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-c31cb9b44c404c10ba3aa533aa079e2b | ord-f7118650aa1c49b4a2a7fb581c794a93 | O.O=S(Cl)Cl.c1ccc2c(c1)CCO2>>O=S(=O)(Cl)c1ccc2c(c1)CCO2 | S(=O)(Cl)Cl.O1CCC2=C1C=CC=C2.C(Cl)Cl.O>>O1CCC2=C1C=CC(=C2)S(=O)(=O)Cl | [OH2:3].Cl[S:2](=[O:1])[Cl:4].[cH:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[CH2:11][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)[CH2:11][CH2:12][O:13]2 | O.O=S(Cl)Cl.c1ccc2c(c1)CCO2 | O=S(=O)(Cl)c1ccc2c(c1)CCO2 | null | null | ClCCCl | Oxidation | OtherReaction | 8b01ac9c5d7b697f016d7042f2d05a3b46d0d06f578fe0c90c8043196b5281a6 | 81690bf6214dfc87f1e80e37dd7a1b86738358b56ee49d58ce8b77a9699c92f8 | c1ccc2c(c1)CCO2 | Cl-[S;H0;D3;+0:1](-[Cl;D1;H0:2])=[O;D1;H0:3].[OH2;D0;+0:4].[c:5]:[c:6]:[cH;D2;+0:7]:[c:8]:[c:9]>>[Cl;D1;H0:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;H0;D1;+0:4])-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:6]:[c:5] | 100 | [{"value": 100.0, "product": "O1CCC2=C1C=CC(=C2)S(=O)(=O)Cl", "details": "PERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | null | null | 3.56 g (29.6 mmol) 2,3-dihydrobenzofuran was added to a slurry of 5.44 g (35.5 mmol) sulfur trioxide-N,N-dimethylformamide complex in 12 mL 1,2-dichloroethane under argon. The reaction was heated to 85° C. for 1 hour and then cooled to room temperature. Thionyl chloride (2.6 mL, 35.5 mmol, 1.2 eq) was added dropwise an... | 10.6084/m9.figshare.5104873.v1 | null | null | Sulfonyl halide | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | HCl | ClCCCl | 85 | null | O.O=S(Cl)Cl.c1ccc2c(c1)CCO2>ClCCCl>O=S(=O)(Cl)c1ccc2c(c1)CCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2c29efc0e55344048d0fc25f38879fed | BrCc1noc2ccccc12.O=S(=O)(O)Cl>>O=S(=O)(Cl)c1ccc2onc(CBr)c2c1 | ClS(=O)(=O)O.BrCC1=NOC2=C1C=CC=C2>>BrCC1=NOC2=C1C=C(C=C2)S(=O)(=O)Cl | [cH:5]1[cH:6][cH:7][c:8]2[o:9][n:10][c:11]([CH2:12][Br:13])[c:14]2[cH:15]1.O[S:2](=[O:1])(=[O:3])[Cl:4]>>[O:1]=[S:2](=[O:3])([Cl:4])[c:5]1[cH:6][cH:7][c:8]2[o:9][n:10][c:11]([CH2:12][Br:13])[c:14]2[cH:15]1 | BrCc1noc2ccccc12.O=S(=O)(O)Cl | O=S(=O)(Cl)c1ccc2onc(CBr)c2c1 | null | null | null | Heteroatom Alkylation and Arylation | Aromatic sulfonyl chlorination | 1de617f597940a4b1353fa427b486b905916e0273772c5a5239bad72a4ce2f2a | d32b60b8f9bfd187c6c9f1eef6a22a00f53525a7532b83aba763d5389c9e4280 | c1ccc2oncc2c1 | O-[S;H0;D4;+0:1](-[Cl;D1;H0:2])(=[O;D1;H0:3])=[O;D1;H0:4].[#7;a:5]1:[#8;a:6]:[c:7]2:[c:8]:[c:9]:[cH;D2;+0:10]:[c:11]:[c:12]:2:[c:13]:1>>[Cl;D1;H0:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[c;H0;D3;+0:10]1:[c:11]:[c:12]2:[c:13]:[#7;a:5]:[#8;a:6]:[c:7]:2:[c:8]:[c:9]:1 | 80.2 | [{"value": 80.0, "product": "BrCC1=NOC2=C1C=C(C=C2)S(=O)(=O)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.2, "product": "BrCC1=NOC2=C1C=C(C=C2)S(=O)(=O)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 6 | HOUR | Chlorosulfonic acid (1.5 ml, 22 mmol) was slowly added to 3-Bromomethyl-benzo[d]isoxazole (1.0 g, 4.7 mmol) at RT under argon. The reaction was heated at 90° C. for 12 h and then left at RT for 6 h. The resulting viscous oil was quenched over ice, extracted with EtOAc, dried over MgSO4 and concentrated in vacuo to a br... | 10.6084/m9.figshare.5104873.v1 | null | null | Sulfonyl halide | c1ccc2oncc2c1 | c1ccc2oncc2c1 | c1ccc2oncc2c1 | HO- | null | 90 | 6 | BrCc1noc2ccccc12.O=S(=O)(O)Cl>>O=S(=O)(Cl)c1ccc2onc(CBr)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bb936bcf86b84c1b9b86441df70ddda7 | CC(=O)OC(C)=O.Cc1n[nH]c2ccccc12>>CC(=O)n1nc(C)c2ccccc21 | CC1=NNC2=CC=CC=C12.N1=CC=CC=C1.CC(=O)OC(=O)C>>CC1=NN(C2=CC=CC=C12)C(C)=O | CC(=O)O[C:2]([CH3:1])=[O:3].[nH:4]1[n:5][c:6]([CH3:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]12>>[CH3:1][C:2](=[O:3])[n:4]1[n:5][c:6]([CH3:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]12 | CC(=O)OC(C)=O.Cc1n[nH]c2ccccc12 | CC(=O)n1nc(C)c2ccccc21 | null | CN(C)C=1C=CN=CC1 | C1CCOC1 | Acylation | Ester with secondary amine to amide | d2d8e67de66decf6e048f203acc2705e43acc0e3e98f0fe3c6249b66ad1e328e | 93289da630dbaf2d9339c4212dcd342dfbcc29df4e79a63418a0fd9f589abdc1 | c1ccc2[nH]ncc2c1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[c:4]:[c:5]1:[c:6]:[c:7]:[#7;a:8]:[nH;D2;+0:9]:1>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[n;H0;D3;+0:9]1:[#7;a:8]:[c:7]:[c:6]:[c:5]:1:[c:4] | 91 | [{"value": 91.0, "product": "CC1=NN(C2=CC=CC=C12)C(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.6, "product": "CC1=NN(C2=CC=CC=C12)C(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 3-Methylindazole (1.00 g, 7.6 mmol) (J. Med. Chem. 2706 (1997)] was dissolved in 10 ml THF and stirred at room temperature under a blanket of argon. Pyridine (0.64 ml, 7.9 mmol) was added, followed by Ac2O (0.79 ml, 8.3 mmol) and catalytic DMAP (90 mg, 0.7 mmol). The reaction proceeded for 2 h and was then partitioned ... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride | null | c1ccc2[nH]ncc2c1 | c1n[nH]c2ccccc12 | c1n[nH]c2ccccc12 | HO- | CN(C)C=1C=CN=CC1.C1CCOC1 | null | 2 | CC(=O)OC(C)=O.Cc1n[nH]c2ccccc12>CN(C)C=1C=CN=CC1.C1CCOC1>CC(=O)n1nc(C)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-53d1f816a897459a8db0121cd6ac7f8e | CC(C)CN(CC(O)C(Cc1ccccc1)NC(=O)OC(C)(C)C)C(=O)OCc1ccccc1.O=C(OC1COC2OCCC12)ON1C(=O)CCC1=O>>CC(C)CN(CC(O)C(Cc1ccccc1)NC(=O)OC1COC2OCCC12)C(=O)OCc1ccccc1 | C(C1=CC=CC=C1)OC(N(CC(C)C)CC(C(CC1=CC=CC=C1)NC(=O)OC(C)(C)C)O)=O.Cl.C(C)(C)N(C(C)C)CC.O1CC(C2C1OCC2)OC(ON2C(CCC2=O)=O)=O>>C(C1=CC=CC=C1)OC(N(CC(C)C)CC(C(CC1=CC=CC=C1)NC(=O)OC1COC2OCCC21)O)=O | CC(C)(C)OC(=O)[NH:17][CH:9]([CH:7]([CH2:6][N:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[C:29](=[O:30])[O:31][CH2:32][c:33]1[cH:34][cH:35][cH:36][cH:37][cH:38]1)[OH:8])[CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1.O=C1CCC(=O)N1O[C:18](=[O:19])[O:20][CH:21]1[CH2:22][O:23][CH:24]2[O:25][CH2:26][CH2:27][CH:28]12>>[CH3:1][CH:2... | CC(C)CN(CC(O)C(Cc1ccccc1)NC(=O)OC(C)(C)C)C(=O)OCc1ccccc1.O=C(OC1COC2OCCC12)ON1C(=O)CCC1=O | CC(C)CN(CC(O)C(Cc1ccccc1)NC(=O)OC1COC2OCCC12)C(=O)OCc1ccccc1 | null | null | O1CCOCC1 | Protection | OtherReaction | 1128a7ed8198894bb78897e6f497896066e6c904d8c783a7606c5f801ae7721e | c6b87d20dd468a6b1a3f862a783b52d5f603286c2fec0192cc836668a76ce046 | O=C(NCCC(Cc1ccccc1)NC(=O)OC1COC2OCCC12)OCc1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4].O=C1-C-C-C(=O)-N-1-O-[C;H0;D3;+0:5](=[O;D1;H0:6])-[#8:7]-[C:8]>>[C:3]-[C:2](-[C:4])-[NH;D2;+0:1]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[#8:7]-[C:8] | 73.4 | [{"value": 73.0, "product": "C(C1=CC=CC=C1)OC(N(CC(C)C)CC(C(CC1=CC=CC=C1)NC(=O)OC1COC2OCCC21)O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.4, "product": "C(C1=CC=CC=C1)OC(N(CC(C)C)CC(C(CC1=CC=CC=C1)NC(=O)OC1COC2OCCC21)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | (3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyl)-isobutyl-carbamic acid benzyl ester 16 (7.54 g, 15 mmol) and 35 ml of 4M HCl in dioxane were stirred 30 min under an argon atmosphere. The mixture was concentrated in vacuo, and co-evaporated twice with dichloromethane. The residue was dissolved in dichloromethane (... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Ether.Tertiary amide.Tertiary amide.Boc | Carbamic ester | C1CCNC1 | null | c1ccccc1.C1CC2CCOC2O1.c1ccccc1 | HO- | O1CCOCC1 | null | 8 | CC(C)CN(CC(O)C(Cc1ccccc1)NC(=O)OC(C)(C)C)C(=O)OCc1ccccc1.O=C(OC1COC2OCCC12)ON1C(=O)CCC1=O>O1CCOCC1>CC(C)CN(CC(O)C(Cc1ccccc1)NC(=O)OC1COC2OCCC12)C(=O)OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-da7c1d34ef7f4336bbb01a45cf299d6f | CC(C)CN(CC(O)C(Cc1ccccc1)NC(=O)OC1COC2OCCC12)C(=O)OCc1ccccc1>>CC(C)CNCC(O)C(Cc1ccccc1)NC(=O)OC1COC2OCCC12 | C(C1=CC=CC=C1)OC(N(CC(C)C)CC(C(CC1=CC=CC=C1)NC(=O)OC1COC2OCCC21)O)=O>>O1CC(C2C1OCC2)OC(NC(C(CNCC(C)C)O)CC2=CC=CC=C2)=O | O=C(OCc1ccccc1)[N:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[CH2:6][CH:7]([OH:8])[CH:9]([CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[NH:17][C:18](=[O:19])[O:20][CH:21]1[CH2:22][O:23][CH:24]2[O:25][CH2:26][CH2:27][CH:28]12>>[CH3:1][CH:2]([CH3:3])[CH2:4][NH:5][CH2:6][CH:7]([OH:8])[CH:9]([CH2:10][c:11]1[cH:12][cH:13][cH:14... | CC(C)CN(CC(O)C(Cc1ccccc1)NC(=O)OC1COC2OCCC12)C(=O)OCc1ccccc1 | CC(C)CNCC(O)C(Cc1ccccc1)NC(=O)OC1COC2OCCC12 | null | [Pd] | C(C)O | Reduction | Hydrogenolysis of tertiary amines | 709a03512f2b36af470a6c002bf594696c9a8d9f4ff0ae82dddda03c8a91a358 | 20c36f41eeb07c3ba4437b51ba72e8ff3c22d0b27e7197b0e9af3127f331149f | O=C(NCCc1ccccc1)OC1COC2OCCC12 | O=C(-O-C-c1:c:c:c:c:c:1)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | 98 | [{"value": 97.0, "product": "O1CC(C2C1OCC2)OC(NC(C(CNCC(C)C)O)CC2=CC=CC=C2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.0, "product": "O1CC(C2C1OCC2)OC(NC(C(CNCC(C)C)O)CC2=CC=CC=C2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of [3-(hexahydro-furo[2,3-b]furan-3-yloxycarbonylamino)-2-hydroxy-4-phenyl-butyl]-isobutyl-carbamic acid benzyl ester 18 (5.5 g, 10.4 mmol) and 550 mg of 10% Pd/C in 130 ml of ethanol was stirred under a hydrogen atmosphere overnight. The catalyst was removed by filtration through Celite®, and the solution wa... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Secondary amine | c1ccccc1 | null | c1ccccc1.C1CC2CCOC2O1 | HO- | [Pd].C(C)O | null | 8 | CC(C)CN(CC(O)C(Cc1ccccc1)NC(=O)OC1COC2OCCC12)C(=O)OCc1ccccc1>[Pd].C(C)O>CC(C)CNCC(O)C(Cc1ccccc1)NC(=O)OC1COC2OCCC12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-908a968d90344375b8c2b6508cbc7955 | CC(C)CNCC(O)C(Cc1ccccc1)NC(=O)OC1COC2OCCC12.O=S(=O)(Cl)c1ccc2occc2c1>>CC(C)CN(CC(O)C(Cc1ccccc1)NC(=O)OC1COC2OCCC12)S(=O)(=O)c1ccc2occc2c1 | O1C=CC2=C1C=CC(=C2)S(=O)(=O)Cl.O1CC(C2C1OCC2)OC(NC(C(CNCC(C)C)O)CC2=CC=CC=C2)=O.C(=O)(O)[O-].[Na+]>>O1CC(C2C1OCC2)OC(NC(C(CN(CC(C)C)S(=O)(=O)C=2C=CC1=C(C=CO1)C2)O)CC2=CC=CC=C2)=O | [CH3:1][CH:2]([CH3:3])[CH2:4][NH:5][CH2:6][CH:7]([OH:8])[CH:9]([CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[NH:17][C:18](=[O:19])[O:20][CH:21]1[CH2:22][O:23][CH:24]2[O:25][CH2:26][CH2:27][CH:28]12.Cl[S:29](=[O:30])(=[O:31])[c:32]1[cH:33][cH:34][c:35]2[o:36][cH:37][cH:38][c:39]2[cH:40]1>>[CH3:1][CH:2]([CH3:3])[C... | CC(C)CNCC(O)C(Cc1ccccc1)NC(=O)OC1COC2OCCC12.O=S(=O)(Cl)c1ccc2occc2c1 | CC(C)CN(CC(O)C(Cc1ccccc1)NC(=O)OC1COC2OCCC12)S(=O)(=O)c1ccc2occc2c1 | null | null | C(Cl)Cl | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | abeb6d9a0c70fe5baef0a8e555c2cd55ac2317f763ce7a0831775db7a04777d8 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | O=C(NC(CCNS(=O)(=O)c1ccc2occc2c1)Cc1ccccc1)OC1COC2OCCC12 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[C:10]-[C:11])-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | 16 | HOUR | Benzofuran-5-sulfonyl chloride 148 mg (0.68 mmol) was dissolved in 5 mL of methylene chloride. (1-Benzyl-2-hydroxy-3-isobutylamino-propyl)-carbamic acid hexahydro-furo[2,3-b]furan-3-yl ester 19 (244 mg, 0.62 mmol) was added followed by 0.63 mL 10% NaHCO3 solution (0.75 mmol). The reaction was stirred at room temperatur... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | null | null | c1ccccc1.C1CC2CCOC2O1.c1ccc2occc2c1 | HCl | C(Cl)Cl | null | 16 | CC(C)CNCC(O)C(Cc1ccccc1)NC(=O)OC1COC2OCCC12.O=S(=O)(Cl)c1ccc2occc2c1>C(Cl)Cl>CC(C)CN(CC(O)C(Cc1ccccc1)NC(=O)OC1COC2OCCC12)S(=O)(=O)c1ccc2occc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0b020d2e3819488f85be6834a110dbfb | CC(C)CN(CC(O)C(Cc1ccccc1)NC(=O)OC1COC2OCCC12)S(=O)(=O)c1ccc2occ(CN)c2c1.O=C(Cl)c1ccccc1>>CC(C)CN(CC(O)C(Cc1ccccc1)NC(=O)OC1COC2OCCC12)S(=O)(=O)c1ccc2occ(CNC(=O)c3ccccc3)c2c1 | O1CC(C2C1OCC2)OC(NC(C(CN(CC(C)C)S(=O)(=O)C=2C=CC1=C(C(=CO1)CN)C2)O)CC2=CC=CC=C2)=O.C(C1=CC=CC=C1)(=O)Cl.C(C)N(CC)CC>>O1CC(C2C1OCC2)OC(NC(C(CN(CC(C)C)S(=O)(=O)C=2C=CC1=C(C(=CO1)CNC(C1=CC=CC=C1)=O)C2)O)CC2=CC=CC=C2)=O | [CH3:1][CH:2]([CH3:3])[CH2:4][N:5]([CH2:6][CH:7]([OH:8])[CH:9]([CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[NH:17][C:18](=[O:19])[O:20][CH:21]1[CH2:22][O:23][CH:24]2[O:25][CH2:26][CH2:27][CH:28]12)[S:29](=[O:30])(=[O:31])[c:32]1[cH:33][cH:34][c:35]2[o:36][cH:37][c:38]([CH2:39][NH2:40])[c:49]2[cH:50]1.Cl[C:41](=... | CC(C)CN(CC(O)C(Cc1ccccc1)NC(=O)OC1COC2OCCC12)S(=O)(=O)c1ccc2occ(CN)c2c1.O=C(Cl)c1ccccc1 | CC(C)CN(CC(O)C(Cc1ccccc1)NC(=O)OC1COC2OCCC12)S(=O)(=O)c1ccc2occ(CNC(=O)c3ccccc3)c2c1 | null | null | C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NC(CCNS(=O)(=O)c1ccc2occ(CNC(=O)c3ccccc3)c2c1)Cc1ccccc1)OC1COC2OCCC12 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#8;a:6]:[c:7]:[c:8]-[C:9]-[NH2;D1;+0:10]>>[#8;a:6]:[c:7]:[c:8]-[C:9]-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 52 | [{"value": 52.0, "product": "O1CC(C2C1OCC2)OC(NC(C(CN(CC(C)C)S(=O)(=O)C=2C=CC1=C(C(=CO1)CNC(C1=CC=CC=C1)=O)C2)O)CC2=CC=CC=C2)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | {3-[(3-Aminomethyl-benzofuran-5-sulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid hexahydro-furo[2,3-b]furan-3-yl ester from the previous step (20 mg, 33 umol) was dissolved in 0.5 mL THF. 5.8 uL (50 umol) benzoyl chloride and 7 uL (50 umol) triethylamine were added and the reaction was stirred at room... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC2CCOC2O1.c1ccc2occc2c1.c1ccccc1 | HCl | C1CCOC1 | null | 1 | CC(C)CN(CC(O)C(Cc1ccccc1)NC(=O)OC1COC2OCCC12)S(=O)(=O)c1ccc2occ(CN)c2c1.O=C(Cl)c1ccccc1>C1CCOC1>CC(C)CN(CC(O)C(Cc1ccccc1)NC(=O)OC1COC2OCCC12)S(=O)(=O)c1ccc2occ(CNC(=O)c3ccccc3)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c6c5ae1d98dc4816a328e83c31c6e97d | CC(C)CNCC(O)C(Cc1ccccc1)NC(=O)OC1COC2OCCC12.N#Cc1cc(S(=O)(=O)Cl)ccc1F>>CC(C)CN(CC(O)C(Cc1ccccc1)NC(=O)OC1COC2OCCC12)S(=O)(=O)c1ccc(F)c(C#N)c1 | C(=O)(O)[O-].[Na+].O1CC(C2C1OCC2)OC(NC(C(CNCC(C)C)O)CC2=CC=CC=C2)=O.FC1=C(C=C(C=C1)S(=O)(=O)Cl)C#N.C(=O)(O)[O-].[Na+]>>O1CC(C2C1OCC2)OC(NC(C(CN(CC(C)C)S(=O)(=O)C2=CC(=C(C=C2)F)C#N)O)CC2=CC=CC=C2)=O | [CH3:1][CH:2]([CH3:3])[CH2:4][NH:5][CH2:6][CH:7]([OH:8])[CH:9]([CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[NH:17][C:18](=[O:19])[O:20][CH:21]1[CH2:22][O:23][CH:24]2[O:25][CH2:26][CH2:27][CH:28]12.Cl[S:29](=[O:30])(=[O:31])[c:32]1[cH:33][cH:34][c:35]([F:36])[c:37]([C:38]#[N:39])[cH:40]1>>[CH3:1][CH:2]([CH3:3])[... | CC(C)CNCC(O)C(Cc1ccccc1)NC(=O)OC1COC2OCCC12.N#Cc1cc(S(=O)(=O)Cl)ccc1F | CC(C)CN(CC(O)C(Cc1ccccc1)NC(=O)OC1COC2OCCC12)S(=O)(=O)c1ccc(F)c(C#N)c1 | null | null | C(C)(=O)OCC | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | abeb6d9a0c70fe5baef0a8e555c2cd55ac2317f763ce7a0831775db7a04777d8 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | O=C(NC(CCNS(=O)(=O)c1ccccc1)Cc1ccccc1)OC1COC2OCCC12 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[C:10]-[C:11])-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 92 | [{"value": 92.0, "product": "O1CC(C2C1OCC2)OC(NC(C(CN(CC(C)C)S(=O)(=O)C2=CC(=C(C=C2)F)C#N)O)CC2=CC=CC=C2)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of (1-benzyl-2-hydroxy-3-isobutylamino-propyl)-carbamic acid hexahydro-furo[2,3-b]furan-3-yl ester 19 in CH2C12 (4 mL) was added 4-fluoro-3-cyanobenzenesulfonyl chloride (92 mg, 0.42 mmol) followed by NaHCO3 (40 mg) and satd. NaHCO3 (0.4 mL) and stirred at RT for 1 h. The reaction mixture was diluted with... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | null | null | c1ccccc1.C1CC2CCOC2O1.c1ccccc1 | HCl | C(C)(=O)OCC | null | null | CC(C)CNCC(O)C(Cc1ccccc1)NC(=O)OC1COC2OCCC12.N#Cc1cc(S(=O)(=O)Cl)ccc1F>C(C)(=O)OCC>CC(C)CN(CC(O)C(Cc1ccccc1)NC(=O)OC1COC2OCCC12)S(=O)(=O)c1ccc(F)c(C#N)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b6c91dcf2f8c47799cd42b39bfc4aba8 | CC(C)CNCC(O)C(Cc1ccccc1)NC(=O)OC(C)(C)C.Cc1n[nH]c2ccc(S(=O)(=O)Cl)cc12>>Cc1n[nH]c2ccc(S(=O)(=O)N(CC(C)C)CC(O)C(Cc3ccccc3)NC(=O)OC(C)(C)C)cc12 | C(C)(C)(C)OC(NC(C(CNCC(C)C)O)CC1=CC=CC=C1)=O.CC1=NNC2=CC=C(C=C12)S(=O)(=O)Cl.C(=O)(O)[O-].[Na+].C(=O)(O)[O-].[Na+].CCCCCC>>C(C)(C)(C)OC(NC(C(CN(S(=O)(=O)C=1C=C2C(=NNC2=CC1)C)CC(C)C)O)CC1=CC=CC=C1)=O | [NH:12]([CH2:13][CH:14]([CH3:15])[CH3:16])[CH2:17][CH:18]([OH:19])[CH:20]([CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1)[NH:28][C:29](=[O:30])[O:31][C:32]([CH3:33])([CH3:34])[CH3:35].Cl[S:9]([c:8]1[cH:7][cH:6][c:5]2[nH:4][n:3][c:2]([CH3:1])[c:37]2[cH:36]1)(=[O:10])=[O:11]>>[CH3:1][c:2]1[n:3][nH:4][c:5]2[cH:6][cH:... | CC(C)CNCC(O)C(Cc1ccccc1)NC(=O)OC(C)(C)C.Cc1n[nH]c2ccc(S(=O)(=O)Cl)cc12 | Cc1n[nH]c2ccc(S(=O)(=O)N(CC(C)C)CC(O)C(Cc3ccccc3)NC(=O)OC(C)(C)C)cc12 | null | null | ClCCl | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | abeb6d9a0c70fe5baef0a8e555c2cd55ac2317f763ce7a0831775db7a04777d8 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | O=S(=O)(NCCCCc1ccccc1)c1ccc2[nH]ncc2c1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[C:10]-[C:11])-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 99.5 | [{"value": 99.0, "product": "C(C)(C)(C)OC(NC(C(CN(S(=O)(=O)C=1C=C2C(=NNC2=CC1)C)CC(C)C)O)CC1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.5, "product": "C(C)(C)(C)OC(NC(C(CN(S(=O)(=O)C=1C=C2C(=NNC2=CC1)C)CC(C)C)O)CC1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To (1-Benzyl-2-hydroxy-3-isobutylamino-propyl)-carbamic acid tert-butyl ester 15 (60 mg, 0.18 mmol) and 3-methyl-1H-indazole-5-sulfonyl chloride (50 mg, 0.22 mmol) in 2 mL dichloromethane was added a 70 ul solution of a saturated NaHCO3 and 30 mg NaHCO3 and stirred overnight. The product was purified by preparative TLC... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | null | null | c1ccc2n[nH]cc2c1.c1ccccc1 | HCl | ClCCl | null | 8 | CC(C)CNCC(O)C(Cc1ccccc1)NC(=O)OC(C)(C)C.Cc1n[nH]c2ccc(S(=O)(=O)Cl)cc12>ClCCl>Cc1n[nH]c2ccc(S(=O)(=O)N(CC(C)C)CC(O)C(Cc3ccccc3)NC(=O)OC(C)(C)C)cc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ce026a901f9f47dc966a3a7150cbc0c2 | Cc1n[nH]c2ccc(S(=O)(=O)N(CC(C)C)CC(O)C(Cc3ccccc3)NC(=O)OC(C)(C)C)cc12.O=C(OC1COC2OCCC12)ON1C(=O)CCC1=O>>Cc1n[nH]c2ccc(S(=O)(=O)N(CC(C)C)CC(O)C(Cc3ccccc3)NC(=O)OC3COC4OCCC34)cc12 | O1CC(C2C1OCC2)OC(ON2C(CCC2=O)=O)=O.C(C)(C)(C)OC(NC(C(CN(S(=O)(=O)C=1C=C2C(=NNC2=CC1)C)CC(C)C)O)CC1=CC=CC=C1)=O.Cl.C(C)(C)N(CC)C(C)C>>O1CC(C2C1OCC2)OC(NC(C(CN(S(=O)(=O)C=2C=C1C(=NNC1=CC2)C)CC(C)C)O)CC2=CC=CC=C2)=O | CC(C)(C)OC(=O)[NH:28][CH:20]([CH:18]([CH2:17][N:12]([S:9]([c:8]1[cH:7][cH:6][c:5]2[nH:4][n:3][c:2]([CH3:1])[c:41]2[cH:40]1)(=[O:10])=[O:11])[CH2:13][CH:14]([CH3:15])[CH3:16])[OH:19])[CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1.O=C1CCC(=O)N1O[C:29](=[O:30])[O:31][CH:32]1[CH2:33][O:34][CH:35]2[O:36][CH2:37][CH2:38... | Cc1n[nH]c2ccc(S(=O)(=O)N(CC(C)C)CC(O)C(Cc3ccccc3)NC(=O)OC(C)(C)C)cc12.O=C(OC1COC2OCCC12)ON1C(=O)CCC1=O | Cc1n[nH]c2ccc(S(=O)(=O)N(CC(C)C)CC(O)C(Cc3ccccc3)NC(=O)OC3COC4OCCC34)cc12 | null | null | O1CCOCC1 | Protection | OtherReaction | 1128a7ed8198894bb78897e6f497896066e6c904d8c783a7606c5f801ae7721e | c6b87d20dd468a6b1a3f862a783b52d5f603286c2fec0192cc836668a76ce046 | O=C(NC(CCNS(=O)(=O)c1ccc2[nH]ncc2c1)Cc1ccccc1)OC1COC2OCCC12 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4].O=C1-C-C-C(=O)-N-1-O-[C;H0;D3;+0:5](=[O;D1;H0:6])-[#8:7]-[C:8]>>[C:3]-[C:2](-[C:4])-[NH;D2;+0:1]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[#8:7]-[C:8] | null | [] | null | null | 8 | HOUR | {1-Benzyl-2-hydroxy-3-[isobutyl-(3-methyl-1H-indazole-5-sulfonyl)-amino]-propyl}-carbamic acid tert-butyl ester (25 mg, 0.047 mmol) was added to a solution of 4N HCl in dioxane (0.25 mL). Material precipitated out so 800 uL conc. HCl was added and the reaction heated at reflux for 2 h. The resulting solution was concen... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Ether.Tertiary amide.Tertiary amide.Boc | Carbamic ester | C1CCNC1 | null | c1ccc2n[nH]cc2c1.c1ccccc1.C1CC2CCOC2O1 | HO- | O1CCOCC1 | null | 8 | Cc1n[nH]c2ccc(S(=O)(=O)N(CC(C)C)CC(O)C(Cc3ccccc3)NC(=O)OC(C)(C)C)cc12.O=C(OC1COC2OCCC12)ON1C(=O)CCC1=O>O1CCOCC1>Cc1n[nH]c2ccc(S(=O)(=O)N(CC(C)C)CC(O)C(Cc3ccccc3)NC(=O)OC3COC4OCCC34)cc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-42112608490a425faa1ac1eff5a4ebd2 | CC(=O)OC(C)=O.Cc1n[nH]c2ccccc12>>CC(=O)n1nc(C)c2ccccc21 | CC1=NNC2=CC=CC=C12.N1=CC=CC=C1.CC(=O)OC(=O)C>>CC1=NN(C2=CC=CC=C12)C(C)=O | CC(=O)O[C:2]([CH3:1])=[O:3].[nH:4]1[n:5][c:6]([CH3:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]12>>[CH3:1][C:2](=[O:3])[n:4]1[n:5][c:6]([CH3:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]12 | CC(=O)OC(C)=O.Cc1n[nH]c2ccccc12 | CC(=O)n1nc(C)c2ccccc21 | null | CN(C)C=1C=CN=CC1 | C1CCOC1 | Acylation | Ester with secondary amine to amide | d2d8e67de66decf6e048f203acc2705e43acc0e3e98f0fe3c6249b66ad1e328e | 93289da630dbaf2d9339c4212dcd342dfbcc29df4e79a63418a0fd9f589abdc1 | c1ccc2[nH]ncc2c1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[c:4]:[c:5]1:[c:6]:[c:7]:[#7;a:8]:[nH;D2;+0:9]:1>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[n;H0;D3;+0:9]1:[#7;a:8]:[c:7]:[c:6]:[c:5]:1:[c:4] | 91 | [{"value": 91.0, "product": "CC1=NN(C2=CC=CC=C12)C(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.6, "product": "CC1=NN(C2=CC=CC=C12)C(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 3-Methylindazole (1.00 g, 7.6 mmol) was dissolved in 10 ml THF and stirred at RT under a blanket of argon. Pyridine (0.64 ml, 7.9 mmol) was added followed by Ac2O (0.79 ml, 8.3 mmol) and catalytic DMAP (90 mg, 0.7 mmol). The reaction proceeded for 2 h and was then partitioned between 1N HCl and dichloromethane. The org... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride | null | c1ccc2[nH]ncc2c1 | c1n[nH]c2ccccc12 | c1n[nH]c2ccccc12 | HO- | CN(C)C=1C=CN=CC1.C1CCOC1 | null | 2 | CC(=O)OC(C)=O.Cc1n[nH]c2ccccc12>CN(C)C=1C=CN=CC1.C1CCOC1>CC(=O)n1nc(C)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-838c87c92f474128935a7992ddabd067 | CC(=O)n1nc(C)c2ccccc21.O=S(=O)(O)Cl>>Cc1n[nH]c2ccc(S(=O)(=O)Cl)cc12 | ClS(=O)(=O)O.CC1=NN(C2=CC=CC=C12)C(C)=O>>CC1=NNC2=CC=C(C=C12)S(=O)(=O)Cl | CC(=O)[n:4]1[n:3][c:2]([CH3:1])[c:14]2[c:5]1[cH:6][cH:7][cH:8][cH:13]2.O=[S:9]([OH:10])(=[O:11])[Cl:12]>>[CH3:1][c:2]1[n:3][nH:4][c:5]2[cH:6][cH:7][c:8]([S:9](=[O:10])(=[O:11])[Cl:12])[cH:13][c:14]12 | CC(=O)n1nc(C)c2ccccc21.O=S(=O)(O)Cl | Cc1n[nH]c2ccc(S(=O)(=O)Cl)cc12 | null | null | null | Protection | OtherReaction | b9dc7c87f2f45dd86e8ff60e2a7adab0bd3bba51bbf50c644b30368bb0c3eb20 | c731d053565135be022f3edbe36cf28a9b4364ca579bdb183b2db9578bab4695 | c1ccc2[nH]ncc2c1 | C-C(=O)-[n;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]2:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]:[c:9]:2:1.O=[S;H0;D4;+0:10](-[Cl;D1;H0:11])(=[O;D1;H0:12])-[OH;D1;+0:13]>>[Cl;D1;H0:11]-[S;H0;D4;+0:10](=[O;D1;H0:12])(=[O;H0;D1;+0:13])-[c;H0;D3;+0:6]1:[c:5]:[c:4]2:[c:3]:[#7;a:2]:[nH;D2;+0:1]:[c:9]:2:[c:8]:[c:7]:1 | 63.6 | [{"value": 61.0, "product": "CC1=NNC2=CC=C(C=C12)S(=O)(=O)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.6, "product": "CC1=NNC2=CC=C(C=C12)S(=O)(=O)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To chlorosulfonic acid (0.38 ml, 5.7 mmol) under a blanket of argon in an ice bath was added 1-(3-methyl-indazol-1-yl)-ethanone (200 mg, 1.1 mmol). The reaction was allowed to warm to RT and then was heated at 70° C. for 45 min. The reaction was cooled to rt, slowly quenched over ice and extracted with dichloromethane.... | 10.6084/m9.figshare.5104873.v1 | null | null | Sulfonyl halide | c1n[nH]c2ccccc12 | c1ccc2n[nH]cc2c1 | c1ccc2n[nH]cc2c1 | HO- | null | null | null | CC(=O)n1nc(C)c2ccccc21.O=S(=O)(O)Cl>>Cc1n[nH]c2ccc(S(=O)(=O)Cl)cc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ce9520244ed44683b5e5b9d1e3bd3a1b | BrCc1noc2ccccc12.O=S(=O)(O)Cl>>O=S(=O)(Cl)c1ccc2onc(CBr)c2c1 | ClS(=O)(=O)O.BrCC1=NOC2=C1C=CC=C2>>BrCC1=NOC2=C1C=C(C=C2)S(=O)(=O)Cl | [cH:5]1[cH:6][cH:7][c:8]2[o:9][n:10][c:11]([CH2:12][Br:13])[c:14]2[cH:15]1.O[S:2](=[O:1])(=[O:3])[Cl:4]>>[O:1]=[S:2](=[O:3])([Cl:4])[c:5]1[cH:6][cH:7][c:8]2[o:9][n:10][c:11]([CH2:12][Br:13])[c:14]2[cH:15]1 | BrCc1noc2ccccc12.O=S(=O)(O)Cl | O=S(=O)(Cl)c1ccc2onc(CBr)c2c1 | null | null | null | Heteroatom Alkylation and Arylation | Aromatic sulfonyl chlorination | 1de617f597940a4b1353fa427b486b905916e0273772c5a5239bad72a4ce2f2a | d32b60b8f9bfd187c6c9f1eef6a22a00f53525a7532b83aba763d5389c9e4280 | c1ccc2oncc2c1 | O-[S;H0;D4;+0:1](-[Cl;D1;H0:2])(=[O;D1;H0:3])=[O;D1;H0:4].