dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1218cddf6284426e962b405ad48bf739 | COC(=O)c1cc(-c2ccc(OC)c(F)c2)n[nH]c1=O.ClCC=Cc1ccc(Cl)cc1>>COC(=O)c1cc(-c2ccc(OC)c(F)c2)nn(CC=Cc2ccc(Cl)cc2)c1=O | FC1=C(C=CC(=C1)F)C=1C=C(C(N(N1)CC(C)C)=O)CO.FC=1C=C(C=CC1OC)C=1C=C(C(NN1)=O)C(=O)OC.ClC1=CC=C(C=CCCl)C=C1>>ClC1=CC=C(C=CCN2N=C(C=C(C2=O)C(=O)OC)C2=CC(=C(C=C2)OC)F)C=C1 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([O:12][CH3:13])[c:14]([F:15])[cH:16]2)[n:17][nH:18][c:29]1=[O:30].Cl[CH2:19][CH:20]=[CH:21][c:22]1[cH:23][cH:24][c:25]([Cl:26])[cH:27][cH:28]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([O:12][CH3:13])[c:14]([F:15])[cH:16]... | COC(=O)c1cc(-c2ccc(OC)c(F)c2)n[nH]c1=O.ClCC=Cc1ccc(Cl)cc1 | COC(=O)c1cc(-c2ccc(OC)c(F)c2)nn(CC=Cc2ccc(Cl)cc2)c1=O | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 456217c8bdd4490079dbc0339e1b1eedc560d0b24ec9d54c4ed1fbd8e71fb3dc | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1ccc(-c2ccccc2)nn1CC=Cc1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]=[C:3]-[c:4].[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](=[O;D1;H0:10]):[nH;D2;+0:11]:[#7;a:12]:[c:13]>>[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](=[O;D1;H0:10]):[n;H0;D3;+0:11](-[CH2;D2;+0:1]-[C:2]=[C:3]-[c:4]):[#7;a:12]:[c:13] | 51.1 | [{"value": 51.1, "product": "ClC1=CC=C(C=CCN2N=C(C=C(C2=O)C(=O)OC)C2=CC(=C(C=C2)OC)F)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (6), 6-(3-fluoro-4-methoxyphenyl)-4-methoxycarbonyl-2H-pyridazin-3-one and 4-chlorocinnamyl chloride were reacted to yield the title compound as a pale yellow crystalline powder (yield: 51.1%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cnncc1 | c1ccnnc1 | c1ccnnc1.c1ccccc1.c1ccccc1 | HCl | null | null | null | COC(=O)c1cc(-c2ccc(OC)c(F)c2)n[nH]c1=O.ClCC=Cc1ccc(Cl)cc1>>COC(=O)c1cc(-c2ccc(OC)c(F)c2)nn(CC=Cc2ccc(Cl)cc2)c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c3de29e6ed0e4d46a8fd09b899695f45 | COC(=O)c1cc(-c2ccc(OC)c(F)c2)nn(CC=Cc2ccc(Cl)cc2)c1=O>>COc1ccc(-c2cc(C(=O)O)c(=O)n(CC=Cc3ccc(Cl)cc3)n2)cc1F | FC1=C(C=CC(=C1)F)C=1C=C(C(N(N1)CC(C)C)=O)COS(=O)(=O)C.ClC1=CC=C(C=CCN2N=C(C=C(C2=O)C(=O)OC)C2=CC(=C(C=C2)OC)F)C=C1>>C(=O)(O)C=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC=CC1=CC=C(C=C1)Cl)=O | C[O:12][C:10]([c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:28]([F:29])[cH:27]2)[n:26][n:15]([CH2:16][CH:17]=[CH:18][c:19]2[cH:20][cH:21][c:22]([Cl:23])[cH:24][cH:25]2)[c:13]1=[O:14])=[O:11]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([C:10](=[O:11])[OH:12])[c:13](=[O:14])[n:15]([CH2:16][CH:17]... | COC(=O)c1cc(-c2ccc(OC)c(F)c2)nn(CC=Cc2ccc(Cl)cc2)c1=O | COc1ccc(-c2cc(C(=O)O)c(=O)n(CC=Cc3ccc(Cl)cc3)n2)cc1F | null | null | null | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1ccc(-c2ccccc2)nn1CC=Cc1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 98.2 | [{"value": 98.2, "product": "C(=O)(O)C=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC=CC1=CC=C(C=C1)Cl)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (7), 2-(4-chlorocinnamyl)-6-(3-fluoro-4-methoxyphenyl)-4-methoxycarbonyl-2H-pyridazin-3-one was reacted to yield the title compound as a pale yellow crystalline powder (yield: 98.2%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccnnc1.c1ccccc1 | Other | null | null | null | COC(=O)c1cc(-c2ccc(OC)c(F)c2)nn(CC=Cc2ccc(Cl)cc2)c1=O>>COc1ccc(-c2cc(C(=O)O)c(=O)n(CC=Cc3ccc(Cl)cc3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ae51cee905cc4e5dbff0cb5b0ddd22c4 | COc1ccc(-c2cc(C(=O)O)c(=O)n(CC=Cc3ccc(Cl)cc3)n2)cc1F>>COc1ccc(-c2cc(CO)c(=O)n(CC=Cc3ccc(Cl)cc3)n2)cc1F | FC1=C(C=CC(=C1)F)C=1C=C(C(N(N1)CC(C)C)=O)CN1C(C=2C(C1=O)=CC=CC2)=O.C(=O)(O)C=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC=CC1=CC=C(C=C1)Cl)=O>>ClC1=CC=C(C=CCN2N=C(C=C(C2=O)CO)C2=CC(=C(C=C2)OC)F)C=C1 | O=[C:10]([c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:27]([F:28])[cH:26]2)[n:25][n:14]([CH2:15][CH:16]=[CH:17][c:18]2[cH:19][cH:20][c:21]([Cl:22])[cH:23][cH:24]2)[c:12]1=[O:13])[OH:11]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH2:10][OH:11])[c:12](=[O:13])[n:14]([CH2:15][CH:16]=[CH:17][c:1... | COc1ccc(-c2cc(C(=O)O)c(=O)n(CC=Cc3ccc(Cl)cc3)n2)cc1F | COc1ccc(-c2cc(CO)c(=O)n(CC=Cc3ccc(Cl)cc3)n2)cc1F | null | null | null | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | O=c1ccc(-c2ccccc2)nn1CC=Cc1ccccc1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[#7;a:7](-[C:8]-[C:9]=[C:10]):[c:11]:1=[O;D1;H0:12]>>[C:10]=[C:9]-[C:8]-[#7;a:7]1:[#7;a:6]:[c:5]:[c:4]:[c:3](-[CH2;D2;+0:1]-[O;D1;H1:2]):[c:11]:1=[O;D1;H0:12] | 17 | [{"value": 17.0, "product": "ClC1=CC=C(C=CCN2N=C(C=C(C2=O)CO)C2=CC(=C(C=C2)OC)F)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (8), 4-carboxy-2-(4-chlorocinnamyl)-6-(3-fluoro-4-methoxyphenyl)-2H-pyridazin-3-one was reacted to yield the title compound as pale yellow crystals (yield: 17.0%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccccc1.c1ccnnc1.c1ccccc1 | Other | null | null | null | COc1ccc(-c2cc(C(=O)O)c(=O)n(CC=Cc3ccc(Cl)cc3)n2)cc1F>>COc1ccc(-c2cc(CO)c(=O)n(CC=Cc3ccc(Cl)cc3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0cb6dbb54fcd4d7bbc4967067b9d59ea | CN1CCNCC1.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC=Cc3ccc(Cl)cc3)n2)cc1F>>COc1ccc(-c2cc(CN3CCN(C)CC3)c(=O)n(CC=Cc3ccc(Cl)cc3)n2)cc1F | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O.ClC1=CC=C(C=CCN2N=C(C=C(C2=O)COS(=O)(=O)C)C2=CC(=C(C=C2)OC)F)C=C1.CN1CCNCC1>>ClC1=CC=C(C=CCN2N=C(C=C(C2=O)CN2CCN(CC2)C)C2=CC(=C(C=C2)OC)F)C=C1 | [NH:11]1[CH2:12][CH2:13][N:14]([CH3:15])[CH2:16][CH2:17]1.CS(=O)(=O)O[CH2:10][c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:33]([F:34])[cH:32]2)[n:31][n:20]([CH2:21][CH:22]=[CH:23][c:24]2[cH:25][cH:26][c:27]([Cl:28])[cH:29][cH:30]2)[c:18]1=[O:19]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH2:... | CN1CCNCC1.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC=Cc3ccc(Cl)cc3)n2)cc1F | COc1ccc(-c2cc(CN3CCN(C)CC3)c(=O)n(CC=Cc3ccc(Cl)cc3)n2)cc1F | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | bc40e881c80f733cc18ae6a4c32c0d2e3ac9ce7b07d3a2cb609684e869dc6007 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1c(CN2CCNCC2)cc(-c2ccccc2)nn1CC=Cc1ccccc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[#7;a:6](-[C:7]-[C:8]=[C:9]):[c:10]:1=[O;D1;H0:11].[#7:12]1-[C:13]-[C:14]-[NH;D2;+0:15]-[C:16]-[C:17]-1>>[C:9]=[C:8]-[C:7]-[#7;a:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:15]2-[C:14]-[C:13]-[#7:12]-[C:17]-[C:16]-2):[c:10]:1=[O;D1;H0:11] | 66.3 | [{"value": 66.3, "product": "ClC1=CC=C(C=CCN2N=C(C=C(C2=O)CN2CCN(CC2)C)C2=CC(=C(C=C2)OC)F)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (10), 2-(4-chlorocinnamyl)-6-(3-fluoro-4-methoxyphenyl)-4-methanesulfonyloxymethyl-2H-pyridazin-3-one and 1-methylpiperazine were reacted to yield the title compound as pale brown neeldes (yield: 66.3%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.c1ccnnc1.C1C[NH]CC[NH]1.c1ccccc1 | MsOH.HO- | null | null | null | CN1CCNCC1.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC=Cc3ccc(Cl)cc3)n2)cc1F>>COc1ccc(-c2cc(CN3CCN(C)CC3)c(=O)n(CC=Cc3ccc(Cl)cc3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-05e673c9e6fa437aa9ab215ba6dafd87 | COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC=Cc3ccc(Cl)cc3)n2)cc1F.OCCN1CCNCC1>>COc1ccc(-c2cc(CN3CCN(CCO)CC3)c(=O)n(CC=Cc3ccc(Cl)cc3)n2)cc1F | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O.ClC1=CC=C(C=CCN2N=C(C=C(C2=O)COS(=O)(=O)C)C2=CC(=C(C=C2)OC)F)C=C1.N1(CCNCC1)CCO>>ClC1=CC=C(C=CCN2N=C(C=C(C2=O)CN2CCN(CC2)CCO)C2=CC(=C(C=C2)OC)F)C=C1 | CS(=O)(=O)O[CH2:10][c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:35]([F:36])[cH:34]2)[n:33][n:22]([CH2:23][CH:24]=[CH:25][c:26]2[cH:27][cH:28][c:29]([Cl:30])[cH:31][cH:32]2)[c:20]1=[O:21].[NH:11]1[CH2:12][CH2:13][N:14]([CH2:15][CH2:16][OH:17])[CH2:18][CH2:19]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[c... | COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC=Cc3ccc(Cl)cc3)n2)cc1F.OCCN1CCNCC1 | COc1ccc(-c2cc(CN3CCN(CCO)CC3)c(=O)n(CC=Cc3ccc(Cl)cc3)n2)cc1F | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | bc40e881c80f733cc18ae6a4c32c0d2e3ac9ce7b07d3a2cb609684e869dc6007 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1c(CN2CCNCC2)cc(-c2ccccc2)nn1CC=Cc1ccccc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[#7;a:6](-[C:7]-[C:8]=[C:9]):[c:10]:1=[O;D1;H0:11].[#7:12]1-[C:13]-[C:14]-[NH;D2;+0:15]-[C:16]-[C:17]-1>>[C:9]=[C:8]-[C:7]-[#7;a:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:15]2-[C:14]-[C:13]-[#7:12]-[C:17]-[C:16]-2):[c:10]:1=[O;D1;H0:11] | 65.1 | [{"value": 65.1, "product": "ClC1=CC=C(C=CCN2N=C(C=C(C2=O)CN2CCN(CC2)CCO)C2=CC(=C(C=C2)OC)F)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (10), 2-(4-chlorocinnamyl)-6-(3-fluoro-4-methoxyphenyl)-4-methanesulfonyloxymethyl-2H-pyridazin-3-one and 1-piperazineethanol were reacted to yield the title compound as slightly-yellow needles (yield: 65.1%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.c1ccnnc1.C1C[NH]CC[NH]1.c1ccccc1 | MsOH.HO- | null | null | null | COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC=Cc3ccc(Cl)cc3)n2)cc1F.OCCN1CCNCC1>>COc1ccc(-c2cc(CN3CCN(CCO)CC3)c(=O)n(CC=Cc3ccc(Cl)cc3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-75f5140c9d8a44fa82529fda053a0ac4 | BrC(Br)(Br)Br.COc1ccc(-c2nn(C3CC3)c(=O)c(CO)c2C)cc1F>>COc1ccc(-c2cc(CBr)c(=O)n(CC3CC3)n2)cc1F | C1(CC1)N1N=C(C(=C(C1=O)CO)C)C1=CC(=C(C=C1)OC)F.C(Br)(Br)(Br)Br.N1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>BrCC=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1CC1)=O | BrC(Br)(Br)[Br:11].C[c:8]1[c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:21]([F:22])[cH:20]2)[n:19][n:14]([CH:15]2[CH2:16][CH2:18]2)[c:12](=[O:13])[c:9]1[CH2:10]O>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH2:10][Br:11])[c:12](=[O:13])[n:14]([CH2:15][CH:16]3[CH2:17][CH2:18]3)[n:19]2)[cH:20][c:21]1[F:22] | BrC(Br)(Br)Br.COc1ccc(-c2nn(C3CC3)c(=O)c(CO)c2C)cc1F | COc1ccc(-c2cc(CBr)c(=O)n(CC3CC3)n2)cc1F | null | null | O1CCCC1 | Functional Group Interconversion | OtherReaction | 8f3e4f5e5a276936e09935a7fd0012eeeeccce5c831ce314373f7a4dc04c316e | 2c6b51fb1e17cb2c93d565e0423c75825df2c8e11c870e0c98b278f20ba9f3ad | O=c1ccc(-c2ccccc2)nn1CC1CC1 | Br-C(-Br)(-Br)-[Br;H0;D1;+0:1].C-[c;H0;D3;+0:2]1:[c:3](-[c:4]):[#7;a:5]:[#7;a:6](-[CH;D3;+0:7]2-[CH2;D2;+0:8]-[CH2;D2;+0:9]-2):[c:10](=[O;D1;H0:11]):[c:12]:1-[CH2;D2;+0:13]-O>>[Br;H0;D1;+0:1]-[CH2;D2;+0:13]-[c:12]1:[cH;D2;+0:2]:[c:3](-[c:4]):[#7;a:5]:[#7;a:6](-[CH2;D2;+0:7]-[CH;D3;+0:8]2-[C:14]-[CH2;D2;+0:9]-2):[c:10]:... | 69.5 | [{"value": 69.5, "product": "BrCC=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1CC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.2, "product": "BrCC=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 2-Cyclopropyl-methyl-6-(3-fluoro-4-methoxyphenyl)-4-hydroxymethyl-2H-pyridazin-3-one (185 mg, 0.61 mmol), carbon tetrabromide (404 mg, 1.2 mmol) and pyridine (48 mg, 0.61 mmol) were dissolved in tetrahydrofuran (3 mL), and under ice-cold stirring, a solution of triphenylphosphine (319 mg, 1.2 mmol) in tetrahydrofuran (... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Primary alcohol | Primary halide | c1ccnnc1.C1CC1 | c1ccnnc1.C1CC1 | c1ccccc1.c1ccnnc1.C1CC1 | HBr | O1CCCC1 | null | 1 | BrC(Br)(Br)Br.COc1ccc(-c2nn(C3CC3)c(=O)c(CO)c2C)cc1F>O1CCCC1>COc1ccc(-c2cc(CBr)c(=O)n(CC3CC3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-64b894aee23246cebcc958882c411997 | CC(C)(C)OC(=O)CC(=O)OC(C)(C)C.COc1ccc(-c2cc(CBr)c(=O)n(CC3CC3)n2)cc1F>>COc1ccc(-c2cc(CC(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(=O)n(CC3CC3)n2)cc1F | O.[H-].[Na+].C(CC(=O)OC(C)(C)C)(=O)OC(C)(C)C.BrCC=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1CC1)=O>>C1(CC1)CN1N=C(C=C(C1=O)CC(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)C1=CC(=C(C=C1)OC)F | [CH2:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25].Br[CH2:10][c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:35]([F:36])[cH:34]2)[n:33][n:28]([CH2:29][CH:30]2[CH2:31][CH2:32]2)[c:26]1=[O:27]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:... | CC(C)(C)OC(=O)CC(=O)OC(C)(C)C.COc1ccc(-c2cc(CBr)c(=O)n(CC3CC3)n2)cc1F | COc1ccc(-c2cc(CC(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(=O)n(CC3CC3)n2)cc1F | null | null | CN(C=O)C | C-C Coupling | OtherReaction | 8175b6573d6439ec7ccc45bf6b48843ab56b46dccfc6504384c4766d09f35cc7 | d1817e44576d3a158547867a56245217a593d4f828a6d6dfaa8ed11276894e44 | O=c1ccc(-c2ccccc2)nn1CC1CC1 | Br-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:1=[O;D1;H0:9].[C;D1;H3:10]-[C:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[#8:14]-[C:15](=[O;D1;H0:16])-[CH2;D2;+0:17]-[C:18](=[O;D1;H0:19])-[#8:20]-[C:21](-[C;D1;H3:22])(-[C;D1;H3:23])-[C;D1;H3:24]>>[C:7]-[#7;a:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[CH;... | 61.8 | [{"value": 61.8, "product": "C1(CC1)CN1N=C(C=C(C1=O)CC(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)C1=CC(=C(C=C1)OC)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 0.1, "product": "C1(CC1)CN1N=C(C=C(C1=O)CC(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)C1=CC(=C(C=C1)OC)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | After 55% sodium hydride (322 mg, 7.38 mmol) was added to a solution of di-tert-butyl malonate (970 mg, 4.48 mmol) in N,N-dimethylformamide (10 mL), 4-bromomethyl-2-cyclopropylmethyl-6-(3-fluoro-4-methoxyphenyl)-2H-pyridazin-3-one (1.8 g, 4.90 mmol) was added under ice-cold stirring. The reaction mixture was stirred at... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ester | Ester.Ester | null | null | c1ccccc1.c1ccnnc1.C1CC1 | HBr | CN(C=O)C | null | 1 | CC(C)(C)OC(=O)CC(=O)OC(C)(C)C.COc1ccc(-c2cc(CBr)c(=O)n(CC3CC3)n2)cc1F>CN(C=O)C>COc1ccc(-c2cc(CC(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(=O)n(CC3CC3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-acc6327e872d44b5954e4f6a3294ed3c | COc1ccc(-c2cc(CC(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(=O)n(CC3CC3)n2)cc1F>>COc1ccc(-c2cc(CCC(=O)O)c(=O)n(CC3CC3)n2)cc1F | FC(C(=O)O)(F)F.C1(CC1)CN1N=C(C=C(C1=O)CC(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)C1=CC(=C(C=C1)OC)F>>C(=O)(O)CCC=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1CC1)=O | CC(C)(C)OC(=O)[CH:11]([CH2:10][c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:24]([F:25])[cH:23]2)[n:22][n:17]([CH2:18][CH:19]2[CH2:20][CH2:21]2)[c:15]1=[O:16])[C:12](=[O:13])[O:14]C(C)(C)C>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH2:10][CH2:11][C:12](=[O:13])[OH:14])[c:15](=[O:16])[n:17]([C... | COc1ccc(-c2cc(CC(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(=O)n(CC3CC3)n2)cc1F | COc1ccc(-c2cc(CCC(=O)O)c(=O)n(CC3CC3)n2)cc1F | null | null | null | Reduction | OtherReaction | 73d165f371e7be9e7ac8a17da558f54492bf9b0746a90d7cc3220d78efbe0c09 | 60f3a79f391ea73b07965c28fa39ab5eb6558d5e98c32a693ba93254730088b7 | O=c1ccc(-c2ccccc2)nn1CC1CC1 | C-C(-C)(-C)-O-C(=O)-[CH;D3;+0:1](-[C:2]-[c:3]:[c:4]:[#7;a:5])-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C(-C)(-C)-C>>[#7;a:5]:[c:4]:[c:3]-[C:2]-[CH2;D2;+0:1]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8] | 94.7 | [{"value": 94.7, "product": "C(=O)(O)CCC=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1CC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.5, "product": "C(=O)(O)CCC=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Trifluoroacetic acid (21 mL) was added to 2-cyclopropylmethyl-4-[2,2-di(tert-butoxycarbonyl)ethyl]-6-(3-fluoro-4-methoxyphenyl)-2H-pyridazin-3-one (1.39 g, 2.77 mmol), and the mixture was stirred at room temperature for 30 minutes. The solvent was distilled off under reduced pressure, and toluene was added further, fol... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Boc.Boc | Carboxylic acid | null | null | c1ccccc1.c1ccnnc1.C1CC1 | HO- | null | null | 0.5 | COc1ccc(-c2cc(CC(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(=O)n(CC3CC3)n2)cc1F>>COc1ccc(-c2cc(CCC(=O)O)c(=O)n(CC3CC3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cb5e1d7ad4974c3aabb1630f8ff71cea | COc1ccc(-c2cc(CCC(=O)O)c(=O)n(CC3CC3)n2)cc1F>>COc1ccc(-c2cc(CCCO)c(=O)n(CC3CC3)n2)cc1F | FC1=C(C=CC(=C1)F)C=1C=C(C(N(N1)CC(C)C)=O)CN1C(C=2C(C1=O)=CC=CC2)=O.C(=O)(O)CCC=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1CC1)=O>>C1(CC1)CN1N=C(C=C(C1=O)CCCO)C1=CC(=C(C=C1)OC)F | O=[C:12]([CH2:11][CH2:10][c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:23]([F:24])[cH:22]2)[n:21][n:16]([CH2:17][CH:18]2[CH2:19][CH2:20]2)[c:14]1=[O:15])[OH:13]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH2:10][CH2:11][CH2:12][OH:13])[c:14](=[O:15])[n:16]([CH2:17][CH:18]3[CH2:19][CH2:20]3)[n... | COc1ccc(-c2cc(CCC(=O)O)c(=O)n(CC3CC3)n2)cc1F | COc1ccc(-c2cc(CCCO)c(=O)n(CC3CC3)n2)cc1F | null | null | null | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | O=c1ccc(-c2ccccc2)nn1CC1CC1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[C:3]-[C:4]>>[C:4]-[C:3]-[CH2;D2;+0:1]-[O;D1;H1:2] | 82.9 | [{"value": 82.9, "product": "C1(CC1)CN1N=C(C=C(C1=O)CCCO)C1=CC(=C(C=C1)OC)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (8), 4-(2-carboxyethyl)-2-cyclopropylmethyl-6-(3-fluoro-4-methoxyphenyl)-2H-pyridazin-3-one was reacted to yield the title compound as a brown oil (yield: 82.9%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccccc1.c1ccnnc1.C1CC1 | Other | null | null | null | COc1ccc(-c2cc(CCC(=O)O)c(=O)n(CC3CC3)n2)cc1F>>COc1ccc(-c2cc(CCCO)c(=O)n(CC3CC3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e5bf283c17274c55acf4bfd501a63d4b | CN1CCNCC1.COc1ccc(-c2cc(CCCOS(C)(=O)=O)c(=O)n(CC3CC3)n2)cc1F>>COc1ccc(-c2cc(CCCN3CCN(C)CC3)c(=O)n(CC3CC3)n2)cc1F | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O.C1(CC1)CN1N=C(C=C(C1=O)CCCOS(=O)(=O)C)C1=CC(=C(C=C1)OC)F.CN1CCNCC1>>C1(CC1)CN1N=C(C=C(C1=O)CCCN1CCN(CC1)C)C1=CC(=C(C=C1)OC)F | [NH:13]1[CH2:14][CH2:15][N:16]([CH3:17])[CH2:18][CH2:19]1.CS(=O)(=O)O[CH2:12][CH2:11][CH2:10][c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:29]([F:30])[cH:28]2)[n:27][n:22]([CH2:23][CH:24]2[CH2:25][CH2:26]2)[c:20]1=[O:21]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH2:10][CH2:11][CH2:12][N:13]... | CN1CCNCC1.COc1ccc(-c2cc(CCCOS(C)(=O)=O)c(=O)n(CC3CC3)n2)cc1F | COc1ccc(-c2cc(CCCN3CCN(C)CC3)c(=O)n(CC3CC3)n2)cc1F | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | bc40e881c80f733cc18ae6a4c32c0d2e3ac9ce7b07d3a2cb609684e869dc6007 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1c(CCCN2CCNCC2)cc(-c2ccccc2)nn1CC1CC1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | 62 | [{"value": 62.0, "product": "C1(CC1)CN1N=C(C=C(C1=O)CCCN1CCN(CC1)C)C1=CC(=C(C=C1)OC)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (10), 2-cyclopropylmethyl-6-(3-fluoro-4-methoxyphenyl)-4-(3-methanesulfonyloxypropyl)-2H-pyridazin-3-one and 1-methylpiperazine were reacted to yield the title compound as a yellow oil (yield: 62.0%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.c1ccnnc1.C1C[NH]CC[NH]1.C1CC1 | MsOH.HO- | null | null | null | CN1CCNCC1.COc1ccc(-c2cc(CCCOS(C)(=O)=O)c(=O)n(CC3CC3)n2)cc1F>>COc1ccc(-c2cc(CCCN3CCN(C)CC3)c(=O)n(CC3CC3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3168b7d94c754219aa02a878634ae871 | CNC.COc1ccc(-c2cc(CCCOS(C)(=O)=O)c(=O)n(CC3CC3)n2)cc1F>>COc1ccc(-c2cc(CCCN(C)C)c(=O)n(CC3CC3)n2)cc1F | C1(CC1)CN1N=C(C=C(C1=O)CCCOS(=O)(=O)C)C1=CC(=C(C=C1)OC)F.CNC>>C1(CC1)CN1N=C(C=C(C1=O)CCCN(C)C)C1=CC(=C(C=C1)OC)F | [NH:13]([CH3:14])[CH3:15].CS(=O)(=O)O[CH2:12][CH2:11][CH2:10][c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:25]([F:26])[cH:24]2)[n:23][n:18]([CH2:19][CH:20]2[CH2:21][CH2:22]2)[c:16]1=[O:17]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH2:10][CH2:11][CH2:12][N:13]([CH3:14])[CH3:15])[c:16](=[O:17... | CNC.COc1ccc(-c2cc(CCCOS(C)(=O)=O)c(=O)n(CC3CC3)n2)cc1F | COc1ccc(-c2cc(CCCN(C)C)c(=O)n(CC3CC3)n2)cc1F | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | ba24696731c43f94422863463da0ee528bfb8ec715fd228fe0a6c2ae67b49c25 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1ccc(-c2ccccc2)nn1CC1CC1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[NH;D2;+0:5]-[C;D1;H3:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:5](-[C;D1;H3:4])-[C;D1;H3:6] | 64.7 | [{"value": 64.7, "product": "C1(CC1)CN1N=C(C=C(C1=O)CCCN(C)C)C1=CC(=C(C=C1)OC)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 7, 2-cyclopropylmethyl-6-(3-fluoro-4-methoxyphenyl)-4-(3-methanesulfonyloxypropyl)-2H-pyridazin-3-one and dimethylamine were reacted to yield the title compound as a yellow powder (yield: 64.7%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | null | null | c1ccccc1.c1ccnnc1.C1CC1 | MsOH.HO- | null | null | null | CNC.COc1ccc(-c2cc(CCCOS(C)(=O)=O)c(=O)n(CC3CC3)n2)cc1F>>COc1ccc(-c2cc(CCCN(C)C)c(=O)n(CC3CC3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ef49fa90d7724a8e96e40b5cbe4b435d | CC(C)(C)OC(=O)N1CCNCC1.COc1ccc(-c2cc(CCCOS(C)(=O)=O)c(=O)n(CC3CC3)n2)cc1F>>COc1ccc(-c2cc(CCCN3CCN(C(=O)OC(C)(C)C)CC3)c(=O)n(CC3CC3)n2)cc1F | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O.C1(CC1)CN1N=C(C=C(C1=O)CCCOS(=O)(=O)C)C1=CC(=C(C=C1)OC)F.N1(CCNCC1)C(=O)OC(C)(C)C>>C1(CC1)CN1N=C(C=C(C1=O)CCCN1CCN(CC1)C(=O)OC(C)(C)C)C1=CC(=C(C=C1)OC)F | [NH:13]1[CH2:14][CH2:15][N:16]([C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[CH2:24][CH2:25]1.CS(=O)(=O)O[CH2:12][CH2:11][CH2:10][c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:35]([F:36])[cH:34]2)[n:33][n:28]([CH2:29][CH:30]2[CH2:31][CH2:32]2)[c:26]1=[O:27]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[... | CC(C)(C)OC(=O)N1CCNCC1.COc1ccc(-c2cc(CCCOS(C)(=O)=O)c(=O)n(CC3CC3)n2)cc1F | COc1ccc(-c2cc(CCCN3CCN(C(=O)OC(C)(C)C)CC3)c(=O)n(CC3CC3)n2)cc1F | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | bc40e881c80f733cc18ae6a4c32c0d2e3ac9ce7b07d3a2cb609684e869dc6007 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1c(CCCN2CCNCC2)cc(-c2ccccc2)nn1CC1CC1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | 76.9 | [{"value": 76.9, "product": "C1(CC1)CN1N=C(C=C(C1=O)CCCN1CCN(CC1)C(=O)OC(C)(C)C)C1=CC(=C(C=C1)OC)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (10), 2-cyclopropylmethyl-6-(3-fluoro-4-methoxyphenyl)-4-(3-methanesulfonyloxypropyl)-2H-pyridazin-3-one and tert-butyl 1-piperazinecarboxylate were reacted to yield the title compound as a yellow oil (yield: 76.9%).
Conditions: See reaction.notes.procedure_details.
