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-ac312bfa6c2142b1b46f1ac6eceb4ca3 | CNC(=O)C(Cc1ccc2ccccc2c1)N1CCN(C(=O)C(Cc2ccc(F)cc2)NC(=O)C(Cc2ccccc2O)NC(C)=O)C(CCOC(C)=O)C1>>CNC(=O)C(Cc1ccc2ccccc2c1)N1CCN(C(=O)C(Cc2ccc(F)cc2)NC(=O)C(Cc2ccc(O)cc2)NC(C)=O)C(CCO)C1 | C(C)(=O)NC(C(=O)NC(C(=O)N1C(CN(CC1)C(CC1=CC2=CC=CC=C2C=C1)C(NC)=O)CCOC(C)=O)CC1=CC=C(C=C1)F)CC1=C(C=CC=C1)O.O([Na])C>>C(C)(=O)NC(C(=O)NC(C(=O)N1C(CN(CC1)C(C(=O)NC)CC1=CC2=CC=CC=C2C=C1)CCO)CC1=CC=C(C=C1)F)CC1=CC=C(C=C1)O | CC(=O)[O:51][CH2:50][CH2:49][CH:48]1[N:20]([C:21](=[O:22])[CH:23]([CH2:24][c:25]2[cH:26][cH:27][c:28]([F:29])[cH:30][cH:31]2)[NH:32][C:33](=[O:34])[CH:35]([CH2:36][c:37]2[cH:38][cH:43][cH:42][cH:39][c:40]2[OH:41])[NH:44][C:45]([CH3:46])=[O:47])[CH2:19][CH2:18][N:17]([CH:5]([C:3]([NH:2][CH3:1])=[O:4])[CH2:6][c:7]2[cH:8]... | CNC(=O)C(Cc1ccc2ccccc2c1)N1CCN(C(=O)C(Cc2ccc(F)cc2)NC(=O)C(Cc2ccccc2O)NC(C)=O)C(CCOC(C)=O)C1 | CNC(=O)C(Cc1ccc2ccccc2c1)N1CCN(C(=O)C(Cc2ccc(F)cc2)NC(=O)C(Cc2ccc(O)cc2)NC(C)=O)C(CCO)C1 | null | null | CO | Miscellaneous | OtherReaction | 822ce7a8802b4e3de0199bd97723dbd37cf58fd9528caf5cdc8b7b00046006b4 | 08ad6b9f64c9b6b06f2b8e1ab38c37484fe57906caabed42f3d89408c0528a2f | O=C(CCc1ccccc1)NC(Cc1ccccc1)C(=O)N1CCN(CCc2ccc3ccccc3c2)CC1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[C:3].[#7:4]-[C:5](=[O;D1;H0:6])-[C:7]-[C:8]-[c;H0;D3;+0:9]1:[cH;D2;+0:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:[cH;D2;+0:13]:[c;H0;D3;+0:14]:1-[O;D1;H1:15]>>[#7:4]-[C:5](=[O;D1;H0:6])-[C:7]-[C:8]-[c;H0;D3;+0:9]1:[cH;D2;+0:10]:[cH;D2;+0:13]:[c;H0;D3;+0:14](-[O;D1;H1:15]):[cH;D2;+0:12]:[cH;D2;+0:11]:... | null | [] | null | null | 8 | HOUR | To a solution acetic acid 2-[1-{2-[2-acetylamino-3-(hydroxyphenyl)propionylamino]-3-(4-fluorophenyl)propionyl}-4-(1-methylcarbamoyl-2-naphthalen-2-ylethyl)piperazin-2-yl]ethyl ester, 65, (7.5 g, 10 mmol) in methanol (50 mL) is added freshly prepared NaOCH3 (0.55 g, 10.1 mmol) and the solution stirred overnight. The sol... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Aromatic alcohol | Primary alcohol.Aromatic alcohol | c1ccccc1 | c1ccccc1 | c1ccc2ccccc2c1.C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1 | HO- | CO | null | 8 | CNC(=O)C(Cc1ccc2ccccc2c1)N1CCN(C(=O)C(Cc2ccc(F)cc2)NC(=O)C(Cc2ccccc2O)NC(C)=O)C(CCOC(C)=O)C1>CO>CNC(=O)C(Cc1ccc2ccccc2c1)N1CCN(C(=O)C(Cc2ccc(F)cc2)NC(=O)C(Cc2ccc(O)cc2)NC(C)=O)C(CCO)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3bcc3ad5af944641a39f0ca173a215de | COCNC(=O)C(Cc1ccc2ccccc2c1)NC(=O)OC(C)(C)C>>CC(C)(C)OC(=O)NC(C=O)Cc1ccc2ccccc2c1 | C(C)(C)(C)OC(NC(CC1=CC2=CC=CC=C2C=C1)C(NCOC)=O)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>C(C)(C)(C)OC(NC(CC1=CC2=CC=CC=C2C=C1)C=O)=O | COCN[C:10]([CH:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:12][c:13]1[cH:14][cH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[cH:22]1)=[O:11]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH:9]([CH:10]=[O:11])[CH2:12][c:13]1[cH:14][cH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[cH:22]1 | COCNC(=O)C(Cc1ccc2ccccc2c1)NC(=O)OC(C)(C)C | CC(C)(C)OC(=O)NC(C=O)Cc1ccc2ccccc2c1 | null | null | C1CCOC1 | Reduction | OtherReaction | 62cce701cc2d159914df3ce701c0c8c5e16e6e97dcbe31a8162f4dc1f8239a90 | b1d3b3f26795b5b64058ccb00f422fad6c38ca4cb68d913673e4f6d4d45c3f9f | c1ccc2ccccc2c1 | C-O-C-N-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12]>>[C:4]-[C:3](-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[CH;D2;+0:1]=[O;D1;H0:2] | null | [] | -55 | CELSIUS | 3 | HOUR | To a solution of [1-(methoxymethylcarbamoyl)-2-naphthalen-2-ylethyl]carbamic acid tert-butyl ester, 67, (5.0 g, 13.4 mmol) in THF (40 mL) at −30° C. to −25° C. is added LAH (16.7 mL of a 1M solution in THF) over about 10 minutes and the reaction is then cooled to −55° C. and the stirring is continued for 3 hours. After... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amide | Aldehyde | null | null | c1ccc2ccccc2c1 | HO- | C1CCOC1 | -55 | 3 | COCNC(=O)C(Cc1ccc2ccccc2c1)NC(=O)OC(C)(C)C>C1CCOC1>CC(C)(C)OC(=O)NC(C=O)Cc1ccc2ccccc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c890d2c1d61a43e1a16a98e903c1d8ab | CC(=O)NC(Cc1ccc(O)cc1)C(=O)NC(Cc1ccc(F)cc1)C(=O)N1CC(Cc2ccc3ccccc3c2)NC(=O)C1Cc1cn(Cc2ccccc2)cn1>>CC(=O)NC(Cc1ccc(O)cc1)C(=O)NC(Cc1ccc(F)cc1)C(=O)N1CC(Cc2ccc3ccccc3c2)NC(=O)C1Cc1c[nH]cn1 | C(C)(=O)NC(C(=O)NC(C(=O)N1C(C(NC(C1)CC1=CC2=CC=CC=C2C=C1)=O)CC=1N=CN(C1)CC1=CC=CC=C1)CC1=CC=C(C=C1)F)CC1=CC=C(C=C1)O.C1=CCCCC1.C1=CCCCC1>>C(C)(=O)NC(C(=O)NC(C(=O)N1C(C(NC(C1)CC1=CC2=CC=CC=C2C=C1)=O)CC=1N=CNC1)CC1=CC=C(C=C1)F)CC1=CC=C(C=C1)O | c1ccc(C[n:49]2[cH:48][c:47]([CH2:46][CH:45]3[N:28]([C:26]([CH:17]([NH:16][C:14]([CH:5]([NH:4][C:2]([CH3:1])=[O:3])[CH2:6][c:7]4[cH:8][cH:9][c:10]([OH:11])[cH:12][cH:13]4)=[O:15])[CH2:18][c:19]4[cH:20][cH:21][c:22]([F:23])[cH:24][cH:25]4)=[O:27])[CH2:29][CH:30]([CH2:31][c:32]4[cH:33][cH:34][c:35]5[cH:36][cH:37][cH:38][c... | CC(=O)NC(Cc1ccc(O)cc1)C(=O)NC(Cc1ccc(F)cc1)C(=O)N1CC(Cc2ccc3ccccc3c2)NC(=O)C1Cc1cn(Cc2ccccc2)cn1 | CC(=O)NC(Cc1ccc(O)cc1)C(=O)NC(Cc1ccc(F)cc1)C(=O)N1CC(Cc2ccc3ccccc3c2)NC(=O)C1Cc1c[nH]cn1 | null | [Pd] | C(C)O.C(C)(=O)O | Deprotection | OtherReaction | 8ddafbb6c156b494ff4d975fdba1c331bfcc9cd01ad96ea8735cc0e1a145e661 | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | O=C(CCc1ccccc1)NC(Cc1ccccc1)C(=O)N1CC(Cc2ccc3ccccc3c2)NC(=O)C1Cc1c[nH]cn1 | [C:1]-[c:2]1:[#7;a:3]:[c:4]:[n;H0;D3;+0:5](-C-c2:c:c:c:c:c:2):[c:6]:1>>[C:1]-[c:2]1:[#7;a:3]:[c:4]:[nH;D2;+0:5]:[c:6]:1 | null | [] | null | null | 2 | DAY | 2-acetylamino-N-[2-[2-(1-benzyl-1H-imidazol-4-ylmethyl)-5-naphthalen-2-ylmethyl-3-oxo-piperazin-1-yl]-1-(4-fluorobenzyl)-2-oxo-ethyl]-3-(4-hydroxyphenyl)propionamide, 73, (0.22 g, 0.28 mmol) is dissolved in ethanol/acetic acid (4:1) (3 mL). Cyclohexene (3 mL) and Pd-black are added and the solution is refluxed with per... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1c[nH]cn1 | c1c[nH]cn1 | c1ccccc1.c1ccccc1.C1C[NH]CCN1.c1ccc2ccccc2c1.c1c[nH]cn1 | Other | [Pd].C(C)O.C(C)(=O)O | null | 48 | CC(=O)NC(Cc1ccc(O)cc1)C(=O)NC(Cc1ccc(F)cc1)C(=O)N1CC(Cc2ccc3ccccc3c2)NC(=O)C1Cc1cn(Cc2ccccc2)cn1>[Pd].C(C)O.C(C)(=O)O>CC(=O)NC(Cc1ccc(O)cc1)C(=O)NC(Cc1ccc(F)cc1)C(=O)N1CC(Cc2ccc3ccccc3c2)NC(=O)C1Cc1c[nH]cn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3fc3acc4d41f4e47bb631040264c388f | C=CCCBr.F[Si](F)(c1ccccc1)c1ccccc1>>C=CCC[Si](F)(c1ccccc1)c1ccccc1 | [Mg].II.BrCCC=C.F[Si](C1=CC=CC=C1)(C1=CC=CC=C1)F.II>>C(CC=C)[Si](F)(C1=CC=CC=C1)C1=CC=CC=C1 | Br[CH2:4][CH2:3][CH:2]=[CH2:1].F[Si:5]([F:6])([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH2:1]=[CH:2][CH2:3][CH2:4][Si:5]([F:6])([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | C=CCCBr.F[Si](F)(c1ccccc1)c1ccccc1 | C=CCC[Si](F)(c1ccccc1)c1ccccc1 | null | null | CCOCC | Functional Group Interconversion | OtherReaction | 0a81b1d1e97e0c2f2ba0f6ef40833060c1f298d86e4217deb69d2e2d41e13391 | e3d8d9257aaec065420cabb8aef7586bf6f63d364d4996e5d8ee45b5f92d1640 | c1ccc([SiH2]c2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]=[C;D1;H2:4].F-[Si;H0;D4;+0:5](-[F;D1;H0:6])(-[c:7](:[c:8]):[c:9])-[c:10](:[c:11]):[c:12]>>[C;D1;H2:4]=[C:3]-[C:2]-[CH2;D2;+0:1]-[Si;H0;D4;+0:5](-[F;D1;H0:6])(-[c:7](:[c:8]):[c:9])-[c:10](:[c:11]):[c:12] | 83.1 | [{"value": 83.0, "product": "C(CC=C)[Si](F)(C1=CC=CC=C1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.1, "product": "C(CC=C)[Si](F)(C1=CC=CC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | In a two-neck flask equipped with a condenser was placed magnesium (3.46 g, 142 mmol) and a crystal of iodine. The flask was warmed with heat gun until iodine had sublimed. A solution of 4-bromo-1-butene (9.62 g, 71.3 mmol) in ether (100 mL) was added dropwise in 30 min and the resulting mixture refluxed for 2 h. This ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Silyl protective group | Silyl protective group | null | null | c1ccccc1.c1ccccc1 | Br- | CCOCC | null | 8 | C=CCCBr.F[Si](F)(c1ccccc1)c1ccccc1>CCOCC>C=CCC[Si](F)(c1ccccc1)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4da5c44b296f486dad78480c8775c10a | C1CSCSC1.C=CCC[Si](F)(c1ccccc1)c1ccccc1>>C=CCC[Si](c1ccccc1)(c1ccccc1)C1SCCCS1 | C(CC=C)[Si](F)(C1=CC=CC=C1)C1=CC=CC=C1.S1CSCCC1.C(CCC)[Li]>>C(CC=C)[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C1SCCCS1 | [CH2:18]1[S:19][CH2:20][CH2:21][CH2:22][S:23]1.F[Si:5]([CH2:4][CH2:3][CH:2]=[CH2:1])([c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[CH2:1]=[CH:2][CH2:3][CH2:4][Si:5]([c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)([c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[CH:18]1[S:19][CH2:20][CH2:21]... | C1CSCSC1.C=CCC[Si](F)(c1ccccc1)c1ccccc1 | C=CCC[Si](c1ccccc1)(c1ccccc1)C1SCCCS1 | null | null | C1CCOC1 | Functional Group Interconversion | OtherReaction | a43023f814b7838c122734a40618912b08e77e44e2041425112484de478e7a16 | c38b0d7d6ef7d2a586905c52a4372204657af855a0430d8b36e4b5bbdcab3867 | c1ccc([SiH](c2ccccc2)C2SCCCS2)cc1 | F-[Si;H0;D4;+0:1](-[C:2]-[C:3]-[C:4]=[C;D1;H2:5])(-[c:6](:[c:7]):[c:8])-[c:9](:[c:10]):[c:11].