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-6a8735cfe0b441e5882e8c6813881531 | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(C)(C)OC>>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | C1(=CC=C(C=C1)S(=O)(=O)O)C.C(C)(C)(C)OC(CC(C[C@@H](COC(C1=CC=CC=C1)=O)O)O)=O.COC(C)(C)OC.CC(=O)C>>C(C)(C)(C)OC(C[C@@H]1OC(O[C@@H](C1)COC(C1=CC=CC=C1)=O)(C)C)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][CH:9]([CH2:10][C@@H:11]([CH2:12][O:13][C:14](=[O:15])[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[OH:22])[OH:26].CO[C:23](OC)([CH3:24])[CH3:25]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@H:9]1[CH2:10][C@@H:11]([CH2:12][O:13][C:14](=[O:15])[c:16]2[c... | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(C)(C)OC | CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | null | null | O.C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 1b897a1df0e5845a2b8f88001414f79fb5194fee7b162720b2a7cd50dadd1aa0 | 5b3ed0191ba86b6e1048e761d184b2389fdc2075f66c7c9aaba67c74a6cbc43e | O=C(OC[C@@H]1CCOCO1)c1ccccc1 | C-O-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-O-C.[C:4]-[C:5](-[OH;D1;+0:6])-[C:7]-[CH;D3;+0:8](-[OH;D1;+0:9])-[C:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[C;D1;H3:17]>>[C:4]-[C:5]1-[C:7]-[C@H;D3;+0:8](-[C:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[C;D1;H3:17]... | null | [] | null | null | null | null | To a solution composed of 108 mg (90.2 weight %, 0.3 mmol) of the (5S)-6-benzoyloxy-3,5-dihydroxyhexanoic tert-butyl ester produced in Example 15, 62.4 mg (0.6 mmol) of 2,2-dimethoxypropane, and 5 mL of acetone were added 5.7 mg (0.03 mmol) of p-toluenesulfonic acid.1H2O and 18.3 mg (0.15 mmol) of N,N-dimethylaminopyri... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Secondary alcohol.Secondary alcohol | Ether.Ether | null | C1COCOC1 | C1COCOC1.c1ccccc1 | HO- | O.C(C)#N | null | null | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(C)(C)OC>O.C(C)#N>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2f1c3474b4ba4cc1991d325c445917b5 | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1>>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | C(C)(C)(C)OC(CC(C[C@@H](COC(C1=CC=CC=C1)=O)O)O)=O.O[C@@H]1C[C@H](OC(C1)=O)COC(C1=CC=CC=C1)=O.COC(C[C@@H]1OC(O[C@@H](C1)COC(C1=CC=CC=C1)=O)(C)C)=O>>C(C)(C)(C)OC(C[C@@H]1OC(O[C@@H](C1)COC(C1=CC=CC=C1)=O)(C)C)=O | O=C(OC[C@@H](O)CC(O)[CH2:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])c1ccccc1.COC(=O)C[C@H:9]1[CH2:10][C@@H:11]([CH2:12][O:13][C:14](=[O:15])[c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[O:22][C:23]([CH3:24])([CH3:25])[O:26]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@H:9]1[CH2:10][C@@H:11]([CH2:1... | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | null | null | null | C-C Coupling | OtherReaction | c60ef6ec5a2c9d314090af95d014b97611eb1c633b6c4edd79357c82b20f8fda | eae68fb503126ff52b24216efa23df03bfbd9669bc67803b9ac2cd9653b8c829 | O=C(OC[C@@H]1CCOCO1)c1ccccc1 | C-O-C(=O)-C-[C@@H;D3;+0:1]1-[#8:2]-[C:3]-[#8:4]-[C:5]-[C:6]-1.O-C(-C-[C@@H](-O)-C-O-C(=O)-c1:c:c:c:c:c:1)-[CH2;D2;+0:7]-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[C;D1;H3:14]>>[C;D1;H3:12]-[C:11](-[C;D1;H3:13])(-[C;D1;H3:14])-[#8:10]-[C:8](=[O;D1;H0:9])-[CH2;D2;+0:7]-[C@@H;D3;+0:1]1-[#8:2]-[C:3]-... | null | [] | null | null | null | null | 93.8%; (5S)-6-benzoyloxy-3,5-dihydroxyhexanoic tert-butyl ester: 2.3%; (2S,4R)-4-hydroxy-6-oxo-2-[(benzoyloxy)methyl]tetrahydro-2H-pyran: 0.1%; 2-[(4R,6S)-2,2-dimethyl-6-benzoyloxymethyl-1,3-dioxan-4-yl]acetic methyl ester: 0.1%.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester.Ether.Secondary alcohol.Secondary alcohol | Ester.Ether | c1ccccc1.C1COCOC1 | C1COCOC1 | C1COCOC1.c1ccccc1 | HO- | null | null | null | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1>>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-842a1339cfd14e34bb806023e6bbd3bc | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(C)(C)OC>>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | C(C)(C)(C)OC(CC(C[C@@H](COC(C1=CC=CC=C1)=O)O)O)=O.COC(C)(C)OC.CS(=O)(=O)O.N1=CC=CC=C1>>C(C)(C)(C)OC(C[C@@H]1OC(O[C@@H](C1)COC(C1=CC=CC=C1)=O)(C)C)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][CH:9]([CH2:10][C@@H:11]([CH2:12][O:13][C:14](=[O:15])[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[OH:22])[OH:26].CO[C:23](OC)([CH3:24])[CH3:25]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@H:9]1[CH2:10][C@@H:11]([CH2:12][O:13][C:14](=[O:15])[c:16]2[c... | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(C)(C)OC | CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | null | null | CC(=O)C.O.C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 1b897a1df0e5845a2b8f88001414f79fb5194fee7b162720b2a7cd50dadd1aa0 | 5b3ed0191ba86b6e1048e761d184b2389fdc2075f66c7c9aaba67c74a6cbc43e | O=C(OC[C@@H]1CCOCO1)c1ccccc1 | C-O-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-O-C.[C:4]-[C:5](-[OH;D1;+0:6])-[C:7]-[CH;D3;+0:8](-[OH;D1;+0:9])-[C:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[C;D1;H3:17]>>[C:4]-[C:5]1-[C:7]-[C@H;D3;+0:8](-[C:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[C;D1;H3:17]... | null | [] | 40 | CELSIUS | 16 | HOUR | To a solution composed of 108 mg (90.2 weight %, 0.3 mmol) of the (5S)-6-benzoyloxy-3,5-dihydroxyhexanoic tert-butyl ester produced in Example 15, 62.4 mg (0.6 mmol) of 2,2-dimethoxypropane, and 5 mL of acetone were added 3.0 mg (0.03 mmol) of methanesulfonic acid and 11.9 mg (0.15 mmol) of pyridine, and the mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Secondary alcohol.Secondary alcohol | Ether.Ether | null | C1COCOC1 | C1COCOC1.c1ccccc1 | HO- | CC(=O)C.O.C(C)#N | 40 | 16 | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(C)(C)OC>CC(=O)C.O.C(C)#N>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b307568494b64dc9a5aa21c4b10f2204 | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1>>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | C(C)(C)(C)OC(CC(C[C@@H](COC(C1=CC=CC=C1)=O)O)O)=O.O[C@@H]1C[C@H](OC(C1)=O)COC(C1=CC=CC=C1)=O.COC(C[C@@H]1OC(O[C@@H](C1)COC(C1=CC=CC=C1)=O)(C)C)=O>>C(C)(C)(C)OC(C[C@@H]1OC(O[C@@H](C1)COC(C1=CC=CC=C1)=O)(C)C)=O | O=C(OC[C@@H](O)CC(O)[CH2:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])c1ccccc1.COC(=O)C[C@H:9]1[CH2:10][C@@H:11]([CH2:12][O:13][C:14](=[O:15])[c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[O:22][C:23]([CH3:24])([CH3:25])[O:26]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@H:9]1[CH2:10][C@@H:11]([CH2:1... | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | null | null | null | C-C Coupling | OtherReaction | c60ef6ec5a2c9d314090af95d014b97611eb1c633b6c4edd79357c82b20f8fda | eae68fb503126ff52b24216efa23df03bfbd9669bc67803b9ac2cd9653b8c829 | O=C(OC[C@@H]1CCOCO1)c1ccccc1 | C-O-C(=O)-C-[C@@H;D3;+0:1]1-[#8:2]-[C:3]-[#8:4]-[C:5]-[C:6]-1.O-C(-C-[C@@H](-O)-C-O-C(=O)-c1:c:c:c:c:c:1)-[CH2;D2;+0:7]-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[C;D1;H3:14]>>[C;D1;H3:12]-[C:11](-[C;D1;H3:13])(-[C;D1;H3:14])-[#8:10]-[C:8](=[O;D1;H0:9])-[CH2;D2;+0:7]-[C@@H;D3;+0:1]1-[#8:2]-[C:3]-... | null | [] | null | null | null | null | 95.6%; (5S)-6-benzoyloxy-3,5-dihydroxyhexanoic tert-butyl ester: 2.6%; (2S,4R)-4-hydroxy-6-oxo-2-[(benzoyloxy)methyl]tetrahydro-2H-pyran: 0.1%; 2-[(4R,6S)-2,2-dimethyl-6-benzoyloxymethyl-1,3-dioxan-4-yl]acetic methyl ester: undetected.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester.Ether.Secondary alcohol.Secondary alcohol | Ester.Ether | c1ccccc1.C1COCOC1 | C1COCOC1 | C1COCOC1.c1ccccc1 | HO- | null | null | null | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1>>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-af60198c86d14e8eb98d5b4212b17099 | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(C)(C)OC>>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | C(C)(C)(C)OC(CC(C[C@@H](COC(C1=CC=CC=C1)=O)O)O)=O.COC(C)(C)OC.FC(C(=O)O)(F)F.N1=CC=CC=C1>>C(C)(C)(C)OC(C[C@@H]1OC(O[C@@H](C1)COC(C1=CC=CC=C1)=O)(C)C)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][CH:9]([CH2:10][C@@H:11]([CH2:12][O:13][C:14](=[O:15])[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[OH:22])[OH:26].CO[C:23](OC)([CH3:24])[CH3:25]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@H:9]1[CH2:10][C@@H:11]([CH2:12][O:13][C:14](=[O:15])[c:16]2[c... | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(C)(C)OC | CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | null | null | CC(=O)C.O.C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 1b897a1df0e5845a2b8f88001414f79fb5194fee7b162720b2a7cd50dadd1aa0 | 5b3ed0191ba86b6e1048e761d184b2389fdc2075f66c7c9aaba67c74a6cbc43e | O=C(OC[C@@H]1CCOCO1)c1ccccc1 | C-O-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-O-C.[C:4]-[C:5](-[OH;D1;+0:6])-[C:7]-[CH;D3;+0:8](-[OH;D1;+0:9])-[C:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[C;D1;H3:17]>>[C:4]-[C:5]1-[C:7]-[C@H;D3;+0:8](-[C:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[C;D1;H3:17]... | null | [] | 40 | CELSIUS | 16 | HOUR | To a solution composed of 108 mg (90.2 weight %, 0.3 mmol) of the (5S)-6-benzoyloxy-3,5-dihydroxyhexanoic tert-butyl ester produced in Example 15, 62.4 mg (0.6 mmol) of 2,2-dimethoxypropane, and 5 mL of acetone were added 3.5 mg (0.03 mmol) of trifluoroacetic acid and 11.9 mg (0.15 mmol) of pyridine, and the mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Secondary alcohol.Secondary alcohol | Ether.Ether | null | C1COCOC1 | C1COCOC1.c1ccccc1 | HO- | CC(=O)C.O.C(C)#N | 40 | 16 | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(C)(C)OC>CC(=O)C.O.C(C)#N>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3584b565af5c4626b6ea0b0253adc328 | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1>>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | C(C)(C)(C)OC(CC(C[C@@H](COC(C1=CC=CC=C1)=O)O)O)=O.O[C@@H]1C[C@H](OC(C1)=O)COC(C1=CC=CC=C1)=O.COC(C[C@@H]1OC(O[C@@H](C1)COC(C1=CC=CC=C1)=O)(C)C)=O>>C(C)(C)(C)OC(C[C@@H]1OC(O[C@@H](C1)COC(C1=CC=CC=C1)=O)(C)C)=O | O=C(OC[C@@H](O)CC(O)[CH2:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])c1ccccc1.COC(=O)C[C@H:9]1[CH2:10][C@@H:11]([CH2:12][O:13][C:14](=[O:15])[c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[O:22][C:23]([CH3:24])([CH3:25])[O:26]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@H:9]1[CH2:10][C@@H:11]([CH2:1... | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | null | null | null | C-C Coupling | OtherReaction | c60ef6ec5a2c9d314090af95d014b97611eb1c633b6c4edd79357c82b20f8fda | eae68fb503126ff52b24216efa23df03bfbd9669bc67803b9ac2cd9653b8c829 | O=C(OC[C@@H]1CCOCO1)c1ccccc1 | C-O-C(=O)-C-[C@@H;D3;+0:1]1-[#8:2]-[C:3]-[#8:4]-[C:5]-[C:6]-1.O-C(-C-[C@@H](-O)-C-O-C(=O)-c1:c:c:c:c:c:1)-[CH2;D2;+0:7]-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[C;D1;H3:14]>>[C;D1;H3:12]-[C:11](-[C;D1;H3:13])(-[C;D1;H3:14])-[#8:10]-[C:8](=[O;D1;H0:9])-[CH2;D2;+0:7]-[C@@H;D3;+0:1]1-[#8:2]-[C:3]-... | null | [] | null | null | null | null | 89.3%; (5S)-6-benzoyloxy-3,5-dihydroxyhexanoic tert-butyl ester: 8.8%; (2S,4R)-4-hydroxy-6-oxo-2-[(benzoyloxy)methyl]tetrahydro-2H-pyran: 0.1%; 2-[(4R,6S)-2,2-dimethyl-6-benzoyloxymethyl-1,3-dioxan-4-yl]acetic methyl ester: undetected.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester.Ether.Secondary alcohol.Secondary alcohol | Ester.Ether | c1ccccc1.C1COCOC1 | C1COCOC1 | C1COCOC1.c1ccccc1 | HO- | null | null | null | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1>>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-06e7d0dfa69f44efacf028ddf2b3de84 | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(C)(C)OC>>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | C(C)(C)(C)OC(CC(C[C@@H](COC(C1=CC=CC=C1)=O)O)O)=O.COC(C)(C)OC.S(O)(O)(=O)=O.N1=CC=CC=C1>>C(C)(C)(C)OC(C[C@@H]1OC(O[C@@H](C1)COC(C1=CC=CC=C1)=O)(C)C)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][CH:9]([CH2:10][C@@H:11]([CH2:12][O:13][C:14](=[O:15])[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[OH:22])[OH:26].CO[C:23](OC)([CH3:24])[CH3:25]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@H:9]1[CH2:10][C@@H:11]([CH2:12][O:13][C:14](=[O:15])[c:16]2[c... | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(C)(C)OC | CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | null | null | CC(=O)C.O.C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 1b897a1df0e5845a2b8f88001414f79fb5194fee7b162720b2a7cd50dadd1aa0 | 5b3ed0191ba86b6e1048e761d184b2389fdc2075f66c7c9aaba67c74a6cbc43e | O=C(OC[C@@H]1CCOCO1)c1ccccc1 | C-O-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-O-C.[C:4]-[C:5](-[OH;D1;+0:6])-[C:7]-[CH;D3;+0:8](-[OH;D1;+0:9])-[C:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[C;D1;H3:17]>>[C:4]-[C:5]1-[C:7]-[C@H;D3;+0:8](-[C:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[C;D1;H3:17]... | null | [] | 40 | CELSIUS | 16 | HOUR | To a solution composed of 108 mg (90.2 weight %, 0.3 mmol) of the (5S)-6-benzoyloxy-3,5-dihydroxyhexanoic tert-butyl ester produced in Example 15, 62.4 mg (0.6 mmol) of 2,2-dimethoxypropane, and 5 mL of acetone were added 1.5 mg (0.015 mmol) of sulfuric acid and 11.9 mg (0.15 mmol) of pyridine, and the mixture was stir... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Secondary alcohol.Secondary alcohol | Ether.Ether | null | C1COCOC1 | C1COCOC1.c1ccccc1 | HO- | CC(=O)C.O.C(C)#N | 40 | 16 | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(C)(C)OC>CC(=O)C.O.C(C)#N>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9fa8ff56438e4577881a0fa12dc465f5 | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1>>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | C(C)(C)(C)OC(CC(C[C@@H](COC(C1=CC=CC=C1)=O)O)O)=O.O[C@@H]1C[C@H](OC(C1)=O)COC(C1=CC=CC=C1)=O.COC(C[C@@H]1OC(O[C@@H](C1)COC(C1=CC=CC=C1)=O)(C)C)=O>>C(C)(C)(C)OC(C[C@@H]1OC(O[C@@H](C1)COC(C1=CC=CC=C1)=O)(C)C)=O | O=C(OC[C@@H](O)CC(O)[CH2:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])c1ccccc1.COC(=O)C[C@H:9]1[CH2:10][C@@H:11]([CH2:12][O:13][C:14](=[O:15])[c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[O:22][C:23]([CH3:24])([CH3:25])[O:26]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@H:9]1[CH2:10][C@@H:11]([CH2:1... | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | null | null | null | C-C Coupling | OtherReaction | c60ef6ec5a2c9d314090af95d014b97611eb1c633b6c4edd79357c82b20f8fda | eae68fb503126ff52b24216efa23df03bfbd9669bc67803b9ac2cd9653b8c829 | O=C(OC[C@@H]1CCOCO1)c1ccccc1 | C-O-C(=O)-C-[C@@H;D3;+0:1]1-[#8:2]-[C:3]-[#8:4]-[C:5]-[C:6]-1.O-C(-C-[C@@H](-O)-C-O-C(=O)-c1:c:c:c:c:c:1)-[CH2;D2;+0:7]-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[C;D1;H3:14]>>[C;D1;H3:12]-[C:11](-[C;D1;H3:13])(-[C;D1;H3:14])-[#8:10]-[C:8](=[O;D1;H0:9])-[CH2;D2;+0:7]-[C@@H;D3;+0:1]1-[#8:2]-[C:3]-... | null | [] | null | null | null | null | 95.8%; (5S)-6-benzoyloxy-3,5-dihydroxyhexanoic tert-butyl ester: 2.3%; (2S,4R)-4-hydroxy-6-oxo-2-[(benzoyloxy)methyl]tetrahydro-2H-pyran: 0.1%; 2-[(4R,6S)-2,2-dimethyl-6-benzoyloxymethyl-1,3-dioxan-4-yl]acetic methyl ester: undetected.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester.Ether.Secondary alcohol.Secondary alcohol | Ester.Ether | c1ccccc1.C1COCOC1 | C1COCOC1 | C1COCOC1.c1ccccc1 | HO- | null | null | null | CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1.COC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1>>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-389c090c27624350a290a2665c8d5ee1 | CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1>>CC(C)(C)OC(=O)C[C@H]1C[C@@H](CO)OC(C)(C)O1 | Cl.C(C)(C)(C)OC(C[C@@H]1OC(O[C@@H](C1)COC(C1=CC=CC=C1)=O)(C)C)=O.[OH-].[Na+]>>C(C)(C)(C)OC(C[C@@H]1OC(O[C@@H](C1)CO)(C)C)=O | O=C(c1ccccc1)[O:13][CH2:12][C@@H:11]1[CH2:10][C@H:9]([CH2:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[O:18][C:15]([CH3:16])([CH3:17])[O:14]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@H:9]1[CH2:10][C@@H:11]([CH2:12][OH:13])[O:14][C:15]([CH3:16])([CH3:17])[O:18]1 | CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1 | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CO)OC(C)(C)O1 | null | null | CO | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | 8df1b5c4ec88eb8f4e334a9ade2ac7fc0b3f460ea1450816d1758f28eee39662 | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | C1COCOC1 | O=C(-[O;H0;D2;+0:1]-[C:2]-[C:3]-[#8:4])-c1:c:c:c:c:c:1>>[#8:4]-[C:3]-[C:2]-[OH;D1;+0:1] | 90 | [{"value": 90.0, "product": "C(C)(C)(C)OC(C[C@@H]1OC(O[C@@H](C1)CO)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.9, "product": "C(C)(C)(C)OC(C[C@@H]1OC(O[C@@H](C1)CO)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 3.64 g (10 mmol) of the 2-[(4R,6S)-2,2-dimethyl-6-benzoyloxymethyl-1,3-dioxan-4-yl]acetic tert-butyl ester produced in Example 26 in methanol (36 mL) was added 10 mL of 1N-aqueous sodium hydroxide solution, and the mixture was stirred at room temperature for 2 hours. This reaction mixture was adjusted ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | c1ccccc1 | null | C1COCOC1 | HO- | CO | null | 2 | CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1>CO>CC(C)(C)OC(=O)C[C@H]1C[C@@H](CO)OC(C)(C)O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a17440283c1b4d1dba9b75e78b2c71b4 | C1=CCCC=C1.Nc1ccccc1C(=O)O>>C1=CC2CCC1c1ccccc12 | C1=CC=CCC1.N(=O)OCCC(C)C.C(C=1C(N)=CC=CC1)(=O)O>>C12C=CC(C3=CC=CC=C13)CC2 | [CH:1]1=[CH:2][CH2:3][CH2:4][CH:5]=[CH:6]1.N[c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1C(=O)O>>[CH:1]1=[CH:2][CH:3]2[CH2:4][CH2:5][CH:6]1[c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]12 | C1=CCCC=C1.Nc1ccccc1C(=O)O | C1=CC2CCC1c1ccccc12 | null | null | C1CCOC1.O1CCCC1 | C-C Coupling | OtherReaction | c436194b1c8227929bbf7f16436d92969a89b4321aa58c61ab8425418848a47c | a4c01075b673bec477fd25a5b02cc9f473ba892f0292fd69391e3bb751d918ff | C1=CC2CCC1c1ccccc12 | N-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]:[c;H0;D3;+0:6]:1-C(-O)=O.[C:7]1=[C:8]-[CH2;D2;+0:9]-[C:10]-[CH;D2;+0:11]=[CH;D2;+0:12]-1>>[C:7]1=[C:8]-[CH;D3;+0:9]2-[C:10]-[CH2;D2;+0:11]-[CH;D3;+0:12]-1-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]:[c;H0;D3;+0:6]:1-2 | 78 | [{"value": 78.0, "product": "C12C=CC(C3=CC=CC=C13)CC2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A THF solution of 1 g (7.3 mmol) of anthranilic acid was dropped into a mixed solution under reflux of 0.77 ml (8.0 mmol) of 1,3-cyclohexadiene, 1.1 ml of isoamyl nitrite and 50 ml of tetrahydrofuran. Then, the resultant solution was heated and refluxed for 2 hours to remove THF, extracted with chloroform, washed with ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine.Conjugated diene | null | C1=CCCC=C1.c1ccccc1 | C1=CC2CCC1c1ccccc12 | C1=CC2CCC1c1ccccc12 | HO- | C1CCOC1.O1CCCC1 | null | null | C1=CCCC=C1.Nc1ccccc1C(=O)O>C1CCOC1.O1CCCC1>C1=CC2CCC1c1ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-30dde6a9126b43dba9aa60452e83156e | O=S(=O)(c1ccccc1)C1C2CCC(c3ccccc32)C1Cl>>O=S(=O)(C1=CC2CCC1c1ccccc12)c1ccccc1 | ClC1C2C3=CC=CC=C3C(C1S(=O)(=O)C1=CC=CC=C1)CC2.C1CCC2=NCCCN2CC1.Cl>>C1(=CC=CC=C1)S(=O)(=O)C=1C2C3=CC=CC=C3C(C1)CC2 | Cl[CH:5]1[CH:4]([S:2](=[O:1])(=[O:3])[c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[CH:9]2[CH2:8][CH2:7][CH:6]1[c:15]1[c:10]2[cH:11][cH:12][cH:13][cH:14]1>>[O:1]=[S:2](=[O:3])([C:4]1=[CH:5][CH:6]2[CH2:7][CH2:8][CH:9]1[c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]12)[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | O=S(=O)(c1ccccc1)C1C2CCC(c3ccccc32)C1Cl | O=S(=O)(C1=CC2CCC1c1ccccc12)c1ccccc1 | null | null | C1CCOC1 | Functional Group Interconversion | OtherReaction | 0ec480e558dbe5d386322cb1b1e761f3140589554c2f9eefabaa0916e4e064c8 | 6e8d13230370538f865fe4c85906dd6cad07c6cb5b152c1d96823b885b960ee6 | O=S(=O)(C1=CC2CCC1c1ccccc12)c1ccccc1 | Cl-[CH;D3;+0:1]1-[C:2]2-[C:3]-[C:4]-[C:5](-[c:6]:[c:7]-2)-[CH;D3;+0:8]-1-[#16:9](=[O;D1;H0:10])(=[O;D1;H0:11])-[c:12]>>[O;D1;H0:10]=[#16:9](=[O;D1;H0:11])(-[c:12])-[C;H0;D3;+0:8]1=[CH;D2;+0:1]-[C:2]2-[C:3]-[C:4]-[C:5]-1-[c:6]:[c:7]-2 | 98 | [{"value": 98.0, "product": "C1(=CC=CC=C1)S(=O)(=O)C=1C2C3=CC=CC=C3C(C1)CC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.8, "product": "C1(=CC=CC=C1)S(=O)(=O)C=1C2C3=CC=CC=C3C(C1)CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A solution of 0.3 g (0.91 mmol) of the obtained 2-chloro-1,2,3,4-tetrahydro-3-phenylsulfonyl-1,4-ethanonaphthalene and 15 ml of anhydrous THF was cooled to 0° C., added with 2.5 ml of 1,8-diazabicyclo[5.4.0]-7-undecene and stirred for 30 minutes. The solution is then added with a dilute hydrochloric acid solution, extr... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide | null | c1ccc2c(c1)C1CCC2CC1 | C1=CC2CCC1c1ccccc12 | c1ccccc1.C1=CC2CCC1c1ccccc12 | HCl | C1CCOC1 | null | 0.5 | O=S(=O)(c1ccccc1)C1C2CCC(c3ccccc32)C1Cl>C1CCOC1>O=S(=O)(C1=CC2CCC1c1ccccc12)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-98a2d165b8174d258df596d366a29224 | O=S(=O)(C1=CC2CCC1c1ccccc12)c1ccccc1.[C-]#[N+]CC(=O)OCC>>CCOC(=O)c1[nH]cc2c1C1CCC2c2ccccc21 | C1(=CC=CC=C1)S(=O)(=O)C=1C2C3=CC=CC=C3C(C1)CC2.[N+](#[C-])CC(=O)OCC.Cl.C(C)(C)(C)O[K]>>C(C)OC(=O)C=1NC=C2C3C4=C(C(C12)CC3)C=CC=C4 | O=S(=O)(c1ccccc1)[C:9]1=[CH:10][CH:11]2[CH2:12][CH2:13][CH:14]1[c:15]1[cH:16][cH:17][cH:18][cH:19][c:20]12.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][N+:7]#[C-:8]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[nH:7][cH:8][c:9]2[c:10]1[CH:11]1[CH2:12][CH2:13][CH:14]2[c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]21 | O=S(=O)(C1=CC2CCC1c1ccccc12)c1ccccc1.[C-]#[N+]CC(=O)OCC | CCOC(=O)c1[nH]cc2c1C1CCC2c2ccccc21 | null | null | C1CCOC1 | Functional Group Interconversion | OtherReaction | 2e0499679c8bf90458b0a8fb27cfc6846c73925e7a0b85b33ab8812db7639ffc | f96f48572a9311e1374d59fed69106a7c06d9a122148af1884a54fbc5f2d4830 | c1ccc2c(c1)C1CCC2c2c[nH]cc21 | O=S(=O)(-[C;H0;D3;+0:1]1=[CH;D2;+0:2]-[C:3]2-[C:4]-[C:5]-[C:6]-1-[c:7]:[c:8]-2)-c1:c:c:c:c:c:1.[C-;H0;D1:9]#[N+;H0;D2:10]-[CH2;D2;+0:11]-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15]>>[C:15]-[#8:14]-[C:12](=[O;D1;H0:13])-[c;H0;D3;+0:11]1:[nH;D2;+0:10]:[cH;D2;+0:9]:[c;H0;D3;+0:1]2:[c;H0;D3;+0:2]:1-[C:3]1-[C:4]-[C:5]-[C:6]-2-[c:7... | 91 | [{"value": 91.0, "product": "C(C)OC(=O)C=1NC=C2C3C4=C(C(C12)CC3)C=CC=C4", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.9, "product": "C(C)OC(=O)C=1NC=C2C3C4=C(C(C12)CC3)C=CC=C4", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | Under an argon atmosphere, 0.296 g (1.0 mmol) of the obtained 1,4-dihydro-2-phenylsulfonyl-1,4-ethanonaphthalene, 0.13 ml (1.15 mmol) of ethyl isocyano-acetate and 30 ml of anhydrous THF were charged and cooled to 0° C. Into the mixture, 1.7 ml of tert-BuOK (1 M THF solution) was dropped over two hours and the resultan... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Isocyanide.Sulfone | Ester | c1ccccc1.C1=CC2CCC1c1ccccc12 | c1ccc2c(c1)C1CCC2c2c[nH]cc21 | c1ccc2c(c1)C1CCC2c2c[nH]cc21 | HO- | C1CCOC1 | 0 | null | O=S(=O)(C1=CC2CCC1c1ccccc12)c1ccccc1.[C-]#[N+]CC(=O)OCC>C1CCOC1>CCOC(=O)c1[nH]cc2c1C1CCC2c2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6cea0494348b410e84f555c127ac38a6 | Oc1cccc(C(F)(F)F)c1.[CH3][Zr]([CH3])[CH]1C=CC=C1>>FC(F)(F)c1cccc([O][Zr]([O]c2cccc(C(F)(F)F)c2)[CH]2C=CC=C2)c1 | C1(C=CC=C1)[Zr](C)C.FC(C1=CC(=CC=C1)O)(F)F>>C1(C=CC=C1)[Zr](OC1=CC(=CC=C1)C(F)(F)F)OC1=CC(=CC=C1)C(F)(F)F | [F:1][C:2]([c:5]1[cH:6][cH:7][cH:8][c:9]([OH:10])[cH:28]1)([F:19])[F:20].[Zr:11]([CH3:13])([CH3:14])[CH:23]1[CH:22]=[CH:17][CH:25]=[CH:24]1>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([O:10][Zr:11]([O:12][c:13]2[cH:14][cH:15][cH:16][c:17]([C:18]([F:19])([F:20])[F:21])[cH:22]2)[CH:23]2[CH:24]=[CH:25][CH:26]=[... | Oc1cccc(C(F)(F)F)c1.[CH3][Zr]([CH3])[CH]1C=CC=C1 | FC(F)(F)c1cccc([O][Zr]([O]c2cccc(C(F)(F)F)c2)[CH]2C=CC=C2)c1 | null | null | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | e4ee5ce441830a7deb6264fcee74e909a273bb37745dcae242609e6abaa9d113 | 0926ef7d725a0e530c453cccce66c08b7fe047a9f4cf61cfc163a5e480911316 | C1=C[CH]([Zr]([O]c2ccccc2)[O]c2ccccc2)C=C1 | [CH3;D1;+0:1]-[Zr;H0;D3;+0:2](-[CH3;D1;+0:3])-[CH;D3;+0:4]1-[C:5]=[CH;D2;+0:6]-[CH;D2;+0:7]=[CH;D2;+0:8]-1.[F;D1;H0:9]-[C;H0;D4;+0:10](-[F;H0;D1;+0:11])(-[F;H0;D1;+0:12])-[c:13](:[c:14]):[c:15]:[c:16](-[OH;D1;+0:17]):[c:18]>>[F;D1;H0:9]-[C;H0;D4;+0:10](-[F;D1;H0:19])(-[F;D1;H0:20])-[c:13](:[c:14]):[c:15]:[c:16](-[O;H0;... | null | [] | null | null | null | null | To a 50 ml Schlenk flask containing 138.7 mg (0.5 mmole) of (1-methylboratabenzene) (cyclopentadienyl) dimethyl zirconium [intermediate product of 1st Step] in 15 ml toluene and at 0° C., 162.1 mg (1 mmole) of Trifluoro-m-Cresol in 10 ml toluene is added slowly under stirring. After warming up to room temperature and s... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Aromatic alcohol.Conjugated diene | Trifluoro group.Trifluoro group.Conjugated diene | C1=CCC=C1 | c1ccccc1.C1=CCC=C1 | c1ccccc1.c1ccccc1.C1=CCC=C1 | Other | C1(=CC=CC=C1)C | null | null | Oc1cccc(C(F)(F)F)c1.[CH3][Zr]([CH3])[CH]1C=CC=C1>C1(=CC=CC=C1)C>FC(F)(F)c1cccc([O][Zr]([O]c2cccc(C(F)(F)F)c2)[CH]2C=CC=C2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b63e6b5923624276913729be4e728d9b | O=P([O-])([O-])OP(=O)([O-])OP(=O)([O-])[O-].O=P([O-])([O-])OP(=O)([O-])OP(=O)([O-])[O-]>>O=P([O-])([O-])OP(=O)([O-])[O-].O=P([O-])([O-])[O-] | [O-]P([O-])(=O)OP(=O)([O-])OP(=O)([O-])[O-].[Na+].[Na+].[Na+].[Na+].[Na+].[O-]P(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-].[Na+].[Na+].[Na+].[Na+].[Na+]>>P(=O)([O-])([O-])[O-].[O-]P([O-])(=O)OP(=O)([O-])[O-] | [O:1]=[P:2]([O:3][P:11](=[O:10])([O-:12])[O-:14])([O-:4])[O:5][P:6](=[O:7])([O-:8])[O-:9].O=P([O-])([O-])OP(=O)([O-])OP(=O)([O-])[O-:13]>>[O:1]=[P:2]([O-:3])([O-:4])[O:5][P:6](=[O:7])([O-:8])[O-:9].[O:10]=[P:11]([O-:12])([O-:13])[O-:14] | O=P([O-])([O-])OP(=O)([O-])OP(=O)([O-])[O-].O=P([O-])([O-])OP(=O)([O-])OP(=O)([O-])[O-] | O=P([O-])([O-])OP(=O)([O-])[O-].O=P([O-])([O-])[O-] | null | null | O | Functional Group Interconversion | OtherReaction | 42af6cdfb86a130c92365e01a31b50705eea7bdf12f67dc370bf24402f7ceedc | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | null | O=P(-[O-;H0;D1:1])(-[O-])-O-P(=O)(-[O-])-O-P(=O)(-[O-])-[O-].[#8:2]-[#15:3](-[O;-;D1;H0:4])(=[O;D1;H0:5])-[O;H0;D2;+0:6]-[P;H0;D4;+0:7](-[O;-;D1;H0:8])(-[O;-;D1;H0:9])=[O;D1;H0:10]>>[#8:2]-[#15:3](-[O-;H0;D1:6])(-[O;-;D1;H0:4])=[O;D1;H0:5].[O-;H0;D1:1]-[P;H0;D4;+0:7](-[O;-;D1;H0:8])(-[O;-;D1;H0:9])=[O;D1;H0:10] | 15 | [{"value": 8.0, "product": "P(=O)([O-])([O-])[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 15.0, "product": "[O-]P([O-])(=O)OP(=O)([O-])[O-]", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The industrially important pentasodium triphosphate, Na5P3O10 (sodium tripolyphosphate), is a nonhygroscopic, white, water-soluble salt which is anhydrous or crystallizes with 6H2O and has the general formula NaO—[P(O)(ONa)—O]n—Na where n=3. About 17 g of the salt free from water of crystallization dissolve in 100 g of... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | Other | O | null | null | O=P([O-])([O-])OP(=O)([O-])OP(=O)([O-])[O-].O=P([O-])([O-])OP(=O)([O-])OP(=O)([O-])[O-]>O>O=P([O-])([O-])OP(=O)([O-])[O-].O=P([O-])([O-])[O-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ebc41319e76649ef90442a2e3702c9e1 | CC(C)CN.O=C(O)CBr>>CC(C)CNCC(=O)O | C(C(C)C)N.BrCC(=O)O>>C(C(C)C)NCC(=O)O | [CH3:1][CH:2]([CH3:3])[CH2:4][NH2:5].Br[CH2:6][C:7](=[O:8])[OH:9]>>[CH3:1][CH:2]([CH3:3])[CH2:4][NH:5][CH2:6][C:7](=[O:8])[OH:9] | CC(C)CN.O=C(O)CBr | CC(C)CNCC(=O)O | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | null | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[O;D1;H1:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[O;D1;H1:4] | null | [] | null | null | 8 | HOUR | Isobutylamine (50 mL, 0.5 mol) was cooled in an ice bath, and bromoacetic acid (6.1 g, 43.9 mmol) added slowly as a solid, insuring that each piece dissolved. After stirring overnight, the excess amine was removed and MeOH was added to the resulting oil. The resulting mixture was concentrated, and repeated using MeOH/H... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | null | HBr | null | null | 8 | CC(C)CN.O=C(O)CBr>>CC(C)CNCC(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6f32846c3f30491a999c9981e0eac7a6 | CC(C)CN(CC(=O)O)C(=O)OCC1c2ccccc2-c2ccccc21>>CC(C)C[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O | C(=O)(OCC1C2=CC=CC=C2C2=CC=CC=C12)N(CC(=O)O)CC(C)C.S(=O)(Cl)Cl.CN(C)C=O>>N([C@@H](CC(C)C)C(=O)O)C(=O)OCC1C2=CC=CC=C2C2=CC=CC=C12 | [CH3:1][CH:2]([CH3:3])[CH2:4][N:6]([CH2:5][C:24](=[O:25])[OH:26])[C:7](=[O:8])[O:9][CH2:10][CH:11]1[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2-[c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]21>>[CH3:1][CH:2]([CH3:3])[CH2:4][C@H:5]([NH:6][C:7](=[O:8])[O:9][CH2:10][CH:11]1[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2-[c:18]2[cH:19... | CC(C)CN(CC(=O)O)C(=O)OCC1c2ccccc2-c2ccccc21 | CC(C)C[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O | null | null | ClCl | Miscellaneous | OtherReaction | 4f49f9e37883927ad7cca84a61e84bd95ede462dbc710cc77bebacff28109d11 | b932663ddba91899c323dafb4072eae107b143d8b23ee72dc5710c79986212ad | c1ccc2c(c1)Cc1ccccc1-2 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[N;H0;D3;+0:5](-[CH2;D2;+0:6]-[C:7](-[C;D1;H3:8])-[C;D1;H3:9])-[CH2;D2;+0:10]-[C:11](=[O;D1;H0:12])-[O;D1;H1:13]>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[NH;D2;+0:5]-[C@@H;D3;+0:10](-[CH2;D2;+0:6]-[C:7](-[C;D1;H3:8])-[C;D1;H3:9])-[C:11](=[O;D1;H0:12])-[O;D1;H1:13] | null | [] | null | null | 5 | HOUR | FMOC-Leu*-Cl was prepared by dissolving FMOC-N-isobutylglycine (150 mg, 0.42 mmol) in CH2 Cl2 (2.8 mL), and adding thionyl chloride (309 μL, 4.2 mmol) and 3 μL DMF (0.04 mmol). The reaction mixture was stirred for 5 hours and concentrated in vacuo, repeatedly dissolving in CH2 Cl2 (3××) to provide FMOC-Leu*-Cl as a col... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester | Carbamic ester | null | null | c1ccc2c(c1)Cc1ccccc12 | null | ClCl | null | 5 | CC(C)CN(CC(=O)O)C(=O)OCC1c2ccccc2-c2ccccc21>ClCl>CC(C)C[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-72933cad450b4014b6b24b165b8c5239 | CO[C@@H]1O[C@H](COCc2ccc(Cl)cc2Cl)[C@@H](OCc2ccc(Cl)cc2Cl)[C@H]1OCc1ccc(Cl)cc1Cl>>CO[C@@H]1O[C@H](COCc2ccc(Cl)cc2Cl)[C@@H](OCc2ccc(Cl)cc2Cl)[C@H]1O | CO[C@H]1[C@H](OCC2=C(C=C(C=C2)Cl)Cl)[C@H](OCC2=C(C=C(C=C2)Cl)Cl)[C@H](O1)COCC1=C(C=C(C=C1)Cl)Cl.Cl[Sn](Cl)(Cl)Cl>>CO[C@H]1[C@H](O)[C@H](OCC2=C(C=C(C=C2)Cl)Cl)[C@H](O1)COCC1=C(C=C(C=C1)Cl)Cl | Clc1ccc(C[O:29][C@H:28]2[C@H:3]([O:2][CH3:1])[O:4][C@H:5]([CH2:6][O:7][CH2:8][c:9]3[cH:10][cH:11][c:12]([Cl:13])[cH:14][c:15]3[Cl:16])[C@H:17]2[O:18][CH2:19][c:20]2[cH:21][cH:22][c:23]([Cl:24])[cH:25][c:26]2[Cl:27])c(Cl)c1>>[CH3:1][O:2][C@@H:3]1[O:4][C@H:5]([CH2:6][O:7][CH2:8][c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][... | CO[C@@H]1O[C@H](COCc2ccc(Cl)cc2Cl)[C@@H](OCc2ccc(Cl)cc2Cl)[C@H]1OCc1ccc(Cl)cc1Cl | CO[C@@H]1O[C@H](COCc2ccc(Cl)cc2Cl)[C@@H](OCc2ccc(Cl)cc2Cl)[C@H]1O | null | null | C(Cl)Cl | Deprotection | OtherReaction | edd30f410f2bea3d65792f7c0ce1c643d95594f79a65acaa1565509b584d54a8 | b078c7ecc25f90e1d6f68300f7c01a000848ed9dc63a5fd488fdc1985d60201d | c1ccc(COC[C@H]2OCC[C@@H]2OCc2ccccc2)cc1 | Cl-c1:c:c:c(-C-[O;H0;D2;+0:1]-[C:2](-[C:3])-[C:4]-[#8:5]):c(-Cl):c:1>>[#8:5]-[C:4]-[C:2](-[OH;D1;+0:1])-[C:3] | null | [] | null | null | 27 | HOUR | To a solution of the product of Step 1 (171.60 g, 0.2676 mol) in 1.8 L CH2Cl2 that was cooled to 0° C., was added dropwise a solution of stannous chloride (31.522 mL, 0.2676 mol) in 134 mL CH2Cl2 while stirring. After the solution was kept at 3° C. for 27 hours, another 5.031 ml of SnCl4 (0.04282 mol) was added and the... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ether | Secondary alcohol | c1ccccc1 | null | C1CCOC1.c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl | null | 27 | CO[C@@H]1O[C@H](COCc2ccc(Cl)cc2Cl)[C@@H](OCc2ccc(Cl)cc2Cl)[C@H]1OCc1ccc(Cl)cc1Cl>C(Cl)Cl>CO[C@@H]1O[C@H](COCc2ccc(Cl)cc2Cl)[C@@H](OCc2ccc(Cl)cc2Cl)[C@H]1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-080e4b8602244c829a89bdfa381e91f1 | Clc1ncnc2[nH]ccc12.O=C1CCC(=O)N1I>>Clc1ncnc2[nH]cc(I)c12 | C1=CNC2=C1C(=NC=N2)Cl.IN1C(CCC1=O)=O>>C1=C(C2=C(N1)N=CN=C2Cl)I | [Cl:1][c:2]1[n:3][cH:4][n:5][c:6]2[nH:7][cH:8][cH:9][c:11]12.O=C1CCC(=O)N1[I:10]>>[Cl:1][c:2]1[n:3][cH:4][n:5][c:6]2[nH:7][cH:8][c:9]([I:10])[c:11]12 | Clc1ncnc2[nH]ccc12.O=C1CCC(=O)N1I | Clc1ncnc2[nH]cc(I)c12 | null | null | CN(C)C=O | Functional Group Interconversion | OtherReaction | 064df7a133fc98eefb7d614f7980f12fbe09d15298c782f8d6f46bf1fd9d7a51 | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1ncc2cc[nH]c2n1 | O=C1-C-C-C(=O)-N-1-[I;H0;D1;+0:1].[Cl;D1;H0:2]-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]2:[#7;a:8]:[c:9]:[cH;D2;+0:10]:[c:11]:1:2>>[Cl;D1;H0:2]-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]2:[#7;a:8]:[c:9]:[c;H0;D3;+0:10](-[I;H0;D1;+0:1]):[c:11]:1:2 | 83 | [{"value": 83.0, "product": "C1=C(C2=C(N1)N=CN=C2Cl)I", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.8, "product": "C1=C(C2=C(N1)N=CN=C2Cl)I", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 6-Chloro-7-deazapurine 10.75 g (70 mmol) and N-iodosuccinimide (16.8 g, 75 mmol) were dissolved in 400 ml of dry DMF and left at ambient temperature in the darkness over night. The solvent was evaporated. The dark residue was distributed between 500 ml of ethyl acetate and 150 ml of 10% Na2SO3. Organic fraction was was... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1ncc2cc[nH]c2n1.C1CCNC1 | c1ncc2cc[nH]c2n1 | c1ncc2cc[nH]c2n1 | HO- | CN(C)C=O | null | null | Clc1ncnc2[nH]ccc12.O=C1CCC(=O)N1I>CN(C)C=O>Clc1ncnc2[nH]cc(I)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2c4f74d36a3e4147b27538559e142388 | CCCCC/C=C\C/C=C\C=C\C=C\[C@@H]1O[C@H]1CCCC(=O)O.CCCCC/C=C\C/C=C\C=C\C=C\[C@@H]1O[C@H]1CCCC(=O)O>>CCCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O | [Na+].[Cl-].C(CN(CC(=O)O)CC(=O)O)N(CC(=O)O)CC(=O)O.CCCCC/C=C\C/C=C\C=C\C=C\[C@H]1[C@@H](O1)CCCC(=O)O.CCCCC/C=C\C/C=C\C=C\C=C\[C@H]1[C@@H](O1)CCCC(=O)OC.CCCCC/C=C\C/C=C\C=C\C=C\[C@H]1[C@@H](O1)CCCC(=O)O>>CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@H](CCCC(=O)O)O)O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8]/[CH:9]=[CH:11]\[CH:12]=[CH:13]\[CH:14]=[CH:15]\[C@H:16]1[C@H:17]([CH2:19][CH2:20][CH2:21][C:22](=[O:23])[OH:24])[O:18]1.CCCCC/C=C\C/C=C\C=C\C=C\[C@@H]1O[C@H]1CCCC(=O)[OH:10]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8][C@@H:9]([OH:10])/[CH:11]=[CH:... | CCCCC/C=C\C/C=C\C=C\C=C\[C@@H]1O[C@H]1CCCC(=O)O.CCCCC/C=C\C/C=C\C=C\C=C\[C@@H]1O[C@H]1CCCC(=O)O | CCCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O | null | null | P(=O)([O-])([O-])[O-].[K+].[K+].[K+] | Heteroatom Alkylation and Arylation | OtherReaction | e1b14f1722441379d43d7ab1609123bdb4931e377ee3e466ac3b4a8ee19244dc | f8aa51fdbbb50115bfb4355d4dd5856df4f8b97b895b2d1ca32f86628e5590bd | null | C-C-C-C-C/C=C\C/C=C\C=C\C=C\[C@H]1-O-[C@@H]-1-C-C-C-C(=O)-[OH;D1;+0:1].[C:2]-[C:3]-[C@@H;D3;+0:4]1-[O;H0;D2;+0:5]-[C@H;D3;+0:6]-1/[CH;D2;+0:7]=[CH;D2;+0:8]/[CH;D2;+0:9]=[CH;D2;+0:10]/[CH;D2;+0:11]=[CH;D2;+0:12]\[C:13]/[C:14]=[C:15]\[C:16]>>[C:2]-[C:3]-[C@H;D3;+0:4](-[OH;D1;+0:5])/[CH;D2;+0:6]=[CH;D2;+0:7]\[CH;D2;+0:8]=... | null | [] | null | null | null | null | The LTA4 substrate was freshly prepared by alkaline hydrolysis of LTA4 methyl ester (Cayman Chemical Co., USA). After incubating for 10 minutes in the presence of LTA4 (1 μM in 50 mM Tris-HCl, 0.15 M NaCl, 0.5% BSA, pH 7.4), the reaction is stopped by diluting 1/20 in 0.1 M potassium phosphate buffer containing 1.5 mM ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether.Ether.Conjugated diene.Conjugated diene.Conjugated diene.Conjugated diene | Secondary alcohol.Secondary alcohol.Conjugated diene.Conjugated diene | C1CO1.C1CO1 | null | null | HO- | P(=O)([O-])([O-])[O-].[K+].[K+].[K+] | null | null | CCCCC/C=C\C/C=C\C=C\C=C\[C@@H]1O[C@H]1CCCC(=O)O.CCCCC/C=C\C/C=C\C=C\C=C\[C@@H]1O[C@H]1CCCC(=O)O>P(=O)([O-])([O-])[O-].[K+].[K+].[K+]>CCCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3ef1c6764a8d4e91a9de0d35ff77b2ac | CCCCCCCCCCCCCCCCOCCCO.Nc1ncnc2c1ncn2CCOCP(=O)(O)O>>CCCCCCCCCCCCCCCCOCCCOP(=O)(O)COCCn1cnc2c(N)ncnc21 | C1=NC(=C2C(=N1)N(C=N2)CCOCP(=O)(O)O)N.C(CCCCCCCCCCCCCCC)OCCCO.C1CCC(CC1)N=C=NC2CCCCC2>>CCCCCCCCCCCCCCCCOCCCOP(=O)(COCCN1C=NC2=C1N=CN=C2N)O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][CH2:20][OH:21].O[P:22](=[O:23])([OH:24])[CH2:25][O:26][CH2:27][CH2:28][n:29]1[cH:30][n:31][c:32]2[c:33]([NH2:34])[n:35][cH:36][n:37][c:38]12>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][... | CCCCCCCCCCCCCCCCOCCCO.Nc1ncnc2c1ncn2CCOCP(=O)(O)O | CCCCCCCCCCCCCCCCOCCCOP(=O)(O)COCCn1cnc2c(N)ncnc21 | null | null | N1=CC=CC=C1 | Miscellaneous | OtherReaction | f468963cd150795c559ea97eef415e4c6e817d5e41b8e41bf56e6fc6478dce9b | 0450d2d3d6169ebd913d75de6102597ba0029b73d4e4cd2ca50ccc23bda73392 | c1ncc2nc[nH]c2n1 | O-[P;H0;D4;+0:1](=[O;D1;H0:2])(-[O;D1;H1:3])-[C:4]-[#8:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[#8:5]-[C:4]-[P;H0;D4;+0:1](=[O;D1;H0:2])(-[O;D1;H1:3])-[O;H0;D2;+0:8]-[C:7]-[C:6] | null | [] | null | null | 18 | HOUR | To a mixture of adefovir (1.36 g, 5 mmol) and 3-hexadecyloxy-1-propanol (1.8 g, 6 mmol) in dry pyridine was added DCC (2.06 g, 10 mmol). The mixture was heated to reflux and stirred 18 h then cooled and filtered. The filtrate was concentrated under reduced pressure and the residue was applied to a short column of silic... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | null | null | null | c1ncnc2[nH]cnc12 | HO- | N1=CC=CC=C1 | null | 18 | CCCCCCCCCCCCCCCCOCCCO.Nc1ncnc2c1ncn2CCOCP(=O)(O)O>N1=CC=CC=C1>CCCCCCCCCCCCCCCCOCCCOP(=O)(O)COCCn1cnc2c(N)ncnc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6314169ce51742128456dcdcd895e04a | C=C1[C@H](O[Si](C)(C)C(C)(C)C)CC(O)(C(=O)OC)C[C@H]1O[Si](C)(C)C(C)(C)C>>C=C1[C@H](O[Si](C)(C)C(C)(C)C)CC(O)(CO)C[C@H]1O[Si](C)(C)C(C)(C)C | COC(=O)C1(C[C@H](C([C@@H](C1)O[Si](C)(C)C(C)(C)C)=C)O[Si](C)(C)C(C)(C)C)O.C1CCOC1>>[Si](C)(C)(C(C)(C)C)O[C@@H]1CC(C[C@H](C1=C)O[Si](C)(C)C(C)(C)C)(O)CO | CO[C:15]([C:13]1([OH:14])[CH2:12][C@@H:3]([O:4][Si:5]([CH3:6])([CH3:7])[C:8]([CH3:9])([CH3:10])[CH3:11])[C:2](=[CH2:1])[C@H:18]([O:19][Si:20]([CH3:21])([CH3:22])[C:23]([CH3:24])([CH3:25])[CH3:26])[CH2:17]1)=[O:16]>>[CH2:1]=[C:2]1[C@H:3]([O:4][Si:5]([CH3:6])([CH3:7])[C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][C:13]([OH:14... | C=C1[C@H](O[Si](C)(C)C(C)(C)C)CC(O)(C(=O)OC)C[C@H]1O[Si](C)(C)C(C)(C)C | C=C1[C@H](O[Si](C)(C)C(C)(C)C)CC(O)(CO)C[C@H]1O[Si](C)(C)C(C)(C)C | null | null | null | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | C=C1CCCCC1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[O;D1;H1:4])(-[C:5])-[C:6]>>[C:5]-[C:3](-[O;D1;H1:4])(-[CH2;D2;+0:1]-[OH;D1;+0:2])-[C:6] | null | [] | null | null | 6 | HOUR | (i) To a stirred solution of the ester 3 (90 mg, 0.21 mmol) in anhydrous THF (8 mL) lithium aluminum hydride (60 mg, 1.6 mmol) was added at 0° C. under argon. The cooling bath was removed after 1 h and the stirring was continued at 6° C. for 12 h and at room temperature for 6 h. The excess of the reagent was decomposed... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1CCCCC1 | Other | null | null | 6 | C=C1[C@H](O[Si](C)(C)C(C)(C)C)CC(O)(C(=O)OC)C[C@H]1O[Si](C)(C)C(C)(C)C>>C=C1[C@H](O[Si](C)(C)C(C)(C)C)CC(O)(CO)C[C@H]1O[Si](C)(C)C(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-249b176810ef4aadbc47024b18b1e628 | C=C1[C@H](O[Si](C)(C)C(C)(C)C)CC(O)(C(=O)OC)C[C@H]1O[Si](C)(C)C(C)(C)C>>C=C1[C@H](O[Si](C)(C)C(C)(C)C)CC(O)(CO)C[C@H]1O[Si](C)(C)C(C)(C)C | [H-].C(C(C)C)[Al+]CC(C)C.COC(=O)C1(C[C@H](C([C@@H](C1)O[Si](C)(C)C(C)(C)C)=C)O[Si](C)(C)C(C)(C)C)O>>[Si](C)(C)(C(C)(C)C)O[C@@H]1CC(C[C@H](C1=C)O[Si](C)(C)C(C)(C)C)(O)CO | CO[C:15]([C:13]1([OH:14])[CH2:12][C@@H:3]([O:4][Si:5]([CH3:6])([CH3:7])[C:8]([CH3:9])([CH3:10])[CH3:11])[C:2](=[CH2:1])[C@H:18]([O:19][Si:20]([CH3:21])([CH3:22])[C:23]([CH3:24])([CH3:25])[CH3:26])[CH2:17]1)=[O:16]>>[CH2:1]=[C:2]1[C@H:3]([O:4][Si:5]([CH3:6])([CH3:7])[C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][C:13]([OH:14... | C=C1[C@H](O[Si](C)(C)C(C)(C)C)CC(O)(C(=O)OC)C[C@H]1O[Si](C)(C)C(C)(C)C | C=C1[C@H](O[Si](C)(C)C(C)(C)C)CC(O)(CO)C[C@H]1O[Si](C)(C)C(C)(C)C | null | null | CCOCC | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | C=C1CCCCC1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[O;D1;H1:4])(-[C:5])-[C:6]>>[C:5]-[C:3](-[O;D1;H1:4])(-[CH2;D2;+0:1]-[OH;D1;+0:2])-[C:6] | 24 | [{"value": 24.0, "product": "[Si](C)(C)(C(C)(C)C)O[C@@H]1CC(C[C@H](C1=C)O[Si](C)(C)C(C)(C)C)(O)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 21.4, "product": "[Si](C)(C)(C(C)(C)C)O[C@@H]1CC(C[C@H](C1=C)O[Si](C)(C)C(C)(C)C)(O)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -24 | CELSIUS | 1.5 | HOUR | Diisobutylaluminum hydride (1.5 M in toluene, 2.0 mL, 3 mmol) was added to a solution of the ester 3 (215 mg, 0.5 mmol) in anhydrous ether (3 mL) at −78° C. under argon. The mixture was stirred at −78° C. for 3 h and at −24° C. for 1.5 h, diluted with ether (10 mL) and quenched by the slow addition of 2N potassium sodi... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1CCCCC1 | Other | CCOCC | -24 | 1.5 | C=C1[C@H](O[Si](C)(C)C(C)(C)C)CC(O)(C(=O)OC)C[C@H]1O[Si](C)(C)C(C)(C)C>CCOCC>C=C1[C@H](O[Si](C)(C)C(C)(C)C)CC(O)(CO)C[C@H]1O[Si](C)(C)C(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-621c1b4670df48f8bcea5e369085ab2b | C=C1[C@H](O[Si](C)(C)C(C)(C)C)CC(O)(CO)C[C@H]1O[Si](C)(C)C(C)(C)C>>C=C1[C@H](O[Si](C)(C)C(C)(C)C)CC(=O)C[C@H]1O[Si](C)(C)C(C)(C)C | I(=O)(=O)(=O)[O-].[Na+].[Si](C)(C)(C(C)(C)C)O[C@@H]1CC(C[C@H](C1=C)O[Si](C)(C)C(C)(C)C)(O)CO>>[Si](C)(C)(C(C)(C)C)O[C@@H]1CC(C[C@H](C1=C)O[Si](C)(C)C(C)(C)C)=O | OC[C:13]1([OH:14])[CH2:12][C@@H:3]([O:4][Si:5]([CH3:6])([CH3:7])[C:8]([CH3:9])([CH3:10])[CH3:11])[C:2](=[CH2:1])[C@H:16]([O:17][Si:18]([CH3:19])([CH3:20])[C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:15]1>>[CH2:1]=[C:2]1[C@H:3]([O:4][Si:5]([CH3:6])([CH3:7])[C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][C:13](=[O:14])[CH2:15][C@H:... | C=C1[C@H](O[Si](C)(C)C(C)(C)C)CC(O)(CO)C[C@H]1O[Si](C)(C)C(C)(C)C | C=C1[C@H](O[Si](C)(C)C(C)(C)C)CC(=O)C[C@H]1O[Si](C)(C)C(C)(C)C | null | null | CO.[Cl-].[Na+].O | Miscellaneous | OtherReaction | c7800efd344f51d4636480dba4329ad373a9665d31756b5e0e498778650fe17a | d8333db1a8553533b9f31a51fd46ac10421b6606be90ce648ca3b16dc0428896 | C=C1CCC(=O)CC1 | O-C-[C;H0;D4;+0:1]1(-[OH;D1;+0:2])-[C:3]-[C:4]-[C:5](=[C;D1;H2:6])-[C:7]-[C:8]-1>>[C;D1;H2:6]=[C:5]1-[C:7]-[C:8]-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[C:4]-1 | null | [] | 0 | CELSIUS | 1 | HOUR | Sodium periodate saturated water (2.2 mL) was added to a solution of the diol 4 (146 mg, 0.36 mmol) in methanol (9 mL) at 0° C. The solution was stirred at 0° C. for 1 h, poured into brine and extracted with ether and benzene. The organic extracts were combined, washed with brine, dried (MgSO4) and evaporated. An oily ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Tertiary alcohol | Ketone | C1CCCCC1 | C1CCCCC1 | C1CCCCC1 | HO- | CO.[Cl-].[Na+].O | 0 | 1 | C=C1[C@H](O[Si](C)(C)C(C)(C)C)CC(O)(CO)C[C@H]1O[Si](C)(C)C(C)(C)C>CO.[Cl-].[Na+].O>C=C1[C@H](O[Si](C)(C)C(C)(C)C)CC(=O)C[C@H]1O[Si](C)(C)C(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f2c66aeb0d5f475b9780334f93325d54 | CC(=O)CN1CCN(C(=O)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)[C@H](Cc2c[nH]c3ccccc23)C1.CN(C)CCON>>CC(CN1CCN(C(=O)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)[C@H](Cc2c[nH]c3ccccc23)C1)=NOCCN(C)C | FC(C=1C=C(C(=O)N2[C@@H](CN(CC2)CC(C)=O)CC2=CNC3=CC=CC=C23)C=C(C1)C(F)(F)F)(F)F.Cl.Cl.CN(CCON)C.C(C)(=O)[O-].[Na+]>>CN(CCON=C(CN1C[C@H](N(CC1)C(C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)=O)CC1=CNC2=CC=CC=C12)C)C | O=[C:2]([CH3:1])[CH2:3][N:4]1[CH2:5][CH2:6][N:7]([C:8](=[O:9])[c:10]2[cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][c:18]([C:19]([F:20])([F:21])[F:22])[cH:23]2)[C@H:24]([CH2:25][c:26]2[cH:27][nH:28][c:29]3[cH:30][cH:31][cH:32][cH:33][c:34]23)[CH2:35]1.[NH2:36][O:37][CH2:38][CH2:39][N:40]([CH3:41])[CH3:42]>>[CH3:1][... | CC(=O)CN1CCN(C(=O)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)[C@H](Cc2c[nH]c3ccccc23)C1.CN(C)CCON | CC(CN1CCN(C(=O)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)[C@H](Cc2c[nH]c3ccccc23)C1)=NOCCN(C)C | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 3d7a74a3d1c5abb5292963d4a3067f1fb8a89aead752dc9bb1d63522c4c0bd5c | 6b0edeaa66853687109d0d530554f76edf36b01a8ec084e7ae9c709f0949a6b9 | O=C(c1ccccc1)N1CCNC[C@H]1Cc1c[nH]c2ccccc12 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C:3]-[#7:4].[C:5]-[#8:6]-[NH2;D1;+0:7]>>[#7:4]-[C:3]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[N;H0;D2;+0:7]-[#8:6]-[C:5] | 104 | [{"value": 95.0, "product": "CN(CCON=C(CN1C[C@H](N(CC1)C(C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)=O)CC1=CNC2=CC=CC=C12)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 104.0, "product": "CN(CCON=C(CN1C[C@H](N(CC1)C(C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)=O)CC1=CNC2=CC=CC=C12)C)C", "details": "CALCULATEDPERCENTYIELD", ... | null | null | null | null | A mixture of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)-4-(2-propanon-1-yl)piperazine (255 mg), O-[2-(dimethylamino)ethyl]hydroxylamine dihydrochloride (89 mg), sodium acetate (catalytically), and methanol (10 mL) was heated under reflux for 2 h. The solvent was removed in vacuo, and the residue w... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | null | null | null | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2[nH]ccc2c1 | HO- | CO | null | null | CC(=O)CN1CCN(C(=O)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)[C@H](Cc2c[nH]c3ccccc23)C1.CN(C)CCON>CO>CC(CN1CCN(C(=O)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)[C@H](Cc2c[nH]c3ccccc23)C1)=NOCCN(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ae023882c9984179bbf5210487a49852 | ClCC=NOCCN1CCOCC1.O=C(c1cc(C(F)(F)F)cc(C(F)(F)F)c1)N1CCNC[C@H]1Cc1c[nH]c2ccccc12>>O=C(c1cc(C(F)(F)F)cc(C(F)(F)F)c1)N1CCN(CC=NOCCN2CCOCC2)C[C@H]1Cc1c[nH]c2ccccc12 | N1(CCOCC1)CCON=CCCl.FC(C=1C=C(C(=O)N2[C@@H](CNCC2)CC2=CNC3=CC=CC=C23)C=C(C1)C(F)(F)F)(F)F.C(C)(C)N(CC)C(C)C>>N1(CCOCC1)CCON=CCN1C[C@H](N(CC1)C(C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)=O)CC1=CNC2=CC=CC=C12 | Cl[CH2:21][CH:22]=[N:23][O:24][CH2:25][CH2:26][N:27]1[CH2:28][CH2:29][O:30][CH2:31][CH2:32]1.[O:1]=[C:2]([c:3]1[cH:4][c:5]([C:6]([F:7])([F:8])[F:9])[cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16]1)[N:17]1[CH2:18][CH2:19][NH:20][CH2:33][C@H:34]1[CH2:35][c:36]1[cH:37][nH:38][c:39]2[cH:40][cH:41][cH:42][cH:43][c:44]12>... | ClCC=NOCCN1CCOCC1.O=C(c1cc(C(F)(F)F)cc(C(F)(F)F)c1)N1CCNC[C@H]1Cc1c[nH]c2ccccc12 | O=C(c1cc(C(F)(F)F)cc(C(F)(F)F)c1)N1CCN(CC=NOCCN2CCOCC2)C[C@H]1Cc1c[nH]c2ccccc12 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b703623ddc3b029d4716c15f5414f41773434bcc7e3f3853faf62273596bed77 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(c1ccccc1)N1CCN(CC=NOCCN2CCOCC2)C[C@H]1Cc1c[nH]c2ccccc12 | Cl-[CH2;D2;+0:1]-[C:2]=[#7:3]-[#8:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[#8:4]-[#7:3]=[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#7:5]-[C:10]-[C:9]-1 | 96.6 | [{"value": 95.0, "product": "N1(CCOCC1)CCON=CCN1C[C@H](N(CC1)C(C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)=O)CC1=CNC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.6, "product": "N1(CCOCC1)CCON=CCN1C[C@H](N(CC1)C(C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)=O)CC1=CNC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD... | null | null | null | null | A mixture of 2-chloroethanal O-[2-(morpholin-4-yl)ethyl]oxime (0.13 g), (2R)-1-[3,5-bis(trifluoromethyl)-benzoyl]-2-(1H-indol-3-ylmethyl)piperazine (0.29 g), diisopropylethylamine (0.11 mL), and acetonitrile (10 mL) was heated under reflux overnight. After cooling to room temperature the solvent was removed in vacuo, a... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.C1COCC[NH]1.c1ccc2[nH]ccc2c1 | HCl | C(C)#N | null | null | ClCC=NOCCN1CCOCC1.O=C(c1cc(C(F)(F)F)cc(C(F)(F)F)c1)N1CCNC[C@H]1Cc1c[nH]c2ccccc12>C(C)#N>O=C(c1cc(C(F)(F)F)cc(C(F)(F)F)c1)N1CCN(CC=NOCCN2CCOCC2)C[C@H]1Cc1c[nH]c2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-432a32e32913427491b423a3888d4dd7 | O=C(CBr)c1ccccc1.O=C(c1cc(C(F)(F)F)cc(C(F)(F)F)c1)N1CCNC[C@H]1Cc1c[nH]c2ccccc12>>O=C(CN1CCN(C(=O)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)[C@H](Cc2c[nH]c3ccccc23)C1)c1ccccc1 | C(C(=O)C1=CC=CC=C1)Br.FC(C=1C=C(C(=O)N2[C@@H](CNCC2)CC2=CNC3=CC=CC=C23)C=C(C1)C(F)(F)F)(F)F.[I-].[K+].C(C)(C)N(CC)C(C)C>>FC(C=1C=C(C(=O)N2[C@@H](CN(CC2)CC(=O)C2=CC=CC=C2)CC2=CNC3=CC=CC=C23)C=C(C1)C(F)(F)F)(F)F | Br[CH2:3][C:2](=[O:1])[c:36]1[cH:37][cH:38][cH:39][cH:40][cH:41]1.[NH:4]1[CH2:5][CH2:6][N:7]([C:8](=[O:9])[c:10]2[cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][c:18]([C:19]([F:20])([F:21])[F:22])[cH:23]2)[C@H:24]([CH2:25][c:26]2[cH:27][nH:28][c:29]3[cH:30][cH:31][cH:32][cH:33][c:34]23)[CH2:35]1>>[O:1]=[C:2]([CH2:3]... | O=C(CBr)c1ccccc1.O=C(c1cc(C(F)(F)F)cc(C(F)(F)F)c1)N1CCNC[C@H]1Cc1c[nH]c2ccccc12 | O=C(CN1CCN(C(=O)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)[C@H](Cc2c[nH]c3ccccc23)C1)c1ccccc1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | f26d51e2c774d81a020fc5d8715a5a6f6b06297cf3257cffbe63e8f82c8c4256 | 98b92c1800516dd6f2e7ad31e751bba9f02d8a8062f38a8945939bbe90ecca84 | O=C(CN1CCN(C(=O)c2ccccc2)[C@H](Cc2c[nH]c3ccccc23)C1)c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[O;D1;H0:3]=[C:2](-[c:4])-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#7:5]-[C:10]-[C:9]-1 | 85.8 | [{"value": 85.0, "product": "FC(C=1C=C(C(=O)N2[C@@H](CN(CC2)CC(=O)C2=CC=CC=C2)CC2=CNC3=CC=CC=C23)C=C(C1)C(F)(F)F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.8, "product": "FC(C=1C=C(C(=O)N2[C@@H](CN(CC2)CC(=O)C2=CC=CC=C2)CC2=CNC3=CC=CC=C23)C=C(C1)C(F)(F)F)(F)F", "details": "CALCULATEDPERCENTYIE... | null | null | 8 | HOUR | A mixture of phenacyl bromide (0.88 g), (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)piperazine (2 g), potassium iodide (catalytical), diisopropyl-ethylamine (0.77 mL), and acetonitrile (20 mL) was stirred at room temperature overnight. After cooling to room temperature the solvent was removed in vac... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Secondary amine | Ketone.Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | HBr | C(C)#N | null | 8 | O=C(CBr)c1ccccc1.O=C(c1cc(C(F)(F)F)cc(C(F)(F)F)c1)N1CCNC[C@H]1Cc1c[nH]c2ccccc12>C(C)#N>O=C(CN1CCN(C(=O)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)[C@H](Cc2c[nH]c3ccccc23)C1)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-01898ff63c1d4a31a48358210ecd48cd | CC1(CCCCl)OCCO1.O=C(c1cc(C(F)(F)F)cc(C(F)(F)F)c1)N1CCNC[C@H]1Cc1c[nH]c2ccccc12>>CC1(CCCN2CCN(C(=O)c3cc(C(F)(F)F)cc(C(F)(F)F)c3)[C@H](Cc3c[nH]c4ccccc34)C2)OCCO1 | C1COC(C)(CCCCl)O1.FC(C=1C=C(C(=O)N2[C@@H](CNCC2)CC2=CNC3=CC=CC=C23)C=C(C1)C(F)(F)F)(F)F.C(C)(C)N(CC)C(C)C.CN(C=O)C>>FC(C=1C=C(C(=O)N2[C@@H](CN(CC2)CCCC2(OCCO2)C)CC2=CNC3=CC=CC=C23)C=C(C1)C(F)(F)F)(F)F | Cl[CH2:5][CH2:4][CH2:3][C:2]1([CH3:1])[O:38][CH2:39][CH2:40][O:41]1.[NH:6]1[CH2:7][CH2:8][N:9]([C:10](=[O:11])[c:12]2[cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][c:20]([C:21]([F:22])([F:23])[F:24])[cH:25]2)[C@H:26]([CH2:27][c:28]2[cH:29][nH:30][c:31]3[cH:32][cH:33][cH:34][cH:35][c:36]23)[CH2:37]1>>[CH3:1][C:2]1([... | CC1(CCCCl)OCCO1.O=C(c1cc(C(F)(F)F)cc(C(F)(F)F)c1)N1CCNC[C@H]1Cc1c[nH]c2ccccc12 | CC1(CCCN2CCN(C(=O)c3cc(C(F)(F)F)cc(C(F)(F)F)c3)[C@H](Cc3c[nH]c4ccccc34)C2)OCCO1 | null | null | O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(c1ccccc1)N1CCN(CCCC2OCCO2)C[C@H]1Cc1c[nH]c2ccccc12 | Cl-[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 | 40 | [{"value": 40.0, "product": "FC(C=1C=C(C(=O)N2[C@@H](CN(CC2)CCCC2(OCCO2)C)CC2=CNC3=CC=CC=C23)C=C(C1)C(F)(F)F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 39.9, "product": "FC(C=1C=C(C(=O)N2[C@@H](CN(CC2)CCCC2(OCCO2)C)CC2=CNC3=CC=CC=C23)C=C(C1)C(F)(F)F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is... | 90 | CELSIUS | null | null | A mixture of 5-chloro-2-pentanone ethylene ketal (0.54 g), (2R)-1-[3,5-bis(trifluoro-methyl)benzoyl]-2-(1H-indol-3-ylmethyl)piperazine (1.37 g), diisopropylethylamine (0.6 mL), and dimethylformamide (25 mL) was heated overnight, at 90°C. After cooling to room temperature the mixture was poured in water and extracted wi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2[nH]ccc2c1.C1COCO1 | HCl | O | 90 | null | CC1(CCCCl)OCCO1.O=C(c1cc(C(F)(F)F)cc(C(F)(F)F)c1)N1CCNC[C@H]1Cc1c[nH]c2ccccc12>O>CC1(CCCN2CCN(C(=O)c3cc(C(F)(F)F)cc(C(F)(F)F)c3)[C@H](Cc3c[nH]c4ccccc34)C2)OCCO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-755c0c4338ec42bd89c9aaaf59b8e5e7 | C=CC(C)=O.CC(=O)CCCN1CCN(C(=O)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)[C@H](Cc2c[nH]c3ccccc23)C1>>CC(=O)CCN1CCN(C(=O)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)[C@H](Cc2c[nH]c3ccccc23)C1 | FC(C=1C=C(C(=O)N2[C@@H](CN(CC2)CCCC(C)=O)CC2=CNC3=CC=CC=C23)C=C(C1)C(F)(F)F)(F)F.C(=C)C(=O)C>>FC(C=1C=C(C(=O)N2[C@@H](CN(CC2)CCC(C)=O)CC2=CNC3=CC=CC=C23)C=C(C1)C(F)(F)F)(F)F | C=CC([CH3:1])=[O:3].CC(=O)[CH2:2][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][N:9]([C:10](=[O:11])[c:12]2[cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][c:20]([C:21]([F:22])([F:23])[F:24])[cH:25]2)[C@H:26]([CH2:27][c:28]2[cH:29][nH:30][c:31]3[cH:32][cH:33][cH:34][cH:35][c:36]23)[CH2:37]1>>[CH3:1][C:2](=[O:3])[CH2:4][CH2:5][N:... | C=CC(C)=O.CC(=O)CCCN1CCN(C(=O)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)[C@H](Cc2c[nH]c3ccccc23)C1 | CC(=O)CCN1CCN(C(=O)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)[C@H](Cc2c[nH]c3ccccc23)C1 | null | null | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | a8e0b54bac297f075fc0666a9bcf94251f3c5c7ab74af247059fb62f60624ddb | bb58fbf613c19ecfa53df6e8ba72f98b3828621e619f33e5bc9d027150c5f070 | O=C(c1ccccc1)N1CCNC[C@H]1Cc1c[nH]c2ccccc12 | C-C(=O)-[CH2;D2;+0:1]-[C:2]-[C:3].C=C-C(-[CH3;D1;+0:4])=[O;H0;D1;+0:5]>>[C:3]-[C:2]-[C;H0;D3;+0:1](-[CH3;D1;+0:4])=[O;H0;D1;+0:5] | null | [] | null | null | null | null | To a solution of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)-4-(4-pentanon-1-yl)piperazine (1.37 g) in toluene (15 mL) was added drop-wise methyl vinyl ketone (0.3 g). After 2.5 h at room temperature the solution was concentrated to afford crude (2R)-1-[3,5-bis(trifluoromethyl)-benzoyl]-2-(1H-indol... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Vinyl | Ketone | null | null | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2[nH]ccc2c1 | HO- | C1(=CC=CC=C1)C | null | null | C=CC(C)=O.CC(=O)CCCN1CCN(C(=O)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)[C@H](Cc2c[nH]c3ccccc23)C1>C1(=CC=CC=C1)C>CC(=O)CCN1CCN(C(=O)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)[C@H](Cc2c[nH]c3ccccc23)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-43d79bad5eef413a95504b9e5c6de2be | CC=O.Cl.NOCCN1CCOCC1>>ClCC=NOCCN1CCOCC1 | [OH-].[Na+].C(C)=O.Cl.Cl.N1(CCOCC1)CCON.[OH-].[Na+]>>N1(CCOCC1)CCON=CCCl | O=[CH:3][CH3:2].[ClH:1].[NH2:4][O:5][CH2:6][CH2:7][N:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1>>[Cl:1][CH2:2][CH:3]=[N:4][O:5][CH2:6][CH2:7][N:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1 | CC=O.Cl.NOCCN1CCOCC1 | ClCC=NOCCN1CCOCC1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 913217e1055d7069d7aed96a98fabb74715f4c4ada72d0d9db8ca6f5a96fd9b5 | 038d4c15acfe5b15b7a5301b924e7094df8db7d5070fa4a8cadf26ffd7ba4663 | C1COCCN1 | O=[CH;D2;+0:1]-[CH3;D1;+0:2].[C:3]-[#8:4]-[NH2;D1;+0:5].[ClH;D0;+0:6]>>[C:3]-[#8:4]-[N;H0;D2;+0:5]=[CH;D2;+0:1]-[CH2;D2;+0:2]-[Cl;H0;D1;+0:6] | 100 | [{"value": 100.0, "product": "N1(CCOCC1)CCON=CCCl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of acetaldehyde (0.1 mL of a 50 wt % soln. in water), O-[2-((morpholin-4-yl))ethyl]hydroxylamine dihydrochloride (0.14 g), NaOH (2N, 0.64 mL) and water (5 mL) was stirred at room temperature overnight. The solution was made basic with NaOH (1N) and extracted with dichloromethane. The organic layer was dried (... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Primary halide | null | null | C1COCC[NH]1 | HO- | O | null | null | CC=O.Cl.NOCCN1CCOCC1>O>ClCC=NOCCN1CCOCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f898d1d16b634156866bfd923aef5933 | C=CCN1CCOCC1.O=[N+]([O-])CCOC1CCCCO1>>C1CCC(OCC2=NOC(CN3CCOCC3)C2)OC1 | C(C=C)N1CCOCC1.[N+](=O)([O-])CCOC1OCCCC1.C1(=CC=CC=C1)N=C=O.C(C)N(CC)CC>>O1C(CCCC1)OCC1=NOC(C1)CN1CCOCC1 | [CH:10]([CH2:11][N:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1)=[CH2:18].O=[N+:8]([CH2:7][CH2:6][O:5][CH:4]1[CH2:3][CH2:2][CH2:1][CH2:20][O:19]1)[O-:9]>>[CH2:1]1[CH2:2][CH2:3][CH:4]([O:5][CH2:6][C:7]2=[N:8][O:9][CH:10]([CH2:11][N:12]3[CH2:13][CH2:14][O:15][CH2:16][CH2:17]3)[CH2:18]2)[O:19][CH2:20]1 | C=CCN1CCOCC1.O=[N+]([O-])CCOC1CCCCO1 | C1CCC(OCC2=NOC(CN3CCOCC3)C2)OC1 | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | 2a994cb4d498df9f93b581f57c7601b9bafa02ab013d3808b29fd4e0e1826f5d | 9c69a8da942d5e7fc644d8c71ab2b9598ac1e6a3adfbb0274433c184605b15b5 | C1CCC(OCC2=NOC(CN3CCOCC3)C2)OC1 | O=[N+;H0;D3:1](-[O-;H0;D1:2])-[CH2;D2;+0:3]-[C:4]-[#8:5].[#7:6]-[C:7]-[CH;D2;+0:8]=[CH2;D1;+0:9]>>[#7:6]-[C:7]-[CH;D3;+0:8]1-[CH2;D2;+0:9]-[C;H0;D3;+0:3](-[C:4]-[#8:5])=[N;H0;D2;+0:1]-[O;H0;D2;+0:2]-1 | 44.3 | [{"value": 44.0, "product": "O1C(CCCC1)OCC1=NOC(C1)CN1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.3, "product": "O1C(CCCC1)OCC1=NOC(C1)CN1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 55 | CELSIUS | null | null | To a solution of N-allylmorpholine (0.76 g, 5.0 mmol) in toluene (10 mL) was added 2-(2-nitroethoxy)tetrahydropyran (1.34 g, 7.7 mmol), phenylisocyanate (2:43 g, 20.1 mmol), and triethylamine (52 mg; 0.5 mmol). The resulting mixture was heated at 55° C. overnight. After cooling to room temperature the formed precipitat... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Allyl | null | null | C1=NOCC1 | C1CCOCC1.C1=NOCC1.C1COCC[NH]1 | HO- | C1(=CC=CC=C1)C | 55 | null | C=CCN1CCOCC1.O=[N+]([O-])CCOC1CCCCO1>C1(=CC=CC=C1)C>C1CCC(OCC2=NOC(CN3CCOCC3)C2)OC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d64a33a850374f16bffd91ecddd6d0c9 | C1CCC(OCC2=NOC(CN3CCOCC3)C2)OC1>>OCC1=NOC(CN2CCOCC2)C1 | O1C(CCCC1)OCC1=NOC(C1)CN1CCOCC1.C1(=CC=C(C=C1)S(=O)(=O)[O-])C.[NH+]1=CC=CC=C1>>N1(CCOCC1)CC1CC(=NO1)CO | C1CCC([O:1][CH2:2][C:3]2=[N:4][O:5][CH:6]([CH2:7][N:8]3[CH2:9][CH2:10][O:11][CH2:12][CH2:13]3)[CH2:14]2)OC1>>[OH:1][CH2:2][C:3]1=[N:4][O:5][CH:6]([CH2:7][N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[CH2:14]1 | C1CCC(OCC2=NOC(CN3CCOCC3)C2)OC1 | OCC1=NOC(CN2CCOCC2)C1 | null | null | CO | Reduction | Ether cleavage to primary alcohol | 69ac283008defddd09d640f7879e86f66dd29371b5c835a2facf24163ef14e9f | a4561cbdd42f56679299e19ea8b11070a39a15f6a95fb8a877e677f11b7ff57f | C1=NOC(CN2CCOCC2)C1 | [#7:1]=[C:2]-[C:3]-[O;H0;D2;+0:4]-C1-C-C-C-C-O-1>>[#7:1]=[C:2]-[C:3]-[OH;D1;+0:4] | 95 | [{"value": 95.0, "product": "N1(CCOCC1)CC1CC(=NO1)CO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of [5-((morpholin-4-yl)methyl)-4,5-dihydro-isoxazol-3-yl]methyl 2-tetrahydropyranyl ether (0.63 g) with pyridinium p-toluenesulfonate (10 mol %) in methanol was heated under reflux for 24 h. After cooling to room temperature the solvent was removed in vacuo and the residue purified by flash chromatography (Si... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Primary alcohol | C1CCOCC1 | null | C1=NOCC1.C1COCC[NH]1 | HO- | CO | null | null | C1CCC(OCC2=NOC(CN3CCOCC3)C2)OC1>CO>OCC1=NOC(CN2CCOCC2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-71ad9a67baf44ed6bce3a9333c8c2b29 | c1c(COC2CCCCO2)noc1CN1CCOCC1>>OCc1cc(CN2CCOCC2)on1 | O1C(CCCC1)OCC1=NOC(=C1)CN1CCOCC1.Cl.C(=O)([O-])[O-].[K+].[K+]>>N1(CCOCC1)CC1=CC(=NO1)CO | C1CCC([O:1][CH2:2][c:3]2[cH:4][c:5]([CH2:6][N:7]3[CH2:8][CH2:9][O:10][CH2:11][CH2:12]3)[o:13][n:14]2)OC1>>[OH:1][CH2:2][c:3]1[cH:4][c:5]([CH2:6][N:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[o:13][n:14]1 | c1c(COC2CCCCO2)noc1CN1CCOCC1 | OCc1cc(CN2CCOCC2)on1 | null | null | CO | Reduction | Ether cleavage to primary alcohol | 69ac283008defddd09d640f7879e86f66dd29371b5c835a2facf24163ef14e9f | a4561cbdd42f56679299e19ea8b11070a39a15f6a95fb8a877e677f11b7ff57f | c1cc(CN2CCOCC2)on1 | [#8;a:1]:[#7;a:2]:[c:3]-[C:4]-[O;H0;D2;+0:5]-C1-C-C-C-C-O-1>>[#8;a:1]:[#7;a:2]:[c:3]-[C:4]-[OH;D1;+0:5] | 53 | [{"value": 53.0, "product": "N1(CCOCC1)CC1=CC(=NO1)CO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | [5-((morpholin-4-yl)methyl)isoxazol-3-yl]methyl 2-tetrahydropyranyl ether (1.0 g) was dissolved in methanol (2 mL) and treated with 1 M HCl (aq. 10 mL). The mixture was stirred at room temperature for 1 h, then basified with K2CO3, and extracted with dichloromethane. The organic layers were dried (Na2SO4), and concentr... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Primary alcohol | C1CCOCC1 | null | c1cnoc1.C1COCC[NH]1 | HO- | CO | null | 1 | c1c(COC2CCCCO2)noc1CN1CCOCC1>CO>OCc1cc(CN2CCOCC2)on1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ada8fcd0db23492da513b03733d44d67 | CS(=O)(=O)Cl.OCC1=NOC(CN2CCOCC2)C1>>CS(=O)(=O)OCC1=NOC(CN2CCOCC2)C1 | O.N1(CCOCC1)CC1CC(=NO1)CO.C(C)(C)N(CC)C(C)C.CS(=O)(=O)Cl>>CS(=O)(=O)OCC1=NOC(C1)CN1CCOCC1 | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH2:6][C:7]1=[N:8][O:9][CH:10]([CH2:11][N:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)[CH2:18]1>>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][C:7]1=[N:8][O:9][CH:10]([CH2:11][N:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)[CH2:18]1 | CS(=O)(=O)Cl.OCC1=NOC(CN2CCOCC2)C1 | CS(=O)(=O)OCC1=NOC(CN2CCOCC2)C1 | null | null | ClCCl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | C1=NOC(CN2CCOCC2)C1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[#7:5]=[C:6]-[C:7]-[OH;D1;+0:8]>>[#7:5]=[C:6]-[C:7]-[O;H0;D2;+0:8]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | null | [] | null | null | 3 | HOUR | To a solution of [5-(morpholin-4-ylmethyl)-4,5-dihydro-isoxazol-3-yl]methanol (0.38 g) in dichloromethane was added dropwise diisopropylethylamine (0.33 mL) and methanesulfonyl chloride (0.15 mL). The resulting solution was stirred at room temperature for 3 h and treated with water. The layers were separated and the or... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | C1=NOCC1.C1COCC[NH]1 | HCl | ClCCl | null | 3 | CS(=O)(=O)Cl.OCC1=NOC(CN2CCOCC2)C1>ClCCl>CS(=O)(=O)OCC1=NOC(CN2CCOCC2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7cdc52eb0f104415883f65036a3b8c9b | CC(=NO)c1ccccc1.ClCCN1CCOCC1>>CC(=NOCCN1CCOCC1)c1ccccc1 | C(C)(C1=CC=CC=C1)=NO.O.Cl.ClCCN1CCOCC1.[OH-].[Na+].O>>N1(CCOCC1)CCON=C(C)C1=CC=CC=C1 | [CH3:1][C:2](=[N:3][OH:4])[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1.Cl[CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][O:10][CH2:11][CH2:12]1>>[CH3:1][C:2](=[N:3][O:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][O:10][CH2:11][CH2:12]1)[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | CC(=NO)c1ccccc1.ClCCN1CCOCC1 | CC(=NOCCN1CCOCC1)c1ccccc1 | null | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | f17bbd9c17b3a875a5aa1550ae4713b0ba603c9d3f46ba0999fc0e89cd423a21 | 4d77d2b34a9e45ba02341fbaa1023b2e18d467b26d20c41a36320fe71f49b6cc | C(=NOCCN1CCOCC1)c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3].[C;D1;H3:4]-[C:5](-[c:6])=[#7:7]-[OH;D1;+0:8]>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:8]-[#7:7]=[C:5](-[C;D1;H3:4])-[c:6] | null | [] | 75 | CELSIUS | null | null | To a solution of acetophenone oxime (20 g) in toluene (700 mL) was added subsequently tetrabutylammonium bromide (4.77 g), water (8 mL), 4-(2-chloroethyl)morpholine hydrochloride (30.31 g) and finally 50% sodium hydroxide (aq, 52 mL). The resulting mixture was heated at 75° C. overnight. After cooling to room temperatu... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Oxime | null | null | null | C1COCC[NH]1.c1ccccc1 | HCl | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.C1(=CC=CC=C1)C | 75 | null | CC(=NO)c1ccccc1.ClCCN1CCOCC1>[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.C1(=CC=CC=C1)C>CC(=NOCCN1CCOCC1)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4894c875297347dab46acb76b5f533c2 | BrCc1ccc2ccccc2c1.CC(C)(C)OC(=O)N1CCN(Cc2ccccc2)CC1>>CC(C)(C)OC(=O)N1CCN(Cc2ccccc2)CC1Cc1ccc2ccccc2c1 | C(C)(C)(C)OC(=O)N1CCN(CC1)CC1=CC=CC=C1.CN(CCN(C)C)C.BrCC1=CC2=CC=CC=C2C=C1.C(C)(CC)[Li]>>C(C)(C)(C)OC(=O)N1C(CN(CC1)CC1=CC=CC=C1)CC1=CC2=CC=CC=C2C=C1 | Br[CH2:21][c:22]1[cH:23][cH:24][c:25]2[cH:26][cH:27][cH:28][cH:29][c:30]2[cH:31]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:19][CH2:20]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([CH2:12][c:13]2... | BrCc1ccc2ccccc2c1.CC(C)(C)OC(=O)N1CCN(Cc2ccccc2)CC1 | CC(C)(C)OC(=O)N1CCN(Cc2ccccc2)CC1Cc1ccc2ccccc2c1 | null | null | C(C)OCC | C-C Coupling | OtherReaction | 63c15bc79561e94b8f7841451bf49992502feb9daf47bbf64b9f2bb32b8e1552 | f5e5e22797736d188bba28deb76a4cee8e4fee4dca04fe24f733d2ee68a23361 | c1ccc(CN2CCNC(Cc3ccc4ccccc4c3)C2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#7:6]1-[C:7]-[C:8]-[#7:9](-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13](-[C;D1;H3:14])(-[C;D1;H3:15])-[C;D1;H3:16])-[CH2;D2;+0:17]-[C:18]-1>>[C:5]-[#7:6]1-[C:7]-[C:8]-[#7:9](-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13](-[C;D1;H3:14])(-[C;D1;H3:15])-[C;D1;H3:16])-[CH;D3;+0:17](-[CH2;D2;+0:1]... | null | [] | -70 | CELSIUS | 1 | HOUR | To a solution of 4-benzyl-piperazine-1-carboxylic acid tert-butyl ester (2 g) in diethylether (35 mL) was added tetramethylethylenediamine (1.4 mL). The resulting mixture was cooled to −70° C. and sec-butyllithium (7 mL of a 1.3 M solution) was added dropwise, after complete addition the solution was slowly warmed to −... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2ccccc2c1 | HBr | C(C)OCC | -70 | 1 | BrCc1ccc2ccccc2c1.CC(C)(C)OC(=O)N1CCN(Cc2ccccc2)CC1>C(C)OCC>CC(C)(C)OC(=O)N1CCN(Cc2ccccc2)CC1Cc1ccc2ccccc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dbc56614992c4ee4a364e93a778a758a | CC(C)(C)OC(=O)N1CCN(Cc2ccccc2)CC1Cc1ccc2ccccc2c1>>c1ccc(CN2CCNC(Cc3ccc4ccccc4c3)C2)cc1 | [OH-].[NH4+].C(C)(C)(C)OC(=O)N1C(CN(CC1)CC1=CC=CC=C1)CC1=CC2=CC=CC=C2C=C1.FC(C(=O)O)(F)F>>C(C1=CC=CC=C1)N1CC(NCC1)CC1=CC2=CC=CC=C2C=C1 | CC(C)(C)OC(=O)[N:9]1[CH2:8][CH2:7][N:6]([CH2:5][c:4]2[cH:3][cH:2][cH:1][cH:24][cH:23]2)[CH2:22][CH:10]1[CH2:11][c:12]1[cH:13][cH:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[cH:21]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][N:6]2[CH2:7][CH2:8][NH:9][CH:10]([CH2:11][c:12]3[cH:13][cH:14][c:15]4[cH:16][cH:17][cH:18][cH:19][c:20]... | CC(C)(C)OC(=O)N1CCN(Cc2ccccc2)CC1Cc1ccc2ccccc2c1 | c1ccc(CN2CCNC(Cc3ccc4ccccc4c3)C2)cc1 | null | null | ClCCl | Reduction | Boc amine deprotection | 2c25e19aee181a3c5131cfdfda27035fd54d4379a11d745dfb75d386bacfd500 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc(CN2CCNC(Cc3ccc4ccccc4c3)C2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1-[C:7]>>[C:7]-[C:6]1-[C:5]-[#7:4]-[C:3]-[C:2]-[NH;D2;+0:1]-1 | null | [] | null | null | null | null | To a solution of 4-benzyl-2-(naphthalen-2-ylmethyl)piperazine-1-carboxylic acid tert-butyl ester (0.75 g) in dichloromethane (3 mL) was added dropwise trifluoroacetic acid (3 mL). After 75 min at room temperature the mixture was poured onto ice and made basic by the addition of ammonium hydroxide (25% solution). The la... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | c1ccccc1.C1C[NH]CCN1.c1ccc2ccccc2c1 | HO- | ClCCl | null | null | CC(C)(C)OC(=O)N1CCN(Cc2ccccc2)CC1Cc1ccc2ccccc2c1>ClCCl>c1ccc(CN2CCNC(Cc3ccc4ccccc4c3)C2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f9df67df753c4067bb3d87365a9cebae | C=CCCCBr.O=C1CCCCCCN1>>C=CCCCN1CCCCCCC1=O | [H-].[Na+].N1C(CCCCCC1)=O.BrCCCC=C>>C(CCC=C)N1C(CCCCCC1)=O | Br[CH2:5][CH2:4][CH2:3][CH:2]=[CH2:1].