Workup: were rea... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.c1ccnnc1.C1C[NH]CC[NH]1.C1CC1 | MsOH.HO- | null | null | null | CC(C)(C)OC(=O)N1CCNCC1.COc1ccc(-c2cc(CCCOS(C)(=O)=O)c(=O)n(CC3CC3)n2)cc1F>>COc1ccc(-c2cc(CCCN3CCN(C(=O)OC(C)(C)C)CC3)c(=O)n(CC3CC3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e4e0517e1a0e432fb39f25650571d446 | COc1ccc(-c2cc(CCCOS(C)(=O)=O)c(=O)n(CC3CC3)n2)cc1F.OCCNCCO>>COc1ccc(-c2cc(CCCN(CCO)CCO)c(=O)n(CC3CC3)n2)cc1F | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O.C1(CC1)CN1N=C(C=C(C1=O)CCCOS(=O)(=O)C)C1=CC(=C(C=C1)OC)F.N(CCO)CCO>>OCCN(CCO)CCCC=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1CC1)=O | CS(=O)(=O)O[CH2:12][CH2:11][CH2:10][c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:29]([F:30])[cH:28]2)[n:27][n:22]([CH2:23][CH:24]2[CH2:25][CH2:26]2)[c:20]1=[O:21].[NH:13]([CH2:14][CH2:15][OH:16])[CH2:17][CH2:18][OH:19]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH2:10][CH2:11][CH2:12][N:13]([... | COc1ccc(-c2cc(CCCOS(C)(=O)=O)c(=O)n(CC3CC3)n2)cc1F.OCCNCCO | COc1ccc(-c2cc(CCCN(CCO)CCO)c(=O)n(CC3CC3)n2)cc1F | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | ba24696731c43f94422863463da0ee528bfb8ec715fd228fe0a6c2ae67b49c25 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1ccc(-c2ccccc2)nn1CC1CC1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | 13.1 | [{"value": 13.1, "product": "OCCN(CCO)CCCC=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1CC1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (10), 2-cyclopropylmethyl-6-(3-fluoro-4-methoxyphenyl)-4-(3-methanesulfonyloxypropyl)-2H-pyridazin-3-one and diethanolamine were reacted to yield the title compound as a yellow oil (yield: 13.1%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | null | null | c1ccccc1.c1ccnnc1.C1CC1 | MsOH.HO- | null | null | null | COc1ccc(-c2cc(CCCOS(C)(=O)=O)c(=O)n(CC3CC3)n2)cc1F.OCCNCCO>>COc1ccc(-c2cc(CCCN(CCO)CCO)c(=O)n(CC3CC3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b29c56e897174da09d88d654baf61f7f | COc1ccc(-c2cc(CCCN3CCN(C(=O)OC(C)(C)C)CC3)c(=O)n(CC3CC3)n2)cc1F>>COc1ccc(-c2cc(CCCN)c(=O)n(CC3CC3)n2)cc1F | C1(CC1)CN1N=C(C=C(C1=O)CCCN1CCN(CC1)C(=O)OC(C)(C)C)C1=CC(=C(C=C1)OC)F.C1(CC1)CN1N=C(C=C(C1=O)CCCOS(=O)(=O)C)C1=CC(=C(C=C1)OC)F>>NCCCC=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1CC1)=O | CC(C)(C)OC(=O)N1CC[N:13]([CH2:12][CH2:11][CH2:10][c:9]2[cH:8][c:7](-[c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[c:23]([F:24])[cH:22]3)[n:21][n:16]([CH2:17][CH:18]3[CH2:19][CH2:20]3)[c:14]2=[O:15])CC1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH2:10][CH2:11][CH2:12][NH2:13])[c:14](=[O:15])[n:16]([CH2:17][CH:18]... | COc1ccc(-c2cc(CCCN3CCN(C(=O)OC(C)(C)C)CC3)c(=O)n(CC3CC3)n2)cc1F | COc1ccc(-c2cc(CCCN)c(=O)n(CC3CC3)n2)cc1F | null | null | null | Reduction | OtherReaction | 23146a52518addfb1c2672d9eda28be46306c0529900b58e4e443b48598a246d | 8db4ab69acf74a26aa2337e69e043c35d4e223d9c589e65301835fe886fa6f52 | O=c1ccc(-c2ccccc2)nn1CC1CC1 | C-C(-C)(-C)-O-C(=O)-N1-C-C-[N;H0;D3;+0:1](-[C:2]-[C:3])-C-C-1>>[C:3]-[C:2]-[NH2;D1;+0:1] | 67.8 | [{"value": 67.8, "product": "NCCCC=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1CC1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 24 (1), 2-cyclopropylmethyl-6-(3-fluoro-4-methoxyphenyl)-4-(3-methanesulfonyloxypropyl)-2H-pyridazin-3-one was reacted to yield a crude product. Without purification, the crude product was reacted further in accordance with the procedure of Example 24 (2) to yield the title compound a... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Tertiary amine.Boc | Primary amine | C1CNCC[NH]1 | null | c1ccccc1.c1ccnnc1.C1CC1 | HO- | null | null | null | COc1ccc(-c2cc(CCCN3CCN(C(=O)OC(C)(C)C)CC3)c(=O)n(CC3CC3)n2)cc1F>>COc1ccc(-c2cc(CCCN)c(=O)n(CC3CC3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-178d1c80d262496d81b1b38dcd50183e | CC(C)CBr.N#Cc1ccc(O)cc1>>CC(C)COc1ccc(C#N)cc1 | C(C(C)C)Br.C(#N)C1=CC=C(C=C1)O.C(C)N(CC)CC>>C(C(C)C)OC1=CC=C(C#N)C=C1 | Br[CH2:4][CH:2]([CH3:1])[CH3:3].[OH:5][c:6]1[cH:7][cH:8][c:9]([C:10]#[N:11])[cH:12][cH:13]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([C:10]#[N:11])[cH:12][cH:13]1 | CC(C)CBr.N#Cc1ccc(O)cc1 | CC(C)COc1ccc(C#N)cc1 | null | null | O.CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])-[C;D1;H3:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:3]-[C:2](-[C;D1;H3:4])-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8] | 85.6 | [{"value": 85.0, "product": "C(C(C)C)OC1=CC=C(C#N)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.6, "product": "C(C(C)C)OC1=CC=C(C#N)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 6 | HOUR | To a solution of 4-cyanophenol (1.2 g, 10 mmol) in dry DMF (20 mL) was added triethylamine (20 mmol) followed by i-butyl bromide (2.7 g, 20 mmol). The resulting reaction mixture was stirred at 100° C. for 6 h. After cooling to room temperature, the reaction mixture was diluted with water (100 mL) and extracted with eth... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | O.CN(C)C=O | 100 | 6 | CC(C)CBr.N#Cc1ccc(O)cc1>O.CN(C)C=O>CC(C)COc1ccc(C#N)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a2ee85c640ce4339a5e720ec558b5af4 | CCN(CC)CCCO.O=[N+]([O-])c1cc(O)ccc1Cl>>CCN(CC)CCCOc1ccc(Cl)c([N+](=O)[O-])c1 | ClC1=C(C=C(C=C1)O)[N+](=O)[O-].C(=O)([O-])[O-].[K+].[K+].CS(=O)(=O)Cl.C(C)N(CCCO)CC>>ClC1=C(C=C(C=C1)OCCCN(CC)CC)[N+](=O)[O-] | O[CH2:8][CH2:7][CH2:6][N:3]([CH2:2][CH3:1])[CH2:4][CH3:5].[OH:9][c:10]1[cH:11][cH:12][c:13]([Cl:14])[c:15]([N+:16](=[O:17])[O-:18])[cH:19]1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([Cl:14])[c:15]([N+:16](=[O:17])[O-:18])[cH:19]1 | CCN(CC)CCCO.O=[N+]([O-])c1cc(O)ccc1Cl | CCN(CC)CCCOc1ccc(Cl)c([N+](=O)[O-])c1 | null | null | CN(C)C=O.C(Cl)Cl | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccccc1 | O-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 90.7 | [{"value": 90.7, "product": "ClC1=C(C=C(C=C1)OCCCN(CC)CC)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | MsCl (6.0 mmol) was added dropwise at 0° C. to a stirred solution of 3-diethylamino-1-propanol (6.0 mmol), TEA (6.0 mmol) in anhydrous DCM (6 mL), and the mixture was stirred at the same temperature for 10 min, and at room temperature for additional 1 h. After the removal of the solvent in vacuo, the solid residue was ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccccc1 | HO- | CN(C)C=O.C(Cl)Cl | null | 0.166667 | CCN(CC)CCCO.O=[N+]([O-])c1cc(O)ccc1Cl>CN(C)C=O.C(Cl)Cl>CCN(CC)CCCOc1ccc(Cl)c([N+](=O)[O-])c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f375c00562a24af688c5e95063e27f6d | CCN(CC)CCCO.O=[N+]([O-])c1ccc(O)cc1F>>CCN(CC)CCCOc1ccc([N+](=O)[O-])c(F)c1 | FC=1C=C(C=CC1[N+](=O)[O-])O.CS(=O)(=O)[O-].C(C)N(CCCO)CC.C(=O)([O-])[O-].[K+].[K+]>>FC1=C(C=CC(=C1)OCCCN(CC)CC)[N+](=O)[O-] | O[CH2:8][CH2:7][CH2:6][N:3]([CH2:2][CH3:1])[CH2:4][CH3:5].[OH:9][c:10]1[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[c:17]([F:18])[cH:19]1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[c:17]([F:18])[cH:19]1 | CCN(CC)CCCO.O=[N+]([O-])c1ccc(O)cc1F | CCN(CC)CCCOc1ccc([N+](=O)[O-])c(F)c1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccccc1 | O-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | A solution of 3-fluoro-4-nitrophenol (2 mmol) and methanesulfonate of 3-diethylamino-1-propanol (2.5 mmol) in DMF (4 mL) is added with K2CO3 (4 mmol) and heated following the general procedure III (Step A). The product, 2-fluoro-4-(3-diethylamino-1-propoxy)nitrobenzene is obtained (470 mg) after purification using sili... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccccc1 | HO- | CN(C)C=O | null | null | CCN(CC)CCCO.O=[N+]([O-])c1ccc(O)cc1F>CN(C)C=O>CCN(CC)CCCOc1ccc([N+](=O)[O-])c(F)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2376017b04d24493a40d98ac5b74b779 | CCN(CC)CCCOc1ccc([N+](=O)[O-])c(F)c1.[NH4+]>>CCN(CC)CCCOc1ccc([N+](=O)[O-])c(N)c1 | FC1=C(C=CC(=C1)OCCCN(CC)CC)[N+](=O)[O-].C([O-])([O-])=O.[NH4+].[NH4+].CCOC(=O)C>>[N+](=O)([O-])C1=C(N)C=C(C=C1)OCCCN(CC)CC | F[c:17]1[c:13]([N+:14](=[O:15])[O-:16])[cH:12][cH:11][c:10]([O:9][CH2:8][CH2:7][CH2:6][N:3]([CH2:2][CH3:1])[CH2:4][CH3:5])[cH:19]1.[NH4+:18]>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[c:17]([NH2:18])[cH:19]1 | CCN(CC)CCCOc1ccc([N+](=O)[O-])c(F)c1.[NH4+] | CCN(CC)CCCOc1ccc([N+](=O)[O-])c(N)c1 | null | null | CN(C)C=O | Functional Group Interconversion | OtherReaction | 0b3f36c6e96a844ac8c671a85ab317446ee29bfa735a32d39184f4616cac3a55 | 560c85d40afb1a57d77cf3258abf3be5bba829f35224f8687bf9a1d4c1f94bd9 | c1ccccc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[NH4+;D0:7]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH2;D1;+0:7]):[c:2]:[c:3] | null | [] | 80 | CELSIUS | null | null | The nitro compound obtained as above (1.5 mmol) is dissolved in DMF (4 mL) and added with ammonium carbonate (500 mg). The reaction mixture is then heated at 80° C. for 48 h. EtOAc (2×10 mL). The combined organic layers are then washed with water and brine and dried over Na2SO4. Removal of the solvent in vacuo yielded ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Primary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HF | CN(C)C=O | 80 | null | CCN(CC)CCCOc1ccc([N+](=O)[O-])c(F)c1.[NH4+]>CN(C)C=O>CCN(CC)CCCOc1ccc([N+](=O)[O-])c(N)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a53bb23cec524e1b93bdd268e5e66548 | CCCCN.CCN(CC)CCCOc1ccc([N+](=O)[O-])c(F)c1>>CCCCNc1cc(OCCCN(CC)CC)ccc1[N+](=O)[O-] | FC1=C(C=CC(=C1)OCCCN(CC)CC)[N+](=O)[O-].C(CCC)N>>C(CCC)NC1=C(C=CC(=C1)OCCCN(CC)CC)[N+](=O)[O-] | [CH3:1][CH2:2][CH2:3][CH2:4][NH2:5].F[c:6]1[cH:7][c:8]([O:9][CH2:10][CH2:11][CH2:12][N:13]([CH2:14][CH3:15])[CH2:16][CH3:17])[cH:18][cH:19][c:20]1[N+:21](=[O:22])[O-:23]>>[CH3:1][CH2:2][CH2:3][CH2:4][NH:5][c:6]1[cH:7][c:8]([O:9][CH2:10][CH2:11][CH2:12][N:13]([CH2:14][CH3:15])[CH2:16][CH3:17])[cH:18][cH:19][c:20]1[N+:21... | CCCCN.CCN(CC)CCCOc1ccc([N+](=O)[O-])c(F)c1 | CCCCNc1cc(OCCCN(CC)CC)ccc1[N+](=O)[O-] | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccccc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[c:2]:[c:3] | null | [] | null | null | null | null | A solution of 2-fluoro-4-(3-diethylamino-1-propoxy)nitrobenzene (2 mmol; preparation described in Example 5) in THF (5 mL) is treated with n-butylamine (2.4 eq) at rt. After completion of the reaction, the reaction mixture is concentrated in vacuo. The residue is redissolved in EtOAc (10 mL), washed with saturated sodi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HF | C1CCOC1 | null | null | CCCCN.CCN(CC)CCCOc1ccc([N+](=O)[O-])c(F)c1>C1CCOC1>CCCCNc1cc(OCCCN(CC)CC)ccc1[N+](=O)[O-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a32838925aa044bb98e4a272dcdd9e10 | CCN(CC)CCCN.CCN(CC)CCCOc1ccc([N+](=O)[O-])c(F)c1>>CCN(CC)CCCNc1cc(OCCCN(CC)CC)ccc1[N+](=O)[O-] | FC1=C(C=CC(=C1)OCCCN(CC)CC)[N+](=O)[O-].C(C)N(CCCN)CC>>C(C)N(CCCNC1=C(C=CC(=C1)OCCCN(CC)CC)[N+](=O)[O-])CC | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][NH2:9].F[c:10]1[cH:11][c:12]([O:13][CH2:14][CH2:15][CH2:16][N:17]([CH2:18][CH3:19])[CH2:20][CH3:21])[cH:22][cH:23][c:24]1[N+:25](=[O:26])[O-:27]>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][NH:9][c:10]1[cH:11][c:12]([O:13][CH2:14][CH2:15][CH2:16][N:1... | CCN(CC)CCCN.CCN(CC)CCCOc1ccc([N+](=O)[O-])c(F)c1 | CCN(CC)CCCNc1cc(OCCCN(CC)CC)ccc1[N+](=O)[O-] | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccccc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[c:2]:[c:3] | null | [] | null | null | null | null | A solution of 2-fluoro-4-(3-diethylamino-1-propoxy)nitrobenzene (2 mmol; preparation described in Example 5) in THF (5 mL) is treated with 3-diethylamino-1-propylamine (2.4 mmol at rt. After completion of the reaction, the reaction mixture is concentrated in vacuo. The residue is redissolved in EtOAc (10 mL), washed wi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HF | C1CCOC1 | null | null | CCN(CC)CCCN.CCN(CC)CCCOc1ccc([N+](=O)[O-])c(F)c1>C1CCOC1>CCN(CC)CCCNc1cc(OCCCN(CC)CC)ccc1[N+](=O)[O-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8387d2f954384bf0b74112334218b3c6 | CCN.CCN(CC)CCCOc1ccc([N+](=O)[O-])c(F)c1>>CCNc1cc(OCCCN(CC)CC)ccc1[N+](=O)[O-] | FC1=C(C=CC(=C1)OCCCN(CC)CC)[N+](=O)[O-].C(C)N>>C(C)NC1=C(C=CC(=C1)OCCCN(CC)CC)[N+](=O)[O-] | [CH3:1][CH2:2][NH2:3].F[c:4]1[cH:5][c:6]([O:7][CH2:8][CH2:9][CH2:10][N:11]([CH2:12][CH3:13])[CH2:14][CH3:15])[cH:16][cH:17][c:18]1[N+:19](=[O:20])[O-:21]>>[CH3:1][CH2:2][NH:3][c:4]1[cH:5][c:6]([O:7][CH2:8][CH2:9][CH2:10][N:11]([CH2:12][CH3:13])[CH2:14][CH3:15])[cH:16][cH:17][c:18]1[N+:19](=[O:20])[O-:21] | CCN.CCN(CC)CCCOc1ccc([N+](=O)[O-])c(F)c1 | CCNc1cc(OCCCN(CC)CC)ccc1[N+](=O)[O-] | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccccc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[C;D1;H3:7]-[C:8]-[NH2;D1;+0:9]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C;D1;H3:7]):[c:2]:[c:3] | 88 | [{"value": 88.0, "product": "C(C)NC1=C(C=CC(=C1)OCCCN(CC)CC)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-fluoro-4-(3-diethylamino-1-propoxy)nitrobenzene (2 mmol; preparation described in Example 5) in THF (5 mL) is treated with ethylamine (4 mmol) at rt. After completion of the reaction, the reaction mixture is concentrated in vacuo. The residue is redissolved in EtOAc (10 mL), washed with saturated sodium... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HF | C1CCOC1 | null | null | CCN.CCN(CC)CCCOc1ccc([N+](=O)[O-])c(F)c1>C1CCOC1>CCNc1cc(OCCCN(CC)CC)ccc1[N+](=O)[O-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-af39e966e26540f5ac091befab22f4c6 | CCN(CC)CCCOc1ccc([N+](=O)[O-])c(F)c1.NCc1ccccc1>>CCN(CC)CCCOc1ccc([N+](=O)[O-])c(NCc2ccccc2)c1 | FC1=C(C=CC(=C1)OCCCN(CC)CC)[N+](=O)[O-].C(C1=CC=CC=C1)N>>C(C1=CC=CC=C1)NC1=C(C=CC(=C1)OCCCN(CC)CC)[N+](=O)[O-] | F[c:17]1[c:13]([N+:14](=[O:15])[O-:16])[cH:12][cH:11][c:10]([O:9][CH2:8][CH2:7][CH2:6][N:3]([CH2:2][CH3:1])[CH2:4][CH3:5])[cH:26]1.[NH2:18][CH2:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[c:17]([NH:18][... | CCN(CC)CCCOc1ccc([N+](=O)[O-])c(F)c1.NCc1ccccc1 | CCN(CC)CCCOc1ccc([N+](=O)[O-])c(NCc2ccccc2)c1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccccc2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[NH2;D1;+0:7]-[C:8]-[c:9]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:7]-[C:8]-[c:9]):[c:2]:[c:3] | 86.7 | [{"value": 86.7, "product": "C(C1=CC=CC=C1)NC1=C(C=CC(=C1)OCCCN(CC)CC)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-fluoro-4-(3-diethylamino-1-propoxy)nitrobenzene (2 mmol; preparation described in Example 5) in THF (5 mL) is treated with benzylamine (2.4 mmol) at rt. After completion of the reaction, the reaction mixture is concentrated in vacuo. The residue is redissolved in EtOAc (10 mL), washed with saturated sod... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HF | C1CCOC1 | null | null | CCN(CC)CCCOc1ccc([N+](=O)[O-])c(F)c1.NCc1ccccc1>C1CCOC1>CCN(CC)CCCOc1ccc([N+](=O)[O-])c(NCc2ccccc2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d05a77cbb12a408ea3040c2e02249524 | CCCN.CCN(CC)CCCOc1ccc([N+](=O)[O-])c(F)c1>>CCCNc1cc(OCCCN(CC)CC)ccc1[N+](=O)[O-] | FC1=C(C=CC(=C1)OCCCN(CC)CC)[N+](=O)[O-].C(CC)N>>C(CC)NC1=C(C=CC(=C1)OCCCN(CC)CC)[N+](=O)[O-] | [CH3:1][CH2:2][CH2:3][NH2:4].F[c:5]1[cH:6][c:7]([O:8][CH2:9][CH2:10][CH2:11][N:12]([CH2:13][CH3:14])[CH2:15][CH3:16])[cH:17][cH:18][c:19]1[N+:20](=[O:21])[O-:22]>>[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[cH:6][c:7]([O:8][CH2:9][CH2:10][CH2:11][N:12]([CH2:13][CH3:14])[CH2:15][CH3:16])[cH:17][cH:18][c:19]1[N+:20](=[O:21])[O-:22... | CCCN.CCN(CC)CCCOc1ccc([N+](=O)[O-])c(F)c1 | CCCNc1cc(OCCCN(CC)CC)ccc1[N+](=O)[O-] | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccccc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[c:2]:[c:3] | 87.3 | [{"value": 87.3, "product": "C(CC)NC1=C(C=CC(=C1)OCCCN(CC)CC)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-fluoro-4-(3-diethylamino-1-propoxy)nitrobenzene (2 mmol; preparation described in Example 5) in THF (5 mL) is treated with propylamine (3 mmol) at rt. After completion of the reaction, the reaction mixture is concentrated in vacuo. The residue is redissolved in EtOAc (10 mL), washed with saturated sodiu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HF | C1CCOC1 | null | null | CCCN.CCN(CC)CCCOc1ccc([N+](=O)[O-])c(F)c1>C1CCOC1>CCCNc1cc(OCCCN(CC)CC)ccc1[N+](=O)[O-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6fe2fc3ae60d43a599678970974d3fca | NN.O=[N+]([O-])c1ccc(Cl)nc1>>NNc1ccc([N+](=O)[O-])cn1 | ClC1=NC=C(C=C1)[N+](=O)[O-].O.NN>>[N+](=O)([O-])C=1C=CC(=NC1)NN | [NH2:1][NH2:2].Cl[c:3]1[cH:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][n:11]1>>[NH2:1][NH:2][c:3]1[cH:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][n:11]1 | NN.O=[N+]([O-])c1ccc(Cl)nc1 | NNc1ccc([N+](=O)[O-])cn1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | bbfd7563459ad1792ea1bdeb15b833ba71625ca5c9310b24f82e4f1a166d7f3e | 61806bbf8bb8981e140ee503663af0ef0e69dc4f34f6582f974a2e4218f7da88 | c1ccncc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[N;D1;H2:6]-[NH2;D1;+0:7]>>[N;D1;H2:6]-[NH;D2;+0:7]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | null | null | To a solution of 2-chloro-5-nitropyridine (30 mmol, 5.0 g) in absolute ethanol was added a solution of hydrazine hydrate (320 mmol, 15.8 g) in ethanol using syringe pump. At the end of the addition, the reaction was refrigerated. The named product precipitated from the reaction medium, was collected by filtration, and ... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Aromatic halide | Hydrazine | c1ccncc1 | c1ccncc1 | c1ccncc1 | HCl | C(C)O | null | null | NN.O=[N+]([O-])c1ccc(Cl)nc1>C(C)O>NNc1ccc([N+](=O)[O-])cn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e5691291fb0a4b04b21a9e9c660b0e4b | CCOC(=O)C(C(C)=O)C(C)=O.NNc1ccc(Br)cc1>>CCOC(=O)c1c(C)nn(-c2ccc(Br)cc2)c1C | Cl.BrC1=CC=C(C=C1)NN.C(C)OC(C(C(C)=O)C(C)=O)=O.C(Cl)(Cl)Cl>>C(C)OC(=O)C=1C(=NN(C1C)C1=CC=C(C=C1)Br)C | O=[C:7]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:18](=O)[CH3:19])[CH3:8].[NH2:9][NH:10][c:11]1[cH:12][cH:13][c:14]([Br:15])[cH:16][cH:17]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[n:9][n:10](-[c:11]2[cH:12][cH:13][c:14]([Br:15])[cH:16][cH:17]2)[c:18]1[CH3:19] | CCOC(=O)C(C(C)=O)C(C)=O.NNc1ccc(Br)cc1 | CCOC(=O)c1c(C)nn(-c2ccc(Br)cc2)c1C | null | null | N1=CC=CC=C1.C(C)O | Aromatic Heterocycle Formation | Pyrazole formation | ab164a2f07e9367856bf3c71fa902c37bbb79de5ea024b32fa79526bb18dc4d6 | 7abcc9a477ed734c13c96188d72c44fdd5cc90ff2d36e50b359d7dc8b3f07d61 | c1ccc(-n2cccn2)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH;D3;+0:3](-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7])-[C;H0;D3;+0:8](=O)-[C;D1;H3:9].[NH2;D1;+0:10]-[NH;D2;+0:11]-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[C:7]-[#8:6]-[C:4](=[O;D1;H0:5])-[c;H0;D3;+0:3]1:[c;H0;D3;+0:1](-[C;D1;H3:2]):[n;H0;D3;+0:11](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:... | null | [] | null | null | 8 | HOUR | p-Bromophenylhydrazine hydrochloride (10 mmol, 2.5 g) was added to 2-acetyl-3-oxo-butyric acid ethyl ester (10 mmol, 1.7 g) in ethanol (10 mL) and pyridine (10 mL). The mixture was stirred overnight at room temperature. Thin layer chromatographic (TLC) analysis using chloroform indicated the reaction was complete. The ... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Ketone | Ester | null | c1cn[nH]c1 | c1cn[nH]c1.c1ccccc1 | HO- | N1=CC=CC=C1.C(C)O | null | 8 | CCOC(=O)C(C(C)=O)C(C)=O.NNc1ccc(Br)cc1>N1=CC=CC=C1.C(C)O>CCOC(=O)c1c(C)nn(-c2ccc(Br)cc2)c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-429914abd99c47c1b147ebf79f741665 | CCOC(=O)C(C(C)=O)C(C)=O.NNc1cccc([N+](=O)[O-])c1>>CCOC(=O)c1c(C)nn(-c2cccc([N+](=O)[O-])c2)c1C | Cl.[N+](=O)([O-])C=1C=C(C=CC1)NN.C(C)OC(C(C(C)=O)C(C)=O)=O.N1=CC=CC=C1>>C(C)OC(=O)C=1C(=NN(C1C)C1=CC(=CC=C1)[N+](=O)[O-])C | O=[C:7]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:20](=O)[CH3:21])[CH3:8].[NH2:9][NH:10][c:11]1[cH:12][cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[n:9][n:10](-[c:11]2[cH:12][cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19]2)[c:20]1[CH3:21] | CCOC(=O)C(C(C)=O)C(C)=O.NNc1cccc([N+](=O)[O-])c1 | CCOC(=O)c1c(C)nn(-c2cccc([N+](=O)[O-])c2)c1C | null | null | C(C)O | Aromatic Heterocycle Formation | Pyrazole formation | ab164a2f07e9367856bf3c71fa902c37bbb79de5ea024b32fa79526bb18dc4d6 | 7abcc9a477ed734c13c96188d72c44fdd5cc90ff2d36e50b359d7dc8b3f07d61 | c1ccc(-n2cccn2)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH;D3;+0:3](-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7])-[C;H0;D3;+0:8](=O)-[C;D1;H3:9].[NH2;D1;+0:10]-[NH;D2;+0:11]-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[C:7]-[#8:6]-[C:4](=[O;D1;H0:5])-[c;H0;D3;+0:3]1:[c;H0;D3;+0:1](-[C;D1;H3:2]):[n;H0;D3;+0:11](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:... | null | [] | null | null | null | null | Similar to Example 1, m-nitrophenylhydrazine hydrochloride (10 mmol, 1.9 g) and 2-acetyl-3-oxo-butyric acid ethyl ester (10 mmol, 1.7 g) were mixed in a 50% solution of pyridine in ethanol. A precipitate was formed in the reaction medium, and was collected by filtration. Analysis confirmed synthesis of the named produc... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Ketone | Ester | null | c1cn[nH]c1 | c1cn[nH]c1.c1ccccc1 | HO- | C(C)O | null | null | CCOC(=O)C(C(C)=O)C(C)=O.NNc1cccc([N+](=O)[O-])c1>C(C)O>CCOC(=O)c1c(C)nn(-c2cccc([N+](=O)[O-])c2)c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-32740fb7cd88475c80964fc430e15578 | CCOC(=O)C(C(C)=O)C(C)=O.NNc1ccccc1>>CCOC(=O)c1c(C)nn(-c2ccccc2)c1C | C1(=CC=CC=C1)NN.C(C)OC(C(C(C)=O)C(C)=O)=O.N1=CC=CC=C1>>C(C)OC(=O)C=1C(=NN(C1C)C1=CC=CC=C1)C | O=[C:7]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:17](=O)[CH3:18])[CH3:8].[NH2:9][NH:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[n:9][n:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]1[CH3:18] | CCOC(=O)C(C(C)=O)C(C)=O.NNc1ccccc1 | CCOC(=O)c1c(C)nn(-c2ccccc2)c1C | null | null | C(C)O | Aromatic Heterocycle Formation | Pyrazole formation | ab164a2f07e9367856bf3c71fa902c37bbb79de5ea024b32fa79526bb18dc4d6 | 7abcc9a477ed734c13c96188d72c44fdd5cc90ff2d36e50b359d7dc8b3f07d61 | c1ccc(-n2cccn2)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH;D3;+0:3](-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7])-[C;H0;D3;+0:8](=O)-[C;D1;H3:9].[NH2;D1;+0:10]-[NH;D2;+0:11]-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[C:7]-[#8:6]-[C:4](=[O;D1;H0:5])-[c;H0;D3;+0:3]1:[c;H0;D3;+0:1](-[C;D1;H3:2]):[n;H0;D3;+0:11](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:... | null | [] | null | null | null | null | Similar to Example 1, phenyl hydrazine (7.5 mmol, 0.8 g) and 2-acetyl-3-oxo-butyric acid ethyl ester (7.5 mmol, 1.3 g) were mixed in a solution of 50% pyridine in ethanol. The solvents were removed under vacuum and the oil resuspended in chloroform. The resulting suspension was washed with 5% sodium bicarbonate, 5% hyd... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Ketone | Ester | null | c1cn[nH]c1 | c1cn[nH]c1.c1ccccc1 | HO- | C(C)O | null | null | CCOC(=O)C(C(C)=O)C(C)=O.NNc1ccccc1>C(C)O>CCOC(=O)c1c(C)nn(-c2ccccc2)c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8a2a370daa1e478a88c3bf3e9f78a9ca | CCOC(=O)C(C(C)=O)C(C)=O.Cc1ccc(NN)cc1>>CCOC(=O)c1c(C)nn(-c2ccc(C)cc2)c1C | C1(=CC=C(C=C1)NN)C.C(C)OC(C(C(C)=O)C(C)=O)=O.N1=CC=CC=C1>>C(C)OC(=O)C=1C(=NN(C1C)C1=CC=C(C=C1)C)C | O=[C:7]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:18](=O)[CH3:19])[CH3:8].[NH2:9][NH:10][c:11]1[cH:12][cH:13][c:14]([CH3:15])[cH:16][cH:17]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[n:9][n:10](-[c:11]2[cH:12][cH:13][c:14]([CH3:15])[cH:16][cH:17]2)[c:18]1[CH3:19] | CCOC(=O)C(C(C)=O)C(C)=O.Cc1ccc(NN)cc1 | CCOC(=O)c1c(C)nn(-c2ccc(C)cc2)c1C | null | null | C(C)O | Aromatic Heterocycle Formation | Pyrazole formation | ab164a2f07e9367856bf3c71fa902c37bbb79de5ea024b32fa79526bb18dc4d6 | 7abcc9a477ed734c13c96188d72c44fdd5cc90ff2d36e50b359d7dc8b3f07d61 | c1ccc(-n2cccn2)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH;D3;+0:3](-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7])-[C;H0;D3;+0:8](=O)-[C;D1;H3:9].[NH2;D1;+0:10]-[NH;D2;+0:11]-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[C:7]-[#8:6]-[C:4](=[O;D1;H0:5])-[c;H0;D3;+0:3]1:[c;H0;D3;+0:1](-[C;D1;H3:2]):[n;H0;D3;+0:11](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:... | null | [] | null | null | null | null | Similar to Example 1, p-tolylhydrazine (10 mmol, 1.8 g) and 2-acetyl-3-oxo-butyric acid ethyl ester (10 mmol, 1.7 g) were mixed in a solution of 50% pyridine in ethanol. The solvents were removed under vacuum. The named product was purified over silica gel (m.p. 47° C.–49° C.).
