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-c3fa110c818b49349c5d166723b662c8 | CC([O-])=S.COC(=O)[C@@H]1C[C@@H](OS(C)(=O)=O)CN1C>>COC(=O)[C@@H]1C[C@H](SC(C)=O)CN1C | C(C)(=S)[O-].[K+].CS(=O)(=O)O[C@@H]1C[C@H](N(C1)C)C(=O)OC.C(C)(=O)OCC.[Cl-].[Na+]>>C(C)(=O)S[C@H]1C[C@H](N(C1)C)C(=O)OC | [S:8]=[C:9]([CH3:10])[O-:11].CS(=O)(=O)O[C@@H:7]1[CH2:6][C@@H:5]([C:3]([O:2][CH3:1])=[O:4])[N:13]([CH3:14])[CH2:12]1>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@H:7]([S:8][C:9]([CH3:10])=[O:11])[CH2:12][N:13]1[CH3:14] | CC([O-])=S.COC(=O)[C@@H]1C[C@@H](OS(C)(=O)=O)CN1C | COC(=O)[C@@H]1C[C@H](SC(C)=O)CN1C | null | null | C(C)O.O | Acylation | OtherReaction | e9c965ce4107a29dbd05f1b7a7697fce5ec80148cd1f96b0b2193311943fffc0 | baefe85e02f69a50397a95d1513108a9b7e2f7c9b47a29793adc8496482d4046 | C1CCNC1 | C-S(=O)(=O)-O-[C@H;D3;+0:1]1-[C:2]-[#7:3](-[C;D1;H3:4])-[C:5](-[C:6](-[#8:7])=[O;D1;H0:8])-[C:9]-1.[C;D1;H3:10]-[C;H0;D3;+0:11](-[O-;H0;D1:12])=[S;H0;D1;+0:13]>>[#8:7]-[C:6](=[O;D1;H0:8])-[C:5]1-[C:9]-[C@H;D3;+0:1](-[S;H0;D2;+0:13]-[C;H0;D3;+0:11](-[C;D1;H3:10])=[O;H0;D1;+0:12])-[C:2]-[#7:3]-1-[C;D1;H3:4] | 97.4 | [{"value": 97.0, "product": "C(C)(=O)S[C@H]1C[C@H](N(C1)C)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.4, "product": "C(C)(=O)S[C@H]1C[C@H](N(C1)C)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 3 | HOUR | Potassium thioacetate (677 mg) was added to a solution of methyl (2S,4R)-4-methylsulfonyloxy-1-methyl-2-pyrrolidinecarboxylate (609 mg) obtained from Reference example 4 in ethanol/water (9:1) (6 ml), and the resulting mixture was stirred at 80° C. for 3 hours, and then the mixture was allowed to stand overnight at the... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Thiocarbonyl | Carbo-thioester | C1CC[NH]C1 | C1CC[NH]C1 | C1CC[NH]C1 | MsOH.HO- | C(C)O.O | 80 | 3 | CC([O-])=S.COC(=O)[C@@H]1C[C@@H](OS(C)(=O)=O)CN1C>C(C)O.O>COC(=O)[C@@H]1C[C@H](SC(C)=O)CN1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c90dc2dd01f949469059e8711881967f | COC(=O)[C@@H]1C[C@H](SC(C)=O)CN1C>>CN1C[C@@H](S)C[C@H]1C(=O)O | C(C)(=O)S[C@H]1C[C@H](N(C1)C)C(=O)OC.Cl>>Cl.S[C@H]1C[C@H](N(C1)C)C(=O)O | CC(=O)[S:5][C@@H:4]1[CH2:3][N:2]([CH3:1])[C@H:7]([C:8](=[O:9])[O:10]C)[CH2:6]1>>[CH3:1][N:2]1[CH2:3][C@@H:4]([SH:5])[CH2:6][C@H:7]1[C:8](=[O:9])[OH:10] | COC(=O)[C@@H]1C[C@H](SC(C)=O)CN1C | CN1C[C@@H](S)C[C@H]1C(=O)O | null | null | O | Reduction | OtherReaction | 1bcd8cbb2f136b4bcba1690e9ba45c4e43c89ba76f0e22de82a7d3fe318c82a9 | 5654c46fe4cb226f88ec3c899c7f9be1825c357673ea686958f9ef4883ee1db3 | C1CCNC1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]1-[#7:5]-[C:6]-[C:7](-[S;H0;D2;+0:8]-C(-C)=O)-[C:9]-1>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[C:4]1-[#7:5]-[C:6]-[C:7](-[SH;D1;+0:8])-[C:9]-1 | 95 | [{"value": 95.0, "product": "Cl.S[C@H]1C[C@H](N(C1)C)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.5, "product": "Cl.S[C@H]1C[C@H](N(C1)C)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 2.5 | CELSIUS | 1 | HOUR | A mixed solution of methyl (2S,4S)-4-acetylthio-1-methyl-2-pyrrolidinecarboxylate (10.7 g), concentrated hydrochloric acid (14.9 g) and water (16 mL) was stirred at from 75 to 85° C. for 5 hours. After completion of the reaction, the water in the reaction mixture was removed by distillation under reduced pressure. Acet... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Carbo-thioester | Carboxylic acid.Aliphatic thiol | null | null | C1CC[NH]C1 | HO- | O | 2.5 | 1 | COC(=O)[C@@H]1C[C@H](SC(C)=O)CN1C>O>CN1C[C@@H](S)C[C@H]1C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e90368ffd2234df394e85e5cab1a5b4f | CC(C)(C)OC(=O)N1CC[C@H](NC(=O)CNC(=N)NC(=O)OCc2ccc([N+](=O)[O-])cc2)C1.O=S(=O)(O)O>>N=C(NCC(=O)N[C@H]1CCNC1)NC(=O)OCc1ccc([N+](=O)[O-])cc1.O=S(=O)(O)OS(=O)(=O)O | C(C)(C)(C)OC(=O)N1C[C@H](CC1)NC(CNC(=N)NC(=O)OCC1=CC=C(C=C1)[N+](=O)[O-])=O.S(O)(O)(=O)=O.C(C)(C)OC(C)C>>S(=O)(=O)(O)OS(=O)(=O)O.[N+](=O)([O-])C1=CC=C(COC(=O)NC(NCC(=O)N[C@@H]2CNCC2)=N)C=C1 | CC(C)(C)[O:33]C([N:11]1[CH2:10][CH2:9][C@H:8]([NH:7][C:5]([CH2:4][NH:3][C:2](=[NH:1])[NH:13][C:14](=[O:15])[O:16][CH2:17][c:18]2[cH:19][cH:20][c:21]([N+:22](=[O:23])[O-:24])[cH:25][cH:26]2)=[O:6])[CH2:12]1)=[O:29].[O:27]=[S:28]([OH:30])(=[O:31])[OH:35]>>[NH:1]=[C:2]([NH:3][CH2:4][C:5](=[O:6])[NH:7][C@H:8]1[CH2:9][CH2:1... | CC(C)(C)OC(=O)N1CC[C@H](NC(=O)CNC(=N)NC(=O)OCc2ccc([N+](=O)[O-])cc2)C1.O=S(=O)(O)O | N=C(NCC(=O)N[C@H]1CCNC1)NC(=O)OCc1ccc([N+](=O)[O-])cc1.O=S(=O)(O)OS(=O)(=O)O | null | null | CO | Oxidation | OtherReaction | 8630b73717354f3d9bbc23c70dfd528739ddb8e33ba46ba6de2b4f3c5c185628 | d660b0dbcfc83627a68230ba542c5fa5356dbf803f8bbf402ff57932667d1b5d | N=C(NCC(=O)N[C@H]1CCNC1)NC(=O)OCc1ccccc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-C(=[O;H0;D1;+0:2])-[N;H0;D3;+0:3]1-[C:4]-[C:5]-[C:6]-[C:7]-1.[O;D1;H0:8]=[S;H0;D4;+0:9](-[O;D1;H1:10])(=[O;H0;D1;+0:11])-[OH;D1;+0:12]>>[C:4]1-[C:5]-[C:6]-[C:7]-[NH;D2;+0:3]-1.[O;D1;H0:8]=[S;H0;D4;+0:9](-[O;D1;H1:10])(=[O;H0;D1;+0:2])-[O;H0;D2;+0:11]-[#16:13](=[O;D1;H0:14])(=[O;H0;D1;+0:1])-[... | 95.4 | [{"value": 95.4, "product": "S(=O)(=O)(O)OS(=O)(=O)O.[N+](=O)([O-])C1=CC=C(COC(=O)NC(NCC(=O)N[C@@H]2CNCC2)=N)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.2, "product": "S(=O)(=O)(O)OS(=O)(=O)O.[N+](=O)([O-])C1=CC=C(COC(=O)NC(NCC(=O)N[C@@H]2CNCC2)=N)C=C1", "details": "CALCULATEDPERCENTYIELD", "is... | 42.5 | CELSIUS | 2.5 | HOUR | (S)-1-(t-butyloxycarbonyl)-3-[2-[3-(4-nitrobenzyloxycarbonyl)guanidino]acetylamino]pyrrolidine ½ sulfate (350 g, purity 86%) was added to a solution of concentrated sulfuric acid (234 g) and methanol (2.45 L) and the mixture was stirred at from 40 to 45° C. for 2.5 hours. The reaction mixture was cooled to from 20 to 3... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]C1 | C1CCNC1 | C1CCNC1.c1ccccc1 | Other | CO | 42.5 | 2.5 | CC(C)(C)OC(=O)N1CC[C@H](NC(=O)CNC(=N)NC(=O)OCc2ccc([N+](=O)[O-])cc2)C1.O=S(=O)(O)O>CO>N=C(NCC(=O)N[C@H]1CCNC1)NC(=O)OCc1ccc([N+](=O)[O-])cc1.O=S(=O)(O)OS(=O)(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5a2db9b125ed4b8db32b988a6303e957 | C1=CCCCC1>>CC1=CCCC1 | C1=CCCCC1.C1=CCCCC1.C1(CCCCC1)O.C1=CCCCC1>>CC1=CCCC1.C1(CCCCC1)O | [CH:1]1=[CH:2][CH2:6][CH2:5][CH2:4][CH2:3]1>>[CH3:1][C:2]1=[CH:3][CH2:4][CH2:5][CH2:6]1 | C1=CCCCC1 | CC1=CCCC1 | null | null | O | Miscellaneous | OtherReaction | 27740ad5f143ad9e6c640e57416e27a0b32c0f1ec9a6b9ddf7510d1d5c5cf251 | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | C1=CCCC1 | [C:1]1-[C:2]-[C:3]-[CH;D2;+0:4]=[CH;D2;+0:5]-[CH2;D2;+0:6]-1>>[CH3;D1;+0:5]-[C;H0;D3;+0:4]1=[CH;D2;+0:6]-[C:1]-[C:2]-[C:3]-1 | null | [] | null | null | null | null | With respect to the manner of the hydration reaction, there is no particular limitation; the reaction can be performed in either of continuous and batchwise manners. The hydration reaction is generally performed as follows. Cyclohexene is added to a catalyst slurry comprising a hydration catalyst and water to effect hy... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1=CCCCC1 | C1=CCCC1 | C1=CCCC1 | null | O | null | null | C1=CCCCC1>O>CC1=CCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-02e4c90fbc514857ac01b7be488cb366 | COC(=O)c1cccc([N+](=O)[O-])c1C(=O)OC>>COC(=O)c1cccc(N)c1C(=O)OC | COC(C1=C(C(=CC=C1)[N+](=O)[O-])C(=O)OC)=O.[H][H]>>COC(C1=C(C(=CC=C1)N)C(=O)OC)=O | O=[N+:10]([O-])[c:9]1[cH:8][cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:11]1[C:12](=[O:13])[O:14][CH3:15]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([NH2:10])[c:11]1[C:12](=[O:13])[O:14][CH3:15] | COC(=O)c1cccc([N+](=O)[O-])c1C(=O)OC | COC(=O)c1cccc(N)c1C(=O)OC | null | [Pd] | C(C)(=O)OCC | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]-[C:5](-[#8:6])=[O;D1;H0:7]>>[#8:6]-[C:5](=[O;D1;H0:7])-[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3] | 87 | [{"value": 87.0, "product": "COC(C1=C(C(=CC=C1)N)C(=O)OC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.9, "product": "COC(C1=C(C(=CC=C1)N)C(=O)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of methyl-2-(methoxycarbonyl)-3-nitrobenzoate (23.8 g, 99.51 mmol) in ethyl acetate (200 ml) was added 10% Pd/C (1.8 g). The mixture was hydrogenated under 50 psi of hydrogen for 3 hours in a Parr Type Shaker. The mixture was filtered through Celite and the filtrate was concentrated in vacuo to yield an o... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Pd].C(C)(=O)OCC | null | null | COC(=O)c1cccc([N+](=O)[O-])c1C(=O)OC>[Pd].C(C)(=O)OCC>COC(=O)c1cccc(N)c1C(=O)OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f3fbdfaa7453431a828019fad456e009 | COC(=O)c1cccc(N)c1C(=O)OC>>COC(=O)c1cccc(C#N)c1C(=O)OC | C([O-])([O-])=O.[Na+].[Na+].COC(C1=C(C(=CC=C1)N)C(=O)OC)=O.Cl.N(=O)[O-].[Na+].C(#N)[Cu].[C-]#N.[K+]>>COC(C1=C(C(=CC=C1)C#N)C(=O)OC)=O | N[c:9]1[cH:8][cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:12]1[C:13](=[O:14])[O:15][CH3:16]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([C:10]#[N:11])[c:12]1[C:13](=[O:14])[O:15][CH3:16] | COC(=O)c1cccc(N)c1C(=O)OC | COC(=O)c1cccc(C#N)c1C(=O)OC | null | null | O | Miscellaneous | OtherReaction | 803ab123dd5297cb23d9a6340952837f436e629c02fa01486d208bb7e2b4e208 | fb780e6912aa057969f5ca1e3a4b096c038904d81ac37783ac8b177057c79824 | c1ccccc1 | N-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](=[O;D1;H0:6])-[#8:7]-[C;D1;H3:8]):[c:9]-[C:10](-[#8:11])=[O;D1;H0:12]>>[#8:11]-[C:10](=[O;D1;H0:12])-[c:9]:[c:4](-[C:5](=[O;D1;H0:6])-[#8:7]-[C;D1;H3:8]):[c;H0;D3;+0:1](-[C:13]#[N;D1;H0:14]):[c:2]:[c:3] | 69.6 | [{"value": 65.0, "product": "COC(C1=C(C(=CC=C1)C#N)C(=O)OC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.6, "product": "COC(C1=C(C(=CC=C1)C#N)C(=O)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a stirred suspension of methyl-3-amino-2-(methoxycarbonyl)benzoate (17.0 g, 81 mmol) in a mixture of concentrated HCl (44 ml) and water (440 ml) at 4° C. was added a solution of NaNO2 (6.73 g, 97 mmol) in water (25 ml) dropwise at 4–5° C. Stirring was continued for 30 min at 4° C. The mixture was then carefully neut... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Nitrile | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | O | null | 0.5 | COC(=O)c1cccc(N)c1C(=O)OC>O>COC(=O)c1cccc(C#N)c1C(=O)OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-916b8d7dc5c84d9a98e9df7c5db82668 | COC(=O)c1cccc(C#N)c1C(=O)OC>>COC(=O)c1cccc(CN)c1C(=O)OC | COC(C1=C(C(=CC=C1)C#N)C(=O)OC)=O.Cl.[H][H]>>Cl.COC(C1=C(C(=CC=C1)CN)C(=O)OC)=O | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([C:10]#[N:11])[c:12]1[C:13](=[O:14])[O:15][CH3:16]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([CH2:10][NH2:11])[c:12]1[C:13](=[O:14])[O:15][CH3:16] | COC(=O)c1cccc(C#N)c1C(=O)OC | COC(=O)c1cccc(CN)c1C(=O)OC | null | [Pd] | CO | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | c1ccccc1 | [#8:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5](-[C;H0;D2;+0:6]#[N;H0;D1;+0:7]):[c:8]>>[#8:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5](-[CH2;D2;+0:6]-[NH2;D1;+0:7]):[c:8] | 90 | [{"value": 90.0, "product": "Cl.COC(C1=C(C(=CC=C1)CN)C(=O)OC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of methyl-3-cyano-2-(methoxycarbonyl)benzoate (12.3 g, 57 mmol) in methanol (250 ml) and 4N HCl (40 ml) was added 10% Pd/C (1.2 g). The mixture was hydrogenated under 50 psi of hydrogen in a Parr Type Shaker for 17 hours. The mixture was filtered through Celite and the filtrate was concentrated in vacuo. ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccccc1 | null | [Pd].CO | null | 1 | COC(=O)c1cccc(C#N)c1C(=O)OC>[Pd].CO>COC(=O)c1cccc(CN)c1C(=O)OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bae69bccc992457a8d4c901678105e5d | COC(=O)c1cccc(CNC(=O)OC(C)(C)C)c1C(=O)OC.NC1CCC(=O)NC1=O>>CC(C)(C)OC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | COC(C1=C(C(=CC=C1)CNC(=O)OC(C)(C)C)C(=O)OC)=O.Cl.NC1C(=O)NC(CC1)=O.O>>C(C)(C)(C)OC(NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O)=O | CO[C:16]([c:15]1[c:10]([CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[cH:11][cH:12][cH:13][c:14]1[C:27](OC)=[O:28])=[O:17].[NH2:18][CH:19]1[CH2:20][CH2:21][C:22](=[O:23])[NH:24][C:25]1=[O:26]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][c:14]2[c:15]1[C:16](=... | COC(=O)c1cccc(CNC(=O)OC(C)(C)C)c1C(=O)OC.NC1CCC(=O)NC1=O | CC(C)(C)OC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | null | null | CN(C)C=O | Acylation | OtherReaction | 5f64929c1c2079c3d863eee56c118a4bdc0a1a703582b3736d841c330e15e1d1 | 1e5c0ca760aaa3fc501cc1dfd7cf7fde58b645839335e018bc16acebad3ae4e5 | O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[C;H0;D3;+0:6](=[O;D1;H0:7])-O-C):[c:8].[C:9]-[C:10](-[NH2;D1;+0:11])-[C:12](=[O;D1;H0:13])-[#7:14]-[C:15]=[O;D1;H0:16]>>[C:9]-[C:10](-[N;H0;D3;+0:11]1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](:[c:8])-[C;H0;D3;+0:6]-1=[O;D1;H0:7])-[C:12](=[O;D1;H0:13])-[#7:1... | null | [] | 120 | CELSIUS | null | null | Diusopropylethylamine (3.20 g, 25 mmol) was added to a stirred suspension of methyl-3-[(t-butoxycarbonylamino)methyl]-2-(methoxycarbonyl)benzoate (8.00 g, 25 mmol) and aminoglutarimide hydrochloride (4.07 g, 25 mmol) in DMF (60 ml). The mixture was heated to 120° C. for 24 hours and then cooled to room temperature. The... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Primary amine | Substituted dicarboximide | null | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1CCNCC1 | HO- | CN(C)C=O | 120 | null | COC(=O)c1cccc(CNC(=O)OC(C)(C)C)c1C(=O)OC.NC1CCC(=O)NC1=O>CN(C)C=O>CC(C)(C)OC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-daecbc15b15e4ce4b96ea1b94528e11d | CC(=O)Cl.COC(=O)c1cccc(CN)c1C(=O)OC>>COC(=O)c1cccc(CNC(C)=O)c1C(=O)OC | C(C)N(CC)CC.Cl.COC(C1=C(C(=CC=C1)CN)C(=O)OC)=O.C(C)(=O)Cl>>COC(C=1C(C(=O)OC)=C(C=CC1)CNC(C)=O)=O | Cl[C:12]([CH3:13])=[O:14].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([CH2:10][NH2:11])[c:15]1[C:16](=[O:17])[O:18][CH3:19]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([CH2:10][NH:11][C:12]([CH3:13])=[O:14])[c:15]1[C:16](=[O:17])[O:18][CH3:19] | CC(=O)Cl.COC(=O)c1cccc(CN)c1C(=O)OC | COC(=O)c1cccc(CNC(C)=O)c1C(=O)OC | null | null | ClCCl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccccc1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[C:5]-[c:6]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[C:5]-[c:6] | 80 | [{"value": 80.0, "product": "COC(C=1C(C(=O)OC)=C(C=CC1)CNC(C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.8, "product": "COC(C=1C(C(=O)OC)=C(C=CC1)CNC(C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 4 | CELSIUS | null | null | Triethylamine (1.87 g, 18 mmol) was added slowly to a stirred suspension of methyl-3-(aminomethyl)-2-(methoxycarbonyl)benzoate hydrochloride (2.0 g, 8 mmol) in dichloromethane (30 ml). The resulting mixture was cooled in an ice bath to 4° C. Acetyl chloride (0.73 g, 9 mmol) was added dropwise at a rate such that the te... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1 | HCl | ClCCl | 4 | null | CC(=O)Cl.COC(=O)c1cccc(CN)c1C(=O)OC>ClCCl>COC(=O)c1cccc(CNC(C)=O)c1C(=O)OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7104d6d60d7c4909895bb7a01f22a534 | COC(=O)c1cccc(CNC(C)=O)c1C(=O)OC.NC1CCC(=O)NC1=O>>CC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | N12CCCCCC2=NCCC1.COC(C=1C(C(=O)OC)=C(C=CC1)CNC(C)=O)=O.Cl.NC1C(=O)NC(CC1)=O>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(C)=O)=O)=O | CO[C:12]([c:11]1[c:6]([CH2:5][NH:4][C:2]([CH3:1])=[O:3])[cH:7][cH:8][cH:9][c:10]1[C:23](OC)=[O:24])=[O:13].[NH2:14][CH:15]1[CH2:16][CH2:17][C:18](=[O:19])[NH:20][C:21]1=[O:22]>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][c:10]2[c:11]1[C:12](=[O:13])[N:14]([CH:15]1[CH2:16][CH2:17][C:18](=[O:19])[NH:20][C:2... | COC(=O)c1cccc(CNC(C)=O)c1C(=O)OC.NC1CCC(=O)NC1=O | CC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | null | null | CN(C)C=O | Acylation | OtherReaction | 5f64929c1c2079c3d863eee56c118a4bdc0a1a703582b3736d841c330e15e1d1 | 1e5c0ca760aaa3fc501cc1dfd7cf7fde58b645839335e018bc16acebad3ae4e5 | O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[C;H0;D3;+0:6](=[O;D1;H0:7])-O-C):[c:8].[C:9]-[C:10](-[NH2;D1;+0:11])-[C:12](=[O;D1;H0:13])-[#7:14]-[C:15]=[O;D1;H0:16]>>[C:9]-[C:10](-[N;H0;D3;+0:11]1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](:[c:8])-[C;H0;D3;+0:6]-1=[O;D1;H0:7])-[C:12](=[O;D1;H0:13])-[#7:1... | 22.8 | [{"value": 22.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(C)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 22.8, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(C)=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | 1,8-Diazabicyclo[5,4,0]undec-7-ene (0.93 g, 6 mmol) was added dropwise to a stirred suspension of 3-(acetylamino-methyl)-phthalic acid dimethyl ester (1.61 g, 6.0 mmol) and aminoglutarimide hydrochloride (1.0 g, 6.0 mmol) in DMF (15 ml). The mixture was then heated to 120° C. for 24 hours. The cooled mixture was concen... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Primary amine | Substituted dicarboximide | null | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1CCNCC1 | HO- | CN(C)C=O | 120 | null | COC(=O)c1cccc(CNC(C)=O)c1C(=O)OC.NC1CCC(=O)NC1=O>CN(C)C=O>CC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f680c87b1bd94a1fb587e8c844f25a45 | COC(=O)c1cccc(CN)c1C(=O)OC.O=C(Cl)C1CC1>>COC(=O)c1cccc(CNC(=O)C2CC2)c1C(=O)OC | C(C)N(CC)CC.Cl.COC(C1=C(C(=CC=C1)CN)C(=O)OC)=O.C1(CC1)C(=O)Cl>>COC(C1=C(C(=CC=C1)CNC(=O)C1CC1)C(=O)OC)=O | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([CH2:10][NH2:11])[c:17]1[C:18](=[O:19])[O:20][CH3:21].Cl[C:12](=[O:13])[CH:14]1[CH2:15][CH2:16]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([CH2:10][NH:11][C:12](=[O:13])[CH:14]2[CH2:15][CH2:16]2)[c:17]1[C:18](=[O:19])[O:20][CH3:21] | COC(=O)c1cccc(CN)c1C(=O)OC.O=C(Cl)C1CC1 | COC(=O)c1cccc(CNC(=O)C2CC2)c1C(=O)OC | null | null | ClCCl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCc1ccccc1)C1CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[C:5]-1.[NH2;D1;+0:6]-[C:7]-[c:8]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[C:7]-[c:8])-[C:3]1-[C:4]-[C:5]-1 | 103 | [{"value": 93.0, "product": "COC(C1=C(C(=CC=C1)CNC(=O)C1CC1)C(=O)OC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 103.0, "product": "COC(C1=C(C(=CC=C1)CNC(=O)C1CC1)C(=O)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 4 | CELSIUS | 30 | MINUTE | Triethylamine (1.87 g, 18 mmol) was added dropwise to a stirred suspension of methyl-3-(aminomethyl)-2-(methoxycarbonyl)benzoate hydrochloride (2.0 g, 7 mmol) in dichloromethane (40 ml). The mixture was cooled in an ice bath to 4° C. Cyclopropylcarbonyl chloride (0.99 g, 9 mmol) was added slowly at 4–8° C. After additi... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC1 | HCl | ClCCl | 4 | 0.5 | COC(=O)c1cccc(CN)c1C(=O)OC.O=C(Cl)C1CC1>ClCCl>COC(=O)c1cccc(CNC(=O)C2CC2)c1C(=O)OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f5b061a4b05e467a82627edddb901922 | CCOC(=O)Cl.COC(=O)c1cccc(CN)c1C(=O)OC>>CCOC(=O)NCc1cccc(C(=O)OC)c1C(=O)OC | C(C)N(CC)CC.Cl.COC(C1=C(C(=CC=C1)CN)C(=O)OC)=O.ClC(=O)OCC>>COC(C1=C(C(=CC=C1)CNC(=O)OCC)C(=O)OC)=O | Cl[C:4]([O:3][CH2:2][CH3:1])=[O:5].[NH2:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]([C:13](=[O:14])[O:15][CH3:16])[c:17]1[C:18](=[O:19])[O:20][CH3:21]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[NH:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]([C:13](=[O:14])[O:15][CH3:16])[c:17]1[C:18](=[O:19])[O:20][CH3:21] | CCOC(=O)Cl.COC(=O)c1cccc(CN)c1C(=O)OC | CCOC(=O)NCc1cccc(C(=O)OC)c1C(=O)OC | null | null | ClCCl | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[NH2;D1;+0:5]-[C:6]-[c:7]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[C:6]-[c:7] | 70 | [{"value": 70.0, "product": "COC(C1=C(C(=CC=C1)CNC(=O)OCC)C(=O)OC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.3, "product": "COC(C1=C(C(=CC=C1)CNC(=O)OCC)C(=O)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 4 | CELSIUS | 30 | MINUTE | Triethylamine (1.57 g, 18.5 mmol) was added to a stirred suspension of methyl-3-(aminomethyl)-2-(methoxycarbonyl)benzoate hydrochloride (2.0 g, 8 mmol) in dichloromethane (30 ml). The mixture was cooled in an ice bath to 4° C. Ethyl chloroformate (1.0 g, 9 mmol) was added slowly keeping the mixture at 4–6° C. After add... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccccc1 | HCl | ClCCl | 4 | 0.5 | CCOC(=O)Cl.COC(=O)c1cccc(CN)c1C(=O)OC>ClCCl>CCOC(=O)NCc1cccc(C(=O)OC)c1C(=O)OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6ebefc0c0c2647b2b8ee5f59d2e48aa8 | CCOC(=O)NCc1cccc(C(=O)OC)c1C(=O)OC.NC1CCC(=O)NC1=O>>CCOC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | O.N12CCCCCC2=NCCC1.COC(C1=C(C(=CC=C1)CNC(=O)OCC)C(=O)OC)=O.Cl.NC1C(=O)NC(CC1)=O>>C(C)OC(NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O)=O | CO[C:14]([c:13]1[c:8]([CH2:7][NH:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:9][cH:10][cH:11][c:12]1[C:25](OC)=[O:26])=[O:15].[NH2:16][CH:17]1[CH2:18][CH2:19][C:20](=[O:21])[NH:22][C:23]1=[O:24]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[NH:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[C:14](=[O:15])[N:16]([CH:17]1[CH2:18][CH2:1... | CCOC(=O)NCc1cccc(C(=O)OC)c1C(=O)OC.NC1CCC(=O)NC1=O | CCOC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | null | null | CN(C)C=O | Acylation | OtherReaction | 5f64929c1c2079c3d863eee56c118a4bdc0a1a703582b3736d841c330e15e1d1 | 1e5c0ca760aaa3fc501cc1dfd7cf7fde58b645839335e018bc16acebad3ae4e5 | O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[C;H0;D3;+0:6](=[O;D1;H0:7])-O-C):[c:8].[C:9]-[C:10](-[NH2;D1;+0:11])-[C:12](=[O;D1;H0:13])-[#7:14]-[C:15]=[O;D1;H0:16]>>[C:9]-[C:10](-[N;H0;D3;+0:11]1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](:[c:8])-[C;H0;D3;+0:6]-1=[O;D1;H0:7])-[C:12](=[O;D1;H0:13])-[#7:1... | 46.8 | [{"value": 45.0, "product": "C(C)OC(NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.8, "product": "C(C)OC(NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | 1,8-Diazabicyclo[5,4,0]undec-7-ene (0.8 g, 5 mmol) was added to a stirred suspension of methyl-3-[(ethoxycarbonylamino)methyl]-2-(methoxycarbonyl)benzoate (1.54 g, 5 mmol) and aminoglutarimide hydrochloride (0.86 g, 5 mmol) in DMF (15 ml). The mixture was heated to 120° C. for 24 hours. The mixture was cooled to room t... