuran for 1 hour.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.C1CCCC1.c1ncc2cncn2n1 | HCl | O1CCCC1 | null | null | CCCOc1ccc(N)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1.CCCS(=O)(=O)Cl>O1CCCC1>CCCOc1ccc(NS(=O)(=O)CCC)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0d637d190c36455992e0de19f9749e14 | CCOc1ccc(N)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1.COc1ccc(CC(=O)Cl)cc1OC>>CCOc1ccc(NC(=O)Cc2ccc(OC)c(OC)c2)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 | NC=1C=CC(=C(C1)C1=NN2C(C(N1)=O)=C(N=C2C2CCCC2)C)OCC.COC=1C=C(C=CC1OC)CC(=O)Cl.N1=CC=CC=C1>>COC=1C=C(C=CC1OC)CC(=O)NC=1C=CC(=C(C1)C1=NN2C(C(N1)=O)=C(N=C2C2CCCC2)C)OCC | [CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([NH2:8])[cH:22][c:23]1-[c:24]1[n:25][n:26]2[c:27]([CH:28]3[CH2:29][CH2:30][CH2:31][CH2:32]3)[n:33][c:34]([CH3:35])[c:36]2[c:37](=[O:38])[nH:39]1.Cl[C:9](=[O:10])[CH2:11][c:12]1[cH:13][cH:14][c:15]([O:16][CH3:17])[c:18]([O:19][CH3:20])[cH:21]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c... | CCOc1ccc(N)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1.COc1ccc(CC(=O)Cl)cc1OC | CCOc1ccc(NC(=O)Cc2ccc(OC)c(OC)c2)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 | null | null | O1CCCC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Cc1ccccc1)Nc1cccc(-c2nn3c(C4CCCC4)ncc3c(=O)[nH]2)c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3]-[c:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | null | null | Analogously to the preparation of example 46, 100 mg (0.283 mmol) of the compound from example 42A are reacted with 182 mg (0.849 mmol) of 3,4-dimethoxyphenylacetyl chloride and 0.23 ml (2.84 mmol) of pyridine in 6 ml of tetrahydrofuran.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.C1CCCC1.c1ncc2cncn2n1 | HCl | O1CCCC1 | null | null | CCOc1ccc(N)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1.COc1ccc(CC(=O)Cl)cc1OC>O1CCCC1>CCOc1ccc(NC(=O)Cc2ccc(OC)c(OC)c2)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dad14497ec5c4cf081a9bff140e7ecfa | CCOc1ccc(NC(=O)C2CN(C(=O)OC(C)(C)C)CCN2C(=O)OC(C)(C)C)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1>>CCOc1ccc(NC(=O)C2CNCCN2)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 | C(C)(C)(C)OC(=O)N1C(CN(CC1)C(=O)OC(C)(C)C)C(=O)NC=1C=CC(=C(C1)C1=NN2C(C(N1)=O)=C(N=C2C2CCCC2)C)OCC.FC(C(=O)O)(F)F>>C(C)OC1=C(C=C(C=C1)NC(=O)C1NCCNC1)C1=NN2C(C(N1)=O)=C(N=C2C2CCCC2)C | CC(C)(C)OC(=O)[N:13]1[CH2:12][CH:11]([C:9]([NH:8][c:7]2[cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[c:18](-[c:19]3[n:20][n:21]4[c:22]([CH:23]5[CH2:24][CH2:25][CH2:26][CH2:27]5)[n:28][c:29]([CH3:30])[c:31]4[c:32](=[O:33])[nH:34]3)[cH:17]2)=[O:10])[N:16](C(=O)OC(C)(C)C)[CH2:15][CH2:14]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c... | CCOc1ccc(NC(=O)C2CN(C(=O)OC(C)(C)C)CCN2C(=O)OC(C)(C)C)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 | CCOc1ccc(NC(=O)C2CNCCN2)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 | null | null | null | Reduction | OtherReaction | 5dc6a6e72b840f8254dd5d683a72ad117110578e0dccad8ab46ac333e532cdb4 | 62d6d161f7b7b3cc63e568e66451a46259e0e34072c373a60dd8b9591af3c67b | O=C(Nc1cccc(-c2nn3c(C4CCCC4)ncc3c(=O)[nH]2)c1)C1CNCCN1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3](-[C:4](=[O;D1;H0:5])-[#7:6]-[c:7])-[N;H0;D3;+0:8](-C(=O)-O-C(-C)(-C)-C)-[C:9]-[C:10]-1>>[O;D1;H0:5]=[C:4](-[#7:6]-[c:7])-[C:3]1-[C:2]-[NH;D2;+0:1]-[C:10]-[C:9]-[NH;D2;+0:8]-1 | null | [] | null | null | null | null | 132 mg (0.198 mmol) of the compound from example 48 are treated with 5 ml of trifluoroacetic acid for 90 minutes; the solution is then concentrated, dichloromethane and 10% strength NaHCO3 solution are added to the residue and the organic phase is dried and concentrated under reduced pressure.
Conditions: See reaction.... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carbamic ester.Ether.Ether.Boc.Boc | Secondary amine.Secondary amine | C1C[NH]CC[NH]1 | C1CNCCN1 | c1ccccc1.C1CNCCN1.C1CCCC1.c1ncc2cncn2n1 | HO- | null | null | null | CCOc1ccc(NC(=O)C2CN(C(=O)OC(C)(C)C)CCN2C(=O)OC(C)(C)C)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1>>CCOc1ccc(NC(=O)C2CNCCN2)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9b6acc6d97074603b60437d04dd0503a | CCCOc1ccc(N)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1.O=C=NS(=O)(=O)c1ccc(F)cc1>>CCCOc1ccc(NC(=O)NS(=O)(=O)c2ccc(F)cc2)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 | NC=1C=CC(=C(C1)C1=NN2C(C(N1)=O)=C(N=C2C2CCCC2)C)OCCC.FC1=CC=C(C=C1)S(=O)(=O)N=C=O>>C1(CCCC1)C1=NC(=C2C(NC(=NN21)C=2C=C(C=CC2OCCC)NC(=O)NS(=O)(=O)C2=CC=C(C=C2)F)=O)C | [CH3:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([NH2:9])[cH:23][c:24]1-[c:25]1[n:26][n:27]2[c:28]([CH:29]3[CH2:30][CH2:31][CH2:32][CH2:33]3)[n:34][c:35]([CH3:36])[c:37]2[c:38](=[O:39])[nH:40]1.[C:10](=[O:11])=[N:12][S:13](=[O:14])(=[O:15])[c:16]1[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]1>>[CH3:1][CH2:2][CH2:3][O:4][... | CCCOc1ccc(N)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1.O=C=NS(=O)(=O)c1ccc(F)cc1 | CCCOc1ccc(NC(=O)NS(=O)(=O)c2ccc(F)cc2)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 | null | null | O1CCCC1 | Acylation | Urea synthesis via isocyanate and primary amine | b2f9721fe12517bb4ddb059bee81df64632e89cc2635ea9f7de5f84d579af016 | ad01beb75a98e2ae01d9fc14d1face2625004bf1eae4aa0352da70e1110fdd06 | O=C(Nc1cccc(-c2nn3c(C4CCCC4)ncc3c(=O)[nH]2)c1)NS(=O)(=O)c1ccccc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C;H0;D2;+0:6]=[N;H0;D2;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11]>>[O;D1;H0:5]=[C;H0;D3;+0:6](-[NH;D2;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | The preparation is carried out analogously to the procedure of example 54 using 150 mg (0.408 mmol) of the amino compound from example 44A and 411 mg (2.04 mmol) of 4-fluorobenzenesulfonyl isocyanate in 12 ml of tetrahydrofuran, which are reacted overnight.
Conditions: See reaction.notes.procedure_details.
Workup: are ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonamide.Urea | null | null | c1ccccc1.c1ccccc1.C1CCCC1.c1ncc2cncn2n1 | null | O1CCCC1 | null | null | CCCOc1ccc(N)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1.O=C=NS(=O)(=O)c1ccc(F)cc1>O1CCCC1>CCCOc1ccc(NC(=O)NS(=O)(=O)c2ccc(F)cc2)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2be7a9882b7244f6a12167edeefaa867 | CN.O=C=Nc1ccc(Cl)cc1Cl>>CNC(=O)Nc1ccc(Cl)cc1Cl | CN.CCO.ClC1=C(C=CC(=C1)Cl)N=C=O>>ClC1=C(C=CC(=C1)Cl)NC(=O)NC | [CH3:1][NH2:2].[C:3](=[O:4])=[N:5][c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][c:12]1[Cl:13]>>[CH3:1][NH:2][C:3](=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][c:12]1[Cl:13] | CN.O=C=Nc1ccc(Cl)cc1Cl | CNC(=O)Nc1ccc(Cl)cc1Cl | null | null | C1CCOC1 | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1ccccc1 | [C;D1;H3:1]-[NH2;D1;+0:2].[O;D1;H0:3]=[C;H0;D2;+0:4]=[N;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:1]-[NH;D2;+0:2]-[C;H0;D3;+0:4](=[O;D1;H0:3])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 74 | [{"value": 74.0, "product": "ClC1=C(C=CC(=C1)Cl)NC(=O)NC", "details": "PERCENTYIELD", "is_desired": false}] | 65 | CELSIUS | null | null | A cooled (0° C.) solution of methylamine in EtOH (50 mL, 400 mmol, 8.0 M) in anhydrous THF (300 mL) was treated with 2,4-dichlorophenylisocyanate (25.0 g, 133 mmol). The cooling bath was removed and the mixture was warmed to 65° C. for 20 min. The reaction mixture was then cooled to 0° C. The solid was collected on a B... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1 | null | C1CCOC1 | 65 | null | CN.O=C=Nc1ccc(Cl)cc1Cl>C1CCOC1>CNC(=O)Nc1ccc(Cl)cc1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3d249bf89540417d93e908299e457114 | CNC(=O)Nc1ccc(Cl)cc1Cl.N#CCC(=O)O>>Cn1c(=O)cc(N)n(-c2ccc(Cl)cc2Cl)c1=O | C(#N)CC(=O)O.C(#N)CC(=O)O.ClC1=C(C=CC(=C1)Cl)NC(=O)NC.C(#N)CC(=O)O.C(C)(=O)OC(C)=O>>NC1=CC(N(C(N1C1=C(C=C(C=C1)Cl)Cl)=O)C)=O | [CH3:1][NH:2][C:17]([NH:8][c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][c:15]1[Cl:16])=[O:18].O[C:3](=[O:4])[CH2:5][C:6]#[N:7]>>[CH3:1][n:2]1[c:3](=[O:4])[cH:5][c:6]([NH2:7])[n:8](-[c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][c:15]2[Cl:16])[c:17]1=[O:18] | CNC(=O)Nc1ccc(Cl)cc1Cl.N#CCC(=O)O | Cn1c(=O)cc(N)n(-c2ccc(Cl)cc2Cl)c1=O | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 37fdb1a5022d4bd5c972a75f4cc768afdba842f7789da08aa6c01e32589f7582 | af82df267895f3cfbd051540e8a5c0059411ca821f7ab52cc8fadf01df4176fe | O=c1ccn(-c2ccccc2)c(=O)[nH]1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[C;H0;D2;+0:4]#[N;H0;D1;+0:5].[C;D1;H3:6]-[NH;D2;+0:7]-[C;H0;D3;+0:8](=[O;D1;H0:9])-[NH;D2;+0:10]-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14](-[Cl;D1;H0:15]):[c:16]>>[C;D1;H3:6]-[n;H0;D3;+0:7]1:[c;H0;D3;+0:8](=[O;D1;H0:9]):[n;H0;D3;+0:10](-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14](-... | 54 | [{"value": 54.0, "product": "NC1=CC(N(C(N1C1=C(C=C(C=C1)Cl)Cl)=O)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | 45 | MINUTE | A solution of N-(2,4-dichlorophenyl)-N′-methyl-urea (12.0 g, 54.8 mmol) in acetic anhydride (100 mL) was treated with cyanoacetic acid (5.6 g, 65.8 mmol). The reaction mixture was heated at 85° C. for 2.5 h. Additional cyanoacetic acid (0.90 g, 11.0 mmol) was added and the reaction mixture was stirred for 45 min. A thi... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Urea.Nitrile | Primary amine | null | c1cncnc1 | c1cncnc1.c1ccccc1 | HO- | null | 85 | 0.75 | CNC(=O)Nc1ccc(Cl)cc1Cl.N#CCC(=O)O>>Cn1c(=O)cc(N)n(-c2ccc(Cl)cc2Cl)c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a85b175f5e694e069515cd19d8b62070 | CCCC(CCC)n1c(CC)nc2c1c(=O)n(C)c(=O)n2Cc1ccc(OC)cc1>>CCCC(CCC)n1c(CC)nc2[nH]c(=O)n(C)c(=O)c21 | C(C)C1=NC=2N(C(N(C(C2N1C(CCC)CCC)=O)C)=O)CC1=CC=C(C=C1)OC>>C(C)C1=NC=2NC(N(C(C2N1C(CCC)CCC)=O)C)=O | COc1ccc(C[n:14]2[c:13]3[n:12][c:9]([CH2:10][CH3:11])[n:8]([CH:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])[c:21]3[c:19](=[O:20])[n:17]([CH3:18])[c:15]2=[O:16])cc1>>[CH3:1][CH2:2][CH2:3][CH:4]([CH2:5][CH2:6][CH3:7])[n:8]1[c:9]([CH2:10][CH3:11])[n:12][c:13]2[nH:14][c:15](=[O:16])[n:17]([CH3:18])[c:19](=[O:20])[c:21]12 | CCCC(CCC)n1c(CC)nc2c1c(=O)n(C)c(=O)n2Cc1ccc(OC)cc1 | CCCC(CCC)n1c(CC)nc2[nH]c(=O)n(C)c(=O)c21 | null | null | FC(C(=O)O)(F)F | Reduction | OtherReaction | 237d3641c4592421b3cdfdc3e5e3d949bb5ae1a6adfa00ea7c0c211743e468b6 | 84394d34c591024a84d9393eb3e8adb8ada5a6225c3abafc4dae9aedd4568be4 | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | C-O-c1:c:c:c(-C-[n;H0;D3;+0:1]2:[c:2]3:[#7;a:3]:[c:4]:[#7;a:5](-[C:6]):[c:7]:3:[c:8]:[#7;a:9](-[C;D1;H3:10]):[c:11]:2=[O;D1;H0:12]):c:c:1>>[C:6]-[#7;a:5]1:[c:4]:[#7;a:3]:[c:2]2:[nH;D2;+0:1]:[c:11](=[O;D1;H0:12]):[#7;a:9](-[C;D1;H3:10]):[c:8]:[c:7]:1:2 | 91 | [{"value": 91.0, "product": "C(C)C1=NC=2NC(N(C(C2N1C(CCC)CCC)=O)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 8-ethyl-7-(4-heptyl)-3-(4-methoxybenzyl)-1-methyl-3,7-dihydro-1H-purine-2,6-dione in trifluoroacetic acid was heated at 100° C. in a sealed tube for 8 h. The mixture was cooled to r.t. and concentrated. The residue was transferred into a separatory funnel containing saturated aqueous NaHCO3 (20 mL) and th... | 10.6084/m9.figshare.5104873.v1 | null | Ether | null | c1ccccc1.c1ncc2nc[nH]c2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | HO- | FC(C(=O)O)(F)F | null | null | CCCC(CCC)n1c(CC)nc2c1c(=O)n(C)c(=O)n2Cc1ccc(OC)cc1>FC(C(=O)O)(F)F>CCCC(CCC)n1c(CC)nc2[nH]c(=O)n(C)c(=O)c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bb30373df9eb45569b1a021302201d7c | NC1CCCCC1.O=[N+]([O-])c1cccnc1Cl>>O=[N+]([O-])c1cccnc1NC1CCCCC1 | C([O-])([O-])=O.[K+].[K+].ClC1=NC=CC=C1[N+](=O)[O-].C1(CCCCC1)N>>C1(CCCCC1)NC1=NC=CC=C1[N+](=O)[O-] | [NH2:10][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1.Cl[c:9]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][cH:6][cH:7][n:8]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][n:8][c:9]1[NH:10][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1 | NC1CCCCC1.O=[N+]([O-])c1cccnc1Cl | O=[N+]([O-])c1cccnc1NC1CCCCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(NC2CCCCC2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[C:7]-[C:8](-[NH2;D1;+0:9])-[C:10]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8](-[C:7])-[C:10]):[#7;a:2]:[c:3] | null | [] | null | null | null | null | A mixture composed of 0.1 mol (15.85 g) of 2-chloro-3-nitropyridine and 0.1 mol (11.50 ml) of cyclohexylamine is heated at 120° C. for 4 hours in 250 ml of DMF in the presence of potassium carbonate (13.81 g). The solution is then extracted with 200 ml of ether and the organic phase is washed three times with water. Af... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.C1CCCCC1 | HCl | CN(C)C=O | null | null | NC1CCCCC1.O=[N+]([O-])c1cccnc1Cl>CN(C)C=O>O=[N+]([O-])c1cccnc1NC1CCCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b54805a8be0d4495a08ee3d78f19e951 | CCCNCCC.CCOC(=O)N=C=S.Nc1cccnc1NC1CCCCC1>>CCOC(=O)NC(=Nc1cccnc1NC1CCCCC1)N(CC)CC | NC=1C(=NC=CC1)NC1CCCCC1.C(C)OC(=O)N=C=S.C(CC)NCCC>>C1(CCCCC1)NC1=NC=CC=C1N=C(N(CC)CC)NC(OCC)=O | C[CH2:24][CH2:23][NH:22][CH2:25][CH2:26]C.S=[C:7]=[N:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[NH2:8][c:9]1[cH:10][cH:11][cH:12][n:13][c:14]1[NH:15][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[NH:6][C:7](=[N:8][c:9]1[cH:10][cH:11][cH:12][n:13][c:14]1[NH:15][CH:16]1[CH2:17][CH2:18][CH2:1... | CCCNCCC.CCOC(=O)N=C=S.Nc1cccnc1NC1CCCCC1 | CCOC(=O)NC(=Nc1cccnc1NC1CCCCC1)N(CC)CC | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 139e28d21aa928cab79eda2c8e29e732622f5aad4fa7a5110f52babd56850fd5 | f04610dab290923496c274c83536221381be1f3e34fba8a6c2c346d3c887dbc6 | c1ccc(NC2CCCCC2)nc1 | C-[CH2;D2;+0:1]-[C:2]-[NH;D2;+0:3]-[C:4]-[CH2;D2;+0:5]-C.S=[C;H0;D2;+0:6]=[N;H0;D2;+0:7]-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11].[#7:12]-[c:13](:[#7;a:14]:[c:15]):[c:16](-[NH2;D1;+0:17]):[c:18]>>[#7:12]-[c:13](:[#7;a:14]:[c:15]):[c:16](-[N;H0;D2;+0:17]=[C;H0;D3;+0:6](-[NH;D2;+0:7]-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11])-[N;H0;D... | null | [] | 0 | CELSIUS | 15 | MINUTE | A mixture of 0.02 mol (3.82 g) of 3-amino-2-cyclohexylaminopyridine from Preparation 1 and 0.02 mol of ethoxycarbonyl isothiocyanate is stirred in 50 ml of DMF at ambient temperature for 3 hours. The solution is then cooled to 0° C., and 0.05 mol of dipropylamine and then 0.02 mol of mercuric chloride are added in succ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine.Isothiocyanate | Carbamic ester.Tertiary amine | null | null | c1ccncc1.C1CCCCC1 | Other | CN(C)C=O | 0 | 0.25 | CCCNCCC.CCOC(=O)N=C=S.Nc1cccnc1NC1CCCCC1>CN(C)C=O>CCOC(=O)NC(=Nc1cccnc1NC1CCCCC1)N(CC)CC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e6a7c11947ea4ca0a6586f1135d10672 | Nc1cccnc1NC1CCCCC1.Nc1cccnc1NC1CCCCCCC1>>Nc1nc2cccnc2n1C1CCCCCCC1 | NC=1C(=NC=CC1)NC1CCCCCCC1.NC=1C(=NC=CC1)NC1CCCCC1>>C1(CCCCCCC1)N1C(=NC=2C1=NC=CC2)N | c1cnc(NC2CCCCC2)[c:2]([NH2:1])c1.[NH2:3][c:4]1[cH:5][cH:6][cH:7][n:8][c:9]1[NH:10][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1>>[NH2:1][c:2]1[n:3][c:4]2[cH:5][cH:6][cH:7][n:8][c:9]2[n:10]1[CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1 | Nc1cccnc1NC1CCCCC1.Nc1cccnc1NC1CCCCCCC1 | Nc1nc2cccnc2n1C1CCCCCCC1 | null | null | null | Miscellaneous | OtherReaction | 1696617b8627b69f7db60c2f1f442ace52fef55762c1aef0718f678db1d213a3 | 75e55b02fbc70cd4854517e7b01bad5180bb695773feca53d4b81d2577de724c | c1cnc2c(c1)ncn2C1CCCCCCC1 | [C:1]-[C:2](-[NH;D2;+0:3]-[c:4](:[#7;a:5]:[c:6]):[c:7](-[NH2;D1;+0:8]):[c:9])-[C:10].[N;D1;H2:11]-[c;H0;D3;+0:12]1:c:c:c:n:c:1-N-C1-C-C-C-C-C-1>>[C:1]-[C:2](-[n;H0;D3;+0:3]1:[c:4](:[#7;a:5]:[c:6]):[c:7](:[c:9]):[n;H0;D2;+0:8]:[c;H0;D3;+0:12]:1-[N;D1;H2:11])-[C:10] | null | [] | null | null | null | null | The experimental protocol is identical with that used in Example 1, starting in Step a from 3-amino-2-cyclooctylaminopyridine of Preparation 3 instead of 3-amino-2-cyclohexylaminopyridine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine.Secondary amine | null | c1ccncc1.C1CCCCC1.c1ccncc1 | c1nc2ncccc2[nH]1 | c1nc2ncccc2[nH]1.C1CCCCCCC1 | Other | null | null | null | Nc1cccnc1NC1CCCCC1.Nc1cccnc1NC1CCCCCCC1>>Nc1nc2cccnc2n1C1CCCCCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8ea1cda49e264bc9a81bb645c5445dd3 | CC(=O)N[C@@H]1[C@@H](OCc2ccccc2)[C@H](F)[C@@H](COCc2ccccc2)O[C@@]1(O)Cc1ccccc1>>CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](F)[C@@H]1O | C(C1=CC=CC=C1)[C@@]1(O)[C@@H]([C@@H](OCC2=CC=CC=C2)[C@@H]([C@H](O1)COCC1=CC=CC=C1)F)NC(C)=O>>C(C)(=O)N[C@H]1C(O)O[C@@H]([C@H]([C@@H]1O)F)CO | c1ccc(C[C@@:6]2([OH:7])[C@H:5]([NH:4][C:2]([CH3:1])=[O:3])[C@@H:14]([O:15]Cc3ccccc3)[C@H:12]([F:13])[C@@H:9]([CH2:10][O:11]Cc3ccccc3)[O:8]2)cc1>>[CH3:1][C:2](=[O:3])[NH:4][C@H:5]1[CH:6]([OH:7])[O:8][C@H:9]([CH2:10][OH:11])[C@@H:12]([F:13])[C@@H:14]1[OH:15] | CC(=O)N[C@@H]1[C@@H](OCc2ccccc2)[C@H](F)[C@@H](COCc2ccccc2)O[C@@]1(O)Cc1ccccc1 | CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](F)[C@@H]1O | null | [Pd].C.