[#7;a:5]1:[#8;a:6]:[c:7]2:[c:8]:[c:9]:[cH;D2;+0:10]:[c:11]:[c:12]:2:[c:13]:1>>[Cl;D1;H0:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[c;H0;D3;+0:10]1:[c:11]:[c:12]2:[c:13]:[#7;a:5]:[#8;a:6]:[c:7]:2:[c:8]:[c:9]:1 | 80.2 | [{"value": 80.0, "product": "BrCC1=NOC2=C1C=C(C=C2)S(=O)(=O)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.2, "product": "BrCC1=NOC2=C1C=C(C=C2)S(=O)(=O)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 6 | HOUR | Chlorosulfonic acid (1.5 ml, 22 mmol) was slowly added to 3-Bromomethyl-benzo[d]isoxazole (1.0 g, 4.7 mmol) at RT under argon. The reaction was heated at 90° C. for 12 h and then left at RT for 6 h. The resulting viscous oil was quenched over ice, extracted with EtOAc, dried over MgSO4 and concentrated in vacuo to a br... | 10.6084/m9.figshare.5104873.v1 | null | null | Sulfonyl halide | c1ccc2oncc2c1 | c1ccc2oncc2c1 | c1ccc2oncc2c1 | HO- | null | 90 | 6 | BrCc1noc2ccccc12.O=S(=O)(O)Cl>>O=S(=O)(Cl)c1ccc2onc(CBr)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a72737089aaa4ad48c4a57342ae8adb2 | C(=NC1CCCCC1)=NC1CCCCC1.O=C(O)CC(=O)O>>O=C(NC1CCCCC1)NC1CCCCC1 | C1CCC(CC1)N=C=NC2CCCCC2.C(CC(=O)O)(=O)O>>C1(CCCCC1)NC(=O)NC1CCCCC1 | [C:2](=[N:3][CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1)=[N:10][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1.O=C(O)CC(O)=[O:1]>>[O:1]=[C:2]([NH:3][CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1)[NH:10][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1 | C(=NC1CCCCC1)=NC1CCCCC1.O=C(O)CC(=O)O | O=C(NC1CCCCC1)NC1CCCCC1 | null | CN(C)C=1C=CN=CC1 | C(Cl)Cl | Miscellaneous | OtherReaction | 0642a6af5b16e884276bf15c9f7fe9e7381a3a91014ec4f6a4d25a56dfeaaf0f | 3a965eba3098fd1a397f9a7f68b5522f39b7a7b91f2a5718e79d867e06da2a35 | O=C(NC1CCCCC1)NC1CCCCC1 | O-C(=O)-C-C(-O)=[O;H0;D1;+0:1].[C:2]-[C:3](-[N;H0;D2;+0:4]=[C;H0;D2;+0:5]=[N;H0;D2;+0:6]-[C:7](-[C:8])-[C:9])-[C:10]>>[C:2]-[C:3](-[NH;D2;+0:4]-[C;H0;D3;+0:5](=[O;H0;D1;+0:1])-[NH;D2;+0:6]-[C:7](-[C:8])-[C:9])-[C:10] | 60 | [{"value": 60.0, "product": "C1(CCCCC1)NC(=O)NC1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 15 | MINUTE | 104 mg (1 mmol) of malonic acid and 1.23 g (2.2 mmol) of alcohol 7 were dissolved in dry CH2Cl2 under N2 protection and the solution cooled in an ice bath. 41.0 mg (0.20 mmol) DMAP (10 mol %) and 454 mg (2.20 mmol) DCC were added subsequently. After stirring under N2-protection for 15 min at 0° C. and 2 h at RT, TLC co... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid | Urea | null | null | C1CCCCC1.C1CCCCC1 | HO- | CN(C)C=1C=CN=CC1.C(Cl)Cl | 0 | 0.25 | C(=NC1CCCCC1)=NC1CCCCC1.O=C(O)CC(=O)O>CN(C)C=1C=CN=CC1.C(Cl)Cl>O=C(NC1CCCCC1)NC1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bb51094371c24b66b89e385748086d88 | C=C(C)C.C[SiH2]O[Si](C)(C)C.C[SiH2]O[Si](C)(C)C>>CC(C)C[Si](C)(C)O[SiH](C)C | C[SiH2]O[Si](C)(C)C.C1(=CC=CC=C1)C.CC(C)=C.C[SiH2]O[Si](C)(C)C>>CC(C[Si](O[SiH](C)C)(C)C)C | [CH3:1][C:2]([CH3:3])=[CH2:4].C[Si:9]([O:8][SiH2:5][CH3:6])([CH3:10])[CH3:11].C[SiH2]O[Si](C)(C)[CH3:7]>>[CH3:1][CH:2]([CH3:3])[CH2:4][Si:5]([CH3:6])([CH3:7])[O:8][SiH:9]([CH3:10])[CH3:11] | C=C(C)C.C[SiH2]O[Si](C)(C)C.C[SiH2]O[Si](C)(C)C | CC(C)C[Si](C)(C)O[SiH](C)C | null | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Cl-].[Rh] | null | Miscellaneous | OtherReaction | b4bff7b9dcd71eb005ee39656535d134dbcf321494767350d1f69e556c66a41c | ecf71ff1f33b95218682f89e2359975035d7e3510954631c0171914de0ec4fcf | null | C-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[#8:4]-[SiH2;D2;+0:5]-[C;D1;H3:6].C-[SiH2]-O-[Si](-C)(-C)-[CH3;D1;+0:7].[C;D1;H3:8]-[C;H0;D3;+0:9](-[C;D1;H3:10])=[CH2;D1;+0:11]>>[C;D1;H3:2]-[SiH;D3;+0:1](-[C;D1;H3:3])-[#8:4]-[Si;H0;D4;+0:5](-[C;D1;H3:6])(-[CH3;D1;+0:7])-[CH2;D2;+0:11]-[CH;D3;+0:9](-[C;D1;H3:8])-[C;D1;H3:... | null | [] | 65 | CELSIUS | null | null | An 80 mL Fischer-Porter high pressure bottle was charged with tetramethyldisiloxane (10.0 g), toluene (10.0 g) and Wilkinson's catalyst ((PPh3)3RhCl, 40 ppm), stirred and brought to 60° C. The bottle was attached to a manifold and pressurized with isobutylene (25 psig) and maintained at 60-70° C. for 8 h. The pressure ... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl.Silyl protective group.Silyl protective group | Silyl protective group | null | null | null | HO- | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Cl-].[Rh] | 65 | null | C=C(C)C.C[SiH2]O[Si](C)(C)C.C[SiH2]O[Si](C)(C)C>C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Cl-].[Rh]>CC(C)C[Si](C)(C)O[SiH](C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a084dd9163ef4076ab27ee0607da2c42 | C=CC.C[SiH2]O[Si](C)(C)C>>CCC[Si](C)(C)O[SiH](C)C | C[SiH2]O[Si](C)(C)C.C1(=CC=CC=C1)C.C=CC>>C(CC)[Si](O[SiH](C)C)(C)C | [CH3:1][CH:2]=[CH2:3].[SiH2:4]([CH3:5])[O:7][Si:8]([CH3:6])([CH3:9])[CH3:10]>>[CH3:1][CH2:2][CH2:3][Si:4]([CH3:5])([CH3:6])[O:7][SiH:8]([CH3:9])[CH3:10] | C=CC.C[SiH2]O[Si](C)(C)C | CCC[Si](C)(C)O[SiH](C)C | null | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Cl-].[Rh] | null | Miscellaneous | OtherReaction | 48aaa97344ecca5468aef29c7ae97b953b9270cac980ae6594ab741e32b388dd | a73aab15218d9f83236501cdc99718c52ca13cdc4d7f312ae7b6fa0d5a506e13 | null | [C;D1;H3:1]-[CH;D2;+0:2]=[CH2;D1;+0:3].[C;D1;H3:4]-[Si;H0;D4;+0:5](-[C;D1;H3:6])(-[CH3;D1;+0:7])-[#8:8]-[SiH2;D2;+0:9]-[C;D1;H3:10]>>[C;D1;H3:4]-[SiH;D3;+0:5](-[C;D1;H3:6])-[#8:8]-[Si;H0;D4;+0:9](-[C;D1;H3:10])(-[CH3;D1;+0:7])-[CH2;D2;+0:3]-[CH2;D2;+0:2]-[C;D1;H3:1] | null | [] | 50 | CELSIUS | null | null | An 80 mL Fischer-Porter high pressure bottle was charged with tetramethyldisiloxane (10.0 g), toluene (10.0 g) and Wilkinson's catalyst ((PPh3)3RhCl, 40 ppm), stirred and brought to 50° C. The bottle was attached to a manifold and pressurized with propylene (40 psig) and maintained at 50° C. for 2 h. The pressure was v... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl.Silyl protective group | Silyl protective group | null | null | null | null | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Cl-].[Rh] | 50 | null | C=CC.C[SiH2]O[Si](C)(C)C>C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Cl-].[Rh]>CCC[Si](C)(C)O[SiH](C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c5c287dd7b134f45bb78154a1dee8a69 | CC(C)(C)[Si](C)(C)Cl.C[SiH](C)Cl.O>>C[SiH](C)O[Si](C)(C)C(C)(C)C | O.C[SiH](Cl)C.[Si](C)(C)(C(C)(C)C)Cl.O>>C(C)(C)(C)[Si](O[SiH](C)C)(C)C | Cl[Si:5]([CH3:6])([CH3:7])[C:8]([CH3:9])([CH3:10])[CH3:11].Cl[SiH:2]([CH3:1])[CH3:3].[OH2:4]>>[CH3:1][SiH:2]([CH3:3])[O:4][Si:5]([CH3:6])([CH3:7])[C:8]([CH3:9])([CH3:10])[CH3:11] | CC(C)(C)[Si](C)(C)Cl.C[SiH](C)Cl.O | C[SiH](C)O[Si](C)(C)C(C)(C)C | null | null | C(C)(C)OC(C)C | Protection | OtherReaction | bcb384be6de101a88c51c45266569e6728cab9c6042ed1ac123bd15419519cd8 | d3939d5b137968db9e591134356fa8e55d322b5352280788afd540e031d3a866 | null | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].Cl-[SiH;D3;+0:8](-[C;D1;H3:9])-[C;D1;H3:10].[OH2;D0;+0:11]>>[C;D1;H3:5]-[C:4](-[C;D1;H3:6])(-[C;D1;H3:7])-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[O;H0;D2;+0:11]-[SiH;D3;+0:8](-[C;D1;H3:9])-[C;D1;H3:10] | null | [] | 32.5 | CELSIUS | null | null | A 1 L round bottom flask was charged with water (95 g) and diisopropyl ether (50 g) and stirred. A solution of tert-butyldimethylsilyl chloride (39.5 g) in isopropyl ether (50 g) was charged to an addition funnel, and added dropwise to the water/IPE mixture at a rate to maintain the reaction temperature between 30-35° ... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | TMS ether protective group | null | null | null | HCl | C(C)(C)OC(C)C | 32.5 | null | CC(C)(C)[Si](C)(C)Cl.C[SiH](C)Cl.O>C(C)(C)OC(C)C>C[SiH](C)O[Si](C)(C)C(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d454e0aadbda429e85a9206ac6fc1e6f | BrBr.c1ccc(C2CC2)cc1>>Brc1ccc(C2CC2)cc1 | OS(=O)[O-].[Na+].BrBr.C1(CC1)C1=CC=CC=C1.C(C)(=O)[O-].[Na+]>>C1(CC1)C1=CC=C(C=C1)Br | Br[Br:1].[cH:2]1[cH:3][cH:4][c:5]([CH:6]2[CH2:7][CH2:8]2)[cH:9][cH:10]1>>[Br:1][c:2]1[cH:3][cH:4][c:5]([CH:6]2[CH2:7][CH2:8]2)[cH:9][cH:10]1 | BrBr.c1ccc(C2CC2)cc1 | Brc1ccc(C2CC2)cc1 | null | null | O.C(C)(=O)O | Functional Group Interconversion | Bromination | f6effe61353895b318215d8bd9b6bb1105cafbf7be8c217d748df587260b32c3 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc(C2CC2)cc1 | Br-[Br;H0;D1;+0:1].[c:2]:[c:3]:[cH;D2;+0:4]:[c:5]:[c:6]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:3]:[c:2] | 21 | [{"value": 21.0, "product": "C1(CC1)C1=CC=C(C=C1)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 21.0, "product": "C1(CC1)C1=CC=C(C=C1)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | Cyclopropyl benzene (48.5 g, 410 mmol), glacial acetic acid (510 mL), and sodium acetate (38.9 g, 474 mmol) were added to a round bottomed flask. The flask was cooled in an ice-water bath. A solution of bromine (66.3 g, 414 mmol) dissolved in 105 mL of acetic acid was added dropwise over 90 min. The reaction mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CC1 | HBr | O.C(C)(=O)O | null | 5 | BrBr.c1ccc(C2CC2)cc1>O.C(C)(=O)O>Brc1ccc(C2CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9116056894ee47a3b743e195d1a7d4bd | O=S(=O)(Cl)c1ccc(C2CC2)cc1.[F-]>>O=S(=O)(F)c1ccc(C2CC2)cc1 | C1(CC1)C1=CC=C(C=C1)S(=O)(=O)Cl.[F-].[K+]>>C1(CC1)C1=CC=C(C=C1)S(=O)(=O)F | Cl[S:2](=[O:1])(=[O:3])[c:5]1[cH:6][cH:7][c:8]([CH:9]2[CH2:10][CH2:11]2)[cH:12][cH:13]1.[F-:4]>>[O:1]=[S:2](=[O:3])([F:4])[c:5]1[cH:6][cH:7][c:8]([CH:9]2[CH2:10][CH2:11]2)[cH:12][cH:13]1 | O=S(=O)(Cl)c1ccc(C2CC2)cc1.[F-] | O=S(=O)(F)c1ccc(C2CC2)cc1 | null | null | O.CC(=O)C.CCOC(=O)C | Functional Group Interconversion | OtherReaction | 1a5adee7f1ba8844d3aeea23793c6ed559c5770364925cb0ebd2c7a72ae17659 | 100ecb262b71c25deadc3940d6f3c2c0e7443b2546e5e1649d38d873195b4540 | c1ccc(C2CC2)cc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[F-;H0;D0:7]>>[F;H0;D1;+0:7]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 97 | [{"value": 97.0, "product": "C1(CC1)C1=CC=C(C=C1)S(=O)(=O)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.7, "product": "C1(CC1)C1=CC=C(C=C1)S(=O)(=O)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Crude compound 45 (13.3 g) was dissolved in 200 mL of acetone and 60 mL of water. Potassium fluoride (7.12 g, 122 mmol) was added and the reaction mixture was stirred overnight at rt. The reaction mixture was diluted with EtOAc and washed with water. The organic layer was dried with Na2SO4, filtered, and concentrated t... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | Sulfonyl halide | null | null | c1ccccc1.C1CC1 | Other | O.CC(=O)C.CCOC(=O)C | null | 8 | O=S(=O)(Cl)c1ccc(C2CC2)cc1.[F-]>O.CC(=O)C.CCOC(=O)C>O=S(=O)(F)c1ccc(C2CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-28df4cf85a8944b3854f43b6c60da1fe | CC(=O)c1ccncc1.NN.O=CC(=O)O>>O=c1ccc(-c2ccncc2)n[nH]1 | C(C)(=O)C1=CC=NC=C1.C([O-])([O-])=O.[K+].[K+].O.C(C=O)(=O)O.C(=O)([O-])[O-].[K+].[K+].O.NN>>N1=CC=C(C=C1)C=1C=CC(NN1)=O | O=[C:5]([CH3:4])[c:6]1[cH:7][cH:8][n:9][cH:10][cH:11]1.[NH2:12][NH2:13].O=[CH:3][C:2](O)=[O:1]>>[O:1]=[c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][n:9][cH:10][cH:11]2)[n:12][nH:13]1 | CC(=O)c1ccncc1.NN.O=CC(=O)O | O=c1ccc(-c2ccncc2)n[nH]1 | null | null | O.C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 0461b2f03bfc59a40676cd766082d1f571986553f759b05431b650a71f0fe88c | 87635d623d9cacd54865f4e9739e35f5fc1294b1eab6c4ff3e83b38d330e008c | O=c1ccc(-c2ccncc2)n[nH]1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D2;+0:3]=O.O=[C;H0;D3;+0:4](-[CH3;D1;+0:5])-[c;H0;D3;+0:6]1:[c:7]:[c:8]:[#7;a:9]:[c:10]:[c:11]:1.[NH2;D1;+0:12]-[NH2;D1;+0:13]>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[cH;D2;+0:3]:[cH;D2;+0:5]:[c;H0;D3;+0:4](-[c;H0;D3;+0:6]2:[c:7]:[c:8]:[#7;a:9]:[c:10]:[c:11]:2):[n;H0;D2;+0:12]:[nH;D2;+0:13]:1 | 64 | [{"value": 64.0, "product": "N1=CC=C(C=C1)C=1C=CC(NN1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | 99.5 g 4-Acetylpyridine is added to a cold (10° C.) solution of 222.4 potassium carbonate and 76.3 glyoxylic acid monohydrate in 1 L of water and the solution stirred at room temperature for 2.5 h. After cooling in to 0° C., 325 ml of acetic acid are added followed by 58.8 ml hydrazine hydrate, and the resulting soluti... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Aldehyde.Carboxylic acid.Ketone | null | null | c1cccnn1 | c1cccnn1.c1ccncc1 | HO- | O.C(C)(=O)O | null | 2.5 | CC(=O)c1ccncc1.NN.O=CC(=O)O>O.C(C)(=O)O>O=c1ccc(-c2ccncc2)n[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-df293d8948ca4d669724f7c80cc987c5 | O=P(Cl)(Cl)Cl.O=c1ccc(-c2ccncc2)n[nH]1>>Clc1ccc(-c2ccncc2)nn1 | N1=CC=C(C=C1)C=1C=CC(NN1)=O.P(=O)(Cl)(Cl)Cl>>ClC=1N=NC(=CC1)C1=CC=NC=C1 | O=P(Cl)(Cl)[Cl:1].O=[c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][n:9][cH:10][cH:11]2)[n:12][nH:13]1>>[Cl:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][n:9][cH:10][cH:11]2)[n:12][n:13]1 | O=P(Cl)(Cl)Cl.O=c1ccc(-c2ccncc2)n[nH]1 | Clc1ccc(-c2ccncc2)nn1 | null | null | null | Functional Group Interconversion | OtherReaction | 980c777204deda72a9af5dde6575971b5f1222eda5e63e2dd187b0b667e1d6d9 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1cnnc(-c2ccncc2)c1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[c:3]:[c:4]:[c:5]:[#7;a:6]:[nH;D2;+0:7]:1>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[c:5]:[#7;a:6]:[n;H0;D2;+0:7]:1 | 64.6 | [{"value": 64.6, "product": "ClC=1N=NC(=CC1)C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 1 | HOUR | 75.6 g 6-Pyridin-4-yl-2H-pyridazin-3-one is added in small portions to 234.5 g phosphorus oxychloride and the resulting mixture is stirred for 1 h at 100° C. Diluting into ice cold water, adjusting the pH 7 with aqueous sodium hydroxide and extraction with dichloromethane yielded 54 g 3-Chloro-6-pyridin-4-yl-pyridazine... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1cccnn1 | c1ccnnc1 | c1ccnnc1.c1ccncc1 | HCl | null | 100 | 1 | O=P(Cl)(Cl)Cl.O=c1ccc(-c2ccncc2)n[nH]1>>Clc1ccc(-c2ccncc2)nn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-62fd159e83e5416fbdff63e700088ba2 | C[O-].Clc1ccc(-c2ccncc2)nn1>>COc1ccc(-c2ccncc2)nn1 | C[O-].[Na+].ClC=1N=NC(=CC1)C1=CC=NC=C1>>COC=1N=NC(=CC1)C1=CC=NC=C1 | [CH3:1][O-:2].Cl[c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][n:10][cH:11][cH:12]2)[n:13][n:14]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][n:10][cH:11][cH:12]2)[n:13][n:14]1 | C[O-].Clc1ccc(-c2ccncc2)nn1 | COc1ccc(-c2ccncc2)nn1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | a9b48706c0031de50054078adf178cdb9c97933ae9a69eb837163dea0dd09084 | 51fd03eb6a688046e417b9ed09ea0e72062396d005af1318b9b5f376a97da959 | c1cnnc(-c2ccncc2)c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.[C;D1;H3:7]-[O-;H0;D1:8]>>[C;D1;H3:7]-[O;H0;D2;+0:8]-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1 | null | [] | null | null | null | null | 63 ml of a 32% sodium methoxide solution in methanol are added to a solution of 57 g 3-Chloro-6-pyridin-4-yl-pyridazine in methanol, and the reaction mixture is stirred under reflux for 1.5 h. The solvent is removed under reduced pressure, the residue suspended in 0.7 L water and the pH adjusted to 7. Extraction with d... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Ether | c1ccnnc1 | c1ccnnc1 | c1ccnnc1.c1ccncc1 | Other | CO | null | null | C[O-].Clc1ccc(-c2ccncc2)nn1>CO>COc1ccc(-c2ccncc2)nn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8abab3a4ad8a47a697141fbdebc2189e | COc1ccc(-c2ccncc2)nn1.II>>COc1nnc(-c2ccncc2)cc1I | C(CCC)[Li].CC1(NC(CCC1)(C)C)C.COC=1N=NC(=CC1)C1=CC=NC=C1.II>>IC1=C(N=NC(=C1)C1=CC=NC=C1)OC | [CH3:1][O:2][c:3]1[n:4][n:5][c:6](-[c:7]2[cH:8][cH:9][n:10][cH:11][cH:12]2)[cH:13][cH:14]1.I[I:15]>>[CH3:1][O:2][c:3]1[n:4][n:5][c:6](-[c:7]2[cH:8][cH:9][n:10][cH:11][cH:12]2)[cH:13][c:14]1[I:15] | COc1ccc(-c2ccncc2)nn1.II | COc1nnc(-c2ccncc2)cc1I | null | null | CCCCCC.C1CCOC1 | Functional Group Interconversion | OtherReaction | 3b22a5d23572bfe9ad1502a182eb9a0357f308a16eb4f4f5e1618044bed6ab38 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1cnnc(-c2ccncc2)c1 | I-[I;H0;D1;+0:1].[#8:2]-[c:3]1:[#7;a:4]:[#7;a:5]:[c:6](-[c:7]):[c:8]:[cH;D2;+0:9]:1>>[#8:2]-[c:3]1:[#7;a:4]:[#7;a:5]:[c:6](-[c:7]):[c:8]:[c;H0;D3;+0:9]:1-[I;H0;D1;+0:1] | 76.9 | [{"value": 76.9, "product": "IC1=C(N=NC(=C1)C1=CC=NC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | 45 ml 1.6M solution of n-Butyllithium in hexane are added at −30° C. to a 10.2 g 2,2,6,6-tetramethylpiperidine in 100 ml THF, and the mixture is stirred at 0° C. for 30 min. After cooling to −75° C., 11.2 g 3-Methoxy-6-pyridin-4-yl-pyridazine dissolved 300 ml THF are added, and the solution is stirred at −75° C. for 35... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccnnc1 | c1ccnnc1 | c1ccnnc1.c1ccncc1 | HI | CCCCCC.C1CCOC1 | 0 | 0.5 | COc1ccc(-c2ccncc2)nn1.II>CCCCCC.C1CCOC1>COc1nnc(-c2ccncc2)cc1I |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9c2f5754bafc4404a3db8a4e1aef1435 | CC(C)(C)OC(=O)n1c(B(O)O)cc2ccccc21.COc1nnc(-c2ccncc2)cc1I>>COc1nnc(-c2ccncc2)cc1-c1cc2ccccc2n1C(=O)OC(C)(C)C | IC1=C(N=NC(=C1)C1=CC=NC=C1)OC.C(C)(C)(C)OC(=O)N1C(=CC2=CC=CC=C12)B(O)O.C([O-])([O-])=O.[K+].[K+].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>C(C)(C)(C)OC(=O)N1C(=CC2=CC=CC=C12)C1=C(N=NC(=C1)C1=CC=NC=C1)OC | OB(O)[c:15]1[cH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]2[n:23]1[C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30].I[c:14]1[c:3]([O:2][CH3:1])[n:4][n:5][c:6](-[c:7]2[cH:8][cH:9][n:10][cH:11][cH:12]2)[cH:13]1>>[CH3:1][O:2][c:3]1[n:4][n:5][c:6](-[c:7]2[cH:8][cH:9][n:10][cH:11][cH:12]2)[cH:13][c:14]1-[c:15]1[cH:1... | CC(C)(C)OC(=O)n1c(B(O)O)cc2ccccc21.COc1nnc(-c2ccncc2)cc1I | COc1nnc(-c2ccncc2)cc1-c1cc2ccccc2n1C(=O)OC(C)(C)C | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | O.COCCOC.C(C)(=O)OCC | C-C Coupling | Suzuki coupling with boronic acids | 1825c39cd9e32be09658a13a21b34a56b6f1ce71f57a969c757b7ba9a84ebe00 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc2[nH]c(-c3cnnc(-c4ccncc4)c3)cc2c1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]):[#7;a:5]:[#7;a:6]:[c:7]:1-[#8:8].O-B(-O)-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[c:12]:[#7;a:13]:1-[C:14](=[O;D1;H0:15])-[#8:16]-[C:17](-[C;D1;H3:18])(-[C;D1;H3:19])-[C;D1;H3:20]>>[#8:8]-[c:7]1:[#7;a:6]:[#7;a:5]:[c:3](-[c:4]):[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[c:12]:[#7;a... | null | [] | null | null | null | null | Argon is passed for 30 min through a suspension of 55 mg 4-Iodo-3-methoxy-6-pyridin-4-yl-pyridazine, 55 mg 1-(tert-butoxycarbonyl)indole-2-boronic acid, 53.5 mg potassium carbonate, and 18.5 mg triphenylphosphine in 0.8 ml DME and 0.7 ml water. 4 mg palladium (II) acetate is added, and the mixture is stirred under refl... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc2ccccc2[nH]1.c1ccnnc1 | c1ccnnc1.c1cc2ccccc2[nH]1 | c1ccnnc1.c1ccncc1.c1cc2ccccc2[nH]1 | HI.B | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].O.COCCOC.C(C)(=O)OCC | null | null | CC(C)(C)OC(=O)n1c(B(O)O)cc2ccccc21.COc1nnc(-c2ccncc2)cc1I>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].O.COCCOC.C(C)(=O)OCC>COc1nnc(-c2ccncc2)cc1-c1cc2ccccc2n1C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b550d42f4a41483788e567e509065321 | COc1nnc(-c2ccncc2)cc1-c1cc2ccccc2n1C(=O)OC(C)(C)C>>O=c1[nH]nc(-c2ccncc2)cc1-c1cc2ccccc2[nH]1 | Cl.C(C)(C)(C)OC(=O)N1C(=CC2=CC=CC=C12)C1=C(N=NC(=C1)C1=CC=NC=C1)OC.C[Si](Cl)(C)C.CN(C)C=O.O>>N1C(=CC2=CC=CC=C12)C=1C(NN=C(C1)C1=CC=NC=C1)=O | CC(C)(C)OC(=O)[n:22]1[c:14](-[c:13]2[c:2]([O:1]C)[n:3][n:4][c:5](-[c:6]3[cH:7][cH:8][n:9][cH:10][cH:11]3)[cH:12]2)[cH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]21>>[O:1]=[c:2]1[nH:3][n:4][c:5](-[c:6]2[cH:7][cH:8][n:9][cH:10][cH:11]2)[cH:12][c:13]1-[c:14]1[cH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[nH:22]1 | COc1nnc(-c2ccncc2)cc1-c1cc2ccccc2n1C(=O)OC(C)(C)C | O=c1[nH]nc(-c2ccncc2)cc1-c1cc2ccccc2[nH]1 | null | null | O1CCOCC1.C(C)#N | Functional Group Interconversion | OtherReaction | ccff9e96bdfd7c95ea90e5e92eb38ee503eb19e38ebb19293d7570ec24d3836c | e4c2437726be227f3a4589d2c6c79cc20b165fa11361f93621036c026b9ea7bf | O=c1[nH]nc(-c2ccncc2)cc1-c1cc2ccccc2[nH]1 | C-[O;H0;D2;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[#7;a:4]:[c:5]:[c:6]:[c:7]:1-[c:8]1:[c:9]:[c:10]:[c:11](:[c:12]):[n;H0;D3;+0:13]:1-C(=O)-O-C(-C)(-C)-C>>[O;H0;D1;+0:1]=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[#7;a:4]:[c:5]:[c:6]:[c:7]:1-[c:8]1:[c:9]:[c:10]:[c:11](:[c:12]):[nH;D2;+0:13]:1 | 25.1 | [{"value": 25.1, "product": "N1C(=CC2=CC=CC=C12)C=1C(NN=C(C1)C1=CC=NC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 2 | HOUR | 25 mg of 2-(3-Methoxy-6-pyridin-4-yl-pyridazin-4-yl) -indole-1-carboxylic acid tert-butyl ester, 7.4 mg trimethylchlorosilane and 11.3 mg KI dissolved in 1 ml of acetonitrile are stirred for 2 h at 60° C. Subsequently, 0.5 ml of a 4N solution of hydrochloric acid in dioxane is added and stirred for 2 h at room temperat... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Boc | null | c1ccnnc1.c1cc2ccccc2[nH]1 | c1cnncc1.c1ccc2[nH]ccc2c1 | c1cnncc1.c1ccncc1.c1ccc2[nH]ccc2c1 | HO- | O1CCOCC1.C(C)#N | 60 | 2 | COc1nnc(-c2ccncc2)cc1-c1cc2ccccc2n1C(=O)OC(C)(C)C>O1CCOCC1.C(C)#N>O=c1[nH]nc(-c2ccncc2)cc1-c1cc2ccccc2[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-28d11d416310459daff1279f034bef16 | CC(C)(C)OC(=O)n1c(B(O)O)cc2ccccc21.COc1nnc(Cl)cc1I>>COc1nnc(Cl)cc1-c1cc2ccccc2n1C(=O)OC(C)(C)C | ClC1=CC(=C(N=N1)OC)I.C(C)(C)(C)OC(=O)N1C(=CC2=CC=CC=C12)B(O)O.C([O-])([O-])=O.