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Primary amine | Substituted dicarboximide | null | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1CCNCC1 | HO- | CN(C)C=O | 120 | null | CCOC(=O)NCc1cccc(C(=O)OC)c1C(=O)OC.NC1CCC(=O)NC1=O>CN(C)C=O>CCOC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3def3715b4dc4e31a7dc2480193bc963 | COC(=O)c1cccc(CN)c1C(=O)OC.O=C(Cl)OCc1ccccc1>>COC(=O)c1cccc(CNC(=O)OCc2ccccc2)c1C(=O)OC | C(C)N(CC)CC.Cl.COC(C1=C(C(=CC=C1)CN)C(=O)OC)=O.ClC(=O)OCC1=CC=CC=C1>>COC(C1=C(C(=CC=C1)CNC(=O)OCC1=CC=CC=C1)C(=O)OC)=O | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([CH2:10][NH2:11])[c:22]1[C:23](=[O:24])[O:25][CH3:26].Cl[C:12](=[O:13])[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([CH2:10][NH:11][C:12](=[O:13])[O:14][CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][... | COC(=O)c1cccc(CN)c1C(=O)OC.O=C(Cl)OCc1ccccc1 | COC(=O)c1cccc(CNC(=O)OCc2ccccc2)c1C(=O)OC | null | null | ClCCl | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | O=C(NCc1ccccc1)OCc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[NH2;D1;+0:5]-[C:6]-[c:7]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[C:6]-[c:7] | 76 | [{"value": 76.0, "product": "COC(C1=C(C(=CC=C1)CNC(=O)OCC1=CC=CC=C1)C(=O)OC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.5, "product": "COC(C1=C(C(=CC=C1)CNC(=O)OCC1=CC=CC=C1)C(=O)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 4 | CELSIUS | 30 | MINUTE | Triethylamine (1.87 g, 18.5 mmol) was added to a stirred suspension of methyl-3-(aminomethyl)-2-(methoxycarbonyl)benzoate hydrochloride (2.0 g, 8 mmol) in dichloromethane (30 ml). The mixture was cooled in an ice bath to 4° C. Benzyl chloroformate (1.66 g, 10 mmol) was added slowly keeping the temperature between 4–7° ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccccc1.c1ccccc1 | HCl | ClCCl | 4 | 0.5 | COC(=O)c1cccc(CN)c1C(=O)OC.O=C(Cl)OCc1ccccc1>ClCCl>COC(=O)c1cccc(CNC(=O)OCc2ccccc2)c1C(=O)OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6e7757d056d64b50a575967eea16aa46 | COC(=O)c1cccc(CNC(=O)OCc2ccccc2)c1C(=O)OC.NC1CCC(=O)NC1=O>>O=C1CCC(N2C(=O)c3cccc(CNC(=O)OCc4ccccc4)c3C2=O)C(=O)N1 | O.N12CCCCCC2=NCCC1.COC(C1=C(C(=CC=C1)CNC(=O)OCC1=CC=CC=C1)C(=O)OC)=O.Cl.NC1C(=O)NC(CC1)=O>>C(C1=CC=CC=C1)OC(NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O)=O | CO[C:7](=[O:8])[c:9]1[cH:10][cH:11][cH:12][c:13]([CH2:14][NH:15][C:16](=[O:17])[O:18][CH2:19][c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[c:26]1[C:27](OC)=[O:28].[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([NH2:6])[C:29](=[O:30])[NH:31]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([CH2:1... | COC(=O)c1cccc(CNC(=O)OCc2ccccc2)c1C(=O)OC.NC1CCC(=O)NC1=O | O=C1CCC(N2C(=O)c3cccc(CNC(=O)OCc4ccccc4)c3C2=O)C(=O)N1 | null | null | CN(C)C=O | Acylation | OtherReaction | 5f64929c1c2079c3d863eee56c118a4bdc0a1a703582b3736d841c330e15e1d1 | 1e5c0ca760aaa3fc501cc1dfd7cf7fde58b645839335e018bc16acebad3ae4e5 | O=C1CCC(N2C(=O)c3cccc(CNC(=O)OCc4ccccc4)c3C2=O)C(=O)N1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[C;H0;D3;+0:6](=[O;D1;H0:7])-O-C):[c:8].[C:9]-[C:10](-[NH2;D1;+0:11])-[C:12](=[O;D1;H0:13])-[#7:14]-[C:15]=[O;D1;H0:16]>>[C:9]-[C:10](-[N;H0;D3;+0:11]1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](:[c:8])-[C;H0;D3;+0:6]-1=[O;D1;H0:7])-[C:12](=[O;D1;H0:13])-[#7:1... | 24 | [{"value": 24.0, "product": "C(C1=CC=CC=C1)OC(NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 22.9, "product": "C(C1=CC=CC=C1)OC(NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | 1,8-diazabicyclo[5,4,0]undec-7-ene (0.88 g, 6 mmol) was added to a stirred suspension of methyl-3-[(benzyloxycarbonylamino)methyl]-2-(methoxycarbonyl)benzoate (2.07 g, 6 mmol) and aminoglutarimide hydrochloride (0.95 g, 6 mmol) in DMF (15 ml). The mixture was heated to 120° C. for 24 hours. The mixture was cooled to ro... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Primary amine | Substituted dicarboximide | null | c1ccc2c(c1)C[NH]C2 | C1CCNCC1.c1ccc2c(c1)C[NH]C2.c1ccccc1 | HO- | CN(C)C=O | 120 | null | COC(=O)c1cccc(CNC(=O)OCc2ccccc2)c1C(=O)OC.NC1CCC(=O)NC1=O>CN(C)C=O>O=C1CCC(N2C(=O)c3cccc(CNC(=O)OCc4ccccc4)c3C2=O)C(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1ee78c18a1d941e898b47b0f3e233f67 | NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)CCl>>O=C(CCl)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | C(C)N(CC)CC.Cl.NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.ClCC(=O)Cl>>ClCC(=O)NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O | [NH2:5][CH2:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[C:13](=[O:14])[N:15]([CH:16]1[CH2:17][CH2:18][C:19](=[O:20])[NH:21][C:22]1=[O:23])[C:24]2=[O:25].Cl[C:2](=[O:1])[CH2:3][Cl:4]>>[O:1]=[C:2]([CH2:3][Cl:4])[NH:5][CH2:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[C:13](=[O:14])[N:15]([CH:16]1[CH2:17][CH2:18][C:19](=[O:20])... | NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)CCl | O=C(CCl)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | null | null | C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Cl;D1;H0:4].[NH2;D1;+0:5]-[C:6]-[c:7]>>[Cl;D1;H0:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[C:6]-[c:7] | 84 | [{"value": 84.0, "product": "ClCC(=O)NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.6, "product": "ClCC(=O)NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | Triethylamine (0.6 g, 6 mmol) was added to a stirred suspension of 4-(aminomethyl)-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione hydrochloride (0.8 g, 2.5 mmol) in THF (70 ml). After stirring for 5 min, chloroacetyl chloride (0.34 g, 3 mmol) was added and the resulting mixture was heated at reflux for 3 hours. The so... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2c(c1)C[NH]C2.C1CCNCC1 | HCl | C1CCOC1 | null | 0.083333 | NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)CCl>C1CCOC1>O=C(CCl)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0da40745003242e48464c19a6e39afa5 | CC(C)(C)N=C=O.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>>CC(C)(C)NC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | N12CCCCCC2=NCCC1.Cl.NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.C(C)(C)(C)N=C=O>>C(C)(C)(C)NC(=O)NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[N:5]=[C:6]=[O:7].[NH2:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][c:14]2[c:15]1[C:16](=[O:17])[N:18]([CH:19]1[CH2:20][CH2:21][C:22](=[O:23])[NH:24][C:25]1=[O:26])[C:27]2=[O:28]>>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][C:6](=[O:7])[NH:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][c:14]2[c:15]1[C:16](=[O:17... | CC(C)(C)N=C=O.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | CC(C)(C)NC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | null | null | C(C)#N | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[N;H0;D2;+0:5]=[C;H0;D2;+0:6]=[O;D1;H0:7].[NH2;D1;+0:8]-[C:9]-[c:10]>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[NH;D2;+0:8]-[C:9]-[c:10] | 51 | [{"value": 51.0, "product": "C(C)(C)(C)NC(=O)NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.0, "product": "C(C)(C)(C)NC(=O)NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1,8-Diazabicyclo[5,4,0]undec-7-ene (0.28 g, 1.9 mmol) was added to stirred suspension of 4-(aminomethyl)-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione hydrochloride (0.6 g, 1.9 mmol) in acetonitrile (50 ml). After stirring for 1 hour, t-butylisocyanate (0.21 g, 2 mmol) was added. The mixture was stirred at room tempe... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccc2c(c1)C[NH]C2.C1CCNCC1 | null | C(C)#N | null | null | CC(C)(C)N=C=O.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>C(C)#N>CC(C)(C)NC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d6c052b5e4264548a1573f008ef022f3 | CC(C)(C)CC(=O)Cl.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>>CC(C)(C)CC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | N12CCCCCC2=NCCC1.Cl.NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.C(C)(C)(C)CC(=O)Cl>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(CC(C)(C)C)=O)=O)=O | Cl[C:6]([CH2:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].[NH2:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][c:14]2[c:15]1[C:16](=[O:17])[N:18]([CH:19]1[CH2:20][CH2:21][C:22](=[O:23])[NH:24][C:25]1=[O:26])[C:27]2=[O:28]>>[CH3:1][C:2]([CH3:3])([CH3:4])[CH2:5][C:6](=[O:7])[NH:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][c:14]2[c:15]1[C:16](... | CC(C)(C)CC(=O)Cl.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | CC(C)(C)CC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | null | null | C(C)#N | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[C:6]-[c:7]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[C:6]-[c:7] | null | [] | null | null | 20 | MINUTE | 1,8-Diazabicyclo[5,4,0]undec-7-ene (0.62 g, 4 mmol) was added to a stirred suspension of 4-(aminomethyl)-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione hydrochloride (0.6 g, 1.9 mmol) in acetonitrile (50 ml). After stirring for 20 min, t-butylacetyl chloride (0.25 g, 1.9 mmol) was added. The mixture was stirred at roo... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2c(c1)C[NH]C2.C1CCNCC1 | HCl | C(C)#N | null | 0.333333 | CC(C)(C)CC(=O)Cl.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>C(C)#N>CC(C)(C)CC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b5f01c76dcc04a9ab51771e818636cb8 | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1cccnc1>>O=C1CCC(N2C(=O)c3cccc(NC(=O)c4cccnc4)c3C2=O)C(=O)N1 | NC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.Cl.C(C1=CN=CC=C1)(=O)Cl>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(=O)C=1C=NC=CC1)=O)=O | [O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([NH2:14])[c:23]3[C:24]2=[O:25])[C:26](=[O:27])[NH:28]1.Cl[C:15](=[O:16])[c:17]1[cH:18][cH:19][cH:20][n:21][cH:22]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([NH:14][C:15](=[O:16])[c:17]4[cH... | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1cccnc1 | O=C1CCC(N2C(=O)c3cccc(NC(=O)c4cccnc4)c3C2=O)C(=O)N1 | null | null | O.O1CCCC1.CCOCC | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CCC(N2C(=O)c3cccc(NC(=O)c4cccnc4)c3C2=O)C(=O)N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7].[#7:8]-[C:9](=[O;D1;H0:10])-[c:11]:[c:12](-[NH2;D1;+0:13]):[c:14]>>[#7:8]-[C:9](=[O;D1;H0:10])-[c:11]:[c:12](-[NH;D2;+0:13]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7]):[c:14] | 79.3 | [{"value": 79.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(=O)C=1C=NC=CC1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.3, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(=O)C=1C=NC=CC1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred mixture of 4-amino-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione (1.09 g, 4.0 mmol) and nicotinoyl chloride hydrochloride (1.42 g, 8.0 mmol) in tetrahydrofuran (60 ml) was heated to reflux for 22 h. The suspension was filtered and washed with tetrahydrofuran (20 ml) and ether (10 ml) to yield a white solid.... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CCNCC1.c1ccc2c(c1)C[NH]C2.c1ccncc1 | HCl | O.O1CCCC1.CCOCC | null | null | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1cccnc1>O.O1CCCC1.CCOCC>O=C1CCC(N2C(=O)c3cccc(NC(=O)c4cccnc4)c3C2=O)C(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cd0e622d7e2b4c538ea2130286c65fec | Nc1cccc2c1CN(C1CCC(=O)NC1=O)C2=O.O=Cc1ccccc1>>O=C1CCC(N2Cc3c(NCc4ccccc4)cccc3C2=O)C(=O)N1 | NC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O.C(C1=CC=CC=C1)=O.[BH4-].[Na+]>>O=C1N(CC2=C(C=CC=C12)NCC1=CC=CC=C1)C1C(NC(CC1)=O)=O | [O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[CH2:7][c:8]3[c:9]([NH2:10])[cH:18][cH:19][cH:20][c:21]3[C:22]2=[O:23])[C:24](=[O:25])[NH:26]1.O=[CH:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[CH2:7][c:8]3[c:9]([NH:10][CH2:11][c:12]4[cH:13][cH:14][cH:15][cH:16][cH:17]4)[cH:18][cH:19][... | Nc1cccc2c1CN(C1CCC(=O)NC1=O)C2=O.O=Cc1ccccc1 | O=C1CCC(N2Cc3c(NCc4ccccc4)cccc3C2=O)C(=O)N1 | null | null | CO.C(C)(=O)O | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | O=C1CCC(N2Cc3c(NCc4ccccc4)cccc3C2=O)C(=O)N1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8]):[c:4] | 60.1 | [{"value": 60.0, "product": "O=C1N(CC2=C(C=CC=C12)NCC1=CC=CC=C1)C1C(NC(CC1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.1, "product": "O=C1N(CC2=C(C=CC=C12)NCC1=CC=CC=C1)C1C(NC(CC1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A stirred mixture of 3-(4-amino-1-oxoisoindolin-2-yl)piperidine-2,6-dione (518 mg, 2.0 mmol) and benzaldehyde (0.21 ml, 2.0 mmol) in methanol (20 ml) was heated to reflux for 5 h. The solvent was removed in vacuo to give a solid. The solid was re-dissolved in acetic acid (20 ml). The stirred solution was heated to refl... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | C1CCNCC1.c1ccccc1.c1ccc2c(c1)C[NH]C2 | Other | CO.C(C)(=O)O | null | 18 | Nc1cccc2c1CN(C1CCC(=O)NC1=O)C2=O.O=Cc1ccccc1>CO.C(C)(=O)O>O=C1CCC(N2Cc3c(NCc4ccccc4)cccc3C2=O)C(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ea6cf2a4adb041cdad97be0ac9ef9740 | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=Cc1ccccc1>>O=C1CCC(N2C(=O)c3cccc(NCc4ccccc4)c3C2=O)C(=O)N1 | C(C1=CC=CC=C1)=O.NC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.C(C1=CC=CC=C1)=O.[BH4-].[Na+].[BH4-].[Na+]>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NCC1=CC=CC=C1)=O)=O | [O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([NH2:14])[c:22]3[C:23]2=[O:24])[C:25](=[O:26])[NH:27]1.O=[CH:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([NH:14][CH2:15][c:16]4[cH:17][cH:18][cH... | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=Cc1ccccc1 | O=C1CCC(N2C(=O)c3cccc(NCc4ccccc4)c3C2=O)C(=O)N1 | null | null | C(C)(=O)O.C(C)(=O)OCC.C(O)([O-])=O.[Na+] | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | O=C1CCC(N2C(=O)c3cccc(NCc4ccccc4)c3C2=O)C(=O)N1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](-[NH2;D1;+0:10]):[c:11]>>[#7:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](-[NH;D2;+0:10]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:11] | 16 | [{"value": 16.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NCC1=CC=CC=C1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 15.6, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NCC1=CC=CC=C1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 17 | HOUR | A mixture of 4-amino-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione (1.0 g, 3.7 mmol) and benzaldehyde (0.4 ml, 3.9 mmol) in acetic acid (20 ml) was stirred at room temperature for 17 h, then was heated to reflux for 3 h. The mixture was cooled to room temperature. To the stirred mixture was added sodium borohydride (... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | C1CCNCC1.c1ccc2c(c1)C[NH]C2.c1ccccc1 | Other | C(C)(=O)O.C(C)(=O)OCC.C(O)([O-])=O.[Na+] | null | 17 | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=Cc1ccccc1>C(C)(=O)O.C(C)(=O)OCC.C(O)([O-])=O.[Na+]>O=C1CCC(N2C(=O)c3cccc(NCc4ccccc4)c3C2=O)C(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-388df57f02f0443291b94e4b8f0ad28c | CCC(=O)Cl.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>>CCC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | N12CCCCCC2=NCCC1.Cl.NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.C(CC)(=O)Cl>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(CC)=O)=O)=O | Cl[C:3]([CH2:2][CH3:1])=[O:4].[NH2:5][CH2:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[C:13](=[O:14])[N:15]([CH:16]1[CH2:17][CH2:18][C:19](=[O:20])[NH:21][C:22]1=[O:23])[C:24]2=[O:25]>>[CH3:1][CH2:2][C:3](=[O:4])[NH:5][CH2:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[C:13](=[O:14])[N:15]([CH:16]1[CH2:17][CH2:18][C:19](=[O:20... | CCC(=O)Cl.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | CCC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | null | null | CC#N | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C;D1;H3:4].[NH2;D1;+0:5]-[C:6]-[c:7]>>[C;D1;H3:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[C:6]-[c:7] | null | [] | null | null | 20 | MINUTE | 1,8-Diazabicyclo[5,4,0]undec-7-ene (0.65 g, 4.25 mmol) was added to a stirred suspension of 4-(aminomethyl)-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione hydrochloride (0.6 g, 1.85 mmol) in CH3CN (50 ml). After stirring for 20 min, propionyl chloride (0.2 g, 2.13 mmol) was added. The mixture was stirred at room tempe... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2c(c1)C[NH]C2.C1CCNCC1 | HCl | CC#N | null | 0.333333 | CCC(=O)Cl.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>CC#N>CCC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-74d7240ff2e84224859a91ea47c8879c | NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1cccnc1>>O=C1CCC(N2C(=O)c3cccc(CNC(=O)c4cccnc4)c3C2=O)C(=O)N1 | N12CCCCCC2=NCCC1.Cl.NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.C(C1=CN=CC=C1)(=O)Cl>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)C=1C=NC=CC1)=O)=O | [O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([CH2:14][NH2:15])[c:24]3[C:25]2=[O:26])[C:27](=[O:28])[NH:29]1.Cl[C:16](=[O:17])[c:18]1[cH:19][cH:20][cH:21][n:22][cH:23]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([CH2:14][NH:15][C:16](=[... | NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1cccnc1 | O=C1CCC(N2C(=O)c3cccc(CNC(=O)c4cccnc4)c3C2=O)C(=O)N1 | null | null | CC#N | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CCC(N2C(=O)c3cccc(CNC(=O)c4cccnc4)c3C2=O)C(=O)N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7].[NH2;D1;+0:8]-[C:9]-[c:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:8]-[C:9]-[c:10])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | 64.7 | [{"value": 64.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)C=1C=NC=CC1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.7, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)C=1C=NC=CC1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1,8-Diazabicyclo[5,4,0]undec-7-ene (0.98 g, 6.48 mmol) was added to stirred suspension of 4-(aminomethyl)-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione hydrochloride (0.6 g, 1.85 mmol) in CH3CN (50 ml). After stirring for 20 min, nicotinoyl chloride (0.41 g, 2.22 mmol) was added. The mixture was stirred at room tempe... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CCNCC1.c1ccc2c(c1)C[NH]C2.c1ccncc1 | HCl | CC#N | null | null | NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1cccnc1>CC#N>O=C1CCC(N2C(=O)c3cccc(CNC(=O)c4cccnc4)c3C2=O)C(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a89f88578ccf4115918213f8094fcd89 | CCCCCCC(=O)Cl.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>>CCCCCCC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | N12CCCCCC2=NCCC1.Cl.NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.C(CCCCCC)(=O)Cl>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(CCCCCC)=O)=O)=O | Cl[C:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:8].[NH2:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][c:15]2[c:16]1[C:17](=[O:18])[N:19]([CH:20]1[CH2:21][CH2:22][C:23](=[O:24])[NH:25][C:26]1=[O:27])[C:28]2=[O:29]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7](=[O:8])[NH:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][c:15]2[c... | CCCCCCC(=O)Cl.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | CCCCCCC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | null | null | CC#N | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[C:6]-[c:7]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[C:6]-[c:7] | 66.3 | [{"value": 66.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(CCCCCC)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.3, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(CCCCCC)=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | 1,8-Diazabicyclo[5,4,0]undec-7-ene (0.65 g, 2.22 mmol) was added to a stirred suspension of 4-(aminomethyl)-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione hydrochloride (0.6 g, 1.85 mmol) in CH3CN (50 ml). After stirring for 20 min, heptanoyl chloride (0.33 g, 2.22 mmol) was added. The mixture was stirred at room temp... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2c(c1)C[NH]C2.C1CCNCC1 | HCl | CC#N | null | 0.333333 | CCCCCCC(=O)Cl.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>CC#N>CCCCCCC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0c435fc15e3d4873a09518bc04ca9f38 | NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1ccco1>>O=C1CCC(N2C(=O)c3cccc(CNC(=O)c4ccco4)c3C2=O)C(=O)N1 | N12CCCCCC2=NCCC1.Cl.NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.O1C(=CC=C1)C(=O)Cl>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)C=1OC=CC1)=O)=O | [O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([CH2:14][NH2:15])[c:23]3[C:24]2=[O:25])[C:26](=[O:27])[NH:28]1.Cl[C:16](=[O:17])[c:18]1[cH:19][cH:20][cH:21][o:22]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([CH2:14][NH:15][C:16](=[O:17])[... | NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1ccco1 | O=C1CCC(N2C(=O)c3cccc(CNC(=O)c4ccco4)c3C2=O)C(=O)N1 | null | null | CC#N | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CCC(N2C(=O)c3cccc(CNC(=O)c4ccco4)c3C2=O)C(=O)N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6].[NH2;D1;+0:7]-[C:8]-[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:7]-[C:8]-[c:9])-[c:3](:[c:4]):[#8;a:5]:[c:6] | 73 | [{"value": 73.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)C=1OC=CC1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.3, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)C=1OC=CC1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | 1,8-Diazabicyclo[5,4,0]undec-7-ene (0.650 g, 2.22 mmol) was added to a stirred suspension of 4-(aminomethyl)-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione hydrochloride (0.600 g, 1.85 mmol) in CH3CN (50 ml). After stirring for 20 min, 2-furoyl chloride (0.290 g, 2.22 mmol) was added and the mixture was stirred at roo... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CCNCC1.c1ccc2c(c1)C[NH]C2.c1ccoc1 | HCl | CC#N | null | 0.333333 | NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1ccco1>CC#N>O=C1CCC(N2C(=O)c3cccc(CNC(=O)c4ccco4)c3C2=O)C(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7fef32c3685e4b6683f832c20f4ac0ba | O=C(CCl)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.[N-]=[N+]=[N-]>>[N-]=[N+]=NCC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | ClCC(=O)NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.[N-]=[N+]=[N-].[Na+].[I-].[Na+]>>N(=[N+]=[N-])CC(=O)NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O | Cl[CH2:4][C:5](=[O:6])[NH:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][c:13]2[c:14]1[C:15](=[O:16])[N:17]([CH:18]1[CH2:19][CH2:20][C:21](=[O:22])[NH:23][C:24]1=[O:25])[C:26]2=[O:27].[N-:1]=[N+:2]=[N-:3]>>[N-:1]=[N+:2]=[N:3][CH2:4][C:5](=[O:6])[NH:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][c:13]2[c:14]1[C:15](=[O:16])[N:17]([CH:18]1[... | O=C(CCl)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.[N-]=[N+]=[N-] | [N-]=[N+]=NCC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 4b07a4c2a14d792a37e78a751619e60b15c60cbff0bebae1109754fb52d84cbb | 2d41632f7225d65cdc2ad8562dfb28f3f5a017f92040ed4ccafbb8154954c8fe | O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1 | Cl-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[C:5].