[C:12]-[#16:13]-[CH2;D2;+0:14]-[#16:15]-[C:16]>>[C:12]-[#16:13]-[CH;D3;+0:14](-[Si;H0;D4;+0:1](-[C:2]-[C:3]-[C:4]=[C;D1;H2:5])(-[c:6](:[c:7]):[c:8])-[c:9](:[c:10]):[c:11])-[#16:15]-[C:16] | null | [] | null | null | 2 | HOUR | To a solution of 1,3-dithiane (6.77 g, 56.3 mmol) in THF (120 mL) at −78° C. was added dropwise over 10 min n-butyllithium (1.6 M in hexane, 50 mmol), and the solution was stirred for 2 h under argon. A solution of 31 (11.1 g, 43.3 mmol) in THF (100 mL) was added, the mixture was stirred for 3 h at −78° C., and overnig... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide.Monosulfide.Silyl protective group | Monosulfide.Monosulfide.Silyl protective group | C1CSCSC1 | C1CSCSC1 | c1ccccc1.c1ccccc1.C1CSCSC1 | HF | C1CCOC1 | null | 2 | C1CSCSC1.C=CCC[Si](F)(c1ccccc1)c1ccccc1>C1CCOC1>C=CCC[Si](c1ccccc1)(c1ccccc1)C1SCCCS1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3fe8d034ca14456e97abe8dd4b1276d2 | C=CCC[Si](c1ccccc1)(c1ccccc1)C1SCCCS1.CC(C)CBr>>C=CCC[Si](c1ccccc1)(c1ccccc1)C1(CC(C)C)SCCCS1 | BrCC(C)C.C(CC=C)[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C1SCCCS1.C(CCC)[Li]>>C(CC=C)[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C1(SCCCS1)CC(C)C | [CH2:1]=[CH:2][CH2:3][CH2:4][Si:5]([c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)([c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[CH:18]1[S:23][CH2:24][CH2:25][CH2:26][S:27]1.Br[CH2:19][CH:20]([CH3:21])[CH3:22]>>[CH2:1]=[CH:2][CH2:3][CH2:4][Si:5]([c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)([c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17... | C=CCC[Si](c1ccccc1)(c1ccccc1)C1SCCCS1.CC(C)CBr | C=CCC[Si](c1ccccc1)(c1ccccc1)C1(CC(C)C)SCCCS1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | ab0114b4a4cb6005c4898e16d6c0a2b288ca25c97a67a873f171ed1d3be6a47c | 4efa513f567c8dda6a947e269b70f7a500c3fa9b005a8552cb1e41aa23aad50b | c1ccc([SiH](c2ccccc2)C2SCCCS2)cc1 | Br-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])-[C;D1;H3:4].[C:5]-[#16:6]-[CH;D3;+0:7](-[#14:8](-[C:9])(-[c:10])-[c:11])-[#16:12]-[C:13]>>[C:5]-[#16:6]-[C;H0;D4;+0:7](-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])-[C;D1;H3:4])(-[#14:8](-[C:9])(-[c:10])-[c:11])-[#16:12]-[C:13] | 92.5 | [{"value": 92.0, "product": "C(CC=C)[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C1(SCCCS1)CC(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.5, "product": "C(CC=C)[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C1(SCCCS1)CC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of 32 (4.68 g, 13.1 mmol) in THF (100 mL) at −78° C. was added dropwise over 10 min n-butyllithium (1.6 M in hexanes, 18.4 mmol). After 3 h of stirring under argon, 1-bromo-2-methylpropane (2.14 mL, 19.7 mmol) was added dropwise over 5 min, and the mixture was stirred for 2 h at −78° C. and overnight at r... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Monosulfide.Monosulfide | Monosulfide.Monosulfide | C1CSCSC1 | C1CSCSC1 | c1ccccc1.c1ccccc1.C1CSCSC1 | HBr | C1CCOC1 | null | 3 | C=CCC[Si](c1ccccc1)(c1ccccc1)C1SCCCS1.CC(C)CBr>C1CCOC1>C=CCC[Si](c1ccccc1)(c1ccccc1)C1(CC(C)C)SCCCS1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d41ccf720ab94cdf82e21c85e2c9b1d6 | C=CCC[Si](c1ccccc1)(c1ccccc1)C1(CC(C)C)SCCCS1.O>>C=CCC[Si](C(=O)CC(C)C)(c1ccccc1)c1ccccc1 | C(CC=C)[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C1(SCCCS1)CC(C)C.O>>C(CC=C)[Si](C(CC(C)C)=O)(C1=CC=CC=C1)C1=CC=CC=C1 | C1CS[C:6]([Si:5]([CH2:4][CH2:3][CH:2]=[CH2:1])([c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)([CH2:8][CH:9]([CH3:10])[CH3:11])SC1.[OH2:7]>>[CH2:1]=[CH:2][CH2:3][CH2:4][Si:5]([C:6](=[O:7])[CH2:8][CH:9]([CH3:10])[CH3:11])([c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[c:18]1[cH:19]... | C=CCC[Si](c1ccccc1)(c1ccccc1)C1(CC(C)C)SCCCS1.O | C=CCC[Si](C(=O)CC(C)C)(c1ccccc1)c1ccccc1 | null | Cl[Hg]Cl | CC#N | Heteroatom Alkylation and Arylation | OtherReaction | 20a35e959b383d160a4af6c0c4ada6cab26a4e16b8d461bbc0b67eec8a690064 | 29a69844964b167d29a273bc4229acfa423d2f907fcdc561fd455432cc95c1ad | c1ccc([SiH2]c2ccccc2)cc1 | [C:1]-[#14:2](-[c:3])(-[c:4])-[C;H0;D4;+0:5]1(-[C:6]-[C:7])-S-C-C-C-S-1.[OH2;D0;+0:8]>>[C:1]-[#14:2](-[c:3])(-[c:4])-[C;H0;D3;+0:5](=[O;H0;D1;+0:8])-[C:6]-[C:7] | 88 | [{"value": 88.0, "product": "C(CC=C)[Si](C(CC(C)C)=O)(C1=CC=CC=C1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 26 (4.64 g 11.2 mmol) in CH3CN (300 mL) was added water (10 mL) and HgCl2 (15.26 g, 56.21 mmol). After stirring overnight at rt, the mixture was concentrated and partitioned between water (100 mL) and hexane (200 mL). The organic layer was isolated and the aqueous layer extracted with hexane (50 mL). T... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide.Monosulfide | null | C1CSCSC1 | null | c1ccccc1.c1ccccc1 | Other | Cl[Hg]Cl.CC#N | null | 8 | C=CCC[Si](c1ccccc1)(c1ccccc1)C1(CC(C)C)SCCCS1.O>Cl[Hg]Cl.CC#N>C=CCC[Si](C(=O)CC(C)C)(c1ccccc1)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dc0c6a839ea34b48b84ba6911f804829 | C=CCC[Si](C(=O)CC(C)C)(c1ccccc1)c1ccccc1>>C=CCC[Si](c1ccccc1)(c1ccccc1)C(O)CC(C)C | C(CC=C)[Si](C(CC(C)C)=O)(C1=CC=CC=C1)C1=CC=CC=C1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>C(CC=C)[Si](C(CC(C)C)O)(C1=CC=CC=C1)C1=CC=CC=C1 | [CH2:1]=[CH:2][CH2:3][CH2:4][Si:5]([c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)([c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[C:18](=[O:19])[CH2:20][CH:21]([CH3:22])[CH3:23]>>[CH2:1]=[CH:2][CH2:3][CH2:4][Si:5]([c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)([c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[CH:18]([OH:19])[CH2:20][CH:21... | C=CCC[Si](C(=O)CC(C)C)(c1ccccc1)c1ccccc1 | C=CCC[Si](c1ccccc1)(c1ccccc1)C(O)CC(C)C | null | null | C(C)OCC | Reduction | OtherReaction | 847c2b856eb50628f99a97f168b14104abfe375240a6ba06390d579176264c12 | 9cd2da225b0dfd2300e1eef770885fa01efe371d4cca020a5e4a899922e10ff9 | c1ccc([SiH2]c2ccccc2)cc1 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[#14:5](-[C:6])(-[c:7])-[c:8]>>[C:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[#14:5](-[C:6])(-[c:7])-[c:8] | 69.6 | [{"value": 69.0, "product": "C(CC=C)[Si](C(CC(C)C)O)(C1=CC=CC=C1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.6, "product": "C(CC=C)[Si](C(CC(C)C)O)(C1=CC=CC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 15 | MINUTE | To a solution of 33 (3.0 g, 9.3 mmol) in ethyl ether (100 mL) at 0° C. was added lithium aluminum hydride (1.0 M in ethyl ether, 47 mmol). After stirring for 15 min at 0° C. under argon, the reaction mixture was diluted with ethyl ether (300 mL) and quenched with saturated aqueous Na2SO4 until evolution of hydrogen had... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary alcohol | null | null | c1ccccc1.c1ccccc1 | null | C(C)OCC | 0 | 0.25 | C=CCC[Si](C(=O)CC(C)C)(c1ccccc1)c1ccccc1>C(C)OCC>C=CCC[Si](c1ccccc1)(c1ccccc1)C(O)CC(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0c1116db73674a7c866544136f11b01a | C=CCC[Si](c1ccccc1)(c1ccccc1)C(O)CC(C)C.[N-]=[N+]=[N-]>>C=CCC[Si](c1ccccc1)(c1ccccc1)C(CC(C)C)N=[N+]=[N-] | C(CC=C)[Si](C(CC(C)C)O)(C1=CC=CC=C1)C1=CC=CC=C1.CS(=O)(=O)Cl.[N-]=[N+]=[N-].[Na+]>>N(=[N+]=[N-])C(CC(C)C)[Si](C1=CC=CC=C1)(C1=CC=CC=C1)CCC=C | O[CH:18]([Si:5]([CH2:4][CH2:3][CH:2]=[CH2:1])([c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[CH2:19][CH:20]([CH3:21])[CH3:22].[N-:23]=[N+:24]=[N-:25]>>[CH2:1]=[CH:2][CH2:3][CH2:4][Si:5]([c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)([c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[CH:18]([CH... | C=CCC[Si](c1ccccc1)(c1ccccc1)C(O)CC(C)C.[N-]=[N+]=[N-] | C=CCC[Si](c1ccccc1)(c1ccccc1)C(CC(C)C)N=[N+]=[N-] | null | null | CCN(CC)CC.C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 985bfd7f1f6b08dfb69ac397b6f5dc212a21c6fab55bf5a78aa078e16aad2620 | a84ee1c3dd499ad7fd8df50465bd467b5c7a479fe957929d840e01571a4bc197 | c1ccc([SiH2]c2ccccc2)cc1 | O-[CH;D3;+0:1](-[C:2]-[C:3])-[#14:4](-[C:5])(-[c:6])-[c:7].