[Pd].C | CC(=O)O | Deprotection | OtherReaction | 894943b528b8f18625ba0cdb2613d4f97d9d9b6a9174d3e6e6a9c9e48ee2d622 | 0a54dce4bd86fe519a6d27bb79e763ae80051263fc7e4bc325885d62f2298da9 | C1CCOCC1 | [C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[C:5]1-[C:6](-[O;H0;D2;+0:7]-C-c2:c:c:c:c:c:2)-[C:8]-[C:9](-[C:10]-[O;H0;D2;+0:11]-C-c2:c:c:c:c:c:2)-[#8:12]-[C@@;H0;D4;+0:13]-1(-[O;D1;H1:14])-C-c1:c:c:c:c:c:1>>[C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[C:5]1-[C:6](-[OH;D1;+0:7])-[C:8]-[C:9](-[C:10]-[OH;D1;+0:11])-[#8:12]-[CH;D3;+0... | null | [] | null | null | 5 | DAY | A solution of benzyl2-acetamido-3,6-di-O-benzyl-2,4-dideoxy-4-fluoro-α-D-glucopyranose (3.21 g, 6.51 mmol) in the HOAc (150 ml) containing 10% Pd/charcoal catalyst (4.3 g) was hydrogenated at 50–55 psig. Pressure dropped from 55 to 50 psig and was re-pressurized to 56 psig. Again, pressure dropped to approximately 50 p... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Tertiary alcohol | Ether.Primary alcohol.Secondary alcohol.Secondary alcohol | c1ccccc1.C1CCOCC1.c1ccccc1.c1ccccc1 | C1CCOCC1 | C1CCOCC1 | Other | [Pd].C.[Pd].C.CC(=O)O | null | 120 | CC(=O)N[C@@H]1[C@@H](OCc2ccccc2)[C@H](F)[C@@H](COCc2ccccc2)O[C@@]1(O)Cc1ccccc1>[Pd].C.[Pd].C.CC(=O)O>CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](F)[C@@H]1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b0be1cdcacc84eba961a19d40c95eb26 | CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](F)[C@@H]1O.CC(=O)OC(C)=O>>CC(=O)N[C@H]1C(OC(C)=O)O[C@H](COC(C)=O)[C@@H](F)[C@@H]1OC(C)=O | C(C)(=O)N[C@H]1C(O)O[C@@H]([C@H]([C@@H]1O)F)CO.C(C)(=O)OC(C)=O>>C(C)(=O)N[C@H]1C(OC(C)=O)O[C@@H]([C@H]([C@@H]1OC(C)=O)F)COC(C)=O | [CH3:1][C:2](=[O:3])[NH:4][C@H:5]1[CH:6]([OH:7])[O:11][C@H:12]([CH2:13][OH:14])[C@@H:18]([F:19])[C@@H:20]1[OH:21].[C:8]([CH3:9])(=[O:10])[O:17][C:22]([CH3:23])=[O:24]>>[CH3:1][C:2](=[O:3])[NH:4][C@H:5]1[CH:6]([O:7][C:8]([CH3:9])=[O:10])[O:11][C@H:12]([CH2:13][O:14][C:15]([CH3:16])=[O:17])[C@@H:18]([F:19])[C@@H:20]1[O:2... | CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](F)[C@@H]1O.CC(=O)OC(C)=O | CC(=O)N[C@H]1C(OC(C)=O)O[C@H](COC(C)=O)[C@@H](F)[C@@H]1OC(C)=O | null | null | N1=CC=CC=C1 | Acylation | OtherReaction | afe461ca434c64275466a154f78a94b0303e569ba286fa248531b7f1e77cf022 | 738fa43570c80d19bcdea4bbd7c858580f14f220b5f6c9f8aa38d4ba13feacfe | C1CCOCC1 | [C;D1;H3:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[C;H0;D3;+0:5](-[C;D1;H3:6])=[O;D1;H0:7].[OH;D1;+0:8]-[C:9]-[C:10]1-[#8:11]-[C:12](-[OH;D1;+0:13])-[C:14]-[C:15](-[OH;D1;+0:16])-[C:17]-1>>[C;D1;H3:18]-[C:19](=[O;H0;D1;+0:4])-[O;H0;D2;+0:8]-[C:9]-[C:10]1-[#8:11]-[C:12](-[O;H0;D2;+0:13]-[C;H0;D3;+0:5](-[C;D1;H3:6]... | null | [] | null | null | 24 | HOUR | A solution of 2-acetamido-4-fluoro-2,4-dideoxy-D-glucopyranose (1.35 g, 6.048 mmol) in a mixture of pyridine (50 ml) and acetic anhydride (25 ml, 27 g, 264 mmol) was stirred at room temperature for 24 hours at which time no starting material but two close spots appeared by TLC. Stirring continued for another 15 hours. ... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary alcohol.Secondary alcohol.Secondary alcohol | Ester.Ester.Ester | null | null | C1CCOCC1 | Other | N1=CC=CC=C1 | null | 24 | CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](F)[C@@H]1O.CC(=O)OC(C)=O>N1=CC=CC=C1>CC(=O)N[C@H]1C(OC(C)=O)O[C@H](COC(C)=O)[C@@H](F)[C@@H]1OC(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-52e4e58da95a46789156c6f37fe17043 | CC(=O)NC1CNC(C)C1.O=C(O)c1cn(C2CC2)c2cc(Cl)c(F)cc2c1=O>>CC(=O)NC1CC(C)N(c2cc3c(cc2F)c(=O)c(C(=O)O)cn3C2CC2)C1 | C1(CC1)N1C=C(C(C2=CC(=C(C=C12)Cl)F)=O)C(=O)O.C(C)(=O)NC1CNC(C1)C>>C1(CC1)N1C=C(C(C2=CC(=C(C=C12)N1CC(CC1C)NC(C)=O)F)=O)C(=O)O | [CH3:1][C:2](=[O:3])[NH:4][CH:5]1[CH2:6][CH:7]([CH3:8])[NH:9][CH2:28]1.Cl[c:10]1[cH:11][c:12]2[c:13]([cH:14][c:15]1[F:16])[c:17](=[O:18])[c:19]([C:20](=[O:21])[OH:22])[cH:23][n:24]2[CH:25]1[CH2:26][CH2:27]1>>[CH3:1][C:2](=[O:3])[NH:4][CH:5]1[CH2:6][CH:7]([CH3:8])[N:9]([c:10]2[cH:11][c:12]3[c:13]([cH:14][c:15]2[F:16])[c... | CC(=O)NC1CNC(C)C1.O=C(O)c1cn(C2CC2)c2cc(Cl)c(F)cc2c1=O | CC(=O)NC1CC(C)N(c2cc3c(cc2F)c(=O)c(C(=O)O)cn3C2CC2)C1 | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 89f800d0b5c6eace023ec0f16ed65844f5dd409e156b3b4845e1db5de9a38872 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1ccn(C2CC2)c2cc(N3CCCC3)ccc12 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[c:4]:[c:5]:[c:6]:1-[F;D1;H0:7]):[#7;a:8](-[C:9]):[c:10].[C;D1;H3:11]-[C:12]1-[C:13]-[C:14]-[C:15]-[NH;D2;+0:16]-1>>[C:9]-[#7;a:8](:[c:10]):[c:3]1:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:16]2-[C:15]-[C:14]-[C:13]-[C:12]-2-[C;D1;H3:11]):[c:6](-[F;D1;H0:7]):[c:5]:[c:4]:1 | null | [] | null | null | null | null | The condensation of 1-cyclopropyl-6-fluoro-7-chloro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid with 3-acetamido-5-methylpyrrolidine in a similar manner as described in example 1 give the titled product. Yield (68%), m.p 270–72° C., C20H22FN3O4, m/z 388 (M+1).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccc2ncccc2c1 | C1CC[NH]C1.c1ccc2ncccc2c1 | C1CC[NH]C1.c1ccc2ncccc2c1.C1CC1 | HCl | null | null | null | CC(=O)NC1CNC(C)C1.O=C(O)c1cn(C2CC2)c2cc(Cl)c(F)cc2c1=O>>CC(=O)NC1CC(C)N(c2cc3c(cc2F)c(=O)c(C(=O)O)cn3C2CC2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-27c06f800c23468692cd6929498a301c | CCOC1CCNCC1.Cc1c(F)c(F)cc2c1c(=O)c(C(=O)O)cn2C1CC1>>CCOC1CCN(c2cc3c(c(C)c2F)c(=O)c(C(=O)O)cn3C2CC2)CC1 | C1(CC1)N1C=C(C(C2=C(C(=C(C=C12)F)F)C)=O)C(=O)O.C(C)OC1CCNCC1>>C1(CC1)N1C=C(C(C2=C(C(=C(C=C12)N1CCC(CC1)OCC)F)C)=O)C(=O)O | [CH3:1][CH2:2][O:3][CH:4]1[CH2:5][CH2:6][NH:7][CH2:27][CH2:28]1.F[c:8]1[cH:9][c:10]2[c:11]([c:12]([CH3:13])[c:14]1[F:15])[c:16](=[O:17])[c:18]([C:19](=[O:20])[OH:21])[cH:22][n:23]2[CH:24]1[CH2:25][CH2:26]1>>[CH3:1][CH2:2][O:3][CH:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][c:10]3[c:11]([c:12]([CH3:13])[c:14]2[F:15])[c:16](=[O:... | CCOC1CCNCC1.Cc1c(F)c(F)cc2c1c(=O)c(C(=O)O)cn2C1CC1 | CCOC1CCN(c2cc3c(c(C)c2F)c(=O)c(C(=O)O)cn3C2CC2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 6ca896bdf5cf17e98a9402041cc62e117ebb3e6ff582ec413fbc5219ab9874c5 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1ccn(C2CC2)c2cc(N3CCCCC3)ccc12 | F-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[c:4]:[c:5]:[c:6]:1-[F;D1;H0:7]):[#7;a:8](-[C:9]):[c:10].[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]>>[C:9]-[#7;a:8](:[c:10]):[c:3]1:[c:4]:[c:5]:[c:6](-[F;D1;H0:7]):[c;H0;D3;+0:1](-[N;H0;D3;+0:13](-[C:12]-[C:11])-[C:14]-[C:15]):[c:2]:1 | 40 | [{"value": 40.0, "product": "C1(CC1)N1C=C(C(C2=C(C(=C(C=C12)N1CCC(CC1)OCC)F)C)=O)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The condensation of 1-cyclopropyl-6,7-difluoro-5-methyl-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid with 4-ethoxypiperidine in a similar manner as described in example 1 give the titled product. Yield 40%, m.p 180–82° C., C21H21FN2O4, m/z 388 (M+1).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNCC1.c1ccc2ncccc2c1 | C1CC[NH]CC1.c1ccc2ncccc2c1 | C1CC[NH]CC1.c1ccc2ncccc2c1.C1CC1 | HF | null | null | null | CCOC1CCNCC1.Cc1c(F)c(F)cc2c1c(=O)c(C(=O)O)cn2C1CC1>>CCOC1CCN(c2cc3c(c(C)c2F)c(=O)c(C(=O)O)cn3C2CC2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d6518f5867684008afb4656f45b62e52 | CC1CCC(N)N1.Nc1c(F)c(F)c(F)c2c1c(=O)c(C(=O)O)cn2C1CC1>>CC1CCC(N)N1c1c(F)c(N)c2c(=O)c(C(=O)O)cn(C3CC3)c2c1F | NC1=C2C(C(=CN(C2=C(C(=C1F)F)F)C1CC1)C(=O)O)=O.NC1CCC(N1)C>>NC1=C2C(C(=CN(C2=C(C(=C1F)N1C(CCC1N)C)F)C1CC1)C(=O)O)=O | [CH3:1][CH:2]1[CH2:3][CH2:4][CH:5]([NH2:6])[NH:7]1.F[c:8]1[c:9]([F:10])[c:11]([NH2:12])[c:13]2[c:14](=[O:15])[c:16]([C:17](=[O:18])[OH:19])[cH:20][n:21]([CH:22]3[CH2:23][CH2:24]3)[c:25]2[c:26]1[F:27]>>[CH3:1][CH:2]1[CH2:3][CH2:4][CH:5]([NH2:6])[N:7]1[c:8]1[c:9]([F:10])[c:11]([NH2:12])[c:13]2[c:14](=[O:15])[c:16]([C:17]... | CC1CCC(N)N1.Nc1c(F)c(F)c(F)c2c1c(=O)c(C(=O)O)cn2C1CC1 | CC1CCC(N)N1c1c(F)c(N)c2c(=O)c(C(=O)O)cn(C3CC3)c2c1F | null | null | null | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 89f800d0b5c6eace023ec0f16ed65844f5dd409e156b3b4845e1db5de9a38872 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1ccn(C2CC2)c2cc(N3CCCC3)ccc12 | F-[c;H0;D3;+0:1]1:[c:2](-[F;D1;H0:3]):[c:4](:[c:5]:[c:6]:[c:7]:1-[F;D1;H0:8]):[#7;a:9](-[C:10]):[c:11].[C;D1;H3:12]-[C:13]1-[C:14]-[C:15]-[C:16](-[N;D1;H2:17])-[NH;D2;+0:18]-1>>[C:10]-[#7;a:9](:[c:11]):[c:4]1:[c:5]:[c:6]:[c:7](-[F;D1;H0:8]):[c;H0;D3;+0:1](-[N;H0;D3;+0:18]2-[C:13](-[C;D1;H3:12])-[C:14]-[C:15]-[C:16]-2-[... | 40 | [{"value": 40.0, "product": "NC1=C2C(C(=CN(C2=C(C(=C1F)N1C(CCC1N)C)F)C1CC1)C(=O)O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The condensation of 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid with 5-amino-2-methyl-pyrrolidine in a similar manner as described in example 1 gave the titled product. Yield 40%, m.p 224–30° C., C18H20F2N4O3, m/z 379. (M+1)
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccc2ncccc2c1 | C1CC[NH]C1.c1ccc2ncccc2c1 | C1CC[NH]C1.c1ccc2ncccc2c1.C1CC1 | HF | null | null | null | CC1CCC(N)N1.Nc1c(F)c(F)c(F)c2c1c(=O)c(C(=O)O)cn2C1CC1>>CC1CCC(N)N1c1c(F)c(N)c2c(=O)c(C(=O)O)cn(C3CC3)c2c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ed84d5940c3742fc961e388b67925154 | CC1CNCC(C)C1.O=C(O)c1cn(-c2ccc(F)cc2F)c2cc(F)c(F)cc2c1=O>>CC1CC(C)CN(c2cc3c(cc2F)c(=O)c(C(=O)O)cn3-c2ccc(F)cc2F)C1 | FC1=C(C=CC(=C1)F)N1C=C(C(C2=CC(=C(C=C12)F)F)=O)C(=O)O.CC1CNCC(C1)C>>FC1=C(C=CC(=C1)F)N1C=C(C(C2=CC(=C(C=C12)N1CC(CC(C1)C)C)F)=O)C(=O)O | [CH3:1][CH:2]1[CH2:3][CH:4]([CH3:5])[CH2:6][NH:7][CH2:31]1.F[c:8]1[cH:12][c:11]2[c:10]([cH:9][c:13]1[F:14])[n:22](-[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][c:29]1[F:30])[cH:21][c:17]([C:18](=[O:19])[OH:20])[c:15]2=[O:16]>>[CH3:1][CH:2]1[CH2:3][CH:4]([CH3:5])[CH2:6][N:7]([c:8]2[cH:9][c:10]3[c:11]([cH:12][c:13]2[F:14])... | CC1CNCC(C)C1.O=C(O)c1cn(-c2ccc(F)cc2F)c2cc(F)c(F)cc2c1=O | CC1CC(C)CN(c2cc3c(cc2F)c(=O)c(C(=O)O)cn3-c2ccc(F)cc2F)C1 | null | null | null | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 0a145008c28f61de5d26ed53909d2d44e53648d902f27b0e2613520d626409bb | 61f3b3609ae07a421675076c7c1879296698518e31f2d1b1e7e313939214a5e5 | O=c1ccn(-c2ccccc2)c2cc(N3CCCCC3)ccc12 | F-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[c:3](:[c:4]):[c:5](:[cH;D2;+0:6]:[c;H0;D3;+0:7]:1-[F;D1;H0:8]):[#7;a:9](-[c:10]):[c:11].[C:12]-[C:13]-[NH;D2;+0:14]-[C:15]-[C:16]>>[C:12]-[C:13]-[N;H0;D3;+0:14](-[c;H0;D3;+0:1]1:[cH;D2;+0:6]:[c:5](:[#7;a:9](-[c:10]):[c:11]):[c:3](:[c:4]):[cH;D2;+0:2]:[c;H0;D3;+0:7]:1-[F;D1;H0:8])-[C:15]-... | 43 | [{"value": 43.0, "product": "FC1=C(C=CC(=C1)F)N1C=C(C(C2=CC(=C(C=C12)N1CC(CC(C1)C)C)F)=O)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The condensation of with 1-(2′,4′-difluorophenyl)-6,7-difluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid with 3,5-dimethylpiperidine in a similar manner as described in example 1 gave the titled product. Yield 43%, m.p 224–26° C., C23H21F3N2O3, m/z 431. (M+1)
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Secondary amine | Aromatic halide.Tertiary amine | C1CCNCC1.c1ccc2ncccc2c1 | C1CC[NH]CC1.c1ccc2ncccc2c1 | C1CC[NH]CC1.c1ccc2ncccc2c1.c1ccccc1 | HF | null | null | null | CC1CNCC(C)C1.O=C(O)c1cn(-c2ccc(F)cc2F)c2cc(F)c(F)cc2c1=O>>CC1CC(C)CN(c2cc3c(cc2F)c(=O)c(C(=O)O)cn3-c2ccc(F)cc2F)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8eceacde241b40df8f1b4079320c969f | CC1CC(O)CN1.Nc1c(F)c(F)c(F)c2c1c(=O)c(C(=O)O)cn2-c1ccc(F)cc1F>>CC1CC(O)CN1c1c(F)c(N)c2c(=O)c(C(=O)O)cn(-c3ccc(F)cc3F)c2c1F | NC1=C2C(C(=CN(C2=C(C(=C1F)F)F)C1=C(C=C(C=C1)F)F)C(=O)O)=O.OC1CNC(C1)C>>NC1=C2C(C(=CN(C2=C(C(=C1F)N1CC(CC1C)O)F)C1=C(C=C(C=C1)F)F)C(=O)O)=O | [CH3:1][CH:2]1[CH2:3][CH:4]([OH:5])[CH2:6][NH:7]1.F[c:8]1[c:9]([F:10])[c:11]([NH2:12])[c:13]2[c:14](=[O:15])[c:16]([C:17](=[O:18])[OH:19])[cH:20][n:21](-[c:22]3[cH:23][cH:24][c:25]([F:26])[cH:27][c:28]3[F:29])[c:30]2[c:31]1[F:32]>>[CH3:1][CH:2]1[CH2:3][CH:4]([OH:5])[CH2:6][N:7]1[c:8]1[c:9]([F:10])[c:11]([NH2:12])[c:13]... | CC1CC(O)CN1.Nc1c(F)c(F)c(F)c2c1c(=O)c(C(=O)O)cn2-c1ccc(F)cc1F | CC1CC(O)CN1c1c(F)c(N)c2c(=O)c(C(=O)O)cn(-c3ccc(F)cc3F)c2c1F | null | null | null | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 89f800d0b5c6eace023ec0f16ed65844f5dd409e156b3b4845e1db5de9a38872 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1ccn(-c2ccccc2)c2cc(N3CCCC3)ccc12 | F-[c;H0;D3;+0:1]1:[c:2](-[F;D1;H0:3]):[c:4](:[c:5]:[c:6]:[c:7]:1-[F;D1;H0:8]):[#7;a:9](-[c:10]):[c:11].[C;D1;H3:12]-[C:13]1-[C:14]-[C:15]-[C:16]-[NH;D2;+0:17]-1>>[C;D1;H3:12]-[C:13]1-[C:14]-[C:15]-[C:16]-[N;H0;D3;+0:17]-1-[c;H0;D3;+0:1]1:[c:2](-[F;D1;H0:3]):[c:4](:[c:5]:[c:6]:[c:7]:1-[F;D1;H0:8]):[#7;a:9](-[c:10]):[c:1... | 64 | [{"value": 64.0, "product": "NC1=C2C(C(=CN(C2=C(C(=C1F)N1CC(CC1C)O)F)C1=C(C=C(C=C1)F)F)C(=O)O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The condensation of 5-Amino-1-(2′,4′-difluorophenyl)-6,7,8-trifluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid with 3-hydroxy-5-methylpyrrolidine in a similar manner as described in example 1 gave the titled product. Yield 64%, m.p ° C., C21H17F4N3O4, m/z 453. (M+1)
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccc2ncccc2c1 | C1CC[NH]C1.c1ccc2ncccc2c1 | C1CC[NH]C1.c1ccc2ncccc2c1.c1ccccc1 | HF | null | null | null | CC1CC(O)CN1.Nc1c(F)c(F)c(F)c2c1c(=O)c(C(=O)O)cn2-c1ccc(F)cc1F>>CC1CC(O)CN1c1c(F)c(N)c2c(=O)c(C(=O)O)cn(-c3ccc(F)cc3F)c2c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-27aa6f8b4825442e9c6c524f48c6d1d4 | CC#N.CCOC(=O)c1cn(-c2ccc(F)cc2F)c2nc(F)c(F)cc2c1=O>>O=C(O)c1cn(-c2ccc(F)cc2F)c2nc(NC3CCNCC3)c(F)cc2c1=O | FC1=C(C=CC(=C1)F)N1C=C(C(C2=CC(=C(N=C12)F)F)=O)C(=O)OCC.C(C)#N>>FC1=C(C=CC(=C1)F)N1C=C(C(C2=CC(=C(N=C12)NC1CCNCC1)F)=O)C(=O)O | [N:18]#[C:19][CH3:20].F[c:17]1[n:16][c:15]2[n:6](-[c:7]3[cH:8][cH:9][c:10]([F:11])[cH:12][c:13]3[F:14])[cH:5][c:4]([C:2](=[O:1])[O:3][CH2:21][CH3:24])[c:29](=[O:30])[c:28]2[cH:27][c:25]1[F:26]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][n:6](-[c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][c:13]2[F:14])[c:15]2[n:16][c:17]([NH:18][CH:19]3... | CC#N.CCOC(=O)c1cn(-c2ccc(F)cc2F)c2nc(F)c(F)cc2c1=O | O=C(O)c1cn(-c2ccc(F)cc2F)c2nc(NC3CCNCC3)c(F)cc2c1=O | null | null | null | Functional Group Interconversion | OtherReaction | 9018b79a4eb49d54ba4d5db64ba19898e60817b466d1738722c380fff7e30c6e | 27d97b496782606608db497ffbbfcf9a38507dd7b0eec121da749d5de9518495 | O=c1ccn(-c2ccccc2)c2nc(NC3CCNCC3)ccc12 | F-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]-[C:7](=[O;D1;H0:8])-[O;H0;D2;+0:9]-[CH2;D2;+0:10]-[CH3;D1;+0:11]):[c:12](-[F;D1;H0:13]):[c:14].[CH3;D1;+0:15]-[C;H0;D2;+0:16]#[N;H0;D1;+0:17]>>[F;D1;H0:13]-[c:12](:[c:14]):[c;H0;D3;+0:1](-[NH;D2;+0:17]-[CH;D3;+0:16]1-[CH2;D2;+0:15]-[CH2;D2;+0:10]-[#7:18]-[C:19]-[CH2... | 74 | [{"value": 74.0, "product": "FC1=C(C=CC(=C1)F)N1C=C(C(C2=CC(=C(N=C12)NC1CCNCC1)F)=O)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Ethyl 1-(2,4-difluorophenyl)-6,7-difluoro-1,4-dihydro-4-oxo-naphthyridine-3-carboxylate (0.5 g, 1.3 mmole) and (3-N-ethoxycarbonyl)aminopyrrolidine (0.3 g, 1.74 mmole) in acetonitril (5 ml) was stirred at 80° C. for 3 hr and cooled. Solvent was concentrated to dryness and 5% aqueous NaOH (10 ml) was added to reaction m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Nitrile | Carboxylic acid.Secondary amine.Secondary amine | c1cnc2ncccc2c1 | c1cnc2ncccc2c1.C1CCNCC1 | c1ccccc1.c1cnc2ncccc2c1.C1CCNCC1 | null | null | null | 2 | CC#N.CCOC(=O)c1cn(-c2ccc(F)cc2F)c2nc(F)c(F)cc2c1=O>>O=C(O)c1cn(-c2ccc(F)cc2F)c2nc(NC3CCNCC3)c(F)cc2c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a04fa00654814628b99f27e75b65df65 | CC1CNCCC1N.COc1c(F)c(F)c(N)c2c(=O)c(C(=O)O)cn(C3CC3)c12>>COc1c(N2CCC(N)C(C)C2)c(F)c(N)c2c(=O)c(C(=O)O)cn(C3CC3)c12 | NC1=C2C(C(=CN(C2=C(C(=C1F)F)OC)C1CC1)C(=O)O)=O.NC1C(CNCC1)C>>NC1=C2C(C(=CN(C2=C(C(=C1F)N1CC(C(CC1)N)C)OC)C1CC1)C(=O)O)=O | [NH:5]1[CH2:6][CH2:7][CH:8]([NH2:9])[CH:10]([CH3:11])[CH2:12]1.F[c:4]1[c:3]([O:2][CH3:1])[c:29]2[c:17]([c:15]([NH2:16])[c:13]1[F:14])[c:18](=[O:19])[c:20]([C:21](=[O:22])[OH:23])[cH:24][n:25]2[CH:26]1[CH2:27][CH2:28]1>>[CH3:1][O:2][c:3]1[c:4]([N:5]2[CH2:6][CH2:7][CH:8]([NH2:9])[CH:10]([CH3:11])[CH2:12]2)[c:13]([F:14])[... | CC1CNCCC1N.COc1c(F)c(F)c(N)c2c(=O)c(C(=O)O)cn(C3CC3)c12 | COc1c(N2CCC(N)C(C)C2)c(F)c(N)c2c(=O)c(C(=O)O)cn(C3CC3)c12 | null | null | null | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 6ca896bdf5cf17e98a9402041cc62e117ebb3e6ff582ec413fbc5219ab9874c5 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1ccn(C2CC2)c2cc(N3CCCCC3)ccc12 | F-[c;H0;D3;+0:1]1:[c:2](-[F;D1;H0:3]):[c:4]:[c:5]:[c:6](:[#7;a:7](-[C:8]):[c:9]):[c:10]:1-[#8:11].[C:12]-[C:13]-[NH;D2;+0:14]-[C:15]-[C:16]>>[#8:11]-[c:10]1:[c:6](:[c:5]:[c:4]:[c:2](-[F;D1;H0:3]):[c;H0;D3;+0:1]:1-[N;H0;D3;+0:14](-[C:13]-[C:12])-[C:15]-[C:16]):[#7;a:7](-[C:8]):[c:9] | 50 | [{"value": 50.0, "product": "NC1=C2C(C(=CN(C2=C(C(=C1F)N1CC(C(CC1)N)C)OC)C1CC1)C(=O)O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The condensation of 5-amino-1-cyclopropyl-6,7-difluoro-8-methoxy -1,4-dihydro-4-oxo-quinoline-3-carboxylic acid with 4-amino-3-methylpiperidine was carried out in a similar manner as described in example 1, gave the titled product. Yield 50%, m.p 260–62° C., C20H25FN4O4, m/z 405 (M+1).