Conditions: See reaction.notes.procedure_... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Ketone | Ester | null | c1cn[nH]c1 | c1cn[nH]c1.c1ccccc1 | HO- | C(C)O | null | null | CCOC(=O)C(C(C)=O)C(C)=O.Cc1ccc(NN)cc1>C(C)O>CCOC(=O)c1c(C)nn(-c2ccc(C)cc2)c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ca83e3a45b8246e188eadb65c21b8275 | CCOC(=O)C(C(C)=O)C(C)=O.NNc1ccccc1[N+](=O)[O-]>>CCOC(=O)c1c(C)nn(-c2ccccc2[N+](=O)[O-])c1C | [N+](=O)([O-])C1=C(C=CC=C1)NN.C(C)OC(C(C(C)=O)C(C)=O)=O.N1=CC=CC=C1>>C(C)OC(=O)C=1C(=NN(C1C)C1=C(C=CC=C1)[N+](=O)[O-])C | O=[C:7]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:20](=O)[CH3:21])[CH3:8].[NH2:9][NH:10][c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[N+:17](=[O:18])[O-:19]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[n:9][n:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[N+:17](=[O:18])[O-:19])[c:20]1[CH3:21] | CCOC(=O)C(C(C)=O)C(C)=O.NNc1ccccc1[N+](=O)[O-] | CCOC(=O)c1c(C)nn(-c2ccccc2[N+](=O)[O-])c1C | null | null | C(Cl)(Cl)Cl.CCCCCC.C(C)O | Aromatic Heterocycle Formation | Pyrazole formation | ab164a2f07e9367856bf3c71fa902c37bbb79de5ea024b32fa79526bb18dc4d6 | 7abcc9a477ed734c13c96188d72c44fdd5cc90ff2d36e50b359d7dc8b3f07d61 | c1ccc(-n2cccn2)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH;D3;+0:3](-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7])-[C;H0;D3;+0:8](=O)-[C;D1;H3:9].[#7;+:10]-[c:11](:[c:12]):[c;H0;D3;+0:13](-[NH;D2;+0:14]-[NH2;D1;+0:15]):[c:16]:[c:17]>>[#7;+:10]-[c:11](:[c:12]):[c;H0;D3;+0:13](-[n;H0;D3;+0:14]1:[n;H0;D2;+0:15]:[c;H0;D3;+0:8](-[C;D1;H3:9]):[c;H0;D3;+0:3](-[... | null | [] | null | null | null | null | Similar to Example 1, o-nitrophenylhydrazine (20 mmol, 3.4 g) and 2-acetyl-3-oxo-butyric acid ethyl ester (20 mmol, 3.4 g) were mixed in a solution of 50% pyridine in ethanol and heated under reflux. The solvents then were removed under vacuum, and the residue was resuspended in chloroform. The resulting mixture was wa... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Ketone | Ester | null | c1cn[nH]c1 | c1cn[nH]c1.c1ccccc1 | HO- | C(Cl)(Cl)Cl.CCCCCC.C(C)O | null | null | CCOC(=O)C(C(C)=O)C(C)=O.NNc1ccccc1[N+](=O)[O-]>C(Cl)(Cl)Cl.CCCCCC.C(C)O>CCOC(=O)c1c(C)nn(-c2ccccc2[N+](=O)[O-])c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ed62a267b1e1458b8a6848506377f05d | CCOC(=O)c1c(C)nn(-c2ccccc2[N+](=O)[O-])c1C>>CCOC(=O)c1c(C)nn(-c2ccccc2N)c1C | C(C)OC(=O)C=1C(=NN(C1C)C1=C(C=CC=C1)[N+](=O)[O-])C.C(C)O.[H][H]>>C(C)OC(=O)C=1C(=NN(C1C)C1=C(C=CC=C1)N)C | O=[N+:17]([O-])[c:16]1[c:11](-[n:10]2[n:9][c:7]([CH3:8])[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:18]2[CH3:19])[cH:12][cH:13][cH:14][cH:15]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[n:9][n:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[NH2:17])[c:18]1[CH3:19] | CCOC(=O)c1c(C)nn(-c2ccccc2[N+](=O)[O-])c1C | CCOC(=O)c1c(C)nn(-c2ccccc2N)c1C | null | [Pd] | C(C)(=O)OCC | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(-n2cccn2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | To a solution of 3,5-dimethyl-1-(2-nitrophenyl)-1H-pyrazole-4-carboxylic acid ethyl ester (0.4 g) in a solution of equal proportions of ethanol and ethyl acetate was added 5% Pd/C (37 mg). The solution was treated with hydrogen gas at 45 psi. Upon completion of the reaction, the mixture was filtered through Celite, the... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1cn[nH]c1.c1ccccc1 | Other | [Pd].C(C)(=O)OCC | null | null | CCOC(=O)c1c(C)nn(-c2ccccc2[N+](=O)[O-])c1C>[Pd].C(C)(=O)OCC>CCOC(=O)c1c(C)nn(-c2ccccc2N)c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d66dcc09bc84436bab5835d34320f478 | CCOC(=O)C(C(C)=O)C(C)=O.NNc1ccccn1>>CCOC(=O)c1c(C)nn(-c2ccccn2)c1C | N1=C(C=CC=C1)NN.C(C)OC(C(C(C)=O)C(C)=O)=O.N1=CC=CC=C1>>C(C)OC(=O)C=1C(=NN(C1C)C1=NC=CC=C1)C | O=[C:7]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:17](=O)[CH3:18])[CH3:8].[NH2:9][NH:10][c:11]1[cH:12][cH:13][cH:14][cH:15][n:16]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[n:9][n:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][n:16]2)[c:17]1[CH3:18] | CCOC(=O)C(C(C)=O)C(C)=O.NNc1ccccn1 | CCOC(=O)c1c(C)nn(-c2ccccn2)c1C | null | null | C(C)O | Aromatic Heterocycle Formation | Pyrazole formation | ab164a2f07e9367856bf3c71fa902c37bbb79de5ea024b32fa79526bb18dc4d6 | 7abcc9a477ed734c13c96188d72c44fdd5cc90ff2d36e50b359d7dc8b3f07d61 | c1ccc(-n2cccn2)nc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH;D3;+0:3](-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7])-[C;H0;D3;+0:8](=O)-[C;D1;H3:9].[NH2;D1;+0:10]-[NH;D2;+0:11]-[c;H0;D3;+0:12](:[#7;a:13]:[c:14]):[c:15]:[c:16]>>[C:7]-[#8:6]-[C:4](=[O;D1;H0:5])-[c;H0;D3;+0:3]1:[c;H0;D3;+0:1](-[C;D1;H3:2]):[n;H0;D3;+0:11](-[c;H0;D3;+0:12](:[#7;a:13]:[c:14]):[... | null | [] | null | null | null | null | Similar to Example 1, 2-pyridylhydrazine (7.5 mmol, 0.8 g) and 2-acetyl-3-oxo-butyric acid ethyl ester (7.5 mmol, 1.3 g) were mixed in a solution of 50% pyridine in ethanol, then heated under reflux. The solvents were removed under vacuum and the residue purified over silica. The named product crystallized upon standin... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Ketone | Ester | null | c1cn[nH]c1 | c1cn[nH]c1.c1ccncc1 | HO- | C(C)O | null | null | CCOC(=O)C(C(C)=O)C(C)=O.NNc1ccccn1>C(C)O>CCOC(=O)c1c(C)nn(-c2ccccn2)c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7fc1f7aaa5b34943a693ad3861040cc8 | CCOC(=O)c1c(C)nn(-c2cccc([N+](=O)[O-])c2)c1C>>CCOC(=O)c1c(C)nn(-c2cccc(N)c2)c1C | C(C)OC(=O)C=1C(=NN(C1C)C1=CC(=CC=C1)[N+](=O)[O-])C.[H][H]>>C(C)OC(=O)C=1C(=NN(C1C)C1=CC(=CC=C1)N)C | O=[N+:16]([O-])[c:15]1[cH:14][cH:13][cH:12][c:11](-[n:10]2[n:9][c:7]([CH3:8])[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:18]2[CH3:19])[cH:17]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[n:9][n:10](-[c:11]2[cH:12][cH:13][cH:14][c:15]([NH2:16])[cH:17]2)[c:18]1[CH3:19] | CCOC(=O)c1c(C)nn(-c2cccc([N+](=O)[O-])c2)c1C | CCOC(=O)c1c(C)nn(-c2cccc(N)c2)c1C | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(-n2cccn2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | The compound of Example 2 (1.8 g) was dissolved in ethanol then 0.2 g 5% Pd/C was added to the solution. The mixture was treated with hydrogen gas at 45 psi. Upon completion of the reaction, the solution was filtered through Celite, and the filtrate concentrated under vacuum. The named product slowly crystallized upon ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1cn[nH]c1.c1ccccc1 | Other | [Pd].C(C)O | null | null | CCOC(=O)c1c(C)nn(-c2cccc([N+](=O)[O-])c2)c1C>[Pd].C(C)O>CCOC(=O)c1c(C)nn(-c2cccc(N)c2)c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3dfffe55f58b4bbcb2b5d2ddd09a9a2a | CCOC(=O)C(C(C)=O)C(C)=O.NNc1ccc([N+](=O)[O-])cn1>>CCOC(=O)c1c(C)nn(-c2ccc([N+](=O)[O-])cn2)c1C | [N+](=O)([O-])C=1C=CC(=NC1)NN.C(C)OC(C(C(C)=O)C(C)=O)=O.N1=CC=CC=C1>>C(C)OC(=O)C=1C(=NN(C1C)C1=NC=C(C=C1)[N+](=O)[O-])C | O=[C:7]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:20](=O)[CH3:21])[CH3:8].[NH2:9][NH:10][c:11]1[cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][n:19]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[n:9][n:10](-[c:11]2[cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][n:19]2)[c:20]1[CH3:21] | CCOC(=O)C(C(C)=O)C(C)=O.NNc1ccc([N+](=O)[O-])cn1 | CCOC(=O)c1c(C)nn(-c2ccc([N+](=O)[O-])cn2)c1C | null | null | C(C)O | Aromatic Heterocycle Formation | Pyrazole formation | ab164a2f07e9367856bf3c71fa902c37bbb79de5ea024b32fa79526bb18dc4d6 | 7abcc9a477ed734c13c96188d72c44fdd5cc90ff2d36e50b359d7dc8b3f07d61 | c1ccc(-n2cccn2)nc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH;D3;+0:3](-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7])-[C;H0;D3;+0:8](=O)-[C;D1;H3:9].[NH2;D1;+0:10]-[NH;D2;+0:11]-[c;H0;D3;+0:12](:[#7;a:13]:[c:14]):[c:15]:[c:16]>>[C:7]-[#8:6]-[C:4](=[O;D1;H0:5])-[c;H0;D3;+0:3]1:[c;H0;D3;+0:1](-[C;D1;H3:2]):[n;H0;D3;+0:11](-[c;H0;D3;+0:12](:[#7;a:13]:[c:14]):[... | null | [] | null | null | null | null | Similar to Example 1, equimolar amounts of (5-nitropyridin-2-yl)hydrazine and 2-acetyl-3-oxo-butyric acid ethyl ester were combined in a solution of 50% pyridine in ethanol. Analysis confirmed synthesis of the named product (m.p. 117° C.–119° C.).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Ketone | Ester | null | c1cn[nH]c1 | c1cn[nH]c1.c1ccncc1 | HO- | C(C)O | null | null | CCOC(=O)C(C(C)=O)C(C)=O.NNc1ccc([N+](=O)[O-])cn1>C(C)O>CCOC(=O)c1c(C)nn(-c2ccc([N+](=O)[O-])cn2)c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-41bda36bf6214c4a9b8efca6708532c2 | CCOC(=O)C(C(C)=O)C(C)=O.NNC1CCCCC1>>CCOC(=O)c1c(C)nn(C2CCCCC2)c1C | Cl.C1(CCCCC1)NN.C(C)OC(C(C(C)=O)C(C)=O)=O.N1=CC=CC=C1>>C(C)OC(=O)C=1C(=NN(C1C)C1CCCCC1)C | O=[C:7]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:17](=O)[CH3:18])[CH3:8].[NH2:9][NH:10][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[n:9][n:10]([CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2)[c:17]1[CH3:18] | CCOC(=O)C(C(C)=O)C(C)=O.NNC1CCCCC1 | CCOC(=O)c1c(C)nn(C2CCCCC2)c1C | null | null | C(C)O | Aromatic Heterocycle Formation | Pyrazole formation | ab164a2f07e9367856bf3c71fa902c37bbb79de5ea024b32fa79526bb18dc4d6 | 7abcc9a477ed734c13c96188d72c44fdd5cc90ff2d36e50b359d7dc8b3f07d61 | c1cnn(C2CCCCC2)c1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH;D3;+0:3](-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7])-[C;H0;D3;+0:8](=O)-[C;D1;H3:9].[C:10]-[C:11](-[NH;D2;+0:12]-[NH2;D1;+0:13])-[C:14]>>[C:10]-[C:11](-[n;H0;D3;+0:12]1:[n;H0;D2;+0:13]:[c;H0;D3;+0:8](-[C;D1;H3:9]):[c;H0;D3;+0:3](-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7]):[c;H0;D3;+0:1]:1-[C;D1;H3:2])-... | null | [] | null | null | null | null | Similar to Example 1, equimolar amounts of cyclohexyl hydrazine hydrochloride and 2-acetyl-3-oxobutyric acid ethyl ester were combined in a solution of 50% pyridine in ethanol. Analysis confirmed synthesis of the named product (m.p. 66° C.–67° C.).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Ketone | Ester | null | c1cn[nH]c1 | c1cn[nH]c1.C1CCCCC1 | HO- | C(C)O | null | null | CCOC(=O)C(C(C)=O)C(C)=O.NNC1CCCCC1>C(C)O>CCOC(=O)c1c(C)nn(C2CCCCC2)c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cdce1d85350340c0aefc14ad614d2d49 | CCOC(=O)C(C(C)=O)C(C)=O.NNCc1ccccc1>>CCOC(=O)c1c(C)nn(Cc2ccccc2)c1C | Cl.Cl.C(C1=CC=CC=C1)NN.N1=CC=CC=C1.C(C)OC(C(C(C)=O)C(C)=O)=O>>C(C)OC(=O)C=1C(=NN(C1C)CC1=CC=CC=C1)C | O=[C:7]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:18](=O)[CH3:19])[CH3:8].[NH2:9][NH:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[n:9][n:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]1[CH3:19] | CCOC(=O)C(C(C)=O)C(C)=O.NNCc1ccccc1 | CCOC(=O)c1c(C)nn(Cc2ccccc2)c1C | null | null | C(C)O | Aromatic Heterocycle Formation | Pyrazole formation | ab164a2f07e9367856bf3c71fa902c37bbb79de5ea024b32fa79526bb18dc4d6 | 7abcc9a477ed734c13c96188d72c44fdd5cc90ff2d36e50b359d7dc8b3f07d61 | c1ccc(Cn2cccn2)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH;D3;+0:3](-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7])-[C;H0;D3;+0:8](=O)-[C;D1;H3:9].[NH2;D1;+0:10]-[NH;D2;+0:11]-[C:12]-[c:13]>>[C:7]-[#8:6]-[C:4](=[O;D1;H0:5])-[c;H0;D3;+0:3]1:[c;H0;D3;+0:1](-[C;D1;H3:2]):[n;H0;D3;+0:11](-[C:12]-[c:13]):[n;H0;D2;+0:10]:[c;H0;D3;+0:8]:1-[C;D1;H3:9] | null | [] | null | null | null | null | Similar to Example 1, equimolar amounts of benzylhydrazine dihydrochloride and 2-acetyl-3-oxo-butyric acid ethyl ester were combined in a solution of 50% pyridine in ethanol. The resulting oil was determined to be the named product by 1H-NMR (CDCl3, ppm): 1.35 t (3H); 2.44 s (3H); 2.45 s (3H); 4.38 a (2H); 5.25 s (2H);... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Ketone | Ester | null | c1cn[nH]c1 | c1cn[nH]c1.c1ccccc1 | HO- | C(C)O | null | null | CCOC(=O)C(C(C)=O)C(C)=O.NNCc1ccccc1>C(C)O>CCOC(=O)c1c(C)nn(Cc2ccccc2)c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c9ce789e8e2a4048869aacc55103453f | CCOC(=O)C(C(C)=O)C(C)=O.NNc1cccc(Cl)c1>>CCOC(=O)c1c(C)nn(-c2cccc(Cl)c2)c1C | Cl.ClC=1C=C(C=CC1)NN.C(C)OC(C(C(C)=O)C(C)=O)=O.N1=CC=CC=C1>>C(C)OC(=O)C=1C(=NN(C1C)C1=CC(=CC=C1)Cl)C | O=[C:7]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:18](=O)[CH3:19])[CH3:8].[NH2:9][NH:10][c:11]1[cH:12][cH:13][cH:14][c:15]([Cl:16])[cH:17]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[n:9][n:10](-[c:11]2[cH:12][cH:13][cH:14][c:15]([Cl:16])[cH:17]2)[c:18]1[CH3:19] | CCOC(=O)C(C(C)=O)C(C)=O.NNc1cccc(Cl)c1 | CCOC(=O)c1c(C)nn(-c2cccc(Cl)c2)c1C | null | null | C(C)O | Aromatic Heterocycle Formation | Pyrazole formation | ab164a2f07e9367856bf3c71fa902c37bbb79de5ea024b32fa79526bb18dc4d6 | 7abcc9a477ed734c13c96188d72c44fdd5cc90ff2d36e50b359d7dc8b3f07d61 | c1ccc(-n2cccn2)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH;D3;+0:3](-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7])-[C;H0;D3;+0:8](=O)-[C;D1;H3:9].[NH2;D1;+0:10]-[NH;D2;+0:11]-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[C:7]-[#8:6]-[C:4](=[O;D1;H0:5])-[c;H0;D3;+0:3]1:[c;H0;D3;+0:1](-[C;D1;H3:2]):[n;H0;D3;+0:11](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:... | null | [] | null | null | null | null | Similar to Example 1, equimolar amounts of 3-chlorophenylhydrazine hydrochloride and 2-acetyl-3-oxo-butyric acid ethyl ester were combined in a solution of 50% pyridine in ethanol. Analysis confirmed that the resulting solid was determined to be the named product (m.p. 56° C.–57° C.).
Conditions: See reaction.notes.pro... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Ketone | Ester | null | c1cn[nH]c1 | c1cn[nH]c1.c1ccccc1 | HO- | C(C)O | null | null | CCOC(=O)C(C(C)=O)C(C)=O.NNc1cccc(Cl)c1>C(C)O>CCOC(=O)c1c(C)nn(-c2cccc(Cl)c2)c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-10ff9f3ebf424ef1bf07a369dc0fa429 | CCOC(=O)C(C(C)=O)C(C)=O.Cc1cccc(NN)c1>>CCOC(=O)c1c(C)nn(-c2cccc(C)c2)c1C | Cl.C1(=CC(=CC=C1)NN)C.C(C)OC(C(C(C)=O)C(C)=O)=O.N1=CC=CC=C1>>C(C)OC(=O)C=1C(=NN(C1C)C=1C=C(C=CC1)C)C | O=[C:7]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:18](=O)[CH3:19])[CH3:8].[NH2:9][NH:10][c:11]1[cH:12][cH:13][cH:14][c:15]([CH3:16])[cH:17]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[n:9][n:10](-[c:11]2[cH:12][cH:13][cH:14][c:15]([CH3:16])[cH:17]2)[c:18]1[CH3:19] | CCOC(=O)C(C(C)=O)C(C)=O.Cc1cccc(NN)c1 | CCOC(=O)c1c(C)nn(-c2cccc(C)c2)c1C | null | null | C(C)O | Aromatic Heterocycle Formation | Pyrazole formation | ab164a2f07e9367856bf3c71fa902c37bbb79de5ea024b32fa79526bb18dc4d6 | 7abcc9a477ed734c13c96188d72c44fdd5cc90ff2d36e50b359d7dc8b3f07d61 | c1ccc(-n2cccn2)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH;D3;+0:3](-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7])-[C;H0;D3;+0:8](=O)-[C;D1;H3:9].[NH2;D1;+0:10]-[NH;D2;+0:11]-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[C:7]-[#8:6]-[C:4](=[O;D1;H0:5])-[c;H0;D3;+0:3]1:[c;H0;D3;+0:1](-[C;D1;H3:2]):[n;H0;D3;+0:11](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:... | null | [] | null | null | null | null | Similar to Example 1, equimolar amounts of m-tolylhydrazine hydrochloride and 2-acetyl-3-oxo-butyric acid ethyl ester were combined in a solution of a 50% pyridine in ethanol. The resulting oil was purified by flash chromatography to yield the named product as a solid (m.p. 46.5° C.–47.5° C.).
Conditions: See reaction.... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Ketone | Ester | null | c1cn[nH]c1 | c1cn[nH]c1.c1ccccc1 | HO- | C(C)O | null | null | CCOC(=O)C(C(C)=O)C(C)=O.Cc1cccc(NN)c1>C(C)O>CCOC(=O)c1c(C)nn(-c2cccc(C)c2)c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-50a50e2c29a64a198360ea13b9febfaf | CCOC(=O)C(C(C)=O)C(C)=O.NNc1cccc(F)c1>>CCOC(=O)c1c(C)nn(-c2cccc(F)c2)c1C | Cl.FC=1C=C(C=CC1)NN.C(C)OC(C(C(C)=O)C(C)=O)=O.N1=CC=CC=C1>>C(C)OC(=O)C=1C(=NN(C1C)C1=CC(=CC=C1)F)C | O=[C:7]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:18](=O)[CH3:19])[CH3:8].[NH2:9][NH:10][c:11]1[cH:12][cH:13][cH:14][c:15]([F:16])[cH:17]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[n:9][n:10](-[c:11]2[cH:12][cH:13][cH:14][c:15]([F:16])[cH:17]2)[c:18]1[CH3:19] | CCOC(=O)C(C(C)=O)C(C)=O.NNc1cccc(F)c1 | CCOC(=O)c1c(C)nn(-c2cccc(F)c2)c1C | null | null | C(C)O | Aromatic Heterocycle Formation | Pyrazole formation | ab164a2f07e9367856bf3c71fa902c37bbb79de5ea024b32fa79526bb18dc4d6 | 7abcc9a477ed734c13c96188d72c44fdd5cc90ff2d36e50b359d7dc8b3f07d61 | c1ccc(-n2cccn2)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH;D3;+0:3](-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7])-[C;H0;D3;+0:8](=O)-[C;D1;H3:9].[NH2;D1;+0:10]-[NH;D2;+0:11]-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[C:7]-[#8:6]-[C:4](=[O;D1;H0:5])-[c;H0;D3;+0:3]1:[c;H0;D3;+0:1](-[C;D1;H3:2]):[n;H0;D3;+0:11](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:... | null | [] | null | null | null | null | Similar to Example 1, equimolar amounts of 3-fluorophenylhydrazine hydrochloride and 2-acetyl-3-oxo-butyric acid ethyl ester were combined in a solution of 50% pyridine in ethanol. Analysis showed that resulting solid was the named product (m.p. 55° C.–56.1° C.).
Conditions: See reaction.notes.procedure_details.