[K+].[K+].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>C(C)(C)(C)OC(=O)N1C(=CC2=CC=CC=C12)C1=C(N=NC(=C1)Cl)OC | OB(O)[c:10]1[cH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[n:18]1[C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25].I[c:9]1[c:3]([O:2][CH3:1])[n:4][n:5][c:6]([Cl:7])[cH:8]1>>[CH3:1][O:2][c:3]1[n:4][n:5][c:6]([Cl:7])[cH:8][c:9]1-[c:10]1[cH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[n:18]1[C:19](=[O:20])[O:21]... | CC(C)(C)OC(=O)n1c(B(O)O)cc2ccccc21.COc1nnc(Cl)cc1I | COc1nnc(Cl)cc1-c1cc2ccccc2n1C(=O)OC(C)(C)C | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | O.COCCOC.C(C)(=O)OCC | C-C Coupling | Suzuki coupling with boronic acids | 1825c39cd9e32be09658a13a21b34a56b6f1ce71f57a969c757b7ba9a84ebe00 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc2[nH]c(-c3ccnnc3)cc2c1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[#7;a:6]:[c:7]:1-[#8:8].O-B(-O)-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[c:12]:[#7;a:13]:1-[C:14](=[O;D1;H0:15])-[#8:16]-[C:17](-[C;D1;H3:18])(-[C;D1;H3:19])-[C;D1;H3:20]>>[#8:8]-[c:7]1:[#7;a:6]:[#7;a:5]:[c:3](-[Cl;D1;H0:4]):[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:9]1:[c:10]:[c:11... | null | [] | null | null | null | null | Argon is passed for 30 min through a suspension of 135 mg 6-Chloro-4-iodo-3-methoxy-pyridazine, 130.5 mg 1-(tert-butoxycarbonyl)indole-2-boronic acid, 152 mg potassium carbonate, and 52.5 mg triphenylphosphine in 2.2 ml DME and 1.1 ml water. 11.2 mg palladium (II) acetate is added, and the mixture is stirred under refl... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc2ccccc2[nH]1.c1ccnnc1 | c1ccnnc1.c1cc2ccccc2[nH]1 | c1ccnnc1.c1cc2ccccc2[nH]1 | HI.B | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].O.COCCOC.C(C)(=O)OCC | null | null | CC(C)(C)OC(=O)n1c(B(O)O)cc2ccccc21.COc1nnc(Cl)cc1I>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].O.COCCOC.C(C)(=O)OCC>COc1nnc(Cl)cc1-c1cc2ccccc2n1C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-47393936c874421891c1b4b0bc535d00 | CC(C)OB1OC(C)(C)C(C)(C)O1.Cc1cn(C(=O)OC(C)(C)C)c2ccccc12>>Cc1c(B2OC(C)(C)C(C)(C)O2)n(C(=O)OC(C)(C)C)c2ccccc12 | C(C)(C)(C)OC(=O)N1C=C(C2=CC=CC=C12)C.[Li+].CC(C)[N-]C(C)C.C(C)(C)OB1OC(C(O1)(C)C)(C)C>>C(C)(C)(C)OC(=O)N1C(=C(C2=CC=CC=C12)C)B1OC(C(O1)(C)C)(C)C | CC(C)O[B:4]1[O:5][C:6]([CH3:7])([CH3:8])[C:9]([CH3:10])([CH3:11])[O:12]1.[CH3:1][c:2]1[cH:3][n:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[c:21]2[cH:22][cH:23][cH:24][cH:25][c:26]12>>[CH3:1][c:2]1[c:3]([B:4]2[O:5][C:6]([CH3:7])([CH3:8])[C:9]([CH3:10])([CH3:11])[O:12]2)[n:13]([C:14](=[O:15])[O:16][C:17]... | CC(C)OB1OC(C)(C)C(C)(C)O1.Cc1cn(C(=O)OC(C)(C)C)c2ccccc12 | Cc1c(B2OC(C)(C)C(C)(C)O2)n(C(=O)OC(C)(C)C)c2ccccc12 | null | null | O1CCCC1.C1CCOC1.CCCCCC | Functional Group Interconversion | OtherReaction | 6d7c7d3bd6b2a5cfde60b017fe21925e0baa18667a55bca89303f87003bc482b | 55b2480301cea859d1218f23e11281559f3dfc2ef4b9f2ac7f38d4293c2fe6cc | c1ccc2[nH]c(B3OCCO3)cc2c1 | C-C(-C)-O-[B;H0;D3;+0:1]1-[#8:2]-[C:3]-[C:4]-[#8:5]-1.[C;D1;H3:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[#8:10]-[C:11](=[O;D1;H0:12])-[#7;a:13]1:[c:14]:[c:15]:[c:16](-[C;D1;H3:17]):[cH;D2;+0:18]:1>>[C;D1;H3:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[#8:10]-[C:11](=[O;D1;H0:12])-[#7;a:13]1:[c:14]:[c:15]:[c:16](-[C;D1;H3:17]):[c;... | null | [] | 0 | CELSIUS | 30 | MINUTE | To a solution of 462 mg 3-Methyl-indole-1-carboxylic acid tert-butyl ester in 2.5 ml anhydrous tetrahydrofuran at −78° C. under argon is added 1.2 ml of a 2M LDA solution in THF/hexane and stirred at 0° C. for 30 min to complete the deprotonation. The reaction mixture is cooled to −78° C., 0.6 ml 2-Isopropoxy-4,4,5,5-t... | 10.6084/m9.figshare.5104873.v1 | null | null | Boronic ester | [B]1OCCO1.c1c[nH]c2ccccc12 | [B]1OCCO1.c1cc2ccccc2[nH]1 | [B]1OCCO1.c1cc2ccccc2[nH]1 | HO- | O1CCCC1.C1CCOC1.CCCCCC | 0 | 0.5 | CC(C)OB1OC(C)(C)C(C)(C)O1.Cc1cn(C(=O)OC(C)(C)C)c2ccccc12>O1CCCC1.C1CCOC1.CCCCCC>Cc1c(B2OC(C)(C)C(C)(C)O2)n(C(=O)OC(C)(C)C)c2ccccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ea2469830b4c4d03baee311161473058 | COc1nnc(-c2ccncc2)cc1I.Cc1c(B2OC(C)(C)C(C)(C)O2)n(C(=O)OC(C)(C)C)c2ccccc12>>COc1nnc(-c2ccncc2)cc1-c1c(C)c2ccccc2n1C(=O)OC(C)(C)C | IC1=C(N=NC(=C1)C1=CC=NC=C1)OC.C(C)(C)(C)OC(=O)N1C(=C(C2=CC=CC=C12)C)B1OC(C(O1)(C)C)(C)C.C([O-])([O-])=O.[K+].[K+].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>C(C)(C)(C)OC(=O)N1C(=C(C2=CC=CC=C12)C)C1=C(N=NC(=C1)C1=CC=NC=C1)OC | I[c:14]1[c:3]([O:2][CH3:1])[n:4][n:5][c:6](-[c:7]2[cH:8][cH:9][n:10][cH:11][cH:12]2)[cH:13]1.CC1(C)OB([c:15]2[c:16]([CH3:17])[c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]3[n:24]2[C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])OC1(C)C>>[CH3:1][O:2][c:3]1[n:4][n:5][c:6](-[c:7]2[cH:8][cH:9][n:10][cH:11][cH:12]2)[cH:13... | COc1nnc(-c2ccncc2)cc1I.Cc1c(B2OC(C)(C)C(C)(C)O2)n(C(=O)OC(C)(C)C)c2ccccc12 | COc1nnc(-c2ccncc2)cc1-c1c(C)c2ccccc2n1C(=O)OC(C)(C)C | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | O.COCCOC.C(C)(=O)OCC | C-C Coupling | Suzuki coupling with boronic esters | 950d74e7d32747b9e96a82a5735570544e464a4aae937bd81248abdfc2ab46de | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | c1ccc2[nH]c(-c3cnnc(-c4ccncc4)c3)cc2c1 | C-C1(-C)-O-B(-[c;H0;D3;+0:1]2:[#7;a:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6](-[C;D1;H3:7])(-[C;D1;H3:8])-[C;D1;H3:9]):[c:10]:[c:11]:[c:12]:2-[C;D1;H3:13])-O-C-1(-C)-C.I-[c;H0;D3;+0:14]1:[c:15]:[c:16](-[c:17]):[#7;a:18]:[#7;a:19]:[c:20]:1-[#8:21]>>[#8:21]-[c:20]1:[#7;a:19]:[#7;a:18]:[c:16](-[c:17]):[c:15]:[c;H0;D3;+0:14]:1-... | null | [] | null | null | null | null | Argon is passed for 30 min through a suspension of 333 mg 4-Iodo-3-methoxy-6-pyridin-4-yl-pyridazine, 380 mg 3-Methyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-indole-1-carb-oxylic acid tert-butyl ester, 294 mg potassium carbonate, and 111.6 mg triphenylphosphine in 4.8 ml DME and 2.4 ml water. 24 mg palladium (... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | c1ccnnc1.B1OCCO1.c1cc2ccccc2[nH]1 | c1ccnnc1.c1cc2ccccc2[nH]1 | c1ccnnc1.c1ccncc1.c1cc2ccccc2[nH]1 | HI.B | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].O.COCCOC.C(C)(=O)OCC | null | null | COc1nnc(-c2ccncc2)cc1I.Cc1c(B2OC(C)(C)C(C)(C)O2)n(C(=O)OC(C)(C)C)c2ccccc12>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].O.COCCOC.C(C)(=O)OCC>COc1nnc(-c2ccncc2)cc1-c1c(C)c2ccccc2n1C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-84e18a8e496b4d0886d03495ef54cd7d | COc1nnc(-c2ccncc2)cc1-c1c(C)c2ccccc2n1C(=O)OC(C)(C)C>>Cc1c(-c2cc(-c3ccncc3)n[nH]c2=O)[nH]c2ccccc12 | C(C)(C)(C)OC(=O)N1C(=C(C2=CC=CC=C12)C)C1=C(N=NC(=C1)C1=CC=NC=C1)OC.Cl>>CC1=C(NC2=CC=CC=C12)C=1C(NN=C(C1)C1=CC=NC=C1)=O | CC(C)(C)OC(=O)[n:17]1[c:3](-[c:4]2[cH:5][c:6](-[c:7]3[cH:8][cH:9][n:10][cH:11][cH:12]3)[n:13][n:14][c:15]2[O:16]C)[c:2]([CH3:1])[c:23]2[c:18]1[cH:19][cH:20][cH:21][cH:22]2>>[CH3:1][c:2]1[c:3](-[c:4]2[cH:5][c:6](-[c:7]3[cH:8][cH:9][n:10][cH:11][cH:12]3)[n:13][nH:14][c:15]2=[O:16])[nH:17][c:18]2[cH:19][cH:20][cH:21][cH:2... | COc1nnc(-c2ccncc2)cc1-c1c(C)c2ccccc2n1C(=O)OC(C)(C)C | Cc1c(-c2cc(-c3ccncc3)n[nH]c2=O)[nH]c2ccccc12 | null | null | [OH-].[Na+].C(C)O | Functional Group Interconversion | OtherReaction | ccff9e96bdfd7c95ea90e5e92eb38ee503eb19e38ebb19293d7570ec24d3836c | e4c2437726be227f3a4589d2c6c79cc20b165fa11361f93621036c026b9ea7bf | O=c1[nH]nc(-c2ccncc2)cc1-c1cc2ccccc2[nH]1 | C-[O;H0;D2;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[#7;a:4]:[c:5]:[c:6]:[c:7]:1-[c:8]1:[c:9]:[c:10]:[c:11](:[c:12]):[n;H0;D3;+0:13]:1-C(=O)-O-C(-C)(-C)-C>>[O;H0;D1;+0:1]=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[#7;a:4]:[c:5]:[c:6]:[c:7]:1-[c:8]1:[c:9]:[c:10]:[c:11](:[c:12]):[nH;D2;+0:13]:1 | 58.1 | [{"value": 58.1, "product": "CC1=C(NC2=CC=CC=C12)C=1C(NN=C(C1)C1=CC=NC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | null | null | 50 mg 2-(3-Methoxy-6-pyridin-4-yl-pyridazin-4-yl)-3-methyl-indole-1-carboxylic acid tert-butyl ester is dissolved in 0.75 ml ethanol and 0.75 ml 1N aqueous NaOH solution. The reaction mixture is stirred at 150° C. in microwave apparatus (200 W). The solution is neutralized by addition of 1N HCl, the solvent removed und... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Boc | null | c1ccnnc1.c1cc2ccccc2[nH]1 | c1cnncc1.c1ccc2[nH]ccc2c1 | c1cnncc1.c1ccncc1.c1ccc2[nH]ccc2c1 | HO- | [OH-].[Na+].C(C)O | 150 | null | COc1nnc(-c2ccncc2)cc1-c1c(C)c2ccccc2n1C(=O)OC(C)(C)C>[OH-].[Na+].C(C)O>Cc1c(-c2cc(-c3ccncc3)n[nH]c2=O)[nH]c2ccccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b41063aa5f564adfb8c58a590b17be0b | CC=O.COc1ccc(Cl)nn1>>COc1nnc(Cl)cc1C(C)O | Cl.C(C)=O.C(CCC)[Li].ClC=1N=NC(=CC1)OC.C([O-])(O)=O.[Na+].CC1(NC(CCC1)(C)C)C>>ClC1=CC(=C(N=N1)OC)C(C)O | [CH:10]([CH3:11])=[O:12].[CH3:1][O:2][c:3]1[n:4][n:5][c:6]([Cl:7])[cH:8][cH:9]1>>[CH3:1][O:2][c:3]1[n:4][n:5][c:6]([Cl:7])[cH:8][c:9]1[CH:10]([CH3:11])[OH:12] | CC=O.COc1ccc(Cl)nn1 | COc1nnc(Cl)cc1C(C)O | null | null | O1CCCC1.CCCCCC.C(C)O | C-C Coupling | OtherReaction | a27fffed4aaf6d2a30bf6b0df69ab017955ce9c7a44f21694f8a14adcbb193f6 | a7cae52d902b2812376f5459a7a8b7ead54e8ef31fd78982d2e99bec532613ba | c1ccnnc1 | [#8:1]-[c:2]1:[#7;a:3]:[#7;a:4]:[c:5](-[Cl;D1;H0:6]):[c:7]:[cH;D2;+0:8]:1.[C;D1;H3:9]-[CH;D2;+0:10]=[O;H0;D1;+0:11]>>[#8:1]-[c:2]1:[#7;a:3]:[#7;a:4]:[c:5](-[Cl;D1;H0:6]):[c:7]:[c;H0;D3;+0:8]:1-[CH;D3;+0:10](-[C;D1;H3:9])-[OH;D1;+0:11] | null | [] | 0 | CELSIUS | 30 | MINUTE | 47.7 ml of a 1.6M solution of n-Butyl lithium in hexane is added dropwise at −75° C. to 100 ml tetrahydrofuran followed by 12.9 ml 2,2,6,6-tetramethylpiperidine and the resulting solution is allowed to warm to 0° C. and stirred for 30 min. The solution is cooled to −75° C. and a solution of 5 g 3-chloro-6-methoxypyrida... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Secondary alcohol | c1ccnnc1 | c1ccnnc1 | c1ccnnc1 | null | O1CCCC1.CCCCCC.C(C)O | 0 | 0.5 | CC=O.COc1ccc(Cl)nn1>O1CCCC1.CCCCCC.C(C)O>COc1nnc(Cl)cc1C(C)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4e0a1926184942ec9626622b11249023 | COc1nnc(Cl)cc1C(C)O>>COc1nnc(Cl)cc1C(C)=O | ClC1=CC(=C(N=N1)OC)C(C)O>>ClC1=CC(=C(N=N1)OC)C(C)=O | [CH3:1][O:2][c:3]1[n:4][n:5][c:6]([Cl:7])[cH:8][c:9]1[CH:10]([CH3:11])[OH:12]>>[CH3:1][O:2][c:3]1[n:4][n:5][c:6]([Cl:7])[cH:8][c:9]1[C:10]([CH3:11])=[O:12] | COc1nnc(Cl)cc1C(C)O | COc1nnc(Cl)cc1C(C)=O | null | [O-2].[O-2].[Mn+4] | O1CCCC1 | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | c1ccnnc1 | [#8:1]-[c:2]1:[#7;a:3]:[#7;a:4]:[c:5]:[c:6]:[c:7]:1-[CH;D3;+0:8](-[C;D1;H3:9])-[OH;D1;+0:10]>>[#8:1]-[c:2]1:[#7;a:3]:[#7;a:4]:[c:5]:[c:6]:[c:7]:1-[C;H0;D3;+0:8](-[C;D1;H3:9])=[O;H0;D1;+0:10] | null | [] | null | null | 48 | HOUR | 3.85 g 1-(6-Chloro-3-methoxy-pyridazin-4-yl)-ethanol is dissolved in 300 ml tetrahydrofuran and 35.5 g of manganese dioxide is added. The reaction is stirred for 48 h at RT. Solids are removed by filtration, and the solvent is removed under reduced pressure. The product is purified and separated from 1-(3-chloro-6-meth... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | c1ccnnc1 | null | [O-2].[O-2].[Mn+4].O1CCCC1 | null | 48 | COc1nnc(Cl)cc1C(C)O>[O-2].[O-2].[Mn+4].O1CCCC1>COc1nnc(Cl)cc1C(C)=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-37ce4e5a8ef842b18b2e9b12bd3cff77 | COc1nnc(Cl)cc1C(C)=O.Cc1cc(B2OC(C)(C)C(C)(C)O2)cc(C)c1O>>COc1nnc(-c2cc(C)c(O)c(C)c2)cc1C(C)=O | CC1=C(C(=CC(=C1)B1OC(C(O1)(C)C)(C)C)C)O.C([O-])([O-])=O.[Na+].[Na+].ClC1=CC(=C(N=N1)OC)C(C)=O>>OC1=C(C=C(C=C1C)C1=CC(=C(N=N1)OC)C(C)=O)C | Cl[c:6]1[n:5][n:4][c:3]([O:2][CH3:1])[c:17]([C:18]([CH3:19])=[O:20])[cH:16]1.CC1(C)OB([c:7]2[cH:8][c:9]([CH3:10])[c:11]([OH:12])[c:13]([CH3:14])[cH:15]2)OC1(C)C>>[CH3:1][O:2][c:3]1[n:4][n:5][c:6](-[c:7]2[cH:8][c:9]([CH3:10])[c:11]([OH:12])[c:13]([CH3:14])[cH:15]2)[cH:16][c:17]1[C:18]([CH3:19])=[O:20] | COc1nnc(Cl)cc1C(C)=O.Cc1cc(B2OC(C)(C)C(C)(C)O2)cc(C)c1O | COc1nnc(-c2cc(C)c(O)c(C)c2)cc1C(C)=O | null | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | COCCOC | C-C Coupling | Suzuki coupling with boronic esters | 7d3abbda54e933df9ff9dc39c70f4c4ada1c268870f29590395c2cc6bed1dda1 | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | c1ccc(-c2cccnn2)cc1 | C-C1(-C)-O-B(-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-O-C-1(-C)-C.Cl-[c;H0;D3;+0:6]1:[#7;a:7]:[#7;a:8]:[c:9]:[c:10](-[C:11](-[C;D1;H3:12])=[O;D1;H0:13]):[c:14]:1>>[C;D1;H3:12]-[C:11](=[O;D1;H0:13])-[c:10]1:[c:14]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[#7;a:7]:[#7;a:8]:[c:9]:1 | null | [] | null | null | 5 | MINUTE | 250 mg of 1-(6-Chloro-3-methoxy-pyridazin-4-yl)-ethanone and 232 mg of tetrakis(triphenylphosphine) palladium (0) are dissolved in 5 ml DME and the solution is stirred for 5 min at RT under argon. 400 mg of 2,6-Dimethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol and 1.4 ml of a 2M aqueous solution of sodiu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | c1ccnnc1.B1OCCO1.c1ccccc1 | c1ccnnc1.c1ccccc1 | c1ccnnc1.c1ccccc1 | HCl.B | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.COCCOC | null | 0.083333 | COc1nnc(Cl)cc1C(C)=O.Cc1cc(B2OC(C)(C)C(C)(C)O2)cc(C)c1O>[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.COCCOC>COc1nnc(-c2cc(C)c(O)c(C)c2)cc1C(C)=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-752f5172a1dc4c88aa70e977aa30f488 | COc1nnc(-c2cc(C)c(O)c(C)c2)cc1C(C)=O.Nc1ccccc1Br>>COc1nnc(-c2cc(C)c(O)c(C)c2)cc1-c1cc2ccccc2[nH]1 | BrC1=C(N)C=CC=C1.S(=O)(=O)([O-])[O-].[Mg+2].OC1=C(C=C(C=C1C)C1=CC(=C(N=N1)OC)C(C)=O)C.C(C)(=O)O>>N1C(=CC2=CC=CC=C12)C=1C=C(N=NC1OC)C1=CC(=C(C(=C1)C)O)C | O=[C:18]([c:17]1[c:3]([O:2][CH3:1])[n:4][n:5][c:6](-[c:7]2[cH:8][c:9]([CH3:10])[c:11]([OH:12])[c:13]([CH3:14])[cH:15]2)[cH:16]1)[CH3:19].Br[c:20]1[cH:21][cH:22][cH:23][cH:24][c:25]1[NH2:26]>>[CH3:1][O:2][c:3]1[n:4][n:5][c:6](-[c:7]2[cH:8][c:9]([CH3:10])[c:11]([OH:12])[c:13]([CH3:14])[cH:15]2)[cH:16][c:17]1-[c:18]1[cH:1... | COc1nnc(-c2cc(C)c(O)c(C)c2)cc1C(C)=O.Nc1ccccc1Br | COc1nnc(-c2cc(C)c(O)c(C)c2)cc1-c1cc2ccccc2[nH]1 | null | null | CC(=O)N(C)C | Aromatic Heterocycle Formation | OtherReaction | 2aeebda70d28950751bcff9d93d27d409a496c19f9c9b9893349a271b234d219 | 4e13c013c1ec63cb4e4f791be1390f390c40f8fc080e4593325e7876241ac282 | c1ccc(-c2cc(-c3cc4ccccc4[nH]3)cnn2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[NH2;D1;+0:5]):[c:6].O=[C;H0;D3;+0:7](-[CH3;D1;+0:8])-[c;H0;D3;+0:9]1:[c:10]:[c:11](-[c:12]):[#7;a:13]:[#7;a:14]:[c:15]:1-[#8:16]>>[#8:16]-[c:15]1:[#7;a:14]:[#7;a:13]:[c:11](-[c:12]):[c:10]:[c;H0;D3;+0:9]:1-[c;H0;D3;+0:7]1:[cH;D2;+0:8]:[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:6]):[n... | null | [] | 140 | CELSIUS | null | null | 205 mg of 2-bromoaniline and 72 mg of anhydrous magnesium sulfate are suspended in 7 ml dimethylacetamide. 325 mg of 1-[6-(4-Hydroxy-3,5-dimethyl-phenyl)-3-methoxy-pyridazin-4-yl]-ethanone and 86.6 μl acetic acid are added and the reaction is degassed with argon. 330 mg of tripotassium phosphate and 61 mg of bis(tri-te... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Primary amine | null | c1ccccc1 | c1ccc2[nH]ccc2c1 | c1ccnnc1.c1ccccc1.c1ccc2[nH]ccc2c1 | HBr | CC(=O)N(C)C | 140 | null | COc1nnc(-c2cc(C)c(O)c(C)c2)cc1C(C)=O.Nc1ccccc1Br>CC(=O)N(C)C>COc1nnc(-c2cc(C)c(O)c(C)c2)cc1-c1cc2ccccc2[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7463c8b27b9b45fe987dd3e1d903dce1 | COc1nnc(-c2cc(C)c(O)c(C)c2)cc1-c1cc2ccccc2[nH]1>>Cc1cc(-c2cc(-c3cc4ccccc4[nH]3)c(=O)[nH]n2)cc(C)c1O | N1C(=CC2=CC=CC=C12)C=1C=C(N=NC1OC)C1=CC(=C(C(=C1)C)O)C.C[Si](C)(C)Cl.[I-].[K+].C[Si](C)(C)Cl.[I-].[K+]>>OC1=C(C=C(C=C1C)C=1C=C(C(NN1)=O)C=1NC2=CC=CC=C2C1)C | C[O:18][c:17]1[c:7](-[c:8]2[cH:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[nH:16]2)[cH:6][c:5](-[c:4]2[cH:3][c:2]([CH3:1])[c:24]([OH:25])[c:22]([CH3:23])[cH:21]2)[n:20][n:19]1>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][c:7](-[c:8]3[cH:9][c:10]4[cH:11][cH:12][cH:13][cH:14][c:15]4[nH:16]3)[c:17](=[O:18])[nH:19][n:20]2)[cH:... | COc1nnc(-c2cc(C)c(O)c(C)c2)cc1-c1cc2ccccc2[nH]1 | Cc1cc(-c2cc(-c3cc4ccccc4[nH]3)c(=O)[nH]n2)cc(C)c1O | null | null | C(C)#N.O | Miscellaneous | OtherReaction | 3a907fa62544f46964e2b473ab8a45caedf80503ce5e705ae3da44b55acc0eb2 | 291cad8b6dfbbd2c823b5c9d45efc37a166dc3454a9f151ac48cb357f4bc155f | O=c1[nH]nc(-c2ccccc2)cc1-c1cc2ccccc2[nH]1 | C-[O;H0;D2;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[#7;a:4]:[c:5]:[c:6]:[c:7]:1-[c:8]:[#7;a:9]>>[#7;a:9]:[c:8]-[c:7]1:[c:6]:[c:5]:[#7;a:4]:[nH;D2;+0:3]:[c;H0;D3;+0:2]:1=[O;H0;D1;+0:1] | null | [] | 80 | CELSIUS | 16 | HOUR | 100 mg of 4-[5-(1H-Indol-2-yl)-6-methoxy-pyridazin-3-yl]-2,6-dimethyl-phenol is suspended in 2 ml acetonitrile and 40 μl of trimethylsilyl chloride and 53 mg of potassium iodide are added. The solution is heated to 80° C. for 3h, then a further 120 μl of trimethylsilyl chloride and 159 mg of potassium iodide are added.... | 10.6084/m9.figshare.5104873.v1 | null | Ether | null | c1ccnnc1 | c1cnncc1 | c1ccccc1.c1cnncc1.c1ccc2[nH]ccc2c1 | Other | C(C)#N.O | 80 | 16 | COc1nnc(-c2cc(C)c(O)c(C)c2)cc1-c1cc2ccccc2[nH]1>C(C)#N.O>Cc1cc(-c2cc(-c3cc4ccccc4[nH]3)c(=O)[nH]n2)cc(C)c1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5c6a509c1e8d4e2fa4db8389032a13af | COc1nnc(-c2ccncc2)cc1-c1cc2ccccc2n1C(=O)OC(C)(C)C>>COc1nnc(-c2ccncc2)cc1-c1cc2ccccc2[nH]1 | C(C)(C)(C)OC(=O)N1C(=CC2=CC=CC=C12)C1=C(N=NC(=C1)C1=CC=NC=C1)OC.C(=O)(C(F)(F)F)O>>FC(C(=O)O)(F)F.COC=1N=NC(=CC1C=1NC2=CC=CC=C2C1)C1=CC=NC=C1 | CC(C)(C)OC(=O)[n:23]1[c:15](-[c:14]2[c:3]([O:2][CH3:1])[n:4][n:5][c:6](-[c:7]3[cH:8][cH:9][n:10][cH:11][cH:12]3)[cH:13]2)[cH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]21>>[CH3:1][O:2][c:3]1[n:4][n:5][c:6](-[c:7]2[cH:8][cH:9][n:10][cH:11][cH:12]2)[cH:13][c:14]1-[c:15]1[cH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]2[... | COc1nnc(-c2ccncc2)cc1-c1cc2ccccc2n1C(=O)OC(C)(C)C | COc1nnc(-c2ccncc2)cc1-c1cc2ccccc2[nH]1 | null | null | ClCCl | Reduction | Boc amine deprotection | eefd4487d640b2607d7a60d065f8822bc457add01d643b9dbf7d76d9b4bfeca6 | e1bf5a54b1f87284564f107662531aec2aff7de801e4606340967b38924afb28 | c1ccc2[nH]c(-c3cnnc(-c4ccncc4)c3)cc2c1 | C-C(-C)(-C)-O-C(=O)-[n;H0;D3;+0:1]1:[c:2](-[c:3]:[c:4]:[#7;a:5]):[c:6]:[c:7]:[c:8]:1:[c:9]>>[#7;a:5]:[c:4]:[c:3]-[c:2]1:[c:6]:[c:7]:[c:8](:[c:9]):[nH;D2;+0:1]:1 | null | [] | null | null | null | null | A solution of 5.5 g 2-(3-Methoxy-6-pyridin-4-yl-pyridazin-4-yl)-indole-1-carboxylic acid tert-butyl ester and 5 ml TFA in 10 ml dichloromethane stirred for 18 h at room temperature. The solvent is evaporated and the crude product purified by suspended in water and collecting the precipitate.
Conditions: See reaction.no... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Boc | null | c1cc2ccccc2[nH]1 | c1ccc2[nH]ccc2c1 | c1ccnnc1.c1ccncc1.c1ccc2[nH]ccc2c1 | HO- | ClCCl | null | null | COc1nnc(-c2ccncc2)cc1-c1cc2ccccc2n1C(=O)OC(C)(C)C>ClCCl>COc1nnc(-c2ccncc2)cc1-c1cc2ccccc2[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-df37e54e99184edb875ff4a1fcc24cfb | COc1nnc(-c2ccncc2)cc1-c1[nH]c2ccccc2c1I.OB(O)c1ccccc1>>COc1nnc(-c2ccncc2)cc1-c1[nH]c2ccccc2c1-c1ccccc1 | OC(=O)C(F)(F)F.IC1=C(NC2=CC=CC=C12)C1=C(N=NC(=C1)C1=CC=NC=C1)OC.C1(=CC=CC=C1)B(O)O.C([O-])([O-])=O.[K+].[K+].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>COC=1N=NC(=CC1C=1NC2=CC=CC=C2C1C1=CC=CC=C1)C1=CC=NC=C1 | I[c:23]1[c:15](-[c:14]2[c:3]([O:2][CH3:1])[n:4][n:5][c:6](-[c:7]3[cH:8][cH:9][n:10][cH:11][cH:12]3)[cH:13]2)[nH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]21.OB(O)[c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1>>[CH3:1][O:2][c:3]1[n:4][n:5][c:6](-[c:7]2[cH:8][cH:9][n:10][cH:11][cH:12]2)[cH:13][c:14]1-[c:15]1[nH:16][c:17]2... | COc1nnc(-c2ccncc2)cc1-c1[nH]c2ccccc2c1I.OB(O)c1ccccc1 | COc1nnc(-c2ccncc2)cc1-c1[nH]c2ccccc2c1-c1ccccc1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | O.COCCOC.C(C)(=O)OCC | C-C Coupling | Suzuki coupling with boronic acids | 42e21206f0250bb469664981cf521bd21ce6ff7bf8a8e9271f94397f7d3b79cb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2c(-c3cnnc(-c4ccncc4)c3)[nH]c3ccccc23)cc1 | I-[c;H0;D3;+0:1]1:[c:2](-[c:3]:[c:4]:[#7;a:5]):[#7;a:6]:[c:7](:[c:8]):[c:9]:1:[c:10].O-B(-O)-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]>>[#7;a:5]:[c:4]:[c:3]-[c:2]1:[#7;a:6]:[c:7](:[c:8]):[c:9](:[c:10]):[c;H0;D3;+0:1]:1-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15] | null | [] | null | null | null | null | Argon is passed for 30 min through a suspension of 270 mg 3-Iodo-2-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-1H-indole TFA salt, 73 mg phenylboronic acid, 220 mg potassium carbonate and 52.4 mg triphenylphosphine in 2 ml DME and 1 ml water. 11.2 mg palladium (II) acetate is added and the mixture stirred under reflux fo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccnnc1.c1ccncc1.c1ccc2[nH]ccc2c1.c1ccccc1 | HI.B | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].O.COCCOC.C(C)(=O)OCC | null | null | COc1nnc(-c2ccncc2)cc1-c1[nH]c2ccccc2c1I.OB(O)c1ccccc1>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].O.COCCOC.C(C)(=O)OCC>COc1nnc(-c2ccncc2)cc1-c1[nH]c2ccccc2c1-c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-babd983aec834ea392fb32d0044e7696 | COc1nnc(-c2ccncc2)cc1-c1[nH]c2ccccc2c1-c1ccccc1>>O=c1[nH]nc(-c2ccncc2)cc1-c1[nH]c2ccccc2c1-c1ccccc1 | COC=1N=NC(=CC1C=1NC2=CC=CC=C2C1C1=CC=CC=C1)C1=CC=NC=C1.C(C)#N.O.C(=O)O>>C1(=CC=CC=C1)C1=C(NC2=CC=CC=C12)C=1C(NN=C(C1)C1=CC=NC=C1)=O | C[O:1][c:2]1[n:3][n:4][c:5](-[c:6]2[cH:7][cH:8][n:9][cH:10][cH:11]2)[cH:12][c:13]1-[c:14]1[nH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[c:22]1-[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1>>[O:1]=[c:2]1[nH:3][n:4][c:5](-[c:6]2[cH:7][cH:8][n:9][cH:10][cH:11]2)[cH:12][c:13]1-[c:14]1[nH:15][c:16]2[cH:17][cH:18][cH:19][c... | COc1nnc(-c2ccncc2)cc1-c1[nH]c2ccccc2c1-c1ccccc1 | O=c1[nH]nc(-c2ccncc2)cc1-c1[nH]c2ccccc2c1-c1ccccc1 | null | null | [OH-].[Na+].C(C)O | Miscellaneous | OtherReaction | 3a907fa62544f46964e2b473ab8a45caedf80503ce5e705ae3da44b55acc0eb2 | 291cad8b6dfbbd2c823b5c9d45efc37a166dc3454a9f151ac48cb357f4bc155f | O=c1[nH]nc(-c2ccncc2)cc1-c1[nH]c2ccccc2c1-c1ccccc1 | C-[O;H0;D2;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[#7;a:4]:[c:5]:[c:6]:[c:7]:1-[c:8]:[#7;a:9]>>[#7;a:9]:[c:8]-[c:7]1:[c:6]:[c:5]:[#7;a:4]:[nH;D2;+0:3]:[c;H0;D3;+0:2]:1=[O;H0;D1;+0:1] | null | [] | 150 | CELSIUS | null | null | 63 mg 2-(3-Methoxy-6-pyridin-4-yl-pyridazin-4-yl)-3-phenyl-1H-indole is dissolved in 0.75 ml ethanol and 0.75 ml 1N aqueous NaOH solution. The reaction mixture is stirred at 150° C. in microwave apparatus (200 W). The reaction mixture is directly applied to HPLC chromatography to isolate the product (RP18 column, aceto... | 10.6084/m9.figshare.5104873.v1 | null | Ether | null | c1ccnnc1 | c1cnncc1 | c1cnncc1.c1ccncc1.c1ccc2[nH]ccc2c1.c1ccccc1 | Other | [OH-].