[N-;H0;D1:8]=[#7;+:9]=[N;-;D1;H0:10]>>[C:3]-[C:2]-[CH;D3;+0:1](-[N;H0;D2;+0:8]=[#7;+:9]=[N;-;D1;H0:10])-[#14:4](-[C:5])(-[c:6])-[c:7] | 87 | [{"value": 87.0, "product": "N(=[N+]=[N-])C(CC(C)C)[Si](C1=CC=CC=C1)(C1=CC=CC=C1)CCC=C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.0, "product": "N(=[N+]=[N-])C(CC(C)C)[Si](C1=CC=CC=C1)(C1=CC=CC=C1)CCC=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 34 (1.68 g, 5.16 mmol) in CH2Cl2 (100 mL) and Et3N (3.6 mL) at 0° C. was added dropwise over 5 min methanesulfonyl chloride (2.96 g, 25.8 mmol), and the solution was allowed to warm to rt over 1 h. After stirring overnight under argon, the mixture was cooled to 0° C. and quenched with water (50 mL). Th... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Azide | null | null | c1ccccc1.c1ccccc1 | HO- | CCN(CC)CC.C(Cl)Cl | null | 8 | C=CCC[Si](c1ccccc1)(c1ccccc1)C(O)CC(C)C.[N-]=[N+]=[N-]>CCN(CC)CC.C(Cl)Cl>C=CCC[Si](c1ccccc1)(c1ccccc1)C(CC(C)C)N=[N+]=[N-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b5625cc19dec432d8b2f7d4b95507c0b | C1CSCSC1.C=CCC[SiH](CF)c1ccccc1>>C=CCC[SiH](CC1SCCCS1)c1ccccc1 | C(CC=C)[SiH](C1=CC=CC=C1)CF.S1CSCCC1.C(CCC)[Li]>>C(CC=C)[SiH](C1=CC=CC=C1)CC1SCCCS1 | [CH2:7]1[S:8][CH2:9][CH2:10][CH2:11][S:12]1.F[CH2:6][SiH:5]([CH2:4][CH2:3][CH:2]=[CH2:1])[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH2:1]=[CH:2][CH2:3][CH2:4][SiH:5]([CH2:6][CH:7]1[S:8][CH2:9][CH2:10][CH2:11][S:12]1)[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | C1CSCSC1.C=CCC[SiH](CF)c1ccccc1 | C=CCC[SiH](CC1SCCCS1)c1ccccc1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | ab0114b4a4cb6005c4898e16d6c0a2b288ca25c97a67a873f171ed1d3be6a47c | 4efa513f567c8dda6a947e269b70f7a500c3fa9b005a8552cb1e41aa23aad50b | c1ccc([SiH2]CC2SCCCS2)cc1 | F-[CH2;D2;+0:1]-[#14:2](-[C:3])-[c:4].[C:5]-[#16:6]-[CH2;D2;+0:7]-[#16:8]-[C:9]>>[C:5]-[#16:6]-[CH;D3;+0:7](-[CH2;D2;+0:1]-[#14:2](-[C:3])-[c:4])-[#16:8]-[C:9] | null | [] | null | null | 2 | HOUR | To a solution of 1,3-dithiane (11.1 g, 91.9 mmol) in THF (150 mL) at −78° C. was added dropwise over 10 min n-butyllithium (1.6 M in hexane, 76.6 mmol), and the solution was stirred for 2 h under argon. A solution of 42 (11.9 g, 61.3 mmol) in THF (120 mL) was added dropwise over 30 min, and the mixture was stirred for ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Monosulfide.Monosulfide | Monosulfide.Monosulfide | C1CSCSC1 | C1CSCSC1 | C1CSCSC1.c1ccccc1 | HF | C1CCOC1 | null | 2 | C1CSCSC1.C=CCC[SiH](CF)c1ccccc1>C1CCOC1>C=CCC[SiH](CC1SCCCS1)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-944f1193a82d4416b583f12b44d9cb7f | C=CCC[Si](C)(c1ccccc1)C1(CC(C)C)SCCCS1.O>>C=CCC[Si](C)(C(=O)CC(C)C)c1ccccc1 | C(CC=C)[Si](C1=CC=CC=C1)(C1(SCCCS1)CC(C)C)C.O>>C(CC=C)[Si](C(CC(C)C)=O)(C1=CC=CC=C1)C | C1CS[C:7]([Si:5]([CH2:4][CH2:3][CH:2]=[CH2:1])([CH3:6])[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)([CH2:9][CH:10]([CH3:11])[CH3:12])SC1.[OH2:8]>>[CH2:1]=[CH:2][CH2:3][CH2:4][Si:5]([CH3:6])([C:7](=[O:8])[CH2:9][CH:10]([CH3:11])[CH3:12])[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | C=CCC[Si](C)(c1ccccc1)C1(CC(C)C)SCCCS1.O | C=CCC[Si](C)(C(=O)CC(C)C)c1ccccc1 | null | Cl[Hg]Cl | CC#N | Heteroatom Alkylation and Arylation | OtherReaction | 20a35e959b383d160a4af6c0c4ada6cab26a4e16b8d461bbc0b67eec8a690064 | 29a69844964b167d29a273bc4229acfa423d2f907fcdc561fd455432cc95c1ad | c1ccccc1 | [C:1]-[C:2]-[C;H0;D4;+0:3]1(-[#14:4](-[C;D1;H3:5])(-[c:6])-[C:7]-[C:8]-[C:9]=[C;D1;H2:10])-S-C-C-C-S-1.[OH2;D0;+0:11]>>[C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:11])-[#14:4](-[C;D1;H3:5])(-[c:6])-[C:7]-[C:8]-[C:9]=[C;D1;H2:10] | null | [] | null | null | 8 | HOUR | To a solution of 44 (6.19 g, 177 mmol) in CH3CN (200 mL) was added water (10 mL) and HgCl2 (24 g, 88 mmol). After stirring overnight at rt, the mixture was concentrated and partitioned between water (100 mL) and hexane (200 mL). The organic layer was isolated and the aqueous layer extracted twice with 50-mL portions of... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide.Monosulfide | null | C1CSCSC1 | null | c1ccccc1 | Other | Cl[Hg]Cl.CC#N | null | 8 | C=CCC[Si](C)(c1ccccc1)C1(CC(C)C)SCCCS1.O>Cl[Hg]Cl.CC#N>C=CCC[Si](C)(C(=O)CC(C)C)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-79ef2b2e24c44cd2b690c3a31b465eff | C=CCC[Si](c1ccccc1)(c1ccccc1)C1SCCCS1.CC(C)CC(NC(=O)c1ccccc1)[Si](CCC(=O)NCc1ccccc1)(c1ccccc1)c1ccccc1>>C=CCC[Si](C)(c1ccccc1)C(CC(C)C)N=[N+]=[N-] | C1(=CC=CC=C1)[Si](C(CC(C)C)NC(C1=CC=CC=C1)=O)(CCC(NCC1=CC=CC=C1)=O)C1=CC=CC=C1.[N-]=[N+]=[N-].[Na+].Cl[SiH2]Cl.[SiH3]O[SiH2]O[SiH3].CCN(CC)CC.CS(=O)(=O)Cl.C(CC=C)[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C1SCCCS1>>N(=[N+]=[N-])C(CC(C)C)[Si](C1=CC=CC=C1)(C)CCC=C | c1ccc([Si](c2ccccc2)(C2SCCCS2)[CH2:4][CH2:3][CH:2]=[CH2:1])cc1.O=C(C[CH2:6][Si:5](c1ccccc1)([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[CH:13]([CH2:14][CH:15]([CH3:16])[CH3:17])[NH:18]C(=O)c1ccccc1)NCc1ccccc1>>[CH2:1]=[CH:2][CH2:3][CH2:4][Si:5]([CH3:6])([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[CH:13]([CH2:14][CH:15]([CH... | C=CCC[Si](c1ccccc1)(c1ccccc1)C1SCCCS1.CC(C)CC(NC(=O)c1ccccc1)[Si](CCC(=O)NCc1ccccc1)(c1ccccc1)c1ccccc1 | C=CCC[Si](C)(c1ccccc1)C(CC(C)C)N=[N+]=[N-] | null | null | CCOC(=O)C.C(Cl)Cl.CCCCCC | Miscellaneous | OtherReaction | 01287dbbe51ee4ed02bf9bbeb9bd7d1400bbcdb19baf1ee1beca09219b643349 | 7966538f2596cfbb0a11cf3989b6dcf4ab5182fde96a57ef1458d7c3d4534f01 | c1ccccc1 | O=C(-C-[CH2;D2;+0:1]-[Si;H0;D4;+0:2](-[C:3](-[C:4])-[NH;D2;+0:5]-C(=O)-c1:c:c:c:c:c:1)(-[c:6](:[c:7]):[c:8])-c1:c:c:c:c:c:1)-N-C-c1:c:c:c:c:c:1.[C;D1;H2:9]=[C:10]-[C:11]-[CH2;D2;+0:12]-[Si](-C1-S-C-C-C-S-1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:4]-[C:3](-[N;H0;D2;+0:5]=[#7;+:13]=[N;-;D1;H0:14])-[Si;H0;D4;+0:2](-[CH3;D1;+... | null | [] | null | null | 8 | HOUR | To a solution of 46 (3.4 g, 13 mmol) in CH2Cl2 (150 mL) and Et3N (9 mL, 65 mmol) at 0° C. was added dropwise over 5 min methanesulfonyl chloride (7.4 g, 65 mmol), and the mixture was allowed to warm to rt over 1 h. After stirring overnight under argon, the mixture was cooled to 0° C. and quenched with water (50 mL). Th... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Secondary amide.Monosulfide.Monosulfide.Silyl protective group.Silyl protective group | Azide.Silyl protective group | c1ccccc1.c1ccccc1.C1CSCSC1.c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccccc1 | Other | CCOC(=O)C.C(Cl)Cl.CCCCCC | null | 8 | C=CCC[Si](c1ccccc1)(c1ccccc1)C1SCCCS1.CC(C)CC(NC(=O)c1ccccc1)[Si](CCC(=O)NCc1ccccc1)(c1ccccc1)c1ccccc1>CCOC(=O)C.C(Cl)Cl.CCCCCC>C=CCC[Si](C)(c1ccccc1)C(CC(C)C)N=[N+]=[N-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-229707299eef4e57a0a41526fb522404 | C=CCC[Si](C)(c1ccccc1)C(CC(C)C)N=[N+]=[N-].O=C(Cl)c1ccccc1>>C=CCC[Si](C)(c1ccccc1)C(CC(C)C)NC(=O)c1ccccc1 | C(C1=CC=CC=C1)(=O)Cl.N(=[N+]=[N-])C(CC(C)C)[Si](C1=CC=CC=C1)(C)CCC=C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>C(CC=C)[Si](C(CC(C)C)NC(C1=CC=CC=C1)=O)(C1=CC=CC=C1)C | [N-]=[N+]=[N:18][CH:13]([Si:5]([CH2:4][CH2:3][CH:2]=[CH2:1])([CH3:6])[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[CH2:14][CH:15]([CH3:16])[CH3:17].Cl[C:19](=[O:20])[c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1>>[CH2:1]=[CH:2][CH2:3][CH2:4][Si:5]([CH3:6])([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[CH:13]([CH2:14][CH:15]([CH3:... | C=CCC[Si](C)(c1ccccc1)C(CC(C)C)N=[N+]=[N-].O=C(Cl)c1ccccc1 | C=CCC[Si](C)(c1ccccc1)C(CC(C)C)NC(=O)c1ccccc1 | null | null | C(Cl)Cl.CCN(CC)CC.C(C)OCC.CCOCC | Acylation | OtherReaction | 735710316d7e87ac9338215a20e720bc8719191bd48a2d3acb28faa5bbaf1fbe | ceca836652f7b17d768b7cd86d674082404222b15fc392aa02ee722a632b2cc0 | O=C(NC[SiH2]c1ccccc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7](-[N;H0;D2;+0:8]=[N+]=[N-])-[#14:9](-[C:10])-[C;D1;H3:11]>>[C:6]-[C:7](-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[#14:9](-[C:10])-[C;D1;H3:11] | null | [] | null | null | 30 | MINUTE | To a solution of azide 47 (2.75 g, 9.57 mmol) in ethyl ether (100 mL) at 0° C. was added dropwise over 5 min lithium aluminum hydride (1 M in ether, 47.8 mmol), and the mixture was allowed to warm to rt over 10 min. After stirring for 30 min under argon the mixture was cooled to 0° C. and diluted with ether (100 mL). T... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Azide | Secondary amide | null | null | c1ccccc1.c1ccccc1 | Other | C(Cl)Cl.CCN(CC)CC.C(C)OCC.CCOCC | null | 0.5 | C=CCC[Si](C)(c1ccccc1)C(CC(C)C)N=[N+]=[N-].O=C(Cl)c1ccccc1>C(Cl)Cl.CCN(CC)CC.C(C)OCC.CCOCC>C=CCC[Si](C)(c1ccccc1)C(CC(C)C)NC(=O)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e850a39a765f4f10ab362963cd7f5340 | C=CCC[Si](C)(c1ccccc1)C(CC(C)C)NC(=O)c1ccccc1>>CC(C)CC(NC(=O)c1ccccc1)[Si](C)(CCC(=O)O)c1ccccc1 | OS(=O)[O-].