[N-;H0;D1:6]=[#7;+:7]=[N;-;D1;H0:8]>>[C:5]-[#7:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[N;H0;D2;+0:6]=[#7;+:7]=[N;-;D1;H0:8] | 90.8 | [{"value": 90.0, "product": "N(=[N+]=[N-])CC(=O)NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.8, "product": "N(=[N+]=[N-])CC(=O)NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-chloro-N-{[2-(2,6-dioxo(3-piperidyl))-1,3-dioxoisoindolin-4-yl]methyl}acetamide (1.3 g, 3.57 mmol), sodium azide (0.3 g, 4.65 mmol) and sodium iodide (0.54 g, 3.57 mmol) in acetone (50 ml) was refluxed for 17 hours. The solvent was removed in vacuo and the residue was dissolved in EtOAc (60 ml). The EtOA... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Azide | null | null | c1ccc2c(c1)C[NH]C2.C1CCNCC1 | Other | CC(=O)C | null | null | O=C(CCl)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.[N-]=[N+]=[N-]>CC(=O)C>[N-]=[N+]=NCC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0d99ab23700d4d1cb40179710f1a571b | [N-]=[N+]=NCC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>>NCC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | N(=[N+]=[N-])CC(=O)NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.Cl.[H][H]>>Cl.NCC(=O)NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O | [N-]=[N+]=[N:2][CH2:3][C:4](=[O:5])[NH:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[C:14](=[O:15])[N:16]([CH:17]1[CH2:18][CH2:19][C:20](=[O:21])[NH:22][C:23]1=[O:24])[C:25]2=[O:26]>>[NH2:2][CH2:3][C:4](=[O:5])[NH:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[C:14](=[O:15])[N:16]([CH:17]1[CH2:18][CH2:19][C:20](... | [N-]=[N+]=NCC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | NCC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | null | [Pd] | CO | Reduction | Azide to amine reduction (Staudinger) | 4c9e4990dae2bb965dec06bd45e318560989ee3681b61e443f7aa363b7cfa222 | cd009d687d606bf351eac9390a176d16be38f2c8216a599b398641009c215027 | O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1 | [C:1]-[#7:2]-[C:3](=[O;D1;H0:4])-[C:5]-[N;H0;D2;+0:6]=[N+]=[N-]>>[C:1]-[#7:2]-[C:3](=[O;D1;H0:4])-[C:5]-[NH2;D1;+0:6] | 84 | [{"value": 84.0, "product": "Cl.NCC(=O)NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-azido-N-{[2-(2,6-dioxo(3-piperidyl))-1,3-dioxoisoindolin-4-yl]methyl}acetamide (1.2 g, 3.24 mmol), and 10% Pd/C (0.15 g) in 4N HCl (20 ml) and CH3OH (50 ml) was hydrogenated in Parr shake apparatus under 50 psi of hydrogen for 3 hours. The mixture was then filtered through celite and the filtrate was con... | 10.6084/m9.figshare.5104873.v1 | null | Azide | Primary amine | null | null | c1ccc2c(c1)C[NH]C2.C1CCNCC1 | Other | [Pd].CO | null | null | [N-]=[N+]=NCC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>[Pd].CO>NCC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fdcfbfbdd1714689a16e5d665ea37a08 | CCOC(=O)CCCCCC(=O)Cl.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>>CCOC(=O)CCCCCC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | N12CCCCCC2=NCCC1.NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.C(C)OC(CCCCCC(=O)Cl)=O>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)CCCCCC(=O)OCC)=O)=O | Cl[C:11]([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])=[O:12].[NH2:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][c:19]2[c:20]1[C:21](=[O:22])[N:23]([CH:24]1[CH2:25][CH2:26][C:27](=[O:28])[NH:29][C:30]1=[O:31])[C:32]2=[O:33]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11](=[... | CCOC(=O)CCCCCC(=O)Cl.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | CCOC(=O)CCCCCC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | null | null | CC#N | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[C:6]-[c:7]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[C:6]-[c:7] | 50 | [{"value": 50.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)CCCCCC(=O)OCC)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | 1,8-Diazabicyclo[5,4,0]undec-7-ene (0.65 g, 4.26 mmol) was added to a stirred suspension of 4-(aminomethyl)-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione hydrocbloride (0.6 g, 1.85 mmol) in CH3CN (50 ml). After stirring for 20 min, 6-(chloroformyl)hexanoic acid ethyl ester (0.46 g, 2.22 mmol) was added. The mixture w... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2c(c1)C[NH]C2.C1CCNCC1 | HCl | CC#N | null | 0.333333 | CCOC(=O)CCCCCC(=O)Cl.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>CC#N>CCOC(=O)CCCCCC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9e53191210c54c80a7a976acd132a28e | CC(C)(C)OC(=O)NCCC(=O)O.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>>CC(C)(C)OC(=O)NCCC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | N12CCCCCC2=NCCC1.Cl.NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.ON1N=NC2=C1C=CC=C2.C(=O)(OC(C)(C)C)NCCC(=O)O.Cl.CN(CCCN=C=NCC)C>>C(C)(C)(C)OC(=O)NCCC(=O)NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O | O[C:11]([CH2:10][CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])=[O:12].[NH2:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][c:19]2[c:20]1[C:21](=[O:22])[N:23]([CH:24]1[CH2:25][CH2:26][C:27](=[O:28])[NH:29][C:30]1=[O:31])[C:32]2=[O:33]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][C:11](=... | CC(C)(C)OC(=O)NCCC(=O)O.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | CC(C)(C)OC(=O)NCCC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | null | null | CC#N | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[C:6]-[c:7]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[C:6]-[c:7] | 67.2 | [{"value": 67.0, "product": "C(C)(C)(C)OC(=O)NCCC(=O)NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.2, "product": "C(C)(C)(C)OC(=O)NCCC(=O)NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | 1,8-Diazabicyclo[5,4,0]undec-7-ene (0.7 g, 4.62 mmol) was added to a stirred suspension of 4-(aminomethyl)-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione hydrochloride (0.6 g, 1.85 mmol) in CH3CN (50 ml). After stirring for 20 min, 1-hydroxybenzotriazole (0.3 g, 2.22 mmol), N-BOC-b-alanine (0.42 g, 2.22 mol) and 1-[3-... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2c(c1)C[NH]C2.C1CCNCC1 | HO- | CC#N | null | 0.333333 | CC(C)(C)OC(=O)NCCC(=O)O.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>CC#N>CC(C)(C)OC(=O)NCCC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f071655f649c45b9b5667ad7ccc12f82 | CC(C)(C)OC(=O)NCCC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>>NCCC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | Cl.C(C)(C)(C)OC(=O)NCCC(=O)NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O>>Cl.NCCC(=O)NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O | CC(C)(C)OC(=O)[NH:2][CH2:3][CH2:4][C:5](=[O:6])[NH:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][c:13]2[c:14]1[C:15](=[O:16])[N:17]([CH:18]1[CH2:19][CH2:20][C:21](=[O:22])[NH:23][C:24]1=[O:25])[C:26]2=[O:27]>>[NH2:2][CH2:3][CH2:4][C:5](=[O:6])[NH:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][c:13]2[c:14]1[C:15](=[O:16])[N:17]([CH:18]1[C... | CC(C)(C)OC(=O)NCCC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | NCCC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | null | null | O1CCOCC1.C(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]-[C:4](-[#7:5])=[O;D1;H0:6]>>[#7:5]-[C:4](=[O;D1;H0:6])-[C:3]-[C:2]-[NH2;D1;+0:1] | 79 | [{"value": 79.0, "product": "Cl.NCCC(=O)NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 17 | HOUR | A 4N HCl solution in dioxane (1 ml) was added to a stirred solution of 3-[(tert-butoxy)carbonylamino]-N-{[2-(2,6-dioxo(3-piperidyl))-1,3-dioxoisoindolin-4-yl]methyl}propanamide (0.5 g, 1.09 mmol) in CH2Cl2 (15 ml) and stirred for 17 hours. The resulting suspension was filtered to give 3-amino-N-{[2-(2,6-dioxo(3-piperid... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccc2c(c1)C[NH]C2.C1CCNCC1 | HO- | O1CCOCC1.C(Cl)Cl | null | 17 | CC(C)(C)OC(=O)NCCC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>O1CCOCC1.C(Cl)Cl>NCCC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2c2972397dd74b20947340ffea064db3 | NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1cccs1>>O=C1CCC(N2C(=O)c3cccc(CNC(=O)c4cccs4)c3C2=O)C(=O)N1 | N12CCCCCC2=NCCC1.Cl.NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.S1C(=CC=C1)C(=O)Cl>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)C=1SC=CC1)=O)=O | [O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([CH2:14][NH2:15])[c:23]3[C:24]2=[O:25])[C:26](=[O:27])[NH:28]1.Cl[C:16](=[O:17])[c:18]1[cH:19][cH:20][cH:21][s:22]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([CH2:14][NH:15][C:16](=[O:17])[... | NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1cccs1 | O=C1CCC(N2C(=O)c3cccc(CNC(=O)c4cccs4)c3C2=O)C(=O)N1 | null | null | CC#N | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CCC(N2C(=O)c3cccc(CNC(=O)c4cccs4)c3C2=O)C(=O)N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#16;a:5]:[c:6].[NH2;D1;+0:7]-[C:8]-[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:7]-[C:8]-[c:9])-[c:3](:[c:4]):[#16;a:5]:[c:6] | 47.6 | [{"value": 47.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)C=1SC=CC1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.6, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)C=1SC=CC1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | 1,8-Diazabicyclo[5,4,0]undec-7-ene (0.620 g, 4.07 mmol) was added to a stirred suspension of 4-(aminomethyl)-2-(2,6-dioxo(3-piperidyl))-isoindoline-1,3-dione hydrochloride (0.600 g, 1.85 mmol) in CH3CN (50 ml). After stirring for 20 min, 2-thiophene-carbonyl chloride (0.3 g, 2.03 mmol) was added. The mixture was stirre... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CCNCC1.c1ccc2c(c1)C[NH]C2.c1ccsc1 | HCl | CC#N | null | 0.333333 | NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1cccs1>CC#N>O=C1CCC(N2C(=O)c3cccc(CNC(=O)c4cccs4)c3C2=O)C(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-82f4ae654ea541028155a1215bf5ab5f | COCC(=O)Cl.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>>COCC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | N12CCCCCC2=NCCC1.Cl.NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.COCC(=O)Cl>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(COC)=O)=O)=O | Cl[C:4]([CH2:3][O:2][CH3:1])=[O:5].[NH2:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[C:14](=[O:15])[N:16]([CH:17]1[CH2:18][CH2:19][C:20](=[O:21])[NH:22][C:23]1=[O:24])[C:25]2=[O:26]>>[CH3:1][O:2][CH2:3][C:4](=[O:5])[NH:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[C:14](=[O:15])[N:16]([CH:17]1[CH2:18][CH2:19][... | COCC(=O)Cl.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | COCC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | null | null | CC#N | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4].[NH2;D1;+0:5]-[C:6]-[c:7]>>[#8:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[C:6]-[c:7] | 66.2 | [{"value": 66.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(COC)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.2, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(COC)=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | 1,8-Diazabicyclo[5,4,0]undec-7-ene (0.62 g, 4.07 mmol) was added to a stirred suspension of 4-(aminomethyl)-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione hydrochloride (0.600 g, 1.85 mmol) in CH3CN (50 ml). After stirring for 20 min, methoxyacetyl chloride (0.22 g, 2.03 mmol) was added. The mixture was stirred at roo... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2c(c1)C[NH]C2.C1CCNCC1 | HCl | CC#N | null | 0.333333 | COCC(=O)Cl.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>CC#N>COCC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4448edeab22e4337aea6e3e98de9815a | CC(=O)OCC(=O)Cl.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>>CC(=O)OCC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | N12CCCCCC2=NCCC1.Cl.NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.C(C)(=O)OCC(=O)Cl>>C(C)(=O)OCC(NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O)=O | Cl[C:6]([CH2:5][O:4][C:2]([CH3:1])=[O:3])=[O:7].[NH2:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][c:14]2[c:15]1[C:16](=[O:17])[N:18]([CH:19]1[CH2:20][CH2:21][C:22](=[O:23])[NH:24][C:25]1=[O:26])[C:27]2=[O:28]>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][C:6](=[O:7])[NH:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][c:14]2[c:15]1[C:16](=[O:17])[N... | CC(=O)OCC(=O)Cl.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | CC(=O)OCC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | null | null | CC#N | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4]-[C:5](-[C;D1;H3:6])=[O;D1;H0:7].[NH2;D1;+0:8]-[C:9]-[c:10]>>[C;D1;H3:6]-[C:5](=[O;D1;H0:7])-[#8:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C:9]-[c:10] | 75.4 | [{"value": 75.0, "product": "C(C)(=O)OCC(NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.4, "product": "C(C)(=O)OCC(NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | 1,8-Diazabicyclo[5,4,0]undec-7-ene (0.62 g, 4.08 mmol) was added to a stirred suspension of 4 (aminomethyl)-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione hydrochloride (0.600 g, 1.85 mmol) in CH3CN (50 ml). After stirring for 20 min, acetoxyacetyl chloride (0.28 g, 2.03 mmol) was added. The mixture was stirred at roo... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2c(c1)C[NH]C2.C1CCNCC1 | HCl | CC#N | null | 0.333333 | CC(=O)OCC(=O)Cl.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>CC#N>CC(=O)OCC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a0126c077178448d93ee3fbac0b69c60 | CCN=C=O.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>>CCNC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | N12CCCCCC2=NCCC1.Cl.NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.C(C)N=C=O>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)NCC)=O)=O | [CH3:1][CH2:2][N:3]=[C:4]=[O:5].[NH2:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[C:14](=[O:15])[N:16]([CH:17]1[CH2:18][CH2:19][C:20](=[O:21])[NH:22][C:23]1=[O:24])[C:25]2=[O:26]>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[C:14](=[O:15])[N:16]([CH:17]1[CH2:18][CH2:19][C:... | CCN=C=O.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | CCNC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | null | null | CC#N | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1 | [C;D1;H3:1]-[C:2]-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;D1;H0:5].[NH2;D1;+0:6]-[C:7]-[c:8]>>[C;D1;H3:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[NH;D2;+0:6]-[C:7]-[c:8] | 30.2 | [{"value": 30.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)NCC)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 30.2, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)NCC)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | 1,8-Diazabicyclo[5,4,0]undec-7-ene (0.29 g, 1.90 mmol) was added to a stirred suspension of 4-(aminomethyl)-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione hydrochloride (0.60 g, 1.85 mmol) in CH3CN (50 ml). After stirring for 20 min, ethyl isocyanate (0.16 g, 2.22 mmol) was added. The mixture was stirred at room tempe... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccc2c(c1)C[NH]C2.C1CCNCC1 | null | CC#N | null | 0.333333 | CCN=C=O.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>CC#N>CCNC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-58baa2c9524442448d310b4a2beaff17 | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=Cc1ccco1>>O=C1CCC(N2C(=O)c3cccc(NCc4ccco4)c3C2=O)C(=O)N1 | NC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.O1C(=CC=C1)C=O.[BH4-].[Na+]>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NCC=1OC=CC1)=O)=O | [O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([NH2:14])[c:21]3[C:22]2=[O:23])[C:24](=[O:25])[NH:26]1.O=[CH:15][c:16]1[cH:17][cH:18][cH:19][o:20]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([NH:14][CH2:15][c:16]4[cH:17][cH:18][cH:19][o:2... | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=Cc1ccco1 | O=C1CCC(N2C(=O)c3cccc(NCc4ccco4)c3C2=O)C(=O)N1 | null | null | C(C)(=O)O | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | O=C1CCC(N2C(=O)c3cccc(NCc4ccco4)c3C2=O)C(=O)N1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#8;a:4]:[c:5].[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[NH2;D1;+0:11]):[c:12]>>[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[NH;D2;+0:11]-[CH2;D2;+0:1]-[c:2](:[c:3]):[#8;a:4]:[c:5]):[c:12] | 35.4 | [{"value": 35.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NCC=1OC=CC1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 35.4, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NCC=1OC=CC1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a suspension of 4-amino-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione (0.55 g, 2 mmol) in acetic acid (20 ml) was added furan-2-carbaldehyde (0.20 g, 2.05 mmol). The mixture was heated to reflux for 5 hours and allowed to cool at room temperature. Sodium borohydride (80 mg, 2 mmol) was added to the reaction mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | C1CCNCC1.c1ccc2c(c1)C[NH]C2.c1ccoc1 | Other | C(C)(=O)O | null | 24 | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=Cc1ccco1>C(C)(=O)O>O=C1CCC(N2C(=O)c3cccc(NCc4ccco4)c3C2=O)C(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c5b66534060c4a5dbcb2412b0b5191e4 | COCC(=O)Cl.Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>>COCC(=O)Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | NC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.COCC(=O)Cl>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(COC)=O)=O)=O | Cl[C:4]([CH2:3][O:2][CH3:1])=[O:5].[NH2:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[C:13](=[O:14])[N:15]([CH:16]1[CH2:17][CH2:18][C:19](=[O:20])[NH:21][C:22]1=[O:23])[C:24]2=[O:25]>>[CH3:1][O:2][CH2:3][C:4](=[O:5])[NH:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[C:13](=[O:14])[N:15]([CH:16]1[CH2:17][CH2:18][C:19](=[O:20])[N... | COCC(=O)Cl.Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | COCC(=O)Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | null | null | C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4].[#7:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](-[NH2;D1;+0:10]):[c:11]>>[#7:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4]):[c:11] | 100 | [{"value": 100.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(COC)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.9, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(COC)=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 4-amino-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione (0.55 g, 2.0 mmol) in THF (30 ml) was added 2-methoxyacetyl chloride (0.43 g, 4.0 mmol). The stirred mixture was heated to reflux for 18 hours. The solvent was evaporated in vacuo and the resulting solid was slurried in diethyl ether (20 ml) and... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2c(c1)C[NH]C2.C1CCNCC1 | HCl | C1CCOC1 | null | null | COCC(=O)Cl.Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>C1CCOC1>COCC(=O)Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dd8a4917244d4dcb87fd3a09f7165ef6 | CCCCCCC(=O)Cl.Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>>CCCCCCC(=O)Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | NC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.C(CCCCCC)(=O)Cl>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(CCCCCC)=O)=O)=O | Cl[C:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:8].[NH2:9][c:10]1[cH:11][cH:12][cH:13][c:14]2[c:15]1[C:16](=[O:17])[N:18]([CH:19]1[CH2:20][CH2:21][C:22](=[O:23])[NH:24][C:25]1=[O:26])[C:27]2=[O:28]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7](=[O:8])[NH:9][c:10]1[cH:11][cH:12][cH:13][c:14]2[c:15]1[C:16](=[O:... | CCCCCCC(=O)Cl.Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | CCCCCCC(=O)Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | null | null | C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[#7:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](-[NH2;D1;+0:10]):[c:11]>>[#7:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]):[c:11] | 79.1 | [{"value": 79.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(CCCCCC)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.1, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(CCCCCC)=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred suspension of 4-amino-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione (0.55 g, 2.0 mmol) in THF (30 ml) was added heptanoyl chloride (0.59 g, 4.0 mmol). The mixture was heated to reflux for 18 hours. The solvent was evaporated in vacuo and the resulting solid was slurried in diethyl ether (20 ml) and filte... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2c(c1)C[NH]C2.C1CCNCC1 | HCl | C1CCOC1 | null | null | CCCCCCC(=O)Cl.Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>C1CCOC1>CCCCCCC(=O)Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c232326fe2bb4f1a9b4292d391209dba | CC(=O)OCC(=O)Cl.Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>>CC(=O)OCC(=O)Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | NC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.C(C)(=O)OCC(=O)Cl>>C(C)(=O)OCC(NC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O)=O | Cl[C:6]([CH2:5][O:4][C:2]([CH3:1])=[O:3])=[O:7].[NH2:8][c:9]1[cH:10][cH:11][cH:12][c:13]2[c:14]1[C:15](=[O:16])[N:17]([CH:18]1[CH2:19][CH2:20][C:21](=[O:22])[NH:23][C:24]1=[O:25])[C:26]2=[O:27]>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][cH:11][cH:12][c:13]2[c:14]1[C:15](=[O:16])[N:17]([CH:18]1[CH... | CC(=O)OCC(=O)Cl.Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | CC(=O)OCC(=O)Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | null | null | C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4]-[C:5](-[C;D1;H3:6])=[O;D1;H0:7].[#7:8]-[C:9](=[O;D1;H0:10])-[c:11]:[c:12](-[NH2;D1;+0:13]):[c:14]>>[#7:8]-[C:9](=[O;D1;H0:10])-[c:11]:[c:12](-[NH;D2;+0:13]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4]-[C:5](-[C;D1;H3:6])=[O;D1;H0:7]):[c:14] | 75 | [{"value": 75.0, "product": "C(C)(=O)OCC(NC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.0, "product": "C(C)(=O)OCC(NC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred suspension of 4-amino-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione (0.55 g, 2.0 mmol) in THF (30 ml) was added (chlorocarbonyl)methyl acetate (0.55 g, 4.0 mmol). The mixture was heated to reflux for 18 hours. The solvent was evaporated in vacuo and the resulting solid was slurried in diethyl ether (20 m... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2c(c1)C[NH]C2.C1CCNCC1 | HCl | C1CCOC1 | null | null | CC(=O)OCC(=O)Cl.Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>C1CCOC1>CC(=O)OCC(=O)Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1ce0864ffcad4e2cbfb587b30c655866 | CCCCC(=O)Cl.Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>>CCCCC(=O)Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | NC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.C(CCCC)(=O)Cl>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(CCCC)=O)=O)=O | Cl[C:5]([CH2:4][CH2:3][CH2:2][CH3:1])=[O:6].