[Na+].C(C)O | 150 | null | COc1nnc(-c2ccncc2)cc1-c1[nH]c2ccccc2c1-c1ccccc1>[OH-].[Na+].C(C)O>O=c1[nH]nc(-c2ccncc2)cc1-c1[nH]c2ccccc2c1-c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b5645a3c8db242f59d774cd41912d028 | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.COc1nnc(-c2ccncc2)cc1-c1[nH]c2ccccc2c1I>>C=Cc1c(-c2cc(-c3ccncc3)nnc2OC)[nH]c2ccccc12 | IC1=C(NC2=CC=CC=C12)C1=C(N=NC(=C1)C1=CC=NC=C1)OC.C(CCC)[Sn](C=C)(CCCC)CCCC.CCOC(=O)C.[F-].[K+]>>COC=1N=NC(=CC1C=1NC2=CC=CC=C2C1C=C)C1=CC=NC=C1 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH:2]=[CH2:1].I[c:3]1[c:4](-[c:5]2[cH:6][c:7](-[c:8]3[cH:9][cH:10][n:11][cH:12][cH:13]3)[n:14][n:15][c:16]2[O:17][CH3:18])[nH:19][c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]12>>[CH2:1]=[CH:2][c:3]1[c:4](-[c:5]2[cH:6][c:7](-[c:8]3[cH:9][cH:10][n:11][cH:12][cH:13]3)[n:14][n:15][c:16]2[O:17][... | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.COc1nnc(-c2ccncc2)cc1-c1[nH]c2ccccc2c1I | C=Cc1c(-c2cc(-c3ccncc3)nnc2OC)[nH]c2ccccc12 | null | [Cl-].C(C)[N+](CC)(CC)CC.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)C=O | C-C Coupling | Stille reaction_vinyl | f4ad649c74b7a6a35b0e84610492e238d5241d8eaf0ab45cca5db093924b7eac | ec03c739f58696d2a3659a73884744e1a490a20a587da6f115be382b663cf23d | c1ccc2[nH]c(-c3cnnc(-c4ccncc4)c3)cc2c1 | C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[CH;D2;+0:1]=[C;D1;H2:2].I-[c;H0;D3;+0:3]1:[c:4](:[c:5]):[c:6](:[c:7]):[#7;a:8]:[c:9]:1-[c:10]:[c:11]:[#7;a:12]>>[#7;a:12]:[c:11]:[c:10]-[c:9]1:[#7;a:8]:[c:6](:[c:7]):[c:4](:[c:5]):[c;H0;D3;+0:3]:1-[CH;D2;+0:1]=[C;D1;H2:2] | null | [] | 80 | CELSIUS | 40 | MINUTE | A mixture of 430 mg 3-Iodo-2-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-1H-indole, 490 mg tributyl(vinyl)tin, 165 mg tetraethylammonium-chloride and 35 mg bis(triphenylphosphine)palladium(II) chloride in DMF is stirred at 80° C. for 40 min. After cooling to room temperature, 15 ml aqueous potassium fluoride solution (30... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Vinyl.Tin | Vinyl | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccnnc1.c1ccncc1.c1ccc2[nH]ccc2c1 | HI.Sn | [Cl-].C(C)[N+](CC)(CC)CC.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)C=O | 80 | 0.666667 | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.COc1nnc(-c2ccncc2)cc1-c1[nH]c2ccccc2c1I>[Cl-].C(C)[N+](CC)(CC)CC.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)C=O>C=Cc1c(-c2cc(-c3ccncc3)nnc2OC)[nH]c2ccccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-33ec444488544a8ebe118ee0146cd0ef | C=CC1c2ccccc2NC1(CO)c1cc(-c2ccncc2)nnc1OC>>CCc1c(-c2cc(-c3ccncc3)nnc2OC)[nH]c2ccccc12 | COC=1N=NC(=CC1C1(NC2=CC=CC=C2C1C=C)CO)C1=CC=NC=C1>>C(C)C1=C(NC2=CC=CC=C12)C1=C(N=NC(=C1)C1=CC=NC=C1)OC | OC[C:4]1([c:5]2[cH:6][c:7](-[c:8]3[cH:9][cH:10][n:11][cH:12][cH:13]3)[n:14][n:15][c:16]2[O:17][CH3:18])[CH:3]([CH:2]=[CH2:1])[c:25]2[c:20]([cH:21][cH:22][cH:23][cH:24]2)[NH:19]1>>[CH3:1][CH2:2][c:3]1[c:4](-[c:5]2[cH:6][c:7](-[c:8]3[cH:9][cH:10][n:11][cH:12][cH:13]3)[n:14][n:15][c:16]2[O:17][CH3:18])[nH:19][c:20]2[cH:21... | C=CC1c2ccccc2NC1(CO)c1cc(-c2ccncc2)nnc1OC | CCc1c(-c2cc(-c3ccncc3)nnc2OC)[nH]c2ccccc12 | null | [Pd] | null | Functional Group Interconversion | OtherReaction | b6d4453beea49d45807241e91d8288d0f248f4f4d05bbfb442e2a8540fe98ed6 | b5345ac429e84e6be0df234cae5011cf4e71e4da6aa7f89ad313e9a0722024e2 | c1ccc2[nH]c(-c3cnnc(-c4ccncc4)c3)cc2c1 | O-C-[C;H0;D4;+0:1]1(-[c;H0;D3;+0:2]2:[c:3]:[c:4](-[c:5]):[#7;a:6]:[#7;a:7]:[c:8]:2-[#8:9])-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13](:[c:14])-[CH;D3;+0:15]-1-[CH;D2;+0:16]=[CH2;D1;+0:17]>>[#8:9]-[c:8]1:[#7;a:7]:[#7;a:6]:[c:4](-[c:5]):[c:3]:[c;H0;D3;+0:2]:1-[c;H0;D3;+0:1]1:[nH;D2;+0:10]:[c:11](:[c:12]):[c:13](:[c:14]):[c;H0;... | null | [] | null | null | 4 | HOUR | 12 mg Palladium, 10% on charcoal are added to a solution of 70 mg 2-(3-Methoxy-6-pyridin-4-yl-pyridazin-4-yl)-3-vinyl-1H-indole methanol, and the reaction mixture is stirred under an hydrogen atmosphere for 4 hours. The catalyst is removed by filtration and the solvent by evaporation yielding the product which was used... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Secondary amine.Vinyl | null | c1ccc2c(c1)CCN2 | c1ccc2[nH]ccc2c1 | c1ccnnc1.c1ccncc1.c1ccc2[nH]ccc2c1 | HO- | [Pd] | null | 4 | C=CC1c2ccccc2NC1(CO)c1cc(-c2ccncc2)nnc1OC>[Pd]>CCc1c(-c2cc(-c3ccncc3)nnc2OC)[nH]c2ccccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-abda347c2ef249bc8915db008f19ce56 | CCc1c(-c2cc(-c3ccncc3)nnc2OC)[nH]c2ccccc12>>CCc1c(-c2cc(-c3ccncc3)n[nH]c2=O)[nH]c2ccccc12 | C(C)C1=C(NC2=CC=CC=C12)C1=C(N=NC(=C1)C1=CC=NC=C1)OC.C(C)#N.O.C(=O)O>>C(C)C1=C(NC2=CC=CC=C12)C=1C(NN=C(C1)C1=CC=NC=C1)=O | C[O:17][c:16]1[c:5](-[c:4]2[c:3]([CH2:2][CH3:1])[c:24]3[c:19]([nH:18]2)[cH:20][cH:21][cH:22][cH:23]3)[cH:6][c:7](-[c:8]2[cH:9][cH:10][n:11][cH:12][cH:13]2)[n:14][n:15]1>>[CH3:1][CH2:2][c:3]1[c:4](-[c:5]2[cH:6][c:7](-[c:8]3[cH:9][cH:10][n:11][cH:12][cH:13]3)[n:14][nH:15][c:16]2=[O:17])[nH:18][c:19]2[cH:20][cH:21][cH:22]... | CCc1c(-c2cc(-c3ccncc3)nnc2OC)[nH]c2ccccc12 | CCc1c(-c2cc(-c3ccncc3)n[nH]c2=O)[nH]c2ccccc12 | null | null | [OH-].[Na+].C(C)O | Miscellaneous | OtherReaction | 3a907fa62544f46964e2b473ab8a45caedf80503ce5e705ae3da44b55acc0eb2 | 291cad8b6dfbbd2c823b5c9d45efc37a166dc3454a9f151ac48cb357f4bc155f | O=c1[nH]nc(-c2ccncc2)cc1-c1cc2ccccc2[nH]1 | C-[O;H0;D2;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[#7;a:4]:[c:5]:[c:6]:[c:7]:1-[c:8]:[#7;a:9]>>[#7;a:9]:[c:8]-[c:7]1:[c:6]:[c:5]:[#7;a:4]:[nH;D2;+0:3]:[c;H0;D3;+0:2]:1=[O;H0;D1;+0:1] | null | [] | 150 | CELSIUS | null | null | 60 mg 3-Ethyl-2-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-1H-indole is dissolved in 0.5 ml ethanol and 0.5 ml 1N aqueous NaOH solution. The reaction mixture is stirred at 150° C. in microwave apparatus (200 W). The reaction mixture is directly applied to HPLC chromatography to isolate the product (RP18 column, acetonit... | 10.6084/m9.figshare.5104873.v1 | null | Ether | null | c1ccnnc1 | c1cnncc1 | c1cnncc1.c1ccncc1.c1ccc2[nH]ccc2c1 | Other | [OH-].[Na+].C(C)O | 150 | null | CCc1c(-c2cc(-c3ccncc3)nnc2OC)[nH]c2ccccc12>[OH-].[Na+].C(C)O>CCc1c(-c2cc(-c3ccncc3)n[nH]c2=O)[nH]c2ccccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-259b42023b664515a996f4294d8c1ae5 | C1COCCN1.C=O.O=c1[nH]nc(-c2ccncc2)cc1-c1cc2ccccc2[nH]1>>O=c1[nH]nc(-c2ccncc2)cc1-c1[nH]c2ccccc2c1CN1CCOCC1 | [OH-].[Na+].C=O.N1CCOCC1.N1C(=CC2=CC=CC=C12)C=1C(NN=C(C1)C1=CC=NC=C1)=O>>N1(CCOCC1)CC1=C(NC2=CC=CC=C12)C=1C(NN=C(C1)C1=CC=NC=C1)=O | [NH:24]1[CH2:25][CH2:26][O:27][CH2:28][CH2:29]1.O=[CH2:23].[O:1]=[c:2]1[nH:3][n:4][c:5](-[c:6]2[cH:7][cH:8][n:9][cH:10][cH:11]2)[cH:12][c:13]1-[c:14]1[nH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[cH:22]1>>[O:1]=[c:2]1[nH:3][n:4][c:5](-[c:6]2[cH:7][cH:8][n:9][cH:10][cH:11]2)[cH:12][c:13]1-[c:14]1[nH:15][c:16]2[cH:17... | C1COCCN1.C=O.O=c1[nH]nc(-c2ccncc2)cc1-c1cc2ccccc2[nH]1 | O=c1[nH]nc(-c2ccncc2)cc1-c1[nH]c2ccccc2c1CN1CCOCC1 | null | null | O1CCOCC1.C(C)(=O)O | Heteroatom Alkylation and Arylation | OtherReaction | 8fe770f617c873b341268f271197203396fa684d2848d3c06932569abea4d8be | e1fdef8fde1c506d7c9deb8fd5e6f322eceea2abce3167abcf412a1fa4fd5443 | O=c1[nH]nc(-c2ccncc2)cc1-c1[nH]c2ccccc2c1CN1CCOCC1 | O=[CH2;D1;+0:1].[#7;a:2]:[c:3]:[c:4]-[c:5]1:[#7;a:6]:[c:7](:[c:8]):[c:9](:[c:10]):[cH;D2;+0:11]:1.[#8:12]1-[C:13]-[C:14]-[NH;D2;+0:15]-[C:16]-[C:17]-1>>[#7;a:2]:[c:3]:[c:4]-[c:5]1:[#7;a:6]:[c:7](:[c:8]):[c:9](:[c:10]):[c;H0;D3;+0:11]:1-[CH2;D2;+0:1]-[N;H0;D3;+0:15]1-[C:14]-[C:13]-[#8:12]-[C:17]-[C:16]-1 | null | [] | null | null | 3 | HOUR | A solution of 14 ul formaldehyde (37% solution in water) and 17 ul morpholine in 0.5 ml glacial acetic acid is added dropwise at 0° C. to 50 mg 4-(1H-Indol-2-yl)-6-pyridin-4-yl-2H-pyridazin-3-one suspended in 2.24 ml glacial acetic acid and 2.6 ml 1,4-Dioxan. The resulting mixture is stirred for 3 h at room temperature... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine | Tertiary amine | C1COCCN1.c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.C1COCC[NH]1 | c1cnncc1.c1ccncc1.c1ccc2[nH]ccc2c1.C1COCC[NH]1 | HO- | O1CCOCC1.C(C)(=O)O | null | 3 | C1COCCN1.C=O.O=c1[nH]nc(-c2ccncc2)cc1-c1cc2ccccc2[nH]1>O1CCOCC1.C(C)(=O)O>O=c1[nH]nc(-c2ccncc2)cc1-c1[nH]c2ccccc2c1CN1CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2d7ada8edbb44b57bbc24d685b7e8e78 | O=C1CCC(=O)N1Br.O=c1[nH]nc(-c2ccncc2)cc1-c1cc2ccccc2[nH]1>>O=c1[nH]nc(-c2ccncc2)cc1-c1[nH]c2ccccc2c1Br | N1C(=CC2=CC=CC=C12)C=1C(NN=C(C1)C1=CC=NC=C1)=O.BrN1C(CCC1=O)=O>>BrC1=C(NC2=CC=CC=C12)C=1C(NN=C(C1)C1=CC=NC=C1)=O | O=C1CCC(=O)N1[Br:23].[O:1]=[c:2]1[nH:3][n:4][c:5](-[c:6]2[cH:7][cH:8][n:9][cH:10][cH:11]2)[cH:12][c:13]1-[c:14]1[nH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[cH:22]1>>[O:1]=[c:2]1[nH:3][n:4][c:5](-[c:6]2[cH:7][cH:8][n:9][cH:10][cH:11]2)[cH:12][c:13]1-[c:14]1[nH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[c:22]1[B... | O=C1CCC(=O)N1Br.O=c1[nH]nc(-c2ccncc2)cc1-c1cc2ccccc2[nH]1 | O=c1[nH]nc(-c2ccncc2)cc1-c1[nH]c2ccccc2c1Br | null | null | CC(=O)C | Functional Group Interconversion | Bromination | 0754ae2664ff7ba9610e6f272707033ed8b7278ddd1c23d9264359692cf74d77 | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=c1[nH]nc(-c2ccncc2)cc1-c1cc2ccccc2[nH]1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#7;a:2]:[c:3]:[c:4]-[c:5]1:[#7;a:6]:[c:7](:[c:8]):[c:9](:[c:10]):[cH;D2;+0:11]:1>>[#7;a:2]:[c:3]:[c:4]-[c:5]1:[#7;a:6]:[c:7](:[c:8]):[c:9](:[c:10]):[c;H0;D3;+0:11]:1-[Br;H0;D1;+0:1] | null | [] | null | null | 3 | HOUR | 22 mg 4-(1H-Indol-2-yl)-6-pyridin-4-yl-2H-pyridazin-3-one is suspended in 30 mL acetone and 2 mg N-bromosuccinimide is added. The reaction mixture is stirred for 3 hours at room temperature, the precipitated product isolated by filtration and washed with acetone. The product is purified by preparative RP-HPLC eluting w... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | C1CCNC1.c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1cnncc1.c1ccncc1.c1ccc2[nH]ccc2c1 | HO- | CC(=O)C | null | 3 | O=C1CCC(=O)N1Br.O=c1[nH]nc(-c2ccncc2)cc1-c1cc2ccccc2[nH]1>CC(=O)C>O=c1[nH]nc(-c2ccncc2)cc1-c1[nH]c2ccccc2c1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ef0d5160087c40a19b5856f0bc9e8161 | CC=O.COc1ccc(-c2ccncc2)nn1>>COc1nnc(-c2ccncc2)cc1C(C)O | C(C)=O.COC=1N=NC(=CC1)C1=CC=NC=C1.CC1(NC(CCC1)(C)C)C.C(CCC)[Li]>>COC=1N=NC(=CC1C(C)O)C1=CC=NC=C1 | [CH:15]([CH3:16])=[O:17].[CH3:1][O:2][c:3]1[n:4][n:5][c:6](-[c:7]2[cH:8][cH:9][n:10][cH:11][cH:12]2)[cH:13][cH:14]1>>[CH3:1][O:2][c:3]1[n:4][n:5][c:6](-[c:7]2[cH:8][cH:9][n:10][cH:11][cH:12]2)[cH:13][c:14]1[CH:15]([CH3:16])[OH:17] | CC=O.COc1ccc(-c2ccncc2)nn1 | COc1nnc(-c2ccncc2)cc1C(C)O | null | null | C1CCOC1 | C-C Coupling | OtherReaction | a27fffed4aaf6d2a30bf6b0df69ab017955ce9c7a44f21694f8a14adcbb193f6 | a7cae52d902b2812376f5459a7a8b7ead54e8ef31fd78982d2e99bec532613ba | c1cnnc(-c2ccncc2)c1 | [#8:1]-[c:2]1:[#7;a:3]:[#7;a:4]:[c:5](-[c:6]):[c:7]:[cH;D2;+0:8]:1.[C;D1;H3:9]-[CH;D2;+0:10]=[O;H0;D1;+0:11]>>[#8:1]-[c:2]1:[#7;a:3]:[#7;a:4]:[c:5](-[c:6]):[c:7]:[c;H0;D3;+0:8]:1-[CH;D3;+0:10](-[C;D1;H3:9])-[OH;D1;+0:11] | 66 | [{"value": 66.0, "product": "COC=1N=NC(=CC1C(C)O)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.8, "product": "COC=1N=NC(=CC1C(C)O)C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | To a solution of 0.93 g 2,2,6,6-tetramethylpiperidine in 30 ml THF is added 4.13 ml (15% solution in toluene) n-butyllithium at −30° C. After being stirred at 0° C. for 30 min, the reaction mixture is cooled to −78° C. and a solution of 1.12 g 3-methoxy-6-pyridin-4-yl-pyridazine in 30 ml THF is added and stirred at −78... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Secondary alcohol | c1ccnnc1 | c1ccnnc1 | c1ccnnc1.c1ccncc1 | null | C1CCOC1 | 0 | 0.5 | CC=O.COc1ccc(-c2ccncc2)nn1>C1CCOC1>COc1nnc(-c2ccncc2)cc1C(C)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fda2ba8339ae49b3950cb537d1f4f04f | COc1nnc(-c2ccncc2)cc1C(C)O>>COc1nnc(-c2ccncc2)cc1C(C)=O | COC=1N=NC(=CC1C(C)O)C1=CC=NC=C1.CC(=O)OI1(C2=CC=CC=C2C(=O)O1)(OC(=O)C)OC(=O)C>>COC=1N=NC(=CC1C(C)=O)C1=CC=NC=C1 | [CH3:1][O:2][c:3]1[n:4][n:5][c:6](-[c:7]2[cH:8][cH:9][n:10][cH:11][cH:12]2)[cH:13][c:14]1[CH:15]([CH3:16])[OH:17]>>[CH3:1][O:2][c:3]1[n:4][n:5][c:6](-[c:7]2[cH:8][cH:9][n:10][cH:11][cH:12]2)[cH:13][c:14]1[C:15]([CH3:16])=[O:17] | COc1nnc(-c2ccncc2)cc1C(C)O | COc1nnc(-c2ccncc2)cc1C(C)=O | null | null | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | c1cnnc(-c2ccncc2)c1 | [#8:1]-[c:2]1:[#7;a:3]:[#7;a:4]:[c:5]:[c:6]:[c:7]:1-[CH;D3;+0:8](-[C;D1;H3:9])-[OH;D1;+0:10]>>[#8:1]-[c:2]1:[#7;a:3]:[#7;a:4]:[c:5]:[c:6]:[c:7]:1-[C;H0;D3;+0:8](-[C;D1;H3:9])=[O;H0;D1;+0:10] | 92 | [{"value": 92.0, "product": "COC=1N=NC(=CC1C(C)=O)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.0, "product": "COC=1N=NC(=CC1C(C)=O)C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of 0.91 g 1-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-ethanol in 10 ml CH2Cl2 is added a suspension of 1.70 g Dess-Martin Periodane in 10 ml CH2Cl2 at room temperature. After being stirred for 3 h, the suspension is extracted with 5% aq. Na2S2O3 solution. The organic layer is washed with water, dried over... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | c1ccnnc1.c1ccncc1 | null | C(Cl)Cl | null | 3 | COc1nnc(-c2ccncc2)cc1C(C)O>C(Cl)Cl>COc1nnc(-c2ccncc2)cc1C(C)=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-30d999d6d5da476a805d170eef6c17db | COc1nnc(-c2ccncc2)cc1-c1cc2cc(C(C)C)ccc2[nH]1>>CC(C)c1ccc2[nH]c(-c3cc(-c4ccncc4)n[nH]c3=O)cc2c1 | C(C)(C)C=1C=C2C=C(NC2=CC1)C1=C(N=NC(=C1)C1=CC=NC=C1)OC.[OH-].[Na+]>>C(C)(C)C=1C=C2C=C(NC2=CC1)C=1C(NN=C(C1)C1=CC=NC=C1)=O | C[O:22][c:21]1[c:10](-[c:9]2[nH:8][c:7]3[cH:6][cH:5][c:4]([CH:2]([CH3:1])[CH3:3])[cH:25][c:24]3[cH:23]2)[cH:11][c:12](-[c:13]2[cH:14][cH:15][n:16][cH:17][cH:18]2)[n:19][n:20]1>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]2[nH:8][c:9](-[c:10]3[cH:11][c:12](-[c:13]4[cH:14][cH:15][n:16][cH:17][cH:18]4)[n:19][nH:20][c:21]... | COc1nnc(-c2ccncc2)cc1-c1cc2cc(C(C)C)ccc2[nH]1 | CC(C)c1ccc2[nH]c(-c3cc(-c4ccncc4)n[nH]c3=O)cc2c1 | null | null | CCO | Miscellaneous | OtherReaction | 3a907fa62544f46964e2b473ab8a45caedf80503ce5e705ae3da44b55acc0eb2 | 291cad8b6dfbbd2c823b5c9d45efc37a166dc3454a9f151ac48cb357f4bc155f | O=c1[nH]nc(-c2ccncc2)cc1-c1cc2ccccc2[nH]1 | C-[O;H0;D2;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[#7;a:4]:[c:5]:[c:6]:[c:7]:1-[c:8]:[#7;a:9]>>[#7;a:9]:[c:8]-[c:7]1:[c:6]:[c:5]:[#7;a:4]:[nH;D2;+0:3]:[c;H0;D3;+0:2]:1=[O;H0;D1;+0:1] | 11 | [{"value": 11.0, "product": "C(C)(C)C=1C=C2C=C(NC2=CC1)C=1C(NN=C(C1)C1=CC=NC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 10.5, "product": "C(C)(C)C=1C=C2C=C(NC2=CC1)C=1C(NN=C(C1)C1=CC=NC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | null | null | To a solution of 139 mg (crude material) 5-isopropyl-2-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-1H-indole in 2.5 ml EtOH is added 2.5 ml aq. NaOH (1 M). The mixture is heated for 10 min at 150° C. using microwave. After cooling to room temperature the mixture is filtered and purified by HPLC to give 14 mg (11%) of the... | 10.6084/m9.figshare.5104873.v1 | null | Ether | null | c1ccnnc1 | c1cnncc1 | c1ccc2[nH]ccc2c1.c1cnncc1.c1ccncc1 | Other | CCO | 150 | null | COc1nnc(-c2ccncc2)cc1-c1cc2cc(C(C)C)ccc2[nH]1>CCO>CC(C)c1ccc2[nH]c(-c3cc(-c4ccncc4)n[nH]c3=O)cc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-24a8127de3a04e3592f183c34bbe44e8 | CC(=O)Cl.COc1nnc(-c2ccncc2)cc1-c1cc2ccccc2[nH]1>>CC(=O)c1c(-c2cc(-c3ccncc3)n[nH]c2=O)[nH]c2ccccc12 | C(C)(=O)Cl.ClCCCl.[Cl-].[Al+3].[Cl-].[Cl-].FC(C(=O)O)(F)F.COC=1N=NC(=CC1C=1NC2=CC=CC=C2C1)C1=CC=NC=C1>>C(C)(=O)C1=C(NC2=CC=CC=C12)C=1C(NN=C(C1)C1=CC=NC=C1)=O | Cl[C:2]([CH3:1])=[O:3].C[O:18][c:17]1[c:6](-[c:5]2[cH:4][c:25]3[c:20]([nH:19]2)[cH:21][cH:22][cH:23][cH:24]3)[cH:7][c:8](-[c:9]2[cH:10][cH:11][n:12][cH:13][cH:14]2)[n:15][n:16]1>>[CH3:1][C:2](=[O:3])[c:4]1[c:5](-[c:6]2[cH:7][c:8](-[c:9]3[cH:10][cH:11][n:12][cH:13][cH:14]3)[n:15][nH:16][c:17]2=[O:18])[nH:19][c:20]2[cH:2... | CC(=O)Cl.COc1nnc(-c2ccncc2)cc1-c1cc2ccccc2[nH]1 | CC(=O)c1c(-c2cc(-c3ccncc3)n[nH]c2=O)[nH]c2ccccc12 | null | null | null | Acylation | OtherReaction | 20b7fe8fa1eec589fd08a2a4fea071d764dc4c09cfad5a5fb1f99f7540bb4b04 | 404ac493a92648b12d897060b845969d840d30aa4e379815a25f94ff447379d8 | O=c1[nH]nc(-c2ccncc2)cc1-c1cc2ccccc2[nH]1 | C-[O;H0;D2;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[#7;a:4]:[c:5]:[c:6]:[c:7]:1-[c:8]1:[#7;a:9]:[c:10](:[c:11]):[c:12](:[c:13]):[cH;D2;+0:14]:1.Cl-[C;H0;D3;+0:15](-[C;D1;H3:16])=[O;D1;H0:17]>>[C;D1;H3:16]-[C;H0;D3;+0:15](=[O;D1;H0:17])-[c;H0;D3;+0:14]1:[c:12](:[c:13]):[c:10](:[c:11]):[#7;a:9]:[c:8]:1-[c:7]1:[c:6]:[c:5]:[#... | 48.1 | [{"value": 48.1, "product": "C(C)(=O)C1=C(NC2=CC=CC=C12)C=1C(NN=C(C1)C1=CC=NC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4 mg acetyl chloride are added at 0° C. to a suspension of 80 mg aluminum chloride 1,2-Dichloroethane, followed by 208 mg 2-(3-Methoxy-6-pyridin-4-yl-pyridazin-4-yl)-1H-indole Trifluoroacetate. The reaction mixture is stirred for 4 h at room temperature and for 3h at 50° C. It is worked up pouring into an ice/water mix... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether | Ketone | c1ccnnc1.c1ccc2[nH]ccc2c1 | c1cnncc1.c1ccc2[nH]ccc2c1 | c1cnncc1.c1ccncc1.c1ccc2[nH]ccc2c1 | HCl | null | null | null | CC(=O)Cl.COc1nnc(-c2ccncc2)cc1-c1cc2ccccc2[nH]1>>CC(=O)c1c(-c2cc(-c3ccncc3)n[nH]c2=O)[nH]c2ccccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9e5fc3ac1d3a4b60b4e53322e78f8a86 | CC(C)(C)[Si](C)(C)Cl.Oc1ccc2cc[nH]c2c1>>CC(C)(C)[Si](C)(C)Oc1ccc2cc[nH]c2c1 | OC1=CC=C2C=CNC2=C1.[Si](C)(C)(C(C)(C)C)Cl.N1C=NC=C1.CN(C=O)C>>O([Si](C)(C)C(C)(C)C)C1=CC=C2C=CNC2=C1 | Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][c:9]1[cH:10][cH:11][c:12]2[cH:13][cH:14][nH:15][c:16]2[cH:17]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][c:9]1[cH:10][cH:11][c:12]2[cH:13][cH:14][nH:15][c:16]2[cH:17]1 | CC(C)(C)[Si](C)(C)Cl.Oc1ccc2cc[nH]c2c1 | CC(C)(C)[Si](C)(C)Oc1ccc2cc[nH]c2c1 | null | null | C(C)(=O)OCC | Protection | Alcohol protection with silyl ethers | 91043baed1393f1ecd2302d7d0b31c01cf171d3977dd7c70afa1da52fa298c73 | 4a917c959d011f885a1269fa3c1f022ee5e09144996246d24e42e65634a451ac | c1ccc2[nH]ccc2c1 | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[#7;a:8]:[c:9]:[c:10]:[c:11](-[OH;D1;+0:12]):[c:13]>>[#7;a:8]:[c:9]:[c:10]:[c:11](-[O;H0;D2;+0:12]-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7]):[c:13] | 88.6 | [{"value": 88.0, "product": "O([Si](C)(C)C(C)(C)C)C1=CC=C2C=CNC2=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.6, "product": "O([Si](C)(C)C(C)(C)C)C1=CC=C2C=CNC2=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | A mixture of 5.5 g 6-hydroxyindole, 7.47 g tert-butyldimethylsilyl chloride, 7.03 g imidazole, and 25 mL dimethylformamide is stirred at ambient temperature for 20 h. The reaction is diluted with ethyl acetate, washed with water (2×), dried (MgSO4), and the solvent removed under reduced pressure to provide an oil. The ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Silyl protective group | TMS ether protective group | null | null | c1ccc2[nH]ccc2c1 | HCl | C(C)(=O)OCC | null | 20 | CC(C)(C)[Si](C)(C)Cl.Oc1ccc2cc[nH]c2c1>C(C)(=O)OCC>CC(C)(C)[Si](C)(C)Oc1ccc2cc[nH]c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bcaa333902f44bb3aba5645c7b8da4fa | CC(C)(C)OC(=O)n1ccc2ccc(O[Si](C)(C)C(C)(C)C)cc21>>CC(C)(C)OC(=O)n1c(B(O)O)cc2ccc(O[Si](C)(C)C(C)(C)C)cc21 | [Cl-].[NH4+].COB(OC)OC.C(C)(C)(C)OC(=O)N1C=CC2=CC=C(C=C12)O[Si](C)(C)C(C)(C)C.C(C)(C)(C)[Li].OS(=O)(=O)[O-].[K+].OS(=O)(=O)O>>C(C)(C)(C)OC(=O)N1C(=CC2=CC=C(C=C12)O[Si](C)(C)C(C)(C)C)B(O)O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[n:8]1[cH:9][cH:13][c:14]2[cH:15][cH:16][c:17]([O:18][Si:19]([CH3:20])([CH3:21])[C:22]([CH3:23])([CH3:24])[CH3:25])[cH:26][c:27]12>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[n:8]1[c:9]([B:10]([OH:11])[OH:12])[cH:13][c:14]2[cH:15][cH:16][c:17]([O:18][Si:19]([CH3:20]... | CC(C)(C)OC(=O)n1ccc2ccc(O[Si](C)(C)C(C)(C)C)cc21 | CC(C)(C)OC(=O)n1c(B(O)O)cc2ccc(O[Si](C)(C)C(C)(C)C)cc21 | null | null | O1CCCC1.CCOCC.CCCCC | Functional Group Interconversion | OtherReaction | 4b0e6aa4d1fd1c5214dd3931ca16cd67f94912c719f614bc8380822d6ecd3d94 | d6d312d46f766d2774f96de1fd96fd8f98a20e51a20ef3280f850cd6a3c77869 | c1ccc2[nH]ccc2c1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](=[O;D1;H0:7])-[#7;a:8]1:[c:9]:[c:10]:[c:11]:[cH;D2;+0:12]:1>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](=[O;D1;H0:7])-[#7;a:8]1:[c:9]:[c:10]:[c:11]:[c;H0;D3;+0:12]:1-[#5:13](-[O;D1;H1:14])-[O;D1;H1:15] | 56 | [{"value": 56.0, "product": "C(C)(C)(C)OC(=O)N1C(=CC2=CC=C(C=C12)O[Si](C)(C)C(C)(C)C)B(O)O", "details": "PERCENTYIELD", "is_desired": false}] | 78 | CELSIUS | 32 | MINUTE | To a solution of 1 g 1-(tert-butoxycarbonyl)-6-(tert-butyldimethylsiloxy)indole in 15 mL anhydrous tetrahydrofuran at −78° C. under nitrogen is added tert-butyllithium (2.30 mL of a 1.5 M solution in pentane) over 3 min, and the reaction is stirred at ˜78° C. After 32 min, 0.66 mL trimethylborate are added in one porti... | 10.6084/m9.figshare.5104873.v1 | null | null | Boronic acid | c1ccc2cc[nH]c2c1 | c1ccc2cc[nH]c2c1 | c1ccc2cc[nH]c2c1 | null | O1CCCC1.CCOCC.CCCCC | 78 | 0.533333 | CC(C)(C)OC(=O)n1ccc2ccc(O[Si](C)(C)C(C)(C)C)cc21>O1CCCC1.CCOCC.CCCCC>CC(C)(C)OC(=O)n1c(B(O)O)cc2ccc(O[Si](C)(C)C(C)(C)C)cc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5b2c326aaee243048156ce6181409011 | CN(C)CCO.COc1nnc(-c2ccncc2)cc1-c1cc2ccc(O)cc2n1C(=O)OC(C)(C)C>>COc1nnc(-c2ccncc2)cc1-c1cc2ccc(OCCN(C)C)cc2n1C(=O)OC(C)(C)C | C(C)(C)(C)OC(=O)N1C(=CC2=CC=C(C=C12)O)C1=C(N=NC(=C1)C1=CC=NC=C1)OC.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.CN(CCO)C.N(=NC(=O)OCC)C(=O)OCC>>C(C)(C)(C)OC(=O)N1C(=CC2=CC=C(C=C12)OCCN(C)C)C1=C(N=NC(=C1)C1=CC=NC=C1)OC | O[CH2:22][CH2:23][N:24]([CH3:25])[CH3:26].[CH3:1][O:2][c:3]1[n:4][n:5][c:6](-[c:7]2[cH:8][cH:9][n:10][cH:11][cH:12]2)[cH:13][c:14]1-[c:15]1[cH:16][c:17]2[cH:18][cH:19][c:20]([OH:21])[cH:27][c:28]2[n:29]1[C:30](=[O:31])[O:32][C:33]([CH3:34])([CH3:35])[CH3:36]>>[CH3:1][O:2][c:3]1[n:4][n:5][c:6](-[c:7]2[cH:8][cH:9][n:10][... | CN(C)CCO.COc1nnc(-c2ccncc2)cc1-c1cc2ccc(O)cc2n1C(=O)OC(C)(C)C | COc1nnc(-c2ccncc2)cc1-c1cc2ccc(OCCN(C)C)cc2n1C(=O)OC(C)(C)C | null | null | C1(=CC=CC=C1)C.C1CCOC1 | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccc2[nH]c(-c3cnnc(-c4ccncc4)c3)cc2c1 | O-[CH2;D2;+0:1]-[C:2]-[#7:3].