Conditions: See reaction.notes.pr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNCC1.c1ccc2ncccc2c1 | C1CC[NH]CC1.c1ccc2ncccc2c1 | C1CC[NH]CC1.c1ccc2ncccc2c1.C1CC1 | HF | null | null | null | CC1CNCCC1N.COc1c(F)c(F)c(N)c2c(=O)c(C(=O)O)cn(C3CC3)c12>>COc1c(N2CCC(N)C(C)C2)c(F)c(N)c2c(=O)c(C(=O)O)cn(C3CC3)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-76d3fc7e5e284b0d87498917e0b85970 | Cc1c(F)c(F)c(F)c2c1c(=O)c(C(=O)O)cn2C1CC1.NCC1CNCCC1O>>Cc1c(F)c(N2CCC(O)C(CN)C2)c(F)c2c1c(=O)c(C(=O)O)cn2C1CC1 | C1(CC1)N1C=C(C(C2=C(C(=C(C(=C12)F)F)F)C)=O)C(=O)O.NCC1CNCCC1O>>C1(CC1)N1C=C(C(C2=C(C(=C(C(=C12)F)N1CC(C(CC1)O)CN)F)C)=O)C(=O)O | F[c:5]1[c:3]([F:4])[c:2]([CH3:1])[c:18]2[c:17]([c:15]1[F:16])[n:26]([CH:27]1[CH2:28][CH2:29]1)[cH:25][c:21]([C:22](=[O:23])[OH:24])[c:19]2=[O:20].[NH:6]1[CH2:7][CH2:8][CH:9]([OH:10])[CH:11]([CH2:12][NH2:13])[CH2:14]1>>[CH3:1][c:2]1[c:3]([F:4])[c:5]([N:6]2[CH2:7][CH2:8][CH:9]([OH:10])[CH:11]([CH2:12][NH2:13])[CH2:14]2)[... | Cc1c(F)c(F)c(F)c2c1c(=O)c(C(=O)O)cn2C1CC1.NCC1CNCCC1O | Cc1c(F)c(N2CCC(O)C(CN)C2)c(F)c2c1c(=O)c(C(=O)O)cn2C1CC1 | null | null | null | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 6ca896bdf5cf17e98a9402041cc62e117ebb3e6ff582ec413fbc5219ab9874c5 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1ccn(C2CC2)c2cc(N3CCCCC3)ccc12 | F-[c;H0;D3;+0:1]1:[c:2](-[F;D1;H0:3]):[c:4](:[c:5]:[c:6]:[c:7]:1-[F;D1;H0:8]):[#7;a:9](-[C:10]):[c:11].[C:12]-[C:13]-[NH;D2;+0:14]-[C:15]-[C:16]>>[C:12]-[C:13]-[N;H0;D3;+0:14](-[c;H0;D3;+0:1]1:[c:2](-[F;D1;H0:3]):[c:4](:[c:5]:[c:6]:[c:7]:1-[F;D1;H0:8]):[#7;a:9](-[C:10]):[c:11])-[C:15]-[C:16] | 45.9 | [{"value": 45.9, "product": "C1(CC1)N1C=C(C(C2=C(C(=C(C(=C12)F)N1CC(C(CC1)O)CN)F)C)=O)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The condensation of 1-cyclopropyl-6,7,8-trifluoro-5-methyl-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid with 3-aminomethyl-4-hydroxy-piperidine was carried out in a similar manner as described in example 1 gave the titled product. Yield 45.9%, m.p 270–75° C., C20H23F2N3O4, m/z 408 (M+1).
Conditions: See reaction.notes... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2ncccc2c1.C1CCNCC1 | C1CC[NH]CC1.c1ccc2ncccc2c1 | C1CC[NH]CC1.c1ccc2ncccc2c1.C1CC1 | HF | null | null | null | Cc1c(F)c(F)c(F)c2c1c(=O)c(C(=O)O)cn2C1CC1.NCC1CNCCC1O>>Cc1c(F)c(N2CCC(O)C(CN)C2)c(F)c2c1c(=O)c(C(=O)O)cn2C1CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-db8fe1955bfb44b1ad634f8887301c0b | NCC1CNCCC1O.Nc1c(F)c(F)c(F)c2c1c(=O)c(C(=O)O)cn2C1CC1>>NCC1CN(c2c(F)c(N)c3c(=O)c(C(=O)O)cn(C4CC4)c3c2F)CCC1O | NC1=C2C(C(=CN(C2=C(C(=C1F)F)F)C1CC1)C(=O)O)=O.NCC1CNCCC1O>>NC1=C2C(C(=CN(C2=C(C(=C1F)N1CC(C(CC1)O)CN)F)C1CC1)C(=O)O)=O | [NH2:1][CH2:2][CH:3]1[CH2:4][NH:5][CH2:26][CH2:27][CH:28]1[OH:29].F[c:6]1[c:7]([F:8])[c:9]([NH2:10])[c:11]2[c:12](=[O:13])[c:14]([C:15](=[O:16])[OH:17])[cH:18][n:19]([CH:20]3[CH2:21][CH2:22]3)[c:23]2[c:24]1[F:25]>>[NH2:1][CH2:2][CH:3]1[CH2:4][N:5]([c:6]2[c:7]([F:8])[c:9]([NH2:10])[c:11]3[c:12](=[O:13])[c:14]([C:15](=[O... | NCC1CNCCC1O.Nc1c(F)c(F)c(F)c2c1c(=O)c(C(=O)O)cn2C1CC1 | NCC1CN(c2c(F)c(N)c3c(=O)c(C(=O)O)cn(C4CC4)c3c2F)CCC1O | null | null | null | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 6ca896bdf5cf17e98a9402041cc62e117ebb3e6ff582ec413fbc5219ab9874c5 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1ccn(C2CC2)c2cc(N3CCCCC3)ccc12 | F-[c;H0;D3;+0:1]1:[c:2](-[F;D1;H0:3]):[c:4](:[c:5]:[c:6]:[c:7]:1-[F;D1;H0:8]):[#7;a:9](-[C:10]):[c:11].[C:12]-[C:13]-[NH;D2;+0:14]-[C:15]-[C:16]>>[C:10]-[#7;a:9](:[c:11]):[c:4]1:[c:5]:[c:6]:[c:7](-[F;D1;H0:8]):[c;H0;D3;+0:1](-[N;H0;D3;+0:14](-[C:13]-[C:12])-[C:15]-[C:16]):[c:2]:1-[F;D1;H0:3] | 52.8 | [{"value": 52.8, "product": "NC1=C2C(C(=CN(C2=C(C(=C1F)N1CC(C(CC1)O)CN)F)C1CC1)C(=O)O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The condensation of 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid with 3-aminomethyl-4-hydroxy-piperidine was carried out in a similar manner as described in example 1, gave the titled product. Yield 52.8%, m.p 202–04° C., C19H22F2N4O4, m/z 409 (M+1).
Conditions: See reaction.notes... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNCC1.c1ccc2ncccc2c1 | C1CC[NH]CC1.c1ccc2ncccc2c1 | C1CC[NH]CC1.c1ccc2ncccc2c1.C1CC1 | HF | null | null | null | NCC1CNCCC1O.Nc1c(F)c(F)c(F)c2c1c(=O)c(C(=O)O)cn2C1CC1>>NCC1CN(c2c(F)c(N)c3c(=O)c(C(=O)O)cn(C4CC4)c3c2F)CCC1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f878f40338784547baf46f135f7a5b94 | CCN1CCNCC1C.O=C(O)c1cn(C2CC2)c2cc(F)c(F)cc2c1=O>>CCN1CCN(c2cc3c(cc2F)c(=O)c(C(=O)O)cn3C2CC2)CC1C | C1(CC1)N1C=C(C(C2=CC(=C(C=C12)F)F)=O)C(=O)O.C(C)N1C(CNCC1)C>>C1(CC1)N1C=C(C(C2=CC(=C(C=C12)N1CC(N(CC1)CC)C)F)=O)C(=O)O | [CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][NH:6][CH2:25][CH:26]1[CH3:27].F[c:7]1[cH:11][c:10]2[c:9]([cH:8][c:12]1[F:13])[n:21]([CH:22]1[CH2:23][CH2:24]1)[cH:20][c:16]([C:17](=[O:18])[OH:19])[c:14]2=[O:15]>>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][N:6]([c:7]2[cH:8][c:9]3[c:10]([cH:11][c:12]2[F:13])[c:14](=[O:15])[c:16]([C:17](=[O:18]... | CCN1CCNCC1C.O=C(O)c1cn(C2CC2)c2cc(F)c(F)cc2c1=O | CCN1CCN(c2cc3c(cc2F)c(=O)c(C(=O)O)cn3C2CC2)CC1C | null | null | null | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 2bf29d7699c5e6ac49cf7aa5e7979b7104c7297e82c35575df54ba08e9cd87a6 | 61f3b3609ae07a421675076c7c1879296698518e31f2d1b1e7e313939214a5e5 | O=c1ccn(C2CC2)c2cc(N3CCNCC3)ccc12 | F-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[c:3](:[c:4]):[c:5](:[cH;D2;+0:6]:[c;H0;D3;+0:7]:1-[F;D1;H0:8]):[#7;a:9](-[C:10]):[c:11].[#7:12]1-[C:13]-[C:14]-[NH;D2;+0:15]-[C:16]-[C:17]-1>>[C:10]-[#7;a:9](:[c:11]):[c:5]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[N;H0;D3;+0:15]2-[C:14]-[C:13]-[#7:12]-[C:17]-[C:16]-2):[c;H0;D3;+0:7](-[F;D1;H0:8]):... | 51 | [{"value": 51.0, "product": "C1(CC1)N1C=C(C(C2=CC(=C(C=C12)N1CC(N(CC1)CC)C)F)=O)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The condensation of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid with 4-ethyl-3-methylpiperazine was carried out in a similar manner as described in example 1 gave the titled product. Yield 51%, m.p 200° C., C20H24FN3O3, m/z 374 (M+1).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Secondary amine | Aromatic halide.Tertiary amine | C1C[NH]CCN1.c1ccc2ncccc2c1 | C1C[NH]CC[NH]1.c1ccc2ncccc2c1 | C1C[NH]CC[NH]1.c1ccc2ncccc2c1.C1CC1 | HF | null | null | null | CCN1CCNCC1C.O=C(O)c1cn(C2CC2)c2cc(F)c(F)cc2c1=O>>CCN1CCN(c2cc3c(cc2F)c(=O)c(C(=O)O)cn3C2CC2)CC1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2af2703dc9ba43b79b688e6cb3a1f84c | NC1CCNC1.Nc1c(F)c(F)c(F)c2c1c(=O)c(C(=O)O)cn2-c1ccc(F)cc1F>>Nc1c(F)c(N2CCC(N)C2)c(F)c2c1c(=O)c(C(=O)O)cn2-c1ccc(F)cc1F | NC1=C2C(C(=CN(C2=C(C(=C1F)F)F)C1=C(C=C(C=C1)F)F)C(=O)O)=O.NC1CNCC1>>NC1=C2C(C(=CN(C2=C(C(=C1F)N1CC(CC1)N)F)C1=C(C=C(C=C1)F)F)C(=O)O)=O | [NH:6]1[CH2:7][CH2:8][CH:9]([NH2:10])[CH2:11]1.F[c:5]1[c:3]([F:4])[c:2]([NH2:1])[c:15]2[c:14]([c:12]1[F:13])[n:23](-[c:24]1[cH:25][cH:26][c:27]([F:28])[cH:29][c:30]1[F:31])[cH:22][c:18]([C:19](=[O:20])[OH:21])[c:16]2=[O:17]>>[NH2:1][c:2]1[c:3]([F:4])[c:5]([N:6]2[CH2:7][CH2:8][CH:9]([NH2:10])[CH2:11]2)[c:12]([F:13])[c:1... | NC1CCNC1.Nc1c(F)c(F)c(F)c2c1c(=O)c(C(=O)O)cn2-c1ccc(F)cc1F | Nc1c(F)c(N2CCC(N)C2)c(F)c2c1c(=O)c(C(=O)O)cn2-c1ccc(F)cc1F | null | null | null | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 89f800d0b5c6eace023ec0f16ed65844f5dd409e156b3b4845e1db5de9a38872 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1ccn(-c2ccccc2)c2cc(N3CCCC3)ccc12 | F-[c;H0;D3;+0:1]1:[c:2](-[F;D1;H0:3]):[c:4](:[c:5]:[c:6]:[c:7]:1-[F;D1;H0:8]):[#7;a:9](-[c:10]):[c:11].[C:12]1-[C:13]-[C:14]-[C:15]-[NH;D2;+0:16]-1>>[F;D1;H0:3]-[c:2]1:[c:4](:[c:5]:[c:6]:[c:7](-[F;D1;H0:8]):[c;H0;D3;+0:1]:1-[N;H0;D3;+0:16]1-[C:12]-[C:13]-[C:14]-[C:15]-1):[#7;a:9](-[c:10]):[c:11] | 71 | [{"value": 71.0, "product": "NC1=C2C(C(=CN(C2=C(C(=C1F)N1CC(CC1)N)F)C1=C(C=C(C=C1)F)F)C(=O)O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The condensation of 5-amino-1-(2′,4′-difluorophenyl)-6,7,8-trifluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid with 3-aminopyrrolidine was carried out in a similar manner as described in example 1, gave the titled product. Yield 71%, m.p 268° C. (d), C20H16F4N4O3, m/z 437 (M+1).
Conditions: See reaction.notes.proce... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccc2ncccc2c1 | C1CC[NH]C1.c1ccc2ncccc2c1 | C1CC[NH]C1.c1ccc2ncccc2c1.c1ccccc1 | HF | null | null | null | NC1CCNC1.Nc1c(F)c(F)c(F)c2c1c(=O)c(C(=O)O)cn2-c1ccc(F)cc1F>>Nc1c(F)c(N2CCC(N)C2)c(F)c2c1c(=O)c(C(=O)O)cn2-c1ccc(F)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7048ad1dcc504833a6fca74d13f1cf65 | CCC1CNCCC1N.O=C(O)c1cn(C2CC2)c2nc(F)c(F)cc2c1=O>>CCC1CN(c2nc3c(cc2F)c(=O)c(C(=O)O)cn3C2CC2)CCC1N | C1(CC1)N1C=C(C(C2=CC(=C(N=C12)F)F)=O)C(=O)O.NC1C(CNCC1)CC>>C1(CC1)N1C=C(C(C2=CC(=C(N=C12)N1CC(C(CC1)N)CC)F)=O)C(=O)O | [CH3:1][CH2:2][CH:3]1[CH2:4][NH:5][CH2:24][CH2:25][CH:26]1[NH2:27].F[c:6]1[n:7][c:8]2[c:9]([cH:10][c:11]1[F:12])[c:13](=[O:14])[c:15]([C:16](=[O:17])[OH:18])[cH:19][n:20]2[CH:21]1[CH2:22][CH2:23]1>>[CH3:1][CH2:2][CH:3]1[CH2:4][N:5]([c:6]2[n:7][c:8]3[c:9]([cH:10][c:11]2[F:12])[c:13](=[O:14])[c:15]([C:16](=[O:17])[OH:18]... | CCC1CNCCC1N.O=C(O)c1cn(C2CC2)c2nc(F)c(F)cc2c1=O | CCC1CN(c2nc3c(cc2F)c(=O)c(C(=O)O)cn3C2CC2)CCC1N | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 3447f48483ec06bf5882e45795836276c213a26384c545bb587d4538d103f0c6 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1ccn(C2CC2)c2nc(N3CCCCC3)ccc12 | F-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]:[#7;a:4]):[c:5](-[F;D1;H0:6]):[c:7].[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]>>[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:10](-[C:9]-[C:8])-[C:11]-[C:12]):[c:5](-[F;D1;H0:6]):[c:7] | 71 | [{"value": 71.0, "product": "C1(CC1)N1C=C(C(C2=CC(=C(N=C12)N1CC(C(CC1)N)CC)F)=O)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The condensation of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-naphthyridine-3-carboxylic acid with 4-amino-3-ethylpiperidine was carried out in acetonitrile in a similar manner as described in example 1, gave the titled product. Yield 71%, m.p 218–20° C., C19H23FN4O3, m/z 375 (M+1).
Conditions: See reaction.notes.pr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNCC1.c1cnc2ncccc2c1 | C1CC[NH]CC1.c1cnc2ncccc2c1 | C1CC[NH]CC1.c1cnc2ncccc2c1.C1CC1 | HF | C(C)#N | null | null | CCC1CNCCC1N.O=C(O)c1cn(C2CC2)c2nc(F)c(F)cc2c1=O>C(C)#N>CCC1CN(c2nc3c(cc2F)c(=O)c(C(=O)O)cn3C2CC2)CCC1N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9e02f934b01a4fad9459c6326aaa2d90 | CNC1CCNCC1(C)C.COc1c(F)c(F)c(N)c2c(=O)c(C(=O)O)cn(C3CC3)c12>>CNC1CCN(c2c(F)c(N)c3c(=O)c(C(=O)O)cn(C4CC4)c3c2OC)CC1(C)C | NC1=C2C(C(=CN(C2=C(C(=C1F)F)OC)C1CC1)C(=O)O)=O.CNC1C(CNCC1)(C)C>>NC1=C2C(C(=CN(C2=C(C(=C1F)N1CC(C(CC1)NC)(C)C)OC)C1CC1)C(=O)O)=O | [CH3:1][NH:2][CH:3]1[CH2:4][CH2:5][NH:6][CH2:28][C:29]1([CH3:30])[CH3:31].F[c:7]1[c:8]([F:9])[c:10]([NH2:11])[c:12]2[c:13](=[O:14])[c:15]([C:16](=[O:17])[OH:18])[cH:19][n:20]([CH:21]3[CH2:22][CH2:23]3)[c:24]2[c:25]1[O:26][CH3:27]>>[CH3:1][NH:2][CH:3]1[CH2:4][CH2:5][N:6]([c:7]2[c:8]([F:9])[c:10]([NH2:11])[c:12]3[c:13](=... | CNC1CCNCC1(C)C.COc1c(F)c(F)c(N)c2c(=O)c(C(=O)O)cn(C3CC3)c12 | CNC1CCN(c2c(F)c(N)c3c(=O)c(C(=O)O)cn(C4CC4)c3c2OC)CC1(C)C | null | null | null | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 6ca896bdf5cf17e98a9402041cc62e117ebb3e6ff582ec413fbc5219ab9874c5 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1ccn(C2CC2)c2cc(N3CCCCC3)ccc12 | F-[c;H0;D3;+0:1]1:[c:2](-[#8:3]):[c:4](:[c:5]:[c:6]:[c:7]:1-[F;D1;H0:8]):[#7;a:9](-[C:10]):[c:11].[C:12]-[C:13]-[NH;D2;+0:14]-[C:15]-[C:16]>>[#8:3]-[c:2]1:[c:4](:[c:5]:[c:6]:[c:7](-[F;D1;H0:8]):[c;H0;D3;+0:1]:1-[N;H0;D3;+0:14](-[C:13]-[C:12])-[C:15]-[C:16]):[#7;a:9](-[C:10]):[c:11] | 54 | [{"value": 54.0, "product": "NC1=C2C(C(=CN(C2=C(C(=C1F)N1CC(C(CC1)NC)(C)C)OC)C1CC1)C(=O)O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The condensation of 5-amino-1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid with 4-methylamino-3,3-dimethylpiperidine was carried out in a similar manner as described in example 1 (NorA), gave the titled product. Yield 54%, m.p 250° C., C22H29FN4O4, m/z 433 (M+1).