Workup... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Ketone | Ester | null | c1cn[nH]c1 | c1cn[nH]c1.c1ccccc1 | HO- | C(C)O | null | null | CCOC(=O)C(C(C)=O)C(C)=O.NNc1cccc(F)c1>C(C)O>CCOC(=O)c1c(C)nn(-c2cccc(F)c2)c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6d47505205454e4dbf465abd74ce19e3 | CCOC(=O)C(C(C)=O)C(C)=O.COc1cccc(NN)c1>>CCOC(=O)c1c(C)nn(-c2cccc(OC)c2)c1C | Cl.COC=1C=C(C=CC1)NN.C(C)OC(C(C(C)=O)C(C)=O)=O.N1=CC=CC=C1>>C(C)OC(=O)C=1C(=NN(C1C)C1=CC(=CC=C1)OC)C | O=[C:7]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:19](=O)[CH3:20])[CH3:8].[NH2:9][NH:10][c:11]1[cH:12][cH:13][cH:14][c:15]([O:16][CH3:17])[cH:18]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[n:9][n:10](-[c:11]2[cH:12][cH:13][cH:14][c:15]([O:16][CH3:17])[cH:18]2)[c:19]1[CH3:20] | CCOC(=O)C(C(C)=O)C(C)=O.COc1cccc(NN)c1 | CCOC(=O)c1c(C)nn(-c2cccc(OC)c2)c1C | null | null | C(C)O | Aromatic Heterocycle Formation | Pyrazole formation | ab164a2f07e9367856bf3c71fa902c37bbb79de5ea024b32fa79526bb18dc4d6 | 7abcc9a477ed734c13c96188d72c44fdd5cc90ff2d36e50b359d7dc8b3f07d61 | c1ccc(-n2cccn2)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH;D3;+0:3](-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7])-[C;H0;D3;+0:8](=O)-[C;D1;H3:9].[NH2;D1;+0:10]-[NH;D2;+0:11]-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[C:7]-[#8:6]-[C:4](=[O;D1;H0:5])-[c;H0;D3;+0:3]1:[c;H0;D3;+0:1](-[C;D1;H3:2]):[n;H0;D3;+0:11](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:... | null | [] | null | null | null | null | Similar to Example 1, equimolar amounts of 3-methoxyphenylhydrazine hydrochloride and 2-acetyl-3-oxo-butyric acid ethyl ester were combined in a solution of 50% pyridine in ethanol. The resulting solid was determined to be the named product by 1H-NMR (CDCl3, ppm): 1.38 t (3H); 2.50 s (3H); 2.52 s (3H); 3.84 s (3H); 4.3... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Ketone | Ester | null | c1cn[nH]c1 | c1cn[nH]c1.c1ccccc1 | HO- | C(C)O | null | null | CCOC(=O)C(C(C)=O)C(C)=O.COc1cccc(NN)c1>C(C)O>CCOC(=O)c1c(C)nn(-c2cccc(OC)c2)c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-96e1a28570e240d998aab5642757c5ed | CCOC(=O)C(C(C)=O)C(C)=O.NNc1cccc(Br)c1>>CCOC(=O)c1c(C)nn(-c2cccc(Br)c2)c1C | Cl.BrC=1C=C(C=CC1)NN.C(C)OC(C(C(C)=O)C(C)=O)=O.N1=CC=CC=C1>>C(C)OC(=O)C=1C(=NN(C1C)C1=CC(=CC=C1)Br)C | O=[C:7]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:18](=O)[CH3:19])[CH3:8].[NH2:9][NH:10][c:11]1[cH:12][cH:13][cH:14][c:15]([Br:16])[cH:17]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[n:9][n:10](-[c:11]2[cH:12][cH:13][cH:14][c:15]([Br:16])[cH:17]2)[c:18]1[CH3:19] | CCOC(=O)C(C(C)=O)C(C)=O.NNc1cccc(Br)c1 | CCOC(=O)c1c(C)nn(-c2cccc(Br)c2)c1C | null | null | C(C)O | Aromatic Heterocycle Formation | Pyrazole formation | ab164a2f07e9367856bf3c71fa902c37bbb79de5ea024b32fa79526bb18dc4d6 | 7abcc9a477ed734c13c96188d72c44fdd5cc90ff2d36e50b359d7dc8b3f07d61 | c1ccc(-n2cccn2)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH;D3;+0:3](-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7])-[C;H0;D3;+0:8](=O)-[C;D1;H3:9].[NH2;D1;+0:10]-[NH;D2;+0:11]-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[C:7]-[#8:6]-[C:4](=[O;D1;H0:5])-[c;H0;D3;+0:3]1:[c;H0;D3;+0:1](-[C;D1;H3:2]):[n;H0;D3;+0:11](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:... | null | [] | null | null | null | null | Similar to Example 1, equimolar amounts of 3-bromophenylhydrazine hydrochloride and 2-acetyl-3-oxo-butyric acid ethyl ester were combined in a solution of 50% pyridine in ethanol. Analysis showed that the resulting solid was the named product (m.p. 34° C.–35° C.).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Ketone | Ester | null | c1cn[nH]c1 | c1cn[nH]c1.c1ccccc1 | HO- | C(C)O | null | null | CCOC(=O)C(C(C)=O)C(C)=O.NNc1cccc(Br)c1>C(C)O>CCOC(=O)c1c(C)nn(-c2cccc(Br)c2)c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d784be3dc1194f6b9ccfbea658a1aa5c | CCOC(=O)C(C=O)C(C)=O.NNc1ccccn1>>CCOC(=O)c1cn(-c2ccccn2)nc1C | N1=C(C=CC=C1)NN.C(C)OC(C(C(C)=O)C=O)=O.N1=CC=CC=C1>>C(C)OC(=O)C=1C(=NN(C1)C1=NC=CC=C1)C | O=[CH:7][CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:16](=O)[CH3:17].[NH:8]([c:9]1[cH:10][cH:11][cH:12][cH:13][n:14]1)[NH2:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8](-[c:9]2[cH:10][cH:11][cH:12][cH:13][n:14]2)[n:15][c:16]1[CH3:17] | CCOC(=O)C(C=O)C(C)=O.NNc1ccccn1 | CCOC(=O)c1cn(-c2ccccn2)nc1C | null | null | C(C)O | Aromatic Heterocycle Formation | Pyrazole formation | d602667e63297ba975a48166d1a7540bdf0e5f502b4608ff23c3d35dbd14c749 | 78679c7da938d0abe886998033bf74c7e120b260d850498336b36cb336ed2e65 | c1ccc(-n2cccn2)nc1 | O=[CH;D2;+0:1]-[CH;D3;+0:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6])-[C;H0;D3;+0:7](=O)-[C;D1;H3:8].[NH2;D1;+0:9]-[NH;D2;+0:10]-[c;H0;D3;+0:11](:[#7;a:12]:[c:13]):[c:14]:[c:15]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[c;H0;D3;+0:2]1:[cH;D2;+0:1]:[n;H0;D3;+0:10](-[c;H0;D3;+0:11](:[#7;a:12]:[c:13]):[c:14]:[c:15]):[n;H0;D2;+0:9]:[c;H... | null | [] | null | null | null | null | Similar to Example 1, equimolar amounts of 2-pyridylhydrazine and 2-formyl-3-oxo-butyric acid ethyl ester were combined in a solution of 50% pyridine in ethanol. Analysis showed that the resulting solid was determined to be the named product (m.p. 49° C.–50° C.).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Aldehyde.Ketone | Ester | null | c1cn[nH]c1 | c1cn[nH]c1.c1ccncc1 | HO- | C(C)O | null | null | CCOC(=O)C(C=O)C(C)=O.NNc1ccccn1>C(C)O>CCOC(=O)c1cn(-c2ccccn2)nc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-96385c6264c1424398d9348e12f7a5f7 | CCOC(=O)c1cnn(-c2ccc([N+](=O)[O-])cc2)c1C(F)(F)F>>CCOC(=O)c1cnn(-c2ccc(N)cc2)c1C(F)(F)F | C(=O)[O-].[NH4+].C(C)OC(=O)C=1C=NN(C1C(F)(F)F)C1=CC=C(C=C1)[N+](=O)[O-]>>C(C)OC(=O)C=1C=NN(C1C(F)(F)F)C1=CC=C(C=C1)N | O=[N+:14]([O-])[c:13]1[cH:12][cH:11][c:10](-[n:9]2[n:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:17]2[C:18]([F:19])([F:20])[F:21])[cH:16][cH:15]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][n:9](-[c:10]2[cH:11][cH:12][c:13]([NH2:14])[cH:15][cH:16]2)[c:17]1[C:18]([F:19])([F:20])[F:21] | CCOC(=O)c1cnn(-c2ccc([N+](=O)[O-])cc2)c1C(F)(F)F | CCOC(=O)c1cnn(-c2ccc(N)cc2)c1C(F)(F)F | null | [Pd] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(-n2cccn2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 8 | HOUR | To 1-(4-nitrophenyl)-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid ethyl ester (0.5 g, 1.5 mmol) dissolved in methanol (4 mL) was added palladium on carbon and ammonium formate (0.428 g, 6.8 mmol). This mixture was stirred at room temperature overnight. The solvent was removed under vacuum, then the material was resu... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1cn[nH]c1.c1ccccc1 | Other | [Pd].CO | null | 8 | CCOC(=O)c1cnn(-c2ccc([N+](=O)[O-])cc2)c1C(F)(F)F>[Pd].CO>CCOC(=O)c1cnn(-c2ccc(N)cc2)c1C(F)(F)F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8959462339fc4fa39d40a4aaa8d1a18d | O=C(O)C1=CC2C=CC1CC2>>O=C(O)C1=CC2CCC1CC2 | C12C(=CC(C=C1)CC2)C(=O)O>>C12C(=CC(CC1)CC2)C(=O)O | [O:1]=[C:2]([OH:3])[C:4]1=[CH:5][CH:6]2[CH:7]=[CH:8][CH:9]1[CH2:10][CH2:11]2>>[O:1]=[C:2]([OH:3])[C:4]1=[CH:5][CH:6]2[CH2:7][CH2:8][CH:9]1[CH2:10][CH2:11]2 | O=C(O)C1=CC2C=CC1CC2 | O=C(O)C1=CC2CCC1CC2 | null | [Pd] | CCOC(=O)C | Reduction | Hydrogenation (double to single) | 308380a5c356db5a7568d32bb5139ef654b83c4655b064956b8b4edc3eb3e8f6 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | C1=CC2CCC1CC2 | [O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[C:4]1=[C:5]-[C:6]2-[C:7]-[C:8]-[C:9]-1-[CH;D2;+0:10]=[CH;D2;+0:11]-2>>[O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[C:4]1=[C:5]-[C:6]2-[C:7]-[C:8]-[C:9]-1-[CH2;D2;+0:10]-[CH2;D2;+0:11]-2 | 98.8 | [{"value": 98.8, "product": "C12C(=CC(CC1)CC2)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | Compound 11A (600 mg, 3.99 mmol) was dissolved in EtOAc (5 mL), 5% Pd/C (12 mg) was added and the mixture was stirred under a hydrogen balloon for 1.5 h. The reaction mixture was filtered through a pad of celite and concentrated under reduced pressure to give 600 mg of compound 11B as a yellow oil. No further purificat... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1=CC2C=CC1CC2 | C1=CC2CCC1CC2 | C1=CC2CCC1CC2 | null | [Pd].CCOC(=O)C | null | 1.5 | O=C(O)C1=CC2C=CC1CC2>[Pd].CCOC(=O)C>O=C(O)C1=CC2CCC1CC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1909c0ad6b5f4b5bb7d6bc3e0ee986fa | O=C(Cl)C(=O)Cl.O=C(O)C1=CC2CCC1CC2>>O=C(Cl)C1=CC2CCC1CC2 | C(C(=O)Cl)(=O)Cl.C12C(=CC(CC1)CC2)C(=O)O>>C12C(=CC(CC1)CC2)C(=O)Cl | O=C(Cl)C(=O)[Cl:3].O[C:2](=[O:1])[C:4]1=[CH:5][CH:6]2[CH2:7][CH2:8][CH:9]1[CH2:10][CH2:11]2>>[O:1]=[C:2]([Cl:3])[C:4]1=[CH:5][CH:6]2[CH2:7][CH2:8][CH:9]1[CH2:10][CH2:11]2 | O=C(Cl)C(=O)Cl.O=C(O)C1=CC2CCC1CC2 | O=C(Cl)C1=CC2CCC1CC2 | null | CN(C)C=O | C(Cl)Cl | Functional Group Interconversion | Alcohol to chloride_Other | 013cec2edeb273a7a148f349d36a52d99ff4e7bcf8eed78085df830088e387ac | aedb1f68dc5b7eb0583043e1125b741382b17974140a2f46554f0110e2ddc884 | C1=CC2CCC1CC2 | Cl-C(=O)-C(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4](=[C:5]-[C:6])-[C:7]>>[C:6]-[C:5]=[C:4](-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3])-[C:7] | 100.9 | [{"value": 100.9, "product": "C12C(=CC(CC1)CC2)C(=O)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | Oxalyl chloride (2.0 M in CH2Cl2, 2.4 mL, 4.8 mmol, 1.2 eq) was added to a solution of compound 11B (600 mg, 3.95 mmol, 1 eq) in CH2Cl2 (8 mL) containing one drop of DMF. The reaction mixture was stirred at rt for 3 h and then concentrated under reduced pressure to give 680 mg of compound 11C which was used in the next... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Carboxylic acid | Acyl halide | null | null | C1=CC2CCC1CC2 | HCl | CN(C)C=O.C(Cl)Cl | null | 3 | O=C(Cl)C(=O)Cl.O=C(O)C1=CC2CCC1CC2>CN(C)C=O.C(Cl)Cl>O=C(Cl)C1=CC2CCC1CC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2975d623528d4c1983bcf37f33b4b1fc | O=C(Nc1ccc([N+](=O)[O-])c(C(F)(F)F)c1)C1=CC2CCC1CC2.O=C(OO)c1cccc(Cl)c1>>O=C(Nc1ccc([N+](=O)[O-])c(C(F)(F)F)c1)C12OC1C1CCC2CC1 | C1=CC(=CC(=C1)Cl)C(=O)OO.[N+](=O)([O-])C1=C(C=C(C=C1)NC(=O)C=1C2CCC(C1)CC2)C(F)(F)F>>[N+](=O)([O-])C1=C(C=C(C=C1)NC(=O)C12C3CCC(C2O1)CC3)C(F)(F)F | [O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[c:11]([C:12]([F:13])([F:14])[F:15])[cH:16]1)[C:17]1=[CH:19][CH:20]2[CH2:21][CH2:22][CH:23]1[CH2:24][CH2:25]2.O=C(O[OH:18])c1cccc(Cl)c1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[c:11]([C:12]([F:13])([F:14])[F:15])[cH:16]1)[C:17]12[O... | O=C(Nc1ccc([N+](=O)[O-])c(C(F)(F)F)c1)C1=CC2CCC1CC2.O=C(OO)c1cccc(Cl)c1 | O=C(Nc1ccc([N+](=O)[O-])c(C(F)(F)F)c1)C12OC1C1CCC2CC1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | f79c34ec388f8df9b9b89ea9de8ecf1ebca4e0f74834a7853952a206f5ce3380 | c40ffbbc3249442e5ee39aaa69a55be7ac2fa45f48637395e415c565c1288454 | O=C(Nc1ccccc1)C12OC1C1CCC2CC1 | Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c:1.[O;D1;H0:2]=[C:3](-[#7:4]-[c:5])-[C;H0;D3;+0:6]1=[CH;D2;+0:7]-[C:8]2-[C:9]-[C:10]-[C:11]-1-[C:12]-[C:13]-2>>[O;D1;H0:2]=[C:3](-[#7:4]-[c:5])-[C;H0;D4;+0:6]12-[O;H0;D2;+0:1]-[CH;D3;+0:7]-1-[C:8]1-[C:9]-[C:10]-[C:11]-2-[C:12]-[C:13]-1 | 58 | [{"value": 57.6, "product": "[N+](=O)([O-])C1=C(C=C(C=C1)NC(=O)C12C3CCC(C2O1)CC3)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.0, "product": "[N+](=O)([O-])C1=C(C=C(C=C1)NC(=O)C12C3CCC(C2O1)CC3)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | mCPBA (60% mixture, 518 mg, 3.00 mmol, 3 eq) was added to a solution of 11D (340 mg, 1.0 mmol, 1.0 eq) in CH2Cl2 (20 mL). The reaction mixture was stirred at rt overnight and then diluted with CH2Cl2 (40 mL). The organic solution was washed with sat. NaHCO3 (1×50 mL), brine (1×50 mL), dried over Na2SO4 and concentrated... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide | Ether | c1ccccc1.C1=CC2CCC1CC2 | C1CC2CCC1C1OC21 | c1ccccc1.C1CC2CCC1C1OC21 | HCl | C(Cl)Cl | null | 8 | O=C(Nc1ccc([N+](=O)[O-])c(C(F)(F)F)c1)C1=CC2CCC1CC2.O=C(OO)c1cccc(Cl)c1>C(Cl)Cl>O=C(Nc1ccc([N+](=O)[O-])c(C(F)(F)F)c1)C12OC1C1CCC2CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-73f63908c360412b9540f8f878a26354 | O=C(Nc1ccc([N+](=O)[O-])c(C(F)(F)F)c1)C12OC1C1CCC2CC1.O=P(NO)(c1ccccc1)c1ccccc1>>NN(C(=O)C12OC1C1CCC2CC1)c1ccc([N+](=O)[O-])c(C(F)(F)F)c1 | [H-].[Na+].[N+](=O)([O-])C1=C(C=C(C=C1)NC(=O)C12C3CCC(C2O1)CC3)C(F)(F)F.C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)NO>>[N+](=O)([O-])C1=C(C=C(C=C1)N(N)C(=O)C12C3CCC(C2O1)CC3)C(F)(F)F | [NH:2]([C:3](=[O:4])[C:5]12[O:6][CH:7]1[CH:8]1[CH2:9][CH2:10][CH:11]2[CH2:12][CH2:13]1)[c:14]1[cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[c:21]([C:22]([F:23])([F:24])[F:25])[cH:26]1.O=P(c1ccccc1)(c1ccccc1)[NH:1]O>>[NH2:1][N:2]([C:3](=[O:4])[C:5]12[O:6][CH:7]1[CH:8]1[CH2:9][CH2:10][CH:11]2[CH2:12][CH2:13]1)[c:14]1[cH:... | O=C(Nc1ccc([N+](=O)[O-])c(C(F)(F)F)c1)C12OC1C1CCC2CC1.O=P(NO)(c1ccccc1)c1ccccc1 | NN(C(=O)C12OC1C1CCC2CC1)c1ccc([N+](=O)[O-])c(C(F)(F)F)c1 | null | null | CN(C)C=O | Functional Group Addition | OtherReaction | 5e05c0c1badc0df2b2150021b18144ee06fc93c19e1707faf0e51ad8dc4ffc92 | 4b0afe5ae720bad786941c3ee7b748fcbfe464a74354723b418c604097cbd660 | O=C(Nc1ccccc1)C12OC1C1CCC2CC1 | O-[NH;D2;+0:1]-P(=O)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.[#8:2]-[C:3]-[C:4](=[O;D1;H0:5])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[#8:2]-[C:3]-[C:4](=[O;D1;H0:5])-[N;H0;D3;+0:6](-[NH2;D1;+0:1])-[c:7](:[c:8]):[c:9] | 15.4 | [{"value": 15.4, "product": "[N+](=O)([O-])C1=C(C=C(C=C1)N(N)C(=O)C12C3CCC(C2O1)CC3)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 8 | HOUR | NaH (60% in mineral oil, 7.9 mg, 0.20 mmol, 1.4 eq) was added to the solution of 11E (50 mg, 0.14 mmol, 1 eq) in DMF (3 mL). The reaction mixture was heated at 70° C. for 2 h. The reaction was cooled to rt and diphenylphosphinylhydroxylamine (52 mg, 0.22 mmol, 1.6 eq, made according to the procedure of Colvin, E. W. et... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Secondary amine | Acylhydrazine | c1ccccc1.c1ccccc1 | null | c1ccccc1.C1CC2CCC1C1OC21 | HO- | CN(C)C=O | 70 | 8 | O=C(Nc1ccc([N+](=O)[O-])c(C(F)(F)F)c1)C12OC1C1CCC2CC1.O=P(NO)(c1ccccc1)c1ccccc1>CN(C)C=O>NN(C(=O)C12OC1C1CCC2CC1)c1ccc([N+](=O)[O-])c(C(F)(F)F)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f742f3db871b4af2af5afa3faa6671a2 | COC(=O)C(=O)OC.CSc1ccc(C(C)=O)cc1>>COC(=O)/C(O)=C/C(=O)c1ccc(SC)cc1 | COC(C(=O)OC)=O.C[O-].[Na+].Cl.CSC1=CC=C(C=C1)C(C)=O>>O\C(\C(=O)OC)=C/C(=O)C1=CC=C(C=C1)SC | CO[C:5]([C:3]([O:2][CH3:1])=[O:4])=[O:6].[CH3:7][C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13]([S:14][CH3:15])[cH:16][cH:17]1>>[CH3:1][O:2][C:3](=[O:4])/[C:5]([OH:6])=[CH:7]/[C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13]([S:14][CH3:15])[cH:16][cH:17]1 | COC(=O)C(=O)OC.CSc1ccc(C(C)=O)cc1 | COC(=O)/C(O)=C/C(=O)c1ccc(SC)cc1 | null | null | CCOC(=O)C.CCCCCC.C(Cl)Cl.C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | e4a4589a9c43a9e3e18aebd6481c6bd15819939729f59fb85b833b2a820f9d8c | 551bf13e9bbf5f86c83696b5ff28a85752492e6b0d2510ee489f6a83816bb6d9 | c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6].[CH3;D1;+0:7]-[C:8](=[O;D1;H0:9])-[c:10]>>[C;D1;H3:6]-[#8:5]-[C:3](=[O;D1;H0:4])/[C;H0;D3;+0:1](-[OH;D1;+0:2])=[CH;D2;+0:7]/[C:8](=[O;D1;H0:9])-[c:10] | 79 | [{"value": 79.0, "product": "O\\C(\\C(=O)OC)=C/C(=O)C1=CC=C(C=C1)SC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.9, "product": "O\\C(\\C(=O)OC)=C/C(=O)C1=CC=C(C=C1)SC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 15 | MINUTE | Dimethyloxalate (26 g, 180.7 mmol) was added to a stirred suspension of sodium methoxide (9.75 g, 180.7 mmol) in dry toluene (200 mL) at 0° C. The white suspension was stirred for 15 min at 0° C. A solution of 4′-(methylthio)acetophenone (15 g, 90.4 mmol) in dry toluene (150 mL) was then added drop-wise over 15 minutes... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Ester | Ketone.Ester.Enol | null | null | c1ccccc1 | HO- | CCOC(=O)C.CCCCCC.C(Cl)Cl.C1(=CC=CC=C1)C | 0 | 0.25 | COC(=O)C(=O)OC.CSc1ccc(C(C)=O)cc1>CCOC(=O)C.CCCCCC.C(Cl)Cl.C1(=CC=CC=C1)C>COC(=O)/C(O)=C/C(=O)c1ccc(SC)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d315ddcc6d8d4f5e8190cb9892565d27 | CC(=O)c1ccc(C)cc1.COC(=O)C(=O)OC>>COC(=O)C(=O)CC(=O)c1ccc(C)cc1 | COC(C(=O)OC)=O.CC1=CC=C(C=C1)C(C)=O>>CC1=CC=C(C=C1)C(CC(C(=O)OC)=O)=O | [CH3:7][C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13]([CH3:14])[cH:15][cH:16]1.CO[C:5]([C:3]([O:2][CH3:1])=[O:4])=[O:6]>>[CH3:1][O:2][C:3](=[O:4])[C:5](=[O:6])[CH2:7][C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13]([CH3:14])[cH:15][cH:16]1 | CC(=O)c1ccc(C)cc1.COC(=O)C(=O)OC | COC(=O)C(=O)CC(=O)c1ccc(C)cc1 | null | null | null | C-C Coupling | OtherReaction | 75e47111412c372865b4b8c2556a24f38f2daf372ab5522938a6e976b4732185 | 907e247f98c28f5bcc369b20fadcc26c24574c2b68d4b59762f1e8515d373c02 | c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6].[CH3;D1;+0:7]-[C:8](=[O;D1;H0:9])-[c:10]>>[C;D1;H3:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:7]-[C:8](=[O;D1;H0:9])-[c:10] | 74 | [{"value": 74.0, "product": "CC1=CC=C(C=C1)C(CC(C(=O)OC)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.0, "product": "CC1=CC=C(C=C1)C(CC(C(=O)OC)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared from dimethyloxalate (47.24 g, 400 mmol) and 4′-methylacetophenone (26.84 g, 200 mmol) using the procedure for Example 1d. Work-up and recrystallization provided the title compound as white needles (32.6 g, 74% yield). Mp 82–84° C. 1H NMR (300 MHz, CDCl3) δ 15.36 (br.s, 1H), 7.92 (d, J=8... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Ester | Ketone.Ketone | null | null | c1ccccc1 | HO- | null | null | null | CC(=O)c1ccc(C)cc1.COC(=O)C(=O)OC>>COC(=O)C(=O)CC(=O)c1ccc(C)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4f84ead693da4f968cd28a52005d8455 | NN.NS(=O)(=O)c1ccc(Cl)cc1>>NNc1ccc(S(N)(=O)=O)cc1 | ClC1=CC=C(C=C1)S(=O)(=O)N.NN>>N(N)C1=CC=C(C=C1)S(=O)(=O)N | [NH2:1][NH2:2].Cl[c:3]1[cH:4][cH:5][c:6]([S:7]([NH2:8])(=[O:9])=[O:10])[cH:11][cH:12]1>>[NH2:1][NH:2][c:3]1[cH:4][cH:5][c:6]([S:7]([NH2:8])(=[O:9])=[O:10])[cH:11][cH:12]1 | NN.NS(=O)(=O)c1ccc(Cl)cc1 | NNc1ccc(S(N)(=O)=O)cc1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | d8df4273e702dfa5f61e1fc063d26292e73a06b19b988689234fbb3a4a4eddc6 | 61806bbf8bb8981e140ee503663af0ef0e69dc4f34f6582f974a2e4218f7da88 | c1ccccc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[N;D1;H2:6]-[NH2;D1;+0:7]>>[N;D1;H2:6]-[NH;D2;+0:7]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 95 | [{"value": 95.0, "product": "N(N)C1=CC=C(C=C1)S(=O)(=O)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.8, "product": "N(N)C1=CC=C(C=C1)S(=O)(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred solution of 4-chlorobenzenesulfonamide (38.33 g, 200 mmol) and anhydrous hydrazine (31.4 mL, 1.0 mol) was heated at reflux for 30 hours. After cooling to room temperature, the mixture was poured into water (500 mL) with swirling. The resulting precipitate was collected by filtration, washed thoroughly with wa... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Aromatic halide | Hydrazine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | O | null | null | NN.NS(=O)(=O)c1ccc(Cl)cc1>O>NNc1ccc(S(N)(=O)=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7a51bd60341c47f6bf110e2467dc0b37 | CC(=O)c1cccnc1.COC(=O)C(=O)OC>>COC(=O)C(=O)CC(=O)c1cccnc1 | C[O-].[Na+].COC(C(=O)OC)=O.C(C)(=O)C=1C=NC=CC1>>O=C(C(=O)OC)CC(C=1C=NC=CC1)=O | [CH3:7][C:8](=[O:9])[c:10]1[cH:11][cH:12][cH:13][n:14][cH:15]1.CO[C:5]([C:3]([O:2][CH3:1])=[O:4])=[O:6]>>[CH3:1][O:2][C:3](=[O:4])[C:5](=[O:6])[CH2:7][C:8](=[O:9])[c:10]1[cH:11][cH:12][cH:13][n:14][cH:15]1 | CC(=O)c1cccnc1.COC(=O)C(=O)OC | COC(=O)C(=O)CC(=O)c1cccnc1 | null | null | CO | C-C Coupling | OtherReaction | 75e47111412c372865b4b8c2556a24f38f2daf372ab5522938a6e976b4732185 | 907e247f98c28f5bcc369b20fadcc26c24574c2b68d4b59762f1e8515d373c02 | c1ccncc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6].[#7;a:7]:[c:8]:[c:9]-[C:10](-[CH3;D1;+0:11])=[O;D1;H0:12]>>[#7;a:7]:[c:8]:[c:9]-[C:10](=[O;D1;H0:12])-[CH2;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6] | 84 | [{"value": 84.0, "product": "O=C(C(=O)OC)CC(C=1C=NC=CC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.7, "product": "O=C(C(=O)OC)CC(C=1C=NC=CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | Sodium methoxide (5.4 g, 100 mmol) and dimethyloxalate (11.8 g, 100 mmol) were dissolved in anhydrous methanol (700 mL) and stirred at room temperature under nitrogen until a suspension was formed. To this mixture, 3-acetylpyridine (5.5 mL, 50 mmol) was added and the stirring was continued for 3 days at room temperatur... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Ester | Ketone.Ketone | null | null | c1ccncc1 | HO- | CO | null | 72 | CC(=O)c1cccnc1.COC(=O)C(=O)OC>CO>COC(=O)C(=O)CC(=O)c1cccnc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-71614f4ee7974ddbb313fb7d2c4b05c4 | BrCBr.COC(=O)c1cc(-c2ccc(SC)cc2)n(-c2ccccn2)n1>>CSc1ccc(-c2cc(C(=O)CBr)nn2-c2ccccn2)cc1 | CSC1=CC=C(C=C1)C1=CC(=NN1C1=NC=CC=C1)C(=O)OC.BrCBr.C[Li]>>BrCC(=O)C1=NN(C(=C1)C1=CC=C(C=C1)SC)C1=NC=CC=C1 | Br[CH2:12][Br:13].CO[C:10]([c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([S:2][CH3:1])[cH:23][cH:22]2)[n:15](-[c:16]2[cH:17][cH:18][cH:19][cH:20][n:21]2)[n:14]1)=[O:11]>>[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([C:10](=[O:11])[CH2:12][Br:13])[n:14][n:15]2-[c:16]2[cH:17][cH:18][cH:19][cH:20][n:21]2)[cH:22][cH... | BrCBr.COC(=O)c1cc(-c2ccc(SC)cc2)n(-c2ccccn2)n1 | CSc1ccc(-c2cc(C(=O)CBr)nn2-c2ccccn2)cc1 | null | null | C1CCOC1 | C-C Coupling | Ester and halide to ketone | ef01edc1b01f560e7b39a38bc55679d327781879123a79598fa9742cc5379d75 | 50aab8a39d4c72422e6b6f48201993c767ec539687188d0d15e6e0fb0c160b8f | c1ccc(-c2ccnn2-c2ccccn2)cc1 | Br-[CH2;D2;+0:1]-[Br;D1;H0:2].C-O-[C;H0;D3;+0:3](=[O;D1;H0:4])-[c:5]1:[#7;a:6]:[#7;a:7](-[c:8]:[#7;a:9]):[c:10]:[c:11]:1>>[#7;a:9]:[c:8]-[#7;a:7]1:[#7;a:6]:[c:5](-[C;H0;D3;+0:3](=[O;D1;H0:4])-[CH2;D2;+0:1]-[Br;D1;H0:2]):[c:11]:[c:10]:1 | 69 | [{"value": 69.0, "product": "BrCC(=O)C1=NN(C(=C1)C1=CC=C(C=C1)SC)C1=NC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.7, "product": "BrCC(=O)C1=NN(C(=C1)C1=CC=C(C=C1)SC)C1=NC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 90 | MINUTE | To a stirred solution of methyl 5-(4-methylthiophenyl)-1-(2-pyridyl)pyrazole-3-carboxylate (prepared as described in Penning, T. D. et al. J. Med. Chem. 1997, 40, 1347–1365.; 0.39 g, 1.2 mmol) and dibromomethane (0.17 mL, 2.4 mmol) in THF (10 mL) at −78° C. under nitrogen atmosphere was added methyllithium (1.6 M in et... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Ester | Primary halide.Ketone | null | null | c1ccccc1.c1cc[nH]n1.c1ccncc1 | HBr | C1CCOC1 | null | 1.5 | BrCBr.COC(=O)c1cc(-c2ccc(SC)cc2)n(-c2ccccn2)n1>C1CCOC1>CSc1ccc(-c2cc(C(=O)CBr)nn2-c2ccccn2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1855fff929db4ad5a02d92ae3b13462a | COC(=O)CCCC(=O)Cl.CSc1ccc(C(C)=O)cc1>>COC(=O)CCCC(=O)/C=C(\O)c1ccc(SC)cc1 | ClC(=O)CCCC(=O)OC.O1CCCC1.C(C)(C)[N-]C(C)C.[Li+].C1CCCCC1.CSC1=CC=C(C=C1)C(C)=O.Cl>>O\C(=C/C(CCCC(=O)OC)=O)\C1=CC=C(C=C1)SC | Cl[C:8]([CH2:7][CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])=[O:9].[CH3:10][C:11](=[O:12])[c:13]1[cH:14][cH:15][c:16]([S:17][CH3:18])[cH:19][cH:20]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][C:8](=[O:9])/[CH:10]=[C:11](\[OH:12])[c:13]1[cH:14][cH:15][c:16]([S:17][CH3:18])[cH:19][cH:20]1 | COC(=O)CCCC(=O)Cl.CSc1ccc(C(C)=O)cc1 | COC(=O)CCCC(=O)/C=C(\O)c1ccc(SC)cc1 | null | null | C1CCOC1 | Acylation | OtherReaction | 2029a9fd814fb6888f6b35c6c0956cbe0c2588ea0f802e1fcc4b8a3538ed447f | 7af1aa12c8f3746f2a06ac5e1d991bf2e77c1b8a35928ecbdd7fb025269f18f0 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[CH3;D1;+0:5]-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-[c:8](:[c:9]):[c:10]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])/[CH;D2;+0:5]=[C;H0;D3;+0:6](\[OH;D1;+0:7])-[c:8](:[c:9]):[c:10] | null | [] | -72 | CELSIUS | 30 | MINUTE | Lithium diisopropylamide mono(tetrahydrofuran) in cyclohexane (1.5 M; 28 mL, 42 mmol) was added to a solution of 1-(4-methylthiophenyl)ethan-1-one (5.16 g, 31 mmol) in THF (120 mL) and stirred for 30 minutes at −72° C. A solution of methyl 4-(chloroformyl)butyrate (1.78 g, 10.8 mmol) was added to the above solution and... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ketone | Ketone.Enol | null | null | c1ccccc1 | HCl | C1CCOC1 | -72 | 0.5 | COC(=O)CCCC(=O)Cl.CSc1ccc(C(C)=O)cc1>C1CCOC1>COC(=O)CCCC(=O)/C=C(\O)c1ccc(SC)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fd95e3c9024b41f58c60e5039c57717d | NCCCO.O=[N+]([O-])O>>NCCCO[N+](=O)[O-].O=[N+]([O-])O | NCCCO.[N+](=O)(O)[O-]>>[N+](=O)(O)[O-].[N+](=O)([O-])OCCCN | [NH2:1][CH2:2][CH2:3][CH2:4][OH:5].[OH:7][N+:10](=[O:9])[O-:11]>>[NH2:1][CH2:2][CH2:3][CH2:4][O:5][N+:6](=[O:7])[O-:8].