[#7;a:4]:[c:5]:[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:8]-[c:7](:[c:9]):[c:6]:[c:5]:[#7;a:4] | 43 | [{"value": 43.0, "product": "C(C)(C)(C)OC(=O)N1C(=CC2=CC=C(C=C12)OCCN(C)C)C1=C(N=NC(=C1)C1=CC=NC=C1)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | 100 mg 6-hydroxy-2-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-indole-1-carboxylic acid tert-butyl ester and 175 mg triphenylphosphine are dissolved in 7 mL toluene and 2 mL THF. After dropwise addition of 84 μL 2-dimethylaminoethanol and 123 μL diethyl azodicarboxylate, the reaction mixture is stirred at room temperatur... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccnnc1.c1ccncc1.c1ccc2cc[nH]c2c1 | HO- | C1(=CC=CC=C1)C.C1CCOC1 | null | 5 | CN(C)CCO.COc1nnc(-c2ccncc2)cc1-c1cc2ccc(O)cc2n1C(=O)OC(C)(C)C>C1(=CC=CC=C1)C.C1CCOC1>COc1nnc(-c2ccncc2)cc1-c1cc2ccc(OCCN(C)C)cc2n1C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eb075f340d53495fa1b59f44d7390793 | CCC=O.COc1ccc(Cl)nn1>>CCC(O)c1cc(Cl)nnc1OC | Cl.C(CC)=O.C(CCC)[Li].ClC=1N=NC(=CC1)OC.C([O-])(O)=O.[Na+].CC1(NC(CCC1)(C)C)C>>ClC1=CC(=C(N=N1)OC)C(CC)O | [CH3:1][CH2:2][CH:3]=[O:4].[cH:5]1[cH:6][c:7]([Cl:8])[n:9][n:10][c:11]1[O:12][CH3:13]>>[CH3:1][CH2:2][CH:3]([OH:4])[c:5]1[cH:6][c:7]([Cl:8])[n:9][n:10][c:11]1[O:12][CH3:13] | CCC=O.COc1ccc(Cl)nn1 | CCC(O)c1cc(Cl)nnc1OC | null | null | O1CCCC1.CCCCCC.C(C)O | C-C Coupling | OtherReaction | a27fffed4aaf6d2a30bf6b0df69ab017955ce9c7a44f21694f8a14adcbb193f6 | a7cae52d902b2812376f5459a7a8b7ead54e8ef31fd78982d2e99bec532613ba | c1ccnnc1 | [#8:1]-[c:2]1:[#7;a:3]:[#7;a:4]:[c:5](-[Cl;D1;H0:6]):[c:7]:[cH;D2;+0:8]:1.[C;D1;H3:9]-[C:10]-[CH;D2;+0:11]=[O;H0;D1;+0:12]>>[#8:1]-[c:2]1:[#7;a:3]:[#7;a:4]:[c:5](-[Cl;D1;H0:6]):[c:7]:[c;H0;D3;+0:8]:1-[CH;D3;+0:11](-[OH;D1;+0:12])-[C:10]-[C;D1;H3:9] | null | [] | 0 | CELSIUS | 30 | MINUTE | 104.6 ml of a 1.6M solution of n-Butyl lithium in hexane is added dropwise at −75° C. to 200 ml tetrahydrofuran followed by 28.3 ml 2,2,6,6-tetramethylpiperidine and the resulting solution is allowed to warm to 0° C. and stirred for 30 min. The solution is cooled to −75° C. and a solution of 11 g 3-chloro-6-methoxypyri... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Secondary alcohol | c1ccnnc1 | c1ccnnc1 | c1ccnnc1 | null | O1CCCC1.CCCCCC.C(C)O | 0 | 0.5 | CCC=O.COc1ccc(Cl)nn1>O1CCCC1.CCCCCC.C(C)O>CCC(O)c1cc(Cl)nnc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-695cb214ce6b4accb0e739d2448d5410 | CCC(O)c1cc(Cl)nnc1OC>>CCC(=O)c1cc(Cl)nnc1OC | ClC1=CC(=C(N=N1)OC)C(CC)O>>ClC1=CC(=C(N=N1)OC)C(CC)=O | [CH3:1][CH2:2][CH:3]([OH:4])[c:5]1[cH:6][c:7]([Cl:8])[n:9][n:10][c:11]1[O:12][CH3:13]>>[CH3:1][CH2:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([Cl:8])[n:9][n:10][c:11]1[O:12][CH3:13] | CCC(O)c1cc(Cl)nnc1OC | CCC(=O)c1cc(Cl)nnc1OC | null | [O-2].[O-2].[Mn+4] | O1CCCC1 | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | c1ccnnc1 | [#8:1]-[c:2]1:[#7;a:3]:[#7;a:4]:[c:5]:[c:6]:[c:7]:1-[CH;D3;+0:8](-[OH;D1;+0:9])-[C:10]-[C;D1;H3:11]>>[#8:1]-[c:2]1:[#7;a:3]:[#7;a:4]:[c:5]:[c:6]:[c:7]:1-[C;H0;D3;+0:8](=[O;H0;D1;+0:9])-[C:10]-[C;D1;H3:11] | null | [] | null | null | 24 | HOUR | 12.25 g 1-(6-Chloro-3-methoxy-pyridazin-4-yl)-propan-1-ol is dissolved in 410 ml tetrahydrofuran and 105 g of manganese dioxide is added. The reaction is stirred for 24 h at RT. Solids are removed by filtration, and the solution is treated with a further 105 g of manganese dioxide for 16 h at RT. Solids are removed by ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | c1ccnnc1 | null | [O-2].[O-2].[Mn+4].O1CCCC1 | null | 24 | CCC(O)c1cc(Cl)nnc1OC>[O-2].[O-2].[Mn+4].O1CCCC1>CCC(=O)c1cc(Cl)nnc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-43eba2caeef14a1ea548eb0145350cad | CCC(=O)c1cc(Cl)nnc1OC.Cc1cc(B2OC(C)(C)C(C)(C)O2)cc(C)c1O>>CCC(=O)c1cc(-c2cc(C)c(O)c(C)c2)nnc1OC | CC1=C(C(=CC(=C1)B1OC(C(O1)(C)C)(C)C)C)O.C([O-])([O-])=O.[Na+].[Na+].C(C)(=O)OCC.ClC1=CC(=C(N=N1)OC)C(CC)=O>>OC1=C(C=C(C=C1C)C1=CC(=C(N=N1)OC)C(CC)=O)C | Cl[c:7]1[cH:6][c:5]([C:3]([CH2:2][CH3:1])=[O:4])[c:19]([O:20][CH3:21])[n:18][n:17]1.CC1(C)OB([c:8]2[cH:9][c:10]([CH3:11])[c:12]([OH:13])[c:14]([CH3:15])[cH:16]2)OC1(C)C>>[CH3:1][CH2:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][c:10]([CH3:11])[c:12]([OH:13])[c:14]([CH3:15])[cH:16]2)[n:17][n:18][c:19]1[O:20][CH3:21] | CCC(=O)c1cc(Cl)nnc1OC.Cc1cc(B2OC(C)(C)C(C)(C)O2)cc(C)c1O | CCC(=O)c1cc(-c2cc(C)c(O)c(C)c2)nnc1OC | null | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | COCCOC | C-C Coupling | Suzuki coupling with boronic esters | 7d3abbda54e933df9ff9dc39c70f4c4ada1c268870f29590395c2cc6bed1dda1 | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | c1ccc(-c2cccnn2)cc1 | C-C1(-C)-O-B(-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-O-C-1(-C)-C.Cl-[c;H0;D3;+0:6]1:[#7;a:7]:[#7;a:8]:[c:9]:[c:10](-[C:11]=[O;D1;H0:12]):[c:13]:1>>[O;D1;H0:12]=[C:11]-[c:10]1:[c:9]:[#7;a:8]:[#7;a:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:13]:1 | null | [] | null | null | 5 | MINUTE | 2 g of 1-(6-Chloro-3-methoxy-pyridazin-4-yl)-propan-1-one and 1.73 g of tetrakis(triphenylphosphine) palladium (0) are dissolved in 10 ml DME and the solution is stirred for 5 min at RT under argon. 3 g of 2,6-Dimethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol and 10 ml of a 2M aqueous solution of sodium ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | c1ccnnc1.B1OCCO1.c1ccccc1 | c1ccnnc1.c1ccccc1 | c1ccnnc1.c1ccccc1 | HCl.B | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.COCCOC | null | 0.083333 | CCC(=O)c1cc(Cl)nnc1OC.Cc1cc(B2OC(C)(C)C(C)(C)O2)cc(C)c1O>[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.COCCOC>CCC(=O)c1cc(-c2cc(C)c(O)c(C)c2)nnc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dfbd9f5c18534ceebd8b86e1288c2370 | CCC(=O)c1cc(-c2cc(C)c(O)c(C)c2)nnc1OC.Nc1ccccc1Cl>>COc1nnc(-c2cc(C)c(O)c(C)c2)cc1-c1[nH]c2ccccc2c1C | ClC1=C(N)C=CC=C1.S(=O)(=O)([O-])[O-].[Mg+2].OC1=C(C=C(C=C1C)C1=CC(=C(N=N1)OC)C(CC)=O)C.C(C)(=O)O>>COC1=C(C=C(N=N1)C1=CC(=C(C(=C1)C)O)C)C=1NC2=CC=CC=C2C1C | O=[C:18]([c:17]1[c:3]([O:2][CH3:1])[n:4][n:5][c:6](-[c:7]2[cH:8][c:9]([CH3:10])[c:11]([OH:12])[c:13]([CH3:14])[cH:15]2)[cH:16]1)[CH2:26][CH3:27].Cl[c:25]1[c:20]([NH2:19])[cH:21][cH:22][cH:23][cH:24]1>>[CH3:1][O:2][c:3]1[n:4][n:5][c:6](-[c:7]2[cH:8][c:9]([CH3:10])[c:11]([OH:12])[c:13]([CH3:14])[cH:15]2)[cH:16][c:17]1-[c... | CCC(=O)c1cc(-c2cc(C)c(O)c(C)c2)nnc1OC.Nc1ccccc1Cl | COc1nnc(-c2cc(C)c(O)c(C)c2)cc1-c1[nH]c2ccccc2c1C | null | null | CC(=O)N(C)C | Aromatic Heterocycle Formation | OtherReaction | 2aeebda70d28950751bcff9d93d27d409a496c19f9c9b9893349a271b234d219 | 4e13c013c1ec63cb4e4f791be1390f390c40f8fc080e4593325e7876241ac282 | c1ccc(-c2cc(-c3cc4ccccc4[nH]3)cnn2)cc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[NH2;D1;+0:5]):[c:6].O=[C;H0;D3;+0:7](-[CH2;D2;+0:8]-[C;D1;H3:9])-[c;H0;D3;+0:10]1:[c:11]:[c:12](-[c:13]):[#7;a:14]:[#7;a:15]:[c:16]:1-[#8:17]>>[#8:17]-[c:16]1:[#7;a:15]:[#7;a:14]:[c:12](-[c:13]):[c:11]:[c;H0;D3;+0:10]:1-[c;H0;D3;+0:7]1:[nH;D2;+0:5]:[c:4](:[c:6]):[c;H0;D3;+0:1](:[... | null | [] | 140 | CELSIUS | null | null | 73.4 μl of 2-chloroaniline and 21 mg of anhydrous magnesium sulfate are suspended in 3 ml dimethylacetamide. 100 mg of 1-[6-(4-Hydroxy-3,5-dimethyl-phenyl)-3-methoxy-pyridazin-4-yl]-propan-1-one and 31.4 mg acetic acid are added and the reaction is degassed with argon. 96 mg of tripotassium phosphate and 35.7 mg of bis... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Primary amine | null | c1ccccc1 | c1ccc2[nH]ccc2c1 | c1ccnnc1.c1ccccc1.c1ccc2[nH]ccc2c1 | HCl | CC(=O)N(C)C | 140 | null | CCC(=O)c1cc(-c2cc(C)c(O)c(C)c2)nnc1OC.Nc1ccccc1Cl>CC(=O)N(C)C>COc1nnc(-c2cc(C)c(O)c(C)c2)cc1-c1[nH]c2ccccc2c1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0a7d41c35518413983d7f23b6fe8c52f | COc1nnc(-c2cc(C)c(O)c(C)c2)cc1-c1[nH]c2ccccc2c1C>>Cc1cc(-c2cc(-c3[nH]c4ccccc4c3C)c(=O)[nH]n2)cc(C)c1O | COC1=C(C=C(N=N1)C1=CC(=C(C(=C1)C)O)C)C=1NC2=CC=CC=C2C1C.C[Si](C)(C)Cl.[I-].[K+]>>OC1=C(C=C(C=C1C)C=1C=C(C(NN1)=O)C=1NC2=CC=CC=C2C1C)C | C[O:19][c:18]1[c:7](-[c:8]2[nH:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[c:16]2[CH3:17])[cH:6][c:5](-[c:4]2[cH:3][c:2]([CH3:1])[c:25]([OH:26])[c:23]([CH3:24])[cH:22]2)[n:21][n:20]1>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][c:7](-[c:8]3[nH:9][c:10]4[cH:11][cH:12][cH:13][cH:14][c:15]4[c:16]3[CH3:17])[c:18](=[O:19])[nH:2... | COc1nnc(-c2cc(C)c(O)c(C)c2)cc1-c1[nH]c2ccccc2c1C | Cc1cc(-c2cc(-c3[nH]c4ccccc4c3C)c(=O)[nH]n2)cc(C)c1O | null | null | C(C)#N.O | Miscellaneous | OtherReaction | 3a907fa62544f46964e2b473ab8a45caedf80503ce5e705ae3da44b55acc0eb2 | 291cad8b6dfbbd2c823b5c9d45efc37a166dc3454a9f151ac48cb357f4bc155f | O=c1[nH]nc(-c2ccccc2)cc1-c1cc2ccccc2[nH]1 | C-[O;H0;D2;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[#7;a:4]:[c:5]:[c:6]:[c:7]:1-[c:8]:[#7;a:9]>>[#7;a:9]:[c:8]-[c:7]1:[c:6]:[c:5]:[#7;a:4]:[nH;D2;+0:3]:[c;H0;D3;+0:2]:1=[O;H0;D1;+0:1] | null | [] | 80 | CELSIUS | null | null | 6 mg of 4-[6-Methoxy-5-(3-methyl-1H-indol-2-yl) -pyridazin-3-yl]-2,6-dimethyl-phenol is suspended in 2 ml acetonitrile and 6.5 mg of trimethylsilyl chloride and 9.96 mg of potassium iodide are added. The solution is heated to 80° C. for 3 h. The reaction solution is diluted with water and the product is purified by pre... | 10.6084/m9.figshare.5104873.v1 | null | Ether | null | c1ccnnc1 | c1cnncc1 | c1ccccc1.c1cnncc1.c1ccc2[nH]ccc2c1 | Other | C(C)#N.O | 80 | null | COc1nnc(-c2cc(C)c(O)c(C)c2)cc1-c1[nH]c2ccccc2c1C>C(C)#N.O>Cc1cc(-c2cc(-c3[nH]c4ccccc4c3C)c(=O)[nH]n2)cc(C)c1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f3bd3399003a4e82aa52d47a4c9b99e2 | O=C1CCC(=O)N1I.O=c1[nH]nc(-c2ccncc2)cc1-c1cc2ccccc2[nH]1>>O=c1[nH]nc(-c2ccncc2)cc1-c1[nH]c2ccccc2c1I | N1C(=CC2=CC=CC=C12)C=1C(NN=C(C1)C1=CC=NC=C1)=O.C1CC(=O)N(C1=O)I>>IC1=C(NC2=CC=CC=C12)C=1C(NN=C(C1)C1=CC=NC=C1)=O | O=C1CCC(=O)N1[I:23].[O:1]=[c:2]1[nH:3][n:4][c:5](-[c:6]2[cH:7][cH:8][n:9][cH:10][cH:11]2)[cH:12][c:13]1-[c:14]1[nH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[cH:22]1>>[O:1]=[c:2]1[nH:3][n:4][c:5](-[c:6]2[cH:7][cH:8][n:9][cH:10][cH:11]2)[cH:12][c:13]1-[c:14]1[nH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[c:22]1[I:... | O=C1CCC(=O)N1I.O=c1[nH]nc(-c2ccncc2)cc1-c1cc2ccccc2[nH]1 | O=c1[nH]nc(-c2ccncc2)cc1-c1[nH]c2ccccc2c1I | null | null | CC(=O)C | Functional Group Interconversion | OtherReaction | 0754ae2664ff7ba9610e6f272707033ed8b7278ddd1c23d9264359692cf74d77 | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=c1[nH]nc(-c2ccncc2)cc1-c1cc2ccccc2[nH]1 | O=C1-C-C-C(=O)-N-1-[I;H0;D1;+0:1].[#7;a:2]:[c:3]:[c:4]-[c:5]1:[#7;a:6]:[c:7](:[c:8]):[c:9](:[c:10]):[cH;D2;+0:11]:1>>[#7;a:2]:[c:3]:[c:4]-[c:5]1:[#7;a:6]:[c:7](:[c:8]):[c:9](:[c:10]):[c;H0;D3;+0:11]:1-[I;H0;D1;+0:1] | null | [] | null | null | 3 | HOUR | 577 mg 4-(1H-Indol-2-yl)-6-pyridin-4-yl-2H-pyridazin-3-one is suspended in 30 mL acetone and 550 mg NIS is added. The reaction mixture is stirred for 3 hours at room temperature, the precipitated product isolated by filtration and washed with acetone. The material product is used without further purification
Conditions... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | C1CCNC1.c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1cnncc1.c1ccncc1.c1ccc2[nH]ccc2c1 | HO- | CC(=O)C | null | 3 | O=C1CCC(=O)N1I.O=c1[nH]nc(-c2ccncc2)cc1-c1cc2ccccc2[nH]1>CC(=O)C>O=c1[nH]nc(-c2ccncc2)cc1-c1[nH]c2ccccc2c1I |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4c08ebff04e74637bf2cec2accec9dc6 | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.O=c1[nH]nc(-c2ccncc2)cc1-c1[nH]c2ccccc2c1I>>C=Cc1c(-c2cc(-c3ccncc3)n[nH]c2=O)[nH]c2ccccc12 | IC1=C(NC2=CC=CC=C12)C=1C(NN=C(C1)C1=CC=NC=C1)=O.C(CCC)[Sn](C=C)(CCCC)CCCC.CCOC(=O)C.[F-].[K+]>>N1=CC=C(C=C1)C=1C=C(C(NN1)=O)C=1NC2=CC=CC=C2C1C=C | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH:2]=[CH2:1].I[c:3]1[c:4](-[c:5]2[cH:6][c:7](-[c:8]3[cH:9][cH:10][n:11][cH:12][cH:13]3)[n:14][nH:15][c:16]2=[O:17])[nH:18][c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]12>>[CH2:1]=[CH:2][c:3]1[c:4](-[c:5]2[cH:6][c:7](-[c:8]3[cH:9][cH:10][n:11][cH:12][cH:13]3)[n:14][nH:15][c:16]2=[O:17])[nH:... | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.O=c1[nH]nc(-c2ccncc2)cc1-c1[nH]c2ccccc2c1I | C=Cc1c(-c2cc(-c3ccncc3)n[nH]c2=O)[nH]c2ccccc12 | null | [Cl-].C(C)[N+](CC)(CC)CC.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)C=O | C-C Coupling | Stille reaction_vinyl | f4ad649c74b7a6a35b0e84610492e238d5241d8eaf0ab45cca5db093924b7eac | ec03c739f58696d2a3659a73884744e1a490a20a587da6f115be382b663cf23d | O=c1[nH]nc(-c2ccncc2)cc1-c1cc2ccccc2[nH]1 | C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[CH;D2;+0:1]=[C;D1;H2:2].I-[c;H0;D3;+0:3]1:[c:4](:[c:5]):[c:6](:[c:7]):[#7;a:8]:[c:9]:1-[c:10]:[c:11]:[#7;a:12]>>[#7;a:12]:[c:11]:[c:10]-[c:9]1:[#7;a:8]:[c:6](:[c:7]):[c:4](:[c:5]):[c;H0;D3;+0:3]:1-[CH;D2;+0:1]=[C;D1;H2:2] | null | [] | 80 | CELSIUS | 40 | MINUTE | A mixture of 104 mg 4-(3-Iodo-1H-indol-2-yl)-6-pyridin-4-yl-2H-pyridazin-3-one (example 25), 123 mg tributyl(vinyl)tin, 41 mg tetraethylammonium-chloride and 9 mg bis(triphenylphosphine)palladium(II) chloride in DMF is stirred at 80° C. for 40 min. After cooling to room temperature, 4 ml aqueous potassium fluoride solu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Vinyl.Tin | Vinyl | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1cnncc1.c1ccncc1.c1ccc2[nH]ccc2c1 | HI.Sn | [Cl-].C(C)[N+](CC)(CC)CC.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)C=O | 80 | 0.666667 | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.O=c1[nH]nc(-c2ccncc2)cc1-c1[nH]c2ccccc2c1I>[Cl-].C(C)[N+](CC)(CC)CC.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)C=O>C=Cc1c(-c2cc(-c3ccncc3)n[nH]c2=O)[nH]c2ccccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8e9388745e8c40c88dfe425586cb5534 | COc1nnc(-c2ccncc2)cc1-c1cc2ccc(CO)cc2n1C(=O)OC(C)(C)C>>COc1nnc(-c2ccncc2)cc1-c1cc2ccc(C=O)cc2n1C(=O)OC(C)(C)C | C(C)(C)(C)OC(=O)N1C(=CC2=CC=C(C=C12)CO)C1=C(N=NC(=C1)C1=CC=NC=C1)OC>>C(C)(C)(C)OC(=O)N1C(=CC2=CC=C(C=C12)C=O)C1=C(N=NC(=C1)C1=CC=NC=C1)OC | [CH3:1][O:2][c:3]1[n:4][n:5][c:6](-[c:7]2[cH:8][cH:9][n:10][cH:11][cH:12]2)[cH:13][c:14]1-[c:15]1[cH:16][c:17]2[cH:18][cH:19][c:20]([CH2:21][OH:22])[cH:23][c:24]2[n:25]1[C:26](=[O:27])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32]>>[CH3:1][O:2][c:3]1[n:4][n:5][c:6](-[c:7]2[cH:8][cH:9][n:10][cH:11][cH:12]2)[cH:13][c:14]1-[c:1... | COc1nnc(-c2ccncc2)cc1-c1cc2ccc(CO)cc2n1C(=O)OC(C)(C)C | COc1nnc(-c2ccncc2)cc1-c1cc2ccc(C=O)cc2n1C(=O)OC(C)(C)C | null | [O-2].[Mn+4].[O-2].[O-2].[Mn+4].[O-2] | ClCCl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccc2[nH]c(-c3cnnc(-c4ccncc4)c3)cc2c1 | [#7;a:1]:[c:2]:[c:3]:[c:4](-[CH2;D2;+0:5]-[OH;D1;+0:6]):[c:7]>>[#7;a:1]:[c:2]:[c:3]:[c:4](-[CH;D2;+0:5]=[O;H0;D1;+0:6]):[c:7] | 82 | [{"value": 82.0, "product": "C(C)(C)(C)OC(=O)N1C(=CC2=CC=C(C=C12)C=O)C1=C(N=NC(=C1)C1=CC=NC=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.9, "product": "C(C)(C)(C)OC(=O)N1C(=CC2=CC=C(C=C12)C=O)C1=C(N=NC(=C1)C1=CC=NC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2 g 6-Hydroxymethyl-2-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-indole-1-carboxylic acid tert-butyl ester is dissolved in 46 mL dichloromethane. After addition of 1.61 g activated manganese (IV) oxide the reaction mixture is heated to reflux for 1 hour. Then every two hours additional manganese (IV) oxide is added unti... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccnnc1.c1ccncc1.c1ccc2cc[nH]c2c1 | null | [O-2].[Mn+4].[O-2].[O-2].[Mn+4].[O-2].ClCCl | null | null | COc1nnc(-c2ccncc2)cc1-c1cc2ccc(CO)cc2n1C(=O)OC(C)(C)C>[O-2].[Mn+4].[O-2].[O-2].[Mn+4].[O-2].ClCCl>COc1nnc(-c2ccncc2)cc1-c1cc2ccc(C=O)cc2n1C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-16e15281ca544ab5b7ef7ac523cb9677 | C1CCNCC1.COc1nnc(-c2ccncc2)cc1-c1cc2ccc(C=O)cc2n1C(=O)OC(C)(C)C>>COc1nnc(-c2ccncc2)cc1-c1cc2ccc(CN3CCCCC3)cc2n1C(=O)OC(C)(C)C | C(=O)(O)[O-].[Na+].C(C)(C)(C)OC(=O)N1C(=CC2=CC=C(C=C12)C=O)C1=C(N=NC(=C1)C1=CC=NC=C1)OC.N1CCCCC1.C(=O)=O.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>C(C)(C)(C)OC(=O)N1C(=CC2=CC=C(C=C12)CN1CCCCC1)C1=C(N=NC(=C1)C1=CC=NC=C1)OC | [NH:22]1[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1.O=[CH:21][c:20]1[cH:19][cH:18][c:17]2[cH:16][c:15](-[c:14]3[c:3]([O:2][CH3:1])[n:4][n:5][c:6](-[c:7]4[cH:8][cH:9][n:10][cH:11][cH:12]4)[cH:13]3)[n:30]([C:31](=[O:32])[O:33][C:34]([CH3:35])([CH3:36])[CH3:37])[c:29]2[cH:28]1>>[CH3:1][O:2][c:3]1[n:4][n:5][c:6](-[c:7]2[cH:8... | C1CCNCC1.COc1nnc(-c2ccncc2)cc1-c1cc2ccc(C=O)cc2n1C(=O)OC(C)(C)C | COc1nnc(-c2ccncc2)cc1-c1cc2ccc(CN3CCCCC3)cc2n1C(=O)OC(C)(C)C | null | null | ClCCl.ClC(C)Cl.C(C)(=O)O | Heteroatom Alkylation and Arylation | reductive amination | d0e659bc8d1e29e09a61320b4c537e66ad57335a51368c8bd48de9bdffa59372 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1cc(-c2cc(-c3cc4ccc(CN5CCCCC5)cc4[nH]3)cnn2)ccn1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:9](-[C:8]-[C:7])-[C:10]-[C:11]):[c:3] | 83 | [{"value": 83.0, "product": "C(C)(C)(C)OC(=O)N1C(=CC2=CC=C(C=C12)CN1CCCCC1)C1=C(N=NC(=C1)C1=CC=NC=C1)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 79 mg 6-formyl-2-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-indole-1-carboxylic acid tert-butyl ester is dissolved in 14 mL dichloroethane. 182 mL piperidine and then 0.7 mL acetic acid are added. 334 mg sodium triacetoxyborohydride is added in several portions over 6 hours. Sat. aq. NaHCO3-solution is added and the rea... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccnnc1.c1ccncc1.c1ccc2cc[nH]c2c1.C1CC[NH]CC1 | Other | ClCCl.ClC(C)Cl.C(C)(=O)O | null | null | C1CCNCC1.COc1nnc(-c2ccncc2)cc1-c1cc2ccc(C=O)cc2n1C(=O)OC(C)(C)C>ClCCl.ClC(C)Cl.C(C)(=O)O>COc1nnc(-c2ccncc2)cc1-c1cc2ccc(CN3CCCCC3)cc2n1C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b6617c3e1efe40648bbe980703bbf55d | CCOC(=O)c1cc(-c2ccncc2)n[nH]c1=O.NN>>NNC(=O)c1cc(-c2ccncc2)n[nH]c1=O | C(C)OC(=O)C=1C(NN=C(C1)C1=CC=NC=C1)=O.O.NN>>O=C1NN=C(C=C1C(=O)NN)C1=CC=NC=C1 | CCO[C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][n:11][cH:12][cH:13]2)[n:14][nH:15][c:16]1=[O:17].[NH2:1][NH2:2]>>[NH2:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][n:11][cH:12][cH:13]2)[n:14][nH:15][c:16]1=[O:17] | CCOC(=O)c1cc(-c2ccncc2)n[nH]c1=O.NN | NNC(=O)c1cc(-c2ccncc2)n[nH]c1=O | null | null | C(C)O | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | O=c1ccc(-c2ccncc2)n[nH]1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:[c:8]:1=[O;D1;H0:9].[N;D1;H2:10]-[NH2;D1;+0:11]>>[N;D1;H2:10]-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:[c:8]:1=[O;D1;H0:9] | null | [] | null | null | null | null | 10 g of 3-oxo-6-pyridin-4-yl-2,3-dihydro-pyridazine-4 -carboxylic acid ethyl ester are dissolved in 150 ml of ethanol, 4.2 ml of hydrazine hydrate is added and the mixture is refluxed for 5 hours. After cooling to room temperature, the solid is collected by filtration and dried in vacuo at 40° C.
Conditions: See reacti... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | c1cnncc1.c1ccncc1 | HO- | C(C)O | null | null | CCOC(=O)c1cc(-c2ccncc2)n[nH]c1=O.NN>C(C)O>NNC(=O)c1cc(-c2ccncc2)n[nH]c1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9975cf0fb56142daa5f77fd28abbd97c | CC(N)=S.NNC(=O)c1cc(-c2ccncc2)n[nH]c1=O>>Cc1nnc(-c2cc(-c3ccncc3)n[nH]c2=O)[nH]1 | O=C1NN=C(C=C1C(=O)NN)C1=CC=NC=C1.C(C)(=S)N.C(C)N(CC)CC.N1=CC=CC=C1>>CC=1NC(=NN1)C=1C(NN=C(C1)C1=CC=NC=C1)=O | S=[C:2]([CH3:1])[NH2:19].O=[C:5]([NH:4][NH2:3])[c:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][n:12][cH:13][cH:14]2)[n:15][nH:16][c:17]1=[O:18]>>[CH3:1][c:2]1[n:3][n:4][c:5](-[c:6]2[cH:7][c:8](-[c:9]3[cH:10][cH:11][n:12][cH:13][cH:14]3)[n:15][nH:16][c:17]2=[O:18])[nH:19]1 | CC(N)=S.NNC(=O)c1cc(-c2ccncc2)n[nH]c1=O | Cc1nnc(-c2cc(-c3ccncc3)n[nH]c2=O)[nH]1 | null | null | C(CCC)O | Aromatic Heterocycle Formation | OtherReaction | 22397ef88a4b6ba0343586e53e3e20e2055f46904a3043f30a9bf08906917011 | 1e7b5d45c28f5d1767d2abb0c78792aee2714d99002ea329b67f9a89a7e53301 | O=c1[nH]nc(-c2ccncc2)cc1-c1nnc[nH]1 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[NH2;D1;+0:3])-[c;H0;D3;+0:4]1:[c:5]:[c:6](-[c:7]):[#7;a:8]:[#7;a:9]:[c:10]:1=[O;D1;H0:11].S=[C;H0;D3;+0:12](-[C;D1;H3:13])-[NH2;D1;+0:14]>>[C;D1;H3:13]-[c;H0;D3;+0:12]1:[n;H0;D2;+0:3]:[n;H0;D2;+0:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:4]2:[c:5]:[c:6](-[c:7]):[#7;a:8]:[#7;a:9]:[c:10]:2=[O;D1;H0:1... | null | [] | null | null | null | null | A mixture of 100 mg of 3-oxo-6-pyridin-4-yl-2,3-dihydro-pyridazine-4-carboxylic acid hydrazide, 130 mg thioacetamide, 87 mg triethylamine, 1 ml of pyridine and 5 ml of butanol is refluxed for 15 hours. After cooling and stirring at room temperature, a solid precipitated is collected by filtration, washed with cold isop... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Thioamide | null | null | c1nc[nH]n1 | c1nc[nH]n1.c1cnncc1.c1ccncc1 | Other | C(CCC)O | null | null | CC(N)=S.NNC(=O)c1cc(-c2ccncc2)n[nH]c1=O>C(CCC)O>Cc1nnc(-c2cc(-c3ccncc3)n[nH]c2=O)[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7bf3e54ab9a1423e8dedda95b8b729dc | COC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.COc1nnc(-c2ccncc2)cc1-c1cc2ccc(C=O)cc2n1C(=O)OC(C)(C)C>>COC=Cc1ccc2cc(-c3cc(-c4ccncc4)nnc3OC)n(C(=O)OC(C)(C)C)c2c1 | C(C)(C)(C)OC(=O)N1C(=CC2=CC=C(C=C12)C=O)C1=C(N=NC(=C1)C1=CC=NC=C1)OC.[Cl-].COC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C(CCC)[Li]>>C(C)(C)(C)OC(=O)N1C(=CC2=CC=C(C=C12)C=COC)C1=C(N=NC(=C1)C1=CC=NC=C1)OC | c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:3][O:2][CH3:1])cc1.O=[CH:4][c:5]1[cH:6][cH:7][c:8]2[cH:9][c:10](-[c:11]3[cH:12][c:13](-[c:14]4[cH:15][cH:16][n:17][cH:18][cH:19]4)[n:20][n:21][c:22]3[O:23][CH3:24])[n:25]([C:26](=[O:27])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32])[c:33]2[cH:34]1>>[CH3:1][O:2][CH:3]=[CH:4][c:5]1[cH:6][cH:... | COC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.COc1nnc(-c2ccncc2)cc1-c1cc2ccc(C=O)cc2n1C(=O)OC(C)(C)C | COC=Cc1ccc2cc(-c3cc(-c4ccncc4)nnc3OC)n(C(=O)OC(C)(C)C)c2c1 | null | null | C1CCOC1 | C-C Coupling | Wittig with Phosphonium | 1b762435fe6b580b808a6e9f0dae00ddd254c0b88d607d21a223e11776d2e3a4 | bf4569804906d66c98adaac7df334e96eee508d45c26c621eb5069c3e4f1df77 | c1ccc2[nH]c(-c3cnnc(-c4ccncc4)c3)cc2c1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6].[C;D1;H3:7]-[#8:8]-[CH2;D2;+0:9]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[CH;D2;+0:1]=[CH;D2;+0:9]-[#8:8]-[C;D1;H3:7]):[c:3] | null | [] | -78 | CELSIUS | 30 | MINUTE | 1.23 g methoxymethyltriphenylphoshonium chloride is suspended in 10 mL THF and cooled to −78° C. 2.20 mL butyllithium (1.6 M in hexanes) is added dropwise and the resulting mixture is stirred for 30 min at −78° C. and then warmed in an ice bath to 0° C. After addition of a solution of 734 mg 6-formyl-2-(3-methoxy-6-pyr... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ether | Ether | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccc2cc[nH]c2c1.c1ccnnc1.c1ccncc1 | HO- | C1CCOC1 | -78 | 0.5 | COC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.COc1nnc(-c2ccncc2)cc1-c1cc2ccc(C=O)cc2n1C(=O)OC(C)(C)C>C1CCOC1>COC=Cc1ccc2cc(-c3cc(-c4ccncc4)nnc3OC)n(C(=O)OC(C)(C)C)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-88b4576dce994509ad8426d3567f2f13 | COC=Cc1ccc2cc(-c3cc(-c4ccncc4)nnc3OC)n(C(=O)OC(C)(C)C)c2c1>>COc1nnc(-c2ccncc2)cc1-c1cc2ccc(CC=O)cc2n1C(=O)OC(C)(C)C | C(C)(C)(C)OC(=O)N1C(=CC2=CC=C(C=C12)C=COC)C1=C(N=NC(=C1)C1=CC=NC=C1)OC.[I-].[K+].Cl[Si](C)(C)C>>C(C)(C)(C)OC(=O)N1C(=CC2=CC=C(C=C12)CC=O)C1=C(N=NC(=C1)C1=CC=NC=C1)OC | C[O:23][CH:22]=[CH:21][c:20]1[cH:19][cH:18][c:17]2[cH:16][c:15](-[c:14]3[c:3]([O:2][CH3:1])[n:4][n:5][c:6](-[c:7]4[cH:8][cH:9][n:10][cH:11][cH:12]4)[cH:13]3)[n:26]([C:27](=[O:28])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33])[c:25]2[cH:24]1>>[CH3:1][O:2][c:3]1[n:4][n:5][c:6](-[c:7]2[cH:8][cH:9][n:10][cH:11][cH:12]2)[cH:13][... | COC=Cc1ccc2cc(-c3cc(-c4ccncc4)nnc3OC)n(C(=O)OC(C)(C)C)c2c1 | COc1nnc(-c2ccncc2)cc1-c1cc2ccc(CC=O)cc2n1C(=O)OC(C)(C)C | null | null | C(C)#N | Miscellaneous | OtherReaction | c341fdc42e48cf7e12789f1fb10a9c65f84ba2f1b42598f190b56c95d40c7caa | f3a920ec0ed1e7a5c2088300ae22a9e2e42203bc8efef555e3e9c02778626f07 | c1ccc2[nH]c(-c3cnnc(-c4ccncc4)c3)cc2c1 | C-[O;H0;D2;+0:1]-[CH;D2;+0:2]=[CH;D2;+0:3]-[c:4](:[c:5]):[c:6]:[c:7]:[#7;a:8]>>[#7;a:8]:[c:7]:[c:6]:[c:4](-[CH2;D2;+0:3]-[CH;D2;+0:2]=[O;H0;D1;+0:1]):[c:5] | 114.6 | [{"value": 114.6, "product": "C(C)(C)(C)OC(=O)N1C(=CC2=CC=C(C=C12)CC=O)C1=C(N=NC(=C1)C1=CC=NC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 180 mg 6-(2-methoxyvinyl)-2-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-indole-1-carboxylic acid tert-butyl ester are dissolved in 10 mL acetonitrile. Then 196 mg potassium iodide and 125 μL chlorotrimethylsilane are added. The reaction mixture is stirred for 2 hours at rt. The solvent is removed in vacuo and the obtaine... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aldehyde | null | null | c1ccnnc1.c1ccncc1.c1ccc2cc[nH]c2c1 | Other | C(C)#N | null | 2 | COC=Cc1ccc2cc(-c3cc(-c4ccncc4)nnc3OC)n(C(=O)OC(C)(C)C)c2c1>C(C)#N>COc1nnc(-c2ccncc2)cc1-c1cc2ccc(CC=O)cc2n1C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ae220e267c754d6f871b184be7eb4cda | C1COCCN1.CC(C)(C)OC(=O)n1c(-c2cc(-c3ccncc3)n[nH]c2=O)cc2ccc(CC=O)cc21.COc1nnc(-c2ccncc2)cc1-c1cc2ccc(CC=O)cc2n1C(=O)OC(C)(C)C>>CC(C)(C)OC(=O)n1c(-c2cc(-c3ccncc3)n[nH]c2=O)cc2ccc(CCC3CCCCN3)cc21 | C(=O)(O)[O-].[Na+].C(=O)=O.N1CCOCC1.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+].C(C)(C)(C)OC(=O)N1C(=CC2=CC=C(C=C12)CC=O)C1=C(N=NC(=C1)C1=CC=NC=C1)OC.C(C)(C)(C)OC(=O)N1C(=CC2=CC=C(C=C12)CC=O)C=1C(NN=C(C1)C1=CC=NC=C1)=O>>C(C)(C)(C)OC(=O)N1C(=CC2=CC=C(C=C12)CCC1NCCCC1)C=1C(NN=C(C1)C1=CC=NC=C1)=O | O1[CH2:31][CH2:30][NH:35][CH2:34][CH2:33]1.O=[CH:29][CH2:28][c:27]1[cH:26][cH:25][c:24]2[cH:23][c:9](-[c:10]3[cH:11][c:12](-[c:13]4[cH:14][cH:15][n:16][cH:17][cH:18]4)[n:19][nH:20][c:21]3=[O:22])[n:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[c:37]2[cH:36]1.COc1nnc(-c2ccn[cH:32]c2)cc1-c1cc2ccc(CC=O)cc2n1C(=O)OC... | C1COCCN1.CC(C)(C)OC(=O)n1c(-c2cc(-c3ccncc3)n[nH]c2=O)cc2ccc(CC=O)cc21.COc1nnc(-c2ccncc2)cc1-c1cc2ccc(CC=O)cc2n1C(=O)OC(C)(C)C | CC(C)(C)OC(=O)n1c(-c2cc(-c3ccncc3)n[nH]c2=O)cc2ccc(CCC3CCCCN3)cc21 | null | null | ClCCl.ClC(C)Cl.C(C)(=O)O | C-C Coupling | OtherReaction | a135ff1e65bd5b14a2374c578f9ed1943f615e583da5eed342dd0f111218ee05 | 5b03a5b9e4b0906e57b3451f053f1aa86667b6e59f1733c15a6fe7ccbeb48e6f | O=c1[nH]nc(-c2ccncc2)cc1-c1cc2ccc(CCC3CCCCN3)cc2[nH]1 | C-O-c1:n:n:c(-c2:c:[cH;D2;+0:1]:n:c:c:2):c:c:1-c1:c:c2:c:c:c(-C-C=O):c:c:2:n:1-C(=O)-O-C(-C)(-C)-C.O1-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[#7:4]-[C:5]-[CH2;D2;+0:6]-1.O=[CH;D2;+0:7]-[C:8]-[c:9]>>[c:9]-[C:8]-[CH2;D2;+0:7]-[CH;D3;+0:3]1-[#7:4]-[C:5]-[CH2;D2;+0:6]-[CH2;D2;+0:1]-[CH2;D2;+0:2]-1 | null | [] | null | null | null | null | 54 mg of a mixture of 6-(2-oxoethyl)-2-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-indole-1-carboxylic acid tert-butyl ester and 6-(2-oxoethyl)-2-(3-Oxo-6-pyridin-4-yl-2,3-dihydro-pyridazin-4-yl)indole-1-carboxylic acid tert-butyl ester are dissolved in 9 mL dichloroethane. 160 μL morpholine and then 0.46 mL acetic acid ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Aldehyde.Ether.Ether.Ether.Boc | null | C1COCCN1.c1ccnnc1.c1ccncc1.c1ccc2[nH]ccc2c1 | C1CCNCC1 | c1cnncc1.c1ccncc1.c1ccc2cc[nH]c2c1.C1CCNCC1 | HO- | ClCCl.ClC(C)Cl.C(C)(=O)O | null | null | C1COCCN1.CC(C)(C)OC(=O)n1c(-c2cc(-c3ccncc3)n[nH]c2=O)cc2ccc(CC=O)cc21.COc1nnc(-c2ccncc2)cc1-c1cc2ccc(CC=O)cc2n1C(=O)OC(C)(C)C>ClCCl.ClC(C)Cl.C(C)(=O)O>CC(C)(C)OC(=O)n1c(-c2cc(-c3ccncc3)n[nH]c2=O)cc2ccc(CCC3CCCCN3)cc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dbbb1c6c81804f80891a6abbf08e6b2f | CC(=O)c1cccc(OB(O)O)c1.CCc1cccc(C(=O)O)c1Br>>CCOC(=O)c1ccccc1-c1cccc(C(C)=O)c1 | C(C)C=1C(=C(C(=O)O)C=CC1)Br.C(C)(=O)C=1C=C(C=CC1)OB(O)O.C(OC)COC.C([O-])(O)=O.[Na+].C([O-])([O-])=O.[Na+].[Na+]>>C(C)OC(=O)C=1C(=CC=CC1)C1=CC(=CC=C1)C(C)=O | OB(O)O[c:12]1[cH:13][cH:14][cH:15][c:16]([C:17]([CH3:18])=[O:19])[cH:20]1.Br[c:11]1[c:6]([C:4]([OH:3])=[O:5])[cH:7][cH:8][cH:9][c:10]1[CH2:2][CH3:1]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1-[c:12]1[cH:13][cH:14][cH:15][c:16]([C:17]([CH3:18])=[O:19])[cH:20]1 | CC(=O)c1cccc(OB(O)O)c1.CCc1cccc(C(=O)O)c1Br | CCOC(=O)c1ccccc1-c1cccc(C(C)=O)c1 | null | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 1c8c48036a0f06e6ffc9673466d4bff5319e6174ce2f1a0d2bea2aab2e9cd80f | 169f4e097ffba4530d9f6d9673651b55f261578d3ebd32e9612e5b32deecfd8e | c1ccc(-c2ccccc2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2](-[C:3](=[O;D1;H0:4])-[OH;D1;+0:5]):[c:6]:[c:7]:[c:8]:[c;H0;D3;+0:9]:1-[CH2;D2;+0:10]-[C;D1;H3:11].O-B(-O)-O-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]-[C:17](-[C;D1;H3:18])=[O;D1;H0:19]>>[C;D1;H3:18]-[C:17](=[O;D1;H0:19])-[c:16]:[c:15]:[c;H0;D3;+0:12](-[c;H0;D3;+0:1]1:[cH;D2;+0:9]:[c:8]:[c:7... | 95 | [{"value": 95.0, "product": "C(C)OC(=O)C=1C(=CC=CC1)C1=CC(=CC=C1)C(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of ethyl 2-bromobenzoic acid (10.0 g) and 3-acetylphenylboric acid (7.87 g) in dimethoxyethane (200 ml) was added 2 N sodium carbonate solution (50 ml), and the mixture was deaerated and argon-substituted. To this mixture was added tetrakis(triphenylphosphine) palladium (0) (5.04 g), and the mixture was... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carboxylic acid | Ester | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | HBr.B | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)(=O)OCC | null | null | CC(=O)c1cccc(OB(O)O)c1.CCc1cccc(C(=O)O)c1Br>[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)(=O)OCC>CCOC(=O)c1ccccc1-c1cccc(C(C)=O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-246bbab43f254048a1c6b8ae5710095b | CC(C)(C)OC(=O)NCCN.CC(NC1CCN(Cc2ccccc2)CC1)c1cccc(-c2ccccc2C(=O)NCCNC(=O)OC(C)(C)C)c1.CCN=C=NCCCN(C)C.CN(C)C=O.On1nnc2ccccc21>>CC(c1cccc(-c2ccccc2C(=O)NCCNC(=O)OC(C)(C)C)c1)N(C(=O)Cc1ccc2ccccc2c1)C1CCN(Cc2ccccc2)CC1 | CCN=C=NCCCN(C)C.C(C1=CC=CC=C1)N1CCC(CC1)NC(C)C=1C=C(C=CC1)C=1C(=CC=CC1)C(=O)NCCNC(=O)OC(C)(C)C.C(C)(C)(C)OC(NCCN)=O.C=1C=CC2=C(C1)N=NN2O.CN(C)C=O>>C(C1=CC=CC=C1)N1CCC(CC1)N(C(CC1=CC2=CC=CC=C2C=C1)=O)C(C)C=1C=C(C=CC1)C=1C(=CC=CC1)C(=O)NCCNC(=O)OC(C)(C)C | C[C:32](OC(=O)NCCN)([CH3:33])[CH3:41].[CH3:1][CH:2]([c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[C:14](=[O:15])[NH:16][CH2:17][CH2:18][NH:19][C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[cH:27]1)[NH:28][CH:42]1[CH2:43][CH2:44][N:45]([CH2:46][c:47]2[cH:48][cH:49][cH:50][cH:51][cH:52... | CC(C)(C)OC(=O)NCCN.CC(NC1CCN(Cc2ccccc2)CC1)c1cccc(-c2ccccc2C(=O)NCCNC(=O)OC(C)(C)C)c1.CCN=C=NCCCN(C)C.CN(C)C=O.On1nnc2ccccc21 | CC(c1cccc(-c2ccccc2C(=O)NCCNC(=O)OC(C)(C)C)c1)N(C(=O)Cc1ccc2ccccc2c1)C1CCN(Cc2ccccc2)CC1 | null | null | C([O-])(O)=O.[Na+].C(C)N(CC)CC | Acylation | OtherReaction | 4fdacd17504eb9e80ea86f61c59068935c60b7876057a860926c772402aa7434 | 858d275fb1dd4d064077f2884ff6972234e8a0ea65372d1e70759265e87e0c43 | O=C(Cc1ccc2ccccc2c1)N(Cc1cccc(-c2ccccc2)c1)C1CCN(Cc2ccccc2)CC1 | C-N(-C)-C-C-C-N=[C;H0;D2;+0:1]=N-C-[CH3;D1;+0:2].C-N(-C)-[CH;D2;+0:3]=[O;D1;H0:4].C-[C;H0;D4;+0:5](-[CH3;D1;+0:6])(-[CH3;D1;+0:7])-O-C(=O)-N-C-C-N.O-n1:n:n:[c;H0;D3;+0:8]2:[c:9]:[c:10]:[c:11]:[c:12]:[c;H0;D3;+0:13]:2:1.[C:14]-[C:15](-[NH;D2;+0:16]-[C:17](-[C;D1;H3:18])-[c:19])-[C:20]>>[C:14]-[C:15](-[N;H0;D3;+0:16](-[C... | null | [] | null | null | 18 | HOUR | To a solution of the compound obtained in Reference Example 3 (1.20 g) in DMF (40 ml) were added N-(2-aminoethyl)carbamic acid tert-butyl ester (310 mg), HOBt (262 mg) and triethylamine (196 mg). WSC (372 mg) was further added to this mixture under ice-cooling, and the mixture was stirred for 18 hours at room temperatu... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Tertiary amide.Primary amine.Secondary amine.Tertiary amine.Boc | Tertiary amide | c1ccc2[nH]nnc2c1 | c1ccc2ccccc2c1 | c1ccccc1.c1ccccc1.c1ccc2ccccc2c1.C1CC[NH]CC1.c1ccccc1 | HO- | C([O-])(O)=O.[Na+].C(C)N(CC)CC | null | 18 | CC(C)(C)OC(=O)NCCN.CC(NC1CCN(Cc2ccccc2)CC1)c1cccc(-c2ccccc2C(=O)NCCNC(=O)OC(C)(C)C)c1.CCN=C=NCCCN(C)C.CN(C)C=O.On1nnc2ccccc21>C([O-])(O)=O.[Na+].C(C)N(CC)CC>CC(c1cccc(-c2ccccc2C(=O)NCCNC(=O)OC(C)(C)C)c1)N(C(=O)Cc1ccc2ccccc2c1)C1CCN(Cc2ccccc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d8d8511fd6714c77bb469f6797f331c4 | NCc1ccccc1Br>>CC(C)(C)OC(=O)NCc1ccccc1Br | Cl.BrC1=C(CN)C=CC=C1.C([O-])(O)=O.[Na+]>>C(C)(C)(C)OC(NCC1=C(C=CC=C1)Br)=O | [cH:1]1[cH:12][cH:11][c:10]([CH2:9][NH2:8])[c:15]([Br:16])[cH:14]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[Br:16] | NCc1ccccc1Br | CC(C)(C)OC(=O)NCc1ccccc1Br | null | null | O.C(C)(=O)OCC | Functional Group Addition | OtherReaction | 7ebc72dfbd368f2957e1d9209ce0e4f43e00e1e6eb015c59f70700923a5b5214 | 787734300905392fc3f0ea9fb3cf35858edc27da77afa0faeeb2270fd92e7178 | c1ccccc1 | [Br;D1;H0:1]-[c:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[c:6]:[c:7]:1-[C:8]-[NH2;D1;+0:9]>>[Br;D1;H0:1]-[c:2]1:[cH;D2;+0:3]:[c:10]:[cH;D2;+0:5]:[c:6]:[c:7]:1-[C:8]-[NH;D2;+0:9]-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[CH3;D1;+0:4] | 95 | [{"value": 95.0, "product": "C(C)(C)(C)OC(NCC1=C(C=CC=C1)Br)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a solution of 2-bromobenzylamine hydrochloride (5.00 g) and di-tert-butoxycarbonyl (5.39 g) in ethyl acetate (30 ml) was added saturated sodium bicarbonate solution (30 ml), and stirred at room temperature for 16 hours. The obtained reaction mixture was diluted with water, and extracted with ethyl acetate. The organ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Carbamic ester.Ether.Boc | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | O.C(C)(=O)OCC | null | 16 | NCc1ccccc1Br>O.C(C)(=O)OCC>CC(C)(C)OC(=O)NCc1ccccc1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-48f5b29454ff4ffa8f8e635f369abe30 | CC(C)(C)OC(=O)NCCC(=O)O.Nc1ccccc1Br>>CC(C)(C)OC(=O)NCCCC(=O)Nc1ccccc1Br | C(C)(C)(C)OC(=O)NCCC(=O)O.N1=CC=CC=C1.C(C(=O)Cl)(=O)Cl.BrC1=C(N)C=CC=C1>>BrC1=C(C=CC=C1)NC(=O)CCCNC(=O)OC(C)(C)C | O[C:11]([CH2:10][CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])=[O:13].[NH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][c:20]1[Br:21]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH2:11][C:12](=[O:13])[NH:14][c:15]1[cH:16][cH:17][cH:18][cH:19][c:20]1[Br:21] | CC(C)(C)OC(=O)NCCC(=O)O.Nc1ccccc1Br | CC(C)(C)OC(=O)NCCCC(=O)Nc1ccccc1Br | null | CN(C)C=O.CN(C1=CC=NC=C1)C | C(C)#N.C([O-])(O)=O.[Na+].C(C)N(CC)CC.C1CCOC1 | Acylation | OtherReaction | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[C:3]-[CH2;D2;+0:1]-[C:9](=[O;H0;D1;+0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 18 | [{"value": 18.0, "product": "BrC1=C(C=CC=C1)NC(=O)CCCNC(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 3-(tert-butoxycarbonylamino)propionic acid (4.3 g) and pyridine (3.6 ml) in THF (40 ml) were added oxalyl chloride (3.0 ml) and DMF(3 drops) under ice-cooling, and the mixture was stirred at room temperature for 1 hour. To the obtained reaction solution were added o-bromoaniline (2.6 g), triethylamine ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1 | null | CN(C)C=O.CN(C1=CC=NC=C1)C.C(C)#N.C([O-])(O)=O.[Na+].C(C)N(CC)CC.C1CCOC1 | null | 1 | CC(C)(C)OC(=O)NCCC(=O)O.Nc1ccccc1Br>CN(C)C=O.CN(C1=CC=NC=C1)C.C(C)#N.C([O-])(O)=O.[Na+].C(C)N(CC)CC.C1CCOC1>CC(C)(C)OC(=O)NCCCC(=O)Nc1ccccc1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e29922bd31954e4c9a42c73495a770ab | CC(c1cccc(-c2ccccc2CN)c1)N(C(=O)Cc1ccc(Cl)cc1)C1CCN(Cc2ccccc2)CC1.Cl.NC(=O)CCl>>CC(c1cccc(-c2ccccc2CNCC(N)=O)c1)N(C(=O)Cc1ccc(Cl)cc1)C1CCN(Cc2ccccc2)CC1.Cl | Cl.Cl.Cl.NCC1=C(C=CC=C1)C1=CC(=CC=C1)C(C)N(C(CC1=CC=C(C=C1)Cl)=O)C1CCN(CC1)CC1=CC=CC=C1.ClCC(=O)N.C([O-])([O-])=O.[K+].[K+]>>Cl.Cl.C(C1=CC=CC=C1)N1CCC(CC1)N(C(CC1=CC=C(C=C1)Cl)=O)C(C)C=1C=C(C=CC1)C1=C(C=CC=C1)CNCC(=O)N | [CH3:1][CH:2]([c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[CH2:14][NH2:15])[cH:20]1)[N:21]([C:22](=[O:23])[CH2:24][c:25]1[cH:26][cH:27][c:28]([Cl:29])[cH:30][cH:31]1)[CH:32]1[CH2:33][CH2:34][N:35]([CH2:36][c:37]2[cH:38][cH:39][cH:40][cH:41][cH:42]2)[CH2:43][CH2:44]1.[ClH:46].Cl[CH2:16][C:17](... | CC(c1cccc(-c2ccccc2CN)c1)N(C(=O)Cc1ccc(Cl)cc1)C1CCN(Cc2ccccc2)CC1.Cl.NC(=O)CCl | CC(c1cccc(-c2ccccc2CNCC(N)=O)c1)N(C(=O)Cc1ccc(Cl)cc1)C1CCN(Cc2ccccc2)CC1.Cl | null | null | C([O-])(O)=O.[Na+].CCOCC.C(C)#N.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | O=C(Cc1ccccc1)N(Cc1cccc(-c2ccccc2)c1)C1CCN(Cc2ccccc2)CC1 | Cl-[CH2;D2;+0:1]-[C:2](-[N;D1;H2:3])=[O;D1;H0:4].[NH2;D1;+0:5]-[C:6]-[c:7]>>[N;D1;H2:3]-[C:2](=[O;D1;H0:4])-[CH2;D2;+0:1]-[NH;D2;+0:5]-[C:6]-[c:7] | 77 | [{"value": 77.0, "product": "Cl.Cl.C(C1=CC=CC=C1)N1CCC(CC1)N(C(CC1=CC=C(C=C1)Cl)=O)C(C)C=1C=C(C=CC1)C1=C(C=CC=C1)CNCC(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 72 | HOUR | To a solution of the compound obtained in Example 43 (100 mg) in acetonitrile (10 ml) was added 2-chloroacetic acid amide (22 mg) and potassium carbonate (66 mg), and the mixture was stirred at room temperature for 72 hours, and at 60° C. for 6 hours. The reaction mixture was diluted with saturated sodium bicarbonate (... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CC[NH]CC1.c1ccccc1 | HCl | C([O-])(O)=O.[Na+].CCOCC.C(C)#N.C(C)(=O)OCC | null | 72 | CC(c1cccc(-c2ccccc2CN)c1)N(C(=O)Cc1ccc(Cl)cc1)C1CCN(Cc2ccccc2)CC1.Cl.NC(=O)CCl>C([O-])(O)=O.[Na+].CCOCC.C(C)#N.C(C)(=O)OCC>CC(c1cccc(-c2ccccc2CNCC(N)=O)c1)N(C(=O)Cc1ccc(Cl)cc1)C1CCN(Cc2ccccc2)CC1.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ad4a09b75ec84bed8558cde3ba78f108 | ClCl.O=S([O-])c1ccccc1>>O=S(=O)(Cl)c1ccccc1 | ClCl.C1(=CC=CC=C1)S(=O)[O-].[Na+].C1(=CC=CC=C1)S(=O)[O-].C1(=CC=CC=C1)C>>C1(=CC=CC=C1)S(=O)(=O)Cl | Cl[Cl:4].[O-:1][S:2](=[O:3])[c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1>>[O:1]=[S:2](=[O:3])([Cl:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1 | ClCl.O=S([O-])c1ccccc1 | O=S(=O)(Cl)c1ccccc1 | null | null | O | Functional Group Interconversion | OtherReaction | 03debb230351596239cbc9a8ae249800b74565d1aa45c11b464d4b120a8250ec | 3855ae08274369907addf9929af01c270ce61e1e09fc64d8a51fac7fbb45a76b | c1ccccc1 | Cl-[Cl;H0;D1;+0:1].[O-;H0;D1:2]-[S;H0;D3;+0:3](=[O;D1;H0:4])-[c:5](:[c:6]):[c:7]>>[Cl;H0;D1;+0:1]-[S;H0;D4;+0:3](=[O;D1;H0:4])(=[O;H0;D1;+0:2])-[c:5](:[c:6]):[c:7] | 133.1 | [{"value": 93.9, "product": "C1(=CC=CC=C1)S(=O)(=O)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 133.1, "product": "C1(=CC=CC=C1)S(=O)(=O)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A reactor was charged with 29.3 g of sodium benzenesulfinate (0.14 mole) obtained by the fourth step, and the benzenesulfinate was dissolved in 65 mL of water. Then, 105 mL of toluene was charged, and 10.3 g (0.1456 mole, 1.04 times moles) of chlorine was, little by little, blown into the reactor at a temperature of 18... | 10.6084/m9.figshare.5104873.v1 | null | null | Sulfonyl halide | null | null | c1ccccc1 | Other | O | null | null | ClCl.O=S([O-])c1ccccc1>O>O=S(=O)(Cl)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-18aca290182c4aa0a2257fc9e441bb3d | BrBr.O=S([O-])c1ccccc1>>O=S(=O)(Br)c1ccccc1 | C1(=CC=CC=C1)S(=O)[O-].[Na+].BrBr>>C1(=CC=CC=C1)S(=O)(=O)Br | Br[Br:4].[O-:1][S:2](=[O:3])[c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1>>[O:1]=[S:2](=[O:3])([Br:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1 | BrBr.O=S([O-])c1ccccc1 | O=S(=O)(Br)c1ccccc1 | null | null | null | Functional Group Interconversion | OtherReaction | 03debb230351596239cbc9a8ae249800b74565d1aa45c11b464d4b120a8250ec | 3855ae08274369907addf9929af01c270ce61e1e09fc64d8a51fac7fbb45a76b | c1ccccc1 | Br-[Br;H0;D1;+0:1].[O-;H0;D1:2]-[S;H0;D3;+0:3](=[O;D1;H0:4])-[c:5](:[c:6]):[c:7]>>[Br;H0;D1;+0:1]-[S;H0;D4;+0:3](=[O;D1;H0:4])(=[O;H0;D1;+0:2])-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | Benzenesulfonyl bromide was synthesized with 1316.0 g of the mother liquid containing sodium benzenesulfinate by procedures similar to those of the fourth step and the fifth step of Example 1 except that bromine was used instead of chlorine in the fifth step. Thus, 36.0 g of benzenesulfonyl bromide was yielded. Gas chr... | 10.6084/m9.figshare.5104873.v1 | null | null | Sulfonyl halide | null | null | c1ccccc1 | Br- | null | null | null | BrBr.O=S([O-])c1ccccc1>>O=S(=O)(Br)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8c8d4afcbe4e4f69bad780bdcf58c27e | O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3>>O=P(O)(O)O | O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3.N1=C(N)N=C(N)N=C1N>>P(=O)(O)(O)O.N1=C(N)N=C(N)N=C1N | O=P12OP3(=O)OP(=O)(O1)[O:14][P:11](=[O:10])([O:12]2)[O:13]3>>[O:10]=[P:11]([OH:12])([OH:13])[OH:14] | O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3 | O=P(O)(O)O | null | null | null | Reduction | OtherReaction | be33e0461de99a67340dcc65697c47721b35c23585c71f3b6499cfaa484c58ac | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | null | O=P12-O-P3(=O)-O-P(=O)(-O-1)-[O;H0;D2;+0:1]-[#15:2](=[O;D1;H0:3])(-[O;H0;D2;+0:4]-2)-[O;H0;D2;+0:5]-3>>[O;D1;H0:3]=[#15:2](-[OH;D1;+0:4])(-[OH;D1;+0:5])-[OH;D1;+0:1] | null | [] | null | null | null | null | Under atmosphere, charged in a twin-screw extruder were 70.97 g (0.5 moles) of diphosphorus pentoxide and 126.06 g (1.0 moles) of melamine (commercial name: Chang Chun Melamine), and a bar like product was formed at the extrusion temperature of 340° C. After being cooled, the bar like product is pulverized, thereby a p... | 10.6084/m9.figshare.5104873.v1 | null | null | null | O1P2OP3OP1OP(O2)O3 | null | null | Other | null | null | null | O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3>>O=P(O)(O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-03b8a4bd98cb48cebc60c1aa63086a6b | O=C(O)CCC/C=C\C[C@@H]1[C@@H](COc2cc(Cl)cc(Cl)c2)[C@H](O)C[C@H]1Cl.OCCO>>O=C(CCC/C=C\C[C@@H]1[C@@H](COc2cc(Cl)cc(Cl)c2)[C@H](O)C[C@H]1Cl)OCCO | C(C)N(CC)CC.ClC(=O)OCC.Cl[C@@H]1C[C@H]([C@@H]([C@H]1C\C=C/CCCC(=O)O)COC1=CC(=CC(=C1)Cl)Cl)O.C(C)N(CC)CC.C(CO)O>>OCCOC(CCC\C=C/C[C@@H]1[C@H]([C@@H](C[C@H]1Cl)O)COC1=CC(=CC(=C1)Cl)Cl)=O | [O:1]=[C:2]([CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8][C@@H:9]1[C@@H:10]([CH2:11][O:12][c:13]2[cH:14][c:15]([Cl:16])[cH:17][c:18]([Cl:19])[cH:20]2)[C@H:21]([OH:22])[CH2:23][C@H:24]1[Cl:25])[OH:26].O[CH2:27][CH2:28][OH:29]>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8][C@@H:9]1[C@@H:10]([CH2:11][O:12][c:13]2[... | O=C(O)CCC/C=C\C[C@@H]1[C@@H](COc2cc(Cl)cc(Cl)c2)[C@H](O)C[C@H]1Cl.OCCO | O=C(CCC/C=C\C[C@@H]1[C@@H](COc2cc(Cl)cc(Cl)c2)[C@H](O)C[C@H]1Cl)OCCO | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | Esterification of Carboxylic Acids | 3f9a9ace480b666da05fcfe5450d12b5c1ea5b0d435c195e1dd4bd20281604bb | dcbf04ec563ed0e9dfc79070490a028958024079a671c385858bb18cc8ec995a | c1ccc(OCC2CCCC2)cc1 | O-[CH2;D2;+0:1]-[C:2]-[O;D1;H1:3].[C:4]-[C:5](=[O;D1;H0:6])-[OH;D1;+0:7]>>[C:4]-[C:5](=[O;D1;H0:6])-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[C:2]-[O;D1;H1:3] | 22 | [{"value": 22.0, "product": "OCCOC(CCC\\C=C/C[C@@H]1[C@H]([C@@H](C[C@H]1Cl)O)COC1=CC(=CC(=C1)Cl)Cl)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | Triethylamine (15 μL, 0.11 mmol) and ethyl chloroformate (15 μL, 0.16 mmol) were added sequentially to a solution of (Z)-7-[(1R,2S,3R,5R)-5-chloro-2-(3,5-dichloro-phenoxymethyl)-3-hydroxy-cyclopentyl]-hept-5-enoic acid (U.S. Provisional Patent Application No. 60/644,069, filed on Jan. 14, 2005, incorporated by referenc... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | C1CCCC1.c1ccccc1 | HO- | C(Cl)Cl | null | 2.5 | O=C(O)CCC/C=C\C[C@@H]1[C@@H](COc2cc(Cl)cc(Cl)c2)[C@H](O)C[C@H]1Cl.OCCO>C(Cl)Cl>O=C(CCC/C=C\C[C@@H]1[C@@H](COc2cc(Cl)cc(Cl)c2)[C@H](O)C[C@H]1Cl)OCCO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9cab839b31194353a02ded500c33c0b4 | O=C(O)CCC/C=C\C[C@@H]1[C@@H](COc2cc(Cl)cc(Cl)c2)[C@H](O)C[C@H]1Cl.OCCN1CCOCC1>>O=C(CCC/C=C\C[C@@H]1[C@@H](COc2cc(Cl)cc(Cl)c2)[C@H](O)C[C@H]1Cl)OCCN1CCOCC1 | C(C)N(CC)CC.ClC(=O)OCC.Cl[C@@H]1C[C@H]([C@@H]([C@H]1C\C=C/CCCC(=O)O)COC1=CC(=CC(=C1)Cl)Cl)O.C(C)N(CC)CC.OCCN1CCOCC1>>N1(CCOCC1)CCOC(CCC\C=C/C[C@@H]1[C@H]([C@@H](C[C@H]1Cl)O)COC1=CC(=CC(=C1)Cl)Cl)=O | O[C:2](=[O:1])[CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8][C@@H:9]1[C@@H:10]([CH2:11][O:12][c:13]2[cH:14][c:15]([Cl:16])[cH:17][c:18]([Cl:19])[cH:20]2)[C@H:21]([OH:22])[CH2:23][C@H:24]1[Cl:25].[OH:26][CH2:27][CH2:28][N:29]1[CH2:30][CH2:31][O:32][CH2:33][CH2:34]1>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8][C... | O=C(O)CCC/C=C\C[C@@H]1[C@@H](COc2cc(Cl)cc(Cl)c2)[C@H](O)C[C@H]1Cl.OCCN1CCOCC1 | O=C(CCC/C=C\C[C@@H]1[C@@H](COc2cc(Cl)cc(Cl)c2)[C@H](O)C[C@H]1Cl)OCCN1CCOCC1 | null | null | C(Cl)Cl | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | O=C(CCC/C=C\C[C@H]1CCC[C@@H]1COc1ccccc1)OCCN1CCOCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4] | 20.3 | [{"value": 20.0, "product": "N1(CCOCC1)CCOC(CCC\\C=C/C[C@@H]1[C@H]([C@@H](C[C@H]1Cl)O)COC1=CC(=CC(=C1)Cl)Cl)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 20.3, "product": "N1(CCOCC1)CCOC(CCC\\C=C/C[C@@H]1[C@H]([C@@H](C[C@H]1Cl)O)COC1=CC(=CC(=C1)Cl)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desir... | null | null | 2.5 | HOUR | Triethylamine (6.5 μL, 0.047 mmol) and ethyl chloroformate (7 μL, 0.073 mmol) were added sequentially to a solution of (Z)-7-[(1R,2S,3R,5R)-5-chloro-2-(3,5-dichloro-phenoxymethyl)-3-hydroxy-cyclopentyl]-hept-5-enoic acid (see U.S. 60/644,069, 20 mg, 0.047 mmol) in CH2Cl2 (0.47 mL) at room temperature. After 2.5 h, trie... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1.C1CCCC1.C1COCC[NH]1 | HO- | C(Cl)Cl | null | 2.5 | O=C(O)CCC/C=C\C[C@@H]1[C@@H](COc2cc(Cl)cc(Cl)c2)[C@H](O)C[C@H]1Cl.OCCN1CCOCC1>C(Cl)Cl>O=C(CCC/C=C\C[C@@H]1[C@@H](COc2cc(Cl)cc(Cl)c2)[C@H](O)C[C@H]1Cl)OCCN1CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-416ea1cf0f1a47d29ae88e86e018323e | COC(=O)c1ccc(CN2CCN(C)CC2)cc1.Cc1ccc(N)cc1[N+](=O)[O-]>>Cc1ccc(NC(=O)c2ccc(CN3CCN(C)CC3)cc2)cc1[N+](=O)[O-] | CC=1C=CC(=CC1NC=2N=CC=C(N2)C=3C=CC=NC3)NC(=O)C=4C=CC(=CC4)CN5CCN(CC5)C.COC(C1=CC=C(C=C1)CN1CCN(CC1)C)=O.[N+](=O)([O-])C=1C=C(N)C=CC1C>>CC1=C(C=C(C=C1)NC(C1=CC=C(C=C1)CN1CCN(CC1)C)=O)[N+](=O)[O-] | CO[C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([CH2:13][N:14]2[CH2:15][CH2:16][N:17]([CH3:18])[CH2:19][CH2:20]2)[cH:21][cH:22]1.[CH3:1][c:2]1[cH:3][cH:4][c:5]([NH2:6])[cH:23][c:24]1[N+:25](=[O:26])[O-:27]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([NH:6][C:7](=[O:8])[c:9]2[cH:10][cH:11][c:12]([CH2:13][N:14]3[CH2:15][CH2:16][N:17]([CH3... | COC(=O)c1ccc(CN2CCN(C)CC2)cc1.Cc1ccc(N)cc1[N+](=O)[O-] | Cc1ccc(NC(=O)c2ccc(CN3CCN(C)CC3)cc2)cc1[N+](=O)[O-] | null | null | null | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | O=C(Nc1ccccc1)c1ccc(CN2CCNCC2)cc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | U.S. Pat. No. 5,521,184 and application WO 03/066613 describe several synthetic routes for preparing Imatinib. One synthetic process, described in Scheme 1, comprises reacting 4-(4-methyl-piperazin-1-ylmethyl)-benzoic acid methyl ester with 3-nitro-4-methyl-aniline to obtain N-(4-methyl-3-nitrophenyl)-4-(4-methyl-piper... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.C1C[NH]CC[NH]1 | HO- | null | null | null | COC(=O)c1ccc(CN2CCN(C)CC2)cc1.Cc1ccc(N)cc1[N+](=O)[O-]>>Cc1ccc(NC(=O)c2ccc(CN3CCN(C)CC3)cc2)cc1[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e436ac9eddd74505a2e8805f5065c111 | COC(=O)c1ccc(CN2CCN(C)CC2)cc1.Cc1ccc(N)cc1Br>>Cc1ccc(NC(=O)c2ccc(CN3CCN(C)CC3)cc2)cc1Br | BrC=1C=C(N)C=CC1C.COC(C1=CC=C(C=C1)CN1CCN(CC1)C)=O>>BrC=1C=C(C=CC1C)NC(C1=CC=C(C=C1)CN1CCN(CC1)C)=O | CO[C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([CH2:13][N:14]2[CH2:15][CH2:16][N:17]([CH3:18])[CH2:19][CH2:20]2)[cH:21][cH:22]1.[CH3:1][c:2]1[cH:3][cH:4][c:5]([NH2:6])[cH:23][c:24]1[Br:25]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([NH:6][C:7](=[O:8])[c:9]2[cH:10][cH:11][c:12]([CH2:13][N:14]3[CH2:15][CH2:16][N:17]([CH3:18])[CH2:19][CH... | COC(=O)c1ccc(CN2CCN(C)CC2)cc1.Cc1ccc(N)cc1Br | Cc1ccc(NC(=O)c2ccc(CN3CCN(C)CC3)cc2)cc1Br | null | null | null | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | O=C(Nc1ccccc1)c1ccc(CN2CCNCC2)cc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | Yet another process, described in Scheme 3, comprises reacting 3-bromo-4-methyl-aniline with 4-(4-methyl-piperazin-1-ylmethyl)-benzoic acid methyl ester to obtain N-(3-bromo-4-methyl-phenyl)-4-(4-methyl-piperazin-1-ylmethyl)-benzamide. The latter is reacted with 4-(3-pyridyl)-2-pyrimidine amine (which is obtained by re... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.C1C[NH]CC[NH]1 | HO- | null | null | null | COC(=O)c1ccc(CN2CCN(C)CC2)cc1.Cc1ccc(N)cc1Br>>Cc1ccc(NC(=O)c2ccc(CN3CCN(C)CC3)cc2)cc1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8725b9be91ba463d97f26d5b8682a8f5 | Cc1ccc([N+](=O)[O-])cc1N.Clc1nccc(-c2cccnc2)n1>>Cc1ccc([N+](=O)[O-])cc1Nc1nccc(-c2cccnc2)n1 | ClC1=NC=CC(=N1)C=1C=NC=CC1.NC1=C(C=CC(=C1)[N+](=O)[O-])C>>CC1=C(C=C(C=C1)[N+](=O)[O-])NC1=NC=CC(=N1)C=1C=NC=CC1 | [CH3:1][c:2]1[cH:3][cH:4][c:5]([N+:6](=[O:7])[O-:8])[cH:9][c:10]1[NH2:11].Cl[c:12]1[n:13][cH:14][cH:15][c:16](-[c:17]2[cH:18][cH:19][cH:20][n:21][cH:22]2)[n:23]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([N+:6](=[O:7])[O-:8])[cH:9][c:10]1[NH:11][c:12]1[n:13][cH:14][cH:15][c:16](-[c:17]2[cH:18][cH:19][cH:20][n:21][cH:22]2)[n:23]1 | Cc1ccc([N+](=O)[O-])cc1N.Clc1nccc(-c2cccnc2)n1 | Cc1ccc([N+](=O)[O-])cc1Nc1nccc(-c2cccnc2)n1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(-c3cccnc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | Thus, Imatinib is obtained by a synthetic route comprising reacting 2-chloro-4-(3-pyridyl)-pyrimidine with 2-amino-4-nitro-toluene to obtain N-(2-methyl-5-nitrophenyl)-4-(3-pyridyl)-2-pyrimidine-amine, which is subsequently reduced and reacted with 4-(4-methyl-piperazine-1-ylmethyl)-benzoyl chloride to yield the final ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccncc1 | HCl | null | null | null | Cc1ccc([N+](=O)[O-])cc1N.Clc1nccc(-c2cccnc2)n1>>Cc1ccc([N+](=O)[O-])cc1Nc1nccc(-c2cccnc2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b227e15041494e41aa620cd9dbef7f8b | Cc1ccc([N+](=O)[O-])cc1N.Clc1nccc(-c2cccnc2)n1>>Cc1ccc([N+](=O)[O-])cc1Nc1nccc(-c2cccnc2)n1 | ClC1=NC=CC(=N1)C=1C=NC=CC1.NC1=C(C=CC(=C1)[N+](=O)[O-])C>>CC1=C(C=C(C=C1)[N+](=O)[O-])NC1=NC=CC(=N1)C=1C=NC=CC1 | [CH3:1][c:2]1[cH:3][cH:4][c:5]([N+:6](=[O:7])[O-:8])[cH:9][c:10]1[NH2:11].Cl[c:12]1[n:13][cH:14][cH:15][c:16](-[c:17]2[cH:18][cH:19][cH:20][n:21][cH:22]2)[n:23]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([N+:6](=[O:7])[O-:8])[cH:9][c:10]1[NH:11][c:12]1[n:13][cH:14][cH:15][c:16](-[c:17]2[cH:18][cH:19][cH:20][n:21][cH:22]2)[n:23]1 | Cc1ccc([N+](=O)[O-])cc1N.Clc1nccc(-c2cccnc2)n1 | Cc1ccc([N+](=O)[O-])cc1Nc1nccc(-c2cccnc2)n1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(-c3cccnc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | Thus, Imatinib or an addition salt thereof is obtained by a synthetic route comprising reacting 2-chloro-4-(3-pyridyl)-pyrimidine with 2-amino-4-nitro-toluene to obtain N-(2-methyl-5-nitrophenyl)-4-(3-pyridyl)-2-pyrimidine-amine, which is subsequently reduced and reacted with 4-(4-methyl-piperazine-1-ylmethyl)-benzoyl ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccncc1 | HCl | null | null | null | Cc1ccc([N+](=O)[O-])cc1N.Clc1nccc(-c2cccnc2)n1>>Cc1ccc([N+](=O)[O-])cc1Nc1nccc(-c2cccnc2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-87bb5e01cf2e42c38248e11b31a483e7 | Cc1ccc([N+](=O)[O-])cc1N.Clc1nccc(-c2cccnc2)n1>>Cc1ccc([N+](=O)[O-])cc1Nc1nccc(-c2cccnc2)n1 | ClC1=NC=CC(=N1)C=1C=NC=CC1.NC1=C(C=CC(=C1)[N+](=O)[O-])C.[OH-].[Na+]>>CC1=C(C=C(C=C1)[N+](=O)[O-])NC1=NC=CC(=N1)C=1C=NC=CC1 | [CH3:1][c:2]1[cH:3][cH:4][c:5]([N+:6](=[O:7])[O-:8])[cH:9][c:10]1[NH2:11].Cl[c:12]1[n:13][cH:14][cH:15][c:16](-[c:17]2[cH:18][cH:19][cH:20][n:21][cH:22]2)[n:23]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([N+:6](=[O:7])[O-:8])[cH:9][c:10]1[NH:11][c:12]1[n:13][cH:14][cH:15][c:16](-[c:17]2[cH:18][cH:19][cH:20][n:21][cH:22]2)[n:23]1 | Cc1ccc([N+](=O)[O-])cc1N.Clc1nccc(-c2cccnc2)n1 | Cc1ccc([N+](=O)[O-])cc1Nc1nccc(-c2cccnc2)n1 | null | Cl | C(CCC)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(-c3cccnc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | A 250 ml reactor, equipped with a mechanical stirrer and a reflux condenser, was charged with 2-chloro-4-(3-pyridyl)-pyrimidine (0.5 g, 2.6 mmol), 2-amino-4-nitrotoluene (0.5 g, 3.2 mmol), n-butanol (15 ml) and concentrated HCl (5 drops) and the mixture was refluxed for 38 hours. Then, the mixture was cooled, and 6 N N... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccncc1 | HCl | Cl.C(CCC)O | null | null | Cc1ccc([N+](=O)[O-])cc1N.Clc1nccc(-c2cccnc2)n1>Cl.C(CCC)O>Cc1ccc([N+](=O)[O-])cc1Nc1nccc(-c2cccnc2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ff18a2aec00d4640b92b602960780621 | OC(CN1CCCC1)c1ccccc1>>O[C@@H](CN1CCCC1)c1ccccc1 | C(C1=CC=CC=C1)(=O)OC([C@H](O)[C@@H](O)C(=O)OC(C1=CC=CC=C1)=O)=O.C1(=CC=CC=C1)C(CN1CCCC1)O>>C1(=CC=CC=C1)[C@H](CN1CCCC1)O | [OH:1][CH:2]([CH2:3][N:4]1[CH2:5][CH2:6][CH2:7][CH2:8]1)[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[OH:1][C@@H:2]([CH2:3][N:4]1[CH2:5][CH2:6][CH2:7][CH2:8]1)[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1 | OC(CN1CCCC1)c1ccccc1 | O[C@@H](CN1CCCC1)c1ccccc1 | null | null | CO.[OH-].[Na+] | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc(CCN2CCCC2)cc1 | null | null | [] | null | null | 2 | DAY | Solutions of 35.8 g of di-O-benzoyl-L-tartaric acid in 150 ml methanol and 19.1 g of 1-phenyl-2-(1-pyrrolidinyl)-ethanol in 100 ml of methanol were mixed and the mixture left standing in a refrigerator for 2 days. The crystalline product was filtered off, washed with a small amount of cold methanol and diethyl ether an... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1CC[NH]C1.c1ccccc1 | null | CO.[OH-].[Na+] | null | 48 | OC(CN1CCCC1)c1ccccc1>CO.[OH-].[Na+]>O[C@@H](CN1CCCC1)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-86cc9ea167154d3690d3c13678780072 | O=C(Cl)C(Cl)c1ccccc1Cl.O[C@@H](CN1CCCC1)c1ccccc1>>O=C(O[C@@H](CN1CCCC1)c1ccccc1)C(Cl)c1ccccc1Cl | C1(=CC=CC=C1)[C@H](CN1CCCC1)O.ClC1=C(C=CC=C1)C(C(=O)Cl)Cl>>N1(CCCC1)C[C@@H](C1=CC=CC=C1)OC(C(Cl)C1=C(C=CC=C1)Cl)=O | Cl[C:2](=[O:1])[CH:17]([Cl:18])[c:19]1[cH:20][cH:21][cH:22][cH:23][c:24]1[Cl:25].[OH:3][C@@H:4]([CH2:5][N:6]1[CH2:7][CH2:8][CH2:9][CH2:10]1)[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[O:1]=[C:2]([O:3][C@@H:4]([CH2:5][N:6]1[CH2:7][CH2:8][CH2:9][CH2:10]1)[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[CH:17]([Cl:18])[c:19... | O=C(Cl)C(Cl)c1ccccc1Cl.O[C@@H](CN1CCCC1)c1ccccc1 | O=C(O[C@@H](CN1CCCC1)c1ccccc1)C(Cl)c1ccccc1Cl | null | CN(C)C1=CC=NC=C1 | O1CCCC1 | Acylation | Schotten-Baumann to ester | 27b76e29491fa7db5375755e15223de884a194f57a493147db0b5495ea981908 | d47ab90ace9b5dcd818151c10aae400dcf599f5a3476072b8dfedc474e97c335 | O=C(Cc1ccccc1)O[C@@H](CN1CCCC1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[Cl;D1;H0:4])-[c:5].[C:6]-[C:7](-[OH;D1;+0:8])-[c:9]>>[C:6]-[C:7](-[c:9])-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[Cl;D1;H0:4])-[c:5] | null | [] | null | null | null | null | A solution of 5.7 g of (R)-1-phenyl-2-(1-pyrrolidinyl)-ethanol in 25 ml of tetrahydrofurane was added to a solution of 6.5 g of 2,α-dichlorophenyl acetyl chloride in 25 ml of tetrahydrofurane containing 0.9 g of 4-dimethylamine pyridine. According to a similar procedure as in example 3, a mixture of diastereomeric este... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary alcohol | Ester | null | null | C1CC[NH]C1.c1ccccc1.c1ccccc1 | HCl | CN(C)C1=CC=NC=C1.O1CCCC1 | null | null | O=C(Cl)C(Cl)c1ccccc1Cl.O[C@@H](CN1CCCC1)c1ccccc1>CN(C)C1=CC=NC=C1.O1CCCC1>O=C(O[C@@H](CN1CCCC1)c1ccccc1)C(Cl)c1ccccc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-735eeb16aa944771b06909321c4eb700 | CN(C)CC(O)c1ccccc1>>CN(C)C[C@H](O)c1ccccc1 | CN(CC(O)C1=CC=CC=C1)C.C1(=CC=CC=C1)[C@H](CN1CCCC1)O.NO>>CN(C[C@H](O)C1=CC=CC=C1)C | [CH3:1][N:2]([CH3:3])[CH2:4][CH:5]([OH:6])[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[CH3:1][N:2]([CH3:3])[CH2:4][C@H:5]([OH:6])[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1 | CN(C)CC(O)c1ccccc1 | CN(C)C[C@H](O)c1ccccc1 | null | null | CO | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccccc1 | null | null | [] | null | null | null | null | Racemic 2-dimethylamino-1-phenyl ethanol was cleaved in accordance with the 2-pyrrolidinyl-1-phenyl ethanol (see example 6) using 16.5 g of crude amino alcohol as described in example 8. The yield of oily (R)-2-dimethyl-amino-1-phenyl ethanol with a [αD20] value of −45.5° (methanol) was 8.9 g.
Conditions: See reaction.... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1 | null | CO | null | null | CN(C)CC(O)c1ccccc1>CO>CN(C)C[C@H](O)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ebf0d7669a01422dbfdb9f26b0eb75bf | COc1ccnc(C[S+]([O-])c2nc3cc(OC(F)F)ccc3[n-]2)c1OC>>COc1ccnc(C[S+]([O-])c2nc3cc(OC(F)F)ccc3[nH]2)c1OC.[OH-] | COC=1C=CN=C(C1OC)C[S+](C=2[N-]C=3C=CC(=CC3N2)OC(F)F)[O-].[Na+]>>COC=1C=CN=C(C1OC)C[S+](C=2NC=3C=CC(=CC3N2)OC(F)F)[O-].[OH-].[Na+] | [CH3:1][O:2][c:3]1[cH:4][cH:5][n:6][c:7]([CH2:8][S+:9]([O-:10])[c:11]2[n:12][c:13]3[cH:14][c:15]([O:16][CH:17]([F:18])[F:19])[cH:20][cH:21][c:22]3[n-:23]2)[c:24]1[O:25][CH3:26]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][n:6][c:7]([CH2:8][S+:9]([O-:10])[c:11]2[n:12][c:13]3[cH:14][c:15]([O:16][CH:17]([F:18])[F:19])[cH:20][cH:21][c:... | COc1ccnc(C[S+]([O-])c2nc3cc(OC(F)F)ccc3[n-]2)c1OC | COc1ccnc(C[S+]([O-])c2nc3cc(OC(F)F)ccc3[nH]2)c1OC.[OH-] | null | null | CC(=O)C | Functional Group Interconversion | OtherReaction | 0d6fc6eb01acfd45833b397c8f5a76a7184fae8843ce3428d595feb9c6adf18e | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | c1ccc(C[SH+]c2nc3ccccc3[nH]2)nc1 | [#16;+:1]-[c:2]1:[#7;a:3]:[c:4](:[c:5]):[c:6](:[c:7]):[n-;H0;D2:8]:1>>[#16;+:1]-[c:2]1:[#7;a:3]:[c:4](:[c:5]):[c:6](:[c:7]):[nH;D2;+0:8]:1 | null | [] | null | null | null | null | Pantoprazole sodium Form II can be prepared by forming a solution of pantoprazole and excess sodium hydroxide in acetone and crystallizing Form II from the solution. Preferably, pantoprazole is added as the free base, though the sodium salt may be used. Excess sodium hydroxide is conveniently added as a concentrated aq... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2[n-]cnc2c1 | c1ccc2[nH]cnc2c1 | c1ccncc1.c1ccc2[nH]cnc2c1 | null | CC(=O)C | null | null | COc1ccnc(C[S+]([O-])c2nc3cc(OC(F)F)ccc3[n-]2)c1OC>CC(=O)C>COc1ccnc(C[S+]([O-])c2nc3cc(OC(F)F)ccc3[nH]2)c1OC.[OH-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-acbab0da268a4f189510e34f7728fec5 | COc1ccnc(C[S+]([O-])c2nc3cc(OC(F)F)ccc3[nH]2)c1OC>>COc1ccnc(C[S+]([O-])c2nc3cc(OC(F)F)ccc3[n-]2)c1OC | [OH-].[Na+].[OH-].[Na+].COC=1C=CN=C(C1OC)C[S+](C=2NC=3C=CC(=CC3N2)OC(F)F)[O-].COC=1C=CN=C(C1OC)C[S+](C=2NC=3C=CC(=CC3N2)OC(F)F)[O-]>>COC=1C=CN=C(C1OC)C[S+](C=2[N-]C=3C=CC(=CC3N2)OC(F)F)[O-].[Na+] | [CH3:1][O:2][c:3]1[cH:4][cH:5][n:6][c:7]([CH2:8][S+:9]([O-:10])[c:11]2[n:12][c:13]3[cH:14][c:15]([O:16][CH:17]([F:18])[F:19])[cH:20][cH:21][c:22]3[nH:23]2)[c:24]1[O:25][CH3:26]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][n:6][c:7]([CH2:8][S+:9]([O-:10])[c:11]2[n:12][c:13]3[cH:14][c:15]([O:16][CH:17]([F:18])[F:19])[cH:20][cH:21][c:... | COc1ccnc(C[S+]([O-])c2nc3cc(OC(F)F)ccc3[nH]2)c1OC | COc1ccnc(C[S+]([O-])c2nc3cc(OC(F)F)ccc3[n-]2)c1OC | null | null | CC(=O)C | Reduction | OtherReaction | 73e3c5abcbae739c230bd8787a8ba86237c4832ac4b8d9821b3e0022b929d7b0 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1ccc(C[SH+]c2nc3ccccc3[n-]2)nc1 | [#16;+:1]-[c:2]1:[#7;a:3]:[c:4](:[c:5]):[c:6](:[c:7]):[nH;D2;+0:8]:1>>[#16;+:1]-[c:2]1:[#7;a:3]:[c:4](:[c:5]):[c:6](:[c:7]):[n-;H0;D2:8]:1 | 65 | [{"value": 65.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 2 | CELSIUS | 2 | HOUR | A 100 ml round bottomed flask equipped with a magnetic stir bar was charged with acetone (50 ml). Pantoprazole (10 g, 25.7 mmol) was then added to the flask. After the pantoprazole had completely dissolved, the solution was cooled to about 2° C. Forty seven percent sodium hydroxide (aq.) equivalent to 2.4 grams of soli... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2[nH]cnc2c1 | c1ccc2[n-]cnc2c1 | c1ccncc1.c1ccc2[n-]cnc2c1 | null | CC(=O)C | 2 | 2 | COc1ccnc(C[S+]([O-])c2nc3cc(OC(F)F)ccc3[nH]2)c1OC>CC(=O)C>COc1ccnc(C[S+]([O-])c2nc3cc(OC(F)F)ccc3[n-]2)c1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-accc83431eda449d8f9bf1d3f65d93f7 | COc1ccnc(C[S+]([O-])c2nc3cc(OC(F)F)ccc3[nH]2)c1OC>>COc1ccnc(C[S+]([O-])c2nc3cc(OC(F)F)ccc3[n-]2)c1OC | COC=1C=CN=C(C1OC)C[S+](C=2NC=3C=CC(=CC3N2)OC(F)F)[O-].[OH-].[Na+]>>COC=1C=CN=C(C1OC)C[S+](C=2[N-]C=3C=CC(=CC3N2)OC(F)F)[O-].[Na+] | [CH3:1][O:2][c:3]1[cH:4][cH:5][n:6][c:7]([CH2:8][S+:9]([O-:10])[c:11]2[n:12][c:13]3[cH:14][c:15]([O:16][CH:17]([F:18])[F:19])[cH:20][cH:21][c:22]3[nH:23]2)[c:24]1[O:25][CH3:26]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][n:6][c:7]([CH2:8][S+:9]([O-:10])[c:11]2[n:12][c:13]3[cH:14][c:15]([O:16][CH:17]([F:18])[F:19])[cH:20][cH:21][c:... | COc1ccnc(C[S+]([O-])c2nc3cc(OC(F)F)ccc3[nH]2)c1OC | COc1ccnc(C[S+]([O-])c2nc3cc(OC(F)F)ccc3[n-]2)c1OC | null | null | C1(=CC=CC=C1)C | Reduction | OtherReaction | 73e3c5abcbae739c230bd8787a8ba86237c4832ac4b8d9821b3e0022b929d7b0 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1ccc(C[SH+]c2nc3ccccc3[n-]2)nc1 | [#16;+:1]-[c:2]1:[#7;a:3]:[c:4](:[c:5]):[c:6](:[c:7]):[nH;D2;+0:8]:1>>[#16;+:1]-[c:2]1:[#7;a:3]:[c:4](:[c:5]):[c:6](:[c:7]):[n-;H0;D2:8]:1 | null | [] | null | null | null | null | A 100 ml flask was charged with toluene (50.0 ml). Pantoprazole (5.0 g, 12.8 mmol) and 47% aqueous NaOH (1.2 g) were added to the stirred solvent at room temperature. The mixture was stirred until dissolution and then overnight until precipitation. The solid was filtered giving pantoprazole sodium. The sample was dried... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2[nH]cnc2c1 | c1ccc2[n-]cnc2c1 | c1ccncc1.c1ccc2[n-]cnc2c1 | null | C1(=CC=CC=C1)C | null | null | COc1ccnc(C[S+]([O-])c2nc3cc(OC(F)F)ccc3[nH]2)c1OC>C1(=CC=CC=C1)C>COc1ccnc(C[S+]([O-])c2nc3cc(OC(F)F)ccc3[n-]2)c1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ee860321d9234dfc9df03d96e37fd037 | COc1ccnc(C[S+]([O-])c2nc3cc(OC(F)F)ccc3[nH]2)c1OC>>COc1ccnc(C[S+]([O-])c2nc3cc(OC(F)F)ccc3[n-]2)c1OC | COC=1C=CN=C(C1OC)C[S+](C=2NC=3C=CC(=CC3N2)OC(F)F)[O-].[OH-].[Na+]>>COC=1C=CN=C(C1OC)C[S+](C=2[N-]C=3C=CC(=CC3N2)OC(F)F)[O-].[Na+] | [CH3:1][O:2][c:3]1[cH:4][cH:5][n:6][c:7]([CH2:8][S+:9]([O-:10])[c:11]2[n:12][c:13]3[cH:14][c:15]([O:16][CH:17]([F:18])[F:19])[cH:20][cH:21][c:22]3[nH:23]2)[c:24]1[O:25][CH3:26]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][n:6][c:7]([CH2:8][S+:9]([O-:10])[c:11]2[n:12][c:13]3[cH:14][c:15]([O:16][CH:17]([F:18])[F:19])[cH:20][cH:21][c:... | COc1ccnc(C[S+]([O-])c2nc3cc(OC(F)F)ccc3[nH]2)c1OC | COc1ccnc(C[S+]([O-])c2nc3cc(OC(F)F)ccc3[n-]2)c1OC | null | null | C(CCC)O | Reduction | OtherReaction | 73e3c5abcbae739c230bd8787a8ba86237c4832ac4b8d9821b3e0022b929d7b0 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1ccc(C[SH+]c2nc3ccccc3[n-]2)nc1 | [#16;+:1]-[c:2]1:[#7;a:3]:[c:4](:[c:5]):[c:6](:[c:7]):[nH;D2;+0:8]:1>>[#16;+:1]-[c:2]1:[#7;a:3]:[c:4](:[c:5]):[c:6](:[c:7]):[n-;H0;D2:8]:1 | null | [] | null | null | 8 | HOUR | Pantoprazole (5.0 g, 12.8 mmol) and 98.5% NaOH (0.52 g, 12.8 mmol) were dissolved in 1-butanol (10.0 ml) at room temperature and the solution was stirred overnight at room temperature. The solution was cooled in a refrigerator and then stirred at room temperature until crystallization occurred. The crystals were filter... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2[nH]cnc2c1 | c1ccc2[n-]cnc2c1 | c1ccncc1.c1ccc2[n-]cnc2c1 | null | C(CCC)O | null | 8 | COc1ccnc(C[S+]([O-])c2nc3cc(OC(F)F)ccc3[nH]2)c1OC>C(CCC)O>COc1ccnc(C[S+]([O-])c2nc3cc(OC(F)F)ccc3[n-]2)c1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0a84cd2ef25e4324b93bae980fdd2e4a | COc1ccc(C#N)cc1.[Cl][Mg][c]1ccccc1>>COc1ccc(-c2ccccc2)cc1 | COC1=CC=C(C#N)C=C1.CCCCCCCCCCCCC.C1(=CC=CC=C1)[Mg]Cl.[Cl-].C1(=CC=CC=C1)[Zn+]>>C1(=CC=CC=C1)C1=CC=C(C=C1)OC | N#C[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:14][cH:13]1.[Cl][Mg][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[cH:13][cH:14]1 | COc1ccc(C#N)cc1.[Cl][Mg][c]1ccccc1 | COc1ccc(-c2ccccc2)cc1 | null | [Cl-].[Zn+2].[Cl-] | C1CCOC1 | C-C Coupling | OtherReaction | 56fd8131e2b4058a94fc10996ce554527798dacc8dc497c879f344f9b79d88bf | b7d29fa9e0a7d9ae2f2a2797da751d9d03a466b58f528baa09db504746325a44 | c1ccc(-c2ccccc2)cc1 | N#C-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[Cl]-[Mg]-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9]:[c:10] | 45 | [{"value": 45.0, "product": "C1(=CC=CC=C1)C1=CC=C(C=C1)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A solution of zinc chloride (0.48 g; 3.5 mmol) in THF (5 mL) was treated at 0° C. with phenylmagnesium chloride (2.1 mL of a 1.40 M solution in THF; 3.0 mmol) and then stirred at room temperature for 30 min. The mixture of phenylzinc chloride thus obtained was then treated with a solution of 4-methoxybenzonitrile (0.27... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Nitrile | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | Mg | [Cl-].[Zn+2].[Cl-].C1CCOC1 | null | 0.5 | COc1ccc(C#N)cc1.[Cl][Mg][c]1ccccc1>[Cl-].[Zn+2].[Cl-].C1CCOC1>COc1ccc(-c2ccccc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e718b5c472454dc0b21020ceafb9ad37 | COc1ccc(C(=N)c2ccccc2)cc1>>COc1ccc(-c2ccccc2)cc1 | CP(C)C.COC1=CC=C(C(C2=CC=CC=C2)=N)C=C1>>C1(=CC=CC=C1)C1=CC=C(C=C1)OC | N=C([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:14][cH:13]1)[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[cH:13][cH:14]1 | COc1ccc(C(=N)c2ccccc2)cc1 | COc1ccc(-c2ccccc2)cc1 | null | C/C(=C/C(=O)C)/[O-].C/C(=C/C(=O)C)/[O-].[Ni+2].[Ni] | null | Miscellaneous | OtherReaction | 999b65ddf01d6c95f0b4375b9a2a5471c9ffe6453f7cf55d73aa81009d3ea1a1 | f84f44e4c005115224407dbb994558777a16078301b35734330b6ae282e29f41 | c1ccc(-c2ccccc2)cc1 | N=C(-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9]:[c:10] | 1,600 | [{"value": 88.0, "product": "C1(=CC=CC=C1)C1=CC=C(C=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 1600.0, "product": "C1(=CC=CC=C1)C1=CC=C(C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | The procedure was identical to Example 1, with the exception that the nickel catalyst used was derived in situ from a combination of anhydrous nickel acetylacetonate (0.026 g; 5 mol %) and trimethylphosphine (0.20 mL of 1 M solution in toluene; 10 mol %). GC analysis of the organic phase of the hydrolyzed reaction samp... | 10.6084/m9.figshare.5104873.v1 | null | Unsubstituted imine | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | Other | C/C(=C/C(=O)C)/[O-].C/C(=C/C(=O)C)/[O-].[Ni+2].[Ni] | null | 2 | COc1ccc(C(=N)c2ccccc2)cc1>C/C(=C/C(=O)C)/[O-].C/C(=C/C(=O)C)/[O-].[Ni+2].[Ni]>COc1ccc(-c2ccccc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f1e894c4dd8b47c4ba10a08c0c0a36ee | COc1ccc(C#N)cc1.[Li][c]1ccccc1>>COc1ccc(-c2ccccc2)cc1 | [Br-].[Mg+2].[Br-].C1(=CC=CC=C1)[Li].COC1=CC=C(C(C2=CC=CC=C2)=N)C=C1.COC1=CC=C(C#N)C=C1.CCCCCCCCCCCCC.CC(C)([O-])C.[Li+]>>C1(=CC=CC=C1)C1=CC=C(C=C1)OC | N#C[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:14][cH:13]1.[Li][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[cH:13][cH:14]1 | COc1ccc(C#N)cc1.[Li][c]1ccccc1 | COc1ccc(-c2ccccc2)cc1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | a2248e0771f91e7acef322ad94f7832605ad21867c930450f56e5d8ce491f5d1 | 4318d1235968fbd93d528a51f6640671795eb99dc2e7ea1a67f893a1c90dbeea | c1ccc(-c2ccccc2)cc1 | N#C-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[Li]-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9]:[c:10] | 927.8 | [{"value": 84.0, "product": "C1(=CC=CC=C1)C1=CC=C(C=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 927.8, "product": "C1(=CC=CC=C1)C1=CC=C(C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 1 | HOUR | A slurry of magnesium bromide (0.74 g; 4.0 mmol) in THF (3 mL) was treated at room temperature with phenyllithium (2.4 mL of 1.7 M solution; 4.0 mmol). The solution was heated at 60° C. for 30 min, and was then treated at 60° with lithium t-butoxide (4.4 mL of 1.0 M solution in THF; 4.4 mmol) and heating was continued ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Aryl lithium | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | Li | C1CCOC1 | 60 | 1 | COc1ccc(C#N)cc1.