Conditions: See reac... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNCC1.c1ccc2ncccc2c1 | C1CC[NH]CC1.c1ccc2ncccc2c1 | C1CC[NH]CC1.c1ccc2ncccc2c1.C1CC1 | HF | null | null | null | CNC1CCNCC1(C)C.COc1c(F)c(F)c(N)c2c(=O)c(C(=O)O)cn(C3CC3)c12>>CNC1CCN(c2c(F)c(N)c3c(=O)c(C(=O)O)cn(C4CC4)c3c2OC)CC1(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a1b74487e4a6436087218ffd783f010b | COc1c(N2CCC(NC(=O)OC(C)(C)C)C(C)(C)C2)c(F)cc2c(=O)c(C(=O)O)cn(C3CC3)c12>>COc1c(N2CCC(N)C(C)(C)C2)c(F)cc2c(=O)c(C(=O)OC(C)C)cn(C3CC3)c12 | C1(CC1)N1C=C(C(C2=CC(=C(C(=C12)OC)N1CC(C(CC1)NC(=O)OC(C)(C)C)(C)C)F)=O)C(=O)O.C(=O)([O-])[O-].[K+].[K+].ICCC>>C1(CC1)N1C=C(C(C2=CC(=C(C(=C12)OC)N1CC(C(CC1)N)(C)C)F)=O)C(=O)OC(C)C | C[C:24](OC(=O)[NH:9][CH:8]1[CH2:7][CH2:6][N:5]([c:4]2[c:3]([O:2][CH3:1])[c:32]3[c:17]([cH:16][c:14]2[F:15])[c:18](=[O:19])[c:20]([C:21](=[O:22])[OH:23])[cH:27][n:28]3[CH:29]2[CH2:30][CH2:31]2)[CH2:13][C:10]1([CH3:11])[CH3:12])([CH3:25])[CH3:26]>>[CH3:1][O:2][c:3]1[c:4]([N:5]2[CH2:6][CH2:7][CH:8]([NH2:9])[C:10]([CH3:11]... | COc1c(N2CCC(NC(=O)OC(C)(C)C)C(C)(C)C2)c(F)cc2c(=O)c(C(=O)O)cn(C3CC3)c12 | COc1c(N2CCC(N)C(C)(C)C2)c(F)cc2c(=O)c(C(=O)OC(C)C)cn(C3CC3)c12 | null | null | null | Miscellaneous | OtherReaction | 7808bb99be630acdad65a861102ab89d3cfe5057444293e2c0619a45c7cac95d | a982aaac60b2789e2bafd29803ed2303422f9e2a84dbea210fa11abe5a6bb059 | O=c1ccn(C2CC2)c2cc(N3CCCCC3)ccc12 | C-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-O-C(=O)-[NH;D2;+0:4]-[C:5](-[C:6])-[C:7].[#7;a:8]:[c:9]:[c:10]-[C:11](=[O;D1;H0:12])-[OH;D1;+0:13]>>[#7;a:8]:[c:9]:[c:10]-[C:11](=[O;D1;H0:12])-[O;H0;D2;+0:13]-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[C:6]-[C:5](-[NH2;D1;+0:4])-[C:7] | 45 | [{"value": 45.0, "product": "C1(CC1)N1C=C(C(C2=CC(=C(C(=C12)OC)N1CC(C(CC1)N)(C)C)F)=O)C(=O)OC(C)C", "details": "PERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 7 | HOUR | In a dry dimethylformaide (15 ml) was taken a mixture of 1-cyclopropyl-6-fluoro-8-methoxy-1,4-dihydro-7-(4′-t-butoxycarbonylamino-3′,3′-dimethylpiperidin-1-yl)-4-oxo-quinoline-3-carboxylic acid (1 g, 1.98 mmole), K2CO3 (0.275 g, 1.98 mmole) was stirred at 70° C. for 7 hr. Added 1-iodopropane (0.5 g, 2.98 mmole) to reac... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Boc | Ester.Primary amine | null | null | C1CC[NH]CC1.c1ccc2ncccc2c1.C1CC1 | HO- | null | 70 | 7 | COc1c(N2CCC(NC(=O)OC(C)(C)C)C(C)(C)C2)c(F)cc2c(=O)c(C(=O)O)cn(C3CC3)c12>>COc1c(N2CCC(N)C(C)(C)C2)c(F)cc2c(=O)c(C(=O)OC(C)C)cn(C3CC3)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3157bbbc971143d2a53b3dc4daf97f21 | COc1c(N2CCC(NC(=O)[C@H](C)NC(=O)OC(C)(C)C)C(C)(C)C2)c(F)cc2c(=O)c(C(=O)O)cn(C3CC3)c12>>COc1c(N2CCC(NC(=O)[C@H](C)N)C(C)(C)C2)c(F)cc2c(=O)c(C(=O)O)cn(C3CC3)c12 | C1(CC1)N1C=C(C(C2=CC(=C(C(=C12)OC)N1CC(C(CC1)NC([C@@H](NC(=O)OC(C)(C)C)C)=O)(C)C)F)=O)C(=O)O.Cl>>Cl.C1(CC1)N1C=C(C(C2=CC(=C(C(=C12)OC)N1CC(C(CC1)NC([C@@H](N)C)=O)(C)C)F)=O)C(=O)O | CC(C)(C)OC(=O)[NH:14][C@H:12]([C:10]([NH:9][CH:8]1[CH2:7][CH2:6][N:5]([c:4]2[c:3]([O:2][CH3:1])[c:34]3[c:22]([cH:21][c:19]2[F:20])[c:23](=[O:24])[c:25]([C:26](=[O:27])[OH:28])[cH:29][n:30]3[CH:31]2[CH2:32][CH2:33]2)[CH2:18][C:15]1([CH3:16])[CH3:17])=[O:11])[CH3:13]>>[CH3:1][O:2][c:3]1[c:4]([N:5]2[CH2:6][CH2:7][CH:8]([N... | COc1c(N2CCC(NC(=O)[C@H](C)NC(=O)OC(C)(C)C)C(C)(C)C2)c(F)cc2c(=O)c(C(=O)O)cn(C3CC3)c12 | COc1c(N2CCC(NC(=O)[C@H](C)N)C(C)(C)C2)c(F)cc2c(=O)c(C(=O)O)cn(C3CC3)c12 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=c1ccn(C2CC2)c2cc(N3CCCCC3)ccc12 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C;D1;H3:3])-[C:4](=[O;D1;H0:5])-[#7:6]-[C:7]>>[C:7]-[#7:6]-[C:4](=[O;D1;H0:5])-[C:2](-[C;D1;H3:3])-[NH2;D1;+0:1] | 75 | [{"value": 75.0, "product": "Cl.C1(CC1)N1C=C(C(C2=CC(=C(C(=C12)OC)N1CC(C(CC1)NC([C@@H](N)C)=O)(C)C)F)=O)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-Cyclopropyl-6-fluoro-8-methoxy-1,4-dihydro-7-{4′-(N-t-butoxycarbonyl-L-alanyl)amino-3′,3′-dimethylpiperidin-1-yl}-4-oxo-quinoline-3-carboxylic acid (0.9 gm) is hydrolysed with 6N HCl (20 ml) at room temperature for 1 hr. The mixture concentrated to furnish the titled product. Yield 75%, m.p 245–50° C., C24H31FN4O5.HC... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | C1CC[NH]CC1.c1ccc2ncccc2c1.C1CC1 | HO- | null | null | null | COc1c(N2CCC(NC(=O)[C@H](C)NC(=O)OC(C)(C)C)C(C)(C)C2)c(F)cc2c(=O)c(C(=O)O)cn(C3CC3)c12>>COc1c(N2CCC(NC(=O)[C@H](C)N)C(C)(C)C2)c(F)cc2c(=O)c(C(=O)O)cn(C3CC3)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-71b22db518414164b5aaf59d12355f9e | COc1c(N2CCC(NC(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)C)C(C)(C)C2)c(F)cc2c(=O)c(C(=O)O)cn(C3CC3)c12>>COc1c(N2CCC(NC(=O)[C@@H](N)C(C)C)C(C)(C)C2)c(F)cc2c(=O)c(C(=O)O)cn(C3CC3)c12 | C1(CC1)N1C=C(C(C2=CC(=C(C(=C12)OC)N1CC(C(CC1)NC([C@@H](NC(=O)OC(C)(C)C)C(C)C)=O)(C)C)F)=O)C(=O)O.Cl>>Cl.C1(CC1)N1C=C(C(C2=CC(=C(C(=C12)OC)N1CC(C(CC1)NC([C@@H](N)C(C)C)=O)(C)C)F)=O)C(=O)O | CC(C)(C)OC(=O)[NH:13][C@H:12]([C:10]([NH:9][CH:8]1[CH2:7][CH2:6][N:5]([c:4]2[c:3]([O:2][CH3:1])[c:36]3[c:24]([cH:23][c:21]2[F:22])[c:25](=[O:26])[c:27]([C:28](=[O:29])[OH:30])[cH:31][n:32]3[CH:33]2[CH2:34][CH2:35]2)[CH2:20][C:17]1([CH3:18])[CH3:19])=[O:11])[CH:14]([CH3:15])[CH3:16]>>[CH3:1][O:2][c:3]1[c:4]([N:5]2[CH2:6... | COc1c(N2CCC(NC(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)C)C(C)(C)C2)c(F)cc2c(=O)c(C(=O)O)cn(C3CC3)c12 | COc1c(N2CCC(NC(=O)[C@@H](N)C(C)C)C(C)(C)C2)c(F)cc2c(=O)c(C(=O)O)cn(C3CC3)c12 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=c1ccn(C2CC2)c2cc(N3CCCCC3)ccc12 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[#7:6]-[C:7]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4](=[O;D1;H0:5])-[#7:6]-[C:7] | 75 | [{"value": 75.0, "product": "Cl.C1(CC1)N1C=C(C(C2=CC(=C(C(=C12)OC)N1CC(C(CC1)NC([C@@H](N)C(C)C)=O)(C)C)F)=O)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-Cyclopropyl-6-fluoro-8-methoxy-1,4-dihydro-7-{4′-(N-t-butoxycarbonyl-L-valyl)amino-3′,3′-dimethylpiperidin-1-yl)-4-oxo-quinoline-3-carboxylic acid (0.4 gm) is hydrolysed with 6N HCl (20 ml) at room temperature for 1 hr. The mixture concentrated to furnish the titled product. Yield 75%, m.p 150–55° C., C26H35FN4O5.HCl... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | C1CC[NH]CC1.c1ccc2ncccc2c1.C1CC1 | HO- | null | null | null | COc1c(N2CCC(NC(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)C)C(C)(C)C2)c(F)cc2c(=O)c(C(=O)O)cn(C3CC3)c12>>COc1c(N2CCC(NC(=O)[C@@H](N)C(C)C)C(C)(C)C2)c(F)cc2c(=O)c(C(=O)O)cn(C3CC3)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4e7fa853fe9144349445c73f356f4216 | CC(=O)[O-].C[C@]12CC[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1CCC2=O>>COc1cc2c(cc1O)CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12 | C[C@]12CC[C@@H]3C=4C=CC(=CC4CC[C@H]3[C@@H]1CCC2=O)O.C(C)(=O)[O-].II>>C[C@]12CC[C@@H]3C4=CC(=C(C=C4CC[C@H]3[C@@H]1CCC2=O)O)OC | C[C:1](=O)[O-:2].[cH:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[OH:9])[CH2:10][CH2:11][C@@H:12]1[C@@H:13]2[CH2:14][CH2:15][C@:16]2([CH3:17])[C:18](=[O:19])[CH2:20][CH2:21][C@@H:22]12>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[OH:9])[CH2:10][CH2:11][C@@H:12]1[C@@H:13]2[CH2:14][CH2:15][C@:16]2([CH3:17])[C:18](=[O:19])[CH2:... | CC(=O)[O-].C[C@]12CC[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1CCC2=O | COc1cc2c(cc1O)CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12 | null | [Cu](Cl)Cl | C(C)(=O)O | Heteroatom Alkylation and Arylation | OtherReaction | 567463fc0073611df3498872ee9dfdfd53452ffe53e3f40ae355b2833cb32d58 | 4872557aad018a5da67162c8c3d3939f17f713d6f4190285b52663574dbc6c51 | O=C1CC[C@@H]2C1CC[C@@H]1c3ccccc3CC[C@H]12 | C-[C;H0;D3;+0:1](=O)-[O-;H0;D1:2].[O;D1;H1:3]-[c:4](:[c:5]):[cH;D2;+0:6]:[c:7]:[c:8]>>[CH3;D1;+0:1]-[O;H0;D2;+0:2]-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:4](-[O;D1;H1:3]):[c:5] | 56 | [{"value": 56.0, "product": "C[C@]12CC[C@@H]3C4=CC(=C(C=C4CC[C@H]3[C@@H]1CCC2=O)O)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To this end, 2-iodo-estrone 49 was prepared by treating oestrone with mercuric-acetate and iodine in acetic acid.40 The selective halogenation at position 2 was complete within 2 hours at room temperature with an overall yield of 56% after successive recrystallizations. 2-Iodo-estrone then reacted with a large excess o... | 10.6084/m9.figshare.5104873.v1 | null | null | Ether | c1ccc2c(c1)CC[C@H]1[C@@H]3CCC[C@H]3CC[C@H]21 | c1ccc2c(c1)CC[C@H]1[C@@H]3CCC[C@H]3CC[C@H]21 | c1ccc2c(c1)CC[C@H]1[C@@H]3CCC[C@H]3CC[C@H]21 | HO- | [Cu](Cl)Cl.C(C)(=O)O | null | 2 | CC(=O)[O-].C[C@]12CC[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1CCC2=O>[Cu](Cl)Cl.C(C)(=O)O>COc1cc2c(cc1O)CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7423384ad4ba4b52b3db5009c5cdea3d | CC(C)CCON=O.C[C@]12CC[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1CCC2=O>>C[C@]12CC[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1C/C(=N\O)C2=O | N(=O)OCCC(C)C.CC(C)([O-])C.[K+].[K].C[C@]12CC[C@@H]3C=4C=CC(=CC4CC[C@H]3[C@@H]1CCC2=O)O>>C[C@]12CC[C@H]3[C@H]([C@@H]1C/C(=N\O)/C2=O)CCC4=C3C=CC(=C4)O | CC(C)CCO[N:19]=[O:20].[CH3:1][C@:2]12[CH2:3][CH2:4][C@@H:5]3[c:6]4[cH:7][cH:8][c:9]([OH:10])[cH:11][c:12]4[CH2:13][CH2:14][C@H:15]3[C@@H:16]1[CH2:17][CH2:18][C:21]2=[O:22]>>[CH3:1][C@:2]12[CH2:3][CH2:4][C@@H:5]3[c:6]4[cH:7][cH:8][c:9]([OH:10])[cH:11][c:12]4[CH2:13][CH2:14][C@H:15]3[C@@H:16]1[CH2:17]/[C:18](=[N:19]\[OH:... | CC(C)CCON=O.C[C@]12CC[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1CCC2=O | C[C@]12CC[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1C/C(=N\O)C2=O | null | null | O.C(C)(C)(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 69f613ae5efe83065cdc4e392660c20b4e375f1aa4184fbc91dd841520bfd5d6 | 31357763b1be60679a29f55afc8815d0b4a90e485d09aebc6e88f16eae688399 | N=C1C[C@@H]2C(CC[C@@H]3c4ccccc4CC[C@H]32)C1=O | C-C(-C)-C-C-O-[N;H0;D2;+0:1]=[O;H0;D1;+0:2].[O;D1;H0:3]=[C:4]1-[C:5]-[C:6]-[C:7]-[CH2;D2;+0:8]-1>>[O;D1;H0:3]=[C:4]1-[C:5]-[C:6]-[C:7]/[C;H0;D3;+0:8]-1=[N;H0;D2;+0:1]\[OH;D1;+0:2] | null | [] | null | null | 1 | HOUR | To a stirred solution of potassium tert-butoxide under an atmosphere of N2, freshly prepared by dissolving potassium metal (80 mg, 2.05 mmol) in 2 mL tert-butanol, oestrone (200 mg, 740 mmol) was added. The reaction mixture was then stirred for 1 hour at room temperature under N2 and isoamyl nitrite (180 μmol, 1.34 mmo... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Nitroso | Ketone.Oxime | c1ccc2c(c1)CC[C@H]1[C@@H]3CCC[C@@H]3CC[C@H]21 | c1ccc2c(c1)CC[C@H]1[C@@H]3CCC[C@@H]3CC[C@H]21 | c1ccc2c(c1)CC[C@H]1[C@@H]3CCC[C@@H]3CC[C@H]21 | HO- | O.C(C)(C)(C)O | null | 1 | CC(C)CCON=O.C[C@]12CC[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1CCC2=O>O.C(C)(C)(C)O>C[C@]12CC[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1C/C(=N\O)C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-80e9b56178c6445892639d64b6cc2feb | BrCc1ccccc1.C1CCC2=NCCCN2CC1.CC(C)=O.O=C(O)c1ccccc1S>>O=C(OCc1ccccc1)c1ccccc1SCc1ccccc1 | C(C=1C(S)=CC=CC1)(=O)O.N12CCCCCC2=NCCC1.C(C1=CC=CC=C1)Br.CC(=O)C>>C(C1=CC=CC=C1)OC(C1=C(C=CC=C1)SCC1=CC=CC=C1)=O | Br[CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1.C1CN=[C:5]2N(C1)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2.CC(=O)[CH3:4].[O:1]=[C:2]([OH:3])[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[SH:17]>>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[S:17][CH2:18][c:19]1[c... | BrCc1ccccc1.C1CCC2=NCCCN2CC1.CC(C)=O.O=C(O)c1ccccc1S | O=C(OCc1ccccc1)c1ccccc1SCc1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 3587d2846beccc4aebc4d88741992ffdcd9c26c041b8300002334aa10a43b9a7 | 125454d352e5f6371d8c1aa27aa9f834a08731b5739777d93d0a1ea0f93cce71 | O=C(OCc1ccccc1)c1ccccc1SCc1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].C-C(=O)-[CH3;D1;+0:5].C1-C-N=[C;H0;D3;+0:6]2-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[CH2;D2;+0:10]-[CH2;D2;+0:11]-N-2-C-1.[O;D1;H0:12]=[C:13](-[OH;D1;+0:14])-[c:15]:[c:16](-[SH;D1;+0:17]):[c:18]>>[O;D1;H0:12]=[C:13](-[O;H0;D2;+0:14]-[CH2;D2;+0:5]-[c;H0;D3;+0:6]1:[cH;D2;+0:11]:[cH... | null | [] | null | null | 50 | MINUTE | A solution of thiosalicylic acid 1 (2.0 g, 13.0 mmol) in 13 mL of acetone was treated with 1,8-Diazabicyclo [5.4.0]undec-7-ene (7.8 mL, 52 mmol) and benzylbromide (6.2 mL, 52 mmol). The reaction was stirred at room temperature for 50 minutes. The mixture was concentrated under vacuum to remove the acetone. Water was ad... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid.Ketone.Tertiary amine.Aromatic thiol | Ester.Monosulfide | C1CCC2=NCCCN2CC1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | HBr | null | null | 0.833333 | BrCc1ccccc1.C1CCC2=NCCCN2CC1.CC(C)=O.O=C(O)c1ccccc1S>>O=C(OCc1ccccc1)c1ccccc1SCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5efd89b5050f46a987a88ade1df59f7b | O=C(OCc1ccccc1)c1ccccc1SCc1ccccc1>>O=C(O)c1ccccc1SCc1ccccc1 | C(C1=CC=CC=C1)OC(C1=C(C=CC=C1)SCC1=CC=CC=C1)=O.[OH-].[Na+].[OH-].[K+]>>C(C1=CC=CC=C1)SC1=C(C(=O)O)C=CC=C1 | c1ccc(C[O:3][C:2](=[O:1])[c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[S:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)cc1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[S:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | O=C(OCc1ccccc1)c1ccccc1SCc1ccccc1 | O=C(O)c1ccccc1SCc1ccccc1 | null | null | null | Deprotection | Ester saponification (alkyl deprotection) | 86a971d3e4f88009ab4c98512e9f1deb51b2f0ce5cbd068cc61ae878c1e58e2a | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(CSc2ccccc2)cc1 | [O;D1;H0:1]=[C:2](-[c:3])-[O;H0;D2;+0:4]-C-c1:c:c:c:c:c:1>>[O;D1;H0:1]=[C:2](-[OH;D1;+0:4])-[c:3] | null | [] | null | null | 8 | HOUR | To a suspension of 2-benzylsulfanyl benzoic acid benzyl ester 2 (113 mg, 0.34 mmol) was added 1.6 mL of 1N NaOH. KOH (1 pellet) was added and the reaction was continued overnight. The acetone was removed and a small amount of water was added. The aqueous solution was washed with CH2Cl2(3). The aqueous phase was acidifi... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | c1ccccc1 | null | c1ccccc1.c1ccccc1 | Other | null | null | 8 | O=C(OCc1ccccc1)c1ccccc1SCc1ccccc1>>O=C(O)c1ccccc1SCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-63615ad3fdcf46798ec103c948af08a5 | O=C(O)c1ccccc1SCc1ccccc1>>OCc1ccccc1SCc1ccccc1 | CO.C(C1=CC=CC=C1)SC1=C(C(=O)O)C=CC=C1.[H-].[H-].[H-].[H-].[Li+].[Al+3].Cl>>C(C1=CC=CC=C1)SC1=C(C=CC=C1)CO | O=[C:2]([OH:1])[c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[S:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[S:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1 | O=C(O)c1ccccc1SCc1ccccc1 | OCc1ccccc1SCc1ccccc1 | null | null | O1CCCC1 | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | c1ccc(CSc2ccccc2)cc1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[c:3](:[c:4]):[c:5]>>[O;D1;H1:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | 63.2 | [{"value": 63.2, "product": "C(C1=CC=CC=C1)SC1=C(C=CC=C1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 15 | MINUTE | To a solution of 2-benzylsulfanyl benzoic acid 3 (50 mg, 0.206 mmol) in THF at 0° C. was added LiAlH4 (0.62 mL of a 1.0 mL solution in THF, 0.62 mmol) and the mixture was stirred at 0° C. for 15 minutes then allowed to warm to room temperature. The solution was stirred for 2 hours. The mixture was cooled at 0° C. then ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccccc1.c1ccccc1 | Other | O1CCCC1 | 0 | 0.25 | O=C(O)c1ccccc1SCc1ccccc1>O1CCCC1>OCc1ccccc1SCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dae2fd9bf2a242829a417f449efb103f | BrP(Br)Br.OCc1ccccc1SCc1ccccc1>>BrCc1ccccc1SCc1ccccc1 | C(C1=CC=CC=C1)SC1=C(C=CC=C1)CO.P(Br)(Br)Br>>BrCC1=C(C=CC=C1)SCC1=CC=CC=C1 | BrP(Br)[Br:1].O[CH2:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[S:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[Br:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[S:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1 | BrP(Br)Br.OCc1ccccc1SCc1ccccc1 | BrCc1ccccc1SCc1ccccc1 | null | null | CCOCC | Functional Group Interconversion | PBr3 and alcohol to alkyl bromide | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | c1ccc(CSc2ccccc2)cc1 | Br-P(-Br)-[Br;H0;D1;+0:1].O-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 62.3 | [{"value": 62.3, "product": "BrCC1=C(C=CC=C1)SCC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of (2-Benzylsulfanyl)methanol 4 (120 mg, 0.522 mmol) in anhydrous Et2O was cooled to 4° C. A solution of PBr3 (49 μL, 0.52 mmol) in anhydrous Et2O was added dropwise, keeping the temperature below 10° C. The reaction was allowed to warm to ambient temperature and stirred for one hour. The reaction was filter... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ccccc1.c1ccccc1 | HBr | CCOCC | null | 1 | BrP(Br)Br.OCc1ccccc1SCc1ccccc1>CCOCC>BrCc1ccccc1SCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8fffbf1b50974b6b881bccdfa25d750b | CCNc1ccc(C(=O)OC)cn1.SC(c1ccccc1)c1ccccc1CBr>>COC(=O)c1ccc(NCCCc2ccccc2SCc2ccccc2)nc1 | BrCC1=C(C=CC=C1)C(C1=CC=CC=C1)S.COC(C1=CN=C(C=C1)NCC)=O.[H-].[Na+]>>COC(C1=CN=C(C=C1)NCCCC1=C(C=CC=C1)SCC1=CC=CC=C1)=O | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][CH2:10][CH3:11])[n:27][cH:28]1.Br[CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[CH:20]([SH:19])[c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][CH2:10][CH2:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]... | CCNc1ccc(C(=O)OC)cn1.SC(c1ccccc1)c1ccccc1CBr | COC(=O)c1ccc(NCCCc2ccccc2SCc2ccccc2)nc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | c0e42512825c84f1ff04cc08b33986dec6f12a28a8be11f8a4cea70d065ed7d9 | b05f7dda7dad719ae1868a84c33eeaf5bf649036fc64173cf4774a5eb4d70181 | c1ccc(CSc2ccccc2CCCNc2ccccn2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[CH;D3;+0:5](-[SH;D1;+0:6])-[c:7](:[c:8]):[c:9]):[c:10]:[c:11].[#7:12]-[C:13]-[CH3;D1;+0:14]>>[#7:12]-[C:13]-[CH2;D2;+0:14]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[S;H0;D2;+0:6]-[CH2;D2;+0:5]-[c:7](:[c:8]):[c:9]):[c:10]:[c:11] | 70 | [{"value": 70.0, "product": "COC(C1=CN=C(C=C1)NCCCC1=C(C=CC=C1)SCC1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of methyl-6-ethylaminonicotinate in (59 mg, 0.332 mmol) DMF (0.8 mL) was added to sodium hydride (12 mg, 0.293 mL) in DMF (0.8 mL) at 0° C. The reaction was stirred for 1 hour and a solution of 2-(2-bromomethylphenyl sulfanylmethyl) benzene 5 (81 mg, 0.276 mmol) in 80 μL of DMF was added. The reaction was al... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aliphatic thiol | Monosulfide | c1ccccc1 | c1ccccc1 | c1ccncc1.c1ccccc1.c1ccccc1 | HBr | CN(C)C=O | null | 1 | CCNc1ccc(C(=O)OC)cn1.SC(c1ccccc1)c1ccccc1CBr>CN(C)C=O>COC(=O)c1ccc(NCCCc2ccccc2SCc2ccccc2)nc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f2219ebfb64740f68d7e74bc0bbba3d4 | COC(=O)c1ccc(NCCCc2ccccc2SCc2ccccc2)nc1>>O=C(O)c1ccc(NCCCc2ccccc2SCc2ccccc2)nc1 | COC(C1=CN=C(C=C1)NCCCC1=C(C=CC=C1)SCC1=CC=CC=C1)=O.[OH-].[K+]>>C(C1=CC=CC=C1)SC1=C(CCCNC2=NC=C(C(=O)O)C=C2)C=CC=C1 | C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]([NH:8][CH2:9][CH2:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[S:18][CH2:19][c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[n:26][cH:27]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([NH:8][CH2:9][CH2:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[S:18][CH2:19][c:2... | COC(=O)c1ccc(NCCCc2ccccc2SCc2ccccc2)nc1 | O=C(O)c1ccc(NCCCc2ccccc2SCc2ccccc2)nc1 | null | null | C1CCOC1.O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(CSc2ccccc2CCCNc2ccccn2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | 50 | CELSIUS | null | null | To a solution of the ester of Example 6 in THF (0.8 mL) was added a solution of KOH (14 mg, 0.255 mmol) in H2O (0.2 mL). The mixture was stirred at 50° C., then concentrated to remove THF. The aqueous phase was washed with ethyl ether, then the aqueous phase was acidified until pH 3–4 was reached. The acidified solutio... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccncc1.c1ccccc1.c1ccccc1 | Other | C1CCOC1.O | 50 | null | COC(=O)c1ccc(NCCCc2ccccc2SCc2ccccc2)nc1>C1CCOC1.O>O=C(O)c1ccc(NCCCc2ccccc2SCc2ccccc2)nc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-017ce98eaa81431ebe760c68997d8b03 | COC(=O)CC(=O)CCl.O=C1c2ccccc2C(=O)N1CCO>>COC(=O)CC(=O)COCCN1C(=O)c2ccccc2C1=O | [H-].[Na+].[H-].[Na+].ClCC(CC(=O)OC)=O.ClCC(CC(=O)OC)=O.[Cl-].[NH4+].OCCN1C(C=2C(C1=O)=CC=CC2)=O.Cl.[H-].[Na+]>>COC(CC(COCCN1C(C2=CC=CC=C2C1=O)=O)=O)=O | Cl[CH2:8][C:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])=[O:7].[OH:9][CH2:10][CH2:11][N:12]1[C:13](=[O:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[C:21]1=[O:22]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][C:6](=[O:7])[CH2:8][O:9][CH2:10][CH2:11][N:12]1[C:13](=[O:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[C:21]1=[O:22] | COC(=O)CC(=O)CCl.O=C1c2ccccc2C(=O)N1CCO | COC(=O)CC(=O)COCCN1C(=O)c2ccccc2C1=O | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | fbcfc5578f28d9d8930a708c71944acf35323dc567d3a35141adc89c3fb4ae9e | 7d4d679c705f72095ba1d241e831385ef35d8aef34f3127d947d089fa3227973 | O=C1NC(=O)c2ccccc21 | Cl-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5](-[#8:6])=[O;D1;H0:7].[C:8]-[C:9]-[OH;D1;+0:10]>>[#8:6]-[C:5](=[O;D1;H0:7])-[C:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:10]-[C:9]-[C:8] | null | [] | null | null | 30 | MINUTE | To a stirred suspension of sodium hydride (60% dispersion in mineral oil, 6.28 g, 157 mmol) in N,N-dimethylformamide (150 mL) under nitrogen at 0° C. was added portion wise N-(2-hydroxyethyl)phthalimide (2, 20 g, 105 mmol). The reaction mixture was then allowed to warm to ambient temperature with stirring for 30 minute... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Primary alcohol | Ketone.Ether | null | null | c1ccc2c(c1)C[NH]C2 | HCl | CN(C=O)C | null | 0.5 | COC(=O)CC(=O)CCl.O=C1c2ccccc2C(=O)N1CCO>CN(C=O)C>COC(=O)CC(=O)COCCN1C(=O)c2ccccc2C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-86bb6c1c56cf4becacfd08467622ce3d | COC(=O)C1=C(C)NC(COCCN2C(=O)c3ccccc3C2=O)=C(C(=O)OC)C1c1ccccc1Cl>>COC(=O)C1=C(C)NC(COCCN)=C(C(=O)OC)C1c1ccccc1Cl | CN.COC(=O)C1=C(NC(=C(C1C1=C(C=CC=C1)Cl)C(=O)OC)C)COCCN1C(C2=CC=CC=C2C1=O)=O>>COC(=O)C1=C(NC(=C(C1C1=C(C=CC=C1)Cl)C(=O)OC)C)COCCN | O=C1c2ccccc2C(=O)[N:14]1[CH2:13][CH2:12][O:11][CH2:10][C:9]1=[C:15]([C:16](=[O:17])[O:18][CH3:19])[CH:20]([c:21]2[cH:22][cH:23][cH:24][cH:25][c:26]2[Cl:27])[C:5]([C:3]([O:2][CH3:1])=[O:4])=[C:6]([CH3:7])[NH:8]1>>[CH3:1][O:2][C:3](=[O:4])[C:5]1=[C:6]([CH3:7])[NH:8][C:9]([CH2:10][O:11][CH2:12][CH2:13][NH2:14])=[C:15]([C:... | COC(=O)C1=C(C)NC(COCCN2C(=O)c3ccccc3C2=O)=C(C(=O)OC)C1c1ccccc1Cl | COC(=O)C1=C(C)NC(COCCN)=C(C(=O)OC)C1c1ccccc1Cl | null | null | O | Reduction | Phthalimide deprotection | d9f63cee80ef758bd939ff2a10772447b3092f1576180488281833a98eb1691a | dbfe4201a9328005dfaec4c3f363ddbb4ef3c9b825f648735dc97b2b57396333 | C1=CC(c2ccccc2)C=CN1 | O=C1-[N;H0;D3;+0:1](-[C:2]-[C:3])-C(=O)-c2:c:c:c:c:c:2-1>>[C:3]-[C:2]-[NH2;D1;+0:1] | 84 | [{"value": 84.0, "product": "COC(=O)C1=C(NC(=C(C1C1=C(C=CC=C1)Cl)C(=O)OC)C)COCCN", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To a stirred solution of methylamine (40 wt % in water, 125 mL, 1.45 mol) at ambient temperature was added 4-(2-chloro-phenyl)-2-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethoxymethyl]-6-methyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid dimethyl ester (dimethylamlodipine phthalimide) (4, 6.30 g, 12.0 mmol). The reaction... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Primary amine | c1ccc2c(c1)C[NH]C2 | null | C1=CNC=CC1.c1ccccc1 | HO- | O | null | 18 | COC(=O)C1=C(C)NC(COCCN2C(=O)c3ccccc3C2=O)=C(C(=O)OC)C1c1ccccc1Cl>O>COC(=O)C1=C(C)NC(COCCN)=C(C(=O)OC)C1c1ccccc1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5026b40714514b03bf4016e828417bd4 | CCOC(=O)CBr.Oc1ccccc1Cl>>CCOC(=O)COc1ccccc1Cl | ClC1=C(C=CC=C1)O.C([O-])([O-])=O.[K+].[K+].BrCC(=O)OCC>>ClC1=C(OCC(=O)OCC)C=CC=C1 | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[OH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[Cl:14]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[Cl:14] | CCOC(=O)CBr.Oc1ccccc1Cl | CCOC(=O)COc1ccccc1Cl | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 50d675b335c583a6ce22e1164b27a78b18b9ca447d45137820c344bcb6369217 | 0865de4e1853c59ac25437e36fd18b03329566cb9eff4b4f0ce70d5714692fd3 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9] | 95 | [{"value": 95.0, "product": "ClC1=C(OCC(=O)OCC)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 7 | HOUR | To a stirred solution of 2-chlorophenol (6, 20.0 g, 156 mmol) in acetone (300 mL) under nitrogen at ambient temperature were added potassium carbonate (23.7 g, 171 mmol) and ethyl bromoacetate (7, 26.0 g, 156 mmol). The reaction mixture was then heated to reflux and stirred at this temperature under nitrogen for 7 hour... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1ccccc1 | HBr | CC(=O)C | null | 7 | CCOC(=O)CBr.Oc1ccccc1Cl>CC(=O)C>CCOC(=O)COc1ccccc1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-eae56509a51f4eea830b1991cad1252d | CCOC(=O)COc1ccccc1Cl.O=C1CCC(=O)O1>>CCOC(=O)COc1ccc(C(=O)CCC(=O)O)cc1Cl | [Cl-].[Cl-].[Cl-].[Al+3].Cl.ClC1=C(OCC(=O)OCC)C=CC=C1.C1(CCC(=O)O1)=O>>ClC=1C=C(C=CC1OCC(=O)OCC)C(CCC(=O)O)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][cH:11][cH:19][c:20]1[Cl:21].[C:12]1(=[O:13])[CH2:14][CH2:15][C:16](=[O:17])[O:18]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([C:12](=[O:13])[CH2:14][CH2:15][C:16](=[O:17])[OH:18])[cH:19][c:20]1[Cl:21] | CCOC(=O)COc1ccccc1Cl.O=C1CCC(=O)O1 | CCOC(=O)COc1ccc(C(=O)CCC(=O)O)cc1Cl | null | null | ClCCl.O.CCCCCC | C-C Coupling | OtherReaction | 95de0079bfd4d0e2b70eac1863ad8bac063c1a1557f674f5eb3c0cde67534555 | 4836357c99dfeeac9d5083fedc379181a858ae45ac77bd85eb46e7e1a9df36f0 | c1ccccc1 | [O;D1;H0:1]=[C;H0;D3;+0:2]1-[C:3]-[C:4]-[C:5](=[O;D1;H0:6])-[O;H0;D2;+0:7]-1.[c:8]:[c:9]:[cH;D2;+0:10]:[c:11]:[c:12]>>[O;D1;H0:1]=[C;H0;D3;+0:2](-[C:3]-[C:4]-[C:5](=[O;D1;H0:6])-[OH;D1;+0:7])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:9]:[c:8] | 46 | [{"value": 46.0, "product": "ClC=1C=C(C=CC1OCC(=O)OCC)C(CCC(=O)O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.8, "product": "ClC=1C=C(C=CC1OCC(=O)OCC)C(CCC(=O)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | To a stirred solution of ethyl 2-chlorophenoxyacetate (32.0 g, 149 mmol) in dichloromethane (75 mL) at ambient temperature under nitrogen was added succinic anhydride (22.4 g, 224 mmol). The reaction mixture was cooled in ice-water and to this was added portion wise aluminum trichloride (59.6 g, 447 mmol), whilst maint... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride | Carboxylic acid.Ketone | c1ccccc1.C1CCOC1 | c1ccccc1 | c1ccccc1 | null | ClCCl.O.CCCCCC | null | 0.333333 | CCOC(=O)COc1ccccc1Cl.O=C1CCC(=O)O1>ClCCl.O.CCCCCC>CCOC(=O)COc1ccc(C(=O)CCC(=O)O)cc1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e465fd2a4d7d484db6d6c5f3ee938d03 | CCOC(=O)COc1ccc(C(=O)CCC(=O)O)cc1Cl.NN>>CCOC(=O)COc1ccc(C2=NNC(=O)CC2)cc1Cl | ClC=1C=C(C=CC1OCC(=O)OCC)C(CCC(=O)O)=O.O.NN.C(C)(=O)OCC>>ClC=1C=C(C=CC1OCC(=O)OCC)C=1CCC(NN1)=O | O=[C:12]([c:11]1[cH:10][cH:9][c:8]([O:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:20]([Cl:21])[cH:19]1)[CH2:18][CH2:17][C:15](O)=[O:16].[NH2:13][NH2:14]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([C:12]2=[N:13][NH:14][C:15](=[O:16])[CH2:17][CH2:18]2)[cH:19][c:20]1[Cl:21] | CCOC(=O)COc1ccc(C(=O)CCC(=O)O)cc1Cl.NN | CCOC(=O)COc1ccc(C2=NNC(=O)CC2)cc1Cl | null | null | C(C)O | Acylation | OtherReaction | 16e715242dd5e92f711d46176c552652cef6c6f4fed9bc9a09a311d5b0b86cea | 30de68c4dde17a0553a43eee47b1b865b8390bb08557512a59e6e71e0ed0ad51 | O=C1CCC(c2ccccc2)=NN1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[C;H0;D3;+0:5](=O)-[c:6](:[c:7]):[c:8].[NH2;D1;+0:9]-[NH2;D1;+0:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[C:3]-[C:4]-[C;H0;D3;+0:5](-[c:6](:[c:7]):[c:8])=[N;H0;D2;+0:9]-[NH;D2;+0:10]-1 | 82 | [{"value": 82.0, "product": "ClC=1C=C(C=CC1OCC(=O)OCC)C=1CCC(NN1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.9, "product": "ClC=1C=C(C=CC1OCC(=O)OCC)C=1CCC(NN1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a stirred suspension of 4-[3-chloro-4-(ethoxycarbonylmethoxy)phenyl]-4-oxobutyric acid (9, 21.5 g, 69.2 mmol) in ethanol (200 mL) at 0° C. was added a solution of hydrazine monohydrate (3.4 mL, 69.2 mmol) in ethanol (20 mL). The reaction mixture was then allowed to warm to ambient temperature and stirred at this tem... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Carboxylic acid.Ketone | Hydrazone amide | null | C1=NNCCC1 | c1ccccc1.C1=NNCCC1 | HO- | C(C)O | null | 0.25 | CCOC(=O)COc1ccc(C(=O)CCC(=O)O)cc1Cl.NN>C(C)O>CCOC(=O)COc1ccc(C2=NNC(=O)CC2)cc1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9e3c8905ad5848d0b462ca54136edada | CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)OC)C1c1ccccc1Cl.COC(=O)C1=C(C)NC(COCCNC(=O)COc2ccc(C3=NNC(=O)CC3)cc2Cl)=C(C(=O)OC)C1c1ccccc1Cl>>CCOC(=O)C1=C(COCCNC(=O)COc2ccc(C3=NNC(=O)CC3)cc2Cl)NC(C)=C(C(=O)OC)C1c1ccccc1Cl | CCOC(=O)C1=C(NC(=C(C1C=2C=CC=CC2Cl)C(=O)OC)C)COCCN.COC(=O)C1=C(NC(=C(C1C1=C(C=CC=C1)Cl)C(=O)OC)C)COCCNC(COC1=C(C=C(C=C1)C1=NNC(CC1)=O)Cl)=O>>COC(=O)C=1C(C(=C(NC1C)COCCNC(COC1=C(C=C(C=C1)C1=NNC(CC1)=O)Cl)=O)C(=O)OCC)C1=C(C=CC=C1)Cl | CC1=[C:34]([C:35](=[O:36])[O:37][CH3:38])[CH:39]([c:40]2[cH:41][cH:42][cH:43][cH:44][c:45]2[Cl:46])[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=C(COCCN)N1.COC(=O)C1=[C:7]([CH2:8][O:9][CH2:10][CH2:11][NH:12][C:13](=[O:14])[CH2:15][O:16][c:17]2[cH:18][cH:19][c:20]([C:21]3=[N:22][NH:23][C:24](=[O:25])[CH2:26][CH2:27]3)[cH:28][... | CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)OC)C1c1ccccc1Cl.COC(=O)C1=C(C)NC(COCCNC(=O)COc2ccc(C3=NNC(=O)CC3)cc2Cl)=C(C(=O)OC)C1c1ccccc1Cl | CCOC(=O)C1=C(COCCNC(=O)COc2ccc(C3=NNC(=O)CC3)cc2Cl)NC(C)=C(C(=O)OC)C1c1ccccc1Cl | null | null | C(C)(=O)OCC | C-C Coupling | C-methylation | 991ef25f130cd8776315b973312b825ea0a94dec3c6fd3100f8fab6fe1a2f552 | c9b6e2cd26c7ffa8fb0a921dc817e22528473e561d6cdba32960a72974848c04 | O=C(COc1ccc(C2=NNC(=O)CC2)cc1)NCCOCC1=CC(c2ccccc2)C=CN1 | C-C1=[C;H0;D3;+0:1](-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5])-[C:6](-[c:7])-[C;H0;D3;+0:8](-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12])=C(-C-O-C-C-N)-N-1.C-O-C(=O)-C1=[C;H0;D3;+0:13](-[C;D1;H3:14])-[#7:15]-[C;H0;D3;+0:16](-[C:17]-[#8:18])=C(-C(=O)-O-C)-C-1-c1:c:c:c:c:c:1-Cl>>[#8:18]-[C:17]-[C;H0;D3;+0:16]1=[C;H0;D3;+0:8](-[C:9... | null | [] | null | null | null | null | 2-(2-{2-[2-Chloro-4-(6-oxo-1,4,5,6-tetrahydro-pyridazin-3-yl)-phenoxy]-acetylamino}-ethoxymethyl)-4-(2-chloro-phenyl)-6-methyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-ethyl ester 5-methyl ester (Compound 9) (12b) was synthesized from commercial amlodipine (5b, 1.73 g, 4.23 mmol) and 6-{4-[3-carboxymethoxy]-3-chlor... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Enamine.Enamine.Enamine.Aromatic halide.Ester.Ester.Ester.Ester.Ether.Primary amine | Enamine.Enamine | C1=CNC=CC1.C1=CNC=CC1.c1ccccc1 | C1=CNC=CC1 | C1=CNC=CC1.c1ccccc1.C1=NNCCC1.c1ccccc1 | HCl | C(C)(=O)OCC | null | null | CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)OC)C1c1ccccc1Cl.COC(=O)C1=C(C)NC(COCCNC(=O)COc2ccc(C3=NNC(=O)CC3)cc2Cl)=C(C(=O)OC)C1c1ccccc1Cl>C(C)(=O)OCC>CCOC(=O)C1=C(COCCNC(=O)COc2ccc(C3=NNC(=O)CC3)cc2Cl)NC(C)=C(C(=O)OC)C1c1ccccc1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ba9cd433d44c4544b97682e7fc2afe04 | COc1ccc(CC(C)=O)cc1.O=C1c2ccccc2C(=O)N1CCO>>COc1ccc(C(=CN(C)C)C(C)=O)cc1 | COC1=CC=C(C=C1)CC(C)=O.OCCN1C(C=2C(C1=O)=CC=CC2)=O>>CN(C=C(C(C)=O)C1=CC=C(C=C1)OC)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][C:12]([CH3:13])=[O:14])[cH:15][cH:16]1.O=[C:8]1c2ccccc2[C:11](=O)[N:9]1[CH2:10]CO>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[CH:8][N:9]([CH3:10])[CH3:11])[C:12]([CH3:13])=[O:14])[cH:15][cH:16]1 | COc1ccc(CC(C)=O)cc1.O=C1c2ccccc2C(=O)N1CCO | COc1ccc(C(=CN(C)C)C(C)=O)cc1 | null | null | CN(C=O)C | C-C Coupling | OtherReaction | 092f5b96cdca59773c55c84adb5154494e2d05b38df5e238a86d6579703c89c6 | fce7ac4596c484840786e290c5c5aa7005570b15ca9f60e5b2f53666a5a8303b | c1ccccc1 | O-C-[CH2;D2;+0:1]-[#7:2]1-[C;H0;D3;+0:3](=O)-c2:c:c:c:c:c:2-[C;H0;D3;+0:4]-1=O.