[Na+].CS(=O)(=O)[O-].C(CC=C)[Si](C(CC(C)C)NC(C1=CC=CC=C1)=O)(C1=CC=CC=C1)C.CC(=O)C.OS(=O)(=O)O.O=[Cr](=O)=O>>C(C1=CC=CC=C1)(=O)NC(CC(C)C)[Si](CCC(=O)O)(C1=CC=CC=C1)C | C=[CH:19][CH2:18][CH2:17][Si:15]([CH:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[NH:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)([CH3:16])[c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH:5]([NH:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[Si:15]([CH3:16])([CH2:17][CH2:18][... | C=CCC[Si](C)(c1ccccc1)C(CC(C)C)NC(=O)c1ccccc1 | CC(C)CC(NC(=O)c1ccccc1)[Si](C)(CCC(=O)O)c1ccccc1 | null | O=[Os](=O)(=O)=O | CCOC(=O)C.CC(=O)C.CC(C)O.CCCCCC.O | Oxidation | Oxidation of alkene to carboxylic acid | c76877f5d07b25cd67feb173601dfc186356d7e749409ee335024ab312450c19 | da4c067d565d145c0fc2615716920058c67cc7ef63536355825168eb0bdc4c16 | O=C(NC[SiH2]c1ccccc1)c1ccccc1 | C=[CH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[C;H0;D3;+0:1](=[O;D1;H0:4])-[O;D1;H1:5] | null | [] | null | null | 24 | HOUR | To a solution of 49 (0.7 g, 1.91 mmol) in acetone (22 mL) was added 0.23 mL (2 mol %) of a 4 wt % solution of OsO4 in water and Jones reagent (2.43 mL, 6.49 mmol). After stirring the mixture for 24 h at rt, 2-propanol (0.5 mL) was added followed by NaHSO3 (0.2 g). The mixture was diluted with water (50 mL) and stirred ... | 10.6084/m9.figshare.5104873.v1 | null | Allyl | Carboxylic acid | null | null | c1ccccc1.c1ccccc1 | Other | O=[Os](=O)(=O)=O.CCOC(=O)C.CC(=O)C.CC(C)O.CCCCCC.O | null | 24 | C=CCC[Si](C)(c1ccccc1)C(CC(C)C)NC(=O)c1ccccc1>O=[Os](=O)(=O)=O.CCOC(=O)C.CC(=O)C.CC(C)O.CCCCCC.O>CC(C)CC(NC(=O)c1ccccc1)[Si](C)(CCC(=O)O)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e9b74b1543024f7095957018614387c0 | BrC1=C2C(=Cc3cc(Br)c(Br)c(Br)c32)C2(C=CC=C3C2=Cc2ccccc23)C(Br)=C1Br.OB(O)c1ccc(-c2ccccc2)cc1>>c1ccc(-c2ccccc2-c2ccc3c(c2)C2(c4cc(-c5ccccc5-c5ccccc5)ccc4-c4c(-c5ccccc5-c5ccccc5)cc(-c5ccccc5-c5ccccc5)cc42)c2cc(-c4ccccc4-c4ccccc4)cc(-c4ccccc4-c4ccccc4)c2-3)cc1 | BrC1=C(C(=C2C3=C(C(=C(C4(C3=CC2=C1)C=CC=C1C2=CC=CC=C2C=C14)Br)Br)Br)Br)Br.B(C=1C=CC(=CC1)C=2C=CC=CC2)(O)O>>C1(=C(C=CC=C1)C1=CC=2C3(C4=CC(=CC=C4C2C(=C1)C1=C(C=CC=C1)C1=CC=CC=C1)C1=C(C=CC=C1)C1=CC=CC=C1)C1=CC(=CC=C1C=1C(=CC(=CC13)C1=C(C=CC=C1)C1=CC=CC=C1)C1=C(C=CC=C1)C1=CC=CC=C1)C1=C(C=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 | Br[C:5]1=[C:50](Br)[C:37]2([C:10]3=[CH:9][c:89]4[c:88]([cH:93][cH:92][cH:91][cH:90]4)[C:83]3=[CH:84][CH:85]=[CH:86]2)[C:36]2=[CH:35][c:18]3[c:13]([c:12](Br)[c:21](Br)[c:20](Br)[cH:19]3)[C:65]2=[C:17]1Br.OB(O)[c:1]1[cH:2][cH:3][c:4](-[c:27]2[cH:28][cH:29][cH:30][cH:31][cH:32]2)[cH:96][cH:97]1>>[cH:1]1[cH:2][cH:3][c:4](-... | BrC1=C2C(=Cc3cc(Br)c(Br)c(Br)c32)C2(C=CC=C3C2=Cc2ccccc23)C(Br)=C1Br.OB(O)c1ccc(-c2ccccc2)cc1 | c1ccc(-c2ccccc2-c2ccc3c(c2)C2(c4cc(-c5ccccc5-c5ccccc5)ccc4-c4c(-c5ccccc5-c5ccccc5)cc(-c5ccccc5-c5ccccc5)cc42)c2cc(-c4ccccc4-c4ccccc4)cc(-c4ccccc4-c4ccccc4)c2-3)cc1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C([O-])([O-])=O.[K+].[K+].C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | cc2a26d7cb6025ea6b726939540aac6aa87fbb986faca0ea08da4f276c60666a | 8763ba013fd3670a1b05a569c466da22e86c46f2ba0e786e0c871a13a03be492 | c1ccc(-c2ccccc2-c2ccc3c(c2)C2(c4cc(-c5ccccc5-c5ccccc5)ccc4-c4c(-c5ccccc5-c5ccccc5)cc(-c5ccccc5-c5ccccc5)cc42)c2cc(-c4ccccc4-c4ccccc4)cc(-c4ccccc4-c4ccccc4)c2-3)cc1 | Br-[C;H0;D3;+0:1]1=[C;H0;D3;+0:2]2-[C;H0;D3;+0:3](=[CH;D2;+0:4]-[c;H0;D3;+0:5]3:[c:6]:[c;H0;D3;+0:7](-Br):[c;H0;D3;+0:8](-Br):[c;H0;D3;+0:9](-Br):[c;H0;D3;+0:10]:3-2)-[C;H0;D4;+0:11]2(-[CH;D2;+0:12]=[CH;D2;+0:13]-[CH;D2;+0:14]=[C;H0;D3;+0:15]3-[C;H0;D3;+0:16]-2=[CH;D2;+0:17]-[c;H0;D3;+0:18]2:[c:19]:[c:20]:[c:21]:[cH;D2... | null | [] | null | null | null | null | In a 250 ml two-necked flask fitted with reflux condenser and precision glass stirrer, 1.6 g of hexabromospirobifluorene and 3 g of biphenylboronic acid are slurried in a mixture of 50 ml of toluene and 50 ml of 1 M potassium carbonate solution. The mixture is refluxed under nitrogen and 115 mg of tetrakis(triphenylpho... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Alkenyl halide.Alkenyl halide.Alkenyl halide.Boronic acid.Conjugated diene | null | C1=CC2(C=CC=C3C2=Cc2ccccc23)C2=Cc3ccccc3C2=C1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2c(c1)C1(c3ccccc32)c2ccccc2c2ccccc21 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2c(c1)C1(c3ccccc32)c2ccccc2c2ccccc21 | Br-.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C([O-])([O-])=O.[K+].[K+].C1(=CC=CC=C1)C | null | null | BrC1=C2C(=Cc3cc(Br)c(Br)c(Br)c32)C2(C=CC=C3C2=Cc2ccccc23)C(Br)=C1Br.OB(O)c1ccc(-c2ccccc2)cc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C([O-])([O-])=O.[K+].[K+].C1(=CC=CC=C1)C>c1ccc(-c2ccccc2... |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-54b352adf61040b1b1cb278b819ac59a | CC(C)(C)c1ccc(C#N)cc1.[N-]=[N+]=[N-]>>CC(C)(C)c1ccc(-c2nnn[nH]2)cc1 | C(C)(C)(C)C1=CC=C(C#N)C=C1.[Cl-].[Li+].[N-]=[N+]=[N-].[Na+].[Br-].C(C)[NH+](CC)CC.Cl>>C(C)(C)(C)C1=CC=C(C=C1)C1=NN=NN1 | [CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([C:9]#[N:10])[cH:14][cH:15]1.[N+:11](=[N-:12])=[N-:13]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[n:10][n:11][n:12][nH:13]2)[cH:14][cH:15]1 | CC(C)(C)c1ccc(C#N)cc1.[N-]=[N+]=[N-] | CC(C)(C)c1ccc(-c2nnn[nH]2)cc1 | null | null | O.CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 237b84aaa459abf427f233dc6a07a1d9de824f980714e458423189bb68f60f12 | d8c808528b7ee68720aaeebd35cb6a2a30e344748d0066102cdae99843b93cf0 | c1ccc(-c2nnn[nH]2)cc1 | [N-;H0;D1:1]=[N+;H0;D2:2]=[N-;H0;D1:3].[N;H0;D1;+0:4]#[C;H0;D2;+0:5]-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:5]1:[n;H0;D2;+0:4]:[n;H0;D2;+0:2]:[n;H0;D2;+0:1]:[nH;D2;+0:3]:1):[c:9]:[c:10] | 70.7 | [{"value": 70.7, "product": "C(C)(C)(C)C1=CC=C(C=C1)C1=NN=NN1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a 250 ml round-bottomed flask fitted with reflux condenser, 4.9 g of p-t-butylbenzonitrile, 3.82 g of lithium chloride and 5.85 g of sodium azide and 8.2 g of triethylammonium bromide in 100 ml of DMF are heated at 120° C. for 8 hours. After cooling to room temperature, 100 ml of water are added and the mixture is a... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | null | null | c1nnn[nH]1 | c1ccccc1.c1nnn[nH]1 | null | O.CN(C)C=O | null | null | CC(C)(C)c1ccc(C#N)cc1.[N-]=[N+]=[N-]>O.CN(C)C=O>CC(C)(C)c1ccc(-c2nnn[nH]2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ed73b4098a7f4774a0f9e99e78a1604d | NCCCCCCCCCCCC(=O)O>>NCCCCCCCCCCCC(=O)[O-].[NH4+] | NCCCCCCCCCCCC(=O)O.Cl>>NCCCCCCCCCCCC(=O)[O-].[NH4+] | [NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13](=[O:14])[OH:15]>>[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13](=[O:14])[O-:15].[NH4+:16] | NCCCCCCCCCCCC(=O)O | NCCCCCCCCCCCC(=O)[O-].[NH4+] | null | null | O | Miscellaneous | Carboxylic acid to carboxylate | 3c53722c63fd30e780f359165c19bae99608549d2498be52386c63534c90fc74 | 2464b583d940c451c00c1488740fdde63610bb85f8f9a614db893662c6ccb8a2 | null | [C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4]>>[C:1]-[C:2](-[O-;H0;D1:4])=[O;D1;H0:3] | null | [] | null | null | 5 | MINUTE | In 10 liter of water was dispersed 100 g of montmorillonite having an average thickness of 9.5 Å as one unit of a layered silicate and an average side length of about 0.1 μm, followed by the addition of 51.2 g of 12-aminododecanoic acid and 24 ml of concentrated hydrochloric acid. After dispersion for 5 minutes and fil... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | null | null | null | null | Other | O | null | 0.083333 | NCCCCCCCCCCCC(=O)O>O>NCCCCCCCCCCCC(=O)[O-].[NH4+] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3c966fe269e1451a867618710487421e | O=C(Cl)CCl.O=[N+]([O-])c1ccc(N2CCCNCC2)cc1>>O=C(CCl)N1CCCN(c2ccc([N+](=O)[O-])cc2)CC1 | [N+](=O)([O-])C1=CC=C(C=C1)N1CCNCCC1.C([O-])([O-])=O.[K+].[K+].ClCC(=O)Cl>>ClCC(=O)N1CCN(CCC1)C1=CC=C(C=C1)[N+](=O)[O-] | Cl[C:2](=[O:1])[CH2:3][Cl:4].[NH:5]1[CH2:6][CH2:7][CH2:8][N:9]([c:10]2[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18]2)[CH2:19][CH2:20]1>>[O:1]=[C:2]([CH2:3][Cl:4])[N:5]1[CH2:6][CH2:7][CH2:8][N:9]([c:10]2[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18]2)[CH2:19][CH2:20]1 | O=C(Cl)CCl.O=[N+]([O-])c1ccc(N2CCCNCC2)cc1 | O=C(CCl)N1CCCN(c2ccc([N+](=O)[O-])cc2)CC1 | null | null | CN(C=O)C | Acylation | N-alkylation of secondary amines with alkyl halides | c5087ab4d6515fdee9f2fafb8a1a4cef63670a261dd2f06558dd18e4dcb6c3dd | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | c1ccc(N2CCCNCC2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Cl;D1;H0:4].[#7:5]-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[#7:5]-[C:6]-[C:7]-[N;H0;D3;+0:8](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Cl;D1;H0:4])-[C:9]-[C:10] | 75.2 | [{"value": 75.0, "product": "ClCC(=O)N1CCN(CCC1)C1=CC=C(C=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.2, "product": "ClCC(=O)N1CCN(CCC1)C1=CC=C(C=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 22.1 g (0.1 mol) of 1-(4-nitrophenyl)[1,4]diazepane, 8.3 g (0.06 mol) of potassium carbonate and 120 ml of dimethylformamide were mixed together in a reactor. 