[O:9]=[N+:10]([O-:11])[OH:12] | NCCCO.O=[N+]([O-])O | NCCCO[N+](=O)[O-].O=[N+]([O-])O | null | null | C(C)(=O)OC(C)=O | Miscellaneous | OtherReaction | 466d5d9cd6feb612ac74d087ae3a5c028119633b42075559ce0b1a6050e470bd | eebe4cdf377c5f23a15ba9981c4bf0f364574de70110a9649086825b36e97a31 | null | [C:1]-[C:2]-[OH;D1;+0:3].[O;-;D1;H0:4]-[N+;H0;D3:5](=[O;D1;H0:6])-[OH;D1;+0:7]>>[C:1]-[C:2]-[O;H0;D2;+0:3]-[#7;+:8](-[O;-;D1;H0:9])=[O;H0;D1;+0:7].[O;-;D1;H0:4]-[N+;H0;D3:5](=[O;D1;H0:6])-[O;D1;H1:10] | 80 | [{"value": 80.0, "product": "[N+](=O)(O)[O-].[N+](=O)([O-])OCCCN", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | A solution of 3-amino-1-propanol (6.17 g, 82.2 mmol) was added, dropwise, to an ice-cooled solution of fuming nitric acid (12 mL) in acetic anhydride (50 mL). The reaction was stirred in an ice-bath for 10 minutes and then at room temperature for 10 minutes. The solvent was evaporated under vacuum at 40° C. The residue... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate.Primary alcohol | Nitrate.Nitrate | null | null | null | Other | C(C)(=O)OC(C)=O | null | 0.166667 | NCCCO.O=[N+]([O-])O>C(C)(=O)OC(C)=O>NCCCO[N+](=O)[O-].O=[N+]([O-])O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5c5f16cc6c2d49e0b89c3666d774b67a | CI.COc1cccc2c1C(C)C(=O)N2>>COc1cccc2c1C(C)(C)C(=O)N2 | Cl.IC.Cl.C[Si](C)(C)[N-][Si](C)(C)C.[K+].COC1=C2C(C(NC2=CC=C1)=O)C>>COC1=C2C(C(NC2=CC=C1)=O)(C)C | I[CH3:10].[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8]1[CH:9]([CH3:11])[C:12](=[O:13])[NH:14]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8]1[C:9]([CH3:10])([CH3:11])[C:12](=[O:13])[NH:14]2 | CI.COc1cccc2c1C(C)C(=O)N2 | COc1cccc2c1C(C)(C)C(=O)N2 | null | null | CO.O1CCCC1.C1(=CC=CC=C1)C | C-C Coupling | Methylation with MeI_tertiary | 4ff962ca13d51fef8dbede7a9389c6828f46295ce155e36b5ca1c7adc5a62f3d | 410ec9b1cc243569e4ff568c248f0b402403802e002b4018f576af3f6960507b | O=C1Cc2ccccc2N1 | I-[CH3;D1;+0:1].[C;D1;H3:2]-[CH;D3;+0:3]1-[C:4](=[O;D1;H0:5])-[#7:6]-[c:7]:[c:8]-1:[c:9]>>[C;D1;H3:2]-[C;H0;D4;+0:3]1(-[CH3;D1;+0:1])-[C:4](=[O;D1;H0:5])-[#7:6]-[c:7]:[c:8]-1:[c:9] | 58 | [{"value": 58.0, "product": "COC1=C2C(C(NC2=CC=C1)=O)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.1, "product": "COC1=C2C(C(NC2=CC=C1)=O)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 1 | HOUR | A solution of 4-methoxy-3-methyl-1,3-dihydro-indol-2-one (41.73 g, 235.5 mmol) and tetrahydrofuran (1000 mL) is cooled to −78° C. Potassium bis(trimethylsilyl)amide (989.0 mL, 494.3 mmol, 0.5 M in toluene) is added over 45 minutes so as to maintain the reaction temperature between −71° C. and −66° C. Iodomethane (36.71... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | HI | CO.O1CCCC1.C1(=CC=CC=C1)C | -78 | 1 | CI.COc1cccc2c1C(C)C(=O)N2>CO.O1CCCC1.C1(=CC=CC=C1)C>COc1cccc2c1C(C)(C)C(=O)N2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6e6691a549f845a5a05326a4086fecbe | COc1cccc2c1C(C)(C)C(=O)N2>>CC1(C)C(=O)Nc2cccc(O)c21 | Cl.N1=CC=CC=C1.COC1=C2C(C(NC2=CC=C1)=O)(C)C>>OC1=C2C(C(NC2=CC=C1)=O)(C)C | C[O:12][c:11]1[cH:10][cH:9][cH:8][c:7]2[c:13]1[C:2]([CH3:1])([CH3:3])[C:4](=[O:5])[NH:6]2>>[CH3:1][C:2]1([CH3:3])[C:4](=[O:5])[NH:6][c:7]2[cH:8][cH:9][cH:10][c:11]([OH:12])[c:13]21 | COc1cccc2c1C(C)(C)C(=O)N2 | CC1(C)C(=O)Nc2cccc(O)c21 | null | null | CCCCCC | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1Cc2ccccc2N1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 68.9 | [{"value": 68.0, "product": "OC1=C2C(C(NC2=CC=C1)=O)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.9, "product": "OC1=C2C(C(NC2=CC=C1)=O)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 220 | CELSIUS | 45 | MINUTE | Pyridine hydrochloride (51.10 g, 442.2 mmol) and 4-methoxy-3,3-dimethyl-1,3-dihydro-indol-2-one (21.61 g, 113.0 mmol) are combined and stirred in a melt at 220° C. for 45 minutes. Heating is removed and when the mixture cooled to 100° C., water (60 mL) is added, followed by ethyl acetate (150 mL) at 65° C. The layers a... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccc2c(c1)CCN2 | Other | CCCCCC | 220 | 0.75 | COc1cccc2c1C(C)(C)C(=O)N2>CCCCCC>CC1(C)C(=O)Nc2cccc(O)c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e4c5726ac3974685a58e1ea2a6c0c8f7 | CC(C)[N+](=O)[O-].CN(C)Cc1c[nH]c2c(OCc3ccccc3)cccc12>>CC(C)(Cc1c[nH]c2c(OCc3ccccc3)cccc12)[N+](=O)[O-] | [N+](=O)([O-])C(C)C.CN(C)CC1=CNC2=C1C=CC=C2OCC3=CC=CC=C3.[OH-].[Na+].[N+](=O)([O-])C(C)C>>CC(CC1=CNC2=C(C=CC=C12)OCC1=CC=CC=C1)(C)[N+](=O)[O-] | [CH3:1][CH:2]([CH3:3])[N+:22](=[O:23])[O-:24].CN(C)[CH2:4][c:5]1[cH:6][nH:7][c:8]2[c:9]([O:10][CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[cH:18][cH:19][cH:20][c:21]12>>[CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][nH:7][c:8]2[c:9]([O:10][CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[cH:18][cH:19][cH:20][c:21... | CC(C)[N+](=O)[O-].CN(C)Cc1c[nH]c2c(OCc3ccccc3)cccc12 | CC(C)(Cc1c[nH]c2c(OCc3ccccc3)cccc12)[N+](=O)[O-] | null | null | CCOCC | C-C Coupling | OtherReaction | 410d0ecf550dfec32b5bd37f61aeafc75533d5e4329aa3110c08acb15e21dcaa | fc73a0ba4f6f90cb21df47612bcde105fcd2a049cd56b52924f944fc6a6cbe55 | c1ccc(COc2cccc3cc[nH]c23)cc1 | C-N(-C)-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[C;D1;H3:7]-[CH;D3;+0:8](-[C;D1;H3:9])-[#7;+:10](-[O;-;D1;H0:11])=[O;D1;H0:12]>>[C;D1;H3:7]-[C;H0;D4;+0:8](-[C;D1;H3:9])(-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:1)-[#7;+:10](-[O;-;D1;H0:11])=[O;D1;H0:12] | 92.1 | [{"value": 92.0, "product": "CC(CC1=CNC2=C(C=CC=C12)OCC1=CC=CC=C1)(C)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.1, "product": "CC(CC1=CNC2=C(C=CC=C12)OCC1=CC=CC=C1)(C)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 29 | HOUR | A mixture of 7-benzyloxy gramine (1.99 g, 7.10 mmol), solid NaOH (298 mg, 7.22 mmol) and 2-nitropropane (4.5 mL, 50 mmol) is heated to reflux. After 10 minutes at reflux, a thick slurry developed which is difficult to stir. Gas evolution is observed, and an additional 1 mL of 2-nitropropane is added to loosen the mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Tertiary amine | Nitro group | null | null | c1ccccc1.c1ccc2[nH]ccc2c1 | Other | CCOCC | null | 29 | CC(C)[N+](=O)[O-].CN(C)Cc1c[nH]c2c(OCc3ccccc3)cccc12>CCOCC>CC(C)(Cc1c[nH]c2c(OCc3ccccc3)cccc12)[N+](=O)[O-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b83aba9157f44fd9b0f7974734e9190c | CC(C)(Cc1c[nH]c2c(OCc3ccccc3)cccc12)[N+](=O)[O-]>>CC(C)(N)Cc1c[nH]c2c(OCc3ccccc3)cccc12 | CC(CC1=CNC2=C(C=CC=C12)OCC1=CC=CC=C1)(C)[N+](=O)[O-].C(C)O>>CC(CC1=CNC2=C(C=CC=C12)OCC1=CC=CC=C1)(C)N | O=[N+:4]([O-])[C:2]([CH3:1])([CH3:3])[CH2:5][c:6]1[cH:7][nH:8][c:9]2[c:10]([O:11][CH2:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[cH:19][cH:20][cH:21][c:22]12>>[CH3:1][C:2]([CH3:3])([NH2:4])[CH2:5][c:6]1[cH:7][nH:8][c:9]2[c:10]([O:11][CH2:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[cH:19][cH:20][cH:21][c:22]12 | CC(C)(Cc1c[nH]c2c(OCc3ccccc3)cccc12)[N+](=O)[O-] | CC(C)(N)Cc1c[nH]c2c(OCc3ccccc3)cccc12 | null | [Ni] | O1CCCC1 | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(COc2cccc3cc[nH]c23)cc1 | O=[N+;H0;D3:1](-[O-])-[C:2](-[C:3])(-[C;D1;H3:4])-[C;D1;H3:5]>>[C:3]-[C:2](-[C;D1;H3:4])(-[C;D1;H3:5])-[NH2;D1;+0:1] | 99 | [{"value": 99.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 1 | HOUR | A mixture of 3-(2-methyl-2-nitropropyl)-7-(benzyloxy)indole (25.0 g, 77.1 mmol), Raney Nickel® (9.5 g wet lump), and 3A ethanol (250 mL) is pressurized to 50 psig with H2 and is heated to 60° C. After 1 hour, the mixture is cooled to ambient temperature. The mixture is diluted with tetrahydrofuran (100 mL) and is warme... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccc2[nH]ccc2c1 | Other | [Ni].O1CCCC1 | 60 | 1 | CC(C)(Cc1c[nH]c2c(OCc3ccccc3)cccc12)[N+](=O)[O-]>[Ni].O1CCCC1>CC(C)(N)Cc1c[nH]c2c(OCc3ccccc3)cccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9dc9d58956fe4180abe509a7f0f59e1e | CC(C)(Cc1c[nH]c2c(OCc3ccccc3)cccc12)NC(=O)OC(C)(C)C>>CC(C)(Cc1c[nH]c2c(O)cccc12)NC(=O)OC(C)(C)C | C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)OCC1=CC=CC=C1)(C)C)=O>>C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)O)(C)C)=O | c1ccc(C[O:10][c:9]2[c:8]3[nH:7][cH:6][c:5]([CH2:4][C:2]([CH3:1])([CH3:3])[NH:15][C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[c:14]3[cH:13][cH:12][cH:11]2)cc1>>[CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][nH:7][c:8]2[c:9]([OH:10])[cH:11][cH:12][cH:13][c:14]12)[NH:15][C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21... | CC(C)(Cc1c[nH]c2c(OCc3ccccc3)cccc12)NC(=O)OC(C)(C)C | CC(C)(Cc1c[nH]c2c(O)cccc12)NC(=O)OC(C)(C)C | null | [Pd] | C(C)O | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc2[nH]ccc2c1 | [c:1]:[c:2](-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4](:[c:5]):[#7;a:6]:[c:7]>>[OH;D1;+0:3]-[c:2](:[c:1]):[c:4](:[c:5]):[#7;a:6]:[c:7] | 96.2 | [{"value": 96.0, "product": "C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)O)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.2, "product": "C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)O)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 40 | MINUTE | A mixture of [2-(7-benzyloxy-1H-indol-3-yl)-1,1-dimethyl-ethyl]-carbamic acid tert-butyl ester (20.75 g, 52.6 mmol), 5% Pd/C (1.00 g, 5 wt %), and 3A ethanol (200 mL) is pressurized to 55 psig with H2, and is heated to 50° C. After 40 minutes, the slurry is filtered, and the filtrate is concentrated to give 15.41 g of ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccc2[nH]ccc2c1 | Other | [Pd].C(C)O | 50 | 0.666667 | CC(C)(Cc1c[nH]c2c(OCc3ccccc3)cccc12)NC(=O)OC(C)(C)C>[Pd].C(C)O>CC(C)(Cc1c[nH]c2c(O)cccc12)NC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-32cf1dfce18849a1889085ab34daa5ed | CC(C)(Cc1c[nH]c2c(OS(=O)(=O)C(F)(F)F)cccc12)NC(=O)OC(C)(C)C.NC(=O)c1ccc(Br)cc1>>CC(C)(Cc1c[nH]c2c(-c3ccc(C(N)=O)cc3)cccc12)NC(=O)OC(C)(C)C | BrC1=CC=C(C(=O)N)C=C1.B1(OC(C(O1)(C)C)(C)C)B2OC(C(O2)(C)C)(C)C.C(C)(=O)[O-].[K+].C(C)(C)(C)OC(=O)NC(CC1=CNC2=C(C=CC=C12)OS(=O)(=O)C(F)(F)F)(C)C.C([O-])([O-])=O.[Na+].[Na+]>>C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)C1=CC=C(C=C1)C(N)=O)(C)C)=O | O=S(=O)(O[c:9]1[c:8]2[nH:7][cH:6][c:5]([CH2:4][C:2]([CH3:1])([CH3:3])[NH:23][C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30])[c:22]2[cH:21][cH:20][cH:19]1)C(F)(F)F.Br[c:10]1[cH:11][cH:12][c:13]([C:14]([NH2:15])=[O:16])[cH:17][cH:18]1>>[CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][nH:7][c:8]2[c:9](-[c:10]3[cH:11][cH:... | CC(C)(Cc1c[nH]c2c(OS(=O)(=O)C(F)(F)F)cccc12)NC(=O)OC(C)(C)C.NC(=O)c1ccc(Br)cc1 | CC(C)(Cc1c[nH]c2c(-c3ccc(C(N)=O)cc3)cccc12)NC(=O)OC(C)(C)C | null | null | C(C)(=O)OCC.CS(=O)C.[Cl-].[Na+].O | C-C Coupling | OtherReaction | 1b2df86b67777cac54c7612bb407c72c2c13320e3c623fa8dcc9aa27a39bb9ba | 6fa0c5f5a567aef7a3c8790e894c3eacfb3f5a56b34ccd5ba5e56676973c2603 | c1ccc(-c2cccc3cc[nH]c23)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](:[c:10]):[#7;a:11]:[c:12]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](:[c:10]):[#7;a:11]:[c:12]):[c:4]:[c:5] | 58.5 | [{"value": 58.0, "product": "C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)C1=CC=C(C=C1)C(N)=O)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.5, "product": "C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)C1=CC=C(C=C1)C(N)=O)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | null | null | A solution of 4-bromobenzamide (150 mg, 0.75 mmol), bis(pinacolato)diboron (209 mg, 0.825 mmol), potassium acetate (0.221 g, 2.25 mmol) and {1,1′-bis(diphenylphosphino)-ferrocene}dichloropalladium dichloromethane complex (18 mg, 0.0225 mmol) in dimethylsulfoxide (5 mL) is heated to 80° C. for two hours. The mixture is ... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Aromatic halide | null | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccccc1.c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | TfOH.Br- | C(C)(=O)OCC.CS(=O)C.[Cl-].[Na+].O | 20 | null | CC(C)(Cc1c[nH]c2c(OS(=O)(=O)C(F)(F)F)cccc12)NC(=O)OC(C)(C)C.NC(=O)c1ccc(Br)cc1>C(C)(=O)OCC.CS(=O)C.[Cl-].[Na+].O>CC(C)(Cc1c[nH]c2c(-c3ccc(C(N)=O)cc3)cccc12)NC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1bf2a222fc824b4c96663fff97db984b | CC(C)(Cc1c[nH]c2c(OS(=O)(=O)C(F)(F)F)cccc12)NC(=O)OC(C)(C)C.OB(O)c1ccc(C(F)(F)F)cc1>>CC(C)(Cc1c[nH]c2c(-c3ccc(C(F)(F)F)cc3)cccc12)NC(=O)OC(C)(C)C | C(C)(C)(C)OC(=O)NC(CC1=CNC2=C(C=CC=C12)OS(=O)(=O)C(F)(F)F)(C)C.C([O-])([O-])=O.[Na+].[Na+].FC(C1=CC=C(C=C1)B(O)O)(F)F>>C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)C1=CC=C(C=C1)C(F)(F)F)(C)C)=O | O=S(=O)(O[c:9]1[c:8]2[nH:7][cH:6][c:5]([CH2:4][C:2]([CH3:1])([CH3:3])[NH:24][C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[c:23]2[cH:22][cH:21][cH:20]1)C(F)(F)F.OB(O)[c:10]1[cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][cH:19]1>>[CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][nH:7][c:8]2[c:9](-[c:10]3[cH... | CC(C)(Cc1c[nH]c2c(OS(=O)(=O)C(F)(F)F)cccc12)NC(=O)OC(C)(C)C.OB(O)c1ccc(C(F)(F)F)cc1 | CC(C)(Cc1c[nH]c2c(-c3ccc(C(F)(F)F)cc3)cccc12)NC(=O)OC(C)(C)C | 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 | O1CCCC1.[Cl-].[Na+].O | C-C Coupling | Suzuki coupling with boronic acids OTf | e5b06a5a12e240e2c1d187f11833a1f8be82588ba5052d6ae155510c885c9487 | 3f602cf53fbcf2a56d992979503f6bea55727095a6b9075475a711784170b440 | c1ccc(-c2cccc3cc[nH]c23)cc1 | F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7].O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[c:10]:[c:9]:[c;H0;D3;+0:8](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]):[c:11]:[c:12] | 93.3 | [{"value": 93.0, "product": "C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)C1=CC=C(C=C1)C(F)(F)F)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.3, "product": "C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)C1=CC=C(C=C1)C(F)(F)F)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of trifluoro-methanesulfonic acid 3-(2-tert-butoxycarbonylamino-2-methyl-propyl)-1H-indol-7-yl ester (305 mg, 0.699 mmol) in tetrahydrofuran (4.5 mL) is added sodium carbonate (1 mL, 2M, 2 mmol), tetrakis(triphenylphosphine)-palladium (32 mg, 0.0280 mmol) and 4-trifluoromethylbenzeneboronic acid (0.1 99 g... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Boronic acid | null | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccccc1.c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | TfOH.HO-.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.O1CCCC1.[Cl-].[Na+].O | null | null | CC(C)(Cc1c[nH]c2c(OS(=O)(=O)C(F)(F)F)cccc12)NC(=O)OC(C)(C)C.OB(O)c1ccc(C(F)(F)F)cc1>[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.O1CCCC1.[Cl-].[Na+].O>CC(C)(Cc1c[nH]c2c(-c3ccc(C(F)(F)F)cc3)cccc12)NC(=O)OC... |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-61c1e1a0aa5e442d91a796b5a4f41109 | CC(C)(Cc1c[nH]c2c(OS(=O)(=O)C(F)(F)F)cccc12)NC(=O)OC(C)(C)C.OB(O)c1ccsc1>>CC(C)(Cc1c[nH]c2c(-c3ccsc3)cccc12)NC(=O)OC(C)(C)C | C(C)(C)(C)OC(=O)NC(CC1=CNC2=C(C=CC=C12)OS(=O)(=O)C(F)(F)F)(C)C.C(C)N(CC)CC.S1C=C(C=C1)B(O)O>>C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)C1=CSC=C1)(C)C)=O | O=S(=O)(O[c:9]1[c:8]2[nH:7][cH:6][c:5]([CH2:4][C:2]([CH3:1])([CH3:3])[NH:19][C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[c:18]2[cH:17][cH:16][cH:15]1)C(F)(F)F.OB(O)[c:10]1[cH:11][cH:12][s:13][cH:14]1>>[CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][nH:7][c:8]2[c:9](-[c:10]3[cH:11][cH:12][s:13][cH:14]3)[cH:15][cH:... | CC(C)(Cc1c[nH]c2c(OS(=O)(=O)C(F)(F)F)cccc12)NC(=O)OC(C)(C)C.OB(O)c1ccsc1 | CC(C)(Cc1c[nH]c2c(-c3ccsc3)cccc12)NC(=O)OC(C)(C)C | 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.CN(C=O)C.[Cl-].[Na+].O | C-C Coupling | Suzuki coupling with boronic acids OTf | a7850579aaea4f63726c5ab350ab1102424a87584a5eae5768d335f9a6e0784b | 3f602cf53fbcf2a56d992979503f6bea55727095a6b9075475a711784170b440 | c1cc(-c2ccsc2)c2[nH]ccc2c1 | F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7].O-B(-O)-[c;H0;D3;+0:8]1:[c:9]:[c:10]:[#16;a:11]:[c:12]:1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8]1:[c:9]:[c:10]:[#16;a:11]:[c:12]:1):[c:4](:[c:5]):[#7;a:6]:[c:7] | 69 | [{"value": 69.0, "product": "C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)C1=CSC=C1)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.6, "product": "C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)C1=CSC=C1)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of trifluoro-methanesulfonic acid 3-(2-tert-butoxycarbonylamino-2-methyl-propyl)-1H-indol-7-yl ester (340 mg, 0.779 mmol) in dimethylformamide (5 mL) is added triethylamine (0.14 mL, 1.01 mmol), tetrakis(triphenylphosphine)-palladium (36 mg, 0.0312 mmol) and 3-thiopheneboronic acid (130 mg, 1.01 mmol). Th... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Boronic acid | null | c1ccc2[nH]ccc2c1.c1ccsc1 | c1ccsc1.c1ccc2[nH]ccc2c1 | c1ccsc1.c1ccc2[nH]ccc2c1 | TfOH.HO-.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.CN(C=O)C.[Cl-].[Na+].O | null | null | CC(C)(Cc1c[nH]c2c(OS(=O)(=O)C(F)(F)F)cccc12)NC(=O)OC(C)(C)C.OB(O)c1ccsc1>[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.CN(C=O)C.[Cl-].[Na+].O>CC(C)(Cc1c[nH]c2c(-c3ccsc3)cccc12)NC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0732badd337946498b912644452a820b | CC(C)(Cc1c[nH]c2c(OS(=O)(=O)C(F)(F)F)cccc12)NC(=O)OC(C)(C)C.OB(O)c1cccs1>>CC(C)(Cc1c[nH]c2c(-c3cccs3)cccc12)NC(=O)OC(C)(C)C | C(C)(C)(C)OC(=O)NC(CC1=CNC2=C(C=CC=C12)OS(=O)(=O)C(F)(F)F)(C)C.C(C)N(CC)CC.S1C(=CC=C1)B(O)O>>C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)C=1SC=CC1)(C)C)=O | O=S(=O)(O[c:9]1[c:8]2[nH:7][cH:6][c:5]([CH2:4][C:2]([CH3:1])([CH3:3])[NH:19][C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[c:18]2[cH:17][cH:16][cH:15]1)C(F)(F)F.OB(O)[c:10]1[cH:11][cH:12][cH:13][s:14]1>>[CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][nH:7][c:8]2[c:9](-[c:10]3[cH:11][cH:12][cH:13][s:14]3)[cH:15][cH:... | CC(C)(Cc1c[nH]c2c(OS(=O)(=O)C(F)(F)F)cccc12)NC(=O)OC(C)(C)C.OB(O)c1cccs1 | CC(C)(Cc1c[nH]c2c(-c3cccs3)cccc12)NC(=O)OC(C)(C)C | 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.CN(C=O)C.[Cl-].[Na+].O | C-C Coupling | Suzuki coupling with boronic acids OTf | a7850579aaea4f63726c5ab350ab1102424a87584a5eae5768d335f9a6e0784b | 3f602cf53fbcf2a56d992979503f6bea55727095a6b9075475a711784170b440 | c1csc(-c2cccc3cc[nH]c23)c1 | F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7].O-B(-O)-[c;H0;D3;+0:8]1:[#16;a:9]:[c:10]:[c:11]:[c:12]:1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8]1:[#16;a:9]:[c:10]:[c:11]:[c:12]:1):[c:4](:[c:5]):[#7;a:6]:[c:7] | 31.3 | [{"value": 31.0, "product": "C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)C=1SC=CC1)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 31.3, "product": "C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)C=1SC=CC1)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of trifluoro-methanesulfonic acid 3-(2-tert-butoxycarbonylamino-2-methyl-propyl)-1H-indol-7-yl ester (437 mg, 1.00 mmol) in dimethylformamide (6 mL) is added triethylamine (0.18 mL, 1.30 mmol), tetrakis(triphenylphosphine)-palladium (46 mg, 0.0401 mmol) and 2-thiopheneboronic acid (167 mg, 1.30 mmol). The... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Boronic acid | null | c1ccc2[nH]ccc2c1.c1ccsc1 | c1ccsc1.c1ccc2[nH]ccc2c1 | c1ccsc1.c1ccc2[nH]ccc2c1 | TfOH.HO-.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.CN(C=O)C.[Cl-].[Na+].O | null | null | CC(C)(Cc1c[nH]c2c(OS(=O)(=O)C(F)(F)F)cccc12)NC(=O)OC(C)(C)C.OB(O)c1cccs1>[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.CN(C=O)C.[Cl-].[Na+].O>CC(C)(Cc1c[nH]c2c(-c3cccs3)cccc12)NC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-343aac3f52b94d84a607d6578897d0f3 | CC(C)(Cc1c[nH]c2c(OS(=O)(=O)C(F)(F)F)cccc12)NC(=O)OC(C)(C)C.OB(O)c1ccc(C(F)(F)F)cc1C(F)(F)F>>CC(C)(Cc1c[nH]c2c(-c3ccc(C(F)(F)F)cc3C(F)(F)F)cccc12)NC(=O)OC(C)(C)C | C(C)(C)(C)OC(=O)NC(CC1=CNC2=C(C=CC=C12)OS(=O)(=O)C(F)(F)F)(C)C.C(C)N(CC)CC.FC(C1=C(C=CC(=C1)C(F)(F)F)B(O)O)(F)F>>C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)C1=C(C=C(C=C1)C(F)(F)F)C(F)(F)F)(C)C)=O | O=S(=O)(O[c:9]1[c:8]2[nH:7][cH:6][c:5]([CH2:4][C:2]([CH3:1])([CH3:3])[NH:28][C:29](=[O:30])[O:31][C:32]([CH3:33])([CH3:34])[CH3:35])[c:27]2[cH:26][cH:25][cH:24]1)C(F)(F)F.OB(O)[c:10]1[cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][c:19]1[C:20]([F:21])([F:22])[F:23]>>[CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][n... | CC(C)(Cc1c[nH]c2c(OS(=O)(=O)C(F)(F)F)cccc12)NC(=O)OC(C)(C)C.OB(O)c1ccc(C(F)(F)F)cc1C(F)(F)F | CC(C)(Cc1c[nH]c2c(-c3ccc(C(F)(F)F)cc3C(F)(F)F)cccc12)NC(=O)OC(C)(C)C | 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.CN(C=O)C.[Cl-].[Na+].O | C-C Coupling | Suzuki coupling with boronic acids OTf | e5b06a5a12e240e2c1d187f11833a1f8be82588ba5052d6ae155510c885c9487 | 3f602cf53fbcf2a56d992979503f6bea55727095a6b9075475a711784170b440 | c1ccc(-c2cccc3cc[nH]c23)cc1 | F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7].O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11](-[C:12](-[F;D1;H0:13])(-[F;D1;H0:14])-[F;D1;H0:15]):[c:16]>>[F;D1;H0:13]-[C:12](-[F;D1;H0:14])(-[F;D1;H0:15])-[c:11](:[c:16]):[c;H0;D3;+0:8](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]... | 89.2 | [{"value": 89.0, "product": "C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)C1=C(C=C(C=C1)C(F)(F)F)C(F)(F)F)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.2, "product": "C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)C1=C(C=C(C=C1)C(F)(F)F)C(F)(F)F)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | To a solution of trifluoro-methanesulfonic acid 3-(2-tert-butoxycarbonylamino-2-methyl-propyl)-1H-indol-7-yl ester (262 mg, 0.600 mmol) in dimethylformamide (3.5 mL) is added triethylamine (0.11 mL, 0.780 mmol), tetrakis(triphenylphosphine)-palladium (28 mg, 0.0240 mmol) and 2,4-bistrifluoromethylbenzeneboronic acid (2... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Boronic acid | null | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccccc1.c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | TfOH.HO-.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.CN(C=O)C.[Cl-].[Na+].O | 100 | null | CC(C)(Cc1c[nH]c2c(OS(=O)(=O)C(F)(F)F)cccc12)NC(=O)OC(C)(C)C.OB(O)c1ccc(C(F)(F)F)cc1C(F)(F)F>[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.CN(C=O)C.[Cl-].[Na+].O>CC(C)(Cc1c[nH]c2c(-c3ccc(C(F)(F)... |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-30b6def8a1514691b9d38b1893394da3 | CC(C)(Cc1c[nH]c2c(O)cccc12)NC(=O)OC(C)(C)C.N#CCBr>>CC(C)(Cc1c[nH]c2c(OCC#N)cccc12)NC(=O)OC(C)(C)C | C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)O)(C)C)=O.BrCC#N.C(=O)([O-])[O-].[K+].[K+]>>C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)OCC#N)(C)C)=O | [CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][nH:7][c:8]2[c:9]([OH:10])[cH:14][cH:15][cH:16][c:17]12)[NH:18][C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25].Br[CH2:11][C:12]#[N:13]>>[CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][nH:7][c:8]2[c:9]([O:10][CH2:11][C:12]#[N:13])[cH:14][cH:15][cH:16][c:17]12)[NH:18][C:19](=[O:... | CC(C)(Cc1c[nH]c2c(O)cccc12)NC(=O)OC(C)(C)C.N#CCBr | CC(C)(Cc1c[nH]c2c(OCC#N)cccc12)NC(=O)OC(C)(C)C | null | null | CC(CC)=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc2[nH]ccc2c1 | Br-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7](:[c:8]):[#7;a:9]:[c:10]>>[N;D1;H0:3]#[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7](:[c:8]):[#7;a:9]:[c:10] | 86.5 | [{"value": 86.0, "product": "C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)OCC#N)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.5, "product": "C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)OCC#N)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A mixture of [2-(7-hydroxy-1H-indol-3-yl)-1,1-dimethyl-ethyl]-carbamic acid tert-butyl ester (15.55 g, 51.1 mmol), bromoacetonitrile (10.7 mL, 153 mmol), K2CO3 (17.78 g, 128.6 mmol) and 2-butanone is heated to reflux. After 1 hour the mixture is allowed to cool and is filtered through celite. The filtrate is concentrat... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2[nH]ccc2c1 | HBr | CC(CC)=O | null | 1 | CC(C)(Cc1c[nH]c2c(O)cccc12)NC(=O)OC(C)(C)C.N#CCBr>CC(CC)=O>CC(C)(Cc1c[nH]c2c(OCC#N)cccc12)NC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d323c67d08ed4629b72f93d0bf5352fc | CC(=Cc1c[nH]c2c(OCc3ccccc3)cccc12)[N+](=O)[O-]>>CC(N)Cc1c[nH]c2c(OCc3ccccc3)cccc12 | [H-].[Al+3].[Li+].[H-].[H-].[H-].C(C1=CC=CC=C1)OC=1C=CC=C2C(=CNC12)C=C(C)[N+](=O)[O-].[H-].[Al+3].[Li+].[H-].[H-].