[C;D1;H3:5]-[C:6](=[O;D1;H0:7])-[CH2;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[C;D1;H3:5]-[C:6](=[O;D1;H0:7])-[C;H0;D3;+0:8](=[CH;D2;+0:4]-[#7:2](-[CH3;D1;+0:1])-[CH3;D1;+0:3])-[c:9](:[c:10]):[c:11] | null | [] | 85 | CELSIUS | 18 | HOUR | To a stirred solution of 1-(4-methoxy-phenyl)-propan-2-one (1, 8.37 g, 51.0 mmol) in N,N-dimethylformamide (200 mL) was added dimethoxymethyl-dimethyl-amine (2, 27 mL, 203 mmol). The reaction mixture was then stirred for 18 h at 85° C., allowed to cool to ambient temperature and excess solvent and reagents were removed... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Substituted dicarboximide.Primary alcohol | Enamine.Ketone | c1ccc2c(c1)C[NH]C2 | null | c1ccccc1 | HO- | CN(C=O)C | 85 | 18 | COc1ccc(CC(C)=O)cc1.O=C1c2ccccc2C(=O)N1CCO>CN(C=O)C>COc1ccc(C(=CN(C)C)C(C)=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ba1febf7ca664aec9fbf4db68eca4f2b | COC(=O)C1=C(C)NC(COCCN2C(=O)c3ccccc3C2=O)=C(C(=O)OC)C1c1ccccc1Cl.COc1ccc(C(=CN(C)C)C(C)=O)cc1>>COc1ccc(-c2cc(C#N)c(=O)[nH]c2C)cc1 | [H-].[Na+].CN(C=C(C(C)=O)C1=CC=C(C=C1)OC)C.COC(=O)C1=C(NC(=C(C1C1=C(C=CC=C1)Cl)C(=O)OC)C)COCCN1C(C2=CC=CC=C2C1=O)=O.CO.CN(C=O)C.CN(C=O)C>>COC1=CC=C(C=C1)C=1C=C(C(NC1C)=O)C#N | COC(=O)C1=C(COCCN2C(=O)c3ccccc3C2=O)[NH:14][C:12](C)=[C:9]([C:10](=O)OC)C1c1ccccc1Cl.C[N:11](C)[CH:8]=[C:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:18][cH:17]1)[C:15](=[O:13])[CH3:16]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([C:10]#[N:11])[c:12](=[O:13])[nH:14][c:15]2[CH3:16])[cH:17][cH:18]1 | COC(=O)C1=C(C)NC(COCCN2C(=O)c3ccccc3C2=O)=C(C(=O)OC)C1c1ccccc1Cl.COc1ccc(C(=CN(C)C)C(C)=O)cc1 | COc1ccc(-c2cc(C#N)c(=O)[nH]c2C)cc1 | null | null | null | Miscellaneous | OtherReaction | d83041445e6d6641eb268cda1c72c8d3912dcdaec571f5490b38d57eaea0fc8e | c6faffc0d12ce7db8d4328d9c2eb7707c494f8cbe970d2c3f1718980fe70e332 | O=c1ccc(-c2ccccc2)c[nH]1 | C-O-C(=O)-C1=C(-C-O-C-C-N2-C(=O)-c3:c:c:c:c:c:3-C-2=O)-[NH;D2;+0:1]-[C;H0;D3;+0:2](-C)=[C;H0;D3;+0:3](-[C;H0;D3;+0:4](=O)-O-C)-C-1-c1:c:c:c:c:c:1-Cl.C-[N;H0;D3;+0:5](-C)-[CH;D2;+0:6]=[C;H0;D3;+0:7](-[C;H0;D3;+0:8](-[C;D1;H3:9])=[O;H0;D1;+0:10])-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]>>[C;D1;H3:9]-[c;H0;D3;+0:8]1:... | 82 | [{"value": 82.0, "product": "COC1=CC=C(C=C1)C=1C=C(C(NC1C)=O)C#N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a stirred solution of sodium hydride (60% dispersion in mineral oil, 4.5 g, 112 mmol) in N,N-dimethylformamide (100 mL) was added dropwise at 0° C. a solution of crude 4-dimethylamino-3-(4-methoxyphenyl)-but-3-en-2-one (3) from the previous step, 2-cyano-acetamide (4, 4.75 g, 56.5 mmol) and methanol (4.54 mL, 112 mm... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Enamine.Enamine.Aromatic halide.Ketone.Ester.Ester.Ether.Substituted dicarboximide | Nitrile | C1=CNC=CC1.c1ccc2c(c1)CNC2.c1ccccc1 | c1cnccc1 | c1ccccc1.c1cnccc1 | HCl | null | null | 0.25 | COC(=O)C1=C(C)NC(COCCN2C(=O)c3ccccc3C2=O)=C(C(=O)OC)C1c1ccccc1Cl.COc1ccc(C(=CN(C)C)C(C)=O)cc1>>COc1ccc(-c2cc(C#N)c(=O)[nH]c2C)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2b7de4ef98f44debbfc0e293c0fd87ff | COc1ccc(-c2cc(C#N)c(=O)[nH]c2C)cc1>>Cc1[nH]c(=O)c(C#N)cc1-c1ccc(O)cc1 | COC1=CC=C(C=C1)C=1C=C(C(NC1C)=O)C#N.B(Br)(Br)Br.[Cl-].[NH4+]>>OC1=CC=C(C=C1)C=1C=C(C(NC1C)=O)C#N | C[O:15][c:14]1[cH:13][cH:12][c:11](-[c:10]2[c:2]([CH3:1])[nH:3][c:4](=[O:5])[c:6]([C:7]#[N:8])[cH:9]2)[cH:17][cH:16]1>>[CH3:1][c:2]1[nH:3][c:4](=[O:5])[c:6]([C:7]#[N:8])[cH:9][c:10]1-[c:11]1[cH:12][cH:13][c:14]([OH:15])[cH:16][cH:17]1 | COc1ccc(-c2cc(C#N)c(=O)[nH]c2C)cc1 | Cc1[nH]c(=O)c(C#N)cc1-c1ccc(O)cc1 | null | null | ClCCl.C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=c1ccc(-c2ccccc2)c[nH]1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 46 | [{"value": 46.0, "product": "OC1=CC=C(C=C1)C=1C=C(C(NC1C)=O)C#N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | To a stirred solution of 5-(4-Methoxy-phenyl)-6-methyl-2-oxo-1,2-dihydro-pyridine-3-carbonitrile (5, 10.0 g, 41.6 mmol) in dichloromethane (200 mL) was added dropwise at 0° C. a solution of boron tribromide (11.8 mL, 125 mmol) in DCM (125 mL). The reaction mixture was stirred for 6 h at ambient temperature, poured into... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1cnccc1.c1ccccc1 | Other | ClCCl.C(Cl)Cl | null | 6 | COc1ccc(-c2cc(C#N)c(=O)[nH]c2C)cc1>ClCCl.C(Cl)Cl>Cc1[nH]c(=O)c(C#N)cc1-c1ccc(O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6d859fe22634473586ac9c6a9326aa48 | CCOC(=O)CBr.Cc1[nH]c(=O)c(C#N)cc1-c1ccc(O)cc1>>CCOC(=O)COc1ccc(-c2cc(C#N)c(=O)[nH]c2C)cc1 | [H-].[Na+].BrCC(=O)OCC.OC1=CC=C(C=C1)C=1C=C(C(NC1C)=O)C#N>>C(C)OC(COC1=CC=C(C=C1)C1=C(NC(C(=C1)C#N)=O)C)=O | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[OH:7][c:8]1[cH:9][cH:10][c:11](-[c:12]2[cH:13][c:14]([C:15]#[N:16])[c:17](=[O:18])[nH:19][c:20]2[CH3:21])[cH:22][cH:23]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][c:11](-[c:12]2[cH:13][c:14]([C:15]#[N:16])[c:17](=[O:18])[nH:19][c:20]2[CH3:21])[cH:22][cH:... | CCOC(=O)CBr.Cc1[nH]c(=O)c(C#N)cc1-c1ccc(O)cc1 | CCOC(=O)COc1ccc(-c2cc(C#N)c(=O)[nH]c2C)cc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 50d675b335c583a6ce22e1164b27a78b18b9ca447d45137820c344bcb6369217 | 0865de4e1853c59ac25437e36fd18b03329566cb9eff4b4f0ce70d5714692fd3 | O=c1ccc(-c2ccccc2)c[nH]1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9] | 29 | [{"value": 29.0, "product": "C(C)OC(COC1=CC=C(C=C1)C1=C(NC(C(=C1)C#N)=O)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a stirred suspension of sodium hydride (60% dispersion in mineral oil, 1.16 g, 29.0 mmol) in N,N-dimethylformamide (50 mL), was added at 0° C. a solution of 5-(4-hydroxy-phenyl)-6-methyl-2-oxo-1,2-dihydro-pyridine-3-carbonitrile (6, 3.25 g, 14.4 mmol) in N,N-dimethylformamide (50 mL). The mixture was stirred at ambi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1ccccc1.c1cnccc1 | HBr | CN(C=O)C | null | 0.5 | CCOC(=O)CBr.Cc1[nH]c(=O)c(C#N)cc1-c1ccc(O)cc1>CN(C=O)C>CCOC(=O)COc1ccc(-c2cc(C#N)c(=O)[nH]c2C)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-22332d90ab204b59b4587a38c7a50d0f | CCOC(=O)COc1ccc(-c2cc(C#N)c(=O)[nH]c2C)cc1>>Cc1[nH]c(=O)c(C#N)cc1-c1ccc(OCC(=O)O)cc1 | C(C)OC(COC1=CC=C(C=C1)C1=C(NC(C(=C1)C#N)=O)C)=O.O.[OH-].[Li+]>>C(#N)C1=CC(=C(NC1=O)C)C1=CC=C(OCC(=O)O)C=C1 | CC[O:19][C:17]([CH2:16][O:15][c:14]1[cH:13][cH:12][c:11](-[c:10]2[c:2]([CH3:1])[nH:3][c:4](=[O:5])[c:6]([C:7]#[N:8])[cH:9]2)[cH:21][cH:20]1)=[O:18]>>[CH3:1][c:2]1[nH:3][c:4](=[O:5])[c:6]([C:7]#[N:8])[cH:9][c:10]1-[c:11]1[cH:12][cH:13][c:14]([O:15][CH2:16][C:17](=[O:18])[OH:19])[cH:20][cH:21]1 | CCOC(=O)COc1ccc(-c2cc(C#N)c(=O)[nH]c2C)cc1 | Cc1[nH]c(=O)c(C#N)cc1-c1ccc(OCC(=O)O)cc1 | null | null | O.O1CCOCC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1ccc(-c2ccccc2)c[nH]1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 64 | [{"value": 64.0, "product": "C(#N)C1=CC(=C(NC1=O)C)C1=CC=C(OCC(=O)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a stirred solution of [4-(5-Cyano-2-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)phenoxy]-acetic acid ethyl ester (7, 1.3 g, 4.16 mmol) in a mixture of 1,4-dioxane (25 mL) and water (25 mL) was added lithium hydroxide mono hydrate (700 mg, 16.7 mmol). The reaction mixture was stirred for 2 h at ambient temperature, diluted... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cnccc1.c1ccccc1 | Other | O.O1CCOCC1 | null | 2 | CCOC(=O)COc1ccc(-c2cc(C#N)c(=O)[nH]c2C)cc1>O.O1CCOCC1>Cc1[nH]c(=O)c(C#N)cc1-c1ccc(OCC(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f01f8c743b97441396e61836194bfa52 | Brc1cnc2cc(Br)cnc2c1.CCC[CH2][Sn]([CH]=COCC)([CH2]CCC)[CH2]CCC>>CCOC=Cc1cnc2cc(Br)cnc2c1 | BrC=1C=NC2=CC(=CN=C2C1)Br.C(C)OC=C[Sn](CCCC)(CCCC)CCCC>>BrC=1C=NC2=CC(=CN=C2C1)C=COCC | Br[c:6]1[cH:7][n:8][c:9]2[cH:10][c:11]([Br:12])[cH:13][n:14][c:15]2[cH:16]1.CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH:5]=[CH:4][O:3][CH2:2][CH3:1]>>[CH3:1][CH2:2][O:3][CH:4]=[CH:5][c:6]1[cH:7][n:8][c:9]2[cH:10][c:11]([Br:12])[cH:13][n:14][c:15]2[cH:16]1 | Brc1cnc2cc(Br)cnc2c1.CCC[CH2][Sn]([CH]=COCC)([CH2]CCC)[CH2]CCC | CCOC=Cc1cnc2cc(Br)cnc2c1 | null | [Cl-].C(C)[N+](CC)(CC)CC.[Pd].Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | CN(C=O)C | C-C Coupling | Stille reaction_other | 5ab616ebc5c3e6946fcd598e94e4f008a0043ec516d93f70a7457ec81214ae47 | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | c1cnc2cccnc2c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[#7;a:4]:[c:5]):[c:6]:[#7;a:7]:[c:8]:1.C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[CH;D2;+0:9]=[C:10]-[#8:11]>>[#8:11]-[C:10]=[CH;D2;+0:9]-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[#7;a:4]:[c:5]):[c:6]:[#7;a:7]:[c:8]:1 | null | [] | null | null | null | null | 1,5-Naphthyridines of formula (53), wherein n is 0 or 1, and L2, L3, R4, R5, R6a and R6b are as defined in formula (I), can be prepared as described in Scheme 10. 3,7-Dibromo-[1,5]naphthyridine, prepared as described by W. W. Paudler, J. Org. Chem., 33:1384 (1968), can be treated with (2-ethoxyvinyl)tributylstannane, a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1cnc2cccnc2c1 | c1cnc2cccnc2c1 | c1cnc2cccnc2c1 | HBr.Sn | [Cl-].C(C)[N+](CC)(CC)CC.[Pd].Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.CN(C=O)C | null | null | Brc1cnc2cc(Br)cnc2c1.CCC[CH2][Sn]([CH]=COCC)([CH2]CCC)[CH2]CCC>[Cl-].C(C)[N+](CC)(CC)CC.[Pd].Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.CN(C=O)C>CCOC=Cc1cnc2cc(Br)cnc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-17b6c43c922e4d418662a15488800faa | CCOC=Cc1cnc2cc(Br)cnc2c1>>O=CCc1cnc2cc(Br)cnc2c1 | BrC=1C=NC2=CC(=CN=C2C1)C=COCC.C(=O)O>>BrC1=CN=C2C=C(C=NC2=C1)CC=O | CC[O:1][CH:2]=[CH:3][c:4]1[cH:5][n:6][c:7]2[cH:8][c:9]([Br:10])[cH:11][n:12][c:13]2[cH:14]1>>[O:1]=[CH:2][CH2:3][c:4]1[cH:5][n:6][c:7]2[cH:8][c:9]([Br:10])[cH:11][n:12][c:13]2[cH:14]1 | CCOC=Cc1cnc2cc(Br)cnc2c1 | O=CCc1cnc2cc(Br)cnc2c1 | null | null | ClCCCl | Miscellaneous | OtherReaction | c341fdc42e48cf7e12789f1fb10a9c65f84ba2f1b42598f190b56c95d40c7caa | f3a920ec0ed1e7a5c2088300ae22a9e2e42203bc8efef555e3e9c02778626f07 | c1cnc2cccnc2c1 | C-C-[O;H0;D2;+0:1]-[CH;D2;+0:2]=[CH;D2;+0:3]-[c:4]1:[c:5]:[c:6](:[#7;a:7]):[c:8]:[#7;a:9]:[c:10]:1>>[#7;a:7]:[c:6]1:[c:5]:[c:4](-[CH2;D2;+0:3]-[CH;D2;+0:2]=[O;H0;D1;+0:1]):[c:10]:[#7;a:9]:[c:8]:1 | null | [] | null | null | null | null | 1,5-Naphthyridines of formula (53), wherein n is 0 or 1, and L2, L3, R4, R5, R6a and R6b are as defined in formula (I), can be prepared as described in Scheme 10. 3,7-Dibromo-[1,5]naphthyridine, prepared as described by W. W. Paudler, J. Org. Chem., 33:1384 (1968), can be treated with (2-ethoxyvinyl)tributylstannane, a... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aldehyde | null | null | c1cnc2cccnc2c1 | Other | ClCCCl | null | null | CCOC=Cc1cnc2cc(Br)cnc2c1>ClCCCl>O=CCc1cnc2cc(Br)cnc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cf53b5edf2234da68927f86642b87876 | CC(=O)c1cnn(-c2ccccn2)c1C.CC(=O)c1sc(-c2cccs2)nc1C.N>>Cc1c(-c2ccc3cc(CCN4CCC[C@H]4C)ccc3n2)cnn1-c1ccccn1 | CC1=C(C=NN1C1=NC=CC=C1)C(C)=O.CC=1N=C(SC1C(C)=O)C=1SC=CC1.N>>CC1=C(C=NN1C1=NC=CC=C1)C1=NC2=CC=C(C=C2C=C1)CCN1[C@@H](CCC1)C | O=[C:4]([c:3]1[c:2]([CH3:1])[n:24](-[c:25]2[cH:26][cH:27][cH:28][cH:29][n:30]2)[n:23][cH:22]1)[CH3:5].O=[C:10]([CH3:17])[c:19]1s[c:6](-[c:9]2s[cH:13][cH:14][cH:8]2)[n:21][c:20]1[CH3:7].[NH3:12]>>[CH3:1][c:2]1[c:3](-[c:4]2[cH:5][cH:6][c:7]3[cH:8][c:9]([CH2:10][CH2:11][N:12]4[CH2:13][CH2:14][CH2:15][C@H:16]4[CH3:17])[cH:... | CC(=O)c1cnn(-c2ccccn2)c1C.CC(=O)c1sc(-c2cccs2)nc1C.N | Cc1c(-c2ccc3cc(CCN4CCC[C@H]4C)ccc3n2)cnn1-c1ccccn1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | b419de27be6289314990088b8bb10d926c923fa83567ef4572704ce195cd8ae6 | 3bf7066ebc2d1b0240573120ba706118413ffc73d51cbd4c4d928711656625f4 | c1ccc(-n2cc(-c3ccc4cc(CCN5CCCC5)ccc4n3)cn2)nc1 | O=[C;H0;D3;+0:1](-[CH3;D1;+0:2])-[c;H0;D3;+0:3]1:[c:4]:[#7;a:5]:[#7;a:6](-[c:7]:[#7;a:8]):[c:9]:1-[C;D1;H3:10].O=[C;H0;D3;+0:11](-[CH3;D1;+0:12])-[c;H0;D3;+0:13]1:s:[c;H0;D3;+0:14](-[c;H0;D3;+0:15]2:[cH;D2;+0:16]:[cH;D2;+0:17]:[cH;D2;+0:18]:s:2):[n;H0;D2;+0:19]:[c:20]:1-[CH3;D1;+0:21].[NH3;D0;+0:22]>>[#7;a:8]:[c:7]-[#7... | null | [] | null | null | null | null | The title compound was prepared using the procedure described in Example 1G using 1-(5-methyl-1-pyridin-2-yl-1H-pyrazol-4-yl)-ethanone (Singh, S. P., et. al. Heterocycl. Commun., 2001, 7(1), p. 49-54) for 1-(4-methyl-2-thiophen-2-yl-thiazol-5-yl)-ethanone. 1H NMR (300 MHz, CDCl3) δ 1.14 (d, J=6.10 Hz, 3H), 1.46 (m, 1H)... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone | Tertiary amine | c1cscn1.c1ccsc1 | c1ccc2ncccc2c1.C1CC[NH]C1 | c1cn[nH]c1.c1ccc2ncccc2c1.C1CC[NH]C1.c1ccncc1 | null | null | null | null | CC(=O)c1cnn(-c2ccccn2)c1C.CC(=O)c1sc(-c2cccs2)nc1C.N>>Cc1c(-c2ccc3cc(CCN4CCC[C@H]4C)ccc3n2)cnn1-c1ccccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3307087b8d5d40d38070035323b7feac | CC(=O)c1cnn(-c2cc(C(F)(F)F)cc(C)n2)c1C.CC(=O)c1sc(-c2cccs2)nc1C.N>>Cc1cc(C(F)(F)F)cc(-n2ncc(-c3ccc4cc(CCN5CCC[C@H]5C)ccc4n3)c2C)n1 | CC1=C(C=NN1C1=NC(=CC(=C1)C(F)(F)F)C)C(C)=O.CC=1N=C(SC1C(C)=O)C=1SC=CC1.N>>CC1=C(C=NN1C1=NC(=CC(=C1)C(F)(F)F)C)C1=NC2=CC=C(C=C2C=C1)CCN1[C@@H](CCC1)C | O=[C:15]([c:14]1[cH:13][n:12][n:11](-[c:10]2[cH:9][c:4]([C:5]([F:6])([F:7])[F:8])[cH:3][c:2]([CH3:1])[n:35]2)[c:33]1[CH3:34])[CH3:16].O=[C:27]([CH3:17])[c:26]1s[c:29](-[c:20]2s[cH:24][cH:25][cH:19]2)[n:32][c:31]1[CH3:30].[NH3:23]>>[CH3:1][c:2]1[cH:3][c:4]([C:5]([F:6])([F:7])[F:8])[cH:9][c:10](-[n:11]2[n:12][cH:13][c:14... | CC(=O)c1cnn(-c2cc(C(F)(F)F)cc(C)n2)c1C.CC(=O)c1sc(-c2cccs2)nc1C.N | Cc1cc(C(F)(F)F)cc(-n2ncc(-c3ccc4cc(CCN5CCC[C@H]5C)ccc4n3)c2C)n1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | b419de27be6289314990088b8bb10d926c923fa83567ef4572704ce195cd8ae6 | 3bf7066ebc2d1b0240573120ba706118413ffc73d51cbd4c4d928711656625f4 | c1ccc(-n2cc(-c3ccc4cc(CCN5CCCC5)ccc4n3)cn2)nc1 | O=[C;H0;D3;+0:1](-[CH3;D1;+0:2])-[c;H0;D3;+0:3]1:[c:4]:[#7;a:5]:[#7;a:6](-[c:7]:[#7;a:8]):[c:9]:1-[C;D1;H3:10].O=[C;H0;D3;+0:11](-[CH3;D1;+0:12])-[c;H0;D3;+0:13]1:s:[c;H0;D3;+0:14](-[c;H0;D3;+0:15]2:[cH;D2;+0:16]:[cH;D2;+0:17]:[cH;D2;+0:18]:s:2):[n;H0;D2;+0:19]:[c;H0;D3;+0:20]:1-[CH3;D1;+0:21].[NH3;D0;+0:22]>>[#7;a:8]:... | null | [] | null | null | null | null | The title compound was prepared using the procedure described in Example 1G using 1-[5-methyl-1-(6-methyl-4-trifluoromethyl-pyridin-2-yl)-1H-pyrazol-4-yl]-ethanone (Maybridge Chemical Company Ltd., catalog number CD 11385) for 1-(4-methyl-2-thiophen-2-yl-thiazol-5-yl)-ethanone. 1H NMR (300 MHz, CDCl3) δ 1.15 (d, J=6.10... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone | Tertiary amine | c1cscn1.c1ccsc1 | c1ccc2ncccc2c1.C1CC[NH]C1 | c1ccncc1.c1c[nH]nc1.c1ccc2ncccc2c1.C1CC[NH]C1 | null | null | null | null | CC(=O)c1cnn(-c2cc(C(F)(F)F)cc(C)n2)c1C.CC(=O)c1sc(-c2cccs2)nc1C.N>>Cc1cc(C(F)(F)F)cc(-n2ncc(-c3ccc4cc(CCN5CCC[C@H]5C)ccc4n3)c2C)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6f7702eb948c4c2facbd472fb7cfe693 | CC(=O)c1cnc(-c2ccccc2)s1.CC(=O)c1sc(-c2cccs2)nc1C.N>>C[C@@H]1CCCN1CCc1ccc2nc(-c3cnc(-c4ccccc4)s3)ccc2c1 | C1(=CC=CC=C1)C=1SC(=CN1)C(C)=O.CC=1N=C(SC1C(C)=O)C=1SC=CC1.N>>C[C@H]1N(CCC1)CCC=1C=C2C=CC(=NC2=CC1)C1=CN=C(S1)C1=CC=CC=C1 | O=[C:7]([CH3:1])[c:15]1[cH:16][n:17][c:18](-[c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[s:25]1.O=[C:29]([CH3:8])[c:28]1s[c:14](-[c:2]2s[cH:5][cH:4][cH:3]2)[n:13][c:12]1[CH3:11].[NH3:6]>>[CH3:1][C@@H:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][c:9]1[cH:10][cH:11][c:12]2[n:13][c:14](-[c:15]3[cH:16][n:17][c:18](-[c:19]4... | CC(=O)c1cnc(-c2ccccc2)s1.CC(=O)c1sc(-c2cccs2)nc1C.N | C[C@@H]1CCCN1CCc1ccc2nc(-c3cnc(-c4ccccc4)s3)ccc2c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 947f5d83eb846d3273efe8d20064b2d61a63c556513a28fbd92a2a50189ca563 | 3bf7066ebc2d1b0240573120ba706118413ffc73d51cbd4c4d928711656625f4 | c1ccc(-c2ncc(-c3ccc4cc(CCN5CCCC5)ccc4n3)s2)cc1 | O=[C;H0;D3;+0:1](-[CH3;D1;+0:2])-[c;H0;D3;+0:3]1:[#16;a:4]:[c:5](-[c:6]):[#7;a:7]:[c:8]:1.O=[C;H0;D3;+0:9](-[CH3;D1;+0:10])-[c;H0;D3;+0:11]1:s:[c;H0;D3;+0:12](-[c;H0;D3;+0:13]2:[cH;D2;+0:14]:[cH;D2;+0:15]:[cH;D2;+0:16]:s:2):[#7;a:17]:[c:18]:1-[CH3;D1;+0:19].