[NH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[C:14](=[O:15])[N:16]([CH:17]1[CH2:18][CH2:19][C:20](=[O:21])[NH:22][C:23]1=[O:24])[C:25]2=[O:26]>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5](=[O:6])[NH:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[C:14](=[O:15])[N:16]([CH:17]1[CH2:18][CH2:... | CCCCC(=O)Cl.Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | CCCCC(=O)Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | null | null | C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[#7:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](-[NH2;D1;+0:10]):[c:11]>>[#7:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]):[c:11] | 85.3 | [{"value": 85.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(CCCC)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.3, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(CCCC)=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred suspension of 4-amino-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione (0.55 g, 2.0 mmol) in THF (30 ml) was added pentanoyl chloride (0.48 g, 4.0 mmol). The stirred mixture was heated to reflux for 18 hours. The solvent was evaporated in vacuo and the resulting solid was slurried in diethyl ether (20 ml) a... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2c(c1)C[NH]C2.C1CCNCC1 | HCl | C1CCOC1 | null | null | CCCCC(=O)Cl.Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>C1CCOC1>CCCCC(=O)Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bfb278c2801e4c8a8008f8823ebf19cd | COC(=O)C(=O)Cl.Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>>COC(=O)C(=O)Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | NC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.ClC(=O)C(=O)OC>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(=O)C(=O)OC)=O)=O | Cl[C:5]([C:3]([O:2][CH3:1])=[O:4])=[O:6].[NH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[C:14](=[O:15])[N:16]([CH:17]1[CH2:18][CH2:19][C:20](=[O:21])[NH:22][C:23]1=[O:24])[C:25]2=[O:26]>>[CH3:1][O:2][C:3](=[O:4])[C:5](=[O:6])[NH:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[C:14](=[O:15])[N:16]([CH:17]1[CH2:18][CH2:19][C:... | COC(=O)C(=O)Cl.Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | COC(=O)C(=O)Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | null | null | C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | a0f509c51b80cfca9aa6355468af6f3d901b4a3653602f32ee5994157ced49f8 | 41a2c91a94881e86389ce33bb44cfd1f3b3dc1b8c84cd64ddc8a356ca8fd86c3 | O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6].[#7:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[#7:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11](-[NH;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6]):[c:13] | 76.5 | [{"value": 76.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(=O)C(=O)OC)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.5, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(=O)C(=O)OC)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred suspension of 4-amino-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione (0.55 g, 2.0 mmol) in THF (30 ml) was added methyl (chlorocarbonyl)formate (0.49 g, 4.0 mmol). The mixture was heated to reflux for 18 hours. The solvent was evaporated in vacuo and the resulting solid was slurried in diethyl ether (20 m... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ester.Primary amine | Ester.Secondary amide | null | null | c1ccc2c(c1)C[NH]C2.C1CCNCC1 | HCl | C1CCOC1 | null | null | COC(=O)C(=O)Cl.Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>C1CCOC1>COC(=O)C(=O)Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c4c2a9718c004782a0127d022f6fdc03 | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1ccco1>>O=C1CCC(N2C(=O)c3cccc(NC(=O)c4ccco4)c3C2=O)C(=O)N1 | NC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.O1C(=CC=C1)C(=O)Cl.O1C(=CC=C1)C(=O)Cl>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(=O)C=1OC=CC1)=O)=O | [O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([NH2:14])[c:22]3[C:23]2=[O:24])[C:25](=[O:26])[NH:27]1.Cl[C:15](=[O:16])[c:17]1[cH:18][cH:19][cH:20][o:21]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([NH:14][C:15](=[O:16])[c:17]4[cH:18][cH... | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1ccco1 | O=C1CCC(N2C(=O)c3cccc(NC(=O)c4ccco4)c3C2=O)C(=O)N1 | null | null | C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CCC(N2C(=O)c3cccc(NC(=O)c4ccco4)c3C2=O)C(=O)N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6].[#7:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[#7:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11](-[NH;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6]):[c:13] | 88.5 | [{"value": 88.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(=O)C=1OC=CC1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.5, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(=O)C=1OC=CC1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred suspension of 4-amino-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione (0.55 g, 2.0 mmol) in THF (30 ml) was added furan-2-carbonyl chloride (0.52 g, 4.0 mmol). The mixture was heated to reflux for 18 hours. To the reaction mixture was added additional furan-2-carbonyl chloride (0.26 g, 2 mmol). The mixture... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CCNCC1.c1ccc2c(c1)C[NH]C2.c1ccoc1 | HCl | C1CCOC1 | null | null | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1ccco1>C1CCOC1>O=C1CCC(N2C(=O)c3cccc(NC(=O)c4ccco4)c3C2=O)C(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2bf12c641a524d1c8aaf496af206b419 | CCC(=O)Cl.Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>>CCC(=O)Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | NC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.C(CC)(=O)Cl>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(CC)=O)=O)=O | Cl[C:3]([CH2:2][CH3:1])=[O:4].[NH2:5][c:6]1[cH:7][cH:8][cH:9][c:10]2[c:11]1[C:12](=[O:13])[N:14]([CH:15]1[CH2:16][CH2:17][C:18](=[O:19])[NH:20][C:21]1=[O:22])[C:23]2=[O:24]>>[CH3:1][CH2:2][C:3](=[O:4])[NH:5][c:6]1[cH:7][cH:8][cH:9][c:10]2[c:11]1[C:12](=[O:13])[N:14]([CH:15]1[CH2:16][CH2:17][C:18](=[O:19])[NH:20][C:21]1... | CCC(=O)Cl.Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | CCC(=O)Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | null | null | C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C;D1;H3:4].[#7:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](-[NH2;D1;+0:10]):[c:11]>>[#7:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C;D1;H3:4]):[c:11] | 88.1 | [{"value": 88.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(CC)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.1, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(CC)=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred suspension of 4-amino-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione (0.55 g, 2.0 mmol) in THF (30 ml) was added propanoyl chloride (0.37 g, 4.0 mmol). The mixture was heated to reflux for 18 hours. The solvent was evaporated in vacuo and the resulting solid was slurried in diethyl ether (20 ml) and filte... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2c(c1)C[NH]C2.C1CCNCC1 | HCl | C1CCOC1 | null | null | CCC(=O)Cl.Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>C1CCOC1>CCC(=O)Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1e5ef2248ecb4a34aff79c6643c75f4d | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)Cc1ccccc1>>O=C1CCC(N2C(=O)c3cccc(NC(=O)Cc4ccccc4)c3C2=O)C(=O)N1 | NC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.C1(=CC=CC=C1)CC(=O)Cl>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(CC1=CC=CC=C1)=O)=O)=O | [O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([NH2:14])[c:24]3[C:25]2=[O:26])[C:27](=[O:28])[NH:29]1.Cl[C:15](=[O:16])[CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([NH:14][C:15](=[O:16])[... | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)Cc1ccccc1 | O=C1CCC(N2C(=O)c3cccc(NC(=O)Cc4ccccc4)c3C2=O)C(=O)N1 | null | null | C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CCC(N2C(=O)c3cccc(NC(=O)Cc4ccccc4)c3C2=O)C(=O)N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[#7:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](-[NH2;D1;+0:10]):[c:11]>>[#7:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4]):[c:11] | 92 | [{"value": 92.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(CC1=CC=CC=C1)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(CC1=CC=CC=C1)=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred suspension of 4-amino-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione (0.55 g, 2.0 mmol) in THF (30 ml) was added 2-phenylacetyl chloride (0.62 g, 4.0 mmol). The mixture was heated to reflux for 18 hours. The solvent was evaporated in vacuo and the resulting solid was slurried in diethyl ether (20 ml) and ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CCNCC1.c1ccc2c(c1)C[NH]C2.c1ccccc1 | HCl | C1CCOC1 | null | null | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)Cc1ccccc1>C1CCOC1>O=C1CCC(N2C(=O)c3cccc(NC(=O)Cc4ccccc4)c3C2=O)C(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d822c32b9a464179a547a083f2e4697e | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1ccccn1>>O=C1CCC(N2C(=O)c3cccc(NC(=O)c4ccccn4)c3C2=O)C(=O)N1 | NC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.Cl.N1=C(C=CC=C1)C(=O)Cl>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(=O)C1=NC=CC=C1)=O)=O | [O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([NH2:14])[c:23]3[C:24]2=[O:25])[C:26](=[O:27])[NH:28]1.Cl[C:15](=[O:16])[c:17]1[cH:18][cH:19][cH:20][cH:21][n:22]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([NH:14][C:15](=[O:16])[c:17]4[cH... | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1ccccn1 | O=C1CCC(N2C(=O)c3cccc(NC(=O)c4ccccn4)c3C2=O)C(=O)N1 | null | null | CO.C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CCC(N2C(=O)c3cccc(NC(=O)c4ccccn4)c3C2=O)C(=O)N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[#7:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[#7:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11](-[NH;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6]):[c:13] | 40 | [{"value": 40.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(=O)C1=NC=CC=C1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 39.6, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(=O)C1=NC=CC=C1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred suspension of 4-amino-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione (0.55 g, 2.0 mmol) in THF (30 ml) was added pyridine-2-carbonyl chloride hydrochloride (0.71 g, 4.0 mmol). The mixture was heated to reflux for 18 hours. The solvent was evaporated in vacuo and the resulting solid was slurried in a bipha... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CCNCC1.c1ccc2c(c1)C[NH]C2.c1ccncc1 | HCl | CO.C1CCOC1 | null | null | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1ccccn1>CO.C1CCOC1>O=C1CCC(N2C(=O)c3cccc(NC(=O)c4ccccn4)c3C2=O)C(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5ff41231fe2d4459a579918e68254db6 | O=C1CCC(N2C(=O)c3cccc(NC(=O)CCl)c3C2=O)C(=O)N1.[N-]=[N+]=[N-]>>[N-]=[N+]=NCC(=O)Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(CCl)=O)=O)=O.[N-]=[N+]=[N-].[Na+]>>N(=[N+]=[N-])CC(=O)NC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O | Cl[CH2:4][C:5](=[O:6])[NH:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[C:14](=[O:15])[N:16]([CH:17]1[CH2:18][CH2:19][C:20](=[O:21])[NH:22][C:23]1=[O:24])[C:25]2=[O:26].[N-:1]=[N+:2]=[N-:3]>>[N-:1]=[N+:2]=[N:3][CH2:4][C:5](=[O:6])[NH:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[C:14](=[O:15])[N:16]([CH:17]1[CH2:18][CH2:19][... | O=C1CCC(N2C(=O)c3cccc(NC(=O)CCl)c3C2=O)C(=O)N1.[N-]=[N+]=[N-] | [N-]=[N+]=NCC(=O)Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 4b07a4c2a14d792a37e78a751619e60b15c60cbff0bebae1109754fb52d84cbb | 2d41632f7225d65cdc2ad8562dfb28f3f5a017f92040ed4ccafbb8154954c8fe | O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1 | Cl-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5].[N-;H0;D1:6]=[#7;+:7]=[N;-;D1;H0:8]>>[N;-;D1;H0:8]=[#7;+:7]=[N;H0;D2;+0:6]-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5] | 96 | [{"value": 96.0, "product": "N(=[N+]=[N-])CC(=O)NC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.0, "product": "N(=[N+]=[N-])CC(=O)NC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of N-[2-(2,6-dioxo(3-piperidyl))-1,3-dioxoisoindolin-4-yl]-2-chloroacetamide (1.53 g, 4.4 mmol) in acetone (30 ml) was added sodium azide (0.43 g, 6.6 mmol). The mixture was heated to reflux for 18 hours. The solvent was evaporated in vacuo to give 1.49 g (96%) of product as an off-white solid: 1H NMR (... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Azide | null | null | c1ccc2c(c1)C[NH]C2.C1CCNCC1 | Other | CC(=O)C | null | null | O=C1CCC(N2C(=O)c3cccc(NC(=O)CCl)c3C2=O)C(=O)N1.[N-]=[N+]=[N-]>CC(=O)C>[N-]=[N+]=NCC(=O)Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a4f9337976ae45f9bec978eb4a733a99 | Nc1cccc2c1CN(C1CCC(=O)NC1=O)C2=O.O=C(Cl)CCl>>O=C1CCC(N2Cc3c(NC(=O)CCl)cccc3C2=O)C(=O)N1 | NC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O.ClCC(=O)Cl>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1)NC(CCl)=O)=O)=O | [O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[CH2:7][c:8]3[c:9]([NH2:10])[cH:15][cH:16][cH:17][c:18]3[C:19]2=[O:20])[C:21](=[O:22])[NH:23]1.Cl[C:11](=[O:12])[CH2:13][Cl:14]>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[CH2:7][c:8]3[c:9]([NH:10][C:11](=[O:12])[CH2:13][Cl:14])[cH:15][cH:16][cH:17][c:18]3[C:19]2=[O:20])[C:21](=[O:22... | Nc1cccc2c1CN(C1CCC(=O)NC1=O)C2=O.O=C(Cl)CCl | O=C1CCC(N2Cc3c(NC(=O)CCl)cccc3C2=O)C(=O)N1 | null | ClCC(=O)Cl | C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CCC(N2Cc3ccccc3C2=O)C(=O)N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Cl;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[Cl;D1;H0:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 92.1 | [{"value": 92.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1)NC(CCl)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.1, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1)NC(CCl)=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred suspension of 3-(4-amino-1-oxoisoindolin-2-yl)piperidine-2,6-dione (3.89 g, 15.0 mmol) in THF (50 ml) was added chloroacetyl chloride (1.86 g, 16.5 mmol). The mixture was heated to reflux for 45 minutes. To the reaction mixture was added additional chloroacetyl chloride (0.15 g, 0.13 mmol). The reaction mi... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CCNCC1.c1ccc2c(c1)C[NH]C2 | HCl | ClCC(=O)Cl.C1CCOC1 | null | null | Nc1cccc2c1CN(C1CCC(=O)NC1=O)C2=O.O=C(Cl)CCl>ClCC(=O)Cl.C1CCOC1>O=C1CCC(N2Cc3c(NC(=O)CCl)cccc3C2=O)C(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-432839de2b464e6a9c0b3a86be259370 | O=C1CCC(N2Cc3c(NC(=O)CCl)cccc3C2=O)C(=O)N1.[N-]=[N+]=[N-]>>[N-]=[N+]=NCC(=O)Nc1cccc2c1CN(C1CCC(=O)NC1=O)C2=O | [N-]=[N+]=[N-].[Na+].O=C1NC(CCC1N1C(C2=CC=CC(=C2C1)NC(CCl)=O)=O)=O.[Na+].[I-].[N-]=[N+]=[N-].[Na+]>>N(=[N+]=[N-])CC(=O)NC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O | Cl[CH2:4][C:5](=[O:6])[NH:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[CH2:14][N:15]([CH:16]1[CH2:17][CH2:18][C:19](=[O:20])[NH:21][C:22]1=[O:23])[C:24]2=[O:25].[N-:1]=[N+:2]=[N-:3]>>[N-:1]=[N+:2]=[N:3][CH2:4][C:5](=[O:6])[NH:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[CH2:14][N:15]([CH:16]1[CH2:17][CH2:18][C:19](=[O:20])... | O=C1CCC(N2Cc3c(NC(=O)CCl)cccc3C2=O)C(=O)N1.[N-]=[N+]=[N-] | [N-]=[N+]=NCC(=O)Nc1cccc2c1CN(C1CCC(=O)NC1=O)C2=O | null | null | ClCCl.CC(=O)C.O | Heteroatom Alkylation and Arylation | OtherReaction | 4b07a4c2a14d792a37e78a751619e60b15c60cbff0bebae1109754fb52d84cbb | 2d41632f7225d65cdc2ad8562dfb28f3f5a017f92040ed4ccafbb8154954c8fe | O=C1CCC(N2Cc3ccccc3C2=O)C(=O)N1 | Cl-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5].[N-;H0;D1:6]=[#7;+:7]=[N;-;D1;H0:8]>>[N;-;D1;H0:8]=[#7;+:7]=[N;H0;D2;+0:6]-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5] | 93 | [{"value": 93.0, "product": "N(=[N+]=[N-])CC(=O)NC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.9, "product": "N(=[N+]=[N-])CC(=O)NC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To a stirred suspension of N-[2-(2,6-dioxo(3-piperidyl))-1-oxoisoindolin-4-yl]-2-chloroacetamide (4.64 g, 13.8 mmol) in acetone (60 ml) was added sodium azide (1.35 g, 20.7 mmol). The mixture was heated to reflux for 18 hours. After 18 hours, to the reaction mixture was added NaI (2.05 g, 13.8 mmol) and additional sodi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Azide | null | null | c1ccc2c(c1)C[NH]C2.C1CCNCC1 | Other | ClCCl.CC(=O)C.O | null | 18 | O=C1CCC(N2Cc3c(NC(=O)CCl)cccc3C2=O)C(=O)N1.[N-]=[N+]=[N-]>ClCCl.CC(=O)C.O>[N-]=[N+]=NCC(=O)Nc1cccc2c1CN(C1CCC(=O)NC1=O)C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c63de44fa6154cee858aafdb79d6b6e4 | Nc1cccc2c1CN(C1CCC(=O)NC1=O)C2=O.O=Cc1ccco1>>O=C1CCC(N2Cc3c(NCc4ccco4)cccc3C2=O)C(=O)N1 | NC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O.O1C(=CC=C1)C=O.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>O1C(=CC=C1)CNC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O | [O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[CH2:7][c:8]3[c:9]([NH2:10])[cH:17][cH:18][cH:19][c:20]3[C:21]2=[O:22])[C:23](=[O:24])[NH:25]1.O=[CH:11][c:12]1[cH:13][cH:14][cH:15][o:16]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[CH2:7][c:8]3[c:9]([NH:10][CH2:11][c:12]4[cH:13][cH:14][cH:15][o:16]4)[cH:17][cH:18][cH:19][c:20]3[C:... | Nc1cccc2c1CN(C1CCC(=O)NC1=O)C2=O.O=Cc1ccco1 | O=C1CCC(N2Cc3c(NCc4ccco4)cccc3C2=O)C(=O)N1 | null | null | CO | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | O=C1CCC(N2Cc3c(NCc4ccco4)cccc3C2=O)C(=O)N1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#8;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#8;a:4]:[c:5] | 29.5 | [{"value": 29.5, "product": "O1C(=CC=C1)CNC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a stirred suspension of 3-(4-amino-1-oxoisoindolin-2-yl)piperidine-2,6-dione (0.52 g, 2.0 mmol) in methanol (50 ml) was added furan-2-carbaldehyde (0.200 g, 2.05 mmol). The mixture was heated to reflux for 4 hours. The solvent was evaporated in vacuo and the residue was dissolved in acetic acid (20 ml). Sodium triac... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | C1CCNCC1.c1ccoc1.c1ccc2c(c1)C[NH]C2 | Other | CO | null | 24 | Nc1cccc2c1CN(C1CCC(=O)NC1=O)C2=O.O=Cc1ccco1>CO>O=C1CCC(N2Cc3c(NCc4ccco4)cccc3C2=O)C(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-85144f34d979457fac13774a460cb8d8 | CCCCC=O.Nc1cccc2c1CN(C1CCC(=O)NC1=O)C2=O>>CCCCCNc1cccc2c1CN(C1CCC(=O)NC1=O)C2=O | NC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O.C(CCCC)=O.C(C)(=O)O.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>O=C1N(CC2=C(C=CC=C12)NCCCCC)C1C(NC(CC1)=O)=O | O=[CH:5][CH2:4][CH2:3][CH2:2][CH3:1].[NH2:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[CH2:13][N:14]([CH:15]1[CH2:16][CH2:17][C:18](=[O:19])[NH:20][C:21]1=[O:22])[C:23]2=[O:24]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[CH2:13][N:14]([CH:15]1[CH2:16][CH2:17][C:18](=[O:19])[NH:20][C:2... | CCCCC=O.Nc1cccc2c1CN(C1CCC(=O)NC1=O)C2=O | CCCCCNc1cccc2c1CN(C1CCC(=O)NC1=O)C2=O | null | null | C(C)(=O)OCC.CN(C)C=O | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | O=C1CCC(N2Cc3ccccc3C2=O)C(=O)N1 | O=[CH;D2;+0:1]-[C:2]-[C:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 21.3 | [{"value": 21.0, "product": "O=C1N(CC2=C(C=CC=C12)NCCCCC)C1C(NC(CC1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 21.3, "product": "O=C1N(CC2=C(C=CC=C12)NCCCCC)C1C(NC(CC1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | To a stirred solution of 3-(4-amino-1-oxoisoindolin-2-yl)piperidine-2,6-dione (0.52 g, 2.0 mmol) in DMF (10 ml) was added pentanal (0.26 g, 3.0 mmol), acetic acid (0.24 g, 4.0 mmol), and sodium triactoxyborohydride (0.85 g, 4.0 mmol). The reaction mixture was stirred at room temperature for 6 hours. The solvent was eva... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccc2c(c1)C[NH]C2.C1CCNCC1 | Other | C(C)(=O)OCC.CN(C)C=O | null | 6 | CCCCC=O.Nc1cccc2c1CN(C1CCC(=O)NC1=O)C2=O>C(C)(=O)OCC.CN(C)C=O>CCCCCNc1cccc2c1CN(C1CCC(=O)NC1=O)C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-78a7aadfffad488f91c3c3e08b37dccb | COC(=O)c1cccc(N)c1C(=O)OC.COCCO>>COCCNc1cccc(C(=O)OC)c1C(=O)OC | COC(C=1C(C(=O)OC)=C(C=CC1)N)=O.C(C)(=O)O.C(C(=O)Cl)(=O)Cl.CS(=O)C.C(C)N(CC)CC.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+].COCCO>>COC(C=1C(C(=O)OC)=C(C=CC1)NCCOC)=O | [NH2:5][c:6]1[cH:7][cH:8][cH:9][c:10]([C:11](=[O:12])[O:13][CH3:14])[c:15]1[C:16](=[O:17])[O:18][CH3:19].O[CH2:4][CH2:3][O:2][CH3:1]>>[CH3:1][O:2][CH2:3][CH2:4][NH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([C:11](=[O:12])[O:13][CH3:14])[c:15]1[C:16](=[O:17])[O:18][CH3:19] | COC(=O)c1cccc(N)c1C(=O)OC.COCCO | COCCNc1cccc(C(=O)OC)c1C(=O)OC | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | 80c5fffb5a6cd9bcf0b3d20ee51fe5f6574f02d4cb5ea6a4d33b4a9098b0e672 | 405fc0d288d595940df82750271ed5f4125713ca8b676b8ed83063765fec7c50 | c1ccccc1 | O-[CH2;D2;+0:1]-[C:2]-[#8:3].[#8:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[NH2;D1;+0:9]):[c:10]>>[#8:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[NH;D2;+0:9]-[CH2;D2;+0:1]-[C:2]-[#8:3]):[c:10] | 84 | [{"value": 84.0, "product": "COC(C=1C(C(=O)OC)=C(C=CC1)NCCOC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.8, "product": "COC(C=1C(C(=O)OC)=C(C=CC1)NCCOC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | To a stirred solution of oxalyl chloride (1.75 ml, 20 mmol) in methylene chloride (20 ml) under a nitrogen atmosphere at −78° C. was added DMSO (1.42 ml, 20 mmol) in methylene chloride (10 ml) dropwise over 5 minutes. The mixture was stirred for 5 minutes followed by the dropwise addition of 2-methoxyethanol (1.58 ml, ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Primary amine | Secondary amine | null | null | c1ccccc1 | HO- | C(Cl)Cl | null | 0.083333 | COC(=O)c1cccc(N)c1C(=O)OC.COCCO>C(Cl)Cl>COCCNc1cccc(C(=O)OC)c1C(=O)OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4f545cbd274e45a1bffdf54ae55b0fee | COCCNc1cccc(C(=O)OC)c1C(=O)OC>>COCCNc1cccc(C(=O)O)c1C(=O)O | COC(C=1C(C(=O)OC)=C(C=CC1)NCCOC)=O.[OH-].[K+]>>COCCNC1=C(C(C(=O)O)=CC=C1)C(=O)O | C[O:13][C:11]([c:10]1[cH:9][cH:8][cH:7][c:6]([NH:5][CH2:4][CH2:3][O:2][CH3:1])[c:14]1[C:15](=[O:16])[O:17]C)=[O:12]>>[CH3:1][O:2][CH2:3][CH2:4][NH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([C:11](=[O:12])[OH:13])[c:14]1[C:15](=[O:16])[OH:17] | COCCNc1cccc(C(=O)OC)c1C(=O)OC | COCCNc1cccc(C(=O)O)c1C(=O)O | null | null | CO | Deprotection | OtherReaction | 6e62db7aac546f574bcfb83067ba8906c30fcbfedfc37aa16b5eaad33833f45a | ed5fed81ba501ef41c88831ec6b9463b899bfdd0815c4145ae51c79addb226d0 | c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4]:[c:5]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8] | null | [] | null | null | 8 | HOUR | To a stirred solution of 3-(2-methoxy-ethylamino)-phthalic acid dimethyl ester (2.24 g, 8.38 mmol) in methanol (50 ml) was added 5N potassium hydroxide (10 ml). The mixture was stirred at room temperature overnight. The solvent was evaporated in vacuo and the residue dissolved in water (50 ml). The water was washed wit... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Carboxylic acid.Carboxylic acid | null | null | c1ccccc1 | Other | CO | null | 8 | COCCNc1cccc(C(=O)OC)c1C(=O)OC>CO>COCCNc1cccc(C(=O)O)c1C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-92144a870eff4e91b4fc3206bd4fc14e | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)COCc1ccccc1>>O=C1CCC(N2C(=O)c3cccc(NC(=O)COCc4ccccc4)c3C2=O)C(=O)N1 | NC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.C(C1=CC=CC=C1)OCC(=O)Cl.CO>>C(C1=CC=CC=C1)OCC(=O)NC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O | [O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([NH2:14])[c:26]3[C:27]2=[O:28])[C:29](=[O:30])[NH:31]1.Cl[C:15](=[O:16])[CH2:17][O:18][CH2:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([NH:14][C... | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)COCc1ccccc1 | O=C1CCC(N2C(=O)c3cccc(NC(=O)COCc4ccccc4)c3C2=O)C(=O)N1 | null | null | C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CCC(N2C(=O)c3cccc(NC(=O)COCc4ccccc4)c3C2=O)C(=O)N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4].[#7:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](-[NH2;D1;+0:10]):[c:11]>>[#7:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4]):[c:11] | 80.1 | [{"value": 80.0, "product": "C(C1=CC=CC=C1)OCC(=O)NC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.1, "product": "C(C1=CC=CC=C1)OCC(=O)NC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a suspension of 4-amino-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione (1.10 g, 4 mmol) in THF (30 ml) was added benzyloxyacetyl chloride (1.26 ml, 8 mmol). The mixture was heated to reflux for 18 hours. The reaction was cooled to room temperature, methanol (2 ml) was added, and the mixture stirred for 1 hour. The ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CCNCC1.c1ccc2c(c1)C[NH]C2.c1ccccc1 | HCl | C1CCOC1 | null | 1 | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)COCc1ccccc1>C1CCOC1>O=C1CCC(N2C(=O)c3cccc(NC(=O)COCc4ccccc4)c3C2=O)C(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-438d6a99b9ef41de83c883a76ce3a643 | CCCCC=O.COC(=O)c1cccc(N)c1C(=O)OC>>CCCCCNc1cccc(C(=O)OC)c1C(=O)OC | C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+].COC(C=1C(C(=O)OC)=C(C=CC1)N)=O.C(CCCC)=O.C(C)(=O)O>>COC(C=1C(C(=O)OC)=C(C=CC1)NCCCCC)=O | O=[CH:5][CH2:4][CH2:3][CH2:2][CH3:1].[NH2:6][c:7]1[cH:8][cH:9][cH:10][c:11]([C:12](=[O:13])[O:14][CH3:15])[c:16]1[C:17](=[O:18])[O:19][CH3:20]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][c:7]1[cH:8][cH:9][cH:10][c:11]([C:12](=[O:13])[O:14][CH3:15])[c:16]1[C:17](=[O:18])[O:19][CH3:20] | CCCCC=O.COC(=O)c1cccc(N)c1C(=O)OC | CCCCCNc1cccc(C(=O)OC)c1C(=O)OC | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccccc1 | O=[CH;D2;+0:1]-[C:2]-[C:3].[#8:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[NH2;D1;+0:9]):[c:10]>>[#8:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[NH;D2;+0:9]-[CH2;D2;+0:1]-[C:2]-[C:3]):[c:10] | 100 | [{"value": 100.0, "product": "COC(C=1C(C(=O)OC)=C(C=CC1)NCCCCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.0, "product": "COC(C=1C(C(=O)OC)=C(C=CC1)NCCCCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | To a stirred solution of 3-amino-phthalic acid dimethyl ester (3.14 g, 15 mmol) in methylene chloride (50 ml) under a nitrogen atmosphere were added valeraldehyde (2.0 ml, 18.75 mmol) and acetic acid (5.18 ml, 90 mmol). The mixture was stirred for 5 minutes followed by addition of sodium triacetoxyborohydride (6.36 g, ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1 | Other | C(Cl)Cl | null | 0.083333 | CCCCC=O.COC(=O)c1cccc(N)c1C(=O)OC>C(Cl)Cl>CCCCCNc1cccc(C(=O)OC)c1C(=O)OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f654844fae56457faa780aa881ef1d17 | CCCCCNc1cccc(C(=O)OC)c1C(=O)OC>>CCCCCNc1cccc(C(=O)O)c1C(=O)O | COC(C=1C(C(=O)OC)=C(C=CC1)NCCCCC)=O.COCCNC1=C(C(C(=O)O)=CC=C1)C(=O)O>>C(CCCC)NC1=C(C(C(=O)O)=CC=C1)C(=O)O | C[O:14][C:12]([c:11]1[cH:10][cH:9][cH:8][c:7]([NH:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:15]1[C:16](=[O:17])[O:18]C)=[O:13]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][c:7]1[cH:8][cH:9][cH:10][c:11]([C:12](=[O:13])[OH:14])[c:15]1[C:16](=[O:17])[OH:18] | CCCCCNc1cccc(C(=O)OC)c1C(=O)OC | CCCCCNc1cccc(C(=O)O)c1C(=O)O | null | null | null | Deprotection | OtherReaction | 6e62db7aac546f574bcfb83067ba8906c30fcbfedfc37aa16b5eaad33833f45a | ed5fed81ba501ef41c88831ec6b9463b899bfdd0815c4145ae51c79addb226d0 | c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4]:[c:5]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8] | null | [] | null | null | null | null | 3-Pentylamino-phthalic acid dimethyl ester (4.19, 15 mmol) was treated in the same manner as described above for the synthesis of 3-(2-methoxy-ethylamino)-phthalic acid. The product of the reaction, which contained a mixture of diacid and monomethyl esters, was used without further purification.
Conditions: See reactio... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Carboxylic acid.Carboxylic acid | null | null | c1ccccc1 | Other | null | null | null | CCCCCNc1cccc(C(=O)OC)c1C(=O)OC>>CCCCCNc1cccc(C(=O)O)c1C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7a35a5908175421aac37278eea689741 | CCCCCNc1cccc(C(=O)O)c1C(=O)O.NC1CCC(=O)NC1=O>>CCCCCNc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | C(CCCC)NC1=C(C(C(=O)O)=CC=C1)C(=O)O.Cl.NC1C(NC(CC1)=O)=O>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NCCCCC)=O)=O | O[C:13]([c:12]1[c:7]([NH:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[cH:8][cH:9][cH:10][c:11]1[C:24](O)=[O:25])=[O:14].[NH2:15][CH:16]1[CH2:17][CH2:18][C:19](=[O:20])[NH:21][C:22]1=[O:23]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[C:13](=[O:14])[N:15]([CH:16]1[CH2:17][CH2:18][C:19](=[O... | CCCCCNc1cccc(C(=O)O)c1C(=O)O.NC1CCC(=O)NC1=O | CCCCCNc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | null | null | C(C)(=O)O | Acylation | OtherReaction | 03989296fe7fd00d3061010c1aadbbfb4b9eaa9ca91856790fffb1e1bf4b4c50 | b7eb222f11e89f2ccff57aab9a5106ae4173f0ba94ac518e1a9f3b22a378531d | O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[C;H0;D3;+0:6](-O)=[O;D1;H0:7]):[c:8].[C:9]-[C:10](-[NH2;D1;+0:11])-[C:12](=[O;D1;H0:13])-[#7:14]-[C:15]=[O;D1;H0:16]>>[C:9]-[C:10](-[N;H0;D3;+0:11]1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](:[c:8])-[C;H0;D3;+0:6]-1=[O;D1;H0:7])-[C:12](=[O;D1;H0:13])-[#7:14]-[... | 53 | [{"value": 53.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NCCCCC)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NCCCCC)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred solution of 3-pentylamino-phthalic acid (2.51 g, 10 mmol) in acetic acid (50 ml) was added 3-amino-piperidine-2,6-dione hydrochloride (1.81 g, 11 mmol). The reaction mixture was heated to reflux overnight. The solvent was evaporated in vacuo and the residue dissolved in ethyl acetate (100 ml). The ethyl ac... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Primary amine | Substituted dicarboximide | null | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1CCNCC1 | HO- | C(C)(=O)O | null | null | CCCCCNc1cccc(C(=O)O)c1C(=O)O.NC1CCC(=O)NC1=O>C(C)(=O)O>CCCCCNc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-18852d1d6f74444099f46b4384b87865 | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)COc1ccccc1>>O=C1CCC(N2C(=O)c3cccc(NC(=O)COc4ccccc4)c3C2=O)C(=O)N1 | NC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.O(C1=CC=CC=C1)CC(=O)Cl.CO>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(COC1=CC=CC=C1)=O)=O)=O | [O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([NH2:14])[c:25]3[C:26]2=[O:27])[C:28](=[O:29])[NH:30]1.Cl[C:15](=[O:16])[CH2:17][O:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([NH:14][C:15](=[O... | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)COc1ccccc1 | O=C1CCC(N2C(=O)c3cccc(NC(=O)COc4ccccc4)c3C2=O)C(=O)N1 | null | null | C1CCOC1.C(C)OCC | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CCC(N2C(=O)c3cccc(NC(=O)COc4ccccc4)c3C2=O)C(=O)N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4].[#7:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](-[NH2;D1;+0:10]):[c:11]>>[#7:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4]):[c:11] | 93.3 | [{"value": 93.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(COC1=CC=CC=C1)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.3, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(COC1=CC=CC=C1)=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a suspension of 4-amino-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione (0.55 g, 2 mmol) in THF (30 ml) was added phenoxyacetyl chloride (0.55 ml, 4 mmol). The mixture was heated to reflux for 18 hours. The reaction was cooled to room temperature, methanol (2 ml) was added, and the mixture stirred for 1 hour. The so... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CCNCC1.c1ccc2c(c1)C[NH]C2.c1ccccc1 | HCl | C1CCOC1.C(C)OCC | null | 1 | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)COc1ccccc1>C1CCOC1.C(C)OCC>O=C1CCC(N2C(=O)c3cccc(NC(=O)COc4ccccc4)c3C2=O)C(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a8192febdd6b4961a69af01f02677cb3 | CCCCCNc1cccc(C(=O)OC)c1C(=O)OC.O=CCOCc1ccccc1>>COC(=O)c1cccc(NCCOCc2ccccc2)c1C(=O)OC | C(C1=CC=CC=C1)OCC=O.COC(C=1C(C(=O)OC)=C(C=CC1)NCCCCC)=O>>COC(C=1C(C(=O)OC)=C(C=CC1)NCCOCC1=CC=CC=C1)=O | CCCCC[NH:10][c:9]1[cH:8][cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:21]1[C:22](=[O:23])[O:24][CH3:25].O=[CH:11][CH2:12][O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([NH:10][CH2:11][CH2:12][O:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[c:... | CCCCCNc1cccc(C(=O)OC)c1C(=O)OC.O=CCOCc1ccccc1 | COC(=O)c1cccc(NCCOCc2ccccc2)c1C(=O)OC | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | fc9422fe50863a8e7b22fcc145dd01d982e3de4e7dec633bf5d0e217ba35cfe6 | 7adcd96acc7986e995a59780d11a29072ec6cdad41c8d7f65df5f25f2d933fc4 | c1ccc(COCCNc2ccccc2)cc1 | C-C-C-C-C-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](-[#8:6])=[O;D1;H0:7].O=[CH;D2;+0:8]-[C:9]-[#8:10]>>[#8:10]-[C:9]-[CH2;D2;+0:8]-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](-[#8:6])=[O;D1;H0:7] | 78 | [{"value": 78.0, "product": "COC(C=1C(C(=O)OC)=C(C=CC1)NCCOCC1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Benzyloxyacetaldehyde (5.27 ml, 37.5 mmol) was treated in the same manner as described above for the synthesis of 3-pentylamino-phthalic acid dimethyl ester. The residue (oil) was purified by chromatography (6:3:1 methylene chloride/hexane/ethyl acetate) to give 7.98 g (78%) of yellow oil: 1H NMR (DMSO-d6) d 7.38–7.26 ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | CCCCCNc1cccc(C(=O)OC)c1C(=O)OC.O=CCOCc1ccccc1>>COC(=O)c1cccc(NCCOCc2ccccc2)c1C(=O)OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fa22e2a72a7b41c18b5774c454221a27 | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1cccc(F)c1>>O=C1CCC(N2C(=O)c3cccc(NC(=O)c4cccc(F)c4)c3C2=O)C(=O)N1 | NC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.FC=1C=C(C(=O)Cl)C=CC1.CO>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(C1=CC(=CC=C1)F)=O)=O)=O | [O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([NH2:14])[c:24]3[C:25]2=[O:26])[C:27](=[O:28])[NH:29]1.Cl[C:15](=[O:16])[c:17]1[cH:18][cH:19][cH:20][c:21]([F:22])[cH:23]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([NH:14][C:15](=[O:16])[c... | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1cccc(F)c1 | O=C1CCC(N2C(=O)c3cccc(NC(=O)c4cccc(F)c4)c3C2=O)C(=O)N1 | null | null | C1CCOC1.C(C)OCC | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CCC(N2C(=O)c3cccc(NC(=O)c4ccccc4)c3C2=O)C(=O)N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[NH2;D1;+0:11]):[c:12]>>[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]):[c:12] | 96 | [{"value": 96.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(C1=CC(=CC=C1)F)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.3, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(C1=CC(=CC=C1)F)=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a suspension of 4-amino-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione (0.55 g, 2 mmol) in THF (30 ml) was added 3-Fluorobenzoyl chloride (0.49 ml, 4 mmol). The mixture was heated to reflux for 18 hours. The reaction was cooled to room temperature, methanol (2 ml) was added, and the mixture stirred for 1 hour. The ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CCNCC1.c1ccc2c(c1)C[NH]C2.c1ccccc1 | HCl | C1CCOC1.C(C)OCC | null | 1 | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1cccc(F)c1>C1CCOC1.C(C)OCC>O=C1CCC(N2C(=O)c3cccc(NC(=O)c4cccc(F)c4)c3C2=O)C(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8632a3826de74800aa3c36050ee9a949 | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1cccc(C(F)(F)F)c1>>O=C1CCC(N2C(=O)c3cccc(NC(=O)c4cccc(C(F)(F)F)c4)c3C2=O)C(=O)N1 | NC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.FC(C=1C=C(C(=O)Cl)C=CC1)(F)F.CO>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(C1=CC(=CC=C1)C(F)(F)F)=O)=O)=O | [O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([NH2:14])[c:27]3[C:28]2=[O:29])[C:30](=[O:31])[NH:32]1.Cl[C:15](=[O:16])[c:17]1[cH:18][cH:19][cH:20][c:21]([C:22]([F:23])([F:24])[F:25])[cH:26]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([N... | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1cccc(C(F)(F)F)c1 | O=C1CCC(N2C(=O)c3cccc(NC(=O)c4cccc(C(F)(F)F)c4)c3C2=O)C(=O)N1 | null | null | C1CCOC1.C(C)OCC | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CCC(N2C(=O)c3cccc(NC(=O)c4ccccc4)c3C2=O)C(=O)N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[NH2;D1;+0:11]):[c:12]>>[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]):[c:12] | 46 | [{"value": 46.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(C1=CC(=CC=C1)C(F)(F)F)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(C1=CC(=CC=C1)C(F)(F)F)=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a suspension of 4-amino-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione (0.55 g, 2 mmol) in THF (30 ml) was added 3-trifluoromethylbenzoyl chloride (0.60 ml, 4 mmol). The mixture was heated to reflux for 18 hours. The reaction was cooled to room temperature, methanol (2 ml) was added, and the mixture stirred for 1 h... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CCNCC1.c1ccc2c(c1)C[NH]C2.c1ccccc1 | HCl | C1CCOC1.C(C)OCC | null | 1 | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1cccc(C(F)(F)F)c1>C1CCOC1.C(C)OCC>O=C1CCC(N2C(=O)c3cccc(NC(=O)c4cccc(C(F)(F)F)c4)c3C2=O)C(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-10db7d502845422ca3cf261d0458cb5d | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1cccc([N+](=O)[O-])c1>>O=C1CCC(N2C(=O)c3cccc(NC(=O)c4cccc([N+](=O)[O-])c4)c3C2=O)C(=O)N1 | NC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.[N+](=O)([O-])C=1C=C(C(=O)Cl)C=CC1.CO>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(C1=CC(=CC=C1)[N+](=O)[O-])=O)=O)=O | [O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([NH2:14])[c:26]3[C:27]2=[O:28])[C:29](=[O:30])[NH:31]1.Cl[C:15](=[O:16])[c:17]1[cH:18][cH:19][cH:20][c:21]([N+:22](=[O:23])[O-:24])[cH:25]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([NH:14]... | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1cccc([N+](=O)[O-])c1 | O=C1CCC(N2C(=O)c3cccc(NC(=O)c4cccc([N+](=O)[O-])c4)c3C2=O)C(=O)N1 | null | null | C1CCOC1.C(C)OCC | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CCC(N2C(=O)c3cccc(NC(=O)c4ccccc4)c3C2=O)C(=O)N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[NH2;D1;+0:11]):[c:12]>>[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]):[c:12] | 95 | [{"value": 95.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(C1=CC(=CC=C1)[N+](=O)[O-])=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.7, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(C1=CC(=CC=C1)[N+](=O)[O-])=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a suspension of 4-amino-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione (1.10 g, 4 mmol) in THF (30 ml) was added 3-nitrobenzoyl chloride (1.48 g, 8 mmol). The mixture was heated to reflux for 18 hours. The reaction was cooled to room temperature, methanol (2 ml) was added, and the mixture stirred for 1 hour. The so... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CCNCC1.c1ccc2c(c1)C[NH]C2.c1ccccc1 | HCl | C1CCOC1.C(C)OCC | null | 1 | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1cccc([N+](=O)[O-])c1>C1CCOC1.C(C)OCC>O=C1CCC(N2C(=O)c3cccc(NC(=O)c4cccc([N+](=O)[O-])c4)c3C2=O)C(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e7e6311d096a476e84425d47c1600a34 | CCCC(=O)Cl.Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>>CCCC(=O)Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | NC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.C(CCC)(=O)Cl.CO>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(CCC)=O)=O)=O | Cl[C:4]([CH2:3][CH2:2][CH3:1])=[O:5].[NH2:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[C:13](=[O:14])[N:15]([CH:16]1[CH2:17][CH2:18][C:19](=[O:20])[NH:21][C:22]1=[O:23])[C:24]2=[O:25]>>[CH3:1][CH2:2][CH2:3][C:4](=[O:5])[NH:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[C:13](=[O:14])[N:15]([CH:16]1[CH2:17][CH2:18][C:19](=[O:20... | CCCC(=O)Cl.Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | CCCC(=O)Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | null | null | C1CCOC1.C(C)OCC | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[#7:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](-[NH2;D1;+0:10]):[c:11]>>[#7:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]):[c:11] | 80.1 | [{"value": 80.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(CCC)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.1, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(CCC)=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a suspension of 4-amino-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione (0.55 g, 2 mmol) in THF (30 ml) was added butanoyl chloride (0.42 ml, 4 mmol). The mixture was heated to reflux for 18 hours. The reaction was cooled to room temperature, methanol (2 ml) was added, and the mixture stirred for 1 hour. The solvent... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2c(c1)C[NH]C2.C1CCNCC1 | HCl | C1CCOC1.C(C)OCC | null | 1 | CCCC(=O)Cl.Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>C1CCOC1.C(C)OCC>CCCC(=O)Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d9ecf58554e04c83a235de2184551fb7 | CCCCCCC=O.Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>>CCCCCCCNc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | [BH4-].[Na+].NC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.C(CCCCCC)=O.C(C)(=O)O.[BH4-].[Na+]>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NCCCCCCC)=O)=O | O=[CH:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1].[NH2:8][c:9]1[cH:10][cH:11][cH:12][c:13]2[c:14]1[C:15](=[O:16])[N:17]([CH:18]1[CH2:19][CH2:20][C:21](=[O:22])[NH:23][C:24]1=[O:25])[C:26]2=[O:27]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH:8][c:9]1[cH:10][cH:11][cH:12][c:13]2[c:14]1[C:15](=[O:16])[N:17]([CH:... | CCCCCCC=O.Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | CCCCCCCNc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1 | O=[CH;D2;+0:1]-[C:2]-[C:3].[#7:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[NH2;D1;+0:9]):[c:10]>>[#7:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[NH;D2;+0:9]-[CH2;D2;+0:1]-[C:2]-[C:3]):[c:10] | 41.1 | [{"value": 41.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NCCCCCCC)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 41.1, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NCCCCCCC)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A mixture of 4-amino-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione (1.1 g, 4.0 mmol) and heptanal (3.4 mL, 24 mmol) and acetic acid (2 mL) in DMF (20 mL) was heated until all solid was dissolved. To the mixture was added sodium borohydride (605 mg, 16 mmol) and kept at room temperature for 18 h. To the mixture was ad... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccc2c(c1)C[NH]C2.C1CCNCC1 | Other | CN(C)C=O | null | 18 | CCCCCCC=O.Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>CN(C)C=O>CCCCCCCNc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7911f6166c4a4a53b14e1cb9381ba0a3 | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1ccc(Cl)cc1>>O=C1CCC(N2C(=O)c3cccc(NC(=O)c4ccc(Cl)cc4)c3C2=O)C(=O)N1 | NC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.ClC1=CC=C(C(=O)Cl)C=C1.CO.CO>>ClC1=CC=C(C(=O)NC2=C3C(N(C(C3=CC=C2)=O)C2C(NC(CC2)=O)=O)=O)C=C1 | [O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([NH2:14])[c:24]3[C:25]2=[O:26])[C:27](=[O:28])[NH:29]1.Cl[C:15](=[O:16])[c:17]1[cH:18][cH:19][c:20]([Cl:21])[cH:22][cH:23]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([NH:14][C:15](=[O:16])[... | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1ccc(Cl)cc1 | O=C1CCC(N2C(=O)c3cccc(NC(=O)c4ccc(Cl)cc4)c3C2=O)C(=O)N1 | null | null | C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CCC(N2C(=O)c3cccc(NC(=O)c4ccccc4)c3C2=O)C(=O)N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[NH2;D1;+0:11]):[c:12]>>[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]):[c:12] | 81 | [{"value": 81.0, "product": "ClC1=CC=C(C(=O)NC2=C3C(N(C(C3=CC=C2)=O)C2C(NC(CC2)=O)=O)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.9, "product": "ClC1=CC=C(C(=O)NC2=C3C(N(C(C3=CC=C2)=O)C2C(NC(CC2)=O)=O)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 4-amino-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione (1.2 g, 4.5 mmol) and 4-chlorobenzoyl chloride (1.1 mL, 8.8 mmol) in THF (40 mL) was heated to reflux for 15 h. To the mixture was added methanol (5 mL) to give a suspension. The suspension was filtered and washed with ether (2×10 mL) then methanol (5... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CCNCC1.c1ccc2c(c1)C[NH]C2.c1ccccc1 | HCl | C1CCOC1 | null | null | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1ccc(Cl)cc1>C1CCOC1>O=C1CCC(N2C(=O)c3cccc(NC(=O)c4ccc(Cl)cc4)c3C2=O)C(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3cc38ad9cd46421d88aff5f121abcc75 | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)C1CC1>>O=C1CCC(N2C(=O)c3cccc(NC(=O)C4CC4)c3C2=O)C(=O)N1 | NC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.C1(CC1)C(=O)Cl.CO>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(=O)C1CC1)=O)=O | [O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([NH2:14])[c:20]3[C:21]2=[O:22])[C:23](=[O:24])[NH:25]1.Cl[C:15](=[O:16])[CH:17]1[CH2:18][CH2:19]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([NH:14][C:15](=[O:16])[CH:17]4[CH2:18][CH2:19]4)[... | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)C1CC1 | O=C1CCC(N2C(=O)c3cccc(NC(=O)C4CC4)c3C2=O)C(=O)N1 | null | null | C1CCOC1.CCOCC | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CCC(N2C(=O)c3cccc(NC(=O)C4CC4)c3C2=O)C(=O)N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[C:5]-1.