[H-]>>C(C1=CC=CC=C1)OC=1C=CC=C2C(=CNC12)CC(C)N | O=[N+:3]([O-])[C:2]([CH3:1])=[CH:4][c:5]1[cH:6][nH:7][c:8]2[c:9]([O:10][CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[cH:18][cH:19][cH:20][c:21]12>>[CH3:1][CH:2]([NH2:3])[CH2:4][c:5]1[cH:6][nH:7][c:8]2[c:9]([O:10][CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[cH:18][cH:19][cH:20][c:21]12 | CC(=Cc1c[nH]c2c(OCc3ccccc3)cccc12)[N+](=O)[O-] | CC(N)Cc1c[nH]c2c(OCc3ccccc3)cccc12 | null | null | O1CCCC1 | Reduction | OtherReaction | 4337e4e8b75c4193a30be38c3139251eb50201a1e90dac1ecfc293dd3e226a46 | 1ad3bfd18d4cba7c52a6c2c4705cfa4e2dc99589d9555154a809489f21a7a436 | c1ccc(COc2cccc3cc[nH]c23)cc1 | O=[N+;H0;D3:1](-[O-])-[C;H0;D3;+0:2](-[C;D1;H3:3])=[CH;D2;+0:4]-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:1>>[C;D1;H3:3]-[CH;D3;+0:2](-[NH2;D1;+0:1])-[CH2;D2;+0:4]-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:1 | null | [] | 30 | CELSIUS | 2 | HOUR | Lithium aluminum hydride (LAH, 24 g, 600 mmol) is added portionwise to dry tetrahydrofuran (1800 mL) at −5° C. to 5° C. A solution of the nitroolefin from above (61.6 g, 200 mmol) in tetrahydrofuran (1200 mL) is added to the LAH solution over 30 minutes while maintaining the temperature at −5° C. to 5° C. When the addi... | 10.6084/m9.figshare.5104873.v1 | null | Enamine | Primary amine | null | null | c1ccccc1.c1ccc2[nH]ccc2c1 | Other | O1CCCC1 | 30 | 2 | CC(=Cc1c[nH]c2c(OCc3ccccc3)cccc12)[N+](=O)[O-]>O1CCCC1>CC(N)Cc1c[nH]c2c(OCc3ccccc3)cccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-579ccc08061142699e0875fb06cf892e | CC(Cc1c[nH]c2c(OCc3ccccc3)cccc12)NC(=O)OC(C)(C)C.N#CCBr>>CC(Cc1c[nH]c2c(OCC#N)cccc12)NC(=O)OC(C)(C)C | C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)OCC1=CC=CC=C1)C)=O.BrCC#N.C([O-])([O-])=O.[K+].[K+]>>C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)OCC#N)C)=O | c1ccc(C[O:9][c:8]2[c:7]3[nH:6][cH:5][c:4]([CH2:3][CH:2]([CH3:1])[NH:17][C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[c:16]3[cH:15][cH:14][cH:13]2)cc1.Br[CH2:10][C:11]#[N:12]>>[CH3:1][CH:2]([CH2:3][c:4]1[cH:5][nH:6][c:7]2[c:8]([O:9][CH2:10][C:11]#[N:12])[cH:13][cH:14][cH:15][c:16]12)[NH:17][C:18](=[O:19])[O:2... | CC(Cc1c[nH]c2c(OCc3ccccc3)cccc12)NC(=O)OC(C)(C)C.N#CCBr | CC(Cc1c[nH]c2c(OCC#N)cccc12)NC(=O)OC(C)(C)C | null | null | C(C)C(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | e33314bc856efe080a739af2d51cb97bb8af73b526448347bb35795fea2551a7 | 969a4609e178674696657c590a647839ca01abd1f90b8f0c9e475b1d6507651b | c1ccc2[nH]ccc2c1 | Br-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3].[c:4]:[c:5](-[O;H0;D2;+0:6]-C-c1:c:c:c:c:c:1):[c:7](:[c:8]):[#7;a:9]:[c:10]>>[N;D1;H0:3]#[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[c:5](:[c:4]):[c:7](:[c:8]):[#7;a:9]:[c:10] | 70.2 | [{"value": 70.2, "product": "C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)OCC#N)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | The crude {1-methyl-2-[7-hydroxy-1H-indol-3-yl]ethyl}-carbamic acid tert-butyl ester from above (29.2 g, 102 mmol theory) is dissolved in methyl ethyl ketone (300 mL) and bromoacetonitrile (20.4 mL, 306 mmol) and potassium carbonate (33.8 g, 250 mmol) is added. The mixture is heated at 80° C. for 2 hours. The solids ar... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether | Ether | c1ccccc1 | null | c1ccc2[nH]ccc2c1 | HBr | C(C)C(=O)C | 80 | null | CC(Cc1c[nH]c2c(OCc3ccccc3)cccc12)NC(=O)OC(C)(C)C.N#CCBr>C(C)C(=O)C>CC(Cc1c[nH]c2c(OCC#N)cccc12)NC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c661d089a084439e8ed863fc8eb54792 | CC(C)(Cc1c[nH]c2c(O)cccc12)NC(=O)OC(C)(C)C.N#Cc1cccnc1Cl>>CC(C)(Cc1c[nH]c2c(Oc3ncccc3C#N)cccc12)NC(=O)OC(C)(C)C | O.ClC1=C(C#N)C=CC=N1.C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)O)(C)C)=O.[H-].[Na+]>>C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)OC1=NC=CC=C1C#N)(C)C)=O | [CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][nH:7][c:8]2[c:9]([OH:10])[cH:19][cH:20][cH:21][c:22]12)[NH:23][C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30].Cl[c:11]1[n:12][cH:13][cH:14][cH:15][c:16]1[C:17]#[N:18]>>[CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][nH:7][c:8]2[c:9]([O:10][c:11]3[n:12][cH:13][cH:14][cH:15][c:... | CC(C)(Cc1c[nH]c2c(O)cccc12)NC(=O)OC(C)(C)C.N#Cc1cccnc1Cl | CC(C)(Cc1c[nH]c2c(Oc3ncccc3C#N)cccc12)NC(=O)OC(C)(C)C | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 99925b30dd2603ae575cba81b58435d015cd6b7267cf347380904f25833af5f2 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2cccc3cc[nH]c23)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11](:[c:12]):[#7;a:13]:[c:14]>>[N;D1;H0:6]#[C:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11](:[c:12]):[#7;a:13]:[c:14]):[#7;a:2]:[c:3] | 96 | [{"value": 96.0, "product": "C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)OC1=NC=CC=C1C#N)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.7, "product": "C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)OC1=NC=CC=C1C#N)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 25 | MINUTE | To a solution of [2-(7-Hydroxy-1H-indol-3-yl)-1,1-dimethyl-ethyl]-carbamic acid tert-butyl ester (274 mg, 0.900 mmol) in dimethylformamide (15 mL) is added sodium hydride (26 mg, 1.07 mmol). The mixture is stirred at ambient temperature for 25 minutes under nitrogen. 2-Chloro-nicotinonitrile (187 mg, 1.35 mmol) is adde... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccc2[nH]ccc2c1 | HCl | CN(C=O)C | null | 0.416667 | CC(C)(Cc1c[nH]c2c(O)cccc12)NC(=O)OC(C)(C)C.N#Cc1cccnc1Cl>CN(C=O)C>CC(C)(Cc1c[nH]c2c(Oc3ncccc3C#N)cccc12)NC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-738a85bc0da5412e8b8a396e20525741 | CC(C)(Cc1c[nH]c2c(Oc3ncccc3C#N)cccc12)NC(=O)OC(C)(C)C>>CCCCCCCCCCCCN | C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)OC1=NC=CC=C1C#N)(C)C)=O.O1CCOCC1.Cl.O1CCOCC1>>CCCCCCCCCCCCN | C[C:2](OC(=O)[NH:13][C:12](C[c:5]1c[nH]c2c(Oc3ncccc3C#N)ccc[c:6]21)([CH3:1])[CH3:11])([CH3:3])[CH3:4]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH2:13] | CC(C)(Cc1c[nH]c2c(Oc3ncccc3C#N)cccc12)NC(=O)OC(C)(C)C | CCCCCCCCCCCCN | null | null | null | Miscellaneous | OtherReaction | 388918355f7c8f9bb89414f7093a44d1c359462eea2423ba0f1998be4941eede | f44468835921508c0283ab83a9324a4767b46169709243988fd96217b6f79842 | null | C-[C;H0;D4;+0:1](-[CH3;D1;+0:2])(-[CH3;D1;+0:3])-O-C(=O)-[NH;D2;+0:4]-[C;H0;D4;+0:5](-[CH3;D1;+0:6])(-[CH3;D1;+0:7])-C-[c;H0;D3;+0:8]1:c:[nH]:c2:[c;H0;D3;+0:9]:1:c:c:c:c:2-O-c1:n:c:c:c:c:1-C#N>>[CH3;D1;+0:7]-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[C:10]-[C:11]-[C:12]-[C:13]-[CH2;D2;+0:6]-... | 83 | [{"value": 83.0, "product": "CCCCCCCCCCCCN", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | {2-[7-(3-Cyano-pyridin-2-yloxy)-1H-indol-3-yl]-1,1-dimethyl-ethyl}-carbamic acid tert-butyl ester (119 mg, 0.293 mmol) is dissolved in 10 mL of 1,4 dioxane. The mixture is cooled to zero degrees Celsius in an ice/water bath. To the mixture is added 10 mL of 4N hydrochloric acid in 1,4 dioxane, and the resulting mixture... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Ether.Nitrile.Boc | Primary amine | c1ccncc1.c1ccc2[nH]ccc2c1 | null | null | Other | null | null | 5 | CC(C)(Cc1c[nH]c2c(Oc3ncccc3C#N)cccc12)NC(=O)OC(C)(C)C>>CCCCCCCCCCCCN |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cf0e1cb12fbf4ee49772ed33ad4ad6b7 | CC(C)(Cc1c[nH]c2c(O)cccc12)NC(=O)OC(C)(C)C.COC(=O)c1ccc(Cl)nc1>>COC(=O)c1ccc(Oc2cccc3c(CC(C)(C)NC(=O)OC(C)(C)C)c[nH]c23)nc1 | O.COC(C1=CN=C(C=C1)Cl)=O.C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)O)(C)C)=O.[H-].[Na+]>>COC(C1=CN=C(C=C1)OC=1C=CC=C2C(=CNC12)CC(C)(C)NC(=O)OC(C)(C)C)=O | [OH:9][c:10]1[cH:11][cH:12][cH:13][c:14]2[c:15]([CH2:16][C:17]([CH3:18])([CH3:19])[NH:20][C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[cH:28][nH:29][c:30]12.Cl[c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:32][n:31]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][c:10]2[cH:11][cH:12][cH:13][c... | CC(C)(Cc1c[nH]c2c(O)cccc12)NC(=O)OC(C)(C)C.COC(=O)c1ccc(Cl)nc1 | COC(=O)c1ccc(Oc2cccc3c(CC(C)(C)NC(=O)OC(C)(C)C)c[nH]c23)nc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 99925b30dd2603ae575cba81b58435d015cd6b7267cf347380904f25833af5f2 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2cccc3cc[nH]c23)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9](:[c:10]):[#7;a:11]:[c:12]>>[c:8]:[c:7](-[O;H0;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[c:9](:[c:10]):[#7;a:11]:[c:12] | 58 | [{"value": 58.0, "product": "COC(C1=CN=C(C=C1)OC=1C=CC=C2C(=CNC12)CC(C)(C)NC(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.9, "product": "COC(C1=CN=C(C=C1)OC=1C=CC=C2C(=CNC12)CC(C)(C)NC(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of [2-(7-hydroxy-1H-indol-3-yl)-1,1-dimethyl-ethyl]-carbamic acid tert-butyl ester (104 mg, 0.342 mmol) in dimethylformamide (10 mL) is added sodium hydride (10 mg, 0.410 mmol). The mixture is stirred at ambient temperature for 30 minutes under nitrogen. 6-Chloro-nicotinic acid methyl ester (99 mg, 0.581 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccc2[nH]ccc2c1 | HCl | CN(C=O)C | null | 0.5 | CC(C)(Cc1c[nH]c2c(O)cccc12)NC(=O)OC(C)(C)C.COC(=O)c1ccc(Cl)nc1>CN(C=O)C>COC(=O)c1ccc(Oc2cccc3c(CC(C)(C)NC(=O)OC(C)(C)C)c[nH]c23)nc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-891086c3a8cc43c7beb58f68c0a282e1 | Cc1csc2ccccc12.O=C1CCC(=O)N1Br>>BrCc1csc2ccccc12 | CC=1C2=C(SC1)C=CC=C2.C1CC(=O)N(C1=O)Br.N(=NC(C#N)(C)C)C(C#N)(C)C>>BrCC=1C2=C(SC1)C=CC=C2 | [CH3:2][c:3]1[cH:4][s:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]12.O=C1CCC(=O)N1[Br:1]>>[Br:1][CH2:2][c:3]1[cH:4][s:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]12 | Cc1csc2ccccc12.O=C1CCC(=O)N1Br | BrCc1csc2ccccc12 | null | null | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1ccc2sccc2c1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[c:3]1:[c:4]:[c:5]:[#16;a:6]:[c:7]:1>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[#16;a:6]:[c:7]:1 | 42.2 | [{"value": 42.0, "product": "BrCC=1C2=C(SC1)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 42.2, "product": "BrCC=1C2=C(SC1)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-Methylbenzo[b]thiophene (9.9 g, 67 mmol) is heated in carbon tetrachloride (133 ml ) to near reflux in the presence of n-bromosuccinimide (11.9 g, 67 mmol, 1.0 eq.). 2,2′Azobisisobutyronitrile (2.2 g, 13.3 mmol, 0.2 eq.) is added and the resulting mixture is refluxed for two hours. After cooling, the reaction mixture... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccc2sccc2c1 | HO- | C(Cl)(Cl)(Cl)Cl | null | null | Cc1csc2ccccc12.O=C1CCC(=O)N1Br>C(Cl)(Cl)(Cl)Cl>BrCc1csc2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f19b2da9cf8f4cdb9a4858498d10bf19 | C[C@H]1CO1.c1ccc2c(c1)CCN2>>CC(O)CN1CCc2ccccc21 | N1CCC2=CC=CC=C12.C1[C@H](C)O1>>OC(CN1CCC2=CC=CC=C12)C | [CH3:1][C@@H:2]1[O:3][CH2:4]1.[NH:5]1[CH2:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]21>>[CH3:1][CH:2]([OH:3])[CH2:4][N:5]1[CH2:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]21 | C[C@H]1CO1.c1ccc2c(c1)CCN2 | CC(O)CN1CCc2ccccc21 | null | null | C(C)O | Heteroatom Alkylation and Arylation | Ring opening of epoxide with amine | d4379babff0daffbed1781da20aedf50f4924ca02a809782fe33166d88fdc20d | 97e758d6c4c8255d25541eb6c6a6f62e7dc30829ea162ca3392731efabc98a65 | c1ccc2c(c1)CCN2 | [C;D1;H3:1]-[C@H;D3;+0:2]1-[CH2;D2;+0:3]-[O;H0;D2;+0:4]-1.[c:5]:[c:6]1:[c:7]-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[C;D1;H3:1]-[CH;D3;+0:2](-[OH;D1;+0:4])-[CH2;D2;+0:3]-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[c:7]:[c:6]-1:[c:5] | 63 | [{"value": 63.0, "product": "OC(CN1CCC2=CC=CC=C12)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.9, "product": "OC(CN1CCC2=CC=CC=C12)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2,3-dihydro-1H-indole (5.74 g, 48.2 mmol), and (S)-propylene oxide (2.8 g, 48.2 mmol) in ethanol (200 mL) is heated at reflux for 18 hours. The resulting mixture is cooled to room temperature, and evaporated to give a crude oil. The material is purified by flash chromatography (25% ethyl acetate/hexanes) t... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Secondary alcohol.Tertiary amine | C1CO1.c1ccc2c(c1)CCN2 | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | null | C(C)O | null | null | C[C@H]1CO1.c1ccc2c(c1)CCN2>C(C)O>CC(O)CN1CCc2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6f7c251455c743cbaee5673ee07fb180 | CC(C)(Cc1c[nH]c2c(OCC(=O)O)cccc12)NC(=O)OC(C)(C)C.CN>>CNC(=O)COc1cccc2c(CC(C)(C)NC(=O)OC(C)(C)C)c[nH]c12 | C(C)(C)(C)OC(=O)NC(CC1=CNC2=C(C=CC=C12)OCC(=O)O)(C)C.CN>>C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)OCC(NC)=O)(C)C)=O | O[C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]([CH2:13][C:14]([CH3:15])([CH3:16])[NH:17][C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[cH:25][nH:26][c:27]12.[CH3:1][NH2:2]>>[CH3:1][NH:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]([CH2:13][C:14]([CH3:15])([CH3:16])[NH:17][... | CC(C)(Cc1c[nH]c2c(OCC(=O)O)cccc12)NC(=O)OC(C)(C)C.CN | CNC(=O)COc1cccc2c(CC(C)(C)NC(=O)OC(C)(C)C)c[nH]c12 | null | null | CN(C=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc2[nH]ccc2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4].[C;D1;H3:5]-[NH2;D1;+0:6]>>[#8:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[C;D1;H3:5] | 100.9 | [{"value": 75.0, "product": "C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)OCC(NC)=O)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.9, "product": "C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)OCC(NC)=O)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of [2-(7-cyanomethoxy-1H-indol-3-yl)-1,1-dimethyl-ethyl]-carbamic acid tert-butyl ester (3.8 mmol) is added 2 N NaOH (10.0 mL, 20 mmol). The reaction mixture is reluxed for 2 hours. The reaction mixture is cooled to room temperature, evaporated to about 10 mL, acidified to pH 3.0 with 1 N HCl. The mixture... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2[nH]ccc2c1 | HO- | CN(C=O)C | null | 3 | CC(C)(Cc1c[nH]c2c(OCC(=O)O)cccc12)NC(=O)OC(C)(C)C.CN>CN(C=O)C>CNC(=O)COc1cccc2c(CC(C)(C)NC(=O)OC(C)(C)C)c[nH]c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d71cbd8395f942d6899bd3f39091693f | C=CC(=O)OC.CC(C)(Cc1c[nH]c2c(OS(=O)(=O)C(F)(F)F)cccc12)NC(=O)OC(C)(C)C>>COC(=O)C=Cc1cccc2c(CC(C)(C)NC(=O)OC(C)(C)C)c[nH]c12 | C(C)(C)(C)OC(=O)NC(CC1=CNC2=C(C=CC=C12)OS(=O)(=O)C(F)(F)F)(C)C.C(C=C)(=O)OC.C(C)N(CC)CC.C(C)(=O)OCC>>COC(C=CC=1C=CC=C2C(=CNC12)CC(C)(C)NC(=O)OC(C)(C)C)=O | [CH3:1][O:2][C:3](=[O:4])[CH:5]=[CH2:6].O=S(=O)(O[c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]([CH2:13][C:14]([CH3:15])([CH3:16])[NH:17][C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[cH:25][nH:26][c:27]12)C(F)(F)F>>[CH3:1][O:2][C:3](=[O:4])[CH:5]=[CH:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]([CH2:13][C:14]([CH3:15])(... | C=CC(=O)OC.CC(C)(Cc1c[nH]c2c(OS(=O)(=O)C(F)(F)F)cccc12)NC(=O)OC(C)(C)C | COC(=O)C=Cc1cccc2c(CC(C)(C)NC(=O)OC(C)(C)C)c[nH]c12 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | CN(C=O)C.[Cl-].[Na+].O | C-C Coupling | OtherReaction | f6e4dd56ea32f13c678e29217fd0c4333a51cf64229efe954763e2e76edb3e0c | e84d2ff35b106b73e905407d80ffdd5c53fba81bdf3725d58511290daa9d3d79 | c1ccc2[nH]ccc2c1 | F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7].[C;D1;H3:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[C:12]=[CH2;D1;+0:13]>>[C;D1;H3:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[C:12]=[CH;D2;+0:13]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7] | 82 | [{"value": 82.0, "product": "COC(C=CC=1C=CC=C2C(=CNC12)CC(C)(C)NC(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.7, "product": "COC(C=CC=1C=CC=C2C(=CNC12)CC(C)(C)NC(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 8 | HOUR | Trifluoro-methanesulfonic acid 3-(2-tert-butoxycarbonylamino-2-methyl-propyl)-1H-indol-7-yl ester (200 mg, 0.46 mmol), methyl acrylate (80 mg, 0.92 mmol) and triethylamine (0.40 mL, 3.0 mmol) is stirred in dimethylformamide (2.0 mL) at room temperature for 30 minutes. Dichlorobis(triphenylphosphine)palladium (31 mg, 0.... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Vinyl | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | TfOH.HO- | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.CN(C=O)C.[Cl-].[Na+].O | 90 | 8 | C=CC(=O)OC.CC(C)(Cc1c[nH]c2c(OS(=O)(=O)C(F)(F)F)cccc12)NC(=O)OC(C)(C)C>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.CN(C=O)C.[Cl-].[Na+].O>COC(=O)C=Cc1cccc2c(CC(C)(C)NC(=O)OC(C)(C)C)c[nH]c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e3ca42b23ffb4a7196121ed97b6f0eec | COC(=O)C=Cc1cccc2c(CC(C)(C)NC(=O)OC(C)(C)C)c[nH]c12>>COC(=O)CCc1cccc2c(CC(C)(C)NC(=O)OC(C)(C)C)c[nH]c12 | C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)CCS(=O)(=O)C)(C)C)=O.COC(C=CC=1C=CC=C2C(=CNC12)CC(C)(C)NC(=O)OC(C)(C)C)=O>>COC(CCC=1C=CC=C2C(=CNC12)CC(C)(C)NC(=O)OC(C)(C)C)=O | [CH3:1][O:2][C:3](=[O:4])[CH:5]=[CH:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]([CH2:13][C:14]([CH3:15])([CH3:16])[NH:17][C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[cH:25][nH:26][c:27]12>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]([CH2:13][C:14]([CH3:15])([CH3:16])[NH:17][C:... | COC(=O)C=Cc1cccc2c(CC(C)(C)NC(=O)OC(C)(C)C)c[nH]c12 | COC(=O)CCc1cccc2c(CC(C)(C)NC(=O)OC(C)(C)C)c[nH]c12 | null | null | null | Reduction | Hydrogenation (double to single) | c04c38f95d7b746e5bdb99c368a7a33956c97b95b54c7ad89be2a85526386ec9 | 9a50abf8d2e4cd9195d7a0cadbe97483a261a81cf70b653cfddd5ecf76d383a6 | c1ccc2[nH]ccc2c1 | [C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D2;+0:5]=[CH;D2;+0:6]-[c:7](:[c:8]):[c:9](:[c:10]):[#7;a:11]:[c:12]>>[C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[c:7](:[c:8]):[c:9](:[c:10]):[#7;a:11]:[c:12] | null | [] | null | null | null | null | 3-[3-(2-tert-Butoxycarbonylamino-2-methyl-propyl)-1H-indol-7-yl]-propionic acid methyl ester is prepared from 3-[3-(2-tert-butoxycarbonylamino-2-methyl-propyl)-1H-indol-7-yl]-acrylic acid methyl ester as described below for the preparation of {2-[7-(2-methanesulfonyl-ethyl)-1H-indol-3-yl]-1,1-dimethyl-ethyl}-carbamic a... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | null | null | c1ccc2[nH]ccc2c1 | null | null | null | null | COC(=O)C=Cc1cccc2c(CC(C)(C)NC(=O)OC(C)(C)C)c[nH]c12>>COC(=O)CCc1cccc2c(CC(C)(C)NC(=O)OC(C)(C)C)c[nH]c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-95f19424f7b140e69f40dc1b673ed663 | C=CC(N)=O.CC(C)(Cc1c[nH]c2c(CS(=O)(=O)C(F)(F)F)cccc12)NC(=O)OC(C)(C)C>>CC(C)(Cc1c[nH]c2c(C=CC(N)=O)cccc12)NC(=O)OC(C)(C)C | C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)CS(=O)(=O)C(F)(F)F)(C)C)=O.C(C=C)(=O)N>>C(C)(C)(C)OC(=O)NC(CC1=CNC2=C(C=CC=C12)C=CC(=O)N)(C)C | [CH2:10]=[CH:11][C:12]([NH2:13])=[O:14].O=S(=O)(C[c:9]1[c:8]2[nH:7][cH:6][c:5]([CH2:4][C:2]([CH3:1])([CH3:3])[NH:19][C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[c:18]2[cH:17][cH:16][cH:15]1)C(F)(F)F>>[CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][nH:7][c:8]2[c:9]([CH:10]=[CH:11][C:12]([NH2:13])=[O:14])[cH:15][cH... | C=CC(N)=O.CC(C)(Cc1c[nH]c2c(CS(=O)(=O)C(F)(F)F)cccc12)NC(=O)OC(C)(C)C | CC(C)(Cc1c[nH]c2c(C=CC(N)=O)cccc12)NC(=O)OC(C)(C)C | null | null | null | C-C Coupling | OtherReaction | 9ee5c848b3529c0571d068ce5ea5cd4d1d3705da2182d3214d2c9187dbcdd8d9 | 9a367fc6597a2c2d2ef687b5d530f141dc98e4ffcb30f47f73afa833e2c55025 | c1ccc2[nH]ccc2c1 | F-C(-F)(-F)-S(=O)(=O)-C-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7].[CH2;D1;+0:8]=[C:9]-[C:10](-[N;D1;H2:11])=[O;D1;H0:12]>>[N;D1;H2:11]-[C:10](=[O;D1;H0:12])-[C:9]=[CH;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7] | null | [] | null | null | null | null | 3-[3-(2-tert-Butoxycarbonylamino-2-methyl-propyl)-1H-indol-7-yl]-acrylamide is prepared from [1,1-dimethyl-2-(7-trifluoromethanesulfonylmethyl-1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester and acrylamide as described for the preparation of Amine 23 (98%). FDMS m/e 356.2 (M++1).
Conditions: See reaction.notes.pro... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Sulfone.Vinyl | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | HF | null | null | null | C=CC(N)=O.CC(C)(Cc1c[nH]c2c(CS(=O)(=O)C(F)(F)F)cccc12)NC(=O)OC(C)(C)C>>CC(C)(Cc1c[nH]c2c(C=CC(N)=O)cccc12)NC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6bb9173e2bfb4e009592dee1e206c9e3 | C=CS(C)(=O)=O.CC(C)(Cc1c[nH]c2c(CS(=O)(=O)C(F)(F)F)cccc12)NC(=O)OC(C)(C)C>>CC(C)(Cc1c[nH]c2c(C=CS(C)(=O)=O)cccc12)NC(=O)OC(C)(C)C | C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)CS(=O)(=O)C(F)(F)F)(C)C)=O.C(=C)S(=O)(=O)C>>C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)C=CS(=O)(=O)C)(C)C)=O | [CH2:10]=[CH:11][S:12]([CH3:13])(=[O:14])=[O:15].O=S(=O)(C[c:9]1[c:8]2[nH:7][cH:6][c:5]([CH2:4][C:2]([CH3:1])([CH3:3])[NH:20][C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[c:19]2[cH:18][cH:17][cH:16]1)C(F)(F)F>>[CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][nH:7][c:8]2[c:9]([CH:10]=[CH:11][S:12]([CH3:13])(=[O:14])... | C=CS(C)(=O)=O.CC(C)(Cc1c[nH]c2c(CS(=O)(=O)C(F)(F)F)cccc12)NC(=O)OC(C)(C)C | CC(C)(Cc1c[nH]c2c(C=CS(C)(=O)=O)cccc12)NC(=O)OC(C)(C)C | null | null | null | C-C Coupling | OtherReaction | 9ee5c848b3529c0571d068ce5ea5cd4d1d3705da2182d3214d2c9187dbcdd8d9 | 9a367fc6597a2c2d2ef687b5d530f141dc98e4ffcb30f47f73afa833e2c55025 | c1ccc2[nH]ccc2c1 | F-C(-F)(-F)-S(=O)(=O)-C-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7].[#16:8]-[C:9]=[CH2;D1;+0:10]>>[#16:8]-[C:9]=[CH;D2;+0:10]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7] | null | [] | null | null | null | null | {2-[7-(2-Methanesulfonyl-vinyl)-1H-indol-3-yl)-1,1-dimethyl-ethyl}-carbamic acid tert-butyl ester is prepared from [1,1-dimethyl-2-(7-trifluoromethanesulfonylmethyl-1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester and methyl vinyl sulfone as described for the preparation of Amine 23 (98%). FDMS m/e=392.2 (M++1).
Co... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Sulfone.Vinyl | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | HF | null | null | null | C=CS(C)(=O)=O.CC(C)(Cc1c[nH]c2c(CS(=O)(=O)C(F)(F)F)cccc12)NC(=O)OC(C)(C)C>>CC(C)(Cc1c[nH]c2c(C=CS(C)(=O)=O)cccc12)NC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2b811ded5cc54bc39f20d5cd39b68575 | CC(C)(Cc1c[nH]c2c(C=CS(C)(=O)=O)cccc12)NC(=O)OC(C)(C)C>>CC(C)(Cc1c[nH]c2c(CCS(C)(=O)=O)cccc12)NC(=O)OC(C)(C)C | C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)C=CS(=O)(=O)C)(C)C)=O>>C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)CCS(=O)(=O)C)(C)C)=O | [CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][nH:7][c:8]2[c:9]([CH:10]=[CH:11][S:12]([CH3:13])(=[O:14])=[O:15])[cH:16][cH:17][cH:18][c:19]12)[NH:20][C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27]>>[CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][nH:7][c:8]2[c:9]([CH2:10][CH2:11][S:12]([CH3:13])(=[O:14])=[O:15])[cH:16][cH:... | CC(C)(Cc1c[nH]c2c(C=CS(C)(=O)=O)cccc12)NC(=O)OC(C)(C)C | CC(C)(Cc1c[nH]c2c(CCS(C)(=O)=O)cccc12)NC(=O)OC(C)(C)C | null | [Pd] | CO | Reduction | Hydrogenation (double to single) | 0bc3968b35f0839c230afb4215314da278abd4e1f10e42ec3012c5512de49ea5 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1ccc2[nH]ccc2c1 | [C;D1;H3:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[CH;D2;+0:5]=[CH;D2;+0:6]-[c:7](:[c:8]):[c:9](:[c:10]):[#7;a:11]:[c:12]>>[C;D1;H3:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[c:7](:[c:8]):[c:9](:[c:10]):[#7;a:11]:[c:12] | 80 | [{"value": 80.0, "product": "C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)CCS(=O)(=O)C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.6, "product": "C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)CCS(=O)(=O)C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of {2-[7-(2-methanesulfonyl-vinyl)-1H-indol-3-yl]-1,1-dimethyl-ethyl}-carbamic acid tert-butyl ester (0.40 g, 1.02,mmol) in methanol (20.0 mL) is added 10% Pd/C (0.10 g) in methanol (2.0 mL). The reaction mixture is purged with hydrogen and hydrogenation is carried out with a hydrogen balloon overnight. T... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccc2[nH]ccc2c1 | null | [Pd].CO | null | null | CC(C)(Cc1c[nH]c2c(C=CS(C)(=O)=O)cccc12)NC(=O)OC(C)(C)C>[Pd].CO>CC(C)(Cc1c[nH]c2c(CCS(C)(=O)=O)cccc12)NC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cc06287670bb4fbd823adbb3133bb5b9 | C=CC#N.CC(C)(Cc1c[nH]c2c(CS(=O)(=O)C(F)(F)F)cccc12)NC(=O)OC(C)(C)C>>CC(C)(Cc1c[nH]c2c(C=CC#N)cccc12)NC(=O)OC(C)(C)C | C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)CS(=O)(=O)C(F)(F)F)(C)C)=O.C(C=C)#N>>C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)C=CC#N)(C)C)=O | [CH2:10]=[CH:11][C:12]#[N:13].O=S(=O)(C[c:9]1[c:8]2[nH:7][cH:6][c:5]([CH2:4][C:2]([CH3:1])([CH3:3])[NH:18][C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[c:17]2[cH:16][cH:15][cH:14]1)C(F)(F)F>>[CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][nH:7][c:8]2[c:9]([CH:10]=[CH:11][C:12]#[N:13])[cH:14][cH:15][cH:16][c:17]12)... | C=CC#N.CC(C)(Cc1c[nH]c2c(CS(=O)(=O)C(F)(F)F)cccc12)NC(=O)OC(C)(C)C | CC(C)(Cc1c[nH]c2c(C=CC#N)cccc12)NC(=O)OC(C)(C)C | null | null | null | C-C Coupling | OtherReaction | 9ee5c848b3529c0571d068ce5ea5cd4d1d3705da2182d3214d2c9187dbcdd8d9 | 9a367fc6597a2c2d2ef687b5d530f141dc98e4ffcb30f47f73afa833e2c55025 | c1ccc2[nH]ccc2c1 | F-C(-F)(-F)-S(=O)(=O)-C-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7].[CH2;D1;+0:8]=[C:9]-[C:10]#[N;D1;H0:11]>>[N;D1;H0:11]#[C:10]-[C:9]=[CH;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7] | null | [] | null | null | null | null | {2-[7-(2-Cyano-vinyl)-1H-indol-3-yl]-1,1-dimethyl-ethyl}-carbamic acid tert-butyl ester is prepared from [1,1-dimethyl-2-(7-trifluoromethanesulfonylmethyl-1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester and acrylonitrile as described for the preparation of Amine 23 (85%). FDMS m/e=339.2 (M++1).