8.3 ml (0.11 mol) of chloroacetyl chloride were added to this stirred suspension, while maintaining the temperature between 15 and 25° C. After stirring for abou... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | C1CNCC[NH]C1 | C1C[NH]CC[NH]C1 | C1C[NH]CC[NH]C1.c1ccccc1 | HCl | CN(C=O)C | null | null | O=C(Cl)CCl.O=[N+]([O-])c1ccc(N2CCCNCC2)cc1>CN(C=O)C>O=C(CCl)N1CCCN(c2ccc([N+](=O)[O-])cc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b451781cf2db439e9c0839b785c14df4 | O=C1C=CC(=O)O1.OO.[K+]>>O=C([O-])C1OC1C(=O)[O-].[K+] | [OH-].[K+].C1(\C=C/C(=O)O1)=O.[OH-].[K+].O.OO>>O1C(C(=O)[O-])C1C(=O)[O-].[K+].[K+] | [O:1]=[C:2]1[O:3][C:7](=[O:8])[CH:6]=[CH:4]1.[OH:5][OH:9].[K+:11]>>[O:1]=[C:2]([O-:3])[CH:4]1[O:5][CH:6]1[C:7](=[O:8])[O-:9].[K+:11] | O=C1C=CC(=O)O1.OO.[K+] | O=C([O-])C1OC1C(=O)[O-].[K+] | null | [O-][W](=O)(=O)[O-].[Na+].[Na+] | O | Acylation | OtherReaction | 997b4e6d0c13834e5e0b0311de0eb59fc915f91b6f004aebd8f8235457c70084 | 526e061233a66acb62ff290f1bb837ed763966da1ffa26efef1a72bfd85e420a | C1CO1 | [O;D1;H0:1]=[C:2]1-[CH;D2;+0:3]=[CH;D2;+0:4]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[O;H0;D2;+0:7]-1.[OH;D1;+0:8]-[OH;D1;+0:9]>>[O-;H0;D1:7]-[C:2](=[O;D1;H0:1])-[CH;D3;+0:3]1-[O;H0;D2;+0:8]-[CH;D3;+0:4]-1-[C;H0;D3;+0:5](-[O-;H0;D1:9])=[O;D1;H0:6] | null | [] | null | null | 30 | MINUTE | A 2-liter three-neck flask was charged with 280 g of maleic anhydride and 428 ml of ultrapure water for dissolution. To the aqueous solution, 500 g of 48 wt % potassium hydroxide aqueous solution was added dropwise using a dropping funnel with cooling to keep the temperature at room temperature. Then, 18.8 g of sodium ... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Peroxide | Ether | C1=CCOC1 | C1CO1 | C1CO1 | null | [O-][W](=O)(=O)[O-].[Na+].[Na+].O | null | 0.5 | O=C1C=CC(=O)O1.OO.[K+]>[O-][W](=O)(=O)[O-].[Na+].[Na+].O>O=C([O-])C1OC1C(=O)[O-].[K+] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c210b05912fa4f4d9b61659fee74c384 | c1ccc2ccccc2c1>>c1ccc2ccccc2c1 | C(C=C)#N.[Na][Na].C1=CC=CC2=CC=CC=C12.[Na]>>C1=CC=CC2=CC=CC=C12.[Na] | [cH:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[cH:11]1>>[cH:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[cH:11]1 | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | null | null | C1CCOC1.O1CCCC1.C1=CC=CC=C1 | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc2ccccc2c1 | null | null | [] | null | null | null | null | In this example, a triblock copolymer (PAN-PEO-PAN) consisting of polyethylene oxide (PEO) chain and polyacrylonitrile (PAN) chains is synthesized by living anion polymerization. Using a polyethylene oxide macromer (disodium salt of polyethylene oxide) as a reaction initiator, acrylonitrile is polymerized. Tetrahydrofu... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccc2ccccc2c1 | null | C1CCOC1.O1CCCC1.C1=CC=CC=C1 | null | null | c1ccc2ccccc2c1>C1CCOC1.O1CCCC1.C1=CC=CC=C1>c1ccc2ccccc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-08a08e084a414c518c9108c5bc2b198d | Clc1nccc2ccccc12.OB(O)c1ccc(F)cc1F>>Fc1ccc(-c2nccc3ccccc23)c(F)c1 | C([O-])([O-])=O.[K+].[K+].FC1=C(C=CC(=C1)F)B(O)O.ClC1=NC=CC2=CC=CC=C12.O>>FC1=C(C=CC(=C1)F)C1=NC=CC2=CC=CC=C12 | Cl[c:6]1[n:7][cH:8][cH:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]12.OB(O)[c:5]1[cH:4][cH:3][c:2]([F:1])[cH:18][c:16]1[F:17]>>[F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][cH:8][cH:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]23)[c:16]([F:17])[cH:18]1 | Clc1nccc2ccccc12.OB(O)c1ccc(F)cc1F | Fc1ccc(-c2nccc3ccccc23)c(F)c1 | null | null | C(OC)COC | C-C Coupling | Suzuki coupling with boronic acids | ab2aaaf8707c5adff29c0179e7d715dcbad9e03f443bbbd632f4fce58e2cd5dc | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2nccc3ccccc23)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](:[c:5]):[c:6].O-B(-O)-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10](-[F;D1;H0:11]):[c:12]>>[F;D1;H0:11]-[c:10](:[c:12]):[c;H0;D3;+0:7](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](:[c:5]):[c:6]):[c:8]:[c:9] | null | [] | null | null | null | null | 2,4-difluorophenylboronic acid (Aldrich Chemical Co., 13.8 g, 87.4 mmol), 1-chloroisoquinoline (Adrich Chemical Co., 13 g, 79.4 mmol), tetrakistriphenylphosphine palladium(0) (Aldrich, 3.00 g, 2.59 mmol), potassium carbonate (EM Science, 24.2 g, 175 mmol), water (300 mL), and dimethoxyethane (Aldrich, 300 mL) were allo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2cnccc2c1.c1ccccc1 | c1ccccc1.c1ccc2cnccc2c1 | c1ccccc1.c1ccc2cnccc2c1 | HCl.B | C(OC)COC | null | null | Clc1nccc2ccccc12.OB(O)c1ccc(F)cc1F>C(OC)COC>Fc1ccc(-c2nccc3ccccc23)c(F)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-104ff321bab547fca24b0966005c6059 | NNc1ccccc1.O=Cc1ccc(N(c2ccccc2)c2ccccc2)cc1>>C(=NNc1ccccc1)c1ccc(N(c2ccccc2)c2ccccc2)cc1 | C1(=CC=CC=C1)NN.C1(=CC=CC=C1)N(C1=CC=C(C=O)C=C1)C1=CC=CC=C1>>C1(=CC=CC=C1)NN=CC1=CC=C(C=C1)N(C1=CC=CC=C1)C1=CC=CC=C1 | [NH2:2][NH:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1.O=[CH:1][c:10]1[cH:11][cH:12][c:13]([N:14]([c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[cH:27][cH:28]1>>[CH:1](=[N:2][NH:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[c:10]1[cH:11][cH:12][c:13]([N:14]([c:15]2[cH:16][cH:17][cH:18][... | NNc1ccccc1.O=Cc1ccc(N(c2ccccc2)c2ccccc2)cc1 | C(=NNc1ccccc1)c1ccc(N(c2ccccc2)c2ccccc2)cc1 | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | OtherReaction | c78be09cf200f3a07b02946ce0bbc22b647e9aaae7494d0480373904a4f330a9 | c3cbc07b90655a7aa9777b584274a03a2ec0cff34c5b5edc214a16916fe29f1c | C(=NNc1ccccc1)c1ccc(N(c2ccccc2)c2ccccc2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[#7:6]-[c:7]>>[c:3]:[c:2](-[CH;D2;+0:1]=[N;H0;D2;+0:5]-[#7:6]-[c:7]):[c:4] | null | [] | null | null | null | null | Phenylhydrazine (0.1 mole, commercially available from Aldrich, Milwaukee, Wis.) and 4-(Diphenylamino)benzaldehyde (0.1 mole, available from Fluka, Buchs SG, Switzerland) were dissolved in 100 ml of isopropanol in a 250 ml 3-neck round bottom flask equipped with a reflux condenser and a mechanical stirrer. The solution... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Aldehyde | Hydrazone | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | C(C)(C)O | null | null | NNc1ccccc1.O=Cc1ccc(N(c2ccccc2)c2ccccc2)cc1>C(C)(C)O>C(=NNc1ccccc1)c1ccc(N(c2ccccc2)c2ccccc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-16b8d96509494fc685582f67e77bc1c8 | CCn1c2ccccc2c2cc(C=O)ccc21.NNc1ccccc1>>CCn1c2ccccc2c2cc(C=NNc3ccccc3)ccc21 | C1(=CC=CC=C1)NN.C(C)N1C2=CC=CC=C2C=2C=C(C=CC12)C=O>>C1(=CC=CC=C1)NN=CC=1C=CC=2N(C3=CC=CC=C3C2C1)CC | O=[CH:13][c:12]1[cH:11][c:10]2[c:9]3[c:4]([n:3]([CH2:2][CH3:1])[c:24]2[cH:23][cH:22]1)[cH:5][cH:6][cH:7][cH:8]3.[NH2:14][NH:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[CH3:1][CH2:2][n:3]1[c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[c:10]2[cH:11][c:12]([CH:13]=[N:14][NH:15][c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[cH:22... | CCn1c2ccccc2c2cc(C=O)ccc21.NNc1ccccc1 | CCn1c2ccccc2c2cc(C=NNc3ccccc3)ccc21 | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | OtherReaction | c78be09cf200f3a07b02946ce0bbc22b647e9aaae7494d0480373904a4f330a9 | c3cbc07b90655a7aa9777b584274a03a2ec0cff34c5b5edc214a16916fe29f1c | C(=NNc1ccccc1)c1ccc2[nH]c3ccccc3c2c1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[#7:6]-[c:7]>>[c:3]:[c:2](-[CH;D2;+0:1]=[N;H0;D2;+0:5]-[#7:6]-[c:7]):[c:4] | null | [] | null | null | null | null | Phenylhydrazine (0.1 mole, commercially available from Aldrich, Milwaukee, Wis.) and 9-ethyl-3-carbazolecarboxaldehyde (0.1 mole, available from Aldrich Chemical, Milwaukee, Wis.) were dissolved in 100 ml of isopropanol in 250 ml 3-neck round bottom flask equipped with a reflux condenser and a mechanical stirrer. The s... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Aldehyde | Hydrazone | null | null | c1ccc2[nH]c3ccccc3c2c1.c1ccccc1 | HO- | C(C)(C)O | null | null | CCn1c2ccccc2c2cc(C=O)ccc21.NNc1ccccc1>C(C)(C)O>CCn1c2ccccc2c2cc(C=NNc3ccccc3)ccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2097f911925e48489697293205fe793e | CCn1c2ccccc2c2ccccc21.CN(C)C=O.CN(C)C=O>>CCn1c2ccc(C=O)cc2c2cc(C=O)ccc21 | O=P(Cl)(Cl)Cl.C(C)(=O)[O-].