[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[NH2;D1;+0:11]):[c:12]>>[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[C:5]-1):[c:12] | 84 | [{"value": 84.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(=O)C1CC1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.9, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(=O)C1CC1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 4-amino-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione (0.60 g, 2.2 mmol) and cyclopropanecarbonyl chloride (0.4 mL, 4.4 mmol) in THF (20 mL) was heated to reflux for 15 h. To the mixture was added methanol (5 mL). The solvent was removed in vacuo to give a solid. The solid was slurried in ether (30 mL0 f... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CCNCC1.c1ccc2c(c1)C[NH]C2.C1CC1 | HCl | C1CCOC1.CCOCC | null | null | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)C1CC1>C1CCOC1.CCOCC>O=C1CCC(N2C(=O)c3cccc(NC(=O)C4CC4)c3C2=O)C(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1ff980c7044048ed8d2292d125e568d4 | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1ccc(F)cc1>>O=C1CCC(N2C(=O)c3cccc(NC(=O)c4ccc(F)cc4)c3C2=O)C(=O)N1 | NC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.FC1=CC=C(C(=O)Cl)C=C1.CO.CO>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(C1=CC=C(C=C1)F)=O)=O)=O | [O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([NH2:14])[c:24]3[C:25]2=[O:26])[C:27](=[O:28])[NH:29]1.Cl[C:15](=[O:16])[c:17]1[cH:18][cH:19][c:20]([F:21])[cH:22][cH:23]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([NH:14][C:15](=[O:16])[c... | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1ccc(F)cc1 | O=C1CCC(N2C(=O)c3cccc(NC(=O)c4ccc(F)cc4)c3C2=O)C(=O)N1 | null | null | C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CCC(N2C(=O)c3cccc(NC(=O)c4ccccc4)c3C2=O)C(=O)N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[NH2;D1;+0:11]):[c:12]>>[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]):[c:12] | 77 | [{"value": 77.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(C1=CC=C(C=C1)F)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.9, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(C1=CC=C(C=C1)F)=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 4-amino-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione (1.1 g, 4.0 mmol) and 4-fluorobenzoyl chloride (0.95 mL, 8.0 mmol) in THF (40 mL) was heated to reflux for 15 h. To the mixture was added methanol (5 mL) to give a suspension. The suspension was filtered and washed with ether (2×10 mL) then methanol (... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CCNCC1.c1ccc2c(c1)C[NH]C2.c1ccccc1 | HCl | C1CCOC1 | null | null | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1ccc(F)cc1>C1CCOC1>O=C1CCC(N2C(=O)c3cccc(NC(=O)c4ccc(F)cc4)c3C2=O)C(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-09c6019797e746399af80e06dca45d42 | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1ccc(C(F)(F)F)cc1>>O=C1CCC(N2C(=O)c3cccc(NC(=O)c4ccc(C(F)(F)F)cc4)c3C2=O)C(=O)N1 | NC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.FC(C1=CC=C(C(=O)Cl)C=C1)(F)F>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(C1=CC=C(C=C1)C(F)(F)F)=O)=O)=O | [O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([NH2:14])[c:27]3[C:28]2=[O:29])[C:30](=[O:31])[NH:32]1.Cl[C:15](=[O:16])[c:17]1[cH:18][cH:19][c:20]([C:21]([F:22])([F:23])[F:24])[cH:25][cH:26]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([N... | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1ccc(C(F)(F)F)cc1 | O=C1CCC(N2C(=O)c3cccc(NC(=O)c4ccc(C(F)(F)F)cc4)c3C2=O)C(=O)N1 | null | null | CO.C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CCC(N2C(=O)c3cccc(NC(=O)c4ccccc4)c3C2=O)C(=O)N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[NH2;D1;+0:11]):[c:12]>>[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]):[c:12] | 77 | [{"value": 77.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(C1=CC=C(C=C1)C(F)(F)F)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.5, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(C1=CC=C(C=C1)C(F)(F)F)=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 4-amino-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione (0.6 g, 2.2 mmol) and 4-(trifluoromethyl)benzoyl chloride (1 g, 4.8 mmol) in THF (20 mL) was heated to reflux for 15 h. The solvent was removed in vacuo to give a solid. The solid was slurried in methanol (20 mL) for 2 h. The suspension was filtered a... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CCNCC1.c1ccc2c(c1)C[NH]C2.c1ccccc1 | HCl | CO.C1CCOC1 | null | null | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1ccc(C(F)(F)F)cc1>CO.C1CCOC1>O=C1CCC(N2C(=O)c3cccc(NC(=O)c4ccc(C(F)(F)F)cc4)c3C2=O)C(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6942dc519f154105be16c14c2f26dfb0 | Cc1ccc(C(=O)Cl)cc1.Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>>Cc1ccc(C(=O)Nc2cccc3c2C(=O)N(C2CCC(=O)NC2=O)C3=O)cc1 | NC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.CC1=CC=C(C(=O)Cl)C=C1.CO>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(C1=CC=C(C=C1)C)=O)=O)=O | Cl[C:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:29][cH:28]1)=[O:7].[NH2:8][c:9]1[cH:10][cH:11][cH:12][c:13]2[c:14]1[C:15](=[O:16])[N:17]([CH:18]1[CH2:19][CH2:20][C:21](=[O:22])[NH:23][C:24]1=[O:25])[C:26]2=[O:27]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][cH:12][c:13]3[c:14]2[C:15](=[O:16])[N:1... | Cc1ccc(C(=O)Cl)cc1.Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | Cc1ccc(C(=O)Nc2cccc3c2C(=O)N(C2CCC(=O)NC2=O)C3=O)cc1 | null | null | C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CCC(N2C(=O)c3cccc(NC(=O)c4ccccc4)c3C2=O)C(=O)N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[NH2;D1;+0:11]):[c:12]>>[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]):[c:12] | 83 | [{"value": 83.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(C1=CC=C(C=C1)C)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(C1=CC=C(C=C1)C)=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 4-amino-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione (1.1 g, 4.0 mmol) and 4-methylbenzoyl chloride (1.1 g, 8.0 mmol) in THF (40 mL) was heated to reflux for 36 h. To the mixture was added methanol (5 mL) to give a suspension. The suspension was filtered and washed with methanol (15 mL) to give N-[2-(2,... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2.C1CCNCC1 | HCl | C1CCOC1 | null | null | Cc1ccc(C(=O)Cl)cc1.Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>C1CCOC1>Cc1ccc(C(=O)Nc2cccc3c2C(=O)N(C2CCC(=O)NC2=O)C3=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-16d06fc9f5094318aaffc5b65a6a9f9b | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1ccc([N+](=O)[O-])cc1>>O=C1CCC(N2C(=O)c3cccc(NC(=O)c4ccc([N+](=O)[O-])cc4)c3C2=O)C(=O)N1 | NC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.[N+](=O)([O-])C1=CC=C(C(=O)Cl)C=C1.CO>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(C1=CC=C(C=C1)[N+](=O)[O-])=O)=O)=O | [O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([NH2:14])[c:26]3[C:27]2=[O:28])[C:29](=[O:30])[NH:31]1.Cl[C:15](=[O:16])[c:17]1[cH:18][cH:19][c:20]([N+:21](=[O:22])[O-:23])[cH:24][cH:25]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([NH:14]... | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1ccc([N+](=O)[O-])cc1 | O=C1CCC(N2C(=O)c3cccc(NC(=O)c4ccc([N+](=O)[O-])cc4)c3C2=O)C(=O)N1 | null | null | C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CCC(N2C(=O)c3cccc(NC(=O)c4ccccc4)c3C2=O)C(=O)N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[NH2;D1;+0:11]):[c:12]>>[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]):[c:12] | 74 | [{"value": 73.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(C1=CC=C(C=C1)[N+](=O)[O-])=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(C1=CC=C(C=C1)[N+](=O)[O-])=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 4-amino-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione (2.2 g, 8.0 mmol) and 4-nitrobenzoyl chloride (3.0 g, 16.0 mmol) in THF (80 mL) was heated to reflux for 15 h. To the mixture was added methanol (20 mL) to give a suspension. The suspension was filtered and washed with methanol (20 mL) to give N-[2-(2... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CCNCC1.c1ccc2c(c1)C[NH]C2.c1ccccc1 | HCl | C1CCOC1 | null | null | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1ccc([N+](=O)[O-])cc1>C1CCOC1>O=C1CCC(N2C(=O)c3cccc(NC(=O)c4ccc([N+](=O)[O-])cc4)c3C2=O)C(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0aec7bc16da1406f8e6c49d1bdaea733 | CCOCC(=O)O.Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>>CCOCC(=O)Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | C(C)OCC(=O)O.C(C(=O)Cl)(=O)Cl.CN(C)C=O.NC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(COCC)=O)=O)=O | O[C:5]([CH2:4][O:3][CH2:2][CH3:1])=[O:6].[NH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[C:14](=[O:15])[N:16]([CH:17]1[CH2:18][CH2:19][C:20](=[O:21])[NH:22][C:23]1=[O:24])[C:25]2=[O:26]>>[CH3:1][CH2:2][O:3][CH2:4][C:5](=[O:6])[NH:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[C:14](=[O:15])[N:16]([CH:17]1[CH2:18][CH2:19][C... | CCOCC(=O)O.Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | CCOCC(=O)Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | null | null | CO.C1CCOC1.CCOCC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4].[#7:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](-[NH2;D1;+0:10]):[c:11]>>[#7:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4]):[c:11] | 90.4 | [{"value": 87.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(COCC)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.4, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(COCC)=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of ethoxyacetic acid (0.8 mL, 8.5 mmol) and oxalyl chloride (0.7 mL, 8.0 mmol) in ether (5 mL) was added DMF (0.03 mL) at room temperature. After 3 h, 4-amino-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione (1.1 g, 4.0 mmol) and THF (40 mL) was added to the mixture. Then the mixture was heated to reflux f... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2c(c1)C[NH]C2.C1CCNCC1 | HO- | CO.C1CCOC1.CCOCC | null | 3 | CCOCC(=O)O.Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>CO.C1CCOC1.CCOCC>CCOCC(=O)Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8641bf4c07dd4608a91e498d42de4a6f | CSCC(=O)O.Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>>CSCC(=O)Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | CSCC(=O)O.C(C(=O)Cl)(=O)Cl.CN(C)C=O.NC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(CSC)=O)=O)=O | O[C:4]([CH2:3][S:2][CH3:1])=[O:5].[NH2:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[C:13](=[O:14])[N:15]([CH:16]1[CH2:17][CH2:18][C:19](=[O:20])[NH:21][C:22]1=[O:23])[C:24]2=[O:25]>>[CH3:1][S:2][CH2:3][C:4](=[O:5])[NH:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[C:13](=[O:14])[N:15]([CH:16]1[CH2:17][CH2:18][C:19](=[O:20])[NH... | CSCC(=O)O.Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | CSCC(=O)Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | null | null | CO.C1CCOC1.CCOCC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#16:4].[#7:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](-[NH2;D1;+0:10]):[c:11]>>[#16:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[c:9](:[c:11]):[c:8]-[C:6](=[O;D1;H0:7])-[#7:5] | 69.2 | [{"value": 69.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(CSC)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.2, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(CSC)=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of (methylthio)acetic acid (0.77 mL, 8.9 mmol) and oxalyl chloride (0.7 mL, 8.0 mmol) in ether (5 mL) was added DMF (0.02 mL) at room temperature. After 3 h, 4-amino-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione (1.1 g, 4.0 mmol) and THF (40 mL) was added to the mixture. Then the mixture was heated to r... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2c(c1)C[NH]C2.C1CCNCC1 | HO- | CO.C1CCOC1.CCOCC | null | 3 | CSCC(=O)O.Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>CO.C1CCOC1.CCOCC>CSCC(=O)Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-466b3109d33148f7accdb7864e1a1c76 | COc1ccccc1C(=O)Cl.Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>>COc1ccccc1C(=O)Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | NC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.COC1=C(C(=O)Cl)C=CC=C1.CO>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(C1=C(C=CC=C1)OC)=O)=O)=O | Cl[C:9]([c:8]1[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]1)=[O:10].[NH2:11][c:12]1[cH:13][cH:14][cH:15][c:16]2[c:17]1[C:18](=[O:19])[N:20]([CH:21]1[CH2:22][CH2:23][C:24](=[O:25])[NH:26][C:27]1=[O:28])[C:29]2=[O:30]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[C:9](=[O:10])[NH:11][c:12]1[cH:13][cH:14][cH:15][c:16]2... | COc1ccccc1C(=O)Cl.Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | COc1ccccc1C(=O)Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | null | null | C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CCC(N2C(=O)c3cccc(NC(=O)c4ccccc4)c3C2=O)C(=O)N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[NH2;D1;+0:11]):[c:12]>>[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]):[c:12] | 78 | [{"value": 78.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(C1=C(C=CC=C1)OC)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.7, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(C1=C(C=CC=C1)OC)=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 4-amino-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione (660 mg, 2.4 mmol) and 2-methoxybenzoyl chloride (0.7 mL, 4.7 mmol) in THF (20 mL) was heated to reflux for 15 h. To the mixture was added methanol (5 mL) to give a suspension. The suspension was filtered and washed with methanol (20 mL) to give N-[2-... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2.C1CCNCC1 | HCl | C1CCOC1 | null | null | COc1ccccc1C(=O)Cl.Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>C1CCOC1>COc1ccccc1C(=O)Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b70154211f7644a99ea0a75986065106 | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1ccccc1F>>O=C1CCC(N2C(=O)c3cccc(NC(=O)c4ccccc4F)c3C2=O)C(=O)N1 | NC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.FC1=C(C(=O)Cl)C=CC=C1.CO>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(C1=C(C=CC=C1)F)=O)=O)=O | [O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([NH2:14])[c:24]3[C:25]2=[O:26])[C:27](=[O:28])[NH:29]1.Cl[C:15](=[O:16])[c:17]1[cH:18][cH:19][cH:20][cH:21][c:22]1[F:23]>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([NH:14][C:15](=[O:16])[c:1... | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1ccccc1F | O=C1CCC(N2C(=O)c3cccc(NC(=O)c4ccccc4F)c3C2=O)C(=O)N1 | null | null | C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CCC(N2C(=O)c3cccc(NC(=O)c4ccccc4)c3C2=O)C(=O)N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[NH2;D1;+0:11]):[c:12]>>[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]):[c:12] | 94.9 | [{"value": 93.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(C1=C(C=CC=C1)F)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.9, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NC(C1=C(C=CC=C1)F)=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 4-amino-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione (1.1 g, 4.0 mmol) and 2-fluorobenzoyl chloride (1.0 mL, 8.4 mmol) in THF (40 mL) was heated to reflux for 15 h. To the mixture was added methanol (10 mL) to give a suspension. The suspension was filtered and washed with methanol (20 mL) to give N-[2-(... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CCNCC1.c1ccc2c(c1)C[NH]C2.c1ccccc1 | HCl | C1CCOC1 | null | null | Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1ccccc1F>C1CCOC1>O=C1CCC(N2C(=O)c3cccc(NC(=O)c4ccccc4F)c3C2=O)C(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2558df62207c40d7ac489a7fbb763041 | CCCC(=O)Cl.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>>CCCC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | N12CCCCCC2=NCCC1.Cl.NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.C(CCC)(=O)Cl>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(CCC)=O)=O)=O | Cl[C:4]([CH2:3][CH2:2][CH3:1])=[O:5].[NH2:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[C:14](=[O:15])[N:16]([CH:17]1[CH2:18][CH2:19][C:20](=[O:21])[NH:22][C:23]1=[O:24])[C:25]2=[O:26]>>[CH3:1][CH2:2][CH2:3][C:4](=[O:5])[NH:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[C:14](=[O:15])[N:16]([CH:17]1[CH2:18][CH2:... | CCCC(=O)Cl.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | CCCC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | null | null | CC#N | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[C:6]-[c:7]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[C:6]-[c:7] | 62 | [{"value": 62.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(CCC)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(CCC)=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | 1,8-Diazabicyclo[5,4,0]undec-7-ene (0.62 g, 4.08 mmol) was added to a stirred suspension of 4-(aminomethyl)-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione hydrochloride (0.6 g, 1.85 mmol) in CH3CN (50 mL). After stirring for 20 min, butyryl chloride (0.24 g, 2.22 mmol) was added. The mixture was stirred at room temper... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2c(c1)C[NH]C2.C1CCNCC1 | HCl | CC#N | null | 0.333333 | CCCC(=O)Cl.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>CC#N>CCCC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-111ce111283f4234bd35ba15023578dc | NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1ccccc1>>O=C1CCC(N2C(=O)c3cccc(CNC(=O)c4ccccc4)c3C2=O)C(=O)N1 | N12CCCCCC2=NCCC1.Cl.NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.C(C1=CC=CC=C1)(=O)Cl>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(C1=CC=CC=C1)=O)=O)=O | [O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([CH2:14][NH2:15])[c:24]3[C:25]2=[O:26])[C:27](=[O:28])[NH:29]1.Cl[C:16](=[O:17])[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([CH2:14][NH:15][C:16](=... | NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1ccccc1 | O=C1CCC(N2C(=O)c3cccc(CNC(=O)c4ccccc4)c3C2=O)C(=O)N1 | null | null | CC#N | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CCC(N2C(=O)c3cccc(CNC(=O)c4ccccc4)c3C2=O)C(=O)N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[C:7]-[c:8]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[C:7]-[c:8])-[c:3](:[c:4]):[c:5] | 76 | [{"value": 76.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(C1=CC=CC=C1)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(C1=CC=CC=C1)=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | 1,8-Diazabicyclo[5,4,0]undec-7-ene (0.62 g, 4.08 mmol) was added to a stirred suspension of 4-(aminomethyl)-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione hydrochloride (0.6 g, 1.85 mmol) in CH3CN (50 mL). After stirring for 20 min, benzoyl chloride (0.31 g, 2.22 mmol) was added. The mixture was stirred at room temper... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CCNCC1.c1ccc2c(c1)C[NH]C2.c1ccccc1 | HCl | CC#N | null | 0.333333 | NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)c1ccccc1>CC#N>O=C1CCC(N2C(=O)c3cccc(CNC(=O)c4ccccc4)c3C2=O)C(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6906bd3545ea4d2395df375b907c7f9b | NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)Cc1ccccc1>>O=C(Cc1ccccc1)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | N12CCCCCC2=NCCC1.Cl.NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.C1(=CC=CC=C1)CC(=O)Cl>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(CC1=CC=CC=C1)=O)=O)=O | [NH2:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][c:16]2[c:17]1[C:18](=[O:19])[N:20]([CH:21]1[CH2:22][CH2:23][C:24](=[O:25])[NH:26][C:27]1=[O:28])[C:29]2=[O:30].Cl[C:2](=[O:1])[CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[NH:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][c:... | NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)Cc1ccccc1 | O=C(Cc1ccccc1)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | null | null | CC#N | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Cc1ccccc1)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[NH2;D1;+0:5]-[C:6]-[c:7]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3]-[c:4])-[NH;D2;+0:5]-[C:6]-[c:7] | 55 | [{"value": 55.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(CC1=CC=CC=C1)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.7, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(CC1=CC=CC=C1)=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | 1,8-Diazabicyclo[5,4,0]undec-7-ene (0.65 g, 4.26mmol) was added to a stirred suspension of 4-(aminomethyl)-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione hydrochloride (0.60 g, 1.85 mmol) in CH3CN (50 mL). After stirring for 20 min, phenylacetyl chloride (0.35 g, 2.22mmol) was added. The mixture was stirred at room te... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2.C1CCNCC1 | HCl | CC#N | null | 0.333333 | NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)Cc1ccccc1>CC#N>O=C(Cc1ccccc1)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cb2d2db38aa7452f9ba7c7edf00f2bb5 | NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)C1CCCC1>>O=C1CCC(N2C(=O)c3cccc(CNC(=O)C4CCCC4)c3C2=O)C(=O)N1 | N12CCCCCC2=NCCC1.Cl.NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.C1(CCCC1)C(=O)Cl>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)C1CCCC1)=O)=O | [O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([CH2:14][NH2:15])[c:23]3[C:24]2=[O:25])[C:26](=[O:27])[NH:28]1.Cl[C:16](=[O:17])[CH:18]1[CH2:19][CH2:20][CH2:21][CH2:22]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([CH2:14][NH:15][C:16](=[O... | NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)C1CCCC1 | O=C1CCC(N2C(=O)c3cccc(CNC(=O)C4CCCC4)c3C2=O)C(=O)N1 | null | null | CC#N | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CCC(N2C(=O)c3cccc(CNC(=O)C4CCCC4)c3C2=O)C(=O)N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[NH2;D1;+0:6]-[C:7]-[c:8]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[C:7]-[c:8])-[C:5] | 83.2 | [{"value": 83.