Conditions: See rea... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Sulfone.Vinyl | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | HF | null | null | null | C=CC#N.CC(C)(Cc1c[nH]c2c(CS(=O)(=O)C(F)(F)F)cccc12)NC(=O)OC(C)(C)C>>CC(C)(Cc1c[nH]c2c(C=CC#N)cccc12)NC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-71909e61d7c54e33a7c5b60a56e3b72e | CCOC(=O)Cl.Nc1c(F)cc(F)cc1Br>>CCOC(=O)Nc1c(F)cc(F)cc1Br | C(C)(=O)OCC.CCCCCC.BrC1=C(N)C(=CC(=C1)F)F.ClC(=O)OCC>>BrC1=C(NC(=O)OCC)C(=CC(=C1)F)F | Cl[C:4]([O:3][CH2:2][CH3:1])=[O:5].[NH2:6][c:7]1[c:8]([F:9])[cH:10][c:11]([F:12])[cH:13][c:14]1[Br:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[NH:6][c:7]1[c:8]([F:9])[cH:10][c:11]([F:12])[cH:13][c:14]1[Br:15] | CCOC(=O)Cl.Nc1c(F)cc(F)cc1Br | CCOC(=O)Nc1c(F)cc(F)cc1Br | null | null | N1=CC=CC=C1 | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 94 | [{"value": 94.0, "product": "BrC1=C(NC(=O)OCC)C(=CC(=C1)F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.7, "product": "BrC1=C(NC(=O)OCC)C(=CC(=C1)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a vigorously stirred solution of 2-bromo-4,6-difluoro aniline (100 g, 0.48 mol) in pyridine (400 mL), at 0° C., is added ethyl chloroformate (70 ml, 0.73 mol) at a rate to keep the temperature below 5° C. When addition is complete, the mixture is stirred at 0° C.–5° C. an additional 2 hours while monitoring by TLC (... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccccc1 | HCl | N1=CC=CC=C1 | null | null | CCOC(=O)Cl.Nc1c(F)cc(F)cc1Br>N1=CC=CC=C1>CCOC(=O)Nc1c(F)cc(F)cc1Br |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-05f580e2ae4c4a0682b6fb32ae9bb51f | C#C[Si](C)(C)C.CCOC(=O)Nc1c(F)cc(F)cc1Br>>CCOC(=O)Nc1c(F)cc(F)cc1C#C[Si](C)(C)C | BrC1=C(NC(=O)OCC)C(=CC(=C1)F)F.C(C)N(CC)CC.C[Si](C)(C)C#C>>C[Si](C)(C)C#CC1=C(NC(=O)OCC)C(=CC(=C1)F)F | [CH:15]#[C:16][Si:17]([CH3:18])([CH3:19])[CH3:20].Br[c:14]1[c:7]([NH:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:8]([F:9])[cH:10][c:11]([F:12])[cH:13]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[NH:6][c:7]1[c:8]([F:9])[cH:10][c:11]([F:12])[cH:13][c:14]1[C:15]#[C:16][Si:17]([CH3:18])([CH3:19])[CH3:20] | C#C[Si](C)(C)C.CCOC(=O)Nc1c(F)cc(F)cc1Br | CCOC(=O)Nc1c(F)cc(F)cc1C#C[Si](C)(C)C | null | [Cu]I.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 | CC#N | C-C Coupling | Sonogashira alkyne_aryl halide | 15c08902746c61a960c314898ce6bb5fcc5e189f9e057388c59dba9ec9d0c81c | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7:5]-[C:6]=[O;D1;H0:7]):[c:8].[C;D1;H3:9]-[#14:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[C:13]#[CH;D1;+0:14]>>[C;D1;H3:9]-[#14:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[C:13]#[C;H0;D2;+0:14]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7:5]-[C:6]=[O;D1;H0:7]):[c:8] | 71 | [{"value": 71.0, "product": "C[Si](C)(C)C#CC1=C(NC(=O)OCC)C(=CC(=C1)F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.3, "product": "C[Si](C)(C)C#CC1=C(NC(=O)OCC)C(=CC(=C1)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a 2 L flask, 2-bromo-4,6-difluoro-N-carbethoxy aniline (42 g, 150 mmol) in CH3CN (500 mL) is degassed with vacuum and purged with N2. Dichlorobis(triphenylphosphine)palladium(II) (10.5 g, 15 mmol, 10 mol %), followed by CuI (710 mg, 4 mmol, 2.5 mol %) and triethyl amine (41 mL) are added and rinsed in with 100 mL of... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | [Cu]I.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.CC#N | null | null | C#C[Si](C)(C)C.CCOC(=O)Nc1c(F)cc(F)cc1Br>[Cu]I.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.CC#N>CCOC(=O)Nc1c(F)cc(F)cc1C#C[Si](C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a9d09bb02bf34689b618636a056c80b1 | CCOC(=O)Nc1c(F)cc(F)cc1C#C[Si](C)(C)C>>CC[O-].Fc1cc(F)c2[nH]ccc2c1 | [H-].[Na+].C[Si](C)(C)C#CC1=C(NC(=O)OCC)C(=CC(=C1)F)F.C(C)(=O)OCC.CCCCCC>>[O-]CC.[Na+].FC=1C=C2C=CNC2=C(C1)F | C[Si](C)(C)C#[C:12][c:13]1[c:9]([NH:10][C:11](=O)[O:3][CH2:2][CH3:1])[c:7]([F:8])[cH:6][c:5]([F:4])[cH:14]1>>[CH3:1][CH2:2][O-:3].[F:4][c:5]1[cH:6][c:7]([F:8])[c:9]2[nH:10][cH:11][cH:12][c:13]2[cH:14]1 | CCOC(=O)Nc1c(F)cc(F)cc1C#C[Si](C)(C)C | CC[O-].Fc1cc(F)c2[nH]ccc2c1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | d93159aaafb07623ac70398631606f6fda7f6909e2825456e8155a5393ab3f67 | 96f6078eb7a094b71a64f7dd2ec28cce2fb0038aa097ceee40707bfd91d8a122 | c1ccc2[nH]ccc2c1 | C-[Si](-C)(-C)-C#[C;H0;D2;+0:1]-[c:2](:[c:3]):[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:6](=O)-[O;H0;D2;+0:7]-[C:8]-[C;D1;H3:9]):[c:10]>>[C;D1;H3:9]-[C:8]-[O-;H0;D1:7].[c:3]:[c:2]1:[cH;D2;+0:1]:[cH;D2;+0:6]:[nH;D2;+0:5]:[c:4]:1:[c:10] | 78.4 | [{"value": 78.0, "product": "FC=1C=C2C=CNC2=C(C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.4, "product": "FC=1C=C2C=CNC2=C(C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Fresh sodium ethoxide is prepared by carefully adding NaH (16 g of 60% oil dispersion, 400 mmol) to 550 mL of ethanol under N2. 2-(Trimethylsilylethynyl)-4,6-difluoro-N-carbethoxyaniline (28 g, 100 mmol) in 150 mL of ethanol is added and reaction is stirred at room temperature approximately 45 minutes, while monitoring... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Alkyne.Silyl protective group | null | c1ccccc1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | HO- | C(C)O | null | null | CCOC(=O)Nc1c(F)cc(F)cc1C#C[Si](C)(C)C>C(C)O>CC[O-].Fc1cc(F)c2[nH]ccc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-563d6e04fa2144da9e95cdda593c8abd | ClI.Fc1cc(F)c2[nH]ccc2c1.O=S(=O)(Cl)c1ccccc1>>O=S(=O)(c1ccccc1)n1cc(I)c2cc(F)cc(F)c21 | C1(=CC=CC=C1)S(=O)(=O)Cl.ICl.C(Cl)Cl.FC=1C=C2C=CNC2=C(C1)F>>C1(=CC=CC=C1)S(=O)(=O)N1C=C(C2=CC(=CC(=C12)F)F)I | Cl[I:13].[nH:10]1[cH:11][cH:12][c:14]2[cH:15][c:16]([F:17])[cH:18][c:19]([F:20])[c:21]12.Cl[S:2](=[O:1])(=[O:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1>>[O:1]=[S:2](=[O:3])([c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[n:10]1[cH:11][c:12]([I:13])[c:14]2[cH:15][c:16]([F:17])[cH:18][c:19]([F:20])[c:21]12 | ClI.Fc1cc(F)c2[nH]ccc2c1.O=S(=O)(Cl)c1ccccc1 | O=S(=O)(c1ccccc1)n1cc(I)c2cc(F)cc(F)c21 | null | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC | N1=CC=CC=C1.[OH-].[Na+].C1(=CC=CC=C1)C | Miscellaneous | OtherReaction | 65c4847c06bac21126f9fb144209ef63ce8313245b1b724a321d6cd031cec566 | 51ac21fb371666dad6c719abf761fc77677c24795c2c33a15b0a4d5159f01965 | O=S(=O)(c1ccccc1)n1ccc2ccccc21 | Cl-[I;H0;D1;+0:1].Cl-[S;H0;D4;+0:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5](:[c:6]):[c:7].[c:8]:[c:9]1:[cH;D2;+0:10]:[c:11]:[nH;D2;+0:12]:[c:13]:1:[c:14]>>[I;H0;D1;+0:1]-[c;H0;D3;+0:10]1:[c:11]:[n;H0;D3;+0:12](-[S;H0;D4;+0:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5](:[c:6]):[c:7]):[c:13](:[c:14]):[c:9]:1:[c:8] | 87 | [{"value": 87.0, "product": "C1(=CC=CC=C1)S(=O)(=O)N1C=C(C2=CC(=CC(=C12)F)F)I", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | The 1.0 M ICl in CH2Cl2 (43 ml, 43 mmol) is added to a solution of 5,7-difluoroindole (6 g, 39 mmol) in 35 ml pyridine under N2 at 0° C. and the resulting mixture is stirred for 30 minutes. The reaction is diluted with toluene and washed with brine, 1N HCl, 1N NaOH, dried (Na2SO4), filtered and concentrated. The crude ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | Aromatic halide | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | HCl | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.N1=CC=CC=C1.[OH-].[Na+].C1(=CC=CC=C1)C | null | 0.5 | ClI.Fc1cc(F)c2[nH]ccc2c1.O=S(=O)(Cl)c1ccccc1>[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.N1=CC=CC=C1.[OH-].[Na+].C1(=CC=CC=C1)C>O=S(=O)(c1ccccc1)n1cc(I)c2cc(F)cc(F)c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-399e2e2cad6e47cab2717298fec2cb59 | CC(C(O)c1cn(S(=O)(=O)c2ccccc2)c2c(F)cc(F)cc12)N(Cc1ccccc1)Cc1ccccc1>>C[C@@H](Cc1c[nH]c2c(F)cc(F)cc12)N(Cc1ccccc1)Cc1ccccc1 | [H-].[Al+3].[Li+].[H-].[H-].[H-].C(C1=CC=CC=C1)N(CC1=CC=CC=C1)C(C(O)C1=CN(C2=C(C=C(C=C12)F)F)S(=O)(=O)C1=CC=CC=C1)C>>C(C1=CC=CC=C1)N([C@H](CC1=CNC2=C(C=C(C=C12)F)F)C)CC1=CC=CC=C1 | O=S(=O)(c1ccccc1)[n:6]1[cH:5][c:4]([CH:3](O)[CH:2]([CH3:1])[N:15]([CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[CH2:23][c:24]2[cH:25][cH:26][cH:27][cH:28][cH:29]2)[c:14]2[c:7]1[c:8]([F:9])[cH:10][c:11]([F:12])[cH:13]2>>[CH3:1][C@@H:2]([CH2:3][c:4]1[cH:5][nH:6][c:7]2[c:8]([F:9])[cH:10][c:11]([F:12])[cH:13][c:14]1... | CC(C(O)c1cn(S(=O)(=O)c2ccccc2)c2c(F)cc(F)cc12)N(Cc1ccccc1)Cc1ccccc1 | C[C@@H](Cc1c[nH]c2c(F)cc(F)cc12)N(Cc1ccccc1)Cc1ccccc1 | null | null | O1CCOCC1.O1CCCC1 | Reduction | OtherReaction | 314558446aae30b1e0db2c7845b84a181628981e07c25fc4a354bd6222968a70 | 46f8a11b80b06e754a5a34198d843342612a5e7ede950bda52ce3a500cedba0b | c1ccc(CN(CCc2c[nH]c3ccccc23)Cc2ccccc2)cc1 | O-[CH;D3;+0:1](-[CH;D3;+0:2](-[C;D1;H3:3])-[#7:4](-[C:5])-[C:6])-[c:7]1:[c:8]:[c:9](:[c:10]):[n;H0;D3;+0:11](-S(=O)(=O)-c2:c:c:c:c:c:2):[c:12]:1>>[C:5]-[#7:4](-[C:6])-[C@@H;D3;+0:2](-[C;D1;H3:3])-[CH2;D2;+0:1]-[c:7]1:[c:8]:[c:9](:[c:10]):[nH;D2;+0:11]:[c:12]:1 | 93.1 | [{"value": 86.0, "product": "C(C1=CC=CC=C1)N([C@H](CC1=CNC2=C(C=C(C=C12)F)F)C)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.1, "product": "C(C1=CC=CC=C1)N([C@H](CC1=CNC2=C(C=C(C=C12)F)F)C)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Lithium aluminum hydride (LAH) (0.7 g, 18 mmol) is added portionwise to a dioxane/tetrahydrofuran (90 ml/10 ml) solution of 2-(N,N-dibenzylamino)-1-(1-benzenesulfonyl-5,7-difluoro-1H-indol-3-yl)-propan-1-ol (1.9 g, 3.3 mmol) under N2 at 0° C. After the addition is complete, the reaction is allowed to warm to room tempe... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | null | c1ccccc1.c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1.c1ccccc1 | HO- | O1CCOCC1.O1CCCC1 | null | null | CC(C(O)c1cn(S(=O)(=O)c2ccccc2)c2c(F)cc(F)cc12)N(Cc1ccccc1)Cc1ccccc1>O1CCOCC1.O1CCCC1>C[C@@H](Cc1c[nH]c2c(F)cc(F)cc12)N(Cc1ccccc1)Cc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-825e0f147af6474489eb0897d71af069 | CI.C[C@H](Cc1c[nH]c2c(F)cc(F)cc12)N(Cc1ccccc1)Cc1ccccc1>>C[C@H](Cc1cn(C)c2c(F)cc(F)cc12)N(Cc1ccccc1)Cc1ccccc1 | [H-].[Na+].C(C1=CC=CC=C1)N([C@@H](CC1=CNC2=C(C=C(C=C12)F)F)C)CC1=CC=CC=C1.IC>>C(C1=CC=CC=C1)N([C@@H](CC1=CN(C2=C(C=C(C=C12)F)F)C)C)CC1=CC=CC=C1 | I[CH3:7].[CH3:1][C@H:2]([CH2:3][c:4]1[cH:5][nH:6][c:8]2[c:9]([F:10])[cH:11][c:12]([F:13])[cH:14][c:15]12)[N:16]([CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1)[CH2:24][c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1>>[CH3:1][C@H:2]([CH2:3][c:4]1[cH:5][n:6]([CH3:7])[c:8]2[c:9]([F:10])[cH:11][c:12]([F:13])[cH:14][c:15]12... | CI.C[C@H](Cc1c[nH]c2c(F)cc(F)cc12)N(Cc1ccccc1)Cc1ccccc1 | C[C@H](Cc1cn(C)c2c(F)cc(F)cc12)N(Cc1ccccc1)Cc1ccccc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 5f4295751cbf2eac77c77b599ebb727e1800dd106de3a7476670f0ac76dbeba5 | 7a358c636daddc97c1fb4c29f378044d7eac3f01815d9966e599841f642d631a | c1ccc(CN(CCc2c[nH]c3ccccc23)Cc2ccccc2)cc1 | I-[CH3;D1;+0:1].[c:2]:[c:3]1:[c:4]:[c:5]:[c:6]:[nH;D2;+0:7]:1>>[CH3;D1;+0:1]-[n;H0;D3;+0:7]1:[c:6]:[c:5]:[c:4]:[c:3]:1:[c:2] | 89 | [{"value": 89.0, "product": "C(C1=CC=CC=C1)N([C@@H](CC1=CN(C2=C(C=C(C=C12)F)F)C)C)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | NaH (180 mg of 60% oil dispersion, 4.5 mmol) is added to a solution of dibenzyl-[2-(5,7-difluoro-1H-indol-3-yl)-1(R)-methyl-ethyl]-amine (1.4 g, 3.6 mmol) in 20 ml dimethylformamide under N2 at 0° C. The resulting mixture is stirred for 20 minutes, then is allowed to warm to room temperature over 20 minutes. A 5 ml sol... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1.c1ccccc1 | HI | CN(C=O)C | null | 0.333333 | CI.C[C@H](Cc1c[nH]c2c(F)cc(F)cc12)N(Cc1ccccc1)Cc1ccccc1>CN(C=O)C>C[C@H](Cc1cn(C)c2c(F)cc(F)cc12)N(Cc1ccccc1)Cc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-512b38c506b9498185831786eee0d90a | CN(C)C=O.COc1cc2cc[nH]c2cc1F>>COc1cc2c(C=O)c[nH]c2cc1F | COC=1C=C2C=CNC2=CC1F.CN(C=O)C.O=P(Cl)(Cl)Cl.CN(C=O)C.[OH-].[Na+]>>FC1=C(C=C2C(=CNC2=C1)C=O)OC | CN(C)[CH:7]=[O:8].[CH3:1][O:2][c:3]1[cH:4][c:5]2[cH:6][cH:9][nH:10][c:11]2[cH:12][c:13]1[F:14]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([CH:7]=[O:8])[cH:9][nH:10][c:11]2[cH:12][c:13]1[F:14] | CN(C)C=O.COc1cc2cc[nH]c2cc1F | COc1cc2c(C=O)c[nH]c2cc1F | null | null | null | C-C Coupling | OtherReaction | d9ced6f2d1d9464eec389101e666f325da08b904b074a7a40088934efbb18d56 | f0bd75a0630092c31f21f61f4a015c77ae0dff14a0b742b4370d7a38fda490f7 | c1ccc2[nH]ccc2c1 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].[c:3]:[c:4]1:[#7;a:5]:[c:6]:[cH;D2;+0:7]:[c:8]:1:[c:9]>>[O;D1;H0:2]=[CH;D2;+0:1]-[c;H0;D3;+0:7]1:[c:6]:[#7;a:5]:[c:4](:[c:3]):[c:8]:1:[c:9] | 95 | [{"value": 95.0, "product": "FC1=C(C=C2C(=CNC2=C1)C=O)OC", "details": "PERCENTYIELD", "is_desired": false}] | 10 | CELSIUS | 15 | MINUTE | POCl3 (10.9 ml, 71 mmol) is added dropwise to 21 ml of dimethylformamide under N2 at 10–20° C., is stirred 15 minutes, then a 13 ml dimethylformamide solution of 5-methoxy-6-fluoro-indole (J. Med. Chem., 22:63–69, 1979; 10.7 g, 64.7 mmol) is added at a rate to keep the reaction temperature between 10 and 20° C. After t... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Aldehyde | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | Other | null | 10 | 0.25 | CN(C)C=O.COc1cc2cc[nH]c2cc1F>>COc1cc2c(C=O)c[nH]c2cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a2dc7544472245ceae1897b7f180e6d7 | CC[N+](=O)[O-].COc1cc2c(C=O)c[nH]c2cc1F>>COc1cc2c(C=C(C)[N+](=O)[O-])c[nH]c2cc1F | [N+](=O)([O-])CC.FC1=C(C=C2C(=CNC2=C1)C=O)OC.C(C)(=O)[O-].[NH4+]>>FC1=C(C=C2C(=CNC2=C1)C=C(C)[N+](=O)[O-])OC | [CH2:8]([CH3:9])[N+:10](=[O:11])[O-:12].O=[CH:7][c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:17]([F:18])[cH:16][c:15]2[nH:14][cH:13]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([CH:7]=[C:8]([CH3:9])[N+:10](=[O:11])[O-:12])[cH:13][nH:14][c:15]2[cH:16][c:17]1[F:18] | CC[N+](=O)[O-].COc1cc2c(C=O)c[nH]c2cc1F | COc1cc2c(C=C(C)[N+](=O)[O-])c[nH]c2cc1F | null | null | null | C-C Coupling | OtherReaction | 7ede86d40d3d69f429dde089476c8b7ffa9b74bf3050590255e6323d013c2daf | f736727903c0ad5511d468246b8e380897fd19905174c118ffa4ed4d3651f6ea | c1ccc2[nH]ccc2c1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[c:6]:1.[C;D1;H3:7]-[CH2;D2;+0:8]-[#7;+:9](-[O;-;D1;H0:10])=[O;D1;H0:11]>>[C;D1;H3:7]-[C;H0;D3;+0:8](=[CH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[c:6]:1)-[#7;+:9](-[O;-;D1;H0:10])=[O;D1;H0:11] | 92 | [{"value": 92.0, "product": "FC1=C(C=C2C(=CNC2=C1)C=C(C)[N+](=O)[O-])OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.7, "product": "FC1=C(C=C2C(=CNC2=C1)C=C(C)[N+](=O)[O-])OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 3 | HOUR | A mixture of nitroethane(44 ml, 611 mmol), 6-fluoro-5-methoxy-1H-indole-3-carbaldehyde (11.8 g, 61 mmol), and ammonium acetate(1.78 g, 23 mmol) is stirred at 100° C. for 3 hours, allowed to cool, and is filtered to give 14 g of 6-fluoro-5-methoxy-3-(2-nitro-propenyl)-1H-indole (92%).