[NH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1=[O:14]>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1=[O:14] | C=CCCCBr.O=C1CCCCCCN1 | C=CCCCN1CCCCCCC1=O | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | a6501482c90c224ad73add835aa76645ef89af20d9e7919761a172defbdf0873 | 4a6c1e88c9e8bed487b746792f88d478ff36cc235f9a217d4632e6babdebdc9a | O=C1CCCCCCN1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4]=[C;D1;H2:5].[C:6]-[C:7](=[O;D1;H0:8])-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:6]-[C:7](=[O;D1;H0:8])-[N;H0;D3;+0:9](-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4]=[C;D1;H2:5])-[C:10]-[C:11] | 94.4 | [{"value": 94.4, "product": "C(CCC=C)N1C(CCCCCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a stirred suspension of sodium hydride (0.9 g, 37.5 mmole) in dimethylformamide (50 mL) was added azocan-2-one (3.83 g, 30 mmole). The mixture was stirred at room temperature for 15 minutes, and then 5-bromo-1-pentene (5.03 g, 33.7 mmole) was added slowly. The reaction mixture was stirred at room temperature for 30 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amide | Tertiary amide | C1CCCNCCC1 | C1CCC[NH]CCC1 | C1CCC[NH]CCC1 | HBr | CN(C=O)C | null | 0.25 | C=CCCCBr.O=C1CCCCCCN1>CN(C=O)C>C=CCCCN1CCCCCCC1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-42201cf9f09346ee95bb09f0fe591bf4 | C=CCCCN1CCCCCCC1=O.[O-][I+3]([O-])([O-])[O-]>>O=CCCCN1CCCCCCC1=O | I(=O)(=O)(=O)[O-].[Na+].C(CCC=C)N1C(CCCCCC1)=O>>O=C1N(CCCCCC1)CCCC=O | C=[CH:2][CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1=[O:14].[O-][I+3]([O-])([O-])[O-:1]>>[O:1]=[CH:2][CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1=[O:14] | C=CCCCN1CCCCCCC1=O.[O-][I+3]([O-])([O-])[O-] | O=CCCCN1CCCCCCC1=O | null | [Os](=O)(=O)(=O)=O | O.O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | b16cdbf18e0a0961ab3e2390d6e4aee8b329f7136e9bd1c8a4c806ff7a76d090 | c8848c7c3d9cc0904f82fae046e80cc577adb0f636b4d050e73f85888c0c7f1d | O=C1CCCCCCN1 | C=[CH;D2;+0:1]-[C:2]-[C:3].[O-;H0;D1:4]-[I+3](-[O-])(-[O-])-[O-]>>[C:3]-[C:2]-[CH;D2;+0:1]=[O;H0;D1;+0:4] | 0 | [{"value": 0.0, "product": "O=C1N(CCCCCC1)CCCC=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | Osmium tetroxide (17 mg, 0.07 mmole) was added to 1-pent-4-enyl-azocan-2-one (5.52 g, 28.3 mmole) in a mixture of tetrahydrofuran (100 mL) and water (50 mL) under ambient water bath cooling. The mixture was stirred for 5 minutes and solid sodium periodate (15.11 g, 70.65 mmole) was added in portions over 15 minutes. Th... | 10.6084/m9.figshare.5104873.v1 | null | Allyl | Aldehyde | null | null | C1CCC[NH]CCC1 | HI | [Os](=O)(=O)(=O)=O.O.O1CCCC1 | null | 0.083333 | C=CCCCN1CCCCCCC1=O.[O-][I+3]([O-])([O-])[O-]>[Os](=O)(=O)(=O)=O.O.O1CCCC1>O=CCCCN1CCCCCCC1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-714be3d82a8d46d68013a9111ce589f1 | CC(C)(C)OC(=O)N1CCNC(=O)CC1.COC(CCCBr)OC>>COC(CCCN1CCN(C(=O)OC(C)(C)C)CCC1=O)OC | COC(CCCBr)OC.[H-].[Na+].C(C)(C)(C)OC(=O)N1CCNC(CC1)=O>>C(C)(C)(C)OC(=O)N1CCN(C(CC1)=O)CCCC(OC)OC | [NH:7]1[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:18][CH2:19][C:20]1=[O:21].Br[CH2:6][CH2:5][CH2:4][CH:3]([O:2][CH3:1])[O:22][CH3:23]>>[CH3:1][O:2][CH:3]([CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:18][CH2:19][C:20]1... | CC(C)(C)OC(=O)N1CCNC(=O)CC1.COC(CCCBr)OC | COC(CCCN1CCN(C(=O)OC(C)(C)C)CCC1=O)OC | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b2bb5dea609fa2873c518376967e3df1f5bc9928b5057681df612f05993b7b1c | 4a6c1e88c9e8bed487b746792f88d478ff36cc235f9a217d4632e6babdebdc9a | O=C1CCNCCN1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8](=[O;D1;H0:9])-[C:10]>>[#7:4]-[C:5]-[C:6]-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[C:2]-[C:3])-[C:8](=[O;D1;H0:9])-[C:10] | 51.8 | [{"value": 51.8, "product": "C(C)(C)(C)OC(=O)N1CCN(C(CC1)=O)CCCC(OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 15 | MINUTE | To a suspension of 60% sodium hydride in mineral oil (0.2 g, 5 mmole) in N,N-dimethylformamide (6 mL) was added 5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester (1.0 g, 4.67 mmole). The reaction mixture was warmed at 50° C. for 5 minutes, and then at room temperature for 15 minutes. To the resulting solution was... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amide | Tertiary amide | C1C[NH]CCNC1 | C1C[NH]CC[NH]C1 | C1C[NH]CC[NH]C1 | HBr | CN(C=O)C | 50 | 0.25 | CC(C)(C)OC(=O)N1CCNC(=O)CC1.COC(CCCBr)OC>CN(C=O)C>COC(CCCN1CCN(C(=O)OC(C)(C)C)CCC1=O)OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ce360d8cda6442bfbb83adcdd193eb04 | COC(CCCN1CCN(C(=O)OC(C)(C)C)CCC1=O)OC>>CC(C)(C)OC(=O)N1CCC(=O)N(CCCC=O)CC1 | C(C)(C)(C)OC(=O)N1CCN(C(CC1)=O)CCCC(OC)OC>>C(C)(C)(C)OC(=O)N1CCN(C(CC1)=O)CCCC=O | CO[CH:17]([CH2:16][CH2:15][CH2:14][N:13]1[C:11](=[O:12])[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:20][CH2:19]1)[O:18]C>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11](=[O:12])[N:13]([CH2:14][CH2:15][CH2:16][CH:17]=[O:18])[CH2:19][CH2:20]1 | COC(CCCN1CCN(C(=O)OC(C)(C)C)CCC1=O)OC | CC(C)(C)OC(=O)N1CCC(=O)N(CCCC=O)CC1 | null | null | C(C)(=O)O | Miscellaneous | Acetal hydrolysis to aldehyde | 2c5baf4818f438d514702dbb9f9a64f069b67040aebce8bef29fab8232955599 | 84d5a69453aa750f462aa94a6bf2116fc17c5d88a9619aaa9eefb74b0c09848d | O=C1CCNCCN1 | C-O-[CH;D3;+0:1](-[C:2]-[C:3])-[O;H0;D2;+0:4]-C>>[C:3]-[C:2]-[CH;D2;+0:1]=[O;H0;D1;+0:4] | 32.9 | [{"value": 32.9, "product": "C(C)(C)(C)OC(=O)N1CCN(C(CC1)=O)CCCC=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-(4,4-dimethoxybutyl)-5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester (3 g, 9.08 mmole) in glacial acetic acid containing 0.5 mL water (10 mL) was stirred at room temperature for 24 hours. The solution was concentrated at 35° C. under reduced pressure, and the residue was partitioned between satu... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | null | null | C1C[NH]CC[NH]C1 | HO- | C(C)(=O)O | null | null | COC(CCCN1CCN(C(=O)OC(C)(C)C)CCC1=O)OC>C(C)(=O)O>CC(C)(C)OC(=O)N1CCC(=O)N(CCCC=O)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1a741121a16944648d852fb3d307e1e8 | COC(CN)OC.O=C(Cl)CCCCCl>>COC(CN1CCCCC1=O)OC | COC(CN)OC.ClCCCCC(=O)Cl.[H-].[Na+]>>COC(CN1C(CCCC1)=O)OC | [CH3:1][O:2][CH:3]([CH2:4][NH2:5])[O:12][CH3:13].Cl[CH2:6][CH2:7][CH2:8][CH2:9][C:10](Cl)=[O:11]>>[CH3:1][O:2][CH:3]([CH2:4][N:5]1[CH2:6][CH2:7][CH2:8][CH2:9][C:10]1=[O:11])[O:12][CH3:13] | COC(CN)OC.O=C(Cl)CCCCCl | COC(CN1CCCCC1=O)OC | null | null | C([O-])([O-])=O.[Na+].[Na+].C(C)(=O)OCC | Acylation | OtherReaction | 3354edba0b044d171a1214fceecabca1aaf9f7cf565d640449ee9d23da6c63d3 | 8b35e8410bcf3c8bdff4698b3ea59db09850817ec720e2e45b797eaef876f90e | O=C1CCCCN1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4]-[C;H0;D3;+0:5](-Cl)=[O;D1;H0:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[N;H0;D3;+0:9]1-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4]-[C;H0;D3;+0:5]-1=[O;D1;H0:6] | 80.9 | [{"value": 80.9, "product": "COC(CN1C(CCCC1)=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a stirred mixture of aminoacetaldehyde dimethylacetal (0.74 g, 7 mmole) in ethyl acetate (20 mL) and 2M sodium carbonate (20 mL) was added 5-chlorovaleryl chloride (1.55 g, 10 mmole). The reaction mixture was stirred at ambient temperature for 1 hour. The aqueous layer was separated and extracted with ethyl acetate.... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary halide.Primary amine | Tertiary amide | null | C1CC[NH]CC1 | C1CC[NH]CC1 | HCl | C([O-])([O-])=O.[Na+].[Na+].C(C)(=O)OCC | null | 1 | COC(CN)OC.O=C(Cl)CCCCCl>C([O-])([O-])=O.[Na+].[Na+].C(C)(=O)OCC>COC(CN1CCCCC1=O)OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6622273b486740e4aa60235c3f1f6212 | COC(CN1CCCCC1=O)OC>>O=CCN1CCCCC1=O | COC(CN1C(CCCC1)=O)OC>>O=C1N(CCCC1)CC=O | CO[CH:2]([O:1]C)[CH2:3][N:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C:9]1=[O:10]>>[O:1]=[CH:2][CH2:3][N:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C:9]1=[O:10] | COC(CN1CCCCC1=O)OC | O=CCN1CCCCC1=O | null | null | O1CCCC1 | Miscellaneous | Acetal hydrolysis to aldehyde | 2c5baf4818f438d514702dbb9f9a64f069b67040aebce8bef29fab8232955599 | 84d5a69453aa750f462aa94a6bf2116fc17c5d88a9619aaa9eefb74b0c09848d | O=C1CCCCN1 | C-O-[CH;D3;+0:1](-[C:2]-[#7:3]-[C:4]=[O;D1;H0:5])-[O;H0;D2;+0:6]-C>>[O;D1;H0:5]=[C:4]-[#7:3]-[C:2]-[CH;D2;+0:1]=[O;H0;D1;+0:6] | 86.2 | [{"value": 86.2, "product": "O=C1N(CCCC1)CC=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1-(2,2-dimethoxyethyl)-piperidin-2-one (1.06 g, 5.67 mmole) in 5% aqueous tetrahydrofuran (20 mL) was heated under reflux for 1 hour. The mixture was dried with anhydrous magnesium sulfate, filtered, and concentrated to give (2-oxo-piperidin-1-yl)-acetaldehyde (0.69 g) as a pale yellow oil.
Conditions: See... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | null | null | C1CC[NH]CC1 | HO- | O1CCCC1 | null | null | COC(CN1CCCCC1=O)OC>O1CCCC1>O=CCN1CCCCC1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9a5e82ef097e4629a01e8536961e61b4 | CCOC(CCCN)OCC.O=C(Cl)Cl.OCCCCCCl>>CCOC(CCCNC(=O)OCCCCCCl)OCC | C(=O)(Cl)Cl.ClCCCCCO.C(C)N(C1=CC=CC=C1)CC.C(C)OC(CCCN)OCC.C(C)N(CC)CC>>ClCCCCCOC(NCCCC(OCC)OCC)=O | [CH3:1][CH2:2][O:3][CH:4]([CH2:5][CH2:6][CH2:7][NH2:8])[O:18][CH2:19][CH3:20].Cl[C:9](Cl)=[O:10].[OH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][Cl:17]>>[CH3:1][CH2:2][O:3][CH:4]([CH2:5][CH2:6][CH2:7][NH:8][C:9](=[O:10])[O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][Cl:17])[O:18][CH2:19][CH3:20] | CCOC(CCCN)OCC.O=C(Cl)Cl.OCCCCCCl | CCOC(CCCNC(=O)OCCCCCCl)OCC | null | null | C(C)(=O)OCC.C1(=CC=CC=C1)C | Protection | OtherReaction | b9a97ff2417df5b07cd245547160f318b3ee4c220885157f31c57fa8ad11f8d8 | f648f3bd7738cca164e5812489428a703ee1a6f16fe0021eb651dccc8ad51d2f | null | Cl-[C;H0;D3;+0:1](-Cl)=[O;D1;H0:2].[C:3]-[C:4]-[NH2;D1;+0:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[C:4]-[C:3] | null | [] | null | null | 4 | HOUR | To an ice-cooled solution of 1.93M phosgene in toluene (31 mL, 60 mmole) was added dropwise a solution of 5-chloro-1-pentanol (4.9 g, 40 mmole) and N,N-diethylaniline (5.97 g, 40 mmole) in toluene (40 mL). The reaction mixture was stirred at ambient temperature for 4 hours. The mixture was filtered, and the filtrate wa... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary alcohol.Primary amine | Carbamic ester | null | null | null | HCl | C(C)(=O)OCC.C1(=CC=CC=C1)C | null | 4 | CCOC(CCCN)OCC.O=C(Cl)Cl.OCCCCCCl>C(C)(=O)OCC.C1(=CC=CC=C1)C>CCOC(CCCNC(=O)OCCCCCCl)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f99ea1d75d7641c585c1c205bb90d970 | CCOC(CCCNC(=O)OCCCCCCl)OCC>>CCOC(CCCN1CCCCCOC1=O)OCC | ClCCCCCOC(NCCCC(OCC)OCC)=O.[H-].[Na+]>>C(C)OC(CCCN1C(OCCCCC1)=O)OCC | Cl[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]([NH:8][CH2:7][CH2:6][CH2:5][CH:4]([O:3][CH2:2][CH3:1])[O:17][CH2:18][CH3:19])=[O:16]>>[CH3:1][CH2:2][O:3][CH:4]([CH2:5][CH2:6][CH2:7][N:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1=[O:16])[O:17][CH2:18][CH3:19] | CCOC(CCCNC(=O)OCCCCCCl)OCC | CCOC(CCCN1CCCCCOC1=O)OCC | null | null | O.CN(C=O)C.[Cl-].[Na+] | Heteroatom Alkylation and Arylation | OtherReaction | 8b3497af3376ed7b571dd7ddda21a28f2c120b189aa2d46bb10e658500f0ad03 | c05cd517c346aa4e8e8e58218c491edaea33d354b5dba9eb90dac8ad97104f73 | O=C1NCCCCCO1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:8](-[C:9]-[C:10])-[C:6](=[O;D1;H0:7])-[#8:5]-[C:4] | 16.9 | [{"value": 16.9, "product": "C(C)OC(CCCN1C(OCCCCC1)=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | HOUR | To a solution of (4,4-diethoxybutyl)carbamic acid 5-chloro-pentyl ester (11.4 g, 44 mmole) dissolved in N,N-dimethylformamide (100 mL) was added de-oiled sodium hydride (1.01 g, 42.3 mmole). The reaction mixture was stirred for 15 hours at room temperature, and then at 70° C. for 3 hours. The mixture was diluted with w... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbamic ester | Carbamic ester | null | C1CC[NH]COCC1 | C1CC[NH]COCC1 | HCl | O.CN(C=O)C.[Cl-].[Na+] | null | 15 | CCOC(CCCNC(=O)OCCCCCCl)OCC>O.CN(C=O)C.[Cl-].[Na+]>CCOC(CCCN1CCCCCOC1=O)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8668e53dc262478281808d4d95ac9c3e | CCOC(CCCN1CCCCCOC1=O)OCC>>O=CCCCN1CCCCCOC1=O | C(C)OC(CCCN1C(OCCCCC1)=O)OCC>>O=C1OCCCCCN1CCCC=O | CCO[CH:2]([O:1]CC)[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1=[O:14]>>[O:1]=[CH:2][CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1=[O:14] | CCOC(CCCN1CCCCCOC1=O)OCC | O=CCCCN1CCCCCOC1=O | null | null | O1CCCC1 | Miscellaneous | Acetal hydrolysis to aldehyde | 2c5baf4818f438d514702dbb9f9a64f069b67040aebce8bef29fab8232955599 | 84d5a69453aa750f462aa94a6bf2116fc17c5d88a9619aaa9eefb74b0c09848d | O=C1NCCCCCO1 | C-C-O-[CH;D3;+0:1](-[C:2]-[C:3])-[O;H0;D2;+0:4]-C-C>>[C:3]-[C:2]-[CH;D2;+0:1]=[O;H0;D1;+0:4] | 99.7 | [{"value": 99.7, "product": "O=C1OCCCCCN1CCCC=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3-(4,4-diethoxybutyl)-[1,3]oxazocan-2-one (2 g, 7.3 mmole) and 1.5 g Dowex 50W2-200 ion exchange resin in 3% aqueous tetrahydrofuran (30 mL) was heated under reflux for 24 hours. The mixture was filtered, and the filtrate was concentrated and dissolved in dichloromethane. The solution was dried with magnes... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | null | null | C1CC[NH]COCC1 | HO- | O1CCCC1 | null | null | CCOC(CCCN1CCCCCOC1=O)OCC>O1CCCC1>O=CCCCN1CCCCCOC1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-116343ab6f52409da190df2d18211306 | CCOC(CCN)OCC.O=C=NCCCCl>>CCOC(CCN1CCCNC1=O)OCC | C(C)OC(CCN)OCC.ClCCCN=C=O.[H-].[Na+]>>C(C)OC(CCN1C(NCCC1)=O)OCC | [CH3:1][CH2:2][O:3][CH:4]([CH2:5][CH2:6][NH2:7])[O:14][CH2:15][CH3:16].Cl[CH2:8][CH2:9][CH2:10][N:11]=[C:12]=[O:13]>>[CH3:1][CH2:2][O:3][CH:4]([CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][CH2:10][NH:11][C:12]1=[O:13])[O:14][CH2:15][CH3:16] | CCOC(CCN)OCC.O=C=NCCCCl | CCOC(CCN1CCCNC1=O)OCC | null | null | C(C)OCC | Acylation | OtherReaction | b87cf237008c975fff8ca9b74df9c720ec423d4d15e5d17e0981a8286c4d2184 | 4027078f43f05c269e15aab569503cb296a7859c76790295b091602f9a2be99b | O=C1NCCCN1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[N;H0;D2;+0:4]=[C;H0;D2;+0:5]=[O;D1;H0:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[N;H0;D3;+0:9]1-[CH2;D2;+0:1]-[C:2]-[C:3]-[NH;D2;+0:4]-[C;H0;D3;+0:5]-1=[O;D1;H0:6] | 98.2 | [{"value": 98.2, "product": "C(C)OC(CCN1C(NCCC1)=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred and ice-cooled solution of 3-aminopropionaldehyde diethylacetal (5.88 g, 40 mmole) in diethyl ether (35 mL) was added dropwise 3-chloropropyl isocyanate (4.78 g, 40 mmole). The reaction mixture was stirred at room temperature for 4 hours. The mixture was concentrated and dissolved in N,N-dimethylformamide ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Isocyanate.Primary amine | Urea | null | C1C[NH]CNC1 | C1C[NH]CNC1 | HCl | C(C)OCC | null | null | CCOC(CCN)OCC.O=C=NCCCCl>C(C)OCC>CCOC(CCN1CCCNC1=O)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-547d7a6d9ed2433382c81a9e0b373035 | CCOC(CCN1CCCNC1=O)OCC>>O=CCCN1CCCNC1=O | C(C)OC(CCN1C(NCCC1)=O)OCC>>O=C1N(CCCN1)CCC=O | CCO[CH:2]([O:1]CC)[CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][CH2:8][NH:9][C:10]1=[O:11]>>[O:1]=[CH:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][CH2:8][NH:9][C:10]1=[O:11] | CCOC(CCN1CCCNC1=O)OCC | O=CCCN1CCCNC1=O | null | null | O1CCCC1 | Miscellaneous | Acetal hydrolysis to aldehyde | 2c5baf4818f438d514702dbb9f9a64f069b67040aebce8bef29fab8232955599 | 84d5a69453aa750f462aa94a6bf2116fc17c5d88a9619aaa9eefb74b0c09848d | O=C1NCCCN1 | C-C-O-[CH;D3;+0:1](-[C:2]-[C:3])-[O;H0;D2;+0:4]-C-C>>[C:3]-[C:2]-[CH;D2;+0:1]=[O;H0;D1;+0:4] | 67.7 | [{"value": 67.7, "product": "O=C1N(CCCN1)CCC=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1-(3,3-diethoxypropyl)tetrahydropyrimidin-2-one (1 g, 4.35 mmole), and 1.0 g Dowex 50W2-200 ion exchange resin in 3% aqueous tetrahydrofuran (30 mL) was heated under reflux for 24 hours. The mixture was filtered, the filtrate was concentrated and the residue dissolved in dichloromethane (30 mL), dried with... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | null | null | C1C[NH]CNC1 | HO- | O1CCCC1 | null | null | CCOC(CCN1CCCNC1=O)OCC>O1CCCC1>O=CCCN1CCCNC1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-17af3ceeed304966aae96f3eace54d08 | C[C@H](NC(=O)OCc1ccccc1)C(=O)N1CCOCC1>>NC(=O)OCc1ccccc1 | [Mg].Cl.II.BrCCBr.BrC1=CC=C(C=C1)C(C)(C)C.BrC1=CC=C(C=C1)C(C)(C)C.[Mg].C(C)(C)[Mg]Cl.C(C1=CC=CC=C1)OC(N[C@H](C(=O)N1CCOCC1)C)=O>>C(C1=CC=CC=C1)OC(N)=O | C[C@@H](C(=O)N1CCOCC1)[NH:1][C:2](=[O:3])[O:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[NH2:1][C:2](=[O:3])[O:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1 | C[C@H](NC(=O)OCc1ccccc1)C(=O)N1CCOCC1 | NC(=O)OCc1ccccc1 | null | null | O1CCCC1.C(C)OCC | Reduction | OtherReaction | b706013ba2f1bd73452f1a01a9b15312d9da6c680befcd99935b3de42a9bdd10 | cd1c538cf3e08491aa61cba66b378b0b77a77ac72f102132120ef73abe5c5254 | c1ccccc1 | C-[C@@H](-[NH;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5])-C(=O)-N1-C-C-O-C-C-1>>[C:5]-[#8:4]-[C:2](-[NH2;D1;+0:1])=[O;D1;H0:3] | null | [] | null | null | 1 | HOUR | To a suspension of 0.85 g (34.6 mmole) magnesium turnings in 25 mL tetrahydrofuran was added 5 mL of a solution of 5 g (28.8 mmole) 1-bromo-4-tert-butylbenzene in 25 mL tetrahydrofuran. One iodine crystal and 1,2-dibromoethane (0.3 mL) was added and the mixture was heated to reflux to initiate the reaction. The rest of... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Tertiary amide | Carbamic ester | C1COCCN1 | null | c1ccccc1 | HO- | O1CCCC1.C(C)OCC | null | 1 | C[C@H](NC(=O)OCc1ccccc1)C(=O)N1CCOCC1>O1CCCC1.C(C)OCC>NC(=O)OCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-478d8c4c37604595a041594053e52ed2 | C[C@H](NC(=O)OCc1ccccc1)C(=O)c1ccc(C(C)(C)C)cc1>>C[C@@H]1NC(=O)O[C@H]1c1ccc(C(C)(C)C)cc1 | C(C1=CC=CC=C1)OC(N[C@H](C(=O)C1=CC=C(C=C1)C(C)(C)C)C)=O.CC(C)O.[BH4-].[Na+]>>C(C)(C)(C)C1=CC=C(C=C1)[C@H]1[C@@H](NC(O1)=O)C | c1ccc(CO[C:4]([NH:3][C@@H:2]([CH3:1])[C:7](=[O:6])[c:8]2[cH:9][cH:10][c:11]([C:12]([CH3:13])([CH3:14])[CH3:15])[cH:16][cH:17]2)=[O:5])cc1>>[CH3:1][C@@H:2]1[NH:3][C:4](=[O:5])[O:6][C@H:7]1[c:8]1[cH:9][cH:10][c:11]([C:12]([CH3:13])([CH3:14])[CH3:15])[cH:16][cH:17]1 | C[C@H](NC(=O)OCc1ccccc1)C(=O)c1ccc(C(C)(C)C)cc1 | C[C@@H]1NC(=O)O[C@H]1c1ccc(C(C)(C)C)cc1 | null | O | C1(=CC=CC=C1)C | Miscellaneous | OtherReaction | ce114a52a2f90c9d61769b07308248e783247fd88bada398d8a3189ee87c211c | 55be4cbb4be336004025dfc5c1cfccb8849dab585e14800dd1a52bd30d4da007 | O=C1NC[C@H](c2ccccc2)O1 | [C;D1;H3:1]-[C:2](-[#7:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-O-C-c1:c:c:c:c:c:1)-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-[c:8](:[c:9]):[c:10]>>[C;D1;H3:1]-[C:2]1-[#7:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[O;H0;D2;+0:7]-[C@H;D3;+0:6]-1-[c:8](:[c:9]):[c:10] | null | [] | null | null | 15 | HOUR | To a solution of 9 g (26.5 mmole) [(S)-2-(4-tert-butylphenyl)-1-methyl-2-oxoethyl]-carbamic acid benzyl ester o in 40 mL toluene and 10 mL 2-propanol was added dropwise a solution of 0.7 g (18.42 mmole) sodium borohydride in 2 mL water containing 1 drop 50% sodium hydroxide. The reaction mixture was stirred at room tem... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ketone.Ether | Carbamic ester.Ether | c1ccccc1 | C1COCN1 | C1COCN1.c1ccccc1 | HO- | O.C1(=CC=CC=C1)C | null | 15 | C[C@H](NC(=O)OCc1ccccc1)C(=O)c1ccc(C(C)(C)C)cc1>O.C1(=CC=CC=C1)C>C[C@@H]1NC(=O)O[C@H]1c1ccc(C(C)(C)C)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-31faa49b0a3d461488ed07797f1ebdff | CCI.C[C@@H]1NC(=O)O[C@H]1c1ccc(C(C)(C)C)cc1>>CCN1C(=O)O[C@@H](c2ccc(C(C)(C)C)cc2)[C@@H]1C | O.C(C)(C)(C)C1=CC=C(C=C1)[C@H]1[C@@H](NC(O1)=O)C.CC(C)([O-])C.[K+].ICC>>C(C)(C)(C)C1=CC=C(C=C1)[C@H]1[C@@H](N(C(O1)=O)CC)C | I[CH2:2][CH3:1].[NH:3]1[C:4](=[O:5])[O:6][C@@H:7]([c:8]2[cH:9][cH:10][c:11]([C:12]([CH3:13])([CH3:14])[CH3:15])[cH:16][cH:17]2)[C@@H:18]1[CH3:19]>>[CH3:1][CH2:2][N:3]1[C:4](=[O:5])[O:6][C@@H:7]([c:8]2[cH:9][cH:10][c:11]([C:12]([CH3:13])([CH3:14])[CH3:15])[cH:16][cH:17]2)[C@@H:18]1[CH3:19] | CCI.C[C@@H]1NC(=O)O[C@H]1c1ccc(C(C)(C)C)cc1 | CCN1C(=O)O[C@@H](c2ccc(C(C)(C)C)cc2)[C@@H]1C | null | null | CN(C=O)C.O1CCCC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 11c15b9f74bb49e6826598109b5387a19fd73a470cd23697090da8b38b3c183e | c05cd517c346aa4e8e8e58218c491edaea33d354b5dba9eb90dac8ad97104f73 | O=C1NC[C@H](c2ccccc2)O1 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[C;D1;H3:3]-[C:4]1-[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[NH;D2;+0:9]-1>>[C;D1;H3:3]-[C:4]1-[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[N;H0;D3;+0:9]-1-[CH2;D2;+0:1]-[C;D1;H3:2] | null | [] | 70 | CELSIUS | null | null | To a solution of 1 g (4.3 mmole) (4S,5S)-5-(4-tert-butylphenyl)-4-methyl-oxazolidin-2-one p in 10 mL N,N-dimethylformamide was added 5.2 mL (5.2 mmole) 1 M potassium tert-butoxide in tetrahydrofuran. To the resulting gel was added 0.4 mL (4.7 mmole) iodoethane. The reaction mixture was heated at 70° C. for 1 hr. Cold w... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbamic ester | Carbamic ester | C1COCN1 | C1COC[NH]1 | C1COC[NH]1.c1ccccc1 | HI | CN(C=O)C.O1CCCC1 | 70 | null | CCI.C[C@@H]1NC(=O)O[C@H]1c1ccc(C(C)(C)C)cc1>CN(C=O)C.O1CCCC1>CCN1C(=O)O[C@@H](c2ccc(C(C)(C)C)cc2)[C@@H]1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dc2ed7cb3777480f9d07a2be12a3c96f | C[C@@H]1NC(=O)O[C@H]1c1ccc(C(C)(C)C)cc1>>C[C@H](N)Cc1ccc(C(C)(C)C)cc1 | C(=O)[O-].[NH4+].C(C)(C)(C)C1=CC=C(C=C1)[C@H]1[C@@H](NC(O1)=O)C>>C(C)(C)(C)C1=CC=C(C=C1)C[C@H](C)N | O=C1O[C@@H:4]([c:5]2[cH:6][cH:7][c:8]([C:9]([CH3:10])([CH3:11])[CH3:12])[cH:13][cH:14]2)[C@H:2]([CH3:1])[NH:3]1>>[CH3:1][C@H:2]([NH2:3])[CH2:4][c:5]1[cH:6][cH:7][c:8]([C:9]([CH3:10])([CH3:11])[CH3:12])[cH:13][cH:14]1 | C[C@@H]1NC(=O)O[C@H]1c1ccc(C(C)(C)C)cc1 | C[C@H](N)Cc1ccc(C(C)(C)C)cc1 | null | [Pd] | CO | Reduction | OtherReaction | aa643318c572a5a8b5712432a5bf14f4edeee57a43063fb7f4322f5e355510b1 | 4e549866ec1acadec4c84aaf8495992a28ec78d8ea5ef1b9f44dd843b0dcb7d4 | c1ccccc1 | O=C1-O-[C@@H;D3;+0:1](-[c:2](:[c:3]):[c:4])-[C:5](-[C;D1;H3:6])-[NH;D2;+0:7]-1>>[C;D1;H3:6]-[C:5](-[NH2;D1;+0:7])-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | A mixture of 1 g (4.3 mmole)(4S,5S)-5-(4-tert-butylphenyl)-4-methyl-oxazolidin-2-one p(see preparation 4, step 2), 2 g (31.74 mmole) ammonium formate and 0.1 g 10% palladium on carbon in 25 mL methanol was heated under reflux for 2 hrs. The mixture was filtered and the filtrate was concentrated under reduced pressure. ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Primary amine | C1COCN1 | null | c1ccccc1 | Other | [Pd].CO | null | null | C[C@@H]1NC(=O)O[C@H]1c1ccc(C(C)(C)C)cc1>[Pd].CO>C[C@H](N)Cc1ccc(C(C)(C)C)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-31a4da783b4043c68d0b6b22af21068e | CCNC(C)Cc1ccc(OC)cc1.O=CCN1CCCCCC1=O>>CCN(CCN1CCCCCC1=O)C(C)Cc1ccc(OC)cc1 | COC1=CC=C(C=C1)CC(C)NCC.O=C1N(CCCCC1)CC=O.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>C(C)N(CCN1C(CCCCC1)=O)C(CC1=CC=C(C=C1)OC)C | [CH3:1][CH2:2][NH:3][CH:14]([CH3:15])[CH2:16][c:17]1[cH:18][cH:19][c:20]([O:21][CH3:22])[cH:23][cH:24]1.O=[CH:4][CH2:5][N:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1=[O:13]>>[CH3:1][CH2:2][N:3]([CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1=[O:13])[CH:14]([CH3:15])[CH2:16][c:17]1[cH:18][cH:19][c:2... | CCNC(C)Cc1ccc(OC)cc1.O=CCN1CCCCCC1=O | CCN(CCN1CCCCCC1=O)C(C)Cc1ccc(OC)cc1 | null | null | ClCCCl | Heteroatom Alkylation and Arylation | reductive amination | 6d9c60e7c47e75322fc9565d992b855788f3516a27cb14d7f9ed299e190b30d3 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | O=C1CCCCCN1CCNCCc1ccccc1 | O=[CH;D2;+0:1]-[C:2]-[#7:3]-[C:4]=[O;D1;H0:5].[C:6]-[C:7](-[C;D1;H3:8])-[NH;D2;+0:9]-[C:10]-[C;D1;H3:11]>>[C:6]-[C:7](-[C;D1;H3:8])-[N;H0;D3;+0:9](-[C:10]-[C;D1;H3:11])-[CH2;D2;+0:1]-[C:2]-[#7:3]-[C:4]=[O;D1;H0:5] | 91.9 | [{"value": 91.9, "product": "C(C)N(CCN1C(CCCCC1)=O)C(CC1=CC=C(C=C1)OC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 60 | HOUR | A mixture of [2-(4-methoxyphenyl)-1-methylethyl]ethylamine (0.53 g, 2.75 mmole), (2-oxo-azepan-1-yl)acetaldehyde (0.5 g, 3.2 mmole), and sodium triacetoxyborohydride (0.88 g, 4.1 mmole) in 1,2-dichloroethane (15 mL) was stirred at room temperature for 60 hours. The mixture was concentrated, and the residue was partitio... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | null | null | C1CCC[NH]CC1.c1ccccc1 | Other | ClCCCl | null | 60 | CCNC(C)Cc1ccc(OC)cc1.O=CCN1CCCCCC1=O>ClCCCl>CCN(CCN1CCCCCC1=O)C(C)Cc1ccc(OC)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fe0c7fc49ee3413ab10e6708513e6f34 | CCN[C@@H](C)Cc1ccc(SC)cc1.O=CCCCN1CCCOC1=O>>CCN(CCCCN1CCCOC1=O)[C@@H](C)Cc1ccc(SC)cc1 | C(C)N(CC)CC.Cl.C(C)N[C@H](CC1=CC=C(C=C1)SC)C.O=C1OCCCN1CCCC=O.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>C(C)N(CCCCN1C(OCCC1)=O)[C@H](CC1=CC=C(C=C1)SC)C | [CH3:1][CH2:2][NH:3][C@@H:15]([CH3:16])[CH2:17][c:18]1[cH:19][cH:20][c:21]([S:22][CH3:23])[cH:24][cH:25]1.O=[CH:4][CH2:5][CH2:6][CH2:7][N:8]1[CH2:9][CH2:10][CH2:11][O:12][C:13]1=[O:14]>>[CH3:1][CH2:2][N:3]([CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[CH2:9][CH2:10][CH2:11][O:12][C:13]1=[O:14])[C@@H:15]([CH3:16])[CH2:17][c:18]1[c... | CCN[C@@H](C)Cc1ccc(SC)cc1.O=CCCCN1CCCOC1=O | CCN(CCCCN1CCCOC1=O)[C@@H](C)Cc1ccc(SC)cc1 | null | null | ClCCCl | Heteroatom Alkylation and Arylation | reductive amination | 6d9c60e7c47e75322fc9565d992b855788f3516a27cb14d7f9ed299e190b30d3 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | O=C1OCCCN1CCCCNCCc1ccccc1 | O=[CH;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5](-[C;D1;H3:6])-[NH;D2;+0:7]-[C:8]-[C;D1;H3:9]>>[C:4]-[C:5](-[C;D1;H3:6])-[N;H0;D3;+0:7](-[C:8]-[C;D1;H3:9])-[CH2;D2;+0:1]-[C:2]-[C:3] | null | [] | null | null | 15 | HOUR | To a suspension of ethyl-[(S)-2-(4-methylsulfanylphenyl)-1-methylethyl]-amine hydrochloride (0.25 g, 1 mmole) in 1,2-dichloroethane (10 mL) was added triethylamine (0.2 mL, 1.5 mmole). To this mixture was added 4-(2-oxo-[1,3]oxazinan-3-yl)butyraldehyde (0.18 g, 1.05 mmole) and sodium triacetoxyborohydride (0.32 g, 1.5 ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | null | null | C1C[NH]COC1.c1ccccc1 | Other | ClCCCl | null | 15 | CCN[C@@H](C)Cc1ccc(SC)cc1.O=CCCCN1CCCOC1=O>ClCCCl>CCN(CCCCN1CCCOC1=O)[C@@H](C)Cc1ccc(SC)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-305d8ec7c91040e88056b133c1815a61 | CCN(CCCCN1CCCOC1=O)[C@@H](C)Cc1ccc(SC)cc1>>CCN(CCCCN1CCCOC1=O)[C@@H](C)Cc1ccc(S(C)(=O)=O)cc1 | C([O-])([O-])=O.[Na+].[Na+].C(C)N(CCCCN1C(OCCC1)=O)[C@H](CC1=CC=C(C=C1)SC)C.S(=O)(=O)(O[O-])[O-].[K+].[K+]>>C(C)N(CCCCN1C(OCCC1)=O)[C@H](CC1=CC=C(C=C1)S(=O)(=O)C)C | [CH3:1][CH2:2][N:3]([CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[CH2:9][CH2:10][CH2:11][O:12][C:13]1=[O:14])[C@@H:15]([CH3:16])[CH2:17][c:18]1[cH:19][cH:20][c:21]([S:22][CH3:23])[cH:26][cH:27]1>>[CH3:1][CH2:2][N:3]([CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[CH2:9][CH2:10][CH2:11][O:12][C:13]1=[O:14])[C@@H:15]([CH3:16])[CH2:17][c:18]1[cH... | CCN(CCCCN1CCCOC1=O)[C@@H](C)Cc1ccc(SC)cc1 | CCN(CCCCN1CCCOC1=O)[C@@H](C)Cc1ccc(S(C)(=O)=O)cc1 | null | null | CO.O | Oxidation | OtherReaction | 20dd6d48007b4fe7cd760226f21413eb5e71e6468db112596c2e7ea4858c8ac1 | 5cedc1bf0f43f21d78a249521ecfcec19fc5ac4895c41eed0e84f0c2618149fa | O=C1OCCCN1CCCCNCCc1ccccc1 | [C;D1;H3:1]-[S;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[C;D1;H3:1]-[S;H0;D4;+0:2](=[O;D1;H0:6])(=[O;D1;H0:7])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 5 | HOUR | To an ice cooled solution of 3-(4-{ethyl-[(S)-2-(4-methylsulfanylphenyl)-1-methylethyl]amino}butyl)-[1,3]oxazinan-2-one (0.33 g, 0.9 mmole) in methanol (10 mL) was added a solution of potassium peroxymonosulfate (Oxone®) (1.22 g, 1.98 mmole) in water (10 mL). The reaction mixture was stirred at room temperature for 5 h... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfone | null | null | C1C[NH]COC1.c1ccccc1 | null | CO.O | null | 5 | CCN(CCCCN1CCCOC1=O)[C@@H](C)Cc1ccc(SC)cc1>CO.O>CCN(CCCCN1CCCOC1=O)[C@@H](C)Cc1ccc(S(C)(=O)=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bdc5153de2b34156b555000b175b2f8a | CCN[C@@H](C)Cc1ccc(S(=O)(=O)c2nccs2)cc1.O=CCCCN1CCCOCC1=O>>CCN(CCCCN1CCCOCC1=O)C(C)Cc1ccc(S(=O)(=O)c2nccs2)cc1 | C(C)N[C@H](CC1=CC=C(C=C1)S(=O)(=O)C=1SC=CN1)C.O=C1COCCCN1CCCC=O.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>C(C)N(CCCCN1C(COCCC1)=O)C(CC1=CC=C(C=C1)S(=O)(=O)C=1SC=CN1)C | [CH3:1][CH2:2][NH:3][C@@H:16]([CH3:17])[CH2:18][c:19]1[cH:20][cH:21][c:22]([S:23](=[O:24])(=[O:25])[c:26]2[n:27][cH:28][cH:29][s:30]2)[cH:31][cH:32]1.O=[CH:4][CH2:5][CH2:6][CH2:7][N:8]1[CH2:9][CH2:10][CH2:11][O:12][CH2:13][C:14]1=[O:15]>>[CH3:1][CH2:2][N:3]([CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[CH2:9][CH2:10][CH2:11][O:12... | CCN[C@@H](C)Cc1ccc(S(=O)(=O)c2nccs2)cc1.O=CCCCN1CCCOCC1=O | CCN(CCCCN1CCCOCC1=O)C(C)Cc1ccc(S(=O)(=O)c2nccs2)cc1 | null | null | ClCCCl | Heteroatom Alkylation and Arylation | reductive amination | 6d9c60e7c47e75322fc9565d992b855788f3516a27cb14d7f9ed299e190b30d3 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | O=C1COCCCN1CCCCNCCc1ccc(S(=O)(=O)c2nccs2)cc1 | O=[CH;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[C@@H;D3;+0:5](-[C:6]-[c:7])-[NH;D2;+0:8]-[C:9]-[C;D1;H3:10]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:8](-[C:9]-[C;D1;H3:10])-[CH;D3;+0:5](-[C;D1;H3:4])-[C:6]-[c:7] | null | [] | null | null | 15 | HOUR | A mixture of ethyl-{(S)-1-methyl-2-[4-(thiazole-2-sulfonyl)phenyl]ethyl}-amine (0.326 g, 1.02 mmole), 4-(3-oxo-[1,4]oxazepan-4-yl)-butyraldehyde (0.22 g, 1.2 mmole), and sodium triacetoxyborohydride (0.3 g, 1.4 mmole) in 1,2-dichloroethane (10 mL) was stirred at room temperature for 15 hours. The solvent was removed un... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | null | null | C1C[NH]CCOC1.c1ccccc1.c1cscn1 | Other | ClCCCl | null | 15 | CCN[C@@H](C)Cc1ccc(S(=O)(=O)c2nccs2)cc1.O=CCCCN1CCCOCC1=O>ClCCCl>CCN(CCCCN1CCCOCC1=O)C(C)Cc1ccc(S(=O)(=O)c2nccs2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ddc8884c55174314b2e54eb7f87c5faf | CC(C)(C)OC(=O)N1CCCN(CCCC=O)C(=O)C1.CCCN[C@@H](C)Cc1ccc(S(C)(=O)=O)cc1>>CCCN(CCCCN1CCCN(C(=O)OC(C)(C)C)CC1=O)[C@@H](C)Cc1ccc(S(C)(=O)=O)cc1 | Cl.C(CC)N[C@H](CC1=CC=C(C=C1)S(=O)(=O)C)C.C(C)(C)(C)OC(=O)N1CC(N(CCC1)CCCC=O)=O.C(C)N(CC)CC.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>C(C)(C)(C)OC(=O)N1CC(N(CCC1)CCCCN(CCC)[C@H](CC1=CC=C(C=C1)S(=O)(=O)C)C)=O | O=[CH:5][CH2:6][CH2:7][CH2:8][N:9]1[CH2:10][CH2:11][CH2:12][N:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:21][C:22]1=[O:23].[CH3:1][CH2:2][CH2:3][NH:4][C@@H:24]([CH3:25])[CH2:26][c:27]1[cH:28][cH:29][c:30]([S:31]([CH3:32])(=[O:33])=[O:34])[cH:35][cH:36]1>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][C... | CC(C)(C)OC(=O)N1CCCN(CCCC=O)C(=O)C1.CCCN[C@@H](C)Cc1ccc(S(C)(=O)=O)cc1 | CCCN(CCCCN1CCCN(C(=O)OC(C)(C)C)CC1=O)[C@@H](C)Cc1ccc(S(C)(=O)=O)cc1 | null | null | ClCCCl | Heteroatom Alkylation and Arylation | reductive amination | 6d9c60e7c47e75322fc9565d992b855788f3516a27cb14d7f9ed299e190b30d3 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | O=C1CNCCCN1CCCCNCCc1ccccc1 | O=[CH;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5](-[C;D1;H3:6])-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:4]-[C:5](-[C;D1;H3:6])-[N;H0;D3;+0:7](-[C:8]-[C:9])-[CH2;D2;+0:1]-[C:2]-[C:3] | 100 | [{"value": 100.0, "product": "C(C)(C)(C)OC(=O)N1CC(N(CCC1)CCCCN(CCC)[C@H](CC1=CC=C(C=C1)S(=O)(=O)C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 17 | HOUR | A mixture of propyl-[(S)-2-(4-methanesulfonylphenyl)-1-methylethyl]-amine hydrochoride (0.50 g, 1.7 mmole), 3-oxo-4-(4-oxobutyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester (0.5 g, 1.76 mmole), triethylamine (0.24 mL, 1.7 mmole), and sodium triacetoxyborohydride (0.54 g, 2.6 mmole) in 1,2-dichloroethane (20 mL) w... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | null | null | C1C[NH]CC[NH]C1.c1ccccc1 | Other | ClCCCl | null | 17 | CC(C)(C)OC(=O)N1CCCN(CCCC=O)C(=O)C1.CCCN[C@@H](C)Cc1ccc(S(C)(=O)=O)cc1>ClCCCl>CCCN(CCCCN1CCCN(C(=O)OC(C)(C)C)CC1=O)[C@@H](C)Cc1ccc(S(C)(=O)=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c7e7762d101746bb97da29c5d5af1395 | CCCN(CCCCN1CCCN(C(=O)OC(C)(C)C)CC1=O)[C@@H](C)Cc1ccc(S(C)(=O)=O)cc1>>CCCN(CCCCN1CCCNCC1=O)[C@@H](C)Cc1ccc(S(C)(=O)=O)cc1.Cl | C(C)(C)(C)OC(=O)N1CC(N(CCC1)CCCCN(CCC)[C@H](CC1=CC=C(C=C1)S(=O)(=O)C)C)=O.Cl.C([O-])([O-])=O.[Na+].[Na+]>>Cl.Cl.CS(=O)(=O)C1=CC=C(C=C1)C[C@H](C)N(CCCCN1C(CNCCC1)=O)CCC | CC(C)(C)OC(=O)[N:13]1[CH2:12][CH2:11][CH2:10][N:9]([CH2:8][CH2:7][CH2:6][CH2:5][N:4]([CH2:3][CH2:2][CH3:1])[C@@H:17]([CH3:18])[CH2:19][c:20]2[cH:21][cH:22][c:23]([S:24]([CH3:25])(=[O:26])=[O:27])[cH:28][cH:29]2)[C:15](=[O:16])[CH2:14]1>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[CH2:10][CH2:11][CH2:1... | CCCN(CCCCN1CCCN(C(=O)OC(C)(C)C)CC1=O)[C@@H](C)Cc1ccc(S(C)(=O)=O)cc1 | CCCN(CCCCN1CCCNCC1=O)[C@@H](C)Cc1ccc(S(C)(=O)=O)cc1.Cl | null | null | null | Miscellaneous | Boc amine deprotection | ae360fe04e4bc6e17ba8fc4822721ad766f8868f9ff0a9fc757a71072b55cfbb | c95e79e18f8ea11cf22745e0eab38cab98566b1b63e7d80ee200f4cb4f94f00c | O=C1CNCCCN1CCCCNCCc1ccccc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[#7:5](-[C:6])-[C:7](=[O;D1;H0:8])-[C:9]-1>>[C:6]-[#7:5]1-[C:4]-[C:3]-[C:2]-[NH;D2;+0:1]-[C:9]-[C:7]-1=[O;D1;H0:8] | null | [] | 50 | CELSIUS | 30 | MINUTE | A mixture of 4-(4-{[(S)-2-(4-methanesulfonylphenyl)-1-methylethyl]-propylamino}butyl)-3-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester (0.9 g, 1.75 mmole) and 3N hydrochloric acid (4 mL) was warmed to 50° C. The reaction mixture was stirred at room temperature for 30 minutes, and the pH was adjusted to 10 with s... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1C[NH]CC[NH]C1 | C1C[NH]CCNC1 | C1C[NH]CCNC1.c1ccccc1 | HO- | null | 50 | 0.5 | CCCN(CCCCN1CCCN(C(=O)OC(C)(C)C)CC1=O)[C@@H](C)Cc1ccc(S(C)(=O)=O)cc1>>CCCN(CCCCN1CCCNCC1=O)[C@@H](C)Cc1ccc(S(C)(=O)=O)cc1.Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-68ea8460471f4e48b86f2746409f0c7b | CC(C)(C)OC(=O)N1CCC(=O)N(CCCC=O)CC1.CCCN[C@@H](C)Cc1ccc(S(C)(=O)=O)cc1>>CCCN(CCCCN1CCN(C(=O)OC(C)(C)C)CCC1=O)[C@@H](C)Cc1ccc(S(C)(=O)=O)cc1 | Cl.CS(=O)(=O)C1=CC=C(C=C1)C[C@H](C)NCCC.C(C)N(CC)CC.C(C)(C)(C)OC(=O)N1CCN(C(CC1)=O)CCCC=O.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>C(C)(C)(C)OC(=O)N1CCN(C(CC1)=O)CCCCN(CCC)[C@H](CC1=CC=C(C=C1)S(=O)(=O)C)C | O=[CH:5][CH2:6][CH2:7][CH2:8][N:9]1[CH2:10][CH2:11][N:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:20][CH2:21][C:22]1=[O:23].[CH3:1][CH2:2][CH2:3][NH:4][C@@H:24]([CH3:25])[CH2:26][c:27]1[cH:28][cH:29][c:30]([S:31]([CH3:32])(=[O:33])=[O:34])[cH:35][cH:36]1>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][C... | CC(C)(C)OC(=O)N1CCC(=O)N(CCCC=O)CC1.CCCN[C@@H](C)Cc1ccc(S(C)(=O)=O)cc1 | CCCN(CCCCN1CCN(C(=O)OC(C)(C)C)CCC1=O)[C@@H](C)Cc1ccc(S(C)(=O)=O)cc1 | null | null | ClCCCl | Heteroatom Alkylation and Arylation | reductive amination | 6d9c60e7c47e75322fc9565d992b855788f3516a27cb14d7f9ed299e190b30d3 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | O=C1CCNCCN1CCCCNCCc1ccccc1 | O=[CH;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5](-[C;D1;H3:6])-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:4]-[C:5](-[C;D1;H3:6])-[N;H0;D3;+0:7](-[C:8]-[C:9])-[CH2;D2;+0:1]-[C:2]-[C:3] | 97.8 | [{"value": 97.8, "product": "C(C)(C)(C)OC(=O)N1CCN(C(CC1)=O)CCCCN(CCC)[C@H](CC1=CC=C(C=C1)S(=O)(=O)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | HOUR | A mixture of [(S)-2-(4-methanesulfonylphenyl)-1-methylethyl]-propylamine hydrochloride (2.05 g, 7.03 mmole), triethylamine (0.98 mL, 7 mmole), 5-oxo-4-(4-oxobutyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester (2.0 g, 7.03 mmole), and sodium triacetoxyborohydride (2.23 g, 10.5 mmole) in 1,2-dichloroethane (40 mL) w... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | null | null | C1C[NH]CC[NH]C1.c1ccccc1 | Other | ClCCCl | null | 15 | CC(C)(C)OC(=O)N1CCC(=O)N(CCCC=O)CC1.CCCN[C@@H](C)Cc1ccc(S(C)(=O)=O)cc1>ClCCCl>CCCN(CCCCN1CCN(C(=O)OC(C)(C)C)CCC1=O)[C@@H](C)Cc1ccc(S(C)(=O)=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3c08ce7580ee47db862cb3ee257c34e1 | CCCN(CCCCN1CCNCCC1=O)[C@@H](C)Cc1ccc(S(C)(=O)=O)cc1.O=C(Cl)c1ccno1>>CCN(CCCCN1CCN(C(=O)c2ccno2)CCC1=O)C(C)Cc1ccc(S(C)(=O)=O)cc1 | Cl.Cl.CS(=O)(=O)C1=CC=C(C=C1)C[C@H](C)N(CCCCN1CCNCCC1=O)CCC.O1N=CC=C1C(=O)Cl>>C(C)N(CCCCN1CCN(CCC1=O)C(=O)C1=CC=NO1)C(CC1=CC=C(C=C1)S(=O)(=O)C)C | C[CH2:1][CH2:2][N:3]([CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[CH2:9][CH2:10][NH:11][CH2:19][CH2:20][C:21]1=[O:22])[C@@H:23]([CH3:24])[CH2:25][c:26]1[cH:27][cH:28][c:29]([S:30]([CH3:31])(=[O:32])=[O:33])[cH:34][cH:35]1.Cl[C:12](=[O:13])[c:14]1[cH:15][cH:16][n:17][o:18]1>>[CH3:1][CH2:2][N:3]([CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[... | CCCN(CCCCN1CCNCCC1=O)[C@@H](C)Cc1ccc(S(C)(=O)=O)cc1.O=C(Cl)c1ccno1 | CCN(CCCCN1CCN(C(=O)c2ccno2)CCC1=O)C(C)Cc1ccc(S(C)(=O)=O)cc1 | null | null | O.C([O-])([O-])=O.[Na+].[Na+].C1(=CC=CC=C1)C | Acylation | OtherReaction | c5087ab4d6515fdee9f2fafb8a1a4cef63670a261dd2f06558dd18e4dcb6c3dd | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C1CCN(C(=O)c2ccno2)CCN1CCCCNCCc1ccccc1 | C-[CH2;D2;+0:1]-[C:2]-[#7:3].[O;D1;H0:4]=[C:5]1-[#7:6]-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1.Cl-[C;H0;D3;+0:12](=[O;D1;H0:13])-[c:14]1:[#8;a:15]:[#7;a:16]:[c:17]:[c:18]:1>>[#7:3]-[C:2]-[CH3;D1;+0:1].[O;D1;H0:13]=[C;H0;D3;+0:12](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:5](=[O;D1;H0:4])-[C:11]-[C:10]-1)-[c:14]1:[#8;a:15... | null | [] | null | null | 4 | HOUR | To a mixture of 4-(4-{[(S)-2-(4-methanesulfonylphenyl)-1-methylethyl]-propylamino)butyl)-[1,4]diazepan-5-one dihydrochloride (0.15 g, 0.3 mmole) in toluene (5 mL) and saturated sodium carbonate (2 mL) was added isoxazole-5-carbonyl chloride (0.04 g, 0.31 mmole). The reaction mixture was stirred at room temperature for ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | C1CNCC[NH]C1 | C1C[NH]CC[NH]C1 | C1C[NH]CC[NH]C1.c1cnoc1.c1ccccc1 | HCl | O.C([O-])([O-])=O.[Na+].[Na+].C1(=CC=CC=C1)C | null | 4 | CCCN(CCCCN1CCNCCC1=O)[C@@H](C)Cc1ccc(S(C)(=O)=O)cc1.O=C(Cl)c1ccno1>O.C([O-])([O-])=O.[Na+].[Na+].C1(=CC=CC=C1)C>CCN(CCCCN1CCN(C(=O)c2ccno2)CCC1=O)C(C)Cc1ccc(S(C)(=O)=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8cc838779d1549c48ac94421ceba2821 | CC1C(c2ccc(S(C)(=O)=O)cc2)OC(=O)N1CCCCN1CCN(C(=O)OC(C)(C)C)CCC1=O>>CC(Cc1ccc(S(C)(=O)=O)cc1)NCCCCN1CCN(C(=O)OC(C)(C)C)CCC1=O | C(=O)[O-].[K+].C(C)(C)(C)OC(=O)N1CCN(C(CC1)=O)CCCCN1C(OC(C1C)C1=CC=C(C=C1)S(=O)(=O)C)=O.C(C)(C)O>>C(C)(C)(C)OC(=O)N1CCN(C(CC1)=O)CCCCNC(CC1=CC=C(C=C1)S(=O)(=O)C)C | O=C1O[CH:3]([c:4]2[cH:5][cH:6][c:7]([S:8]([CH3:9])(=[O:10])=[O:11])[cH:12][cH:13]2)[CH:2]([CH3:1])[N:14]1[CH2:15][CH2:16][CH2:17][CH2:18][N:19]1[CH2:20][CH2:21][N:22]([C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[CH2:30][CH2:31][C:32]1=[O:33]>>[CH3:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([S:8]([CH3:9])(=[O:1... | CC1C(c2ccc(S(C)(=O)=O)cc2)OC(=O)N1CCCCN1CCN(C(=O)OC(C)(C)C)CCC1=O | CC(Cc1ccc(S(C)(=O)=O)cc1)NCCCCN1CCN(C(=O)OC(C)(C)C)CCC1=O | null | [OH-].[OH-].[Pd+2] | O | Reduction | OtherReaction | 042d2a1ef1c42d965f63cdea8ebc5e66c0a72607dbd06b8fcbfd14a749b0c09f | 20c36f41eeb07c3ba4437b51ba72e8ff3c22d0b27e7197b0e9af3127f331149f | O=C1CCNCCN1CCCCNCCc1ccccc1 | O=C1-O-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[C:5](-[C;D1;H3:6])-[N;H0;D3;+0:7]-1-[C:8]-[C:9]>>[C:9]-[C:8]-[NH;D2;+0:7]-[C:5](-[C;D1;H3:6])-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 97.8 | [{"value": 97.8, "product": "C(C)(C)(C)OC(=O)N1CCN(C(CC1)=O)CCCCNC(CC1=CC=C(C=C1)S(=O)(=O)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 10 g 4-{4-[5-(4-methanesulfonyl-phenyl)-4-methyl-2-oxo-oxazolidin-3-yl]-butyl}-5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester, 1 g of 20% palladium hydroxide on carbon, 10 ml water, and 90 ml isopropanol was stirred and heated to 50°–60° C. A solution of 3.5 g potassium formate in 5 ml water was s... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Secondary amine | C1COC[NH]1 | null | c1ccccc1.C1C[NH]CC[NH]C1 | Other | [OH-].[OH-].[Pd+2].O | null | null | CC1C(c2ccc(S(C)(=O)=O)cc2)OC(=O)N1CCCCN1CCN(C(=O)OC(C)(C)C)CCC1=O>[OH-].[OH-].[Pd+2].O>CC(Cc1ccc(S(C)(=O)=O)cc1)NCCCCN1CCN(C(=O)OC(C)(C)C)CCC1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-adf83879186b4eeab6d3dae8f4e71145 | CS(=O)(=O)Cl.OCC1CN(C(c2ccccc2)c2ccccc2)C1>>CS(=O)(=O)OCC1CN(C(c2ccccc2)c2ccccc2)C1 | CS(=O)(=O)Cl.CCN(CC)CC.C1(=CC=CC=C1)C(N1CC(C1)CO)C1=CC=CC=C1.C1(=CC=CC=C1)C(N1CC(C1)C(=O)O)C1=CC=CC=C1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>CS(=O)(=O)OCC1CN(C1)C(C1=CC=CC=C1)C1=CC=CC=C1 | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH2:6][CH:7]1[CH2:8][N:9]([CH:10]([c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[CH2:23]1>>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][CH:7]1[CH2:8][N:9]([CH:10]([c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]2[cH:18][cH:19][cH:20][cH:21][c... | CS(=O)(=O)Cl.OCC1CN(C(c2ccccc2)c2ccccc2)C1 | CS(=O)(=O)OCC1CN(C(c2ccccc2)c2ccccc2)C1 | null | null | C1CCOC1 | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | c1ccc(C(c2ccccc2)N2CCC2)cc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 85.1 | [{"value": 84.0, "product": "CS(=O)(=O)OCC1CN(C1)C(C1=CC=CC=C1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.1, "product": "CS(=O)(=O)OCC1CN(C1)C(C1=CC=CC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of 1-(diphenylmethyl)-3-(hydroxymethyl) azetidine (1 g, 3.9 mmol) [prepared by reduction of 1-(diphenylmethyl)azetidine-3-carboxylic acid (CAS No.: 36476-87-6) using LiAlH4 in refluxing THF] and Et3N (0.71 mL, 5.1 mmol) in THF (30 mL) was treated with methanesulfonyl chloride (0.36 mL, 4.7 mmol) and stirred ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | C1C[NH]C1.c1ccccc1.c1ccccc1 | HCl | C1CCOC1 | null | 2 | CS(=O)(=O)Cl.OCC1CN(C(c2ccccc2)c2ccccc2)C1>C1CCOC1>CS(=O)(=O)OCC1CN(C(c2ccccc2)c2ccccc2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f6b68d0e61a241a69a6d42d86632ab49 | O=C(Cc1ccccc1Br)c1ccc(F)cc1.O=S(=O)(CC1CNC1)c1ccc(F)cc1>>O=C(CN1CC(CS(=O)(=O)c2ccc(F)cc2)C1)c1ccc(F)cc1 | Cl.FC1=CC=C(C=C1)S(=O)(=O)CC1CNC1.CCN(CC)CC.BrC1=C(C=CC=C1)CC(=O)C1=CC=C(C=C1)F>>FC1=CC=C(C=C1)C(CN1CC(C1)CS(=O)(=O)C1=CC=C(C=C1)F)=O | Brc1ccccc1[CH2:3][C:2](=[O:1])[c:19]1[cH:20][cH:21][c:22]([F:23])[cH:24][cH:25]1.[NH:4]1[CH2:5][CH:6]([CH2:7][S:8](=[O:9])(=[O:10])[c:11]2[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]2)[CH2:18]1>>[O:1]=[C:2]([CH2:3][N:4]1[CH2:5][CH:6]([CH2:7][S:8](=[O:9])(=[O:10])[c:11]2[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]2)[CH2:18]... | O=C(Cc1ccccc1Br)c1ccc(F)cc1.O=S(=O)(CC1CNC1)c1ccc(F)cc1 | O=C(CN1CC(CS(=O)(=O)c2ccc(F)cc2)C1)c1ccc(F)cc1 | null | null | CC#N | Heteroatom Alkylation and Arylation | OtherReaction | 521b01b8e1c1fa219dfb44a809dcc9c02a39e987a83b94b351de4a6e1bc9feac | b396dbcf5c7982ac557ac75c76a919f64448c1995ec140da29d4ea8defc87a50 | O=C(CN1CC(CS(=O)(=O)c2ccccc2)C1)c1ccccc1 | Br-c1:c:c:c:c:c:1-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[C:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-1>>[O;D1;H0:3]=[C:2](-[c:4])-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:5]-[C:6]-[C:7]-1 | 68.4 | [{"value": 68.0, "product": "FC1=CC=C(C=C1)C(CN1CC(C1)CS(=O)(=O)C1=CC=C(C=C1)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.4, "product": "FC1=CC=C(C=C1)C(CN1CC(C1)CS(=O)(=O)C1=CC=C(C=C1)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A mixture of 3-{[(4-fluorophenyl)sulfonyl]methyl}azetidine hydrochloride (75 mg, 0.28 mmol) in MeCN (5 mL) was treated with Et3N (97 μL, 0.7 mmol) and 2-bromo-4′-fluorophenylacetophenone (68 mg, 0.31 mmol) and stirred for 30 min at room temperature. The reaction was evaporated and the residue dissolved in DCM and purif... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Secondary amine | Ketone.Tertiary amine | c1ccccc1.C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccccc1.c1ccccc1 | HBr | CC#N | null | 0.5 | O=C(Cc1ccccc1Br)c1ccc(F)cc1.O=S(=O)(CC1CNC1)c1ccc(F)cc1>CC#N>O=C(CN1CC(CS(=O)(=O)c2ccc(F)cc2)C1)c1ccc(F)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1c558c163b0846259c1e384d3e1982e0 | O=C(CCCCl)c1ccc(F)cc1.O=S(=O)(CC1CNC1)c1ccc(F)cc1>>O=C(CCCN1CC(CS(=O)(=O)c2ccc(F)cc2)C1)c1ccc(F)cc1 | Cl.FC1=CC=C(C=C1)S(=O)(=O)CC1CNC1.C([O-])([O-])=O.[K+].[K+].[I-].[Na+].ClCCCC(=O)C1=CC=C(C=C1)F.Cl>>Cl.FC1=CC=C(C=C1)C(CCCN1CC(C1)CS(=O)(=O)C1=CC=C(C=C1)F)=O | Cl[CH2:6][CH2:5][CH2:4][C:3](=[O:2])[c:22]1[cH:23][cH:24][c:25]([F:26])[cH:27][cH:28]1.[NH:7]1[CH2:8][CH:9]([CH2:10][S:11](=[O:12])(=[O:13])[c:14]2[cH:15][cH:16][c:17]([F:18])[cH:19][cH:20]2)[CH2:21]1>>[O:2]=[C:3]([CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH:9]([CH2:10][S:11](=[O:12])(=[O:13])[c:14]2[cH:15][cH:16][c:17]([F:18... | O=C(CCCCl)c1ccc(F)cc1.O=S(=O)(CC1CNC1)c1ccc(F)cc1 | O=C(CCCN1CC(CS(=O)(=O)c2ccc(F)cc2)C1)c1ccc(F)cc1 | null | null | CC(CC)=O.CCOC(=O)C.C(C)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 256d55b982c2e8e92cb60e3cec57ca7a4bf91dcc039917facd78d1d2ef552d78 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CCCN1CC(CS(=O)(=O)c2ccccc2)C1)c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4]=[O;D1;H0:5].