[Na+].O=P(Cl)(Cl)Cl.CN(C)C=O.O=P(Cl)(Cl)Cl.C(C)N1C2=CC=CC=C2C=2C=CC=CC12.CN(C)C=O>>C(C)N1C2=CC=C(C=C2C=2C=C(C=CC12)C=O)C=O | [CH3:1][CH2:2][n:3]1[c:4]2[cH:5][cH:6][cH:7][cH:10][c:11]2[c:12]2[cH:13][cH:14][cH:17][cH:18][c:19]12.CN(C)[CH:8]=[O:9].CN(C)[CH:15]=[O:16]>>[CH3:1][CH2:2][n:3]1[c:4]2[cH:5][cH:6][c:7]([CH:8]=[O:9])[cH:10][c:11]2[c:12]2[cH:13][c:14]([CH:15]=[O:16])[cH:17][cH:18][c:19]12 | CCn1c2ccccc2c2ccccc21.CN(C)C=O.CN(C)C=O | CCn1c2ccc(C=O)cc2c2cc(C=O)ccc21 | null | null | O | C-C Coupling | OtherReaction | 3e08aa519943f228f4f0de61c4108e88d091dcbcd55259c2eac05977b60a9b5e | 59ce066e7b8c6f336ca41b927aa062bd1627961fbe091dda435cb86e18ca36b8 | c1ccc2c(c1)[nH]c1ccccc12 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].C-N(-C)-[CH;D2;+0:3]=[O;D1;H0:4].[#7;a:5]1:[c:6]2:[c:7]:[c:8]:[cH;D2;+0:9]:[c:10]:[c:11]:2:[c:12]2:[c:13]:[cH;D2;+0:14]:[c:15]:[c:16]:[c:17]:1:2>>[O;D1;H0:4]=[CH;D2;+0:3]-[c;H0;D3;+0:9]1:[c:10]:[c:11]2:[c:12]3:[c:13]:[c;H0;D3;+0:14](-[CH;D2;+0:1]=[O;D1;H0:2]):[c:15]:[c:16]:[c:17]:3:[#7;... | 46 | [{"value": 46.0, "product": "C(C)N1C2=CC=C(C=C2C=2C=C(C=CC12)C=O)C=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A 271 ml quantity of DMF (3.5 mol) was added to a 1-liter, 3-neck round bottom flask equipped with a mechanical stirrer, a thermometer, and an addition funnel. The contents were cooled in a salt/ice bath. When the temperature inside the flask reached 0° C., 326 ml of POCl3 (3.5 mol) was slowly added. During the additio... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aldehyde.Aldehyde | c1ccc2c(c1)[nH]c1ccccc12 | c1ccc2[nH]c3ccccc3c2c1 | c1ccc2[nH]c3ccccc3c2c1 | Other | O | null | 3 | CCn1c2ccccc2c2ccccc21.CN(C)C=O.CN(C)C=O>O>CCn1c2ccc(C=O)cc2c2cc(C=O)ccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-44ea98a32567491b9505acc3b6c47bd9 | CCn1c2ccc(C=O)cc2c2cc(C=O)ccc21.NNc1ccccc1>>CCn1c2ccc(C=NNc3ccccc3)cc2c2cc(C=NNc3ccccc3)ccc21 | C1(=CC=CC=C1)NN.C(C)N1C2=CC=C(C=C2C=2C=C(C=CC12)C=O)C=O>>C1(=CC=CC=C1)NN=CC=1C=C2C=3C=C(C=CC3N(C2=CC1)CC)C=NNC1=CC=CC=C1 | O=[CH:8][c:7]1[cH:6][cH:5][c:4]2[n:3]([CH2:2][CH3:1])[c:33]3[c:19]([c:18]2[cH:17]1)[cH:20][c:21]([CH:22]=O)[cH:31][cH:32]3.[NH2:9][NH:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[CH3:1][CH2:2][n:3]1[c:4]2[cH:5][cH:6][c:7]([CH:8]=[N:9][NH:10][c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[cH:17][c:18]2[c:19]2[cH:20][c:... | CCn1c2ccc(C=O)cc2c2cc(C=O)ccc21.NNc1ccccc1 | CCn1c2ccc(C=NNc3ccccc3)cc2c2cc(C=NNc3ccccc3)ccc21 | null | null | C1CCOC1.C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | 5f2b911cac377c45ef69e327a67d7f9de2a3e96ded382f28a32996cfe1440e39 | f8e5c447c32ba2040a9986aace1ce0fddbed56992d363bdc1ff4ba8fc5fc808a | C(=NNc1ccccc1)c1ccc2[nH]c3ccc(C=NNc4ccccc4)cc3c2c1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].O=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8].[NH2;D1;+0:9]-[#7:10]-[c:11]>>[#7:12]-[#7:13]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[c:11]-[#7:10]-[N;H0;D2;+0:9]=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | null | null | Phenylhydrazine (0.2 mole, commercially available from Aldrich, Milwaukee, Wis.) and N-ethyl-3,6-diformylcarbazole (0.1 mole) were dissolved in 100 ml of a 1:1 v/v mixture of toluene and THF in 250 ml 3-neck round bottom flask equipped with a reflux condenser and a mechanical stirrer. The solution was refluxed for 2 ho... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Aldehyde.Aldehyde | Hydrazone.Hydrazone | null | c1ccccc1 | c1ccccc1.c1ccc2[nH]c3ccccc3c2c1.c1ccccc1 | null | C1CCOC1.C1(=CC=CC=C1)C | null | null | CCn1c2ccc(C=O)cc2c2cc(C=O)ccc21.NNc1ccccc1>C1CCOC1.C1(=CC=CC=C1)C>CCn1c2ccc(C=NNc3ccccc3)cc2c2cc(C=NNc3ccccc3)ccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8fe6bddacc26436f8cb0cdefef91e51f | CCN(CC)CC>>CCC1OC1=O | C(C)N(CC)CC.C(C(=C)C)(=O)O.C(C)N(CC)CC.C(C)N(CC)CC>>C(C(=C)C)(=O)O.C1(C(CC)O1)=O | CCN([CH2:8][CH3:7])[CH2:11][CH3:9]>>[CH3:7][CH2:8][CH:9]1[O:10][C:11]1=[O:12] | CCN(CC)CC | CCC1OC1=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | d9690fa18ac691b937cacf0fdee10d405aff81820013e7554df49f3f6377f2c2 | a6bd915431bdb40b472760327522a40e245465502f8cc8de247da1a21784e060 | O=C1CO1 | C-C-N(-[CH2;D2;+0:1]-[CH3;D1;+0:2])-[CH2;D2;+0:3]-[C;D1;H3:4]>>[C;D1;H3:4]-[CH2;D2;+0:3]-[CH;D3;+0:2]1-[#8:5]-[C;H0;D3;+0:1]-1=[O;D1;H0:6] | 85.6 | [{"value": 85.6, "product": "C(C(=C)C)(=O)O.C1(C(CC)O1)=O", "details": "PERCENTYIELD", "is_desired": false}] | 55 | CELSIUS | 20 | MINUTE | To a 250 ml 3N-RB flask fitted with a gas inlet, thermometer, overhead stirrer and a 125 ml pressure equalizing dropping funnel was added 26.5 g triethylamine. The triethylamine was cooled to 5° C. using a water/ice bath. Once the triethylamine was at 5° C. the methacrylic acid was added dropwise over a 20–25 min perio... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Ether | null | C1CO1 | C1CO1 | Other | null | 55 | 0.333333 | CCN(CC)CC>>CCC1OC1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8f56d2638ebd4d958343cc0fd1c539ea | C=C(C)C(=O)O.C=C(C)C(=O)OC12CC3CC(CC(C3)C1C)C2>>C=C(C)C(=O)O.CC(=CC12CC3CC(CC(C3)C1C)C2)C(=O)[O-] | C(C(=C)C)(=O)OC12C(C3CC(CC(C1)C3)C2)C.C(C(=C)C)#N.C(C(=C)C)(=O)O.C1(C(CC)O1)=O.CCC(C)(C#N)N=NC(C)(CC)C#N>>CC1C2(CC3CC(CC1C3)C2)C=C(C(=O)[O-])C.C(C(=C)C)#N.C(C(=C)C)(=O)O.C1(C(CC)O1)=O | [CH3:12][C:13](=[CH2:14])[C:26](=[O:27])[OH:28].[CH2:6]=[C:7]([CH3:8])[C:9](=[O:10])[O:11][C:15]12[CH2:16][CH:17]3[CH2:18][CH:19]([CH2:20][CH:21]([CH2:22]3)[CH:23]1[CH3:24])[CH2:25]2>>[CH2:6]=[C:7]([CH3:8])[C:9](=[O:10])[OH:11].[CH3:12][C:13](=[CH:14][C:15]12[CH2:16][CH:17]3[CH2:18][CH:19]([CH2:20][CH:21]([CH2:22]3)[CH... | C=C(C)C(=O)O.C=C(C)C(=O)OC12CC3CC(CC(C3)C1C)C2 | C=C(C)C(=O)O.CC(=CC12CC3CC(CC(C3)C1C)C2)C(=O)[O-] | null | null | O1CCCC1 | C-C Coupling | OtherReaction | d7487757ec61706cf62d444e87e8e18b8c68a1cede2f57370c181071606b6da4 | e7c3a7be3a7623a33022d587a29f3932da427299bd94d4fb2a6e325383b9e8a7 | C1C2CC3CC1CC(C2)C3 | [C;D1;H3:1]-[C:2](=[CH2;D1;+0:3])-[C:4](=[O;D1;H0:5])-[OH;D1;+0:6].[C:7]-[C:8]-[C;H0;D4;+0:9](-[O;H0;D2;+0:10]-[C:11](=[O;D1;H0:12])-[C:13](=[C;D1;H2:14])-[C;D1;H3:15])(-[C:16]-[C:17])-[C:18](-[C;D1;H3:19])-[C:20]>>[C;D1;H2:14]=[C:13](-[C;D1;H3:15])-[C:11](=[O;D1;H0:12])-[OH;D1;+0:10].[C:7]-[C:8]-[C;H0;D4;+0:9](-[CH;D2... | null | [] | 90 | CELSIUS | 20 | HOUR | 2-Methyladamantanyl methacrylate (14.21 g, 0.061 mol), methacrylonitrile (3.05 g, 0.045 mol), and alpha-butyrolactone methacrylate (7.74 g, 0.045 mol) were dissolved in 66 mL of tetrahydrofuran. The resulting colorless solution was deoxygenated by gently bubbling a stream of N2 through the stirring solution for 15 minu... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester.Vinyl | Carboxylic acid | C1C2CC3CC1CC(C2)C3 | C1C2CC3CC1CC(C2)C3 | C1C2CC3CC1CC(C2)C3 | null | O1CCCC1 | 90 | 20 | C=C(C)C(=O)O.C=C(C)C(=O)OC12CC3CC(CC(C3)C1C)C2>O1CCCC1>C=C(C)C(=O)O.CC(=CC12CC3CC(CC(C3)C1C)C2)C(=O)[O-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-89b17b9dd0da4212841faec9d0e20031 | CCOC(=O)C(Cc1ccc(O)cc1)OCC>>CCO[C@@H](Cc1ccc(O)cc1)C(=O)O | C(C)OC(C(=O)OCC)CC1=CC=C(C=C1)O.[OH-].[Na+]>>C(C)O[C@H](C(=O)O)CC1=CC=C(C=C1)O | CC[O:15][C:13]([CH:4]([O:3][CH2:2][CH3:1])[CH2:5][c:6]1[cH:7][cH:8][c:9]([OH:10])[cH:11][cH:12]1)=[O:14]>>[CH3:1][CH2:2][O:3][C@@H:4]([CH2:5][c:6]1[cH:7][cH:8][c:9]([OH:10])[cH:11][cH:12]1)[C:13](=[O:14])[OH:15] | CCOC(=O)C(Cc1ccc(O)cc1)OCC | CCO[C@@H](Cc1ccc(O)cc1)C(=O)O | null | null | P(=O)([O-])([O-])[O-] | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 40.8 | [{"value": 40.8, "product": "C(C)O[C@H](C(=O)O)CC1=CC=C(C=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | Ethyl (2R/S) (+/−) 2-ethoxy-3-(4-hydroxyphenyl)propanoate (5 g) was added to an aqueous 0.1 M phosphate buffer pH 7 (10 ml). 100 mg of the lyophilised esterase preparation from Aspergillus oryzae was added and the mixture was stirred for 18 hours at room temperature. During that time, the pH of the reaction mixture was... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | P(=O)([O-])([O-])[O-] | null | 18 | CCOC(=O)C(Cc1ccc(O)cc1)OCC>P(=O)([O-])([O-])[O-]>CCO[C@@H](Cc1ccc(O)cc1)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4b81f1ce1541441e9e0308b3437158fb | CCOC(=O)C(Cc1ccc(O)cc1)OCC>>CCO[C@@H](Cc1ccc(O)cc1)C(=O)O | C(C)OC(C(=O)OCC)CC1=CC=C(C=C1)O.[OH-].[Na+]>>C(C)O[C@H](C(=O)O)CC1=CC=C(C=C1)O | CC[O:15][C:13]([CH:4]([O:3][CH2:2][CH3:1])[CH2:5][c:6]1[cH:7][cH:8][c:9]([OH:10])[cH:11][cH:12]1)=[O:14]>>[CH3:1][CH2:2][O:3][C@@H:4]([CH2:5][c:6]1[cH:7][cH:8][c:9]([OH:10])[cH:11][cH:12]1)[C:13](=[O:14])[OH:15] | CCOC(=O)C(Cc1ccc(O)cc1)OCC | CCO[C@@H](Cc1ccc(O)cc1)C(=O)O | null | null | P(=O)([O-])([O-])[O-] | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 40.8 | [{"value": 40.8, "product": "C(C)O[C@H](C(=O)O)CC1=CC=C(C=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | In another experiment, ethyl (2R/S) (+/−) 2-ethoxy-3-(4-hydroxyphenyl)propanoate (5 g) was added to an aqueous 0.1 M phosphate buffer pH 7 (10 ml). 