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)C1CCCC1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.2, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)C1CCCC1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | 1,8-Diazabicyclo[5,4,0]undec-7-ene (0.62 g, 4.08 mmol) was added to a stirred suspension of 4-(aminomethyl)-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione hydrochloride (0.60 g, 1.85 mmol) in CH3CN (50 mL). After stirring for 20 min, cyclopentanecarbonyl chloride (0.29 g, 2.22 mmol) was added. The mixture was stirred ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CCNCC1.c1ccc2c(c1)C[NH]C2.C1CCCC1 | HCl | CC#N | null | 0.333333 | NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)C1CCCC1>CC#N>O=C1CCC(N2C(=O)c3cccc(CNC(=O)C4CCCC4)c3C2=O)C(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8282c79fceb34b179b50e433d37322d7 | NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)C1CCCCC1>>O=C1CCC(N2C(=O)c3cccc(CNC(=O)C4CCCCC4)c3C2=O)C(=O)N1 | N12CCCCCC2=NCCC1.Cl.NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.C1(CCCCC1)C(=O)Cl>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)C1CCCCC1)=O)=O | [O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([CH2:14][NH2:15])[c:24]3[C:25]2=[O:26])[C:27](=[O:28])[NH:29]1.Cl[C:16](=[O:17])[CH:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([CH2:14][NH:15][C... | NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)C1CCCCC1 | O=C1CCC(N2C(=O)c3cccc(CNC(=O)C4CCCCC4)c3C2=O)C(=O)N1 | null | null | CC#N | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CCC(N2C(=O)c3cccc(CNC(=O)C4CCCCC4)c3C2=O)C(=O)N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[NH2;D1;+0:6]-[C:7]-[c:8]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[C:7]-[c:8])-[C:5] | 72.1 | [{"value": 72.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)C1CCCCC1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.1, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)C1CCCCC1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | 1,8-Diazabicyclo[5,4,0]undec-7-ene (0.62 g, 4.08 mmol) was added to a stirred suspension of 4-(aminomethyl)-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione hydrochloride (0.60 g, 1.85 mmol) in CH3CN (50 mL). After stirring for 20 min, cyclohexanecarbonyl chloride (0.33 g, 2.22 mmol) was added. The mixture was stirred a... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CCNCC1.c1ccc2c(c1)C[NH]C2.C1CCCCC1 | HCl | CC#N | null | 0.333333 | NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)C1CCCCC1>CC#N>O=C1CCC(N2C(=O)c3cccc(CNC(=O)C4CCCCC4)c3C2=O)C(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8d92a87056ae479f96903e38dab5bfeb | NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C=Nc1ccccc1>>O=C1CCC(N2C(=O)c3cccc(CNC(=O)Nc4ccccc4)c3C2=O)C(=O)N1 | N12CCCCCC2=NCCC1.Cl.NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.C1(=CC=CC=C1)N=C=O>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)NC1=CC=CC=C1)=O)=O | [O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([CH2:14][NH2:15])[c:25]3[C:26]2=[O:27])[C:28](=[O:29])[NH:30]1.[C:16](=[O:17])=[N:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([CH2:14][NH:15][C:... | NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C=Nc1ccccc1 | O=C1CCC(N2C(=O)c3cccc(CNC(=O)Nc4ccccc4)c3C2=O)C(=O)N1 | null | null | CC#N | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C1CCC(N2C(=O)c3cccc(CNC(=O)Nc4ccccc4)c3C2=O)C(=O)N1 | [NH2;D1;+0:1]-[C:2]-[c:3].[O;D1;H0:4]=[C;H0;D2;+0:5]=[N;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:4]=[C;H0;D3;+0:5](-[NH;D2;+0:1]-[C:2]-[c:3])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 31 | [{"value": 31.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)NC1=CC=CC=C1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 30.6, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)NC1=CC=CC=C1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | 1,8-Diazabicyclo[5,4,0]undec-7-ene (0.29 g. 1.90 mmol) was added to a stirred suspension of 4-(aminomethyl)-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione hydrochloride (0.6 g, 1.85 mmol) in CH3CN (50 mL). After stirring for 20 min, phenyl isocyanate (0.33 g, 2.77 mmol) was added. The mixture was stirred at room tempe... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | C1CCNCC1.c1ccc2c(c1)C[NH]C2.c1ccccc1 | null | CC#N | null | 0.333333 | NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C=Nc1ccccc1>CC#N>O=C1CCC(N2C(=O)c3cccc(CNC(=O)Nc4ccccc4)c3C2=O)C(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-66a3ea77b0e440e3847f18e88c61489f | CCCCN=C=O.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>>CCCCNC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | N12CCCCCC2=NCCC1.Cl.NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.C(CCC)N=C=O>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)NCCCC)=O)=O | [CH3:1][CH2:2][CH2:3][CH2:4][N:5]=[C:6]=[O:7].[NH2:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][c:14]2[c:15]1[C:16](=[O:17])[N:18]([CH:19]1[CH2:20][CH2:21][C:22](=[O:23])[NH:24][C:25]1=[O:26])[C:27]2=[O:28]>>[CH3:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:7])[NH:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][c:14]2[c:15]1[C:16](=[O:17])[N... | CCCCN=C=O.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | CCCCNC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | null | null | CC#N | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1 | [C:1]-[C:2]-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;D1;H0:5].[NH2;D1;+0:6]-[C:7]-[c:8]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[NH;D2;+0:6]-[C:7]-[c:8] | 61.6 | [{"value": 61.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)NCCCC)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.6, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)NCCCC)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | 1,8-Diazabicyclo[5,4,0]undec-7-ene (0.29 g, 1.90 mmol) was added to a stirred suspension of 4-(aminomethyl)-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione hydrochloride (0.6 g, 1.85 mmol) in CH3CN (50 mL). After stirring for 20 min, n-butyl isocyanate (0.27 g, 2.77 mmol) was added. The mixture was stirred at room temp... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccc2c(c1)C[NH]C2.C1CCNCC1 | null | CC#N | null | 0.333333 | CCCCN=C=O.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>CC#N>CCCCNC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cf4e3707b536411c9d42a3b2becaf890 | CCCN=C=O.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>>CCCNC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | N12CCCCCC2=NCCC1.Cl.NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.C(CC)N=C=O>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)NCCC)=O)=O | [CH3:1][CH2:2][CH2:3][N:4]=[C:5]=[O:6].[NH2:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][c:13]2[c:14]1[C:15](=[O:16])[N:17]([CH:18]1[CH2:19][CH2:20][C:21](=[O:22])[NH:23][C:24]1=[O:25])[C:26]2=[O:27]>>[CH3:1][CH2:2][CH2:3][NH:4][C:5](=[O:6])[NH:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][c:13]2[c:14]1[C:15](=[O:16])[N:17]([CH:18]1[CH... | CCCN=C=O.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | CCCNC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | null | null | CC#N | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1 | [C:1]-[C:2]-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;D1;H0:5].[NH2;D1;+0:6]-[C:7]-[c:8]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[NH;D2;+0:6]-[C:7]-[c:8] | 20 | [{"value": 20.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)NCCC)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 18.9, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)NCCC)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | 1,8-Diazabicyclo[5,4,0]undec-7-ene (0.29 g, 1.90 mmol) was added to a stirred suspension of 4-(aminomethyl)-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione hydrochloride (0.6 g, 1.85 mmol) in CH3CN (50 mL). After stirring for 20 min, propyl isocyanate (0.24 g, 2.77 mmol) was added. The mixture was stirred at room tempe... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccc2c(c1)C[NH]C2.C1CCNCC1 | null | CC#N | null | 0.333333 | CCCN=C=O.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>CC#N>CCCNC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3367d0836d0646aa957150d212631a26 | NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C=NC1CCCCC1>>O=C1CCC(N2C(=O)c3cccc(CNC(=O)NC4CCCCC4)c3C2=O)C(=O)N1 | N12CCCCCC2=NCCC1.Cl.NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.C1(CCCCC1)N=C=O>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)NC1CCCCC1)=O)=O | [O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([CH2:14][NH2:15])[c:25]3[C:26]2=[O:27])[C:28](=[O:29])[NH:30]1.[C:16](=[O:17])=[N:18][CH:19]1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([CH2:14][NH:... | NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C=NC1CCCCC1 | O=C1CCC(N2C(=O)c3cccc(CNC(=O)NC4CCCCC4)c3C2=O)C(=O)N1 | null | null | CC#N | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C1CCC(N2C(=O)c3cccc(CNC(=O)NC4CCCCC4)c3C2=O)C(=O)N1 | [C:1]-[C:2](-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;D1;H0:5])-[C:6].[NH2;D1;+0:7]-[C:8]-[c:9]>>[C:1]-[C:2](-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[NH;D2;+0:7]-[C:8]-[c:9])-[C:6] | 49 | [{"value": 49.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)NC1CCCCC1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.5, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)NC1CCCCC1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | 1,8-Diazabicyclo[5,4,0]undec-7-ene (0.29 g, 1.90 mmol) was added to a stirred suspension of 4-(aminomethyl)-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione hydrochloride (0.6 g, 1.85 mmol) in CH3CN (50 mL). After stirring for 20 min, cyclohexyl isocyanate (0.35 g, 2.77 mmol) was added. The mixture was stirred at room t... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | C1CCNCC1.c1ccc2c(c1)C[NH]C2.C1CCCCC1 | null | CC#N | null | 0.333333 | NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C=NC1CCCCC1>CC#N>O=C1CCC(N2C(=O)c3cccc(CNC(=O)NC4CCCCC4)c3C2=O)C(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-14a2688cb241477c9fd831bf678987b1 | CC(C)N=C=O.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>>CCN(C)C(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | N12CCCCCC2=NCCC1.Cl.NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.C(C)(C)N=C=O>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)N(CC)C)=O)=O | [CH3:1][CH:2]([N:3]=[C:5]=[O:6])[CH3:4].[NH2:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][c:13]2[c:14]1[C:15](=[O:16])[N:17]([CH:18]1[CH2:19][CH2:20][C:21](=[O:22])[NH:23][C:24]1=[O:25])[C:26]2=[O:27]>>[CH3:1][CH2:2][N:3]([CH3:4])[C:5](=[O:6])[NH:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][c:13]2[c:14]1[C:15](=[O:16])[N:17]([CH:18]1[... | CC(C)N=C=O.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | CCN(C)C(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | null | null | CC#N | Acylation | OtherReaction | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1 | [C;D1;H3:1]-[CH;D3;+0:2](-[CH3;D1;+0:3])-[N;H0;D2;+0:4]=[C;H0;D2;+0:5]=[O;D1;H0:6].[NH2;D1;+0:7]-[C:8]-[c:9]>>[C;D1;H3:1]-[CH2;D2;+0:2]-[N;H0;D3;+0:4](-[CH3;D1;+0:3])-[C;H0;D3;+0:5](=[O;D1;H0:6])-[NH;D2;+0:7]-[C:8]-[c:9] | 36.3 | [{"value": 36.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)N(CC)C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 36.3, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)N(CC)C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | 1,8-Diazabicyclo[5,4,0]undec-7-ene (0.29 g, 1.90 mmol) was added to a stirred suspension of 4-(aminomethyl)-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione hydrochloride (0.6 g, 1.85 mmol) in CH3CN (50 mL). After stirring for 20 min, isopropyl isocyanate (0.24 g, 2.77 mmol) was added. The mixture was stirred at room te... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccc2c(c1)C[NH]C2.C1CCNCC1 | null | CC#N | null | 0.333333 | CC(C)N=C=O.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>CC#N>CCN(C)C(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c583fa8758ec49a3b8d9af1a4fe2a2ac | CCCCCCCCN=C=O.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>>CCCCCCCCNC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | N12CCCCCC2=NCCC1.Cl.NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.C(CCCCCCC)N=C=O>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)NCCCCCCCC)=O)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]=[C:10]=[O:11].[NH2:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][c:18]2[c:19]1[C:20](=[O:21])[N:22]([CH:23]1[CH2:24][CH2:25][C:26](=[O:27])[NH:28][C:29]1=[O:30])[C:31]2=[O:32]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10](=[O:11])[NH:12][CH... | CCCCCCCCN=C=O.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | CCCCCCCCNC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | null | null | CC#N | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1 | [C:1]-[C:2]-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;D1;H0:5].[NH2;D1;+0:6]-[C:7]-[c:8]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[NH;D2;+0:6]-[C:7]-[c:8] | 56.2 | [{"value": 56.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)NCCCCCCCC)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.2, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)NCCCCCCCC)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | 1,8-Diazabicyclo[5,4,0]undec-7-ene (0.29 g, 1.90 mmol) was added to a stirred suspension of 4-(aminomethyl)-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione hydrochloride (0.6 g, 1.85 mmol) in CH3CN (50 mL). After stirring for 20 min, octyl isocyanate (0.44 g, 2.77 mmol) was added. The mixture was stirred at room temper... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccc2c(c1)C[NH]C2.C1CCNCC1 | null | CC#N | null | 0.333333 | CCCCCCCCN=C=O.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>CC#N>CCCCCCCCNC(=O)NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6b48f824e77147c584c9d7d8b537664f | NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C=NCc1ccccc1>>O=C1CCC(N2C(=O)c3cccc(CNC(=O)NCc4ccccc4)c3C2=O)C(=O)N1 | N12CCCCCC2=NCCC1.Cl.NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.C(C1=CC=CC=C1)N=C=O>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)NCC1=CC=CC=C1)=O)=O | [O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([CH2:14][NH2:15])[c:26]3[C:27]2=[O:28])[C:29](=[O:30])[NH:31]1.[C:16](=[O:17])=[N:18][CH2:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([CH2:14][N... | NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C=NCc1ccccc1 | O=C1CCC(N2C(=O)c3cccc(CNC(=O)NCc4ccccc4)c3C2=O)C(=O)N1 | null | null | CC#N | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C1CCC(N2C(=O)c3cccc(CNC(=O)NCc4ccccc4)c3C2=O)C(=O)N1 | [NH2;D1;+0:1]-[C:2]-[c:3].[O;D1;H0:4]=[C;H0;D2;+0:5]=[N;H0;D2;+0:6]-[C:7]-[c:8]>>[O;D1;H0:4]=[C;H0;D3;+0:5](-[NH;D2;+0:1]-[C:2]-[c:3])-[NH;D2;+0:6]-[C:7]-[c:8] | 54 | [{"value": 54.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)NCC1=CC=CC=C1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)NCC1=CC=CC=C1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | 1,8-Diazabicyclo[5,4,0]undec-7-ene (0.29 g, 1.90 mmol) was added to a stirred suspension of 4-(aminomethyl)-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione hydrochloride (0.6 g, 1.85 mmol) in CH3CN (50 mL). After stirring for 20 min, benzyl isocyanate (0.32 g, 2.41 mmol) was added. The mixture was stirred at room tempe... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | C1CCNCC1.c1ccc2c(c1)C[NH]C2.c1ccccc1 | null | CC#N | null | 0.333333 | NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C=NCc1ccccc1>CC#N>O=C1CCC(N2C(=O)c3cccc(CNC(=O)NCc4ccccc4)c3C2=O)C(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-743e54e682044e569db75cea5c6f0197 | NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C([O-])N(c1ccc([N+](=O)[O-])cc1)C1CC1>>O=C1CCC(N2C(=O)c3cccc(CNC(=O)NC4CC4)c3C2=O)C(=O)N1 | N12CCCCCC2=NCCC1.Cl.NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.[N+](=O)([O-])C1=CC=C(C=C1)N(C([O-])=O)C1CC1>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)NC1CC1)=O)=O | [O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([CH2:14][NH2:15])[c:22]3[C:23]2=[O:24])[C:25](=[O:26])[NH:27]1.O=[N+]([O-])c1ccc([N:18]([C:16]([O-])=[O:17])[CH:19]2[CH2:20][CH2:21]2)cc1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([CH2:14][... | NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C([O-])N(c1ccc([N+](=O)[O-])cc1)C1CC1 | O=C1CCC(N2C(=O)c3cccc(CNC(=O)NC4CC4)c3C2=O)C(=O)N1 | null | null | CC#N | Acylation | OtherReaction | c544444e833963de17b7285ecf254c119edba4524de2ca959e1686976f0aeaf8 | 75a79f455fef00f73470f8263f7f62d9ceebfd06076631fa20de1d0098d3252f | O=C1CCC(N2C(=O)c3cccc(CNC(=O)NC4CC4)c3C2=O)C(=O)N1 | O=[N+](-[O-])-c1:c:c:c(-[N;H0;D3;+0:1](-[C:2]2-[C:3]-[C:4]-2)-[C;H0;D3;+0:5](-[O-])=[O;D1;H0:6]):c:c:1.[NH2;D1;+0:7]-[C:8]-[c:9]>>[O;D1;H0:6]=[C;H0;D3;+0:5](-[NH;D2;+0:7]-[C:8]-[c:9])-[NH;D2;+0:1]-[C:2]1-[C:3]-[C:4]-1 | 77.4 | [{"value": 77.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)NC1CC1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.4, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(=O)NC1CC1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | 1,8-Diazabicyclo[5,4,0]undec-7-ene (0.58 g, 3.81 mmol) was added to a stirred suspension of 4-(aminomethyl)-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione hydrochloride (0.6 g, 1.85 mmol) in CH3CN (50 mL). After stirring for 20 min, 4-nitrophenyl-N-cyclopropylcarbamate (0.41 g, 1.85 mmol) was added. The mixture was st... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic acid.Nitro group.Primary amine | Urea | c1ccccc1 | null | C1CCNCC1.c1ccc2c(c1)C[NH]C2.C1CC1 | HO- | CC#N | null | 0.333333 | NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C([O-])N(c1ccc([N+](=O)[O-])cc1)C1CC1>CC#N>O=C1CCC(N2C(=O)c3cccc(CNC(=O)NC4CC4)c3C2=O)C(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-84a305a299fe4ab280c8b71260983904 | O=C(O)CCCCCNC(=O)OCc1ccccc1.O=S(Cl)Cl>>O=C(Cl)CCCCCNC(=O)OCc1ccccc1 | C(C1=CC=CC=C1)OC(=O)NCCCCCC(=O)O.S(=O)(Cl)Cl>>C(C1=CC=CC=C1)OC(NCCCCCC(=O)Cl)=O | O[C:2](=[O:1])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10](=[O:11])[O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.O=S(Cl)[Cl:3]>>[O:1]=[C:2]([Cl:3])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10](=[O:11])[O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | O=C(O)CCCCCNC(=O)OCc1ccccc1.O=S(Cl)Cl | O=C(Cl)CCCCCNC(=O)OCc1ccccc1 | null | null | null | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccccc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4]-[C:5]>>[C:5]-[C:4]-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3] | null | [] | null | null | null | null | A solution of 6-benzyloxycarbonylamino-hexanoic acid(2.65 g, 10 mmol) in thionyl chloride (15 ml) was heated to reflux 1 h. The reaction mixture was allowed to cool to room temperature and the solvent was evaporated in vacuo to give (5-chlorocarbonyl-pentyl)-carbamic acid benzyl ester as tan oil. The oil was used witho... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccccc1 | HCl | null | null | null | O=C(O)CCCCCNC(=O)OCc1ccccc1.O=S(Cl)Cl>>O=C(Cl)CCCCCNC(=O)OCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-84204a622a124f19a54d145075a274bb | CCOC(C)=O.Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>>O=C1CCC(N2C(=O)c3cccc(NC(=O)CCCCCNC(=O)OCc4ccccc4)c3C2=O)C(=O)N1 | NC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O.C(C)(=O)OCC>>C(C1=CC=CC=C1)OC(NCCCCCC(NC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O)=O)=O | [C:15](=[O:16])([CH3:17])[O:24][CH2:23][CH3:18].[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([NH2:14])[c:33]3[C:34]2=[O:35])[C:36](=[O:37])[NH:38]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([NH:14][C:15](=[O:16])[CH2:17][CH2:18][CH2:1... | CCOC(C)=O.Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | O=C1CCC(N2C(=O)c3cccc(NC(=O)CCCCCNC(=O)OCc4ccccc4)c3C2=O)C(=O)N1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 90aca4309df16b8d5f9cb814b61709c81093489c91daaacbe415864ca5ee122d | 5c5ee92bf076734e649de480ab6e1cf58cef33f431146f256387e8f32604ff7f | O=C1CCC(N2C(=O)c3cccc(NC(=O)CCCCCNC(=O)OCc4ccccc4)c3C2=O)C(=O)N1 | [#7:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5](-[NH2;D1;+0:6]):[c:7].[CH3;D1;+0:8]-[C;H0;D3;+0:9](=[O;D1;H0:10])-[O;H0;D2;+0:11]-[CH2;D2;+0:12]-[CH3;D1;+0:13]>>[#7:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5](-[NH;D2;+0:6]-[C;H0;D3;+0:9](=[O;D1;H0:10])-[CH2;D2;+0:8]-[CH2;D2;+0:13]-[C:14]-[C:15]-[C:16]-[#7:17]-[C;H0;D3;+0:12](=[O;H0;D1;+... | 48 | [{"value": 48.0, "product": "C(C1=CC=CC=C1)OC(NCCCCCC(NC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 6-benzyloxycarbonylamino-hexanoic acid(2.65 g, 10 mmol) in thionyl chloride (15 ml) was heated to reflux 1 h. The reaction mixture was allowed to cool to room temperature and the solvent was evaporated in vacuo to give (5-chlorocarbonyl-pentyl)-carbamic acid benzyl ester as tan oil. The oil was used witho... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Carbamic ester.Ether.Secondary amide | null | c1ccccc1 | C1CCNCC1.c1ccc2c(c1)C[NH]C2.c1ccccc1 | Other | null | null | null | CCOC(C)=O.Nc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>>O=C1CCC(N2C(=O)c3cccc(NC(=O)CCCCCNC(=O)OCc4ccccc4)c3C2=O)C(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ac8c6775fdd64d5d84b5033ff65cb742 | CC1(N2C(=O)c3cccc(N)c3C2=O)CCC(=O)NC1=O.O=C(Cl)c1cccc(Cl)c1>>CC1(N2C(=O)c3cccc(NC(=O)c4cccc(Cl)c4)c3C2=O)CCC(=O)NC1=O | NC1=C2C(N(C(C2=CC=C1)=O)C1(C(NC(CC1)=O)=O)C)=O.ClC=1C=C(C(=O)Cl)C=CC1.CO>>ClC=1C=C(C(=O)NC2=C3C(N(C(C3=CC=C2)=O)C2(C(NC(CC2)=O)=O)C)=O)C=CC1 | [CH3:1][C:2]1([N:3]2[C:4](=[O:5])[c:6]3[cH:7][cH:8][cH:9][c:10]([NH2:11])[c:21]3[C:22]2=[O:23])[CH2:24][CH2:25][C:26](=[O:27])[NH:28][C:29]1=[O:30].Cl[C:12](=[O:13])[c:14]1[cH:15][cH:16][cH:17][c:18]([Cl:19])[cH:20]1>>[CH3:1][C:2]1([N:3]2[C:4](=[O:5])[c:6]3[cH:7][cH:8][cH:9][c:10]([NH:11][C:12](=[O:13])[c:14]4[cH:15][c... | CC1(N2C(=O)c3cccc(N)c3C2=O)CCC(=O)NC1=O.O=C(Cl)c1cccc(Cl)c1 | CC1(N2C(=O)c3cccc(NC(=O)c4cccc(Cl)c4)c3C2=O)CCC(=O)NC1=O | null | null | C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CCC(N2C(=O)c3cccc(NC(=O)c4ccccc4)c3C2=O)C(=O)N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[NH2;D1;+0:11]):[c:12]>>[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]):[c:12] | 73.8 | [{"value": 73.0, "product": "ClC=1C=C(C(=O)NC2=C3C(N(C(C3=CC=C2)=O)C2(C(NC(CC2)=O)=O)C)=O)C=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.8, "product": "ClC=1C=C(C(=O)NC2=C3C(N(C(C3=CC=C2)=O)C2(C(NC(CC2)=O)=O)C)=O)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a suspension of 4-amino-2-(3-methyl-2,6-dioxo-piperidin-3-yl)-isoindole-1,3-dione (0.10 g, 0.35 mmol) in THF (15 ml) was added 3-chlorobenzoyl chloride (0.12 g, 0.70 mmol) The mixture was heated to reflux for 18 h. The reaction mixture was allowed to cool and to the solution was added methanol (2 ml). The reaction m... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2c(c1)C[NH]C2.c1ccccc1.C1CCNCC1 | HCl | C1CCOC1 | null | 0.25 | CC1(N2C(=O)c3cccc(N)c3C2=O)CCC(=O)NC1=O.O=C(Cl)c1cccc(Cl)c1>C1CCOC1>CC1(N2C(=O)c3cccc(NC(=O)c4cccc(Cl)c4)c3C2=O)CCC(=O)NC1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4f70795a6c464edfa332ca666287bed9 | CC1(N2C(=O)c3cccc(N)c3C2=O)CCC(=O)NC1=O.CCC(=O)Cl>>CCC(=O)Nc1cccc2c1C(=O)N(C1(C)CCC(=O)NC1=O)C2=O | NC1=C2C(N(C(C2=CC=C1)=O)C1(C(NC(CC1)=O)=O)C)=O.C(CC)(=O)Cl.CO>>CC1(C(NC(CC1)=O)=O)N1C(C2=CC=CC(=C2C1=O)NC(CC)=O)=O | [NH2:5][c:6]1[cH:7][cH:8][cH:9][c:10]2[c:11]1[C:12](=[O:13])[N:14]([C:15]1([CH3:16])[CH2:17][CH2:18][C:19](=[O:20])[NH:21][C:22]1=[O:23])[C:24]2=[O:25].Cl[C:3]([CH2:2][CH3:1])=[O:4]>>[CH3:1][CH2:2][C:3](=[O:4])[NH:5][c:6]1[cH:7][cH:8][cH:9][c:10]2[c:11]1[C:12](=[O:13])[N:14]([C:15]1([CH3:16])[CH2:17][CH2:18][C:19](=[O:... | CC1(N2C(=O)c3cccc(N)c3C2=O)CCC(=O)NC1=O.CCC(=O)Cl | CCC(=O)Nc1cccc2c1C(=O)N(C1(C)CCC(=O)NC1=O)C2=O | null | null | C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C;D1;H3:4].[#7:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](-[NH2;D1;+0:10]):[c:11]>>[#7:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C;D1;H3:4]):[c:11] | 63 | [{"value": 63.0, "product": "CC1(C(NC(CC1)=O)=O)N1C(C2=CC=CC(=C2C1=O)NC(CC)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.3, "product": "CC1(C(NC(CC1)=O)=O)N1C(C2=CC=CC(=C2C1=O)NC(CC)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a suspension of 4-amino-2-(3-methyl-2,6-dioxo-piperidin-3-yl)-isoindole-1,3-dione (0.10 g, 0.35 mmol) in THF (15 ml) was added propionyl chloride (0.07 g, 0.70 mmol). The mixture was heated to reflux for 18 h. The reaction mixture was allowed to cool and to the solution was added methanol (2 ml). The reaction mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2c(c1)C[NH]C2.C1CCNCC1 | HCl | C1CCOC1 | null | 0.25 | CC1(N2C(=O)c3cccc(N)c3C2=O)CCC(=O)NC1=O.CCC(=O)Cl>C1CCOC1>CCC(=O)Nc1cccc2c1C(=O)N(C1(C)CCC(=O)NC1=O)C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f38173b9cff244909a2e1e470e0343b6 | COC(=O)c1cccc(NCc2ccc(C)o2)c1C(=O)OC>>Cc1ccc(CNc2cccc(C(=O)O)c2C(=O)O)o1 | COC(C=1C(C(=O)OC)=C(C=CC1)NCC=1OC(=CC1)C)=O.COCCNC1=C(C(C(=O)O)=CC=C1)C(=O)O>>CC1=CC=C(O1)CNC1=C(C(C(=O)O)=CC=C1)C(=O)O | C[O:15][C:13]([c:12]1[cH:11][cH:10][cH:9][c:8]([NH:7][CH2:6][c:5]2[cH:4][cH:3][c:2]([CH3:1])[o:20]2)[c:16]1[C:17](=[O:18])[O:19]C)=[O:14]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][NH:7][c:8]2[cH:9][cH:10][cH:11][c:12]([C:13](=[O:14])[OH:15])[c:16]2[C:17](=[O:18])[OH:19])[o:20]1 | COC(=O)c1cccc(NCc2ccc(C)o2)c1C(=O)OC | Cc1ccc(CNc2cccc(C(=O)O)c2C(=O)O)o1 | null | null | null | Deprotection | OtherReaction | 6e62db7aac546f574bcfb83067ba8906c30fcbfedfc37aa16b5eaad33833f45a | ed5fed81ba501ef41c88831ec6b9463b899bfdd0815c4145ae51c79addb226d0 | c1ccc(NCc2ccco2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4]:[c:5]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8] | null | [] | null | null | null | null | 3-[(5-Methyl-furan-2-ylmethyl)-amino]-phthalic acid dimethyl ester (5 mmol) was treated in the same manner as described above for the synthesis of 3-(2-methoxy-ethylamino)-phthalic acid. The product of the reaction, which contained a mixture of diacid and monomethyl esters, was used without further purification.