[C:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-1>>[O;D1;H0:5]=[C:4]-[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:9]1-[C:6]-[C:7]-[C:8]-1 | 6.6 | [{"value": 6.6, "product": "Cl.FC1=CC=C(C=C1)C(CCCN1CC(C1)CS(=O)(=O)C1=CC=C(C=C1)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred mixture of 3-{[(4-fluorophenyl)sulfonyl]methyl}azetidine hydrochloride (150 mg, 0.56 mmol), 2-butanone (5 mL), potassium carbonate (0.25 g, 1.81 mmol), sodium iodide (20 mg, 0.13 mmol) and 4-chloro-1-(4-fluorophenyl)butan-1-one (115 μL, 0.68 mmol) was heated at reflux for 5 h under an inert atmosphere. The co... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccccc1.c1ccccc1 | HCl | CC(CC)=O.CCOC(=O)C.C(C)OCC | null | null | O=C(CCCCl)c1ccc(F)cc1.O=S(=O)(CC1CNC1)c1ccc(F)cc1>CC(CC)=O.CCOC(=O)C.C(C)OCC>O=C(CCCN1CC(CS(=O)(=O)c2ccc(F)cc2)C1)c1ccc(F)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-31271072559247c18d69d3585f821af2 | O=C(CBr)c1ccc(F)cc1.O=S(=O)(CC1CNC1)c1ccc(F)cc1F>>O=C(CN1CC(CS(=O)(=O)c2ccc(F)cc2F)C1)c1ccc(F)cc1 | Cl.Cl.FC1=C(C=CC(=C1)F)S(=O)(=O)CC1CNC1.BrCC(=O)C1=CC=C(C=C1)F.C(=O)([O-])[O-].[K+].[K+]>>Cl.FC1=C(C=CC(=C1)F)S(=O)(=O)CC1CN(C1)CC(=O)C1=CC=C(C=C1)F | Br[CH2:4][C:3](=[O:2])[c:21]1[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]1.[NH:5]1[CH2:6][CH:7]([CH2:8][S:9](=[O:10])(=[O:11])[c:12]2[cH:13][cH:14][c:15]([F:16])[cH:17][c:18]2[F:19])[CH2:20]1>>[O:2]=[C:3]([CH2:4][N:5]1[CH2:6][CH:7]([CH2:8][S:9](=[O:10])(=[O:11])[c:12]2[cH:13][cH:14][c:15]([F:16])[cH:17][c:18]2[F:19])[CH2... | O=C(CBr)c1ccc(F)cc1.O=S(=O)(CC1CNC1)c1ccc(F)cc1F | O=C(CN1CC(CS(=O)(=O)c2ccc(F)cc2F)C1)c1ccc(F)cc1 | null | null | CCOC(=O)C.O.C(C)OCC.CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 3e5213a37a85731b6f91e85b682723a05ed75993cbfc6d9bae582d021274456d | 98b92c1800516dd6f2e7ad31e751bba9f02d8a8062f38a8945939bbe90ecca84 | O=C(CN1CC(CS(=O)(=O)c2ccccc2)C1)c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[C:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-1>>[O;D1;H0:3]=[C:2](-[c:4])-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:5]-[C:6]-[C:7]-1 | 13.6 | [{"value": 13.6, "product": "Cl.FC1=C(C=CC(=C1)F)S(=O)(=O)CC1CN(C1)CC(=O)C1=CC=C(C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-{[(2,4-Difluorophenyl)sulfonyl]methyl}azetidine hydrochloride (60 mg, 0.21 mmol) and 2-bromo-1-(4-fluorophenyl)ethanone (52 mg, 0.23 mmol) were stirred together at room temperature with K2CO3 (90 mg, 0.65 mmol) in DMF (3 mL) under an inert atmosphere. Water was added to the mixture after 5.5 h and the mixture was the... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Secondary amine | Ketone.Tertiary amine | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccccc1.c1ccccc1 | HBr | CCOC(=O)C.O.C(C)OCC.CN(C)C=O | null | null | O=C(CBr)c1ccc(F)cc1.O=S(=O)(CC1CNC1)c1ccc(F)cc1F>CCOC(=O)C.O.C(C)OCC.CN(C)C=O>O=C(CN1CC(CS(=O)(=O)c2ccc(F)cc2F)C1)c1ccc(F)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e3a7ade225e3424badd2e3571973117b | Fc1ccc(S)cc1.c1ccc(C(c2ccccc2)N2CC3(CO3)C2)cc1>>OC1(CSc2ccc(F)cc2)CN(C(c2ccccc2)c2ccccc2)C1 | O.[H-].[Na+].FC1=CC=C(C=C1)S.C1(=CC=CC=C1)C(N1CC2(CO2)C1)C1=CC=CC=C1>>C1(=CC=CC=C1)C(N1CC(C1)(O)CSC1=CC=C(C=C1)F)C1=CC=CC=C1 | [SH:4][c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][cH:11]1.[O:1]1[C:2]2([CH2:3]1)[CH2:12][N:13]([CH:14]([c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1)[CH2:27]2>>[OH:1][C:2]1([CH2:3][S:4][c:5]2[cH:6][cH:7][c:8]([F:9])[cH:10][cH:11]2)[CH2:12][N:13]([CH:14]([c:15]2[cH:16][cH:17][cH:18][c... | Fc1ccc(S)cc1.c1ccc(C(c2ccccc2)N2CC3(CO3)C2)cc1 | OC1(CSc2ccc(F)cc2)CN(C(c2ccccc2)c2ccccc2)C1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | d5a662dd0995c06aa45df1df03c1eb28053fcb3a1560b780f9bc163f5f72e5d4 | ed6d45389e4a9abf8ce2ffeac129c3777e058c46420dd5391d281a8675d76fd3 | c1ccc(SCC2CN(C(c3ccccc3)c3ccccc3)C2)cc1 | [#7:1]1-[C:2]-[C:3]2(-[C:4]-1)-[CH2;D2;+0:5]-[O;H0;D2;+0:6]-2.[SH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[OH;D1;+0:6]-[C:3]1(-[CH2;D2;+0:5]-[S;H0;D2;+0:7]-[c:8](:[c:9]):[c:10])-[C:2]-[#7:1]-[C:4]-1 | 80 | [{"value": 80.0, "product": "C1(=CC=CC=C1)C(N1CC(C1)(O)CSC1=CC=C(C=C1)F)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | Sodium hydride (0.128 g of a 60% dispersion in mineral oil, 3.2 mmol) was added to a solution of 4-fluorobenzenethiol (0.29 mL, 2.7 mmol) in THF (10 mL). The resulting mixture was stirred at room temperature for 10 min and then cooled to 0° C. A solution of 5-(diphenylmethyl)-1-oxa-5-azaspiro[2.3]hexane [prepared by th... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Aromatic thiol | Tertiary alcohol.Monosulfide | C1[NH]CC12CO2 | null | c1ccccc1.C1C[NH]C1.c1ccccc1.c1ccccc1 | null | C1CCOC1 | null | 0.166667 | Fc1ccc(S)cc1.c1ccc(C(c2ccccc2)N2CC3(CO3)C2)cc1>C1CCOC1>OC1(CSc2ccc(F)cc2)CN(C(c2ccccc2)c2ccccc2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f875c6bfec5146bc8f103499ca380038 | Cc1nsc2cc(F)ccc12.ClC(Cl)(Cl)Cl.O=C(OOC(=O)c1ccccc1)c1ccccc1.O=C1CCC(=O)N1Br>>CCCC(C)C.ClCCl.Fc1ccc2c(CBr)nsc2c1 | BrN1C(CCC1=O)=O.C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O.C(Cl)(Cl)(Cl)Cl.FC1=CC2=C(C(=NS2)C)C=C1>>C(Cl)Cl.CCCC(C)C.BrCC1=NSC2=C1C=CC(=C2)F | [F:10][c:11]1[cH:12][cH:13][c:14]2[c:15]([CH3:16])[n:18][s:19][c:20]2[cH:21]1.Cl[C:8](Cl)([Cl:7])[Cl:9].O=C(OOC(=O)c1[cH:1][cH:2][cH:3][cH:4][cH:5]1)c1cc[cH:6]cc1.O=C1CCC(=O)N1[Br:17]>>[CH3:1][CH2:2][CH2:3][CH:4]([CH3:5])[CH3:6].[Cl:7][CH2:8][Cl:9].[F:10][c:11]1[cH:12][cH:13][c:14]2[c:15]([CH2:16][Br:17])[n:18][s:19][c... | Cc1nsc2cc(F)ccc12.ClC(Cl)(Cl)Cl.O=C(OOC(=O)c1ccccc1)c1ccccc1.O=C1CCC(=O)N1Br | CCCC(C)C.ClCCl.Fc1ccc2c(CBr)nsc2c1 | null | null | null | C-C Coupling | OtherReaction | bdc110b550be5f542fdc8aba16635bf7c3cf154b96ef9fce261038000b522178 | 7a38c485a63c58625712ec761a5f1bcab5a4bce5000cd13569359ef4d37b098d | c1ccc2sncc2c1 | Cl-[C;H0;D4;+0:1](-Cl)(-[Cl;D1;H0:2])-[Cl;D1;H0:3].O=C(-O-O-C(=O)-c1:c:c:[cH;D2;+0:4]:c:c:1)-c1:[cH;D2;+0:5]:[cH;D2;+0:6]:[cH;D2;+0:7]:[cH;D2;+0:8]:[cH;D2;+0:9]:1.O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:10].[CH3;D1;+0:11]-[c:12]1:[#7;a:13]:[#16;a:14]:[c:15]:[c:16]:1>>[Br;H0;D1;+0:10]-[CH2;D2;+0:11]-[c:12]1:[#7;a:13]:[#16;a:14]... | 51 | [{"value": 51.0, "product": "BrCC1=NSC2=C1C=CC(=C2)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 6-fluoro-3-methyl-1,2-benzisothiazole [prepared by the method of D. M. Fink and J. T. Strupczewski, Tetrahedron Lett., 1993, 34, 6525] (761 mg, 4.55 mmol), N-bromosuccinimide (0.89 g, 5.0 mmol) and benzoyl peroxide (102 mg (70% (w/w)), 0.29 mmol) in CCl4 (25 mL) was heated at reflux under nitrogen for 6 h.... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Trichloro group.Tertiary amide.Tertiary amide.Peroxide | Primary halide.Primary halide.Primary halide | c1ccccc1.c1ccccc1.C1CCNC1 | null | c1ccc2sncc2c1 | Other | null | null | null | Cc1nsc2cc(F)ccc12.ClC(Cl)(Cl)Cl.O=C(OOC(=O)c1ccccc1)c1ccccc1.O=C1CCC(=O)N1Br>>CCCC(C)C.ClCCl.Fc1ccc2c(CBr)nsc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-07009c0944cf4a4698a88d07fc9fee5f | Fc1ccc2c(CBr)nsc2c1.O=S(=O)(CC1CNC1)c1ccc(F)cc1>>O=S(=O)(CC1CN(Cc2nsc3cc(F)ccc23)C1)c1ccc(F)cc1 | BrCC1=NSC2=C1C=CC(=C2)F.Cl.FC1=CC=C(C=C1)S(=O)(=O)CC1CNC1.C([O-])([O-])=O.[K+].[K+]>>Cl.FC1=CC2=C(C(=NS2)CN2CC(C2)CS(=O)(=O)C2=CC=C(C=C2)F)C=C1 | Br[CH2:9][c:10]1[n:11][s:12][c:13]2[cH:14][c:15]([F:16])[cH:17][cH:18][c:19]12.[O:2]=[S:3](=[O:4])([CH2:5][CH:6]1[CH2:7][NH:8][CH2:20]1)[c:21]1[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]1>>[O:2]=[S:3](=[O:4])([CH2:5][CH:6]1[CH2:7][N:8]([CH2:9][c:10]2[n:11][s:12][c:13]3[cH:14][c:15]([F:16])[cH:17][cH:18][c:19]23)[CH2:20]... | Fc1ccc2c(CBr)nsc2c1.O=S(=O)(CC1CNC1)c1ccc(F)cc1 | O=S(=O)(CC1CN(Cc2nsc3cc(F)ccc23)C1)c1ccc(F)cc1 | null | null | CN(C)C=O.[OH-].[Na+] | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 256d55b982c2e8e92cb60e3cec57ca7a4bf91dcc039917facd78d1d2ef552d78 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=S(=O)(CC1CN(Cc2nsc3ccccc23)C1)c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[#16;a:4]:[c:5]:[c:6]:1.[C:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[#16;a:4]1:[#7;a:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:10]2-[C:7]-[C:8]-[C:9]-2):[c:6]:[c:5]:1 | 23.2 | [{"value": 23.2, "product": "Cl.FC1=CC2=C(C(=NS2)CN2CC(C2)CS(=O)(=O)C2=CC=C(C=C2)F)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | 3-Bromomethyl-6-fluoro-1,2-benzisothiazole (73 mg, 0.3 mmol) was added to a mixture of 3-{[(4-fluorophenyl)sulfonyl]methyl}azetidine hydrochloride (57 mg, 0.21 mmol) and potassium carbonate (91 mg, 0.66 mmol) in DMF (2 mL) and the resulting mixture stirred at room temperature for 18 h. The mixture was diluted with 0.5M... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccc2sncc2c1.c1ccccc1 | HBr | CN(C)C=O.[OH-].[Na+] | null | 18 | Fc1ccc2c(CBr)nsc2c1.O=S(=O)(CC1CNC1)c1ccc(F)cc1>CN(C)C=O.[OH-].[Na+]>O=S(=O)(CC1CN(Cc2nsc3cc(F)ccc23)C1)c1ccc(F)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c1acfb3adf39446d8b5e3103b040d2f4 | C=COCCCC.Cc1cc(F)ccc1Br>>CC(=O)c1ccc(F)cc1C | BrC1=C(C=C(C=C1)F)C.C(=C)OCCCC.C1(=CC=CC=C1)P(CCCP(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1.C([O-])([O-])=O.[K+].[K+]>>FC1=CC(=C(C=C1)C(C)=O)C | CCCC[O:3][CH:2]=[CH2:1].Br[c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][c:10]1[CH3:11]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][c:10]1[CH3:11] | C=COCCCC.Cc1cc(F)ccc1Br | CC(=O)c1ccc(F)cc1C | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | CCOC(=O)C.O.CN(C)C=O.Cl | Acylation | OtherReaction | 6d4b1d75b39b949b33224733500c2f90e3968d1142997dce4f8a65940dca3baf | 8ed98c81d5064e24ab07e06a601274e23869776248abc6c6c3a884dd878b065b | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C;D1;H3:5]):[c:6].C-C-C-C-[O;H0;D2;+0:7]-[CH;D2;+0:8]=[CH2;D1;+0:9]>>[C;D1;H3:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[C;H0;D3;+0:8](-[CH3;D1;+0:9])=[O;H0;D1;+0:7]):[c:2]:[c:3] | 49 | [{"value": 49.0, "product": "FC1=CC(=C(C=C1)C(C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.4, "product": "FC1=CC(=C(C=C1)C(C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | To a solution of 2-bromo-5-fluorotoluene (5 g, 26.5 mmol) in DMF (65 ml) and water (15 ml) was added butyl vinyl ether (6.6 g, 65.9 mmol), palladium acetate (0.18 g, 0.8 mmol), 1,3-bis(diphenylphosphino)propane (0.72 g, 1.75 mmol) and potassium carbonate (4.4 g, 31.8 mmol). The reaction was heated at 80° C. for 48 h un... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Vinyl | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].CCOC(=O)C.O.CN(C)C=O.Cl | 80 | null | C=COCCCC.Cc1cc(F)ccc1Br>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].CCOC(=O)C.O.CN(C)C=O.Cl>CC(=O)c1ccc(F)cc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-90d80e2f9bb54732b7ab62b6b89fce5e | Cc1cc(F)ccc1C(=O)CBr.O=S(=O)(CC1CNC1)c1ccc(F)cc1>>Cc1cc(F)ccc1C(=O)CN1CC(CS(=O)(=O)c2ccc(F)cc2)C1 | Cl.FC1=CC=C(C=C1)S(=O)(=O)CC1CNC1.CCN(CC)CC.BrCC(=O)C1=C(C=C(C=C1)F)C>>FC1=CC(=C(C=C1)C(CN1CC(C1)CS(=O)(=O)C1=CC=C(C=C1)F)=O)C | Br[CH2:11][C:9]([c:8]1[c:2]([CH3:1])[cH:3][c:4]([F:5])[cH:6][cH:7]1)=[O:10].[NH:12]1[CH2:13][CH:14]([CH2:15][S:16](=[O:17])(=[O:18])[c:19]2[cH:20][cH:21][c:22]([F:23])[cH:24][cH:25]2)[CH2:26]1>>[CH3:1][c:2]1[cH:3][c:4]([F:5])[cH:6][cH:7][c:8]1[C:9](=[O:10])[CH2:11][N:12]1[CH2:13][CH:14]([CH2:15][S:16](=[O:17])(=[O:18])... | Cc1cc(F)ccc1C(=O)CBr.O=S(=O)(CC1CNC1)c1ccc(F)cc1 | Cc1cc(F)ccc1C(=O)CN1CC(CS(=O)(=O)c2ccc(F)cc2)C1 | null | null | CC#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 3e5213a37a85731b6f91e85b682723a05ed75993cbfc6d9bae582d021274456d | 98b92c1800516dd6f2e7ad31e751bba9f02d8a8062f38a8945939bbe90ecca84 | O=C(CN1CC(CS(=O)(=O)c2ccccc2)C1)c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[C:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-1>>[O;D1;H0:3]=[C:2](-[c:4])-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:5]-[C:6]-[C:7]-1 | 56.5 | [{"value": 56.0, "product": "FC1=CC(=C(C=C1)C(CN1CC(C1)CS(=O)(=O)C1=CC=C(C=C1)F)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.5, "product": "FC1=CC(=C(C=C1)C(CN1CC(C1)CS(=O)(=O)C1=CC=C(C=C1)F)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A mixture of 3-{[(4-fluorophenyl)sulfonyl]methyl}azetidine hydrochloride (75 mg, 0.28 mmol) in MeCN (5 mL) was treated with Et3N (97 μL, 0.7 mmol) and 2-bromo-1-(4-fluoro-2-methylphenyl)ethanone (72 mg, 0.31 mmol) and stirred for 30 min at room temperature. The reaction was evaporated and the residue dissolved in DCM a... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Secondary amine | Ketone.Tertiary amine | C1CNC1 | C1C[NH]C1 | c1ccccc1.C1C[NH]C1.c1ccccc1 | HBr | CC#N | null | 0.5 | Cc1cc(F)ccc1C(=O)CBr.O=S(=O)(CC1CNC1)c1ccc(F)cc1>CC#N>Cc1cc(F)ccc1C(=O)CN1CC(CS(=O)(=O)c2ccc(F)cc2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ef56ae228a4c40cd8eb87cf6971b20ef | CS(=O)(=O)OCC1CN(C(c2ccccc2)c2ccccc2)C1.O=S([O-])c1ccccc1F>>O=S(=O)(CC1CN(C(c2ccccc2)c2ccccc2)C1)c1ccccc1F | CS(=O)(=O)OCC1CN(C1)C(C1=CC=CC=C1)C1=CC=CC=C1.FC1=C(C=CC=C1)S(=O)[O-].[Na+].[I-].[Na+]>>C1(=CC=CC=C1)C(N1CC(C1)CS(=O)(=O)C1=C(C=CC=C1)F)C1=CC=CC=C1 | CS(=O)(=O)O[CH2:4][CH:5]1[CH2:6][N:7]([CH:8]([c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2:21]1.[O-:1][S:2](=[O:3])[c:22]1[cH:23][cH:24][cH:25][cH:26][c:27]1[F:28]>>[O:1]=[S:2](=[O:3])([CH2:4][CH:5]1[CH2:6][N:7]([CH:8]([c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[c:15]2[cH:1... | CS(=O)(=O)OCC1CN(C(c2ccccc2)c2ccccc2)C1.O=S([O-])c1ccccc1F | O=S(=O)(CC1CN(C(c2ccccc2)c2ccccc2)C1)c1ccccc1F | null | null | CN(C=O)C | Functional Group Interconversion | OtherReaction | 2b73dbb34348526a0db22e181edc6481738365dcccf4a503594e8690d34b9ec8 | c3ff705cc503da2952d05ca867f3e8df813542a4156bc5b57c9c4d29fe282afd | O=S(=O)(CC1CN(C(c2ccccc2)c2ccccc2)C1)c1ccccc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]1-[C:3]-[#7:4]-[C:5]-1.[O-;H0;D1:6]-[S;H0;D3;+0:7](=[O;D1;H0:8])-[c:9](:[c:10]):[c:11]>>[O;D1;H0:8]=[S;H0;D4;+0:7](=[O;H0;D1;+0:6])(-[CH2;D2;+0:1]-[C:2]1-[C:3]-[#7:4]-[C:5]-1)-[c:9](:[c:10]):[c:11] | 36.5 | [{"value": 36.0, "product": "C1(=CC=CC=C1)C(N1CC(C1)CS(=O)(=O)C1=C(C=CC=C1)F)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 36.5, "product": "C1(=CC=CC=C1)C(N1CC(C1)CS(=O)(=O)C1=C(C=CC=C1)F)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | [1-(Diphenylmethyl)azetidin-3-yl]methyl methanesulfonate [Example 1, step 1] (3.15 g, 9.50 mmol), sodium 2-fluorobenzenesulfinate (2.65 g, 14.3 mmol) and sodium iodide (2.18 g, 14.5 mmol) were reacted in dimethylformamide (50 mL) by the procedure of Example I Step 3a to afford the title compound (1.37 g, 36%); 1H NMR (... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate | Sulfone | null | null | C1C[NH]C1.c1ccccc1.c1ccccc1.c1ccccc1 | MsOH.HO- | CN(C=O)C | null | null | CS(=O)(=O)OCC1CN(C(c2ccccc2)c2ccccc2)C1.O=S([O-])c1ccccc1F>CN(C=O)C>O=S(=O)(CC1CN(C(c2ccccc2)c2ccccc2)C1)c1ccccc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f46740ff4a414e98a0bfaed86498a7e9 | O=S(=O)(CC1CN(C(c2ccccc2)c2ccccc2)C1)c1ccccc1F>>O=S(=O)(CC1CNC1)c1ccccc1F | Cl.C1(=CC=CC=C1)C(N1CC(C1)CS(=O)(=O)C1=C(C=CC=C1)F)C1=CC=CC=C1.[H][H]>>Cl.FC1=C(C=CC=C1)S(=O)(=O)CC1CNC1 | c1ccc(C(c2ccccc2)[N:8]2[CH2:7][CH:6]([CH2:5][S:3](=[O:2])(=[O:4])[c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[F:16])[CH2:9]2)cc1>>[O:2]=[S:3](=[O:4])([CH2:5][CH:6]1[CH2:7][NH:8][CH2:9]1)[c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[F:16] | O=S(=O)(CC1CN(C(c2ccccc2)c2ccccc2)C1)c1ccccc1F | O=S(=O)(CC1CNC1)c1ccccc1F | null | [OH-].[OH-].[Pd+2] | O.C(C)O | Deprotection | Hydrogenolysis of tertiary amines | b1d315bef48d6a81e10fb4eab17bea03d13eb9363139421badf3e724cd9c125a | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | O=S(=O)(CC1CNC1)c1ccccc1 | [C:1]1-[C:2]-[N;H0;D3;+0:3](-C(-c2:c:c:c:c:c:2)-c2:c:c:c:c:c:2)-[C:4]-1>>[C:1]1-[C:2]-[NH;D2;+0:3]-[C:4]-1 | 91 | [{"value": 91.0, "product": "Cl.FC1=C(C=CC=C1)S(=O)(=O)CC1CNC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-(Diphenylmethyl)-3-{[(2-fluorophenyl)sulfonyl]methyl}azetidine (1.33 g, 3.37 mmol) was dissolved in ethanol (80 mL). The solution was diluted with 2M hydrochloric acid (1.8 mL) and water (20 mL). 20% Palladium hydroxide on carbon (0.63 g) was added and the mixture shaken on a Parr apparatus under 50 psi of hydrogen f... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.c1ccccc1.C1C[NH]C1 | C1CNC1 | C1CNC1.c1ccccc1 | Other | [OH-].[OH-].[Pd+2].O.C(C)O | null | null | O=S(=O)(CC1CN(C(c2ccccc2)c2ccccc2)C1)c1ccccc1F>[OH-].[OH-].[Pd+2].O.C(C)O>O=S(=O)(CC1CNC1)c1ccccc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f59d6193c6e348fe991b92af4f65b3da | CC(C)(C)OC(=O)N1CC(CS(=O)(=O)c2ccc(C#N)cc2)C1>>N#Cc1ccc(S(=O)(=O)CC2CNC2)cc1 | C(#N)C1=CC=C(C=C1)S(=O)(=O)CC1CN(C1)C(=O)OC(C)(C)C.Cl>>Cl.N1CC(C1)CS(=O)(=O)C1=CC=C(C#N)C=C1 | CC(C)(C)OC(=O)[N:14]1[CH2:13][CH:12]([CH2:11][S:8]([c:7]2[cH:6][cH:5][c:4]([C:3]#[N:2])[cH:17][cH:16]2)(=[O:9])=[O:10])[CH2:15]1>>[N:2]#[C:3][c:4]1[cH:5][cH:6][c:7]([S:8](=[O:9])(=[O:10])[CH2:11][CH:12]2[CH2:13][NH:14][CH2:15]2)[cH:16][cH:17]1 | CC(C)(C)OC(=O)N1CC(CS(=O)(=O)c2ccc(C#N)cc2)C1 | N#Cc1ccc(S(=O)(=O)CC2CNC2)cc1 | null | null | O1CCOCC1 | Reduction | Boc amine deprotection | 343286afc91dc16da2aad3490e802fd6b05a55674e1c7133ca7403ccd8e157ce | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=S(=O)(CC1CNC1)c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-1>>[C:3]1-[C:2]-[NH;D2;+0:1]-[C:4]-1 | null | [] | null | null | 10 | MINUTE | The foregoing tert-butyl 3-{[(4-cyanophenyl)sulfonyl]methyl}azetidine-1-carboxylate (200 mg, 0.59 mmol) was treated with 4N HCl in 1,4-dioxane and stirred for 10 minutes. The reaction was evaporated without heat to give the title compound crude as a white solid (100 mg). 1H NMR (500 MHz, CDCl3) δ 2.99–3.05 (1H, m), 3.7... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1C[NH]C1 | C1CNC1 | c1ccccc1.C1CNC1 | HO- | O1CCOCC1 | null | 0.166667 | CC(C)(C)OC(=O)N1CC(CS(=O)(=O)c2ccc(C#N)cc2)C1>O1CCOCC1>N#Cc1ccc(S(=O)(=O)CC2CNC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-945dc99b109345e4a9e046f358d68973 | N#Cc1ccc(S(=O)(=O)CC2CNC2)cc1.O=C(CBr)c1ccc(F)cc1>>N#Cc1ccc(S(=O)(=O)CC2CN(CC(=O)c3ccc(F)cc3)C2)cc1 | Cl.N1CC(C1)CS(=O)(=O)C1=CC=C(C#N)C=C1.BrCC(=O)C1=CC=C(C=C1)F>>FC1=CC=C(C=C1)C(CN1CC(C1)CS(=O)(=O)C1=CC=C(C#N)C=C1)=O | [N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([S:7](=[O:8])(=[O:9])[CH2:10][CH:11]2[CH2:12][NH:13][CH2:24]2)[cH:25][cH:26]1.Br[CH2:14][C:15](=[O:16])[c:17]1[cH:18][cH:19][c:20]([F:21])[cH:22][cH:23]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([S:7](=[O:8])(=[O:9])[CH2:10][CH:11]2[CH2:12][N:13]([CH2:14][C:15](=[O:16])[c:17]3[cH:18][cH:19... | N#Cc1ccc(S(=O)(=O)CC2CNC2)cc1.O=C(CBr)c1ccc(F)cc1 | N#Cc1ccc(S(=O)(=O)CC2CN(CC(=O)c3ccc(F)cc3)C2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 3e5213a37a85731b6f91e85b682723a05ed75993cbfc6d9bae582d021274456d | 98b92c1800516dd6f2e7ad31e751bba9f02d8a8062f38a8945939bbe90ecca84 | O=C(CN1CC(CS(=O)(=O)c2ccccc2)C1)c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[C:5]1-[C:6]-[NH;D2;+0:7]-[C:8]-1>>[O;D1;H0:3]=[C:2](-[c:4])-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[C:8]-1 | 29 | [{"value": 29.0, "product": "FC1=CC=C(C=C1)C(CN1CC(C1)CS(=O)(=O)C1=CC=C(C#N)C=C1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 2, 4-[(azetidin-3-ylmethyl)sulfonyl]benzonitrile hydrochloride (75 mg, 0.27 mmol) was reacted with 2-bromo-1-(4-fluorophenyl)ethanone. Crude product was purified on a 10 g bond elute silica cartridge using the personal flash master eluting with 0.5% MeOH/DCM to 2% MeOH/DCM to give the... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Secondary amine | Ketone.Tertiary amine | C1CNC1 | C1C[NH]C1 | c1ccccc1.C1C[NH]C1.c1ccccc1 | HBr | null | null | null | N#Cc1ccc(S(=O)(=O)CC2CNC2)cc1.O=C(CBr)c1ccc(F)cc1>>N#Cc1ccc(S(=O)(=O)CC2CN(CC(=O)c3ccc(F)cc3)C2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e5d5975d399c45f8b8ff01ba0896422c | CC(C)(C)OC(=O)N1CC(CC(=O)O)C1.CI.Fc1ccc(CCBr)c(F)c1>>COC(=O)CC1CN(CCc2ccc(F)cc2F)C1 | C(C)(C)(C)OC(=O)N1CC(C1)CC(=O)O.C([O-])([O-])=O.[K+].[K+].CI.FC1=C(CCBr)C=CC(=C1)F.C([O-])([O-])=O.[K+].[K+]>>COC(CC1CN(C1)CCC1=C(C=C(C=C1)F)F)=O | CC(C)(C)OC(=O)[N:8]1[CH2:7][CH:6]([CH2:5][C:3]([OH:2])=[O:4])[CH2:19]1.I[CH3:1].Br[CH2:9][CH2:10][c:11]1[cH:12][cH:13][c:14]([F:15])[cH:16][c:17]1[F:18]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH:6]1[CH2:7][N:8]([CH2:9][CH2:10][c:11]2[cH:12][cH:13][c:14]([F:15])[cH:16][c:17]2[F:18])[CH2:19]1 | CC(C)(C)OC(=O)N1CC(CC(=O)O)C1.CI.Fc1ccc(CCBr)c(F)c1 | COC(=O)CC1CN(CCc2ccc(F)cc2F)C1 | null | null | O.CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 61099da3cfeefa1650ca4b485118643c004879acf59b5c53ca0e22f0f55ae7ee | efeb616768eb05fb673963804ab8f1892568a2d239ae402ff8ca684a1c7dc869 | c1ccc(CCN2CCC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[c:3].C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:4]1-[C:5]-[C:6](-[C:7]-[C:8](=[O;D1;H0:9])-[OH;D1;+0:10])-[C:11]-1.I-[CH3;D1;+0:12]>>[CH3;D1;+0:12]-[O;H0;D2;+0:10]-[C:8](=[O;D1;H0:9])-[C:7]-[C:6]1-[C:5]-[N;H0;D3;+0:4](-[CH2;D2;+0:1]-[C:2]-[c:3])-[C:11]-1 | 52.2 | [{"value": 52.0, "product": "COC(CC1CN(C1)CCC1=C(C=C(C=C1)F)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.2, "product": "COC(CC1CN(C1)CCC1=C(C=C(C=C1)F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of [1-(tert-butoxycarbonyl)azetidin-3-yl]acetic acid (2 g, 9.24 mmol), potassium carbonate (1.54 g, 11.1 mmol) and methyl iodide (2.89 mL, 46.5 mmol) in N,N-dimethylformamide (30 mL) was stirred at room temperature under nitrogen overnight. The reaction mixture was diluted with water and extracted with dichlo... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbamic ester.Carboxylic acid.Ether.Boc | Ester.Tertiary amine | C1C[NH]C1 | C1C[NH]C1 | C1C[NH]C1.c1ccccc1 | HBr.I- | O.CN(C=O)C | null | 8 | CC(C)(C)OC(=O)N1CC(CC(=O)O)C1.CI.Fc1ccc(CCBr)c(F)c1>O.CN(C=O)C>COC(=O)CC1CN(CCc2ccc(F)cc2F)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2a9066dffd474d6f87e1d6731d6c6d43 | CNOC.COC(=O)CC1CN(CCc2ccc(F)cc2F)C1>>CON(OC)C(=O)CC1CN(CCc2ccc(F)cc2F)C1 | [Cl-].[NH4+].COC(CC1CN(C1)CCC1=C(C=C(C=C1)F)F)=O.Cl.CNOC.O1CCCC1.C(C)(C)[Mg]Cl>>FC1=C(C=CC(=C1)F)CCN1CC(C1)CC(=O)N(OC)OC | C[NH:3][O:4][CH3:5].[CH3:1][O:2][C:6](=[O:7])[CH2:8][CH:9]1[CH2:10][N:11]([CH2:12][CH2:13][c:14]2[cH:15][cH:16][c:17]([F:18])[cH:19][c:20]2[F:21])[CH2:22]1>>[CH3:1][O:2][N:3]([O:4][CH3:5])[C:6](=[O:7])[CH2:8][CH:9]1[CH2:10][N:11]([CH2:12][CH2:13][c:14]2[cH:15][cH:16][c:17]([F:18])[cH:19][c:20]2[F:21])[CH2:22]1 | CNOC.COC(=O)CC1CN(CCc2ccc(F)cc2F)C1 | CON(OC)C(=O)CC1CN(CCc2ccc(F)cc2F)C1 | null | null | null | Acylation | OtherReaction | d147787750807073759132276086de98566af6772417f9288b6300bf1de7801c | fa66342dd118fe5531ba6a998ac8fab92d2b0db4fd04688560eec7d04e9be0e4 | c1ccc(CCN2CCC2)cc1 | C-[NH;D2;+0:1]-[#8:2]-[C;D1;H3:3].