100 mg of the lyophilised hydrolytic enzyme mixture from Aspergillus oryzae was added and the mixture was stirred for 18 hours at room temperature. During that time, the pH... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | P(=O)([O-])([O-])[O-] | null | 18 | CCOC(=O)C(Cc1ccc(O)cc1)OCC>P(=O)([O-])([O-])[O-]>CCO[C@@H](Cc1ccc(O)cc1)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-abb76655ac01447ea0ff9d306d69fe0b | CC1C=CCC(C)(C)C1CC=O.CC=O>>CC=CC(=O)C1C(C)C=CCC1(C)C | O.CC1C(C(CC=C1)(C)C)CC=O.C(C)=O.C(C)(=O)O>>CC1C(C(CC=C1)(C)C)C(C=CC)=O | [CH:3]([CH2:4][CH:6]1[CH:7]([CH3:8])[CH:9]=[CH:10][CH2:11][C:12]1([CH3:13])[CH3:14])=[O:5].O=[CH:2][CH3:1]>>[CH3:1][CH:2]=[CH:3][C:4](=[O:5])[CH:6]1[CH:7]([CH3:8])[CH:9]=[CH:10][CH2:11][C:12]1([CH3:13])[CH3:14] | CC1C=CCC(C)(C)C1CC=O.CC=O | CC=CC(=O)C1C(C)C=CCC1(C)C | null | null | C(C)(=O)OCCCC | C-C Coupling | OtherReaction | 21db8d37c05aca84b4f073906818d205da271deee49cf0ba6c7250be992af972 | b0501e2687bea7d8a21f333ccfaded99e607958f8cf0f177a5f87c801870e4ba | C1=CCCCC1 | O=[CH;D2;+0:1]-[C;D1;H3:2].[C:3]=[C:4]-[C:5]-[C:6](-[CH2;D2;+0:7]-[CH;D2;+0:8]=[O;H0;D1;+0:9])-[C:10]>>[C:3]=[C:4]-[C:5]-[C:6](-[C;H0;D3;+0:7](=[O;H0;D1;+0:9])-[CH;D2;+0:8]=[CH;D2;+0:1]-[C;D1;H3:2])-[C:10] | null | [] | 100 | CELSIUS | null | null | In a 250 ml flask were added 30 g (0.18 mole) of 1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-2-ethanone (94% purity), 12.0 g of butyl acetate, an aliquot according to Table 1 of the catalytic solution as prepared above and a quantity of co-ingredient according to Table 1. The resulting mixture was stirred at 100° C. To said ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Aldehyde | Ketone | null | null | C1=CCCCC1 | HO- | C(C)(=O)OCCCC | 100 | null | CC1C=CCC(C)(C)C1CC=O.CC=O>C(C)(=O)OCCCC>CC=CC(=O)C1C(C)C=CCC1(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bfaaa2dc17da42f6b989cc71db7aee74 | C=CC=C>>C=CC=C | C=CC(C)=C.C=CC=C>>C=CC(C)=C.C=CC=C | [CH2:6]=[CH:7][CH:8]=[CH2:9]>>[CH2:6]=[CH:7][CH:8]=[CH2:9] | C=CC=C | C=CC=C | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | 21 | MINUTE | In this experiment, a 30/70 isoprene-butadiene rubber (IBR) was prepared using a preformed catalyst described in Example 2. The procedure described in Example 3 was utilized in this examples except that a premix containing a 30:70 mixture of isoprene and 1,3-butadiene was used as the monomers. GC analysis of the residu... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | null | null | 0.35 | C=CC=C>>C=CC=C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-88386b921b3a47c49d55be4d66c9b367 | N.N#CCCCCC#N>>NC1CCCCC1N.NCCCCCCN | C(CCCCC#N)#N.N.[H][H].[O-2].[Al+3].[O-2].[O-2].[Al+3].[Si](=O)=O.[O-2].[Ca+2]>>NCCCCCCN.NC1C(CCCC1)N | [NH3:8].[N:1]#[C:2][CH2:3][CH2:13][CH2:12][CH2:11][C:10]#[N:9]>>[NH2:1][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH:7]1[NH2:8].[NH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][NH2:16] | N.N#CCCCCC#N | NC1CCCCC1N.NCCCCCCN | null | [Fe].[O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] | null | Heteroatom Alkylation and Arylation | OtherReaction | a7b00c3192e2c5629b0edbb1029c4ccba1327dceeb6e5d792b99732663ccd1f8 | e712c8913c20bbaadaf44cd6b3f74ce4977ff23936f031703e775ec360e85b3a | C1CCCCC1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[C:5]-[C:6]-[C;H0;D2;+0:7]#[N;H0;D1;+0:8].[NH3;D0;+0:9]>>[C:10]-[C:11]-[CH2;D2;+0:4]-[C:5]-[C:6]-[CH2;D2;+0:7]-[NH2;D1;+0:8].[NH2;D1;+0:1]-[CH;D3;+0:2]1-[CH2;D2;+0:3]-[C:12]-[C:13]-[C:14]-[C:15]-1-[NH2;D1;+0:9] | 98.22 | [{"value": 98.22, "product": "NCCCCCCN", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | DE-A-2 429 293 discloses in Example 1 that the hydrogenation of adiponitrile in the presence of five times the weight of ammonia at from 93 to 985 C (inlet temperature into the reactor) or at from 94 to 1045 C (outlet temperature) over an iron catalyst prepared from magnetite by reduction with hydrogen and doped with a... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Nitrile | Primary amine.Primary amine.Primary amine.Primary amine | null | C1CCCCC1 | C1CCCCC1 | Other | [Fe].[O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] | null | null | N.N#CCCCCC#N>[Fe].[O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5]>NC1CCCCC1N.NCCCCCCN |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1970c41b1271414281e712b1f7501bcb | N.N#CCCCCC#N>>NC1CCCCC1N.NCCCCCCN | C(CCCCC#N)#N.N.[H][H].[O-2].[Al+3].[O-2].[O-2].[Al+3].[Si](=O)=O.[O-2].[Ca+2]>>NCCCCCCN.NC1C(CCCC1)N | [NH3:8].[N:1]#[C:2][CH2:3][CH2:13][CH2:12][CH2:11][C:10]#[N:9]>>[NH2:1][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH:7]1[NH2:8].[NH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][NH2:16] | N.N#CCCCCC#N | NC1CCCCC1N.NCCCCCCN | null | [Fe] | null | Heteroatom Alkylation and Arylation | OtherReaction | a7b00c3192e2c5629b0edbb1029c4ccba1327dceeb6e5d792b99732663ccd1f8 | e712c8913c20bbaadaf44cd6b3f74ce4977ff23936f031703e775ec360e85b3a | C1CCCCC1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[C:5]-[C:6]-[C;H0;D2;+0:7]#[N;H0;D1;+0:8].[NH3;D0;+0:9]>>[C:10]-[C:11]-[CH2;D2;+0:4]-[C:5]-[C:6]-[CH2;D2;+0:7]-[NH2;D1;+0:8].[NH2;D1;+0:1]-[CH;D3;+0:2]1-[CH2;D2;+0:3]-[C:12]-[C:13]-[C:14]-[C:15]-1-[NH2;D1;+0:9] | 98.05 | [{"value": 98.05, "product": "NCCCCCCN", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | DE-A-2 429 293 discloses in Example 1 that the hydrogenation of adiponitrile in the presence of five times the weight of ammonia at from 93 to 985 C (inlet temperature into the reactor) or at from 94 to 1045 C (outlet temperature) over an iron catalyst prepared from magnetite by reduction with hydrogen and doped with a... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Nitrile | Primary amine.Primary amine.Primary amine.Primary amine | null | C1CCCCC1 | C1CCCCC1 | Other | [Fe] | null | null | N.N#CCCCCC#N>[Fe]>NC1CCCCC1N.NCCCCCCN |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-347c075934a74b70a106dd279acbdf62 | CCOC(=O)C(=O)CC#N.NNCc1ccccc1F>>CCOC(=O)c1cc(N)n(Cc2ccccc2F)n1 | FC1=C(CNN)C=CC=C1.FC(C(=O)O)(F)F.[Na].C(#N)CC(C(=O)OCC)=O>>NC1=CC(=NN1CC1=C(C=CC=C1)F)C(=O)OCC | O=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][C:8]#[N:9].[NH:10]([CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[F:18])[NH2:19]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([NH2:9])[n:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[F:18])[n:19]1 | CCOC(=O)C(=O)CC#N.NNCc1ccccc1F | CCOC(=O)c1cc(N)n(Cc2ccccc2F)n1 | null | null | O1CCOCC1 | Aromatic Heterocycle Formation | OtherReaction | cf591e97a1a52404df569f8fea947886092af868eabbeda85b62b1a3ba7da8bc | 37fd7b1aed45a12b24520198992519ca682712f5b812d84487524cffc72674b4 | c1ccc(Cn2cccn2)cc1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[C;H0;D2;+0:3]#[N;H0;D1;+0:4])-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8].[NH2;D1;+0:9]-[NH;D2;+0:10]-[C:11]-[c:12]>>[C:8]-[#8:7]-[C:5](=[O;D1;H0:6])-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[c;H0;D3;+0:3](-[NH2;D1;+0:4]):[n;H0;D3;+0:10](-[C:11]-[c:12]):[n;H0;D2;+0:9]:1 | null | [] | null | null | 10 | MINUTE | 111.75 g (75 ml, 0.98 mol) of trifluoroacetic acid are added to 100.00 g (0.613 mol) of the sodium salt of ethyl cyanopyruvate (prepared in analogy to Borsche and Manteuffel, Liebigs Ann. 1934, 512, 97) while stirring efficiently in 2.5 l of dioxane at room temperature under argon, and the mixture is stirred for 10 min... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Ester.Nitrile | Ester.Primary amine | null | c1cc[nH]n1 | c1cc[nH]n1.c1ccccc1 | HO- | O1CCOCC1 | null | 0.166667 | CCOC(=O)C(=O)CC#N.NNCc1ccccc1F>O1CCOCC1>CCOC(=O)c1cc(N)n(Cc2ccccc2F)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2089e7109b4c498594f3f7ea1206c5d4 | N#Cc1nn(Cc2ccccc2F)c2ncccc12.[NH4+]>>N=C(N)c1nn(Cc2ccccc2F)c2ncccc12 | C(C)(=O)O.C(#N)C1=NN(C2=NC=CC=C21)CC2=C(C=CC=C2)F.C[O-].[Na+].[Cl-].[NH4+]>>FC1=C(CN2N=C(C=3C2=NC=CC3)C(N)=N)C=CC=C1 | [N:1]#[C:2][c:4]1[n:5][n:6]([CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[F:14])[c:15]2[n:16][cH:17][cH:18][cH:19][c:20]12.[NH4+:3]>>[NH:1]=[C:2]([NH2:3])[c:4]1[n:5][n:6]([CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[F:14])[c:15]2[n:16][cH:17][cH:18][cH:19][c:20]12 | N#Cc1nn(Cc2ccccc2F)c2ncccc12.[NH4+] | N=C(N)c1nn(Cc2ccccc2F)c2ncccc12 | null | null | CO | Functional Group Addition | OtherReaction | b3aaef1538bea73aa85740ccbb089c1b6ca4b164a10fd32235acb6c78d1de6d9 | d1a81d2cc57b1a744f94f80261b8629cf532e8b73012860cc8db4db5903fee1a | c1ccc(Cn2ncc3cccnc32)cc1 | [#7;a:1]:[c:2]1:[c:3]:[c:4](-[C;H0;D2;+0:5]#[N;H0;D1;+0:6]):[#7;a:7]:[#7;a:8]:1-[C:9].