Conditions: See reaction.notes.proc... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitro group | Enamine | null | null | c1ccc2[nH]ccc2c1 | HO- | null | 100 | 3 | CC[N+](=O)[O-].COc1cc2c(C=O)c[nH]c2cc1F>>COc1cc2c(C=C(C)[N+](=O)[O-])c[nH]c2cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f7a1ba14ffa947f1be82f724f443f402 | N#CCBr.Oc1cccc2[nH]ccc12>>N#CCOc1cccc2[nH]ccc12 | BrCC#N.OC1=C2C=CNC2=CC=C1.[H-].[Na+]>>N1C=CC2=C(C=CC=C12)OCC#N | Br[CH2:3][C:2]#[N:1].[OH:4][c:5]1[cH:6][cH:7][cH:8][c:9]2[nH:10][cH:11][cH:12][c:13]12>>[N:1]#[C:2][CH2:3][O:4][c:5]1[cH:6][cH:7][cH:8][c:9]2[nH:10][cH:11][cH:12][c:13]12 | N#CCBr.Oc1cccc2[nH]ccc12 | N#CCOc1cccc2[nH]ccc12 | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc2[nH]ccc2c1 | Br-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3].[#7;a:4]:[c:5]:[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]>>[#7;a:4]:[c:5]:[c:6]:[c:7](-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3]):[c:9] | 97 | [{"value": 97.0, "product": "N1C=CC2=C(C=CC=C12)OCC#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.8, "product": "N1C=CC2=C(C=CC=C12)OCC#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A 0° C. solution of 4-hydroxyindole (20 g, 150 mmol) in 500 ml of dimethylformamide is treated with NaH (60% dispersion in mineral oil; 6.6 g, 165 mmol). After 30 minutes, bromoacetonitrile (11.5 ml, 165 mmol) is added, and the resulting mixture is allowed to slowly warm to ambient temperature and stir for 3 days. The ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2[nH]ccc2c1 | HBr | CN(C=O)C.C(C)(=O)OCC | null | 0.5 | N#CCBr.Oc1cccc2[nH]ccc12>CN(C=O)C.C(C)(=O)OCC>N#CCOc1cccc2[nH]ccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7a4c2b57e5d34d249997ab15f038576e | N#CCBr.c1ccc2[nH]ccc2c1>>N#CCn1ccc2ccccc21 | BrCC#N.N1C=CC2=CC=CC=C12.[H-].[Na+]>>N1(C=CC2=CC=CC=C12)CC#N | Br[CH2:3][C:2]#[N:1].[nH:4]1[cH:5][cH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]12>>[N:1]#[C:2][CH2:3][n:4]1[cH:5][cH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]12 | N#CCBr.c1ccc2[nH]ccc2c1 | N#CCn1ccc2ccccc21 | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 92cc004fc3e2a92f5c9aa0385cdf93f1126e35d5aa485f4f5fe9240c9543c8fe | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc2[nH]ccc2c1 | Br-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3].[c:4]:[c:5]1:[c:6]:[c:7]:[c:8]:[nH;D2;+0:9]:1>>[N;D1;H0:3]#[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:9]1:[c:8]:[c:7]:[c:6]:[c:5]:1:[c:4] | 27.1 | [{"value": 27.0, "product": "N1(C=CC2=CC=CC=C12)CC#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 27.1, "product": "N1(C=CC2=CC=CC=C12)CC#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | A 0° C. solution of indole (7 g, 59.8 mmol) in 200 ml of dimethylformamide is treated with NaH (60% dispersion in mineral oil; 3.1 g, 77.7 mmol). After 20 minutes, bromoacetonitrile (4.2 ml, 59.8 mmol) is added, and the resulting mixture is allowed to slowly warm to ambient temperature and stir overnight. The reaction ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | HBr | CN(C=O)C.C(C)(=O)OCC | null | 0.333333 | N#CCBr.c1ccc2[nH]ccc2c1>CN(C=O)C.C(C)(=O)OCC>N#CCn1ccc2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a38914c6c46e4909b2e3f31bcb03efa9 | CC(C)[N+](=O)[O-].CN(C)CCc1c[nH]c2cccc(F)c12>>CC(C)(Cc1c[nH]c2cccc(F)c12)[N+](=O)[O-] | C(C)(=O)O.FC1=C2C(=CNC2=CC=C1)CCN(C)C.[OH-].[Na+].[N+](=O)([O-])C(C)C>>FC1=C2C(=CNC2=CC=C1)CC(C)([N+](=O)[O-])C | [CH3:1][CH:2]([CH3:3])[N+:15](=[O:16])[O-:17].CN(C)C[CH2:4][c:5]1[cH:6][nH:7][c:8]2[cH:9][cH:10][cH:11][c:12]([F:13])[c:14]12>>[CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][nH:7][c:8]2[cH:9][cH:10][cH:11][c:12]([F:13])[c:14]12)[N+:15](=[O:16])[O-:17] | CC(C)[N+](=O)[O-].CN(C)CCc1c[nH]c2cccc(F)c12 | CC(C)(Cc1c[nH]c2cccc(F)c12)[N+](=O)[O-] | null | null | C(C)(=O)OCC.[Cl-].[Na+].O | C-C Coupling | OtherReaction | 410d0ecf550dfec32b5bd37f61aeafc75533d5e4329aa3110c08acb15e21dcaa | fc73a0ba4f6f90cb21df47612bcde105fcd2a049cd56b52924f944fc6a6cbe55 | c1ccc2[nH]ccc2c1 | C-N(-C)-C-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[C;D1;H3:7]-[CH;D3;+0:8](-[C;D1;H3:9])-[#7;+:10](-[O;-;D1;H0:11])=[O;D1;H0:12]>>[C;D1;H3:7]-[C;H0;D4;+0:8](-[C;D1;H3:9])(-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:1)-[#7;+:10](-[O;-;D1;H0:11])=[O;D1;H0:12] | 76 | [{"value": 76.0, "product": "FC1=C2C(=CNC2=CC=C1)CC(C)([N+](=O)[O-])C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A slurry of 4-fluoro-3-(dimethylaminoethyl)-1H-indole (4.3 g, 22.4 mmol) in 14.1 ml of 2-nitropropane is treated with solid NaOH (941 mg, 23.5 mmol), and the resulting mixture is heated at reflux overnight. After cooling to ambient temperature, the reaction mixture is acidified with 10%. aqueous acetic acid (25 ml) and... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Tertiary amine | Nitro group | null | null | c1ccc2[nH]ccc2c1 | Other | C(C)(=O)OCC.[Cl-].[Na+].O | null | 0.5 | CC(C)[N+](=O)[O-].CN(C)CCc1c[nH]c2cccc(F)c12>C(C)(=O)OCC.[Cl-].[Na+].O>CC(C)(Cc1c[nH]c2cccc(F)c12)[N+](=O)[O-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c7d2f163f53541348b1ec62b194c7f1c | C=[N+](C)C.COC(=O)c1cccc2[nH]ccc12.[I-]>>COC(=O)c1cccc2[nH]cc(CN(C)C)c12.I | N1C=CC=2C(=CC=CC12)C(=O)OC.C[N+](=C)C.[I-]>>I.COC(=O)C=1C=2C(=CNC2C=CC1)CN(C)C | [CH2:13]=[N+:14]([CH3:15])[CH3:16].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]2[nH:10][cH:11][cH:12][c:17]12.[I-:18]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]2[nH:10][cH:11][c:12]([CH2:13][N:14]([CH3:15])[CH3:16])[c:17]12.[IH:18] | C=[N+](C)C.COC(=O)c1cccc2[nH]ccc12.[I-] | COC(=O)c1cccc2[nH]cc(CN(C)C)c12.I | null | null | C(C)(=O)O | C-C Coupling | OtherReaction | 6f78ebae7a6e5f9c15e0d6ab78f58f64a17b670729ecfc39fbb9b9e11c788fae | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc2[nH]ccc2c1 | [#8:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]1:[cH;D2;+0:6]:[c:7]:[#7;a:8]:[c:9]:1:[c:10].[C;D1;H3:11]-[N+;H0;D3:12](-[C;D1;H3:13])=[CH2;D1;+0:14].[I-;H0;D0:15]>>[#8:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]1:[c:9](:[c:10]):[#7;a:8]:[c:7]:[c;H0;D3;+0:6]:1-[CH2;D2;+0:14]-[N;H0;D3;+0:12](-[C;D1;H3:11])-[C;D1;H3:13].[IH;D0;+0:15] | null | [] | 65 | CELSIUS | null | null | Methyl indole-4-carboxylate (7.0 g, 40 mmol) and Eschenmoser's salt (N,N-dimethylmethyleneammonium iodide; 7.8 g, 42 mmol) are combined in 130 ml of acetic acid. After heating at 65° C. for 2 hours, the reaction mixture is concentrated in vacuo. The resulting solid is triturated with ethyl acetate, filtered and dried i... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | null | C(C)(=O)O | 65 | null | C=[N+](C)C.COC(=O)c1cccc2[nH]ccc12.[I-]>C(C)(=O)O>COC(=O)c1cccc2[nH]cc(CN(C)C)c12.I |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4866853a2f2646d1ab550d48cec29d92 | CC(C)[N+](=O)[O-].COC(=O)c1cccc2[nH]cc(CN(C)C)c12>>COC(=O)c1cccc2[nH]cc(CC(C)(C)[N+](=O)[O-])c12 | I.COC(=O)C=1C=2C(=CNC2C=CC1)CN(C)C.S(=O)(=O)(OC)OC.C[O-].[Na+].[N+](=O)([O-])C(C)C>>COC(=O)C=1C=2C(=CNC2C=CC1)CC(C)([N+](=O)[O-])C | [CH:14]([CH3:15])([CH3:16])[N+:17](=[O:18])[O-:19].CN(C)[CH2:13][c:12]1[cH:11][nH:10][c:9]2[cH:8][cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:20]21>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]2[nH:10][cH:11][c:12]([CH2:13][C:14]([CH3:15])([CH3:16])[N+:17](=[O:18])[O-:19])[c:20]12 | CC(C)[N+](=O)[O-].COC(=O)c1cccc2[nH]cc(CN(C)C)c12 | COC(=O)c1cccc2[nH]cc(CC(C)(C)[N+](=O)[O-])c12 | null | null | CO.C(C)(=O)OCC.[NH4+].[Cl-] | C-C Coupling | OtherReaction | 410d0ecf550dfec32b5bd37f61aeafc75533d5e4329aa3110c08acb15e21dcaa | fc73a0ba4f6f90cb21df47612bcde105fcd2a049cd56b52924f944fc6a6cbe55 | c1ccc2[nH]ccc2c1 | C-N(-C)-[CH2;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[c:6]:1.[C;D1;H3:7]-[CH;D3;+0:8](-[C;D1;H3:9])-[#7;+:10](-[O;-;D1;H0:11])=[O;D1;H0:12]>>[C;D1;H3:7]-[C;H0;D4;+0:8](-[C;D1;H3:9])(-[CH2;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[c:6]:1)-[#7;+:10](-[O;-;D1;H0:11])=[O;D1;H0:12] | null | [] | null | null | 8 | HOUR | A 0° C. solution of 3-dimethylaminomethyl-1H-indole-4-carboxylic acid methyl ester hydroiodide (19 g, 52.7 mmol) in 75 ml of methanol and 75 ml of 2-nitropropane is treated with dimethyl sulfate (10 ml, 105.5 mmol) and solid sodium methoxide (6.3 g, 110.6.mmol) sequentially. The resulting mixture is allowed to warm to ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Tertiary amine | Nitro group | null | null | c1ccc2[nH]ccc2c1 | Other | CO.C(C)(=O)OCC.[NH4+].[Cl-] | null | 8 | CC(C)[N+](=O)[O-].COC(=O)c1cccc2[nH]cc(CN(C)C)c12>CO.C(C)(=O)OCC.[NH4+].[Cl-]>COC(=O)c1cccc2[nH]cc(CC(C)(C)[N+](=O)[O-])c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3dd918785d8c438daa628a564fa5be31 | CNC.COC(=O)c1ccc2c(C=O)c[nH]c2c1>>COC(=O)c1ccc2c(N(C)C)cn(C)c2c1.N | [BH4-].[Na+].C(=O)C1=CNC2=CC(=CC=C12)C(=O)OC.CNC.CO>>N.CO.COC(=O)C1=CC=C2C(=CN(C2=C1)C)N(C)C | [NH:12]([CH3:13])[CH3:14].O=[CH:17][c:11]1[c:10]2[cH:9][cH:8][c:7]([C:5]([O:4][CH3:3])=[O:6])[cH:19][c:18]2[nH:16][cH:15]1>>[CH3:3][O:4][C:5](=[O:6])[c:7]1[cH:8][cH:9][c:10]2[c:11]([N:12]([CH3:13])[CH3:14])[cH:15][n:16]([CH3:17])[c:18]2[cH:19]1.[NH3:20] | CNC.COC(=O)c1ccc2c(C=O)c[nH]c2c1 | COC(=O)c1ccc2c(N(C)C)cn(C)c2c1.N | null | null | C(Cl)(Cl)Cl.[Cl-].[Na+].O | Heteroatom Alkylation and Arylation | OtherReaction | c7ea80b5fb60b4ece971cabaae8f4e0c032ddb9c0e263eb0712e682a442ca3ff | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc2[nH]ccc2c1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[nH;D2;+0:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[C;D1;H3:9]-[NH;D2;+0:10]-[C;D1;H3:11]>>[C;D1;H3:9]-[N;H0;D3;+0:10](-[C;D1;H3:11])-[c;H0;D3;+0:2]1:[c:3]:[n;H0;D3;+0:4](-[CH3;D1;+0:1]):[c:5](:[c:6]):[c:7]:1:[c:8] | 99 | [{"value": 20.0, "product": "N.CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.0, "product": "COC(=O)C1=CC=C2C(=CN(C2=C1)C)N(C)C", "details": "PERCENTYIELD", "is_desired": false}] | 55 | CELSIUS | 45 | MINUTE | A solution of methyl 3-formylindole-6-carboxylate (8.0 g, 39.3 mmol) in 270 ml methanol is treated with dimethylamine (40% aqueous; 267 ml, 2.56 mol) at ambient temperature. After 45 minutes, NaBH4 (4.45 g, 118.1 mmol) is added, and the resulting mixture is heated at 55° C. for 3 hours. The reaction mixture is allowed ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2cc[nH]c2c1 | c1ccc2cc[nH]c2c1 | null | C(Cl)(Cl)Cl.[Cl-].[Na+].O | 55 | 0.75 | CNC.COC(=O)c1ccc2c(C=O)c[nH]c2c1>C(Cl)(Cl)Cl.[Cl-].[Na+].O>COC(=O)c1ccc2c(N(C)C)cn(C)c2c1.N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-862fad865d5d4554aecfa4b466bec1e1 | CC(C)(Cc1c[nH]c2c(O)cccc12)NC(=O)OC(C)(C)C.COC(=O)CCl>>COCOC(=O)c1cccc2c(CC(C)(C)NC(=O)OC(C)(C)C)c[nH]c12 | C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)O)(C)C)=O.CN(C=O)C.[H-].[Na+].COC(CCl)=O>>C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)C(=O)OCOC)(C)C)=O | [OH:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]([CH2:13][C:14]([CH3:15])([CH3:16])[NH:17][C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[cH:25][nH:26][c:27]12.ClC[C:3]([O:2][CH3:1])=[O:4]>>[CH3:1][O:2][CH2:3][O:4][C:5](=[O:6])[c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]([CH2:13][C:14]([CH3:15])([CH3:16])[NH:17][C:18](=... | CC(C)(Cc1c[nH]c2c(O)cccc12)NC(=O)OC(C)(C)C.COC(=O)CCl | COCOC(=O)c1cccc2c(CC(C)(C)NC(=O)OC(C)(C)C)c[nH]c12 | null | null | null | Acylation | OtherReaction | 462f2ec62d81e992577a968a9b12fce9fe1090236ae6c9f8b084f1cedb24cddd | 5e9e0b01f8c9a1c10ac2bdfadca2d4bb3d9d0593654f2be0a33adb4d01012cf3 | c1ccc2[nH]ccc2c1 | Cl-C-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[#8:3]-[C;D1;H3:4].[OH;D1;+0:5]-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](:[c:10]):[#7;a:11]:[c:12]>>[C;D1;H3:4]-[#8:3]-[CH2;D2;+0:1]-[O;H0;D2;+0:2]-[C:13](=[O;H0;D1;+0:5])-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](:[c:10]):[#7;a:11]:[c:12] | 30 | [{"value": 30.0, "product": "C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)C(=O)OCOC)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 15 | HOUR | A solution of [2-(7-hydroxy-1H-indol-3-yl)-1,1-dimethyl-ethyl]-carbamic acid tert-butyl ester (609 mg, 2.0 mmol) is dissolved in dry dimethylformamide (30 ml) under a nitrogen atmosphere and treated with sodium hydride (84 mg, 2.1 mmol, 60% dispersion in oil) added portion-wise over a 10 minute period. The mixture is c... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | HCl | null | null | 15 | CC(C)(Cc1c[nH]c2c(O)cccc12)NC(=O)OC(C)(C)C.COC(=O)CCl>>COCOC(=O)c1cccc2c(CC(C)(C)NC(=O)OC(C)(C)C)c[nH]c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d6abe5dd3fb941639e55b4abc3d4079d | COCOC(=O)c1cccc2c(CC(C)(C)NC(=O)OC(C)(C)C)c[nH]c12.CS(N)(=O)=O>>CC(C)(Cc1c[nH]c2c(C(=O)OCNS(C)(=O)=O)cccc12)NC(=O)OC(C)(C)C | C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)C(=O)OCOC)(C)C)=O.CS(=O)(=O)N.C[Al](C)C>>C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)C(=O)OCNS(=O)(=O)C)(C)C)=O | CO[CH2:13][O:12][C:10]([c:9]1[c:8]2[nH:7][cH:6][c:5]([CH2:4][C:2]([CH3:1])([CH3:3])[NH:23][C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30])[c:22]2[cH:21][cH:20][cH:19]1)=[O:11].[NH2:14][S:15]([CH3:16])(=[O:17])=[O:18]>>[CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][nH:7][c:8]2[c:9]([C:10](=[O:11])[O:12][CH2:13][NH:14... | COCOC(=O)c1cccc2c(CC(C)(C)NC(=O)OC(C)(C)C)c[nH]c12.CS(N)(=O)=O | CC(C)(Cc1c[nH]c2c(C(=O)OCNS(C)(=O)=O)cccc12)NC(=O)OC(C)(C)C | null | null | ClCCl | Heteroatom Alkylation and Arylation | OtherReaction | 27d6bcdad0878087216dc40eea1f1f35fccd29dfa60fe8ed3aa664fae6aef29b | 0d14747908d603e8fc04aed79bbcb75d879874eb9fb49385d2afe908ed402dd8 | c1ccc2[nH]ccc2c1 | C-O-[CH2;D2;+0:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6]:[#7;a:7].[C;D1;H3:8]-[#16:9](-[NH2;D1;+0:10])(=[O;D1;H0:11])=[O;D1;H0:12]>>[#7;a:7]:[c:6]:[c:5]-[C:3](=[O;D1;H0:4])-[#8:2]-[CH2;D2;+0:1]-[NH;D2;+0:10]-[#16:9](-[C;D1;H3:8])(=[O;D1;H0:11])=[O;D1;H0:12] | 117.8 | [{"value": 90.0, "product": "C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)C(=O)OCNS(=O)(=O)C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 117.8, "product": "C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)C(=O)OCNS(=O)(=O)C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of methanesulfonamide (106 mg, 1.12 mmol) and trimethyl aluminum (2.0 M in hexanes, 0.56 ml, 1.12 mmol) in dry dichloromethane (5.0 ml) is stirred at room temperature under a nitrogen atmosphere for 20 minutes. A solution of [2-(7-(methoxycarbomethoxy)-1H-indol-3-yl)-1,1-dimethyl-ethyl]-carbamic acid tert-bu... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Ester.Ether | Sulfonamide.Ester | null | null | c1ccc2[nH]ccc2c1 | HO- | ClCCl | null | null | COCOC(=O)c1cccc2c(CC(C)(C)NC(=O)OC(C)(C)C)c[nH]c12.CS(N)(=O)=O>ClCCl>CC(C)(Cc1c[nH]c2c(C(=O)OCNS(C)(=O)=O)cccc12)NC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e00e490317614dde964f7b2a9f8b6a90 | C=Cc1ccc(C#N)cc1.CC(C)(Cc1c[nH]c2c(CS(=O)(=O)C(F)(F)F)cccc12)NC(=O)OC(C)(C)C>>CC(C)(Cc1c[nH]c2c(C=Cc3ccc(C#N)cc3)cccc12)NC(=O)OC(C)(C)C | C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)CS(=O)(=O)C(F)(F)F)(C)C)=O.C(#N)C1=CC=C(C=C)C=C1>>C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)C=CC1=CC=C(C=C1)C#N)(C)C)=O | C=[CH:11][c:12]1[cH:13][cH:14][c:15]([C:16]#[N:17])[cH:18][cH:19]1.O=S(=O)(C(F)(F)F)[CH2:10][c:9]1[c:8]2[nH:7][cH:6][c:5]([CH2:4][C:2]([CH3:1])([CH3:3])[NH:24][C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[c:23]2[cH:22][cH:21][cH:20]1>>[CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][nH:7][c:8]2[c:9]([CH:10]=[CH:11]... | C=Cc1ccc(C#N)cc1.CC(C)(Cc1c[nH]c2c(CS(=O)(=O)C(F)(F)F)cccc12)NC(=O)OC(C)(C)C | CC(C)(Cc1c[nH]c2c(C=Cc3ccc(C#N)cc3)cccc12)NC(=O)OC(C)(C)C | null | null | null | C-C Coupling | OtherReaction | be72368e485bae2cf3a6c9f3c288e958fb19cb924e46b869d59552ae07869be9 | 9a367fc6597a2c2d2ef687b5d530f141dc98e4ffcb30f47f73afa833e2c55025 | C(=Cc1cccc2cc[nH]c12)c1ccccc1 | C=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].F-C(-F)(-F)-S(=O)(=O)-[CH2;D2;+0:5]-[c:6](:[c:7]):[c:8](:[c:9]):[#7;a:10]:[c:11]>>[c:3]:[c:2](-[CH;D2;+0:1]=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8](:[c:9]):[#7;a:10]:[c:11]):[c:4] | null | [] | null | null | null | null | (2-{7-[2-(4-Cyano-phenyl)-vinyl]-1H-indol-3-yl}-1,1-dimethyl-ethyl)-carbamic acid tert-butyl ester is prepared from [1,1-dimethyl-2-(7-trifluoromethanesulfonylmethyl-1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester and 4-cyanostyrene as described for the preparation of Amine 23 (93%). FDMS m/e=315.2 (M++1).
Conditi... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Sulfone.Vinyl | null | null | null | c1ccccc1.c1ccc2[nH]ccc2c1 | HF | null | null | null | C=Cc1ccc(C#N)cc1.CC(C)(Cc1c[nH]c2c(CS(=O)(=O)C(F)(F)F)cccc12)NC(=O)OC(C)(C)C>>CC(C)(Cc1c[nH]c2c(C=Cc3ccc(C#N)cc3)cccc12)NC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-91930206a1db4b719ea533076ef50a06 | C=Cc1cnccn1.CC(C)(Cc1c[nH]c2c(CS(=O)(=O)C(F)(F)F)cccc12)NC(=O)OC(C)(C)C>>CC(C)(Cc1c[nH]c2c(C=Cc3cnccn3)cccc12)NC(=O)OC(C)(C)C | C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)CS(=O)(=O)C(F)(F)F)(C)C)=O.C(=C)C1=NC=CN=C1>>C(C)(C)(C)OC(NC(CC1=CNC2=C(C=CC=C12)C=CC1=NC=CN=C1)(C)C)=O | [CH2:10]=[CH:11][c:12]1[cH:13][n:14][cH:15][cH:16][n:17]1.O=S(=O)(C[c:9]1[c:8]2[nH:7][cH:6][c:5]([CH2:4][C:2]([CH3:1])([CH3:3])[NH:22][C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[c:21]2[cH:20][cH:19][cH:18]1)C(F)(F)F>>[CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][nH:7][c:8]2[c:9]([CH:10]=[CH:11][c:12]3[cH:13][n... | C=Cc1cnccn1.CC(C)(Cc1c[nH]c2c(CS(=O)(=O)C(F)(F)F)cccc12)NC(=O)OC(C)(C)C | CC(C)(Cc1c[nH]c2c(C=Cc3cnccn3)cccc12)NC(=O)OC(C)(C)C | null | null | null | C-C Coupling | OtherReaction | 9ee5c848b3529c0571d068ce5ea5cd4d1d3705da2182d3214d2c9187dbcdd8d9 | 9a367fc6597a2c2d2ef687b5d530f141dc98e4ffcb30f47f73afa833e2c55025 | C(=Cc1cccc2cc[nH]c12)c1cnccn1 | F-C(-F)(-F)-S(=O)(=O)-C-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7].[#7;a:8]:[c:9]:[c:10](-[C:11]=[CH2;D1;+0:12]):[#7;a:13]>>[#7;a:8]:[c:9]:[c:10](-[C:11]=[CH;D2;+0:12]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]):[#7;a:13] | null | [] | null | null | null | null | {1,1-Dimethyl-2-[7-(2-pyrazin-2-yl-vinyl)-1H-indol-3-yl]-ethyl}-carbamic acid tert-butyl ester is prepared from [1,1-dimethyl-2-(7-trifluoromethanesulfonylmethyl-1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester and 2-vinylpyrazine as described for the preparation of Amine 23 (99%). FDMS m/e=393.2 (M++1)
Conditions:... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Sulfone.Vinyl | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1cnccn1.c1ccc2[nH]ccc2c1 | HF | null | null | null | C=Cc1cnccn1.CC(C)(Cc1c[nH]c2c(CS(=O)(=O)C(F)(F)F)cccc12)NC(=O)OC(C)(C)C>>CC(C)(Cc1c[nH]c2c(C=Cc3cnccn3)cccc12)NC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8866daba5bfc47cba6e2aaa9a9e6d8c6 | CN(C)Cc1c[nH]c2c([N+](=O)[O-])cccc12.COS(=O)(=O)OC>>CC(C)(Cc1c[nH]c2c([N+](=O)[O-])cccc12)[N+](=O)[O-] | CN(C)CC1=CNC2=C1C=CC=C2[N+](=O)[O-].COS(=O)(=O)OC.C[O-].[Na+]>>[N+](=O)([O-])C(CC1=CNC2=C(C=CC=C12)[N+](=O)[O-])(C)C | [CH3:2][N:17]([CH3:3])[CH2:4][c:5]1[cH:6][nH:7][c:8]2[c:9]([N+:10](=[O:11])[O-:12])[cH:13][cH:14][cH:15][c:16]12.COS(=O)(=[O:18])[O:19][CH3:1]>>[CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][nH:7][c:8]2[c:9]([N+:10](=[O:11])[O-:12])[cH:13][cH:14][cH:15][c:16]12)[N+:17](=[O:18])[O-:19] | CN(C)Cc1c[nH]c2c([N+](=O)[O-])cccc12.COS(=O)(=O)OC | CC(C)(Cc1c[nH]c2c([N+](=O)[O-])cccc12)[N+](=O)[O-] | null | null | CO.[N+](=O)([O-])C(C)C | Functional Group Addition | OtherReaction | 5bd93d2f1982c88e84b5fc5292e57c4ade933d319b1c969f1bcf720de5d2b688 | bfdf996aa8a01161a3995460dbc607f36b6b31262f523474e587d94418778376 | c1ccc2[nH]ccc2c1 | C-O-S(=O)(=[O;H0;D1;+0:1])-[O;H0;D2;+0:2]-[CH3;D1;+0:3].[CH3;D1;+0:4]-[N;H0;D3;+0:5](-[CH3;D1;+0:6])-[CH2;D2;+0:7]-[c:8]1:[c:9]:[c:10]:[#7;a:11]:[c:12]:1>>[CH3;D1;+0:3]-[C;H0;D4;+0:4](-[CH3;D1;+0:6])(-[CH2;D2;+0:7]-[c:8]1:[c:9]:[c:10]:[#7;a:11]:[c:12]:1)-[N+;H0;D3:5](-[O-;H0;D1:2])=[O;H0;D1;+0:1] | 131 | [{"value": 69.0, "product": "[N+](=O)([O-])C(CC1=CNC2=C(C=CC=C12)[N+](=O)[O-])(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 131.0, "product": "[N+](=O)([O-])C(CC1=CNC2=C(C=CC=C12)[N+](=O)[O-])(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | The 7-nitrogramine salt (2.0 g, 5.8 mmol) is suspended in a mixture of 2-nitropropane (9.5 mL) and methanol (9.5 mL). Dimethylsulfate (1.09 mL, 11.5 mmol) is added dropwise via syringe, and the resulting yellow solution is stirred at room temperature for 5 minutes. Sodium methoxide (0.62 g, 11.5 mmol) is then added in ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Nitro group | null | null | c1ccc2[nH]ccc2c1 | HO- | CO.[N+](=O)([O-])C(C)C | null | 0.083333 | CN(C)Cc1c[nH]c2c([N+](=O)[O-])cccc12.COS(=O)(=O)OC>CO.[N+](=O)([O-])C(C)C>CC(C)(Cc1c[nH]c2c([N+](=O)[O-])cccc12)[N+](=O)[O-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fcc97bd77b3c4880aa5eed15a29d7d18 | CC(C)(Cc1c[nH]c2c([N+](=O)[O-])cccc12)[N+](=O)[O-].O=S(=O)(Cl)c1ccccc1>>CC(C)(Cc1c[nH]c2c(NS(=O)(=O)c3ccccc3)cccc12)[N+](=O)[O-] | [N+](=O)([O-])C(CC1=CNC2=C(C=CC=C12)[N+](=O)[O-])(C)C.[N+](=O)([O-])C(CC1=CNC2=C(C=CC=C12)[N+](=O)[O-])(C)C.C1(=CC=CC=C1)S(=O)(=O)Cl>>[N+](=O)([O-])C(CC1=CNC2=C(C=CC=C12)NS(=O)(=O)C1=CC=CC=C1)(C)C | O=[N+:10]([O-])[c:9]1[c:8]2[nH:7][cH:6][c:5]([CH2:4][C:2]([CH3:1])([CH3:3])[N+:24](=[O:25])[O-:26])[c:23]2[cH:22][cH:21][cH:20]1.Cl[S:11](=[O:12])(=[O:13])[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][nH:7][c:8]2[c:9]([NH:10][S:11](=[O:12])(=[O:13])[c:14]3[cH:15][cH:16][cH:17][c... | CC(C)(Cc1c[nH]c2c([N+](=O)[O-])cccc12)[N+](=O)[O-].O=S(=O)(Cl)c1ccccc1 | CC(C)(Cc1c[nH]c2c(NS(=O)(=O)c3ccccc3)cccc12)[N+](=O)[O-] | null | [Pd] | C(C)(=O)OCC.N1=CC=CC=C1 | Acylation | OtherReaction | 6d82f556414835bcf6b9f0bce649a05d5bc17ae300992ec18a68cb9f62c221e6 | 8cfa256053695afc670cfb6cc03c2a6ebab576dbef684fdcb26ee84d655f5de5 | O=S(=O)(Nc1cccc2cc[nH]c12)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].O=[N+;H0;D3:7](-[O-])-[c:8](:[c:9]):[c:10](:[c:11]):[#7;a:12]:[c:13]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10](:[c:11]):[#7;a:12]:[c:13])-[c:4](:[c:5]):[c:6] | 71 | [{"value": 71.0, "product": "[N+](=O)([O-])C(CC1=CNC2=C(C=CC=C12)NS(=O)(=O)C1=CC=CC=C1)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | 3-(2-Nitro-2-methylpropyl)-7-nitroindole (1.89 g, 7.2 mmol) is dissolved in ethyl acetate (75 mL) and 10% Pd/C is added (750 mg). The mixture is stirred under a balloon of nitrogen for 2–3 hours. The mixture is filtered to remove the Pd/C, and the filtrate is evaporated to give a crude oil. This crude 3-(2-nitro-2-meth... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccc2[nH]ccc2c1 | Other | [Pd].C(C)(=O)OCC.N1=CC=CC=C1 | 0 | null | CC(C)(Cc1c[nH]c2c([N+](=O)[O-])cccc12)[N+](=O)[O-].O=S(=O)(Cl)c1ccccc1>[Pd].C(C)(=O)OCC.N1=CC=CC=C1>CC(C)(Cc1c[nH]c2c(NS(=O)(=O)c3ccccc3)cccc12)[N+](=O)[O-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-408263d2ae6444428752aab62ae17bb3 | CCOC(=O)CCCCN(CCc1cc(F)ccc1OC)Cc1ccc(C(=O)OC)cc1>>COC(=O)CCCCN(CCc1cc(F)ccc1O)Cc1ccc(C(=O)OC)cc1 | CO.B(Br)(Br)Br.C(C)OC(CCCCN(CCC1=C(C=CC(=C1)F)OC)CC1=CC=C(C(=O)OC)C=C1)=O>>COC(CCCCN(CCC1=C(C=CC(=C1)F)O)CC1=CC=C(C(=O)OC)C=C1)=O | C[CH2:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][CH2:8][N:9]([CH2:10][CH2:11][c:12]1[cH:13][c:14]([F:15])[cH:16][cH:17][c:18]1[O:19]C)[CH2:20][c:21]1[cH:22][cH:23][c:24]([C:25](=[O:26])[O:27][CH3:28])[cH:29][cH:30]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][CH2:8][N:9]([CH2:10][CH2:11][c:12]1[cH:13][c:14]([F:15])[... | CCOC(=O)CCCCN(CCc1cc(F)ccc1OC)Cc1ccc(C(=O)OC)cc1 | COC(=O)CCCCN(CCc1cc(F)ccc1O)Cc1ccc(C(=O)OC)cc1 | null | null | ClCCl | Deprotection | OtherReaction | f59b8116b9a9ca99fb99fbc349fd2f3ba7a407b5d14f87b4825067d0befd0c68 | e00f9a9e80835d92a5562f8e4d77c15ee40726b40cd6dcf858e9b9fabcbd50cd | c1ccc(CCNCc2ccccc2)cc1 | C-[CH2;D2;+0:1]-[#8:2]-[C:3](-[C:4])=[O;D1;H0:5].C-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C:4]-[C:3](=[O;D1;H0:5])-[#8:2]-[CH3;D1;+0:1].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9] | null | [] | 0 | CELSIUS | 1 | HOUR | 2.6 g (5.84 mmol) of methyl 4-({(5-ethoxy-5-oxopentyl)[2-(5-fluoro-2-methoxy-phenyl)ethyl]amino}methyl)benzoate are dissolved in 50 ml of dichloromethane, the mixture is cooled to 0° C., and 19.3 ml (19.3 mmol) of a 1N solution of boron tribromide in dichloromethane are added dropwise. The solution is stirred at 0° C. ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether | Ester.Aromatic alcohol | null | null | c1ccccc1.c1ccccc1 | Other | ClCCl | 0 | 1 | CCOC(=O)CCCCN(CCc1cc(F)ccc1OC)Cc1ccc(C(=O)OC)cc1>ClCCl>COC(=O)CCCCN(CCc1cc(F)ccc1O)Cc1ccc(C(=O)OC)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-04c146a1b0024307add260bad868c423 | COC(=O)CCCCN(CCc1ccccc1OCc1ccccc1Cl)Cc1ccc(C(=O)OC)cc1>>O=C(O)CCCCN(CCc1ccccc1OCc1ccccc1Cl)Cc1ccc(C(=O)O)cc1 | ClC1=C(COC2=C(CCN(CCCCC(=O)OC)CC3=CC=C(C(=O)OC)C=C3)C=CC=C2)C=CC=C1.O.[OH-].[Na+]>>C(=O)(O)CCCCN(CCC1=C(C=CC=C1)OCC1=C(C=CC=C1)Cl)CC1=CC=C(C(=O)O)C=C1 | C[O:3][C:2](=[O:1])[CH2:4][CH2:5][CH2:6][CH2:7][N:8]([CH2:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[O:17][CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][c:24]1[Cl:25])[CH2:26][c:27]1[cH:28][cH:29][c:30]([C:31](=[O:32])[O:33]C)[cH:34][cH:35]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][CH2:7][N:8]([CH2:9][CH2:10][c... | COC(=O)CCCCN(CCc1ccccc1OCc1ccccc1Cl)Cc1ccc(C(=O)OC)cc1 | O=C(O)CCCCN(CCc1ccccc1OCc1ccccc1Cl)Cc1ccc(C(=O)O)cc1 | null | null | CO | Deprotection | OtherReaction | 6e62db7aac546f574bcfb83067ba8906c30fcbfedfc37aa16b5eaad33833f45a | ed5fed81ba501ef41c88831ec6b9463b899bfdd0815c4145ae51c79addb226d0 | c1ccc(CNCCc2ccccc2OCc2ccccc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].C-[O;H0;D2;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1].[O;D1;H0:7]=[C:6](-[OH;D1;+0:5])-[c:8] | null | [] | 60 | CELSIUS | 1 | HOUR | 124.8 mg (0.238 mmol) of methyl 4-{[{2-[(2-chlorobenzyl)-oxy]phenethyl}(5-methoxy-5-oxopentyl)amino]methyl}benzoate from Ex. 1 are initially charged in 0.3 ml of methanol and 0.17 ml of water and admixed with 0.2 ml of a 40% strength sodium hydroxide solution. The mixture is stirred at 60° C. for one hour and then cool... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Carboxylic acid.Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | Other | CO | 60 | 1 | COC(=O)CCCCN(CCc1ccccc1OCc1ccccc1Cl)Cc1ccc(C(=O)OC)cc1>CO>O=C(O)CCCCN(CCc1ccccc1OCc1ccccc1Cl)Cc1ccc(C(=O)O)cc1 |
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