[NH3;D0;+0:20]>>[CH3;D1;+0:2]-[C@@H;D3;+0:13]1-[CH2;D2;+0:14]-... | null | [] | null | null | null | null | The title compound was prepared using the procedure described in Example 1G substituting 1-(2-phenyl-thiazol-5-yl)-ethanone (Arcadi, A., et al. Eur. J. Org. Chem. 1999, 11, p. 3117-3126) for 1-(4-methyl-2-thiophen-2-yl-thiazol-5-yl)-ethanone. 1H NMR (300 MHz, CDCl3) δ 1.13 (d, J=6.10 Hz, 3H), 1.46 (m, 1H), 1.78 (m, 2H)... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone | Tertiary amine | c1cscn1.c1cscn1.c1ccsc1 | C1CC[NH]C1.c1ccc2ncccc2c1.c1cscn1 | C1CC[NH]C1.c1ccc2ncccc2c1.c1cscn1.c1ccccc1 | null | null | null | null | CC(=O)c1cnc(-c2ccccc2)s1.CC(=O)c1sc(-c2cccs2)nc1C.N>>C[C@@H]1CCCN1CCc1ccc2nc(-c3cnc(-c4ccccc4)s3)ccc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-330d9917cf7b4c2a9e7c6f80741572bb | CC(=O)c1cc(-c2ncc(C(F)(F)F)cc2Cl)no1.CC(=O)c1sc(-c2cccs2)nc1C.N>>C[C@@H]1CCCN1CCc1ccc2nc(-c3cc(-c4ncc(C(F)(F)F)cc4Cl)no3)ccc2c1 | ClC=1C(=NC=C(C1)C(F)(F)F)C1=NOC(=C1)C(C)=O.CC=1N=C(SC1C(C)=O)C=1SC=CC1.N>>ClC=1C(=NC=C(C1)C(F)(F)F)C1=NOC(=C1)C1=NC2=CC=C(C=C2C=C1)CCN1[C@@H](CCC1)C | O=[C:14]([c:15]1[cH:16][c:17](-[c:18]2[n:19][cH:20][c:21]([C:22]([F:23])([F:24])[F:25])[cH:26][c:27]2[Cl:28])[n:29][o:30]1)[CH3:31].O=[C:9]([CH3:7])[c:34]1s[c:12](-[c:2]2s[cH:5][cH:4][cH:3]2)[n:13][c:33]1[CH3:1].[NH3:6]>>[CH3:1][C@@H:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][c:9]1[cH:10][cH:11][c:12]2[n:13][c:14](-[... | CC(=O)c1cc(-c2ncc(C(F)(F)F)cc2Cl)no1.CC(=O)c1sc(-c2cccs2)nc1C.N | C[C@@H]1CCCN1CCc1ccc2nc(-c3cc(-c4ncc(C(F)(F)F)cc4Cl)no3)ccc2c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | b419de27be6289314990088b8bb10d926c923fa83567ef4572704ce195cd8ae6 | 3bf7066ebc2d1b0240573120ba706118413ffc73d51cbd4c4d928711656625f4 | c1ccc(-c2cc(-c3ccc4cc(CCN5CCCC5)ccc4n3)on2)nc1 | O=[C;H0;D3;+0:1](-[CH3;D1;+0:2])-[c;H0;D3;+0:3]1:[#8;a:4]:[#7;a:5]:[c:6](-[c:7]:[#7;a:8]):[c:9]:1.O=[C;H0;D3;+0:10](-[CH3;D1;+0:11])-[c;H0;D3;+0:12]1:s:[c;H0;D3;+0:13](-[c;H0;D3;+0:14]2:[cH;D2;+0:15]:[cH;D2;+0:16]:[cH;D2;+0:17]:s:2):[n;H0;D2;+0:18]:[c;H0;D3;+0:19]:1-[CH3;D1;+0:20].[NH3;D0;+0:21]>>[#7;a:8]:[c:7]-[c:6]1:... | null | [] | null | null | null | null | The title compound was prepared using the procedure described in Example 1G using 1-[3-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-isoxazol-5-yl]-ethanone (Key Organics Limited/Bionet Research, catalog number 10G-001) for 1-(4-methyl-2-thiophen-2-yl-thiazol-5-yl)-ethanone. 1H NMR (300 MHz, CDCl3) δ 1.13 (d, J=6.10 Hz, 3H... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone | Tertiary amine | c1cscn1.c1ccsc1 | C1CC[NH]C1.c1ccc2ncccc2c1 | C1CC[NH]C1.c1ccc2ncccc2c1.c1cnoc1.c1ccncc1 | null | null | null | null | CC(=O)c1cc(-c2ncc(C(F)(F)F)cc2Cl)no1.CC(=O)c1sc(-c2cccs2)nc1C.N>>C[C@@H]1CCCN1CCc1ccc2nc(-c3cc(-c4ncc(C(F)(F)F)cc4Cl)no3)ccc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2937c7d99e2f4511bfd8c1d0c0900d6b | CC(=O)c1c(-c2ccc(Cl)cc2)noc1C.CC(=O)c1sc(-c2cccs2)nc1C.N>>Cc1onc(-c2ccc(Cl)cc2)c1-c1ccc2cc(CCN3CCC[C@H]3C)ccc2n1 | ClC1=CC=C(C=C1)C1=NOC(=C1C(C)=O)C.CC=1N=C(SC1C(C)=O)C=1SC=CC1.N>>ClC1=CC=C(C=C1)C1=NOC(=C1C1=NC2=CC=C(C=C2C=C1)CCN1[C@@H](CCC1)C)C | O=[C:14]([c:13]1[c:2]([CH3:1])[o:3][n:4][c:5]1-[c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1)[CH3:15].O=[C:16]([c:25]1s[c:30](-[c:17]2s[cH:19][cH:24][cH:23]2)[n:31][c:26]1[CH3:27])[CH3:29].[NH3:22]>>[CH3:1][c:2]1[o:3][n:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[c:13]1-[c:14]1[cH:15][cH:16][c:17]2[cH:1... | CC(=O)c1c(-c2ccc(Cl)cc2)noc1C.CC(=O)c1sc(-c2cccs2)nc1C.N | Cc1onc(-c2ccc(Cl)cc2)c1-c1ccc2cc(CCN3CCC[C@H]3C)ccc2n1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | b419de27be6289314990088b8bb10d926c923fa83567ef4572704ce195cd8ae6 | 3bf7066ebc2d1b0240573120ba706118413ffc73d51cbd4c4d928711656625f4 | c1ccc(-c2nocc2-c2ccc3cc(CCN4CCCC4)ccc3n2)cc1 | O=[C;H0;D3;+0:1](-[CH3;D1;+0:2])-[c;H0;D3;+0:3]1:[c:4](-[C;D1;H3:5]):[#8;a:6]:[#7;a:7]:[c:8]:1-[c:9].O=[C;H0;D3;+0:10](-[CH3;D1;+0:11])-[c;H0;D3;+0:12]1:s:[c;H0;D3;+0:13](-[c;H0;D3;+0:14]2:[cH;D2;+0:15]:[cH;D2;+0:16]:[cH;D2;+0:17]:s:2):[n;H0;D2;+0:18]:[c;H0;D3;+0:19]:1-[C;D1;H3:20].[NH3;D0;+0:21]>>[C;D1;H3:5]-[c:4]1:[#... | null | [] | null | null | null | null | The title compound was prepared using the procedure described in Example 1G-substituting 1-[3-(4-chloro-phenyl)-5-methyl-isoxazol-4-yl]-ethanone (CAS # 169814-48-6, Maybridge Chemical Company Ltd., catalog number SPB 04957) for 1-(4-methyl-2-thiophen-2-yl-thiazol-5-yl)-ethanone. 1H NMR (300 MHz, CDCl3) δ 1.14 (d, J=5.7... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone | Tertiary amine | c1cscn1.c1ccsc1 | c1ccc2ncccc2c1.C1CC[NH]C1 | c1cnoc1.c1ccccc1.c1ccc2ncccc2c1.C1CC[NH]C1 | null | null | null | null | CC(=O)c1c(-c2ccc(Cl)cc2)noc1C.CC(=O)c1sc(-c2cccs2)nc1C.N>>Cc1onc(-c2ccc(Cl)cc2)c1-c1ccc2cc(CCN3CCC[C@H]3C)ccc2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-32cdb4973d2d4656b4410bc8f14c5413 | CC(=O)c1ccc(-n2ccc(=O)cc2)cc1.CC(=O)c1sc(-c2cccs2)nc1C.N>>C[C@@H]1CCCN1CCc1ccc2nc(-c3ccc(-n4ccc(=O)cc4)cc3)ccc2c1 | C(C)(=O)C1=CC=C(C=C1)N1C=CC(C=C1)=O.CC=1N=C(SC1C(C)=O)C=1SC=CC1.N>>C[C@H]1N(CCC1)CCC=1C=C2C=CC(=NC2=CC1)C1=CC=C(C=C1)N1C=CC(C=C1)=O | O=[C:14]([c:15]1[cH:16][cH:17][c:18](-[n:19]2[cH:20][cH:21][c:22](=[O:23])[cH:24][cH:25]2)[cH:26][cH:27]1)[CH3:28].O=[C:9]([CH3:7])[c:29]1s[c:12](-[c:2]2s[cH:5][cH:4][cH:3]2)[n:13][c:30]1[CH3:1].[NH3:6]>>[CH3:1][C@@H:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][c:9]1[cH:10][cH:11][c:12]2[n:13][c:14](-[c:15]3[cH:16][cH:... | CC(=O)c1ccc(-n2ccc(=O)cc2)cc1.CC(=O)c1sc(-c2cccs2)nc1C.N | C[C@@H]1CCCN1CCc1ccc2nc(-c3ccc(-n4ccc(=O)cc4)cc3)ccc2c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | b419de27be6289314990088b8bb10d926c923fa83567ef4572704ce195cd8ae6 | 3bf7066ebc2d1b0240573120ba706118413ffc73d51cbd4c4d928711656625f4 | O=c1ccn(-c2ccc(-c3ccc4cc(CCN5CCCC5)ccc4n3)cc2)cc1 | O=[C;H0;D3;+0:1](-[CH3;D1;+0:2])-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7].O=[C;H0;D3;+0:8](-[CH3;D1;+0:9])-[c;H0;D3;+0:10]1:s:[c;H0;D3;+0:11](-[c;H0;D3;+0:12]2:[cH;D2;+0:13]:[cH;D2;+0:14]:[cH;D2;+0:15]:s:2):[n;H0;D2;+0:16]:[c;H0;D3;+0:17]:1-[CH3;D1;+0:18].[NH3;D0;+0:19]>>[CH3;D1;+0:18]-[C@@H;D3;+0:12]1-[CH2;D2;+0:13]-[... | null | [] | null | null | null | null | The title compound was prepared using the procedure described in Example 1G using 1-(4-acetyl-phenyl)-1H-pyridin-4-one for 1-(4-methyl-2-thiophen-2-yl-thiazol-5-yl)-ethanone. 1H NMR (300 MHz, CDCl3) δ 1.15 (d, J=6.10 Hz, 3H), 1.49 (m, 1H), 1.78 (m, 2H), 1.95 (m, 1H), 2.27 (m, 1H), 2.43 (m, 2H), 3.05 (m, 2H), 3.16 (m, 1... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone | Tertiary amine | c1cscn1.c1ccsc1 | C1CC[NH]C1.c1ccc2ncccc2c1 | C1CC[NH]C1.c1ccc2ncccc2c1.c1ccccc1.c1ccncc1 | null | null | null | null | CC(=O)c1ccc(-n2ccc(=O)cc2)cc1.CC(=O)c1sc(-c2cccs2)nc1C.N>>C[C@@H]1CCCN1CCc1ccc2nc(-c3ccc(-n4ccc(=O)cc4)cc3)ccc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0270a166b2234c0fbf846ad340ecf1ba | CC(=O)c1ccc(N2CCCCC2)cc1.CC(=O)c1sc(-c2cccs2)nc1C.N>>C[C@@H]1CCCN1CCc1ccc2nc(-c3ccc(N4CCCCC4)cc3)ccc2c1 | N1(CCCCC1)C1=CC=C(C=C1)C(C)=O.CC=1N=C(SC1C(C)=O)C=1SC=CC1.N>>C[C@H]1N(CCC1)CCC=1C=C2C=CC(=NC2=CC1)C1=CC=C(C=C1)N1CCCCC1 | O=[C:14]([c:15]1[cH:16][cH:17][c:18]([N:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)[cH:25][cH:26]1)[CH3:27].O=[C:30]([CH3:8])[c:29]1s[c:7](-[c:9]2s[cH:5][cH:4][cH:3]2)[n:6][c:2]1[CH3:1].[NH3:13]>>[CH3:1][C@@H:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][c:9]1[cH:10][cH:11][c:12]2[n:13][c:14](-[c:15]3[cH:16][cH:17][c... | CC(=O)c1ccc(N2CCCCC2)cc1.CC(=O)c1sc(-c2cccs2)nc1C.N | C[C@@H]1CCCN1CCc1ccc2nc(-c3ccc(N4CCCCC4)cc3)ccc2c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | b419de27be6289314990088b8bb10d926c923fa83567ef4572704ce195cd8ae6 | 3bf7066ebc2d1b0240573120ba706118413ffc73d51cbd4c4d928711656625f4 | c1cc2nc(-c3ccc(N4CCCCC4)cc3)ccc2cc1CCN1CCCC1 | O=[C;H0;D3;+0:1](-[CH3;D1;+0:2])-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7].O=[C;H0;D3;+0:8](-[CH3;D1;+0:9])-[c;H0;D3;+0:10]1:s:[c;H0;D3;+0:11](-[c;H0;D3;+0:12]2:[cH;D2;+0:13]:[cH;D2;+0:14]:[cH;D2;+0:15]:s:2):[n;H0;D2;+0:16]:[c;H0;D3;+0:17]:1-[C;D1;H3:18].[NH3;D0;+0:19]>>[C;D1;H3:18]-[C@@H;D3;+0:17]1-[CH2;D2;+0:13]-[CH2;... | null | [] | null | null | null | null | The title compound was prepared using the procedure described in Example 1G using 1-(4-piperidin-1-yl-phenyl)-ethanone for 1-(4-methyl-2-thiophen-2-yl-thiazol-5-yl)-ethanone. 1H NMR (300 MHz, CDCl3) δ 1.14 (d, J=5.42 Hz, 3H), 1.70 (m, 10H), 2.24 (m, 1H), 2.39 (m, 2H), 3.01 (m, 2H), 3.14 (m, 1H), 3.29 (m, 5H), 7.04 (d, ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone | Tertiary amine | c1cscn1.c1ccsc1 | C1CC[NH]C1.c1ccc2ncccc2c1 | C1CC[NH]C1.c1ccc2ncccc2c1.c1ccccc1.C1CC[NH]CC1 | null | null | null | null | CC(=O)c1ccc(N2CCCCC2)cc1.CC(=O)c1sc(-c2cccs2)nc1C.N>>C[C@@H]1CCCN1CCc1ccc2nc(-c3ccc(N4CCCCC4)cc3)ccc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b303602573e54ce8b33be763675c3f1a | CC(=O)c1c(-c2ccccc2)nn(C)c1Cl.CC(=O)c1sc(-c2cccs2)nc1C.N>>C[C@@H]1CCCN1CCc1ccc2nc(-c3c(-c4ccccc4)nn(C)c3Cl)ccc2c1 | ClC1=C(C(=NN1C)C1=CC=CC=C1)C(C)=O.CC=1N=C(SC1C(C)=O)C=1SC=CC1.N>>ClC1=C(C(=NN1C)C1=CC=CC=C1)C1=NC2=CC=C(C=C2C=C1)CCN1[C@@H](CCC1)C | O=[C:9]([CH3:8])[c:15]1[c:16](-[c:17]2[cH:18][cH:7][cH:20][cH:21][cH:22]2)[n:23][n:24]([CH3:25])[c:26]1[Cl:27].O=[C:29]([CH3:28])[c:30]1s[c:14](-[c:2]2s[cH:5][cH:4][cH:3]2)[n:13][c:12]1[CH3:1].[NH3:6]>>[CH3:1][C@@H:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][c:9]1[cH:10][cH:11][c:12]2[n:13][c:14](-[c:15]3[c:16](-[c:17... | CC(=O)c1c(-c2ccccc2)nn(C)c1Cl.CC(=O)c1sc(-c2cccs2)nc1C.N | C[C@@H]1CCCN1CCc1ccc2nc(-c3c(-c4ccccc4)nn(C)c3Cl)ccc2c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | b6bc3a66bf778ed31f861c47ffab7e9b543e3532fbad65008d066734637da3a8 | 3bf7066ebc2d1b0240573120ba706118413ffc73d51cbd4c4d928711656625f4 | c1ccc(-c2n[nH]cc2-c2ccc3cc(CCN4CCCC4)ccc3n2)cc1 | O=[C;H0;D3;+0:1](-[CH3;D1;+0:2])-[c;H0;D3;+0:3]1:[c:4](-[c:5]2:[c:6]:[c:7]:[cH;D2;+0:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:2):[#7;a:11]:[#7;a:12](-[C;D1;H3:13]):[c:14]:1-[Cl;D1;H0:15].O=[C;H0;D3;+0:16](-[CH3;D1;+0:17])-[c;H0;D3;+0:18]1:s:[c;H0;D3;+0:19](-[c;H0;D3;+0:20]2:[cH;D2;+0:21]:[cH;D2;+0:22]:[cH;D2;+0:23]:s:2):[#7;a:24]... | null | [] | null | null | null | null | The title compound was prepared using the procedure described in Example 1G using 1-(5-chloro-1-methyl-3-phenyl-1H-pyrazol-4-yl)-ethanone for 1-(4-methyl-2-thiophen-2-yl-thiazol-5-yl)-ethanone. 1H NMR (300 MHz, CDCl3) δ 1.15 (d, J=6.10 Hz, 3H), 1.48 (m, 1H), 1.78 (m, 2H), 1.96 (m, 1H), 2.27 (q, J=8.59 Hz, 1H), 2.41 (m,... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone | Tertiary amine | c1cn[nH]c1.c1ccccc1.c1cscn1.c1ccsc1 | C1CC[NH]C1.c1ccc2ncccc2c1.c1ccccc1.c1cn[nH]c1 | C1CC[NH]C1.c1ccc2ncccc2c1.c1ccccc1.c1cn[nH]c1 | null | null | null | null | CC(=O)c1c(-c2ccccc2)nn(C)c1Cl.CC(=O)c1sc(-c2cccs2)nc1C.N>>C[C@@H]1CCCN1CCc1ccc2nc(-c3c(-c4ccccc4)nn(C)c3Cl)ccc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-321dd009aec047248955cac5da64cb75 | CC(=O)C1(c2cccnc2)CCC1.CC(=O)c1sc(-c2cccs2)nc1C.N>>C[C@@H]1CCCN1CCc1ccc2nc(C3(c4cccnc4)CCC3)ccc2c1 | N1=CC(=CC=C1)C1(CCC1)C(C)=O.CC=1N=C(SC1C(C)=O)C=1SC=CC1.N>>C[C@H]1N(CCC1)CCC=1C=C2C=CC(=NC2=CC1)C1(CCC1)C=1C=NC=CC1 | O=[C:14]([C:15]1([c:16]2[cH:17][cH:18][cH:19][n:20][cH:21]2)[CH2:22][CH2:23][CH2:24]1)[CH3:25].O=[C:28]([CH3:9])[c:27]1s[c:7](-[c:8]2s[cH:5][cH:4][cH:3]2)[n:6][c:2]1[CH3:1].[NH3:13]>>[CH3:1][C@@H:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][c:9]1[cH:10][cH:11][c:12]2[n:13][c:14]([C:15]3([c:16]4[cH:17][cH:18][cH:19][n:2... | CC(=O)C1(c2cccnc2)CCC1.CC(=O)c1sc(-c2cccs2)nc1C.N | C[C@@H]1CCCN1CCc1ccc2nc(C3(c4cccnc4)CCC3)ccc2c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | b419de27be6289314990088b8bb10d926c923fa83567ef4572704ce195cd8ae6 | 3bf7066ebc2d1b0240573120ba706118413ffc73d51cbd4c4d928711656625f4 | c1cncc(C2(c3ccc4cc(CCN5CCCC5)ccc4n3)CCC2)c1 | O=[C;H0;D3;+0:1](-[CH3;D1;+0:2])-[C:3](-[c:4]:[c:5]:[#7;a:6])(-[C:7])-[C:8].O=[C;H0;D3;+0:9](-[CH3;D1;+0:10])-[c;H0;D3;+0:11]1:s:[c;H0;D3;+0:12](-[c;H0;D3;+0:13]2:[cH;D2;+0:14]:[cH;D2;+0:15]:[cH;D2;+0:16]:s:2):[n;H0;D2;+0:17]:[c;H0;D3;+0:18]:1-[C;D1;H3:19].[NH3;D0;+0:20]>>[#7;a:6]:[c:5]:[c:4]-[C:3](-[c;H0;D3;+0:1]1:[cH... | null | [] | null | null | null | null | The title compound was prepared using the procedure described in Example 1G using 1-(1-pyridin-3-yl-cyclobutyl)-ethanone for 1-(4-methyl-2-thiophen-2-yl-thiazol-5-yl)-ethanone. 1H NMR (300 MHz, CDCl3) δ 1.12 (d, J=6.10 Hz, 3H), 1.46 (m, 1H), 1.75 (m, 2H), 1.92 (m, 1H), 2.05 (m, 2H), 2.23 (q, J=8.82 Hz, 1H), 2.37 (m, 2H... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone | Tertiary amine | c1cscn1.c1ccsc1 | C1CC[NH]C1.c1ccc2ncccc2c1 | C1CC[NH]C1.c1ccc2ncccc2c1.c1ccncc1.C1CCC1 | null | null | null | null | CC(=O)C1(c2cccnc2)CCC1.CC(=O)c1sc(-c2cccs2)nc1C.N>>C[C@@H]1CCCN1CCc1ccc2nc(C3(c4cccnc4)CCC3)ccc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-45d9adc2864247e5b37288957c003c94 | CC(=O)c1cc(-c2ccccc2)no1.CC(=O)c1sc(-c2cccs2)nc1C.N>>C[C@@H]1CCCN1CCc1ccc2nc(-c3cc(-c4ccccc4)no3)ccc2c1 | N.C1(=CC=CC=C1)C1=NOC(=C1)C(C)=O.CC=1N=C(SC1C(C)=O)C=1SC=CC1>>C[C@H]1N(CCC1)CCC=1C=C2C=CC(=NC2=CC1)C1=CC(=NO1)C1=CC=CC=C1 | O=[C:14]([c:15]1[cH:16][c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[n:24][o:25]1)[CH3:26].O=[C:29]([CH3:8])[c:28]1s[c:7](-[c:2]2s[cH:5][cH:4][cH:3]2)[n:13][c:12]1[CH3:1].[NH3:6]>>[CH3:1][C@@H:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][c:9]1[cH:10][cH:11][c:12]2[n:13][c:14](-[c:15]3[cH:16][c:17](-[c:18]4[cH:19... | CC(=O)c1cc(-c2ccccc2)no1.CC(=O)c1sc(-c2cccs2)nc1C.N | C[C@@H]1CCCN1CCc1ccc2nc(-c3cc(-c4ccccc4)no3)ccc2c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | b419de27be6289314990088b8bb10d926c923fa83567ef4572704ce195cd8ae6 | 3bf7066ebc2d1b0240573120ba706118413ffc73d51cbd4c4d928711656625f4 | c1ccc(-c2cc(-c3ccc4cc(CCN5CCCC5)ccc4n3)on2)cc1 | O=[C;H0;D3;+0:1](-[CH3;D1;+0:2])-[c;H0;D3;+0:3]1:[#8;a:4]:[#7;a:5]:[c:6](-[c:7]):[c:8]:1.O=[C;H0;D3;+0:9](-[CH3;D1;+0:10])-[c;H0;D3;+0:11]1:s:[c;H0;D3;+0:12](-[c;H0;D3;+0:13]2:[cH;D2;+0:14]:[cH;D2;+0:15]:[cH;D2;+0:16]:s:2):[n;H0;D2;+0:17]:[c;H0;D3;+0:18]:1-[CH3;D1;+0:19].[NH3;D0;+0:20]>>[CH3;D1;+0:19]-[C@@H;D3;+0:13]1-... | null | [] | null | null | null | null | The title compound was prepared using the procedure described in Example 1G substituting 1-(3-phenyl-isoxazol-5-yl)-ethanone (Ohsawa, A. et. al. Heterocycles 1978, 9, pages 1367–1373) for 1-(4-methyl-2-thiophen-2-yl-thiazol-5-yl)-ethanone. 1H NMR (300 MHz, CD3OD) δ 1.18 (d, J=6 Hz, 3H), 1.50 (m, 1H), 1.82 (m, 2H), 2.04... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone | Tertiary amine | c1cscn1.c1ccsc1 | C1CC[NH]C1.c1ccc2ncccc2c1 | C1CC[NH]C1.c1ccc2ncccc2c1.c1cnoc1.c1ccccc1 | null | null | null | null | CC(=O)c1cc(-c2ccccc2)no1.CC(=O)c1sc(-c2cccs2)nc1C.N>>C[C@@H]1CCCN1CCc1ccc2nc(-c3cc(-c4ccccc4)no3)ccc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-40fed3ffbffa447ab223a880ae23ab39 | Nc1ccnc(S(=O)(=O)[O-])c1[N+](=O)[O-].c1ccc(CNCc2ccccc2)cc1>>Nc1ccnc(N(Cc2ccccc2)Cc2ccccc2)c1[N+](=O)[O-] | C(C1=CC=CC=C1)NCC1=CC=CC=C1.[N+](=O)([O-])C=1C(=NC=CC1N)S(=O)(=O)[O-]>>C(C1=CC=CC=C1)N(C1=NC=CC(=C1[N+](=O)[O-])N)CC1=CC=CC=C1 | O=S(=O)([O-])[c:6]1[n:5][cH:4][cH:3][c:2]([NH2:1])[c:22]1[N+:23](=[O:24])[O-:25].