[Li][c]1ccccc1>C1CCOC1>COc1ccc(-c2ccccc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fa11e0ea87004180a859d61e27aca6b0 | N#Cc1ccncc1.[Cl][Mg][c]1ccccc1>>c1ccc(-c2ccncc2)cc1 | C1(=CC=CC=C1)[Mg]Cl.C1(=CC=CC=C1)S[Li].C(CC(O)(C(=O)[O-])CC(=O)[O-])(=O)[O-].[Na+].[Na+].[Na+].C1(=CC=CC=C1)[Mg]Cl.[S-]C1=CC=CC=C1.[Li+].C(#N)C1=CC=NC=C1>>C1(=CC=CC=C1)C1=CC=NC=C1 | N#C[c:5]1[cH:6][cH:7][n:8][cH:9][cH:10]1.[Cl][Mg][c:4]1[cH:3][cH:2][cH:1][cH:12][cH:11]1>>[cH:1]1[cH:2][cH:3][c:4](-[c:5]2[cH:6][cH:7][n:8][cH:9][cH:10]2)[cH:11][cH:12]1 | N#Cc1ccncc1.[Cl][Mg][c]1ccccc1 | c1ccc(-c2ccncc2)cc1 | null | CP(C)C.C/C(=C/C(=O)C)/[O-].C/C(=C/C(=O)C)/[O-].[Ni+2] | C1CCOC1 | C-C Coupling | OtherReaction | c8abdf91a8398fd6e178d6f3f9e9bc7bc7bbe51804c0a725a9a427d4c11ded30 | b7d29fa9e0a7d9ae2f2a2797da751d9d03a466b58f528baa09db504746325a44 | c1ccc(-c2ccncc2)cc1 | N#C-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1.[Cl]-[Mg]-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]>>[c:9]:[c:8]:[c;H0;D3;+0:7](-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1):[c:10]:[c:11] | 94.5 | [{"value": 91.0, "product": "C1(=CC=CC=C1)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.5, "product": "C1(=CC=CC=C1)C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 10 | MINUTE | In a 1 L 3-neck flask, equipped with a mechanical stirrer, were mixed phenyl magnesium chloride (96.1 mL; 192 mmol; 2.00 M in THF) and lithium thiophenoxide (211 mL; 211 mmol; 1.00 M THF) under a blanket of nitrogen. This mixture was heated to 60° C. for 1 h, and then cooled to 0-5° C. with an ice bath. In a separate 1... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Nitrile | null | c1ccncc1.c1ccccc1 | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | Mg | CP(C)C.C/C(=C/C(=O)C)/[O-].C/C(=C/C(=O)C)/[O-].[Ni+2].C1CCOC1 | 60 | 0.166667 | N#Cc1ccncc1.[Cl][Mg][c]1ccccc1>CP(C)C.C/C(=C/C(=O)C)/[O-].C/C(=C/C(=O)C)/[O-].[Ni+2].C1CCOC1>c1ccc(-c2ccncc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5ce591e79cf64ac3bfff0cc32f5b5f8a | CN(C)c1ccc(CN)cc1.NCCCC(=O)OCc1ccccc1.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>>CN(C)c1ccc(CNC(=O)NCCCC(=O)OCc2ccccc2)cc1 | Cl.Cl.CN(C1=CC=C(CN)C=C1)C.C1(=CC=C(C=C1)S(=O)(=O)O)C.C(C1=CC=CC=C1)OC(CCCN)=O.ClC(Cl)(OC(OC(Cl)(Cl)Cl)=O)Cl.C(C)N(CC)CC.C(C)N(CC)CC>>C(C1=CC=CC=C1)OC(CCCNC(=O)NCC1=CC=C(C=C1)N(C)C)=O | [CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([CH2:8][NH2:9])[cH:26][cH:27]1.[NH2:12][CH2:13][CH2:14][CH2:15][C:16](=[O:17])[O:18][CH2:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1.ClC(Cl)(Cl)O[C:10](OC(Cl)(Cl)Cl)=[O:11]>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([CH2:8][NH:9][C:10](=[O:11])[NH:12][CH2:13][CH2:14][C... | CN(C)c1ccc(CN)cc1.NCCCC(=O)OCc1ccccc1.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl | CN(C)c1ccc(CNC(=O)NCCCC(=O)OCc2ccccc2)cc1 | null | null | ClCCl.[Cl-].[Na+].O | Acylation | OtherReaction | 28ee7ff95d738e45269fa5b469f275a1296c4b167a5d0563a291181ae7540ff4 | 9b884e2244637471aa1727f9c16919cb29ddb345e1156c83044a8879831c507f | O=C(NCCCC(=O)OCc1ccccc1)NCc1ccccc1 | Cl-C(-Cl)(-Cl)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-C(-Cl)(-Cl)-Cl.[C:3]-[C:4]-[NH2;D1;+0:5].[NH2;D1;+0:6]-[C:7]-[c:8]>>[C:3]-[C:4]-[NH;D2;+0:5]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[C:7]-[c:8] | 278.4 | [{"value": 93.0, "product": "C(C1=CC=CC=C1)OC(CCCNC(=O)NCC1=CC=C(C=C1)N(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 278.4, "product": "C(C1=CC=CC=C1)OC(CCCNC(=O)NCC1=CC=C(C=C1)N(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a vigorous stirred suspension of 4-amino-butyric acid benzyl ester toluene-4-sulfonic acid (0.730 g, 2.00 mmol) and triphosgene (0.200 g, 0.667 mmol) in dichloromethane (40 mL) at −78° C. under nitrogen atmosphere, was added triethylamine (1.0 mL, 7.188 mmol, in 10 mL dichloromethane) dropwise via an additional f un... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Trichloro group.Carbonic Ester.Primary amine.Primary amine | Urea | null | null | c1ccccc1.c1ccccc1 | HCl | ClCCl.[Cl-].[Na+].O | null | 1 | CN(C)c1ccc(CN)cc1.NCCCC(=O)OCc1ccccc1.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>ClCCl.[Cl-].[Na+].O>CN(C)c1ccc(CNC(=O)NCCCC(=O)OCc2ccccc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-00df31b315224b0db81c5d1232c5d610 | CN(C)c1ccc(CNC(=O)NCCCC(=O)NOCc2ccccc2)cc1>>CN(C)c1ccc(CNC(=O)NCCCC(=O)NO)cc1 | C(C1=CC=CC=C1)ONC(CCCNC(=O)NCC1=CC=C(C=C1)N(C)C)=O>>CN(C1=CC=C(CNC(NCCCC(=O)NO)=O)C=C1)C | c1ccc(C[O:19][NH:18][C:16]([CH2:15][CH2:14][CH2:13][NH:12][C:10]([NH:9][CH2:8][c:7]2[cH:6][cH:5][c:4]([N:2]([CH3:1])[CH3:3])[cH:21][cH:20]2)=[O:11])=[O:17])cc1>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([CH2:8][NH:9][C:10](=[O:11])[NH:12][CH2:13][CH2:14][CH2:15][C:16](=[O:17])[NH:18][OH:19])[cH:20][cH:21]1 | CN(C)c1ccc(CNC(=O)NCCCC(=O)NOCc2ccccc2)cc1 | CN(C)c1ccc(CNC(=O)NCCCC(=O)NO)cc1 | null | [Pd] | CO | Deprotection | OtherReaction | 94fa5e5ed4a5b32c4aba0dd3c8151bfdd08491d1bc6453e9fd01d7dc3e51cd0f | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | c1ccccc1 | [C:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[O;H0;D2;+0:5]-C-c1:c:c:c:c:c:1>>[C:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[OH;D1;+0:5] | 92 | [{"value": 92.0, "product": "CN(C1=CC=C(CNC(NCCCC(=O)NO)=O)C=C1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To a solution of the N-benzyloxy-4-[3-(4-dimethylamino-benzyl)-ureido]-butyramide (287 mg, 0.747 mmol) in methanol (15 mL) was added 10% palladium on carbon (30 mg) and the resulting reaction was allowed to stir under a hydrogen atmosphere for 18 hr, after which time the reaction mixture was filtered and concentrated i... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1 | null | c1ccccc1 | Other | [Pd].CO | null | 18 | CN(C)c1ccc(CNC(=O)NCCCC(=O)NOCc2ccccc2)cc1>[Pd].CO>CN(C)c1ccc(CNC(=O)NCCCC(=O)NO)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-18bf322cf855490798bee4e2e84b2ef0 | CN(C)c1ccc(CNC(=O)NCCCC(=O)NO)cc1.NCCCCCCC(=O)OCc1ccccc1>>CN(C)c1ccc(CNC(=O)NCCCCCCC(=O)O)cc1 | CN(C1=CC=C(CNC(NCCCC(=O)NO)=O)C=C1)C.C1(=CC=C(C=C1)S(=O)(=O)O)C.C(C1=CC=CC=C1)OC(CCCCCCN)=O>>CN(C1=CC=C(CNC(NCCCCCCC(=O)O)=O)C=C1)C | O=C(CCC[NH:12][C:10]([NH:9][CH2:8][c:7]1[cH:6][cH:5][c:4]([N:2]([CH3:1])[CH3:3])[cH:23][cH:22]1)=[O:11])NO.N[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19](=[O:20])[O:21]Cc1ccccc1>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([CH2:8][NH:9][C:10](=[O:11])[NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:1... | CN(C)c1ccc(CNC(=O)NCCCC(=O)NO)cc1.NCCCCCCC(=O)OCc1ccccc1 | CN(C)c1ccc(CNC(=O)NCCCCCCC(=O)O)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 84557db8ac0eb45fb3642de4953af83589cffc7690b4bd1e8855bf3ebb1bc4a3 | e842414270b5e623bfbd8162311e9e13a2410702e3adaac65a4ee3622d82a9fc | c1ccccc1 | N-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5](=[O;D1;H0:6])-[O;H0;D2;+0:7]-C-c1:c:c:c:c:c:1.O-N-C(=O)-C-C-C-[NH;D2;+0:8]-[C:9](=[O;D1;H0:10])-[#7:11]-[C:12]>>[C:4]-[C:5](=[O;D1;H0:6])-[OH;D1;+0:7].[C:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:8]-[C:9](=[O;D1;H0:10])-[#7:11]-[C:12] | null | [] | null | null | null | null | Compound 5 was prepared using the methodology described for the preparation of compound 2, by substituting 4-amino-butyric acid benzyl ester toluene-4-sulfonic acid with 7-amino-heptanoic acid benzyl ester toluene-4-sulfonic acid. 1H NMR (300 MHz, DMSO-d6) δ (ppm) 10.33 (br, s, 1H), 8.66 (br s, 1H), 7.05 (d, J=8.7 Hz, ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Urea.Secondary amide.Primary amine | Carboxylic acid.Urea | c1ccccc1 | null | c1ccccc1 | HO- | null | null | null | CN(C)c1ccc(CNC(=O)NCCCC(=O)NO)cc1.NCCCCCCC(=O)OCc1ccccc1>>CN(C)c1ccc(CNC(=O)NCCCCCCC(=O)O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2e7e9aaa12b44c748f460225f6b25d9c | CN(C)c1ccc(CN)cc1.Cc1ccc(S(=O)(=O)O)cc1.NCCCCCC(=O)OCc1ccccc1.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>>O=C(NCCCCCC(=O)OCc1ccccc1)NC12CC3CC(CC(C3)C1)C2 | Cl.Cl.CN(C1=CC=C(CN)C=C1)C.C1(=CC=C(C=C1)S(=O)(=O)O)C.C(C1=CC=CC=C1)OC(CCCCCN)=O.ClC(Cl)(OC(OC(Cl)(Cl)Cl)=O)Cl.C(C)N(CC)CC>>C(C1=CC=CC=C1)OC(CCCCCNC(=O)NC12CC3CC(CC(C1)C3)C2)=O | CN(C)[c:25]1c[cH:21][c:22]([CH2:20][NH2:19])[cH:27][cH:26]1.O=S(=O)(O)c1cc[c:24]([CH3:23])cc1.[NH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9](=[O:10])[O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1.ClC(Cl)(Cl)O[C:2](OC(Cl)(Cl)Cl)=[O:1]>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9](=[O:10])[O:11]... | CN(C)c1ccc(CN)cc1.Cc1ccc(S(=O)(=O)O)cc1.NCCCCCC(=O)OCc1ccccc1.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl | O=C(NCCCCCC(=O)OCc1ccccc1)NC12CC3CC(CC(C3)C1)C2 | null | null | ClCCl | Acylation | OtherReaction | 21ef8ba1fe1143ef552b8fde2d69ec6fde51120a86f799e368372b2b445551ea | b425761bd607612009c9c987139794a4be2c93d0d1248f685686bbb00d19b9c1 | O=C(NCCCCCC(=O)OCc1ccccc1)NC12CC3CC(CC(C3)C1)C2 | C-N(-C)-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[cH;D2;+0:3]:[c;H0;D3;+0:4](-[CH2;D2;+0:5]-[NH2;D1;+0:6]):[cH;D2;+0:7]:c:1.Cl-C(-Cl)(-Cl)-O-[C;H0;D3;+0:8](=[O;D1;H0:9])-O-C(-Cl)(-Cl)-Cl.O-S(=O)(=O)-c1:c:c:[c;H0;D3;+0:10](-[CH3;D1;+0:11]):c:c:1.[C:12]-[C:13]-[NH2;D1;+0:14]>>[C:12]-[C:13]-[NH;D2;+0:14]-[C;H0;D3;+0:8](=[O;D1;H0:9])-... | 180.9 | [{"value": 61.0, "product": "C(C1=CC=CC=C1)OC(CCCCCNC(=O)NC12CC3CC(CC(C1)C3)C2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 180.9, "product": "C(C1=CC=CC=C1)OC(CCCCCNC(=O)NC12CC3CC(CC(C1)C3)C2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a vigorously stirred suspension of 6-amino-hexanoic acid benzyl ester toluene-4-sulfonic acid (0.786 g, 2.00 mmol) and triphosgene (0.200 g, 0.667 mmol) in dichloromethane (30 mL) at −78° C. under inert atmosphere, was added triethylamine (1.0 mL, 7.188 mmol, in 10 mL dichloromethane) dropwise via additional funnel ... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Trichloro group.Trichloro group.Carbonic Ester.Primary amine.Primary amine.Tertiary amine | Urea | c1ccccc1.c1ccccc1 | C1C2CC3CC1CC(C2)C3 | c1ccccc1.C1C2CC3CC1CC(C2)C3 | TsOH.HCl | ClCCl | null | 1 | CN(C)c1ccc(CN)cc1.Cc1ccc(S(=O)(=O)O)cc1.NCCCCCC(=O)OCc1ccccc1.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>ClCCl>O=C(NCCCCCC(=O)OCc1ccccc1)NC12CC3CC(CC(C3)C1)C2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e2450ec8f4ba404aa6c8454cf88d2725 | COC(=O)CS.OC(c1ccccc1)(c1ccccc1)c1ccccc1>>COC(=O)CSC(c1ccccc1)(c1ccccc1)c1ccccc1 | SCC(=O)OC.C1(=CC=CC=C1)C(O)(C1=CC=CC=C1)C1=CC=CC=C1.FC(C(=O)O)(F)F>>COC(CSC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)=O | [CH3:1][O:2][C:3](=[O:4])[CH2:5][SH:6].O[C:7]([c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)([c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)[c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][S:6][C:7]([c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)([c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)[c:20]1[cH:2... | COC(=O)CS.OC(c1ccccc1)(c1ccccc1)c1ccccc1 | COC(=O)CSC(c1ccccc1)(c1ccccc1)c1ccccc1 | null | null | C(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 550a7964778c9f12760ef1f41256181c2082f29a84fb8f4bf2c9443b33dd6567 | 42963aad950e323e8799a3db4f42f888ff868551c22c911dbccb9f890bdeb2f6 | c1ccc(C(c2ccccc2)c2ccccc2)cc1 | O-[C;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10].[C;D1;H3:11]-[#8:12]-[C:13](=[O;D1;H0:14])-[C:15]-[SH;D1;+0:16]>>[C;D1;H3:11]-[#8:12]-[C:13](=[O;D1;H0:14])-[C:15]-[S;H0;D2;+0:16]-[C;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10] | 91.3 | [{"value": 91.0, "product": "COC(CSC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.3, "product": "COC(CSC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a mixture of methyl mercaptoacetate (5.30 g, 50 mmol) and triphenylmethanol (13.0 g, 50 mmol) in chloroform (20 mL) was added trifloroacetic acid (5 mL) in 5 min. After stirring at room temperature for 1 h, the volatiles were removed in vacuo. The crude product was purified by recrystallization (dichloromethane/Hexa... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol.Aliphatic thiol | Monosulfide | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | C(Cl)(Cl)Cl | null | 1 | COC(=O)CS.OC(c1ccccc1)(c1ccccc1)c1ccccc1>C(Cl)(Cl)Cl>COC(=O)CSC(c1ccccc1)(c1ccccc1)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-444cc2f5c962494f9efaf402bc1d7aa1 | COC(=O)CSC(c1ccccc1)(c1ccccc1)c1ccccc1.NCCCCCN>>NCCCCCC(=O)CSC(c1ccccc1)(c1ccccc1)c1ccccc1 | NCCCCCN.COC(CSC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)=O.CO>>NCCCCCC(CSC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)=O | CO[C:7](=[O:8])[CH2:9][S:10][C:11]([c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)([c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1)[c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1.N[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][NH2:1]>>[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7](=[O:8])[CH2:9][S:10][C:11]([c:12]1[cH:13][cH:14][cH:15][cH:... | COC(=O)CSC(c1ccccc1)(c1ccccc1)c1ccccc1.NCCCCCN | NCCCCCC(=O)CSC(c1ccccc1)(c1ccccc1)c1ccccc1 | null | null | ClCCl.CO.CCN(CC)CC | C-C Coupling | OtherReaction | 1a69e220b52fe9824bfcad182fc3bd64f3f705c2ea3f3199bde2a17596886895 | bed782162e5697dea9604bde8f3ba126d86aa25d57c682ebb8a09e1e7c81db45 | c1ccc(C(c2ccccc2)c2ccccc2)cc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#16:4].N-[CH2;D2;+0:5]-[C:6]-[C:7]>>[#16:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:5]-[C:6]-[C:7] | 56 | [{"value": 54.0, "product": "NCCCCCC(CSC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.0, "product": "NCCCCCC(CSC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1,5-Diaminopentane (0.75 g, 7.21 mmol) was stirred while tritylsulfanyl-acetic acid methyl ester (2.53 g, 7.27 mmol) was added slowly. The mixture was heated at 100° C. for 2 h while methyl alcohol escaped. The product was isolated by column chromatography (dichloromethane/MeOH/Et3N=10/1/0.1) to provide 7-Amino-1-trity... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Ketone | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | ClCCl.CO.CCN(CC)CC | null | null | COC(=O)CSC(c1ccccc1)(c1ccccc1)c1ccccc1.NCCCCCN>ClCCl.CO.CCN(CC)CC>NCCCCCC(=O)CSC(c1ccccc1)(c1ccccc1)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3f7f3537cb99427f80f6b33da6f8e173 | NCCCCCC(=O)CSC(c1ccccc1)(c1ccccc1)c1ccccc1.O=C=Nc1ccccc1>>O=C(CCCCCNC(=O)Nc1ccccc1)CSC(c1ccccc1)(c1ccccc1)c1ccccc1 | NCCCCCC(CSC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)=O.C1(=CC=CC=C1)N=C=O>>O=C(CCCCCNC(=O)NC1=CC=CC=C1)CSC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | [O:1]=[C:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH2:8])[CH2:18][S:19][C:20]([c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1)([c:27]1[cH:28][cH:29][cH:30][cH:31][cH:32]1)[c:33]1[cH:34][cH:35][cH:36][cH:37][cH:38]1.[C:9](=[O:10])=[N:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:... | NCCCCCC(=O)CSC(c1ccccc1)(c1ccccc1)c1ccccc1.O=C=Nc1ccccc1 | O=C(CCCCCNC(=O)Nc1ccccc1)CSC(c1ccccc1)(c1ccccc1)c1ccccc1 | null | null | ClCCl | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(CCCCCNC(=O)Nc1ccccc1)CSC(c1ccccc1)(c1ccccc1)c1ccccc1 | [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] | 95.7 | [{"value": 93.0, "product": "O=C(CCCCCNC(=O)NC1=CC=CC=C1)CSC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.7, "product": "O=C(CCCCCNC(=O)NC1=CC=CC=C1)CSC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 7-amino-1-tritylsulfanyl-heptan-2-one (0.36 g, 0.86 mmol) in dichloromethane (10 mL) was added phenylisocyanate (0.10 mL, 0.92 mmol). The mixture was stirred at room temperature for 2 h. Solvent was then removed in vacuo and the crude product was purified by column chromatography (dichloromethane/MeOH=... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | ClCCl | null | 2 | NCCCCCC(=O)CSC(c1ccccc1)(c1ccccc1)c1ccccc1.O=C=Nc1ccccc1>ClCCl>O=C(CCCCCNC(=O)Nc1ccccc1)CSC(c1ccccc1)(c1ccccc1)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a6670014d6824106b82c37823a9dd189 | O=C(CS)NCCCCCNC(=O)Nc1ccccc1.O=C=NCc1ccccc1>>O=C(CS)NCCCCCNC(=O)NCc1ccccc1 | SCC(=O)NCCCCCNC(=O)NC1=CC=CC=C1.C(C1=CC=CC=C1)N=C=O>>C(C1=CC=CC=C1)NC(NCCCCCNC(CS)=O)=O | c1ccc(N[C:12]([NH:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][NH:5][C:2](=[O:1])[CH2:3][SH:4])=[O:13])cc1.O=C=[N:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[O:1]=[C:2]([CH2:3][SH:4])[NH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:13])[NH:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | O=C(CS)NCCCCCNC(=O)Nc1ccccc1.O=C=NCc1ccccc1 | O=C(CS)NCCCCCNC(=O)NCc1ccccc1 | null | null | null | Acylation | OtherReaction | 997a890dafa955c3130c49973d0afeebf85b599849c6eb3f0b38291cb66b3987 | 22ae2e47c0f9d9608f1cd96e274d7483289cea4f5380556a255e5dcab79311e7 | c1ccccc1 | O=C=[N;H0;D2;+0:1]-[C:2]-[c:3].[C:4]-[#7:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-N-c1:c:c:c:c:c:1>>[C:4]-[#7:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[NH;D2;+0:1]-[C:2]-[c:3] | null | [] | null | null | null | null | Compound 11 was prepared using the methodology described for the preparation of Compound 9, by substituting phenylisocyanate with benzylisocyanate. 1H NMR (300 MHz, DMSO-d6) δ (ppm) 7.98 (br s, 1H), 7.35-7.18 (m, 5H), 6.27 (br s, 1H), 5.91 (br s, 1H), 4.19 (s, 2H), 3.07 (d, J=8.1 Hz, 2H), 3.02 (m, 4H), 2.71 (t, J=8.1 H... | 10.6084/m9.figshare.5104873.v1 | null | Urea.Isocyanate | Urea | c1ccccc1 | null | c1ccccc1 | HO- | null | null | null | O=C(CS)NCCCCCNC(=O)Nc1ccccc1.O=C=NCc1ccccc1>>O=C(CS)NCCCCCNC(=O)NCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-29509cc1ce7e4b3f968edc2171438e52 | CN(C)c1ccc(CNC(=O)NCCCC(=O)NO)cc1.NCC(O)c1ccccc1>>O=C(CCCNC(=O)NCC(O)c1ccccc1)NO | CN(C1=CC=C(CNC(NCCCC(=O)NO)=O)C=C1)C.NCC(O)C1=CC=CC=C1>>ONC(CCCNC(=O)NCC(C1=CC=CC=C1)O)=O | CN(C)c1ccc(CN[C:7]([NH:6][CH2:5][CH2:4][CH2:3][C:2](=[O:1])[NH:19][OH:20])=[O:8])cc1.[NH2:9][CH2:10][CH:11]([OH:12])[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:8])[NH:9][CH2:10][CH:11]([OH:12])[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[NH:19][OH:20] | CN(C)c1ccc(CNC(=O)NCCCC(=O)NO)cc1.NCC(O)c1ccccc1 | O=C(CCCNC(=O)NCC(O)c1ccccc1)NO | null | null | null | Acylation | OtherReaction | 582f6ef5382ebd5e48252e738466d893c5ee2b077cb67f852c2b3d7225820053 | 0d4269d1abb31eda25c7cd91c24eadac3777eb70ce7cce8a6d7982c94492f078 | c1ccccc1 | C-N(-C)-c1:c:c:c(-C-N-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[C:4]):c:c:1.[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[C:4] | null | [] | null | null | null | null | Compound 15 was prepared using the methodology described for the preparation of compound 2, by substituting 4-dimethylaminobenzylamine dihydrochloride with 2-amino-1-phenyl-ethanol. 1H NMR (CD3OD) δ 7.42-7.24 (m, 5H), 4.73 (dd, J=7.8, 4.2 Hz, 1H), 3.43 (dd, J=13.8, 4.2 Hz, 1H), 3.26 (dd, J=13.8, 7.8 Hz, 1H), 3.14 (t, J... | 10.6084/m9.figshare.5104873.v1 | null | Urea.Primary amine.Tertiary amine | Urea | c1ccccc1 | null | c1ccccc1 | Other | null | null | null | CN(C)c1ccc(CNC(=O)NCCCC(=O)NO)cc1.NCC(O)c1ccccc1>>O=C(CCCNC(=O)NCC(O)c1ccccc1)NO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b9591aaa88b34c50ad6e35f510dc7980 | CN(C)c1ccc(CNC(=O)NCCCC(=O)NO)cc1.NCCc1ccccc1>>O=C(CCCNC(=O)NCCc1ccccc1)NO | CN(C1=CC=C(CNC(NCCCC(=O)NO)=O)C=C1)C.C(CC1=CC=CC=C1)N>>ONC(CCCNC(=O)NCCC1=CC=CC=C1)=O | CN(C)c1ccc(CN[C:7]([NH:6][CH2:5][CH2:4][CH2:3][C:2](=[O:1])[NH:18][OH:19])=[O:8])cc1.[NH2:9][CH2:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:8])[NH:9][CH2:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[NH:18][OH:19] | CN(C)c1ccc(CNC(=O)NCCCC(=O)NO)cc1.NCCc1ccccc1 | O=C(CCCNC(=O)NCCc1ccccc1)NO | null | null | null | Acylation | OtherReaction | 582f6ef5382ebd5e48252e738466d893c5ee2b077cb67f852c2b3d7225820053 | 0d4269d1abb31eda25c7cd91c24eadac3777eb70ce7cce8a6d7982c94492f078 | c1ccccc1 | C-N(-C)-c1:c:c:c(-C-N-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[C:4]):c:c:1.[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[C:4] | null | [] | null | null | null | null | Compound 1 was prepared using the methodology described for the preparation of compound 2, by substituting 4-dimethylaminobenzylamine dihydrochloride with phenethylamine. 1H NMR (CD3OD) δ 7.30-7.15 (m, 5H), 3.34 (t, J=6.9 Hz, 2H), 3.11 (t, J=7.2 Hz, 2H), 2.76 (t, J=7.2 Hz, 2H), 2.09 (t, J=7.5Hz, 2H), 1.73 (m, 2H). 13C ... | 10.6084/m9.figshare.5104873.v1 | null | Urea.Primary amine.Tertiary amine | Urea | c1ccccc1 | null | c1ccccc1 | Other | null | null | null | CN(C)c1ccc(CNC(=O)NCCCC(=O)NO)cc1.NCCc1ccccc1>>O=C(CCCNC(=O)NCCc1ccccc1)NO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-410a56935e554501b6be0dc88cc96e44 | COC(=O)CCCCCCC(=O)NC12CC3CC(CC(C3)C1)C2.NO>>O=C(CCCCCCC(=O)NC12CC3CC(CC(C3)C1)C2)NO | [Na].Cl.NO.[Na].COC(CCCCCCC(NC12CC3CC(CC(C1)C3)C2)=O)=O.C(C)(=O)O>>ONC(CCCCCCC(=O)NC12CC3CC(CC(C1)C3)C2)=O | CO[C:2](=[O:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9](=[O:10])[NH:11][C:12]12[CH2:13][CH:14]3[CH2:15][CH:16]([CH2:17][CH:18]([CH2:19]3)[CH2:20]1)[CH2:21]2.[NH2:22][OH:23]>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9](=[O:10])[NH:11][C:12]12[CH2:13][CH:14]3[CH2:15][CH:16]([CH2:17][CH:18]([CH2:19]... | COC(=O)CCCCCCC(=O)NC12CC3CC(CC(C3)C1)C2.NO | O=C(CCCCCCC(=O)NC12CC3CC(CC(C3)C1)C2)NO | null | C=1C=CC2=C(C1)C(=O)OC2(C=3C=CC(=CC3)O)C=4C=CC(=CC4)O | O.CO | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | C1C2CC3CC1CC(C2)C3 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[O;D1;H1:6]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[O;D1;H1:6] | 68 | [{"value": 68.0, "product": "ONC(CCCCCCC(=O)NC12CC3CC(CC(C1)C3)C2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.0, "product": "ONC(CCCCCCC(=O)NC12CC3CC(CC(C1)C3)C2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a first solution of hydroxylamine hydrochloride (66 mg, 0.950 mmol) and phenolphthalein (0.5 mg) in methanol (3 mL), was added dropwise a second solution of sodium metal (33 mg, 1.435 mmol) in methanol (3 mL) via additional funnel until a pink endpoint was reached and precipitate appeared. To the reaction mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | C1C2CC3CC1CC(C2)C3 | HO- | C=1C=CC2=C(C1)C(=O)OC2(C=3C=CC(=CC3)O)C=4C=CC(=CC4)O.O.CO | null | 24 | COC(=O)CCCCCCC(=O)NC12CC3CC(CC(C3)C1)C2.NO>C=1C=CC2=C(C1)C(=O)OC2(C=3C=CC(=CC3)O)C=4C=CC(=CC4)O.O.CO>O=C(CCCCCCC(=O)NC12CC3CC(CC(C3)C1)C2)NO |
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