[C:4]-[C:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-[C;D1;H3:9]>>[C:4]-[C:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[N;H0;D3;+0:1](-[#8:2]-[C;D1;H3:3])-[O;H0;D2;+0:8]-[C;D1;H3:9] | 54 | [{"value": 54.0, "product": "FC1=C(C=CC(=C1)F)CCN1CC(C1)CC(=O)N(OC)OC", "details": "PERCENTYIELD", "is_desired": false}] | -20 | CELSIUS | 30 | MINUTE | A slurry of methyl{1-[2-(2,4-difluorophenyl)ethyl]azetidin-3-yl}acetate (Step 1, 0.5 g, 1.86 mmol) and N,O-dimethylhydroxylamine hydrochloride (272 mg, 2.79 mmol) in tetrahydrofuran (4 mL) was cooled to −20° C. under nitrogen. Isopropylmagnesium chloride (2M in tetrahydrofuran, 2.79 mL, 5.57 mmol) was added dropwise, m... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine | Tertiary amide | null | null | C1C[NH]C1.c1ccccc1 | Other | null | -20 | 0.5 | CNOC.COC(=O)CC1CN(CCc2ccc(F)cc2F)C1>>CON(OC)C(=O)CC1CN(CCc2ccc(F)cc2F)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-95053423c5504bcd8ef793265d775e54 | O=C(CC1CN(CCc2ccc(F)cc2F)C1)c1ccccc1>>OC(CC1CN(CCc2ccc(F)cc2F)C1)c1ccccc1 | [BH4-].[Na+].FC1=C(C=CC(=C1)F)CCN1CC(C1)CC(=O)C1=CC=CC=C1.[BH4-].[Na+].[BH4-].[Na+].[BH4-].[Na+]>>FC1=C(C=CC(=C1)F)CCN1CC(C1)CC(O)C1=CC=CC=C1 | [O:1]=[C:2]([CH2:3][CH:4]1[CH2:5][N:6]([CH2:7][CH2:8][c:9]2[cH:10][cH:11][c:12]([F:13])[cH:14][c:15]2[F:16])[CH2:17]1)[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[OH:1][CH:2]([CH2:3][CH:4]1[CH2:5][N:6]([CH2:7][CH2:8][c:9]2[cH:10][cH:11][c:12]([F:13])[cH:14][c:15]2[F:16])[CH2:17]1)[c:18]1[cH:19][cH:20][cH:21][cH:22][cH... | O=C(CC1CN(CCc2ccc(F)cc2F)C1)c1ccccc1 | OC(CC1CN(CCc2ccc(F)cc2F)C1)c1ccccc1 | null | null | CO | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(CCC2CN(CCc3ccccc3)C2)cc1 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[c:5](:[c:6]):[c:7]>>[C:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[c:5](:[c:6]):[c:7] | null | [] | null | null | 8 | HOUR | To a solution of 2-{1-[2-(2,4-difluorophenyl)ethyl]azetidin-3-yl}-1-phenylethanone (Example 20, 41 mg, 0.117 mmol) in methanol (1 mL) under nitrogen was added sodium borohydride (8.8 mg, 0.23 mmol). The reaction was stirred at room temperature overnight. More sodium borohydride (5 mg, 0.13 mmol) was added and the react... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | C1C[NH]C1.c1ccccc1.c1ccccc1 | null | CO | null | 8 | O=C(CC1CN(CCc2ccc(F)cc2F)C1)c1ccccc1>CO>OC(CC1CN(CCc2ccc(F)cc2F)C1)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3a6d532e90c54da2b540f307a77850fe | Fc1ccc(C2CO2)c(F)c1.O=S(=O)(CC1CNC1)c1ccc(F)cc1>>O=S(=O)(CC1CN(CC(O)c2ccc(F)cc2F)C1)c1ccc(F)cc1 | Cl(=O)(=O)(=O)[O-].[Li+].C(C)N(CC)CC.Cl.FC1=CC=C(C=C1)S(=O)(=O)CC1CNC1.FC1=C(C=CC(=C1)F)C1OC1>>FC1=C(C=CC(=C1)F)C(CN1CC(C1)CS(=O)(=O)C1=CC=C(C=C1)F)O | [CH2:8]1[CH:9]([c:11]2[cH:12][cH:13][c:14]([F:15])[cH:16][c:17]2[F:18])[O:10]1.[O:1]=[S:2](=[O:3])([CH2:4][CH:5]1[CH2:6][NH:7][CH2:19]1)[c:20]1[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]1>>[O:1]=[S:2](=[O:3])([CH2:4][CH:5]1[CH2:6][N:7]([CH2:8][CH:9]([OH:10])[c:11]2[cH:12][cH:13][c:14]([F:15])[cH:16][c:17]2[F:18])[CH2:19... | Fc1ccc(C2CO2)c(F)c1.O=S(=O)(CC1CNC1)c1ccc(F)cc1 | O=S(=O)(CC1CN(CC(O)c2ccc(F)cc2F)C1)c1ccc(F)cc1 | null | null | O.C(C)#N | Heteroatom Alkylation and Arylation | Ring opening of epoxide with amine | a7c0b298a6acc834cb0b7355e6a4e22caf385837f2622d41bcbe27c3bb2ba9fd | 97e758d6c4c8255d25541eb6c6a6f62e7dc30829ea162ca3392731efabc98a65 | O=S(=O)(CC1CN(CCc2ccccc2)C1)c1ccccc1 | [C:1]1-[C:2]-[C:3]-[NH;D2;+0:4]-1.[c:5]-[C:6]1-[CH2;D2;+0:7]-[O;H0;D2;+0:8]-1>>[OH;D1;+0:8]-[C:6](-[c:5])-[CH2;D2;+0:7]-[N;H0;D3;+0:4]1-[C:1]-[C:2]-[C:3]-1 | 34.1 | [{"value": 34.0, "product": "FC1=C(C=CC(=C1)F)C(CN1CC(C1)CS(=O)(=O)C1=CC=C(C=C1)F)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 34.1, "product": "FC1=C(C=CC(=C1)F)C(CN1CC(C1)CS(=O)(=O)C1=CC=C(C=C1)F)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Triethylamine (210 μL, 1.52 mmol) was added to a stirred suspension of 3-{[(4-fluorophenyl)sulfonyl]methyl}azetidine hydrochloride (Example 1 Step 4, 270 mg, 1.02 mmol) in acetonitrile (3 mL) under nitrogen. 2-(2,4-Difluorophenyl)oxirane (WO 99/23083; 1:1 mixture of enantiomers, 238 mg, 1.52 mmol) was added followed by... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Secondary alcohol.Tertiary amine | C1CO1.C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccccc1.c1ccccc1 | null | O.C(C)#N | null | 8 | Fc1ccc(C2CO2)c(F)c1.O=S(=O)(CC1CNC1)c1ccc(F)cc1>O.C(C)#N>O=S(=O)(CC1CN(CC(O)c2ccc(F)cc2F)C1)c1ccc(F)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b174bf58a91345e78452294c1af287b0 | CCN(CC)S(F)(F)F.O=S(=O)(CC1CN(CC(O)c2ccc(F)cc2F)C1)c1ccc(F)cc1>>O=S(=O)(CC1CN(CC(F)c2ccc(F)cc2F)C1)c1ccc(F)cc1 | FC1=C(C=CC(=C1)F)C(CN1CC(C1)CS(=O)(=O)C1=CC=C(C=C1)F)O.C(C)N(CC)S(F)(F)F>>FC1=C(C=CC(=C1)F)C(CN1CC(C1)CS(=O)(=O)C1=CC=C(C=C1)F)F | CCN(CC)S(F)(F)[F:10].O[CH:9]([CH2:8][N:7]1[CH2:6][CH:5]([CH2:4][S:2](=[O:1])(=[O:3])[c:20]2[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]2)[CH2:19]1)[c:11]1[cH:12][cH:13][c:14]([F:15])[cH:16][c:17]1[F:18]>>[O:1]=[S:2](=[O:3])([CH2:4][CH:5]1[CH2:6][N:7]([CH2:8][CH:9]([F:10])[c:11]2[cH:12][cH:13][c:14]([F:15])[cH:16][c:17]2[... | CCN(CC)S(F)(F)F.O=S(=O)(CC1CN(CC(O)c2ccc(F)cc2F)C1)c1ccc(F)cc1 | O=S(=O)(CC1CN(CC(F)c2ccc(F)cc2F)C1)c1ccc(F)cc1 | null | null | ClCCl | Functional Group Interconversion | OtherReaction | e80a7bea016c089beee31f9388d37df2ce7869af28d2e334bc331140a77cbc56 | 2e01f8a2520bb2c01521f4c10ab406a1b29fe14554ff1fda976238a9b96e671b | O=S(=O)(CC1CN(CCc2ccccc2)C1)c1ccccc1 | C-C-N(-C-C)-S(-F)(-F)-[F;H0;D1;+0:1].O-[CH;D3;+0:2](-[C:3]-[#7:4])-[c:5](:[c:6]):[c:7]>>[#7:4]-[C:3]-[CH;D3;+0:2](-[F;H0;D1;+0:1])-[c:5](:[c:6]):[c:7] | 50.1 | [{"value": 50.0, "product": "FC1=C(C=CC(=C1)F)C(CN1CC(C1)CS(=O)(=O)C1=CC=C(C=C1)F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.1, "product": "FC1=C(C=CC(=C1)F)C(CN1CC(C1)CS(=O)(=O)C1=CC=C(C=C1)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A stirred suspension of the alcohol from Step 1 (130 mg, 0.33 mmol) in dichloromethane (4 mL) under nitrogen was cooled to −10° C. (Diethylamino)sulfur trifluoride (54 μL, 0.41 mmol) was added dropwise and after 30 minutes the cooling bath was removed. After a further 15 minutes, the reaction was quenched with saturate... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Tertiary amine | Secondary halide | null | null | C1C[NH]C1.c1ccccc1.c1ccccc1 | HF | ClCCl | null | 0.25 | CCN(CC)S(F)(F)F.O=S(=O)(CC1CN(CC(O)c2ccc(F)cc2F)C1)c1ccc(F)cc1>ClCCl>O=S(=O)(CC1CN(CC(F)c2ccc(F)cc2F)C1)c1ccc(F)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f183d92f09df40309c2cbbef87d5eb4a | O=Cc1csc2cc(F)ccc12.O=S(=O)(CC1CNC1)c1ccc(F)cc1>>O=S(=O)(CC1CN(Cc2csc3cc(F)ccc23)C1)c1ccc(F)cc1 | C(#N)[BH3-].[Na+].Cl.FC1=CC=C(C=C1)S(=O)(=O)CC1CNC1.FC1=CC2=C(C(=CS2)C=O)C=C1>>FC1=CC2=C(C(=CS2)CN2CC(C2)CS(=O)(=O)C2=CC=C(C=C2)F)C=C1 | O=[CH:8][c:9]1[cH:10][s:11][c:12]2[cH:13][c:14]([F:15])[cH:16][cH:17][c:18]12.[O:1]=[S:2](=[O:3])([CH2:4][CH:5]1[CH2:6][NH:7][CH2:19]1)[c:20]1[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]1>>[O:1]=[S:2](=[O:3])([CH2:4][CH:5]1[CH2:6][N:7]([CH2:8][c:9]2[cH:10][s:11][c:12]3[cH:13][c:14]([F:15])[cH:16][cH:17][c:18]23)[CH2:19]1... | O=Cc1csc2cc(F)ccc12.O=S(=O)(CC1CNC1)c1ccc(F)cc1 | O=S(=O)(CC1CN(Cc2csc3cc(F)ccc23)C1)c1ccc(F)cc1 | null | null | CO.C(C)(=O)O | Heteroatom Alkylation and Arylation | reductive amination | 20192c6d9affd2a5ab556ea63d81a76bfc2997c5960b372b0adcafd104ee6377 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | O=S(=O)(CC1CN(Cc2csc3ccccc23)C1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[#16;a:4]:[c:5]:[c:6]:1.[C:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[#16;a:4]1:[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:10]2-[C:7]-[C:8]-[C:9]-2):[c:6]:[c:5]:1 | null | [] | null | null | 4 | HOUR | Sodium cyanoborohydride (13 mg, 0.20 mmol) was added to a stirred solution of 3-{[(4-fluorophenyl)sulfonyl]methyl}azetidine hydrochloride (Example 1 Step 4, 49 mg, 0.18 mmol) and 6-fluoro-1-benzothiophene-3-carbaldehyde (36 mg, 0.20 mmol) in methanol (3 mL) and acetic acid (50 μL). The reaction was stirred at room temp... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccc2sccc2c1.c1ccccc1 | Other | CO.C(C)(=O)O | null | 4 | O=Cc1csc2cc(F)ccc12.O=S(=O)(CC1CNC1)c1ccc(F)cc1>CO.C(C)(=O)O>O=S(=O)(CC1CN(Cc2csc3cc(F)ccc23)C1)c1ccc(F)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-609ecb2da5fb437e95b142568c998f9a | O=Cc1csc2cc(Cl)ccc12.O=S(=O)(CC1CNC1)c1ccc(F)cc1>>O=S(=O)(CC1CN(Cc2csc3cc(Cl)ccc23)C1)c1ccc(F)cc1 | Cl.FC1=CC=C(C=C1)S(=O)(=O)CC1CNC1.ClC1=CC2=C(C(=CS2)C=O)C=C1>>ClC1=CC2=C(C(=CS2)CN2CC(C2)CS(=O)(=O)C2=CC=C(C=C2)F)C=C1 | O=[CH:8][c:9]1[cH:10][s:11][c:12]2[cH:13][c:14]([Cl:15])[cH:16][cH:17][c:18]12.[O:1]=[S:2](=[O:3])([CH2:4][CH:5]1[CH2:6][NH:7][CH2:19]1)[c:20]1[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]1>>[O:1]=[S:2](=[O:3])([CH2:4][CH:5]1[CH2:6][N:7]([CH2:8][c:9]2[cH:10][s:11][c:12]3[cH:13][c:14]([Cl:15])[cH:16][cH:17][c:18]23)[CH2:19... | O=Cc1csc2cc(Cl)ccc12.O=S(=O)(CC1CNC1)c1ccc(F)cc1 | O=S(=O)(CC1CN(Cc2csc3cc(Cl)ccc23)C1)c1ccc(F)cc1 | null | null | null | Heteroatom Alkylation and Arylation | reductive amination | 20192c6d9affd2a5ab556ea63d81a76bfc2997c5960b372b0adcafd104ee6377 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | O=S(=O)(CC1CN(Cc2csc3ccccc23)C1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[#16;a:4]:[c:5]:[c:6]:1.[C:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[#16;a:4]1:[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:10]2-[C:7]-[C:8]-[C:9]-2):[c:6]:[c:5]:1 | null | [] | null | null | null | null | Prepared according to the method of Example 23 using 3-{[(4-fluorophenyl)sulfonyl]methyl}azetidine hydrochloride (Example 1 Step 4) and 6-chloro-1-benzothiophene-3-carbaldehyde. 1H NMR (500 MHz, CDCl3) δ 7.92–7.88 (2H, m), 7.81 (1H, d, J=1.8 Hz), 7.72 (1H, d, J=8.5 Hz), 7.32 (1H, dd, J=1.9, 8.6 Hz), 7.26–7.22 (2H, m), ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccc2sccc2c1.c1ccccc1 | Other | null | null | null | O=Cc1csc2cc(Cl)ccc12.O=S(=O)(CC1CNC1)c1ccc(F)cc1>>O=S(=O)(CC1CN(Cc2csc3cc(Cl)ccc23)C1)c1ccc(F)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-74d2a91588d34dd391817af6046327c9 | O=C(O)c1csc2c1CCCC2>>OCc1csc2c1CCCC2 | S1C=C(C2=C1CCCC2)C(=O)O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>S1C=C(C2=C1CCCC2)CO | O=[C:2]([OH:1])[c:3]1[cH:4][s:5][c:6]2[c:7]1[CH2:8][CH2:9][CH2:10][CH2:11]2>>[OH:1][CH2:2][c:3]1[cH:4][s:5][c:6]2[c:7]1[CH2:8][CH2:9][CH2:10][CH2:11]2 | O=C(O)c1csc2c1CCCC2 | OCc1csc2c1CCCC2 | null | null | C(C)OCC | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | c1cc2c(s1)CCCC2 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[c:3]1:[c:4]:[#16;a:5]:[c:6]:[c:7]:1>>[O;D1;H1:2]-[CH2;D2;+0:1]-[c:3]1:[c:4]:[#16;a:5]:[c:6]:[c:7]:1 | 86.4 | [{"value": 86.0, "product": "S1C=C(C2=C1CCCC2)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.4, "product": "S1C=C(C2=C1CCCC2)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | A solution of 4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylic acid (400 mg, 2.2 mmol) in diethyl ether (10 mL) was added under nitrogen to lithium aluminium hydride (1M solution in tetrahydrofuran, 3 mL, 3 mmol) in diethyl ether (10 mL) dropwise over 5 minutes. The reaction was stirred at room temperature for 1.5 hour... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1cc2c(s1)CCCC2 | Other | C(C)OCC | null | 1.5 | O=C(O)c1csc2c1CCCC2>C(C)OCC>OCc1csc2c1CCCC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-68919c0526124ce58060d7db7429fb11 | OCc1csc2c1CCCC2>>O=Cc1csc2c1CCCC2 | S1C=C(C2=C1CCCC2)CO.CC(=O)OI1(C2=CC=CC=C2C(=O)O1)(OC(=O)C)OC(=O)C.C(C)OCC.[OH-].[Na+]>>S1C=C(C2=C1CCCC2)C=O | [OH:1][CH2:2][c:3]1[cH:4][s:5][c:6]2[c:7]1[CH2:8][CH2:9][CH2:10][CH2:11]2>>[O:1]=[CH:2][c:3]1[cH:4][s:5][c:6]2[c:7]1[CH2:8][CH2:9][CH2:10][CH2:11]2 | OCc1csc2c1CCCC2 | O=Cc1csc2c1CCCC2 | null | null | ClCCl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1cc2c(s1)CCCC2 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3]1:[c:4]:[#16;a:5]:[c:6]:[c:7]:1>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3]1:[c:4]:[#16;a:5]:[c:6]:[c:7]:1 | 88.6 | [{"value": 88.0, "product": "S1C=C(C2=C1CCCC2)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.6, "product": "S1C=C(C2=C1CCCC2)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | A solution of 4,5,6,7-tetrahydro-1-benzothien-3-ylmethanol (Step 1, 320 mg, 1.9 mmol) in dichloromethane (10 mL) was added to a stirred solution of 1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one (0.92 g, 2.1 mmol) in dichloromethane (10 mL) under nitrogen and stirred at room temperature for 20 minutes. Di... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1cc2c(s1)CCCC2 | null | ClCCl | null | 0.333333 | OCc1csc2c1CCCC2>ClCCl>O=Cc1csc2c1CCCC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-55636809cd184363ae45824e305f8195 | CC(=O)CSc1cccs1>>Cc1csc2sccc12 | S1C(=CC=C1)SCC(=O)C>>CC1=CSC=2SC=CC21 | O=[C:2]([CH3:1])[CH2:3][S:4][c:5]1[s:6][cH:7][cH:8][cH:9]1>>[CH3:1][c:2]1[cH:3][s:4][c:5]2[s:6][cH:7][cH:8][c:9]12 | CC(=O)CSc1cccs1 | Cc1csc2sccc12 | null | null | ClC1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 2dafaae5cd143665d21c913f39904edf1dfa82dcdd36f8e60f52cfc9fdb8de90 | d3105ed758b983bc5eb6baf94b9e9cb6323eb0855df17c0097ffd1c29264fe70 | c1cc2ccsc2s1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH2;D2;+0:3]-[S;H0;D2;+0:4]-[c:5]1:[#16;a:6]:[c:7]:[c:8]:[cH;D2;+0:9]:1>>[C;D1;H3:2]-[c;H0;D3;+0:1]1:[cH;D2;+0:3]:[s;H0;D2;+0:4]:[c:5]2:[#16;a:6]:[c:7]:[c:8]:[c;H0;D3;+0:9]:2:1 | 42 | [{"value": 42.0, "product": "CC1=CSC=2SC=CC21", "details": "PERCENTYIELD", "is_desired": false}, {"value": 41.6, "product": "CC1=CSC=2SC=CC21", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A 1M solution of 1-(2-thienylthio)acetone (2.6 g, 15.1 mmol) in chlorobenzene (15 mL) was heated to 110° C. under nitrogen and hot polyphosphoric acid (3 mL) was added. The reaction was heated to reflux overnight. The chlorobenzene layer was decanted off and further chlorobenzene (15 mL x2) was added to the polyphospho... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Monosulfide | null | c1ccsc1 | c1cc2ccsc2s1 | c1cc2ccsc2s1 | HO- | ClC1=CC=CC=C1 | null | null | CC(=O)CSc1cccs1>ClC1=CC=CC=C1>Cc1csc2sccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-012d81d01cae4b83b6deb6a888f9666b | Cc1csc2sccc12.O=C1CCC(=O)N1Br>>Cc1c(Br)sc2sccc12 | CC1=CSC=2SC=CC21.BrN1C(CCC1=O)=O.C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O>>BrC1=C(C2=C(SC=C2)S1)C | [CH3:1][c:2]1[cH:3][s:5][c:6]2[s:7][cH:8][cH:9][c:10]12.O=C1CCC(=O)N1[Br:4]>>[CH3:1][c:2]1[c:3]([Br:4])[s:5][c:6]2[s:7][cH:8][cH:9][c:10]12 | Cc1csc2sccc12.O=C1CCC(=O)N1Br | Cc1c(Br)sc2sccc12 | null | null | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Bromination | bc1620dec8144f2d3084295e3910f25a26b975707400914d59bc83324948ef04 | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1cc2ccsc2s1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#16;a:2]:[c:3]1:[#16;a:4]:[cH;D2;+0:5]:[c:6](-[C;D1;H3:7]):[c:8]:1>>[#16;a:2]:[c:3]1:[#16;a:4]:[c;H0;D3;+0:5](-[Br;H0;D1;+0:1]):[c:6](-[C;D1;H3:7]):[c:8]:1 | 37 | [{"value": 37.0, "product": "BrC1=C(C2=C(SC=C2)S1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 36.7, "product": "BrC1=C(C2=C(SC=C2)S1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-Methylthieno[2,3-b]thiophene (Step 1, 450 mg, 2.92 mmol) was dissolved in carbon tetrachloride (7 mL) under nitrogen. N-Bromosuccinimide (0.52 g, 2.92 mmol) and benzoyl peroxide (75% in water; 0.10 g, 0.29 mmol) were added and the reaction heated to reflux for 6 hours. The solvent was removed in vacuo and the residue... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1cc2ccsc2s1.C1CCNC1 | c1cc2ccsc2s1 | c1cc2ccsc2s1 | HO- | C(Cl)(Cl)(Cl)Cl | null | null | Cc1csc2sccc12.O=C1CCC(=O)N1Br>C(Cl)(Cl)(Cl)Cl>Cc1c(Br)sc2sccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-98db43d6f9f646978521d0f68346a642 | BrCc1c(Br)sc2sc(Br)cc12.O=S(=O)(CC1CNC1)c1ccc(F)cc1>>O=S(=O)(CC1CN(Cc2c(Br)sc3sc(Br)cc23)C1)c1ccc(F)cc1 | Cl.FC1=CC=C(C=C1)S(=O)(=O)CC1CNC1.BrC1=C(C2=C(SC(=C2)Br)S1)CBr>>BrC1=C(C2=C(SC(=C2)Br)S1)CN1CC(C1)CS(=O)(=O)C1=CC=C(C=C1)F | Br[CH2:8][c:9]1[c:10]([Br:11])[s:12][c:13]2[s:14][c:15]([Br:16])[cH:17][c:18]12.[O:1]=[S:2](=[O:3])([CH2:4][CH:5]1[CH2:6][NH:7][CH2:19]1)[c:20]1[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]1>>[O:1]=[S:2](=[O:3])([CH2:4][CH:5]1[CH2:6][N:7]([CH2:8][c:9]2[c:10]([Br:11])[s:12][c:13]3[s:14][c:15]([Br:16])[cH:17][c:18]23)[CH2:1... | BrCc1c(Br)sc2sc(Br)cc12.O=S(=O)(CC1CNC1)c1ccc(F)cc1 | O=S(=O)(CC1CN(Cc2c(Br)sc3sc(Br)cc23)C1)c1ccc(F)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 256d55b982c2e8e92cb60e3cec57ca7a4bf91dcc039917facd78d1d2ef552d78 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=S(=O)(CC1CN(Cc2csc3sccc23)C1)c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4](:[#16;a:5]):[#16;a:6]:[c:7]:1-[Br;D1;H0:8].[C:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-1>>[#16;a:5]:[c:4]1:[#16;a:6]:[c:7](-[Br;D1;H0:8]):[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:12]2-[C:9]-[C:10]-[C:11]-2):[c:3]:1 | null | [] | null | null | null | null | Prepared from 3-{[(4-fluorophenyl)sulfonyl]methyl}azetidine hydrochloride (Example 1 Step 4) and 2,5-dibromo-3-(bromomethyl)thieno[2,3-b]thiophene (Step 3) according to the method of Example 1 Step 5. 1H NMR (500 MHz, CDCl3) δ 7.90–7.88 (2H, m), 7.33 (1H, s), 7.26–7.23 (2H, m), 3.60 (2H, s), 3.40 (2H, t, J=7.4 Hz), 3.3... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1cc2ccsc2s1.c1ccccc1 | HBr | null | null | null | BrCc1c(Br)sc2sc(Br)cc12.O=S(=O)(CC1CNC1)c1ccc(F)cc1>>O=S(=O)(CC1CN(Cc2c(Br)sc3sc(Br)cc23)C1)c1ccc(F)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-96fd61fe2c3244a199b4f9c341d9513b | O=S(=O)(CC1CN(Cc2c(Br)sc3sc(Br)cc23)C1)c1ccc(F)cc1>>O=S(=O)(CC1CN(Cc2csc3sccc23)C1)c1ccc(F)cc1 | BrC1=C(C2=C(SC(=C2)Br)S1)CN1CC(C1)CS(=O)(=O)C1=CC=C(C=C1)F.[H][H]>>FC1=CC=C(C=C1)S(=O)(=O)CC1CN(C1)CC1=CSC=2SC=CC21 | Br[c:10]1[c:9]([CH2:8][N:7]2[CH2:6][CH:5]([CH2:4][S:2](=[O:1])(=[O:3])[c:18]3[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]3)[CH2:17]2)[c:16]2[c:12]([s:11]1)[s:13][c:14](Br)[cH:15]2>>[O:1]=[S:2](=[O:3])([CH2:4][CH:5]1[CH2:6][N:7]([CH2:8][c:9]2[cH:10][s:11][c:12]3[s:13][cH:14][cH:15][c:16]23)[CH2:17]1)[c:18]1[cH:19][cH:20][... | O=S(=O)(CC1CN(Cc2c(Br)sc3sc(Br)cc23)C1)c1ccc(F)cc1 | O=S(=O)(CC1CN(Cc2csc3sccc23)C1)c1ccc(F)cc1 | null | [Pd] | CO | Reduction | OtherReaction | d77ea2969989413c319a9b3a747a4476214bc63a8a1725ec82bd28c0f3ca590c | 0ecff68b4ffbd9fa417ba42b220387f06d93399a1e61c4d05eaeeacbdad5d93b | O=S(=O)(CC1CN(Cc2csc3sccc23)C1)c1ccccc1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]2:[#16;a:4]:[c;H0;D3;+0:5](-Br):[c:6]:[c:7]:2:[c:8]:1-[C:9]>>[C:9]-[c:8]1:[cH;D2;+0:1]:[#16;a:2]:[c:3]2:[#16;a:4]:[cH;D2;+0:5]:[c:6]:[c:7]:2:1 | 9.4 | [{"value": 9.4, "product": "FC1=CC=C(C=C1)S(=O)(=O)CC1CN(C1)CC1=CSC=2SC=CC21", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1-[(2,5-dibromothieno[2.3-b]thien-3-yl)methyl]-3-{[(4-fluorophenyl)sulfonyl]methyl}azetidine (Step 4, 39 mg, 0.07 mmol) and 10% palladium on carbon (50 mg) in methanol (7 mL) was stirred under a balloon of hydrogen for 3.5 hours. The catalyst was removed by filtration through Celite®, washing with methanol... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide | null | c1cc2ccsc2s1 | c1cc2ccsc2s1 | C1C[NH]C1.c1cc2ccsc2s1.c1ccccc1 | Br- | [Pd].CO | null | null | O=S(=O)(CC1CN(Cc2c(Br)sc3sc(Br)cc23)C1)c1ccc(F)cc1>[Pd].CO>O=S(=O)(CC1CN(Cc2csc3sccc23)C1)c1ccc(F)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-25fc685f89c34fc6805c7197facceebe | Cc1csc2ccccc12.F[N+]12CC[N+](CCl)(CC1)CC2>>Cc1c(F)sc2ccccc12 | CC1=CSC2=C1C=CC=C2.[B-](F)(F)(F)F.[B-](F)(F)(F)F.C1C[N+]2(CC[N+]1(CC2)CCl)F>>FC=1SC2=C(C1C)C=CC=C2 | [CH3:1][c:2]1[cH:3][s:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]12.ClC[N+]12CC[N+]([F:4])(CC1)CC2>>[CH3:1][c:2]1[c:3]([F:4])[s:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]12 | Cc1csc2ccccc12.F[N+]12CC[N+](CCl)(CC1)CC2 | Cc1c(F)sc2ccccc12 | null | null | C(C)#N | Functional Group Interconversion | OtherReaction | dd1af0df6c21af74052772c69aed95014845c844531e0abdcb39b835744048d9 | aa9e5dc380c4b8055cc423f118798b8f4c6ee7afba420eaba436bc6a11ea5f8a | c1ccc2sccc2c1 | Cl-C-[N+]12-C-C-[N+](-[F;H0;D1;+0:1])(-C-C-1)-C-C-2.[C;D1;H3:2]-[c:3]1:[c:4]:[c:5]:[#16;a:6]:[cH;D2;+0:7]:1>>[C;D1;H3:2]-[c:3]1:[c:4]:[c:5]:[#16;a:6]:[c;H0;D3;+0:7]:1-[F;H0;D1;+0:1] | 72 | [{"value": 72.0, "product": "FC=1SC2=C(C1C)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | null | null | A stirred solution of 3-methylbenzothiophene (0.51 g, 3.37 mmol) in acetonitrile (5 μL) under nitrogen was treated with SELECTFLUOR™ (1.25 g, 3.35 mmol) and heated to 70° C. overnight. The solvent was removed in vacuo. The residue was taken up in ethyl acetate and washed with sodium hydrogen carbonate solution, water a... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Aromatic halide | c1ccc2sccc2c1.C1C[NH+]2CC[NH+]1CC2 | c1ccc2sccc2c1 | c1ccc2sccc2c1 | HCl | C(C)#N | 70 | null | Cc1csc2ccccc12.F[N+]12CC[N+](CCl)(CC1)CC2>C(C)#N>Cc1c(F)sc2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3f09ee017f7c44eca85a9b0a299855f4 | COc1cc(F)ccc1C(=O)CN1CC(CS(=O)(=O)c2ccc(F)cc2)C1>>O=C(CN1CC(CS(=O)(=O)c2ccc(F)cc2)C1)c1ccc(F)cc1O | C(C)OCC.FC1=CC(=C(C=C1)C(CN1CC(C1)CS(=O)(=O)C1=CC=C(C=C1)F)=O)OC.B(Br)(Br)Br>>FC1=CC(=C(C=C1)C(CN1CC(C1)CS(=O)(=O)C1=CC=C(C=C1)F)=O)O | C[O:26][c:25]1[c:19]([C:2](=[O:1])[CH2:3][N:4]2[CH2:5][CH:6]([CH2:7][S:8](=[O:9])(=[O:10])[c:11]3[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]3)[CH2:18]2)[cH:20][cH:21][c:22]([F:23])[cH:24]1>>[O:1]=[C:2]([CH2:3][N:4]1[CH2:5][CH:6]([CH2:7][S:8](=[O:9])(=[O:10])[c:11]2[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]2)[CH2:18]1)[c... | COc1cc(F)ccc1C(=O)CN1CC(CS(=O)(=O)c2ccc(F)cc2)C1 | O=C(CN1CC(CS(=O)(=O)c2ccc(F)cc2)C1)c1ccc(F)cc1O | null | null | ClCCl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C(CN1CC(CS(=O)(=O)c2ccccc2)C1)c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5]=[O;D1;H0:6]>>[O;D1;H0:6]=[C:5]-[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | null | [] | 0 | CELSIUS | 30 | MINUTE | To a solution of 1-(4-fluoro-2-methoxyphenyl)-2-(3-{[(4-fluorophenyl)sulfonyl]methyl}azetidin-1-yl)ethanone (Step 2, 49.4 mg, 0.125 mmol) in dichloromethane (1 mL) at 0° C. was added boron tribromide (1M in dichloromethane, 0.5 mL, 0.5 mmol). The reaction was stirred at 0° C. for 30 minutes. Diethyl ether (5 mL) was ad... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | C1C[NH]C1.c1ccccc1.c1ccccc1 | Other | ClCCl | 0 | 0.5 | COc1cc(F)ccc1C(=O)CN1CC(CS(=O)(=O)c2ccc(F)cc2)C1>ClCCl>O=C(CN1CC(CS(=O)(=O)c2ccc(F)cc2)C1)c1ccc(F)cc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-65a05bfa22984a2caa4c5a8462a966c6 | O=C(CBr)c1ccsc1.O=S(=O)(CC1CNC1)c1ccc(F)cc1>>O=C(CN1CC(CS(=O)(=O)c2ccc(F)cc2)C1)c1ccsc1 | Cl.FC1=CC=C(C=C1)S(=O)(=O)CC1CNC1.BrCC(=O)C1=CSC=C1>>FC1=CC=C(C=C1)S(=O)(=O)CC1CN(C1)CC(=O)C1=CSC=C1 | Br[CH2:3][C:2](=[O:1])[c:19]1[cH:20][cH:21][s:22][cH:23]1.[NH:4]1[CH2:5][CH:6]([CH2:7][S:8](=[O:9])(=[O:10])[c:11]2[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]2)[CH2:18]1>>[O:1]=[C:2]([CH2:3][N:4]1[CH2:5][CH:6]([CH2:7][S:8](=[O:9])(=[O:10])[c:11]2[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]2)[CH2:18]1)[c:19]1[cH:20][cH:21]... | O=C(CBr)c1ccsc1.O=S(=O)(CC1CNC1)c1ccc(F)cc1 | O=C(CN1CC(CS(=O)(=O)c2ccc(F)cc2)C1)c1ccsc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 3e5213a37a85731b6f91e85b682723a05ed75993cbfc6d9bae582d021274456d | 98b92c1800516dd6f2e7ad31e751bba9f02d8a8062f38a8945939bbe90ecca84 | O=C(CN1CC(CS(=O)(=O)c2ccccc2)C1)c1ccsc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#16;a:6].[C:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[#16;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[N;H0;D3;+0:10]1-[C:7]-[C:8]-[C:9]-1 | null | [] | null | null | null | null | Prepared according to the method of Example 2 using 3-{[(4-fluorophenyl)sulfonyl]methyl}azetidine hydrochloride (Example 1 Step 4) and 2-bromo-1-(3-thienyl)ethanone. 1H NMR (500 MHz, d6-DMSO) δ 10.51 (1H, s), 8.52 (1H, s), 7.96 (2H, dd, J=5.1, 8.7 Hz), 7.72 (1H, dd, J=2.8, 5.0 Hz), 7.55 (2H, t, J=8.8 Hz), 7.49 (1H, d, ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Secondary amine | Ketone.Tertiary amine | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccccc1.c1ccsc1 | HBr | null | null | null | O=C(CBr)c1ccsc1.O=S(=O)(CC1CNC1)c1ccc(F)cc1>>O=C(CN1CC(CS(=O)(=O)c2ccc(F)cc2)C1)c1ccsc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-eab3cf5bbfa84edebeddc16063e41490 | CC(C)(C)OC(=O)N1CC(CS(=O)(=O)c2nccs2)C1.O=Cc1nsc2ccccc12>>O=S(=O)(CC1CN(Cc2nsc3ccccc23)C1)c1nccs1 | C(=O)(C(F)(F)F)O.S1C(=NC=C1)S(=O)(=O)CC1CN(C1)C(=O)OC(C)(C)C.[BH3-]C#N.[Na+].S1N=C(C2=C1C=CC=C2)C=O>>S1C(=NC=C1)S(=O)(=O)CC1CN(C1)CC1=NSC2=C1C=CC=C2 | CC(C)(C)OC(=O)[N:7]1[CH2:6][CH:5]([CH2:4][S:2](=[O:1])(=[O:3])[c:19]2[n:20][cH:21][cH:22][s:23]2)[CH2:18]1.O=[CH:8][c:9]1[n:10][s:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]12>>[O:1]=[S:2](=[O:3])([CH2:4][CH:5]1[CH2:6][N:7]([CH2:8][c:9]2[n:10][s:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]23)[CH2:18]1)[c:19]1[n:20][cH... | CC(C)(C)OC(=O)N1CC(CS(=O)(=O)c2nccs2)C1.O=Cc1nsc2ccccc12 | O=S(=O)(CC1CN(Cc2nsc3ccccc23)C1)c1nccs1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | e565984c036082ce756cdc5aa0f2e3959a37ed1edb6965e3c2dff4ca10acf9ec | cf54569061a197ba9f3cab07727ad571966e8f550ff4245a3fd82ef36fe97477 | O=S(=O)(CC1CN(Cc2nsc3ccccc23)C1)c1nccs1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-1.O=[CH;D2;+0:5]-[c:6]1:[#7;a:7]:[#16;a:8]:[c:9]:[c:10]:1>>[#16;a:8]1:[#7;a:7]:[c:6](-[CH2;D2;+0:5]-[N;H0;D3;+0:1]2-[C:2]-[C:3]-[C:4]-2):[c:10]:[c:9]:1 | 32.5 | [{"value": 29.0, "product": "S1C(=NC=C1)S(=O)(=O)CC1CN(C1)CC1=NSC2=C1C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 32.5, "product": "S1C(=NC=C1)S(=O)(=O)CC1CN(C1)CC1=NSC2=C1C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | tert-Butyl 3-[(1,3-thiazol-2-ylsulfonyl)methyl]azetidine-1-carboxylate (51 mg, 0.16 mmol) was dissolved in DCM (0.5 mL) and TFA (0.5 mL) was added. The resulting mixture was stirred for 30 min. then concentrated in vacuo. The residual oil was taken up in MeOH (2 mL), then NaCNBH3 (16.2 mg, 0.26 mmol) and 1,2-benzisothi... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Carbamic ester.Ether.Boc | Tertiary amine | C1C[NH]C1 | C1C[NH]C1 | C1C[NH]C1.c1ccc2sncc2c1.c1cscn1 | HO- | C(Cl)Cl | null | 0.5 | CC(C)(C)OC(=O)N1CC(CS(=O)(=O)c2nccs2)C1.O=Cc1nsc2ccccc12>C(Cl)Cl>O=S(=O)(CC1CN(Cc2nsc3ccccc23)C1)c1nccs1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-39c41fe7972a4ae19815cb27c1946a12 | CCOC(C)=O.Cc1ccc(CC#N)c(C)c1>>CC(=O)C(C#N)c1ccc(C)cc1C | [Na].CC1=C(C=CC(=C1)C)CC#N.C(C)(=O)OCC>>C(#N)C(C(C)=O)C1=C(C=C(C=C1)C)C | CCO[C:2]([CH3:1])=[O:3].[CH2:4]([C:5]#[N:6])[c:7]1[cH:8][cH:9][c:10]([CH3:11])[cH:12][c:13]1[CH3:14]>>[CH3:1][C:2](=[O:3])[CH:4]([C:5]#[N:6])[c:7]1[cH:8][cH:9][c:10]([CH3:11])[cH:12][c:13]1[CH3:14] | CCOC(C)=O.Cc1ccc(CC#N)c(C)c1 | CC(=O)C(C#N)c1ccc(C)cc1C | null | null | null | C-C Coupling | OtherReaction | 8ce89878f5db9b98fa4633d16adf2407dbf79d96925d930c608f1ce0756e674e | f80cbbd7f2bfc042e62829b7de30498cf0880b808f2adad888ffdfe089982722 | c1ccccc1 | C-C-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[N;D1;H0:4]#[C:5]-[CH2;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[CH;D3;+0:6](-[C:5]#[N;D1;H0:4])-[c:7](:[c:8]):[c:9] | 74 | [{"value": 74.0, "product": "C(#N)C(C(C)=O)C1=C(C=C(C=C1)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | Sodium pellets (9.8 g, 0.43 mol) were added portionwise to a solution of 2,4-dimethylphenylacetonitrile (48 g, 0.33 mol) in ethyl acetate (150 mL) at ambient temperature. The reaction mixture was heated to reflux temperature and stirred for 16 hours. The resulting suspension was cooled to room temperature and filtered.... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ketone | null | null | c1ccccc1 | HO- | null | null | 16 | CCOC(C)=O.Cc1ccc(CC#N)c(C)c1>>CC(=O)C(C#N)c1ccc(C)cc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d1bb8a0a8ba549718554f7c939ed38d2 | CC(=O)C(C#N)c1ccc(C)cc1C.NN>>Cc1ccc(-c2c(C)n[nH]c2N)c(C)c1 | C(#N)C(C(C)=O)C1=C(C=C(C=C1)C)C.O.NN.C(C)(=O)O>>NC1=C(C(=NN1)C)C1=C(C=C(C=C1)C)C | O=[C:7]([CH:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:15][c:13]1[CH3:14])[C:11]#[N:12])[CH3:8].[NH2:9][NH2:10]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c:7]([CH3:8])[n:9][nH:10][c:11]2[NH2:12])[c:13]([CH3:14])[cH:15]1 | CC(=O)C(C#N)c1ccc(C)cc1C.NN | Cc1ccc(-c2c(C)n[nH]c2N)c(C)c1 | null | null | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | 5313ea2b547a7e97f846d9307e42ac2925475188c06332e189417467db3f09a0 | a78e9303472e036bbc8878e5b3222e30e9aba072d6de158deb64f510e46fb597 | c1ccc(-c2cn[nH]c2)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH;D3;+0:3](-[C;H0;D2;+0:4]#[N;H0;D1;+0:5])-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[C;D1;H3:10]):[c:11].[NH2;D1;+0:12]-[NH2;D1;+0:13]>>[C;D1;H3:10]-[c:9](:[c:11]):[c;H0;D3;+0:6](-[c;H0;D3;+0:3]1:[c;H0;D3;+0:4](-[NH2;D1;+0:5]):[nH;D2;+0:12]:[n;H0;D2;+0:13]:[c;H0;D3;+0:1]:1-[C;D1;H3:2]):[c:7]... | 75 | [{"value": 75.0, "product": "NC1=C(C(=NN1)C)C1=C(C=C(C=C1)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.7, "product": "NC1=C(C(=NN1)C)C1=C(C=C(C=C1)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1-cyano-1-(2,4-dimethylphenyl)propan-2-one (43.8 g, 0.23 mol), hydrazine-hydrate (22 mL, 0.46 mol), glacial acetic acid (45 mL, 0.78 mol) and toluene (500 mL) were stirred at reflux temperature for 18 hours in an apparatus fitted with a Dean-Stark trap. The reaction mixture was cooled to ambient temperatur... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Nitrile | Primary amine | null | c1cn[nH]c1 | c1ccccc1.c1cn[nH]c1 | HO- | C1(=CC=CC=C1)C | null | null | CC(=O)C(C#N)c1ccc(C)cc1C.NN>C1(=CC=CC=C1)C>Cc1ccc(-c2c(C)n[nH]c2N)c(C)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d57d259249774992a4044291bddceda3 | Cc1cc(C)c(CC#N)c(C)c1.[N-]=[N+]=NCc1ccccc1>>Cc1cc(C)c(-c2nnn(Cc3ccccc3)c2N)c(C)c1 | CC1=C(CC#N)C(=CC(=C1)C)C.C(C1=CC=CC=C1)N=[N+]=[N-].CC(C)([O-])C.[K+]>>C1(=CC=CC=C1)CN1N=NC(=C1N)C1=C(C=C(C=C1C)C)C | [CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([CH2:7][C:18]#[N:19])[c:20]([CH3:21])[cH:22]1.[N-:8]=[N+:9]=[N:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6](-[c:7]2[n:8][n:9][n:10]([CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[c:18]2[NH2:19])[c:20]([CH3:21])[cH:22]1 | Cc1cc(C)c(CC#N)c(C)c1.[N-]=[N+]=NCc1ccccc1 | Cc1cc(C)c(-c2nnn(Cc3ccccc3)c2N)c(C)c1 | null | null | O.O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | c1d3018eac14815fee8f7857ea430215a7f4f850e9d43e9307e624d72deeb6c1 | b84e732d8bb9a3420cab721ea7dd7b4e6402eee3aa5cf04ea7e40492aaa668d7 | c1ccc(Cn2cc(-c3ccccc3)nn2)cc1 | [C;D1;H3:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[CH2;D2;+0:5]-[C;H0;D2;+0:6]#[N;H0;D1;+0:7]):[c:8](-[C;D1;H3:9]):[c:10].[N-;H0;D1:11]=[N+;H0;D2:12]=[N;H0;D2;+0:13]-[C:14]-[c:15]>>[C;D1;H3:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[c;H0;D3;+0:5]1:[n;H0;D2;+0:11]:[n;H0;D2;+0:12]:[n;H0;D3;+0:13](-[C:14]-[c:15]):[c;H0;D3;+0:6]:1-[NH2;D1;... | 61 | [{"value": 61.0, "product": "C1(=CC=CC=C1)CN1N=NC(=C1N)C1=C(C=C(C=C1C)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.8, "product": "C1(=CC=CC=C1)CN1N=NC(=C1N)C1=C(C=C(C=C1C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2.5 | DAY | A mixture of 2,4,6-trimethylbenzyl cyanide (1.0 g, 6.3 mmol), benzyl azide (0.92 g, 6.9 mmol) and potassium t-butoxide (0.78 g, 6.9 mmol) in tetrahydrofuran (10 mL) was stirred at ambient temperature for 2.5 days. The resulting suspension was diluted with water and extracted three times with ethyl acetate. The combined... | 10.6084/m9.figshare.5104873.v1 | null | Azide.Nitrile | Primary amine | null | c1c[nH]nn1 | c1ccccc1.c1c[nH]nn1.c1ccccc1 | null | O.O1CCCC1 | null | 60 | Cc1cc(C)c(CC#N)c(C)c1.[N-]=[N+]=NCc1ccccc1>O.O1CCCC1>Cc1cc(C)c(-c2nnn(Cc3ccccc3)c2N)c(C)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f75ca00c8a2d4cd79176f32f013e8113 | Cc1ccc(-c2cnn3c(O)cc(C)nc23)c(Cl)c1.O=P(Cl)(Cl)Cl>>Cc1ccc(-c2cnn3c(Cl)cc(C)nc23)c(Cl)c1 | OC1=CC(=NC=2N1N=CC2C2=C(C=C(C=C2)C)Cl)C.P(=O)(Cl)(Cl)Cl.C(C)N(C1=CC=CC=C1)CC.C1(=CC=CC=C1)C>>ClC1=CC(=NC=2N1N=CC2C2=C(C=C(C=C2)C)Cl)C | O[c:10]1[n:9]2[n:8][cH:7][c:6](-[c:5]3[cH:4][cH:3][c:2]([CH3:1])[cH:19][c:17]3[Cl:18])[c:16]2[n:15][c:13]([CH3:14])[cH:12]1.O=P(Cl)(Cl)[Cl:11]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][n:8][n:9]3[c:10]([Cl:11])[cH:12][c:13]([CH3:14])[n:15][c:16]23)[c:17]([Cl:18])[cH:19]1 | Cc1ccc(-c2cnn3c(O)cc(C)nc23)c(Cl)c1.O=P(Cl)(Cl)Cl | Cc1ccc(-c2cnn3c(Cl)cc(C)nc23)c(Cl)c1 | null | null | CCOC(=O)C.CCCCCC | Functional Group Interconversion | Alcohol to chloride_POCl3_ortho | 30db31a49fb136d312e5cd66a18ec0f0a14dbcb214980b33f05231569e6e02fd | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1ccc(-c2cnn3cccnc23)cc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[c;H0;D3;+0:2]1:[c:3]:[c:4](-[C;D1;H3:5]):[#7;a:6]:[c:7]:[#7;a:8]:1:[#7;a:9]:[c:10]>>[C;D1;H3:5]-[c:4]1:[#7;a:6]:[c:7]:[#7;a:8](:[#7;a:9]:[c:10]):[c;H0;D3;+0:2](-[Cl;H0;D1;+0:1]):[c:3]:1 | 88 | [{"value": 84.0, "product": "ClC1=CC(=NC=2N1N=CC2C2=C(C=C(C=C2)C)Cl)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.0, "product": "ClC1=CC(=NC=2N1N=CC2C2=C(C=C(C=C2)C)Cl)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 7-hydroxy-5-methyl-3-(2-chloro-4-methylphenyl)-pyrazolo[1,5-a]pyrimidine (1.0 g, 3.5 mmol), phosphorus oxychloride (2.7 g, 1.64 mL, 17.4 mmol), N,N-diethylaniline (0.63 g, 0.7 mL, 4.2 mmol) and toluene (20 mL) was stirred at reflux temperature for 3 hours, then it was cooled to ambient temperature. The vol... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1cnc2ccnn2c1 | c1cnc2ccnn2c1 | c1ccccc1.c1cnc2ccnn2c1 | HCl | CCOC(=O)C.CCCCCC | null | null | Cc1ccc(-c2cnn3c(O)cc(C)nc23)c(Cl)c1.O=P(Cl)(Cl)Cl>CCOC(=O)C.CCCCCC>Cc1ccc(-c2cnn3c(Cl)cc(C)nc23)c(Cl)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-eabe532b36c040a6b450ec034d5b8835 | N#Cc1ccncc1.[Cl-].[NH4+]>>Cl.N=C(N)c1ccncc1 | C(C)OCC.[Cl-].[NH4+].[Na].C(#N)C1=CC=NC=C1>>Cl.C(N)(=N)C1=CC=NC=C1 | [N:2]#[C:3][c:5]1[cH:6][cH:7][n:8][cH:9][cH:10]1.[Cl-:1].[NH4+:4]>>[ClH:1].[NH:2]=[C:3]([NH2:4])[c:5]1[cH:6][cH:7][n:8][cH:9][cH:10]1 | N#Cc1ccncc1.[Cl-].[NH4+] | Cl.N=C(N)c1ccncc1 | null | null | CO | Functional Group Interconversion | OtherReaction | 3b047a13c16a607c445b1c419e256808e8c9a0097d8fb9efd4e7970deb782b70 | 2882e57127fc469aa16ca9a2fd53388b6d97c74c76c010e6eb01be5726f46aa5 | c1ccncc1 | [Cl-;H0;D0:1].[N;H0;D1;+0:2]#[C;H0;D2;+0:3]-[c:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1.[NH4+;D0:10]>>[ClH;D0;+0:1].[NH2;D1;+0:10]-[C;H0;D3;+0:3](=[NH;D1;+0:2])-[c:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1 | 93 | [{"value": 93.0, "product": "Cl.C(N)(=N)C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | To a solution of sodium (0.23 g) in methanol (40 ml) was added 4-cyanopyridine (10.62 g) at r.t. Stirring was continued for 6 h followed by the addition of ammoniumchloride (5.9 g) and stirring was continued for another 10 h. Then, diethylether (120 ml) was added and the precipitate was filtered off after 30 min and wa... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccncc1 | null | CO | null | 6 | N#Cc1ccncc1.[Cl-].[NH4+]>CO>Cl.N=C(N)c1ccncc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-94a6e748775046e49a294af652c20247 | COC(=O)C(Cl)C(=O)OC.COc1ccccc1O>>COC(=O)C(Oc1ccccc1OC)C(=O)OC | COC(C(C(=O)OC)Cl)=O.COC1=C(C=CC=C1)O.C([O-])([O-])=O.[K+].[K+]>>COC(C(C(=O)OC)OC1=C(C=CC=C1)OC)=O | Cl[CH:5]([C:3]([O:2][CH3:1])=[O:4])[C:15](=[O:16])[O:17][CH3:18].[OH:6][c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[O:13][CH3:14]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([O:6][c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[O:13][CH3:14])[C:15](=[O:16])[O:17][CH3:18] | COC(=O)C(Cl)C(=O)OC.COc1ccccc1O | COC(=O)C(Oc1ccccc1OC)C(=O)OC | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 1abe5687f21dfe01b11318540a21f9edb38806e03f96e75bf8c2106db3fe9462 | 51ddfc8e04785767c04eb49244add5bfc6d44a3e44b55034aace28217a5407e3 | c1ccccc1 | Cl-[CH;D3;+0:1](-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5])-[C:6](=[O;D1;H0:7])-[#8:8]-[C;D1;H3:9].[OH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C;D1;H3:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH;D3;+0:1](-[O;H0;D2;+0:10]-[c:11](:[c:12]):[c:13])-[C:6](=[O;D1;H0:7])-[#8:8]-[C;D1;H3:9] | null | [] | 45 | CELSIUS | null | null | 2-Methoxy-phenol (guaiacol) (48 ml) was slowly added to a stirred suspension of potassium carbonate (70.8 g) in acetone (480 ml) followed by heating to 45° C. Then, dimethylchloromalonate (63.2 ml) in acetone (50 ml) was added within 20 min. The reaction mixture was heated to reflux for 16 h. The solvent was evaporated... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ester.Ester.Aromatic alcohol | Ester.Ester.Ether | null | null | c1ccccc1 | HCl | CC(=O)C | 45 | null | COC(=O)C(Cl)C(=O)OC.COc1ccccc1O>CC(=O)C>COC(=O)C(Oc1ccccc1OC)C(=O)OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-44158203bde3470ebd74d37d12d5fe1d | CC(C)c1ccc(NS(N)(=O)=O)cc1.COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1Cl>>COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1NS(=O)(=O)Nc1ccc(C(C)C)cc1 | ClC1=NC(=NC(=C1OC1=C(C=CC=C1)OC)Cl)C1=CC=NC=C1.CCOC(=O)C.C(C)(C)C1=CC=C(C=C1)NS(N)(=O)=O.[H-].[Na+]>>ClC1=C(C(=NC(=N1)C1=CC=NC=C1)NS(NC1=CC=C(C=C1)C(C)C)(=O)=O)OC1=C(C=CC=C1)OC | [NH2:23][S:24](=[O:25])(=[O:26])[NH:27][c:28]1[cH:29][cH:30][c:31]([CH:32]([CH3:33])[CH3:34])[cH:35][cH:36]1.Cl[c:22]1[c:10]([O:9][c:8]2[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]2)[c:11]([Cl:12])[n:13][c:14](-[c:15]2[cH:16][cH:17][n:18][cH:19][cH:20]2)[n:21]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[O:9][c:10... | CC(C)c1ccc(NS(N)(=O)=O)cc1.COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1Cl | COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1NS(=O)(=O)Nc1ccc(C(C)C)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 345edf40ad678aea0250ec5b3d6cc512d8eac020b2f4324f423c18b59726753e | e7974806b40218fa965bb62bf9c430cac38870897b20726116f8b48ae128dc55 | O=S(=O)(Nc1ccccc1)Nc1nc(-c2ccncc2)ncc1Oc1ccccc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](-[Cl;D1;H0:7]):[c:8]:1-[#8:9].[#7:10]-[#16:11](-[NH2;D1;+0:12])(=[O;D1;H0:13])=[O;D1;H0:14]>>[#7:10]-[#16:11](=[O;D1;H0:13])(=[O;D1;H0:14])-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](-[Cl;D1;H0:7]):[c:8]:1-[#8:9] | 26.7 | [{"value": 26.7, "product": "ClC1=C(C(=NC(=N1)C1=CC=NC=C1)NS(NC1=CC=C(C=C1)C(C)C)(=O)=O)OC1=C(C=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 45 | CELSIUS | 60 | HOUR | To a solution of 4-i-propyl-phenyl sulfamic acid amide (642 mg; Referential Example 17) in DMF (9 ml) was added sodium hydride (250 mg). The mixture was warmed to 45° C. for 30 min. Then, 4,6-dichloro-5-(o-methoxyphenoxy)-2-(4-pyridyl)-pyrimidine (1.044 g) was added and the reaction mixture was stirred for 60 h at r.t.... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Aromatic halide | Sulfonamide | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccncc1.c1ccccc1 | HCl | CN(C)C=O | 45 | 60 | CC(C)c1ccc(NS(N)(=O)=O)cc1.COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1Cl>CN(C)C=O>COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1NS(=O)(=O)Nc1ccc(C(C)C)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ba7cc86b1c11497fa2e3875ac0edb856 | CC(=N)N.COC(=O)C(Oc1ccccc1OC)C(=O)OC>>COc1ccccc1Oc1c(O)nc(C)nc1O | COC(C(C(=O)OC)OC1=C(C=CC=C1)OC)=O.C[O-].[Na+].Cl.C(C)(=N)N>>COC1=C(OC=2C(=NC(=NC2O)C)O)C=CC=C1 | [NH:13]=[C:14]([CH3:15])[NH2:16].CO[C:11]([CH:10]([O:9][c:8]1[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]1)[C:17](OC)=[O:18])=[O:12]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[O:9][c:10]1[c:11]([OH:12])[n:13][c:14]([CH3:15])[n:16][c:17]1[OH:18] | CC(=N)N.COC(=O)C(Oc1ccccc1OC)C(=O)OC | COc1ccccc1Oc1c(O)nc(C)nc1O | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | 796aa162e0a30c54f338ba814a50cc53fed7c215d3c57f65326fb9776d23e139 | a50cc796d897bf9b166ec1e8e95b10119ae9505acba8e8cb752173a4740126a8 | c1ccc(Oc2cncnc2)cc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[CH;D3;+0:3](-[#8:4]-[c:5])-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-O-C.[C;D1;H3:8]-[C;H0;D3;+0:9](-[NH2;D1;+0:10])=[NH;D1;+0:11]>>[C;D1;H3:8]-[c;H0;D3;+0:9]1:[n;H0;D2;+0:11]:[c;H0;D3;+0:1](-[OH;D1;+0:2]):[c;H0;D3;+0:3](-[#8:4]-[c:5]):[c;H0;D3;+0:6](-[OH;D1;+0:7]):[n;H0;D2;+0:10]:1 | 69.3 | [{"value": 69.3, "product": "COC1=C(OC=2C(=NC(=NC2O)C)O)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of dimethyl-(o-methoxyphenoxy)malonate (10 g) in dry methanol (80 ml) was cooled to 0° C. Sodium methylate (6.71 g) was added portionwise. To the suspension was added of acetamidine hydrochloride (2.84 g) and the mixture was stirred overnight at r.t. The solvent was removed under reduced pressure and the res... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ether.Primary amine | Ether.Aromatic alcohol.Aromatic alcohol | null | c1cncnc1 | c1ccccc1.c1cncnc1 | HO- | CO | null | 8 | CC(=N)N.COC(=O)C(Oc1ccccc1OC)C(=O)OC>CO>COc1ccccc1Oc1c(O)nc(C)nc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-81e84f2f46764e7283256657b7d79e0f | COC(=O)C(Oc1ccccc1OC)C(=O)OC.N=CN>>COc1ccccc1Oc1c(O)ncnc1O | C[O-].[Na+].COC(C(C(=O)OC)OC1=C(C=CC=C1)OC)=O.Cl.C(=N)N>>COC1=C(OC=2C(=NC=NC2O)O)C=CC=C1 | CO[C:11]([CH:10]([O:9][c:8]1[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]1)[C:16](OC)=[O:17])=[O:12].[NH:13]=[CH:14][NH2:15]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[O:9][c:10]1[c:11]([OH:12])[n:13][cH:14][n:15][c:16]1[OH:17] | COC(=O)C(Oc1ccccc1OC)C(=O)OC.N=CN | COc1ccccc1Oc1c(O)ncnc1O | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | 796aa162e0a30c54f338ba814a50cc53fed7c215d3c57f65326fb9776d23e139 | a50cc796d897bf9b166ec1e8e95b10119ae9505acba8e8cb752173a4740126a8 | c1ccc(Oc2cncnc2)cc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[CH;D3;+0:3](-[#8:4]-[c:5])-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-O-C.[NH2;D1;+0:8]-[CH;D2;+0:9]=[NH;D1;+0:10]>>[OH;D1;+0:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:10]:[cH;D2;+0:9]:[n;H0;D2;+0:8]:[c;H0;D3;+0:6](-[OH;D1;+0:7]):[c;H0;D3;+0:3]:1-[#8:4]-[c:5] | 86.7 | [{"value": 86.7, "product": "COC1=C(OC=2C(=NC=NC2O)O)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | At 5° C. sodium methylate (12.7 g) was added portionwise to a solution of dimethyl-(o-methoxyphenoxy)malonate (18.9 g) in methanol (450 ml). Upon completion of the addition stirring was continued at r.t. for 30 min followed by the addition of formamidine hydrochloride (6 g). The mixture was stirred at r.t. for 72 h. Ev... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ether.Primary amine | Ether.Aromatic alcohol.Aromatic alcohol | null | c1cncnc1 | c1ccccc1.c1cncnc1 | HO- | CO | null | 0.5 | COC(=O)C(Oc1ccccc1OC)C(=O)OC.N=CN>CO>COc1ccccc1Oc1c(O)ncnc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5f2fb7b342c44f879faf621a08f0c6ed | CCOC(=O)C(C(=O)OCC)c1ccc(C)cc1.N=CN>>Cc1ccc(-c2c(O)ncnc2O)cc1 | C1(=CC=C(C=C1)C(C(=O)OCC)C(=O)OCC)C.C[O-].[Na+].Cl.C(=N)N>>OC1=NC=NC(=C1C1=CC=C(C=C1)C)O | CCO[C:7]([CH:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:15][cH:14]1)[C:12](OCC)=[O:13])=[O:8].[NH:9]=[CH:10][NH2:11]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c:7]([OH:8])[n:9][cH:10][n:11][c:12]2[OH:13])[cH:14][cH:15]1 | CCOC(=O)C(C(=O)OCC)c1ccc(C)cc1.N=CN | Cc1ccc(-c2c(O)ncnc2O)cc1 | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | d507ea5e988c6bcfe927f1b3a86f934f8a1c706f38171153cdf4dbd7aeb28e83 | 6504f33921726f64e36c5f3f322459b73652319c83071522ec21b8b88a33a5a7 | c1ccc(-c2cncnc2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[CH;D3;+0:3](-[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-O-C-C)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10].[NH2;D1;+0:11]-[CH;D2;+0:12]=[NH;D1;+0:13]>>[OH;D1;+0:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:11]:[cH;D2;+0:12]:[n;H0;D2;+0:13]:[c;H0;D3;+0:4](-[OH;D1;+0:5]):[c;H0;D3;+0:3]:1-[c;H0;D3;+0:6](:[c:7]... | 97.6 | [{"value": 97.6, "product": "OC1=NC=NC(=C1C1=CC=C(C=C1)C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | At 0° C. a solution of diethyl 2-(p-tolyl)-malonate (14.2 g) in methanol (50 ml) was slowly added to a solution of sodium methylate (9.4 g) in methanol (300 ml). Upon completion of the addition the reaction mixture was allowed to warm up and formamidine hydrochloride (5.4 g) was added. The mixture was stirred at r.t. f... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Primary amine | Aromatic alcohol.Aromatic alcohol | null | c1cncnc1 | c1ccccc1.c1cncnc1 | HO- | CO | null | 16 | CCOC(=O)C(C(=O)OCC)c1ccc(C)cc1.N=CN>CO>Cc1ccc(-c2c(O)ncnc2O)cc1 |
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