[NH:7]([CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[NH2:1][c:2]1[cH:3][cH:4][n:5][c:6]([N:7]([CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH2:15][c:16]2[cH:17][cH:18][cH:19][... | Nc1ccnc(S(=O)(=O)[O-])c1[N+](=O)[O-].c1ccc(CNCc2ccccc2)cc1 | Nc1ccnc(N(Cc2ccccc2)Cc2ccccc2)c1[N+](=O)[O-] | null | null | null | Functional Group Addition | OtherReaction | 834cad8380f65d68f255ec27278728dabe5a480428d4eb40aa1a35567dd1b0d0 | 14b217ee1249f5dadab0b2f3fc7724668b01909ee4c312422386cba3161eba78 | c1ccc(CN(Cc2ccccc2)c2ccccn2)cc1 | O=S(=O)(-[O-])-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[c:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[c:11]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:9](-[C:8]-[c:7])-[C:10]-[c:11]):[#7;a:2]:[c:3] | null | [] | null | null | null | null | In step (2) of Reaction Scheme I a 3-nitro-4-aminopyridine-2-sulfonate of Formula XI is reacted with dibenzylamine to provide a 2-dibenzylamino-3-nitropyridin-4-amine of Formula XII. The reaction is carried out by combining a compound of Formula XI, dibenzylamine, and a tertiary amine such as triethylamine in an inert ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonic acid | Tertiary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccccc1.c1ccccc1 | HO- | null | null | null | Nc1ccnc(S(=O)(=O)[O-])c1[N+](=O)[O-].c1ccc(CNCc2ccccc2)cc1>>Nc1ccnc(N(Cc2ccccc2)Cc2ccccc2)c1[N+](=O)[O-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8fb2123c92c44b8f9bd0be7e995b3f32 | O=[N+]([O-])c1cccnc1Cl.Oc1ccccc1>>O=[N+]([O-])c1cccnc1Oc1ccccc1 | C1(=CC=CC=C1)O.ClC1=NC=CC=C1[N+](=O)[O-]>>[N+](=O)([O-])C=1C(=NC=CC1)OC1=CC=CC=C1 | Cl[c:9]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][cH:6][cH:7][n:8]1.[OH:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][n:8][c:9]1[O:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1 | O=[N+]([O-])c1cccnc1Cl.Oc1ccccc1 | O=[N+]([O-])c1cccnc1Oc1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 99925b30dd2603ae575cba81b58435d015cd6b7267cf347380904f25833af5f2 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2ccccn2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]):[#7;a:2]:[c:3] | null | [] | null | null | null | null | In step (3) of Reaction Scheme IV a 2-chloro-3-nitropyridine of Formula XXIV is reacted with phenol to provide a 3-nitro-2-phenoxypyridine of Formula XXV. Phenol is reacted with sodium hydride in a suitable solvent such as diglyme or tetrahydrofuran to form the phenoxide. The phenoxide is then reacted at ambient temper... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccccc1 | HCl | null | null | null | O=[N+]([O-])c1cccnc1Cl.Oc1ccccc1>>O=[N+]([O-])c1cccnc1Oc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-eb4d16e944f74c59bb57297171a91346 | CCCCc1nc2c(N)nc(C)c(C)c2n1CCCCN.O=C(Cl)c1ccccc1>>CCCCc1nc2c(N)nc(C)c(C)c2n1CCCCNC(=O)c1ccccc1 | C(C)S(=O)(=O)O.C(C)N(CC)CC.NCCCCN1C(=NC=2C(=NC(=C(C21)C)C)N)CCCC.C(C1=CC=CC=C1)(=O)Cl>>NC1=NC(=C(C2=C1N=C(N2CCCCNC(C2=CC=CC=C2)=O)CCCC)C)C | [CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]([CH3:12])[c:13]([CH3:14])[c:15]2[n:16]1[CH2:17][CH2:18][CH2:19][CH2:20][NH2:21].Cl[C:22](=[O:23])[c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]([CH3:12])[c:13]([CH3:14])[c:15]2[n... | CCCCc1nc2c(N)nc(C)c(C)c2n1CCCCN.O=C(Cl)c1ccccc1 | CCCCc1nc2c(N)nc(C)c(C)c2n1CCCCNC(=O)c1ccccc1 | null | null | ClCCl.C(C)(C)O | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCCCCn1cnc2cnccc21)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 56.4 | [{"value": 56.4, "product": "NC1=NC(=C(C2=C1N=C(N2CCCCNC(C2=CC=CC=C2)=O)CCCC)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Triethylamine (0.07 mL, 0.5 mmol) was added to a solution of 1-(4-aminobutyl)-2-butyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine (150 mg, 0.5 mmol) in dichloromethane (150 mL). The reaction mixture was cooled in an ice bath. Benzoyl chloride (0.07 mL, 0.5 mmol) was added and the reaction mixture was removed from the... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1cc2nc[nH]c2cn1.c1ccccc1 | HCl | ClCCl.C(C)(C)O | null | null | CCCCc1nc2c(N)nc(C)c(C)c2n1CCCCN.O=C(Cl)c1ccccc1>ClCCl.C(C)(C)O>CCCCc1nc2c(N)nc(C)c(C)c2n1CCCCNC(=O)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-02ebf6b0da704fdda783b71326798cc4 | CCCCc1nc2c(N)nc(C)c(C)c2n1CCCCN.O=S(=O)(Cl)c1ccc(F)cc1>>CCCCc1nc2c(N)nc(C)c(C)c2n1CCCCNS(=O)(=O)c1ccc(F)cc1.O | C(C)N(CC)CC.NCCCCN1C(=NC=2C(=NC(=C(C21)C)C)N)CCCC.FC1=CC=C(C=C1)S(=O)(=O)Cl>>O.NC1=NC(=C(C2=C1N=C(N2CCCCNS(=O)(=O)C2=CC=C(C=C2)F)CCCC)C)C | [CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]([CH3:12])[c:13]([CH3:14])[c:15]2[n:16]1[CH2:17][CH2:18][CH2:19][CH2:20][NH2:21].Cl[S:22](=[O:23])(=[O:24])[c:25]1[cH:26][cH:27][c:28]([F:29])[cH:30][cH:31]1>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]([CH3:12])[c:13]([C... | CCCCc1nc2c(N)nc(C)c(C)c2n1CCCCN.O=S(=O)(Cl)c1ccc(F)cc1 | CCCCc1nc2c(N)nc(C)c(C)c2n1CCCCNS(=O)(=O)c1ccc(F)cc1.O | null | null | ClCCl | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=S(=O)(NCCCCn1cnc2cnccc21)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 43 | [{"value": 43.0, "product": "O.NC1=NC(=C(C2=C1N=C(N2CCCCNS(=O)(=O)C2=CC=C(C=C2)F)CCCC)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | Triethylamine (0.07 mL, 0.5 mmol) was added to a solution of 1-(4-aminobutyl)-2-butyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine (150 mg, 0.5 mmol) in dichloromethane (150 mL). The reaction mixture was cooled in an ice bath. 4-fluorobenzenesulfonyl chloride (113 mg, 0.5 mmol) was added and the reaction mixture was r... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1cc2nc[nH]c2cn1.c1ccccc1 | null | ClCCl | null | 48 | CCCCc1nc2c(N)nc(C)c(C)c2n1CCCCN.O=S(=O)(Cl)c1ccc(F)cc1>ClCCl>CCCCc1nc2c(N)nc(C)c(C)c2n1CCCCNS(=O)(=O)c1ccc(F)cc1.O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4a854fb3441e4f0bb5ab3b1ac5e53424 | CCCCc1nc2c(N)nc(C)c(C)c2n1CCCCN.O=C=Nc1ccccc1>>CCCCc1nc2c(N)nc(C)c(C)c2n1CCCCNC(=O)Nc1ccccc1 | C1(=CC=CC=C1)N=C=O.NCCCCN1C(=NC=2C(=NC(=C(C21)C)C)N)CCCC.C(C)OCC>>NC1=NC(=C(C2=C1N=C(N2CCCCNC(=O)NC2=CC=CC=C2)CCCC)C)C | [CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]([CH3:12])[c:13]([CH3:14])[c:15]2[n:16]1[CH2:17][CH2:18][CH2:19][CH2:20][NH2:21].[C:22](=[O:23])=[N:24][c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]([CH3:12])[c:13]([CH3:14])[c:1... | CCCCc1nc2c(N)nc(C)c(C)c2n1CCCCN.O=C=Nc1ccccc1 | CCCCc1nc2c(N)nc(C)c(C)c2n1CCCCNC(=O)Nc1ccccc1 | null | null | ClCCl | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(NCCCCn1cnc2cnccc21)Nc1ccccc1 | [C:1]-[C:2]-[NH2;D1;+0:3].[O;D1;H0:4]=[C;H0;D2;+0:5]=[N;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:5](=[O;D1;H0:4])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 90.6 | [{"value": 90.6, "product": "NC1=NC(=C(C2=C1N=C(N2CCCCNC(=O)NC2=CC=CC=C2)CCCC)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Phenylisocyanate (0.056 mL, 0.5 mmol) was added to a chilled solution of of 1-(4-aminobutyl)-2-butyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine (150 mg, 0.5 mmol) in dichloromethane (150 mL). The ice bath was removed. A white precipitate formed after 5 minutes. The reaction mixture was allowed to stir for 30 minutes... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1cc2nc[nH]c2cn1.c1ccccc1 | null | ClCCl | null | 0.5 | CCCCc1nc2c(N)nc(C)c(C)c2n1CCCCN.O=C=Nc1ccccc1>ClCCl>CCCCc1nc2c(N)nc(C)c(C)c2n1CCCCNC(=O)Nc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f4478d06628b43f99b4b9e1ba58a7ed6 | CCCCc1nc2c(N)nc(C)c(C)c2n1CCCCN.CN(C)S(=O)(=O)Cl>>CCCCc1nc2c(N)nc(C)c(C)c2n1CCCCNS(=O)(=O)N(C)C | C(C)N(CC)CC.NCCCCN1C(=NC=2C(=NC(=C(C21)C)C)N)CCCC.CN(S(=O)(=O)Cl)C>>NC1=NC(=C(C2=C1N=C(N2CCCCNS(=O)(=O)N(C)C)CCCC)C)C | [CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]([CH3:12])[c:13]([CH3:14])[c:15]2[n:16]1[CH2:17][CH2:18][CH2:19][CH2:20][NH2:21].Cl[S:22](=[O:23])(=[O:24])[N:25]([CH3:26])[CH3:27]>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]([CH3:12])[c:13]([CH3:14])[c:15]2[n:16]1[CH2:... | CCCCc1nc2c(N)nc(C)c(C)c2n1CCCCN.CN(C)S(=O)(=O)Cl | CCCCc1nc2c(N)nc(C)c(C)c2n1CCCCNS(=O)(=O)N(C)C | null | null | ClCCl | Miscellaneous | Sulfonamide synthesis (Schotten-Baumann) primary amine | ee1668a2f0e2bb397ddc9a4e83a520bdb837618cc27454d40dca0577d877459d | d2cf4d6d96891a83657fcfeafea25ed403b0b622a412ea954084e8dbcc84e7d4 | c1cc2[nH]cnc2cn1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[#7:4](-[C;D1;H3:5])-[C;D1;H3:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[#7:4](-[C;D1;H3:5])-[C;D1;H3:6] | 11 | [{"value": 11.0, "product": "NC1=NC(=C(C2=C1N=C(N2CCCCNS(=O)(=O)N(C)C)CCCC)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 113 | HOUR | Triethylamine (0.031 mL, 0.23 mmol) was added to a solution of 1-(4-aminobutyl)-2-butyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine (67 mg, 0.23 mmol) in dichloromethane (45 mL). The reaction mixture was cooled in an ice bath. Dimethylsulfamoyl chloride (0.025 mL, 0.23 mmol) was added. The reaction mixture was remove... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonamide | null | null | c1cc2nc[nH]c2cn1 | HCl | ClCCl | null | 113 | CCCCc1nc2c(N)nc(C)c(C)c2n1CCCCN.CN(C)S(=O)(=O)Cl>ClCCl>CCCCc1nc2c(N)nc(C)c(C)c2n1CCCCNS(=O)(=O)N(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1c8094ffd6f24c0698475b5c9484c8e6 | CC(C)(C)OC(=O)NCCCCN.Cc1nc(Cl)c([N+](=O)[O-])c(Cl)c1C>>Cc1nc(Cl)c([N+](=O)[O-])c(CCCCNC(=O)OC(C)(C)C)c1C | NCCCCNC(OC(C)(C)C)=O.ClC1=NC(=C(C(=C1[N+](=O)[O-])Cl)C)C.CN(C=O)C.C(C)N(CC)CC>>ClC1=NC(=C(C(=C1[N+](=O)[O-])CCCCNC(OC(C)(C)C)=O)C)C | N[CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22].Cl[c:10]1[c:6]([N+:7](=[O:8])[O-:9])[c:4]([Cl:5])[n:3][c:2]([CH3:1])[c:23]1[CH3:24]>>[CH3:1][c:2]1[n:3][c:4]([Cl:5])[c:6]([N+:7](=[O:8])[O-:9])[c:10]([CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:17])[O:18][C:19]([CH3:20... | CC(C)(C)OC(=O)NCCCCN.Cc1nc(Cl)c([N+](=O)[O-])c(Cl)c1C | Cc1nc(Cl)c([N+](=O)[O-])c(CCCCNC(=O)OC(C)(C)C)c1C | null | null | C(C)(=O)OCC | C-C Coupling | OtherReaction | f3d1ab6c54ac589fac5a43806e9f697540d0cca35b8b6491a53eb735f16f8fab | f8f6249a611c8abdf0606ba1e9b6a39027cec01df7af88837ac3b2ec74a1dced | c1ccncc1 | Cl-[c;H0;D3;+0:1]1:[c:2](-[C;D1;H3:3]):[c:4](-[C;D1;H3:5]):[#7;a:6]:[c:7](-[Cl;D1;H0:8]):[c:9]:1-[#7;+:10].N-[CH2;D2;+0:11]-[C:12]-[C:13]>>[#7;+:10]-[c:9]1:[c:7](-[Cl;D1;H0:8]):[#7;a:6]:[c:4](-[C;D1;H3:5]):[c:2](-[C;D1;H3:3]):[c;H0;D3;+0:1]:1-[CH2;D2;+0:11]-[C:12]-[C:13] | 79.8 | [{"value": 79.8, "product": "ClC1=NC(=C(C(=C1[N+](=O)[O-])CCCCNC(OC(C)(C)C)=O)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Tert-butyl 4-aminobutylcarbamate (60 g, 339 mmol) was slowly added to a mixture of 2,4-dichloro-5,6-dimethyl-3-nitropyridine (50 g, 226 mmol), anhydrous N,N-dimethylformamide (500 mL) and triethylamine (50 mL, 339 mmol). The reaction mixture was allowed to stir overnight and then it was concentrated under reduced press... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | null | c1ccncc1 | c1ccncc1 | c1ccncc1 | HCl | C(C)(=O)OCC | null | 8 | CC(C)(C)OC(=O)NCCCCN.Cc1nc(Cl)c([N+](=O)[O-])c(Cl)c1C>C(C)(=O)OCC>Cc1nc(Cl)c([N+](=O)[O-])c(CCCCNC(=O)OC(C)(C)C)c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bb93c39f72fe408db0b2f8095a491a48 | Cc1nc(Oc2ccccc2)c([N+](=O)[O-])c(NCCCCNC(=O)OC(C)(C)C)c1C>>Cc1nc(Oc2ccccc2)c(N)c(NCCCCNC(=O)OC(C)(C)C)c1C | CC1=NC(=C(C(=C1C)NCCCCNC(OC(C)(C)C)=O)[N+](=O)[O-])OC1=CC=CC=C1.C1(=CC=CC=C1)C>>NC=1C(=NC(=C(C1NCCCCNC(OC(C)(C)C)=O)C)C)OC1=CC=CC=C1 | O=[N+:13]([O-])[c:12]1[c:4]([O:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:3][c:2]([CH3:1])[c:28]([CH3:29])[c:14]1[NH:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27]>>[CH3:1][c:2]1[n:3][c:4]([O:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[c:12]([NH2:13])[c:14]([NH:15][CH... | Cc1nc(Oc2ccccc2)c([N+](=O)[O-])c(NCCCCNC(=O)OC(C)(C)C)c1C | Cc1nc(Oc2ccccc2)c(N)c(NCCCCNC(=O)OC(C)(C)C)c1C | null | [Pt] | C(C)(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(Oc2ccccn2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4](-[#8:5]):[#7;a:6]:[c:7]>>[#8:5]-[c:4](:[#7;a:6]:[c:7]):[c:2](-[NH2;D1;+0:1]):[c:3] | 87.6 | [{"value": 87.6, "product": "NC=1C(=NC(=C(C1NCCCCNC(OC(C)(C)C)=O)C)C)OC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Tert-butyl 4-[(2,3-dimethyl-5-nitro-6-phenoxypyridin-4-yl)amino]butylcarbamate (9.17 g, 21.3 mmol), toluene (50 mL), isopropanol (5 mL) and 5% platinum on carbon (7.0 g) were combined and maintained under hydrogen pressure (50 psi, 3.5 Kg/cm2) overnight on a Parr apparatus. The catalyst was removed by filtration and th... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccncc1.c1ccccc1 | Other | [Pt].C(C)(C)O | null | null | Cc1nc(Oc2ccccc2)c([N+](=O)[O-])c(NCCCCNC(=O)OC(C)(C)C)c1C>[Pt].C(C)(C)O>Cc1nc(Oc2ccccc2)c(N)c(NCCCCNC(=O)OC(C)(C)C)c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-81371807103f44619e2687ec592562bd | Cc1nc(Oc2ccccc2)c2nc(C)n(CCCCNC(=O)OC(C)(C)C)c2c1C>>Cc1nc(Oc2ccccc2)c2nc(C)n(CCCCN)c2c1C | CC=1N(C2=C(C(=NC(=C2C)C)OC2=CC=CC=C2)N1)CCCCNC(OC(C)(C)C)=O.FC(C(=O)O)(F)F.[OH-].[Na+]>>CC=1N(C2=C(C(=NC(=C2C)C)OC2=CC=CC=C2)N1)CCCCN | CC(C)(C)OC(=O)[NH:21][CH2:20][CH2:19][CH2:18][CH2:17][n:16]1[c:14]([CH3:15])[n:13][c:12]2[c:4]([O:5][c:6]3[cH:7][cH:8][cH:9][cH:10][cH:11]3)[n:3][c:2]([CH3:1])[c:23]([CH3:24])[c:22]21>>[CH3:1][c:2]1[n:3][c:4]([O:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[c:12]2[n:13][c:14]([CH3:15])[n:16]([CH2:17][CH2:18][CH2:19][CH2:2... | Cc1nc(Oc2ccccc2)c2nc(C)n(CCCCNC(=O)OC(C)(C)C)c2c1C | Cc1nc(Oc2ccccc2)c2nc(C)n(CCCCN)c2c1C | null | null | ClCCl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc(Oc2nccc3[nH]cnc23)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | 87.8 | [{"value": 87.8, "product": "CC=1N(C2=C(C(=NC(=C2C)C)OC2=CC=CC=C2)N1)CCCCN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of tert-butyl 4-(2,6,7-trimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl)butylcarbamate (6.70 g, 15.8 mmol) in dichloromethane (50 mL) was slowly added to a chilled (0° C.) mixture of trifluoroacetic acid (60 mL) and dichloromethane (100 mL). The reaction mixture was allowed to warm to ambient temperature an... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1cc2nc[nH]c2cn1 | HO- | ClCCl | null | 8 | Cc1nc(Oc2ccccc2)c2nc(C)n(CCCCNC(=O)OC(C)(C)C)c2c1C>ClCCl>Cc1nc(Oc2ccccc2)c2nc(C)n(CCCCN)c2c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-43d8a7a728d449f7adb931a08b66fabf | Cc1nc(Oc2ccccc2)c2nc(C)n(CCCCNS(C)(=O)=O)c2c1C.[NH4+]>>Cc1nc(N)c2nc(C)n(CCCCNS(C)(=O)=O)c2c1C | CC=1N(C2=C(C(=NC(=C2C)C)OC2=CC=CC=C2)N1)CCCCNS(=O)(=O)C.C(C)(=O)[O-].[NH4+].Cl>>NC1=NC(=C(C2=C1N=C(N2CCCCNS(=O)(=O)C)C)C)C | c1ccc(O[c:4]2[n:3][c:2]([CH3:1])[c:21]([CH3:22])[c:20]3[c:6]2[n:7][c:8]([CH3:9])[n:10]3[CH2:11][CH2:12][CH2:13][CH2:14][NH:15][S:16]([CH3:17])(=[O:18])=[O:19])cc1.[NH4+:5]>>[CH3:1][c:2]1[n:3][c:4]([NH2:5])[c:6]2[n:7][c:8]([CH3:9])[n:10]([CH2:11][CH2:12][CH2:13][CH2:14][NH:15][S:16]([CH3:17])(=[O:18])=[O:19])[c:20]2[c:2... | Cc1nc(Oc2ccccc2)c2nc(C)n(CCCCNS(C)(=O)=O)c2c1C.[NH4+] | Cc1nc(N)c2nc(C)n(CCCCNS(C)(=O)=O)c2c1C | null | null | CO.C(Cl)(Cl)Cl.C(C)OCC | Heteroatom Alkylation and Arylation | OtherReaction | f1a3cc602ce132f4b138aaff43e359cc4e4ed2f1a7bdd06ecc27d202417b41fd | 4764b8d6a7ad8d9253070fdb827f95d720ac9a4f642f3b03b75fe3f308c3d0a7 | c1cc2[nH]cnc2cn1 | [C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]2:[c:6]:1:[c:7]:[c:8]:[#7;a:9]:[c;H0;D3;+0:10]:2-O-c1:c:c:c:c:c:1.[NH4+;D0:11]>>[C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]2:[c:6]:1:[c:7]:[c:8]:[#7;a:9]:[c;H0;D3;+0:10]:2-[NH2;D1;+0:11] | 59.1 | [{"value": 59.1, "product": "NC1=NC(=C(C2=C1N=C(N2CCCCNS(=O)(=O)C)C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | null | null | N-[4-(2,6,7-trimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl)butyl]methanesulfonamide (4.20 g, 10.4 mmol) and ammonium acetate (42 g) were combined and then heated in a sealed tube at 150° C. for 36 hrs. The reaction mixture was allowed to cool and then it was dissolved in chloroform. The solution was extracted with 1... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Primary amine | c1ccccc1.c1cc2nc[nH]c2cn1 | c1cc2nc[nH]c2cn1 | c1cc2nc[nH]c2cn1 | HO- | CO.C(Cl)(Cl)Cl.C(C)OCC | 150 | null | Cc1nc(Oc2ccccc2)c2nc(C)n(CCCCNS(C)(=O)=O)c2c1C.[NH4+]>CO.C(Cl)(Cl)Cl.C(C)OCC>Cc1nc(N)c2nc(C)n(CCCCNS(C)(=O)=O)c2c1C |
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