Condit... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Carboxylic acid.Carboxylic acid | null | null | c1ccoc1.c1ccccc1 | Other | null | null | null | COC(=O)c1cccc(NCc2ccc(C)o2)c1C(=O)OC>>Cc1ccc(CNc2cccc(C(=O)O)c2C(=O)O)o1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dccebd22b3ec4362a33423fcea0a16f0 | COCCNc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.Cc1ccc(CNc2cccc(C(=O)O)c2C(=O)O)o1>>Cc1ccc(CNc2cccc3c2C(=O)N(C2CCC(=O)NC2=O)C3=O)o1 | CC1=CC=C(O1)CNC1=C(C(C(=O)O)=CC=C1)C(=O)O.O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NCCOC)=O)=O>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NCC=1OC(=CC1)C)=O)=O | COCCNc1cccc2c1[C:14](=[O:15])[N:16]([CH:17]1[CH2:18][CH2:19][C:20](=[O:21])[NH:22][C:23]1=[O:24])[C:25]2=[O:26].O=C(O)[c:12]1[cH:11][cH:10][cH:9][c:8]([NH:7][CH2:6][c:5]2[cH:4][cH:3][c:2]([CH3:1])[o:27]2)[c:13]1C(=O)O>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][NH:7][c:8]2[cH:9][cH:10][cH:11][c:12]3[c:13]2[C:14](=[O:15])[N... | COCCNc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.Cc1ccc(CNc2cccc(C(=O)O)c2C(=O)O)o1 | Cc1ccc(CNc2cccc3c2C(=O)N(C2CCC(=O)NC2=O)C3=O)o1 | null | null | null | C-C Coupling | OtherReaction | e01b406c4bd6fd113e0f2e1f0fbdfa1994fad43c14b9a159b5c537e52be3a29d | 47dba274a38dfe0abc81230fe8a80653f556b2eb304748f9abffbd031c5d793d | O=C1CCC(N2C(=O)c3cccc(NCc4ccco4)c3C2=O)C(=O)N1 | C-O-C-C-N-c1:c:c:c:c2:c:1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C:4]-[C:5](=[O;D1;H0:6])-[#7:7])-[C;H0;D3;+0:8]-2=[O;D1;H0:9].O-C(=O)-[c;H0;D3;+0:10]1:[c:11]:[c:12]:[c:13]:[c:14](-[#7:15]):[c;H0;D3;+0:16]:1-C(-O)=O>>[#7:7]-[C:5](=[O;D1;H0:6])-[C:4]-[#7:3]1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:16]2:[c:14](-[#7:15]):... | 20 | [{"value": 20.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NCC=1OC(=CC1)C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-[(5-Methyl-furan-2-ylmethyl)-amino]-phthalic acid (5 mmol) was treated in the same manner as described above for the synthesis of 2-(2,6-dioxo-piperidin-3-yl)-4-(2-methoxy-ethylamino)-isoindole-1,3-dione. The residue was purified by preparative HPLC (Symmetry C18, isocratic, 35/65 acetonitrile/water) to give 0.31 g (... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Ether.Substituted dicarboximide.Secondary amine | Substituted dicarboximide | c1ccc2c(c1)C[NH]C2.c1ccccc1 | c1ccc2c(c1)C[NH]C2 | c1ccoc1.c1ccc2c(c1)C[NH]C2.C1CCNCC1 | HO- | null | null | null | COCCNc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.Cc1ccc(CNc2cccc(C(=O)O)c2C(=O)O)o1>>Cc1ccc(CNc2cccc3c2C(=O)N(C2CCC(=O)NC2=O)C3=O)o1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e18948dc548b449a94049ddf9b9c4905 | CCCCCNc1cccc(C(=O)OC)c1C(=O)OC.O=Cc1ccc(CO)o1>>COC(=O)c1cccc(NCc2ccc(CO)o2)c1C(=O)OC | OCC1=CC=C(O1)C=O.COC(C=1C(C(=O)OC)=C(C=CC1)NCCCCC)=O>>COC(C=1C(C(=O)OC)=C(C=CC1)NCC=1OC(=CC1)CO)=O | CCCCC[NH:10][c:9]1[cH:8][cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:19]1[C:20](=[O:21])[O:22][CH3:23].O=[CH:11][c:12]1[cH:13][cH:14][c:15]([CH2:16][OH:17])[o:18]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([NH:10][CH2:11][c:12]2[cH:13][cH:14][c:15]([CH2:16][OH:17])[o:18]2)[c:19]1[C:20](=[O:21])[O:22][CH... | CCCCCNc1cccc(C(=O)OC)c1C(=O)OC.O=Cc1ccc(CO)o1 | COC(=O)c1cccc(NCc2ccc(CO)o2)c1C(=O)OC | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | fc9422fe50863a8e7b22fcc145dd01d982e3de4e7dec633bf5d0e217ba35cfe6 | 7adcd96acc7986e995a59780d11a29072ec6cdad41c8d7f65df5f25f2d933fc4 | c1ccc(NCc2ccco2)cc1 | C-C-C-C-C-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](-[#8:6])=[O;D1;H0:7].O=[CH;D2;+0:8]-[c:9](:[c:10]):[#8;a:11]:[c:12]>>[#8:6]-[C:5](=[O;D1;H0:7])-[c:4]:[c:2](-[NH;D2;+0:1]-[CH2;D2;+0:8]-[c:9](:[c:10]):[#8;a:11]:[c:12]):[c:3] | 76 | [{"value": 76.0, "product": "COC(C=1C(C(=O)OC)=C(C=CC1)NCC=1OC(=CC1)CO)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 5-Hydroxymethyl-furan-2-carbaldehyde (0.95 ml, 7.5 mmol) was treated in the same manner as described above for the synthesis of 3-pentylamino-phthalic acid dimethyl ester. The residue (oil) was purified by chromatography (SiO2, 40/60 ethyl acetate/hexanes) to give 0.97 g (76%) of yellow oil: 1H NMR (CDCl3) δ 7.35–7.27 ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Secondary amine | null | null | c1ccccc1.c1ccoc1 | HO- | null | null | null | CCCCCNc1cccc(C(=O)OC)c1C(=O)OC.O=Cc1ccc(CO)o1>>COC(=O)c1cccc(NCc2ccc(CO)o2)c1C(=O)OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-22f8c12012f2426eaa164d66c497f0db | COC(=O)c1cccc(NCc2ccc(CO)o2)c1C(=O)OC>>O=C(O)c1cccc(NCc2ccc(CO)o2)c1C(=O)O | COC(C=1C(C(=O)OC)=C(C=CC1)NCC=1OC(=CC1)CO)=O.COCCNC1=C(C(C(=O)O)=CC=C1)C(=O)O>>OCC1=CC=C(O1)CNC1=C(C(C(=O)O)=CC=C1)C(=O)O | C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][cH:7][c:8]([NH:9][CH2:10][c:11]2[cH:12][cH:13][c:14]([CH2:15][OH:16])[o:17]2)[c:18]1[C:19](=[O:20])[O:21]C>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([NH:9][CH2:10][c:11]2[cH:12][cH:13][c:14]([CH2:15][OH:16])[o:17]2)[c:18]1[C:19](=[O:20])[OH:21] | COC(=O)c1cccc(NCc2ccc(CO)o2)c1C(=O)OC | O=C(O)c1cccc(NCc2ccc(CO)o2)c1C(=O)O | null | null | null | Deprotection | OtherReaction | 6e62db7aac546f574bcfb83067ba8906c30fcbfedfc37aa16b5eaad33833f45a | ed5fed81ba501ef41c88831ec6b9463b899bfdd0815c4145ae51c79addb226d0 | c1ccc(NCc2ccco2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C>>[O;D1;H0:7]=[C:6](-[OH;D1;+0:8])-[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | null | null | 3-[(5-Hydroxymethyl-furan-2-ylmethyl)-amino]-phthalic acid dimethyl ester (0.97 g, 3.04 mmol) was treated in the same manner as described above for the synthesis of 3-(2-methoxy-ethylamino)-phthalic acid. The product of the reaction, which contained a mixture of diacid and monomethyl esters, was used without further pu... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Carboxylic acid.Carboxylic acid | null | null | c1ccccc1.c1ccoc1 | Other | null | null | null | COC(=O)c1cccc(NCc2ccc(CO)o2)c1C(=O)OC>>O=C(O)c1cccc(NCc2ccc(CO)o2)c1C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a8a0470126654e44898941dbb98e2029 | COCCNc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(O)c1cccc(NCc2ccc(CO)o2)c1C(=O)O>>O=C1CCC(N2C(=O)c3cccc(NCc4ccc(CO)o4)c3C2=O)C(=O)N1 | OCC1=CC=C(O1)CNC1=C(C(C(=O)O)=CC=C1)C(=O)O.O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NCCOC)=O)=O>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NCC=1OC(=CC1)CO)=O)=O | COCCNc1cccc2c1C(=O)[N:6]([CH:5]1[CH2:4][CH2:3][C:2](=[O:1])[NH:28][C:26]1=[O:27])[C:24]2=[O:25].O=C(O)[c:23]1[c:9]([C:7](O)=[O:8])[cH:10][cH:11][cH:12][c:13]1[NH:14][CH2:15][c:16]1[cH:17][cH:18][c:19]([CH2:20][OH:21])[o:22]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([NH:14][... | COCCNc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(O)c1cccc(NCc2ccc(CO)o2)c1C(=O)O | O=C1CCC(N2C(=O)c3cccc(NCc4ccc(CO)o4)c3C2=O)C(=O)N1 | null | null | null | Acylation | OtherReaction | 7cf398b8b4a806b284dc2a9bb920aa585f40dfdbdf81f271703b70d32d9c1d23 | b34812891aa4b14ae9732f1e94ebf3683240312475d27c2db2c5e5699f26030f | O=C1CCC(N2C(=O)c3cccc(NCc4ccco4)c3C2=O)C(=O)N1 | C-O-C-C-N-c1:c:c:c:c2:c:1-C(=O)-[N;H0;D3;+0:1](-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[#7:6]-[C:7]=[O;D1;H0:8])-[C;H0;D3;+0:9]-2=[O;D1;H0:10].O-C(=O)-[c;H0;D3;+0:11](:[c:12](-[#7:13]):[c:14]):[c:15](-[C;H0;D3;+0:16](-O)=[O;D1;H0:17]):[c:18]>>[#7:13]-[c:12](:[c:14]):[c;H0;D3;+0:11]1:[c:15](:[c:18])-[C;H0;D3;+0:16](=[O;D1;H0... | null | [] | null | null | null | null | 3-[(5-Hydroxymethyl-furan-2-ylmethyl)-amino]-phthalic acid (3.04 mmol) was treated in the same manner as described above for the synthesis of 2-(2,6-Dioxo-piperidin-3-yl)-4-(2-methoxy-ethylamino)-isoindole-1,3-dione. The solid yellow residue was purified by chromatography (SiO2, 60% ethyl acetate/hexanes) to give 0.40 ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Ether.Substituted dicarboximide.Secondary amine | Substituted dicarboximide | c1ccc2c(c1)C[NH]C2.c1ccccc1 | c1ccc2c(c1)C[NH]C2 | C1CCNCC1.c1ccc2c(c1)C[NH]C2.c1ccoc1 | HO- | null | null | null | COCCNc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(O)c1cccc(NCc2ccc(CO)o2)c1C(=O)O>>O=C1CCC(N2C(=O)c3cccc(NCc4ccc(CO)o4)c3C2=O)C(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6e253cf5fc8347139a0320e75ea0a5b6 | CCCCCNc1cccc(C(=O)OC)c1C(=O)OC.O=Cc1cccs1>>COC(=O)c1cccc(NCc2cccs2)c1C(=O)OC | S1C(=CC=C1)C=O.COC(C=1C(C(=O)OC)=C(C=CC1)NCCCCC)=O>>COC(C=1C(C(=O)OC)=C(C=CC1)NCC=1SC=CC1)=O | CCCCC[NH:10][c:9]1[cH:8][cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:17]1[C:18](=[O:19])[O:20][CH3:21].O=[CH:11][c:12]1[cH:13][cH:14][cH:15][s:16]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([NH:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][s:16]2)[c:17]1[C:18](=[O:19])[O:20][CH3:21] | CCCCCNc1cccc(C(=O)OC)c1C(=O)OC.O=Cc1cccs1 | COC(=O)c1cccc(NCc2cccs2)c1C(=O)OC | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | fc9422fe50863a8e7b22fcc145dd01d982e3de4e7dec633bf5d0e217ba35cfe6 | 7adcd96acc7986e995a59780d11a29072ec6cdad41c8d7f65df5f25f2d933fc4 | c1ccc(NCc2cccs2)cc1 | C-C-C-C-C-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](-[#8:6])=[O;D1;H0:7].O=[CH;D2;+0:8]-[c:9](:[c:10]):[#16;a:11]:[c:12]>>[#8:6]-[C:5](=[O;D1;H0:7])-[c:4]:[c:2](-[NH;D2;+0:1]-[CH2;D2;+0:8]-[c:9](:[c:10]):[#16;a:11]:[c:12]):[c:3] | 58 | [{"value": 58.0, "product": "COC(C=1C(C(=O)OC)=C(C=CC1)NCC=1SC=CC1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Thiophenecarboxaldehyde (1.12 g, 10 mmol) was treated in the same manner as described above for the synthesis of 3-pentylamino-phthalic acid dimethyl ester. The residue (oil) was purified by preparative HPLC (Symmetry C18, isocratic, 45% acetonitrile/water) to give 0.88 g (58%) of yellow oil: 1H NMR (CDCl3) δ 7.38–7.... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Secondary amine | null | null | c1ccccc1.c1ccsc1 | HO- | null | null | null | CCCCCNc1cccc(C(=O)OC)c1C(=O)OC.O=Cc1cccs1>>COC(=O)c1cccc(NCc2cccs2)c1C(=O)OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-46080862d7464522ad108ad03c61ee7c | COC(=O)c1cccc(NCc2cccs2)c1C(=O)OC>>O=C(O)c1cccc(NCc2cccs2)c1C(=O)O | COC(C=1C(C(=O)OC)=C(C=CC1)NCC=1SC=CC1)=O.COCCNC1=C(C(C(=O)O)=CC=C1)C(=O)O>>S1C(=CC=C1)CNC1=C(C(C(=O)O)=CC=C1)C(=O)O | C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][cH:7][c:8]([NH:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][s:15]2)[c:16]1[C:17](=[O:18])[O:19]C>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([NH:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][s:15]2)[c:16]1[C:17](=[O:18])[OH:19] | COC(=O)c1cccc(NCc2cccs2)c1C(=O)OC | O=C(O)c1cccc(NCc2cccs2)c1C(=O)O | null | null | null | Deprotection | OtherReaction | 6e62db7aac546f574bcfb83067ba8906c30fcbfedfc37aa16b5eaad33833f45a | ed5fed81ba501ef41c88831ec6b9463b899bfdd0815c4145ae51c79addb226d0 | c1ccc(NCc2cccs2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4]:[c:5]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8] | null | [] | null | null | null | null | 3-[(Thiophen-2-ylmethyl)-amino]-phthalic acid dimethyl ester (0.88 g, 2.88 mmol) was treated in the same manner as described above for the synthesis 3-(2-methoxy-ethylamino)-phthalic acid. The product of the reaction, which contained a mixture of diacid and monomethyl esters, was used without further purification.
Cond... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Carboxylic acid.Carboxylic acid | null | null | c1ccccc1.c1ccsc1 | Other | null | null | null | COC(=O)c1cccc(NCc2cccs2)c1C(=O)OC>>O=C(O)c1cccc(NCc2cccs2)c1C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8866f453d3d34b508420d63f9da1b629 | COCCNc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(O)c1cccc(NCc2cccs2)c1C(=O)O>>O=C1CCC(N2C(=O)c3cccc(NCc4cccs4)c3C2=O)C(=O)N1 | S1C(=CC=C1)CNC1=C(C(C(=O)O)=CC=C1)C(=O)O.O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NCCOC)=O)=O>>O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NCC=1SC=CC1)=O)=O | COCCNc1cccc2c1C(=O)[N:6]([CH:5]1[CH2:4][CH2:3][C:2](=[O:1])[NH:26][C:24]1=[O:25])C2=O.O[C:7](=[O:8])[c:9]1[cH:10][cH:11][cH:12][c:13]([NH:14][CH2:15][c:16]2[cH:17][cH:18][cH:19][s:20]2)[c:21]1[C:22](O)=[O:23]>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([NH:14][CH2:15][c:16]4[c... | COCCNc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(O)c1cccc(NCc2cccs2)c1C(=O)O | O=C1CCC(N2C(=O)c3cccc(NCc4cccs4)c3C2=O)C(=O)N1 | null | null | null | Acylation | OtherReaction | 5b97b2716363c7d076f525a81453119f9bd234e3df60a591fce8a07715532192 | b34812891aa4b14ae9732f1e94ebf3683240312475d27c2db2c5e5699f26030f | O=C1CCC(N2C(=O)c3cccc(NCc4cccs4)c3C2=O)C(=O)N1 | C-O-C-C-N-c1:c:c:c:c2:c:1-C(=O)-[N;H0;D3;+0:1](-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[#7:6]-[C:7]=[O;D1;H0:8])-C-2=O.O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13](-[C;H0;D3;+0:14](-O)=[O;D1;H0:15]):[c:16]>>[C:3]-[C:2](-[N;H0;D3;+0:1]1-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13](:[c:16])-[C;H0;D3;+0:14]-1... | 29 | [{"value": 29.0, "product": "O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NCC=1SC=CC1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-[(Thiophen-2-ylmethyl)-amino]-phthalic acid (2.88 mmol) was treated in the same manner as described above for the synthesis of 2-(2,6-dioxo-piperidin-3-yl)-4-(2-methoxy-ethylamino)-isoindole-1,3-dione. The solid yellow residue was purified by preparative HPLC (Symmetry C18, isocratic, 35% acetonitrile/water) to give ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Ether.Substituted dicarboximide.Secondary amine | Substituted dicarboximide | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | C1CCNCC1.c1ccc2c(c1)C[NH]C2.c1ccsc1 | HO- | null | null | null | COCCNc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(O)c1cccc(NCc2cccs2)c1C(=O)O>>O=C1CCC(N2C(=O)c3cccc(NCc4cccs4)c3C2=O)C(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f6f26e92084842f196349d3229d1ff9b | COC(=O)c1cccc(NCc2cccc(Cl)c2)c1C(=O)OC>>O=C(O)c1cccc(NCc2cccc(Cl)c2)c1C(=O)O | COC(C=1C(C(=O)OC)=C(C=CC1)NCC1=CC(=CC=C1)Cl)=O.COCCNC1=C(C(C(=O)O)=CC=C1)C(=O)O>>ClC=1C=C(CNC2=C(C(C(=O)O)=CC=C2)C(=O)O)C=CC1 | C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][cH:7][c:8]([NH:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][c:15]([Cl:16])[cH:17]2)[c:18]1[C:19](=[O:20])[O:21]C>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([NH:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][c:15]([Cl:16])[cH:17]2)[c:18]1[C:19](=[O:20])[OH:21] | COC(=O)c1cccc(NCc2cccc(Cl)c2)c1C(=O)OC | O=C(O)c1cccc(NCc2cccc(Cl)c2)c1C(=O)O | null | null | null | Deprotection | OtherReaction | 6e62db7aac546f574bcfb83067ba8906c30fcbfedfc37aa16b5eaad33833f45a | ed5fed81ba501ef41c88831ec6b9463b899bfdd0815c4145ae51c79addb226d0 | c1ccc(CNc2ccccc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C>>[O;D1;H0:7]=[C:6](-[OH;D1;+0:8])-[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | null | null | 3-(3-Chloro-benzylamino)-phthalic acid dimethyl ester (1.61 g, 4.8 mmol) was treated in the same manner as described above for the synthesis of 3-(2-methoxy-ethylamino)-phthalic acid. The product of the reaction, which contained a mixture of diacid and monomethyl esters, was used without further purification.
Condition... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Carboxylic acid.Carboxylic acid | null | null | c1ccccc1.c1ccccc1 | Other | null | null | null | COC(=O)c1cccc(NCc2cccc(Cl)c2)c1C(=O)OC>>O=C(O)c1cccc(NCc2cccc(Cl)c2)c1C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c42f2eb55b2846b9a326ebf626462b57 | COCCNc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(O)c1cccc(NCc2cccc(Cl)c2)c1C(=O)O>>O=C1CCC(N2C(=O)c3cccc(NCc4cccc(Cl)c4)c3C2=O)C(=O)N1 | ClC=1C=C(CNC2=C(C(C(=O)O)=CC=C2)C(=O)O)C=CC1.O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)NCCOC)=O)=O>>ClC=1C=C(CNC2=C3C(N(C(C3=CC=C2)=O)C2C(NC(CC2)=O)=O)=O)C=CC1 | COCCNc1cccc2c1C(=O)[N:6]([CH:5]1[CH2:4][CH2:3][C:2](=[O:1])[NH:28][C:26]1=[O:27])C2=O.O[C:7](=[O:8])[c:9]1[cH:10][cH:11][cH:12][c:13]([NH:14][CH2:15][c:16]2[cH:17][cH:18][cH:19][c:20]([Cl:21])[cH:22]2)[c:23]1[C:24](O)=[O:25]>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([NH:14][... | COCCNc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(O)c1cccc(NCc2cccc(Cl)c2)c1C(=O)O | O=C1CCC(N2C(=O)c3cccc(NCc4cccc(Cl)c4)c3C2=O)C(=O)N1 | null | null | C(C)OCC | Acylation | OtherReaction | 5b97b2716363c7d076f525a81453119f9bd234e3df60a591fce8a07715532192 | b34812891aa4b14ae9732f1e94ebf3683240312475d27c2db2c5e5699f26030f | O=C1CCC(N2C(=O)c3cccc(NCc4ccccc4)c3C2=O)C(=O)N1 | C-O-C-C-N-c1:c:c:c:c2:c:1-C(=O)-[N;H0;D3;+0:1](-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[#7:6]-[C:7]=[O;D1;H0:8])-C-2=O.O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13](-[C;H0;D3;+0:14](-O)=[O;D1;H0:15]):[c:16]>>[C:3]-[C:2](-[N;H0;D3;+0:1]1-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13](:[c:16])-[C;H0;D3;+0:14]-1... | 89 | [{"value": 89.0, "product": "ClC=1C=C(CNC2=C3C(N(C(C3=CC=C2)=O)C2C(NC(CC2)=O)=O)=O)C=CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(3-Chloro-benzylamino)-phthalic acid (4.8 mmol) was treated in the same manner as described above for the synthesis of 2-(2,6-dioxo-piperidin-3-yl)-4-(2-methoxy-ethylamino)-isoindole-1,3-dione. The solid yellow residue was slurried in diethyl ether (30 ml) for 18 h and filtered to give 1.42 g (89%) of product as a ye... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Ether.Substituted dicarboximide.Secondary amine | Substituted dicarboximide | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | C1CCNCC1.c1ccc2c(c1)C[NH]C2.c1ccccc1 | HO- | C(C)OCC | null | null | COCCNc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(O)c1cccc(NCc2cccc(Cl)c2)c1C(=O)O>C(C)OCC>O=C1CCC(N2C(=O)c3cccc(NCc4cccc(Cl)c4)c3C2=O)C(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-37c29cf1922e4917b5f0fcc35c109295 | CCCCCNc1cccc(C(=O)OC)c1C(=O)OC.O=Cc1cccnc1>>COC(=O)c1cccc(NCc2cccnc2)c1C(=O)OC | N1=CC(=CC=C1)C=O.COC(C=1C(C(=O)OC)=C(C=CC1)NCCCCC)=O>>COC(C=1C(C(=O)OC)=C(C=CC1)NCC=1C=NC=CC1)=O | CCCCC[NH:10][c:9]1[cH:8][cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:18]1[C:19](=[O:20])[O:21][CH3:22].O=[CH:11][c:12]1[cH:13][cH:14][cH:15][n:16][cH:17]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([NH:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][n:16][cH:17]2)[c:18]1[C:19](=[O:20])[O:21][CH3:22] | CCCCCNc1cccc(C(=O)OC)c1C(=O)OC.O=Cc1cccnc1 | COC(=O)c1cccc(NCc2cccnc2)c1C(=O)OC | null | null | C(C)OCC | Heteroatom Alkylation and Arylation | OtherReaction | fc9422fe50863a8e7b22fcc145dd01d982e3de4e7dec633bf5d0e217ba35cfe6 | 7adcd96acc7986e995a59780d11a29072ec6cdad41c8d7f65df5f25f2d933fc4 | c1ccc(NCc2cccnc2)cc1 | C-C-C-C-C-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](-[#8:6])=[O;D1;H0:7].O=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]:[#7;a:12]:[c:13]>>[#8:6]-[C:5](=[O;D1;H0:7])-[c:4]:[c:2](-[NH;D2;+0:1]-[CH2;D2;+0:8]-[c:9](:[c:10]):[c:11]:[#7;a:12]:[c:13]):[c:3] | 61 | [{"value": 61.0, "product": "COC(C=1C(C(=O)OC)=C(C=CC1)NCC=1C=NC=CC1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-Pyridinecarboxaldehyde (0.94 ml, 10 mmol) was treated in the same manner as described above for the synthesis of 3-pentylamino-phthalic acid dimethyl ester. After removal of pyridine the residue was dissolved in methylene chloride (100 ml) and washed with water (2×100 ml), saturated NaHCO3 (2×100 ml), brine (1×100 ml... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Secondary amine | null | null | c1ccccc1.c1ccncc1 | HO- | C(C)OCC | null | null | CCCCCNc1cccc(C(=O)OC)c1C(=O)OC.O=Cc1cccnc1>C(C)OCC>COC(=O)c1cccc(NCc2cccnc2)c1C(=O)OC |
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