[NH4+;D0:10]>>[#7;a:1]:[c:2]1:[c:3]:[c:4](-[C;H0;D3;+0:5](-[NH2;D1;+0:10])=[NH;D1;+0:6]):[#7;a:7]:[#7;a:8]:1-[C:9] | null | [] | null | null | 2 | HOUR | 108.00 g (0.43 mol) of 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carbonitrile (example I, step 4) are dissolved in one liter of methanol and added dropwise to a solution of 94.73 g (1.67 mol; purity: 95%) of sodium methoxide in 3 l of methanol. After stirring at RT for 2 hours, 28.83 g (0.54 mol) of ammonium chlo... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccccc1.c1[nH]nc2ncccc12 | null | CO | null | 2 | N#Cc1nn(Cc2ccccc2F)c2ncccc12.[NH4+]>CO>N=C(N)c1nn(Cc2ccccc2F)c2ncccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-25e6eef647224e5c809a178690dcb286 | N=C(N)c1nn(Cc2ccccc2F)c2ncccc12.O=CC(Br)C=O>>Fc1ccccc1Cn1nc(-c2ncc(Br)cn2)c2cccnc21 | BrC(C=O)C=O.FC1=C(CN2N=C(C=3C2=NC=CC3)C(N)=N)C=CC=C1>>BrC=1C=NC(=NC1)C1=NN(C2=NC=CC=C21)CC2=C(C=CC=C2)F | [F:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH2:8][n:9]1[n:10][c:11]([C:12](=[NH:13])[NH2:18])[c:19]2[cH:20][cH:21][cH:22][n:23][c:24]12.O=[CH:14][CH:15]([Br:16])[CH:17]=O>>[F:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH2:8][n:9]1[n:10][c:11](-[c:12]2[n:13][cH:14][c:15]([Br:16])[cH:17][n:18]2)[c:19]2[cH:20][cH:21][cH:22][n:... | N=C(N)c1nn(Cc2ccccc2F)c2ncccc12.O=CC(Br)C=O | Fc1ccccc1Cn1nc(-c2ncc(Br)cn2)c2cccnc21 | null | null | C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 433634ad2248cb5d908bf41c85756b2375feef4eebabc64f8b6aafe61d1af2b6 | a93805e04cc8dd14ac1dcf6fd44f35b336dc99c8be7299d44004d554881927e7 | c1ccc(Cn2nc(-c3ncccn3)c3cccnc32)cc1 | O=[CH;D2;+0:1]-[CH;D3;+0:2](-[Br;D1;H0:3])-[CH;D2;+0:4]=O.[C:5]-[#7;a:6]1:[#7;a:7]:[c;H0;D3;+0:8](-[C;H0;D3;+0:9](-[NH2;D1;+0:10])=[NH;D1;+0:11]):[c:12](:[c:13]):[c:14]:1:[#7;a:15]:[c:16]>>[Br;D1;H0:3]-[c;H0;D3;+0:2]1:[cH;D2;+0:1]:[n;H0;D2;+0:11]:[c;H0;D3;+0:9](-[c;H0;D3;+0:8]2:[#7;a:7]:[#7;a:6](-[C:5]):[c:14](:[#7;a:1... | null | [] | 100 | CELSIUS | 2 | HOUR | 10.09 g (66.84 mmol) of 2-bromomalonaldehyde are added to a solution of 15.00 g (55.70 mmol) of 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboximidamide (example I, step 5) in 200 ml of glacial acetic acid and stirring at 100° C. for 2 hours. The solvent is removed in vacuo. The residue is purified by chromatogr... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aldehyde.Aldehyde.Primary amine | Aromatic halide | null | c1cncnc1 | c1ccccc1.c1cncnc1.c1n[nH]c2ncccc12 | HO- | C(C)(=O)O | 100 | 2 | N=C(N)c1nn(Cc2ccccc2F)c2ncccc12.O=CC(Br)C=O>C(C)(=O)O>Fc1ccccc1Cn1nc(-c2ncc(Br)cn2)c2cccnc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-29a3d6e0dca643e485207c9d6fad4dea | O=S(=O)(c1ccccc1)N1CC2CN(Cc3ccccc3)CC(C1)O2>>c1ccc(CN2CC3CNCC(C2)O3)cc1 | O.[OH-].[K+].O.C(C1=CC=CC=C1)N1CC2CN(CC(C1)O2)S(=O)(=O)C2=CC=CC=C2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>C(C1=CC=CC=C1)N1CC2CNCC(C1)O2 | O=S(=O)(c1ccccc1)[N:10]1[CH2:9][CH:8]2[CH2:7][N:6]([CH2:5][c:4]3[cH:3][cH:2][cH:1][cH:16][cH:15]3)[CH2:13][CH:12]([CH2:11]1)[O:14]2>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][N:6]2[CH2:7][CH:8]3[CH2:9][NH:10][CH2:11][CH:12]([CH2:13]2)[O:14]3)[cH:15][cH:16]1 | O=S(=O)(c1ccccc1)N1CC2CN(Cc3ccccc3)CC(C1)O2 | c1ccc(CN2CC3CNCC(C2)O3)cc1 | null | null | O1CCCC1 | Reduction | Hydrogenolysis of tertiary amines | 646353ef02af913ec15997219ab07c2b0beab6cc357ed4a1b9097a0efb65c76c | bcb9bfb3b7e1d1e34dc71b339ec9a6091906ae73cd7793ace40af94d3849dabf | c1ccc(CN2CC3CNCC(C2)O3)cc1 | O=S(=O)(-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#8:4]-[C:5]-[C:6]-1)-c1:c:c:c:c:c:1>>[#8:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1 | null | [] | null | null | null | null | 10.00 g (0.25 mol) of lithium aluminum hydride are introduced into 300 ml of absolute tetrahydrofuran and heated to reflux, and 18.00 g (50 mmol) of 7-benzyl-3-phenylsulfonyl-9-oxa-3,7-diazabicyclo[3.3.1]nonane, dissolved in 150 ml of absolute tetrahydrofuran, are added dropwise. The mixture is boiled under reflux for ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.C1[NH]CC2C[NH]CC1O2 | C1NCC2C[NH]CC1O2 | c1ccccc1.C1NCC2C[NH]CC1O2 | HO- | O1CCCC1 | null | null | O=S(=O)(c1ccccc1)N1CC2CN(Cc3ccccc3)CC(C1)O2>O1CCCC1>c1ccc(CN2CC3CNCC(C2)O3)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b92eecbe9f48471a8d576bc9f782095e | CC(C)(C)OC(=O)N1CC2CN(Cc3ccccc3)CC(C1)O2>>CC(C)(C)OC(=O)N1CC2CNCC(C1)O2 | C(C1=CC=CC=C1)N1CC2CN(CC(C1)O2)C(=O)OC(C)(C)C>>C12CN(CC(CNC1)O2)C(=O)OC(C)(C)C | c1ccc(C[N:12]2[CH2:11][CH:10]3[CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:15][CH:14]([CH2:13]2)[O:16]3)cc1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]2[CH2:11][NH:12][CH2:13][CH:14]([CH2:15]1)[O:16]2 | CC(C)(C)OC(=O)N1CC2CN(Cc3ccccc3)CC(C1)O2 | CC(C)(C)OC(=O)N1CC2CNCC(C1)O2 | null | [Pd] | C(C)O | Deprotection | Hydrogenolysis of tertiary amines | 6aa3d05156b632a9956897b2894498b5784bd8bc067b078eb3ebf1317268945a | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | C1NCC2CNCC1O2 | C(-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#8:4]-[C:5]-[C:6]-1)-c1:c:c:c:c:c:1>>[#8:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1 | null | [] | null | null | null | null | 5.60 g (17.6 mmol) of tert-butyl 7-benzyl-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate are dissolved in 100 ml of ethanol, 1.00 g of 10% palladium on activated carbon is added, and hydrogenation is carried out at 100° C. and 100 bar. The catalyst is filtered off with suction, and the filtrate is concentrated, wher... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.C1[NH]CC2C[NH]CC1O2 | C1NCC2C[NH]CC1O2 | C1NCC2C[NH]CC1O2 | Other | [Pd].C(C)O | null | null | CC(C)(C)OC(=O)N1CC2CN(Cc3ccccc3)CC(C1)O2>[Pd].C(C)O>CC(C)(C)OC(=O)N1CC2CNCC(C1)O2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-28fe674f09774641b55817670fb93e9a | OCCNCC1(O)CCN(Cc2ccccc2)C1>>c1ccc(CN2CCCC23CNCCO3)cc1 | C(C1=CC=CC=C1)N1CC(CC1)(CNCCO)O.[OH-].[Na+]>>C(C1=CC=CC=C1)N1C2(CNCCO2)CCC1 | O[C:10]1([CH2:11][NH:12][CH2:13][CH2:14][OH:15])[CH2:8][CH2:7][N:6]([CH2:5][c:4]2[cH:3][cH:2][cH:1][cH:17][cH:16]2)[CH2:9]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][N:6]2[CH2:7][CH2:8][CH2:9][C:10]23[CH2:11][NH:12][CH2:13][CH2:14][O:15]3)[cH:16][cH:17]1 | OCCNCC1(O)CCN(Cc2ccccc2)C1 | c1ccc(CN2CCCC23CNCCO3)cc1 | null | null | O.S(O)(O)(=O)=O | Heteroatom Alkylation and Arylation | OtherReaction | d087c21c2b4884c2f4fc81b98666380f7084052349474b44c69d94a795c5a50a | 2d1b3958f51a08b26adb5b80e5837ae9edf4c86230cd1e7e364ed56aab6934f7 | c1ccc(CN2CCCC23CNCCO3)cc1 | O-[C;H0;D4;+0:1]1(-[C:2]-[#7:3]-[C:4]-[C:5]-[OH;D1;+0:6])-[CH2;D2;+0:7]-[C:8]-[N;H0;D3;+0:9](-[C:10]-[c:11])-[CH2;D2;+0:12]-1>>[c:11]-[C:10]-[N;H0;D3;+0:9]1-[C:8]-[CH2;D2;+0:7]-[CH2;D2;+0:12]-[C;H0;D4;+0:1]-12-[C:2]-[#7:3]-[C:4]-[C:5]-[O;H0;D2;+0:6]-2 | null | [] | 180 | CELSIUS | null | null | 85.0 g (340 mmol) of 1-benzyl-3-hydroxy-3-(2-hydroxyethylaminomethyl)-pyrrolidine are dissolved in a mixture of 280 ml of concentrated sulfuric acid and 140 ml of water and heated at 180° C. overnight. The mixture is made alkaline with 45% strength sodium hydroxide solution, precipitated salts are dissolved in water, a... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Tertiary alcohol.Tertiary amine | Ether.Tertiary amine | C1CC[NH]C1 | C1C[NH]C2(C1)CNCCO2 | c1ccccc1.C1C[NH]C2(C1)CNCCO2 | HO- | O.S(O)(O)(=O)=O | 180 | null | OCCNCC1(O)CCN(Cc2ccccc2)C1>O.S(O)(O)(=O)=O>c1ccc(CN2CCCC23CNCCO3)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-203ff97b1a6344499f1a81b6bc4020cf | CC(C)(C)OC(=O)N1CCOC2(CCCN2Cc2ccccc2)C1>>CC(C)(C)OC(=O)N1CCOC2(CCCN2)C1 | C(C1=CC=CC=C1)N1C2(CN(CCO2)C(=O)OC(C)(C)C)CCC1>>O1CCN(CC12NCCC2)C(=O)OC(C)(C)C | c1ccc(C[N:16]2[C:12]3([O:11][CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:17]3)[CH2:13][CH2:14][CH2:15]2)cc1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][O:11][C:12]2([CH2:13][CH2:14][CH2:15][NH:16]2)[CH2:17]1 | CC(C)(C)OC(=O)N1CCOC2(CCCN2Cc2ccccc2)C1 | CC(C)(C)OC(=O)N1CCOC2(CCCN2)C1 | null | [Pd] | CO | Deprotection | Hydrogenolysis of tertiary amines | 8bfd317babdac0a27e66490c8863b9d15ff187b8b6c37291af647044d7892671 | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | C1CNC2(C1)CNCCO2 | [#7:1]-[C:2]-[C:3]1(-[#8:4]-[C:5])-[C:6]-[C:7]-[C:8]-[N;H0;D3;+0:9]-1-C-c1:c:c:c:c:c:1>>[#7:1]-[C:2]-[C:3]1(-[#8:4]-[C:5])-[C:6]-[C:7]-[C:8]-[NH;D2;+0:9]-1 | null | [] | null | null | null | null | 13.7 g (41 mmol) of tert-butyl 7-benzyl-1-oxa-4,7-diazaspiro[5.4]decane-4-carboxylate are dissolved in 300 ml of methanol, 3.0 g of 10% palladium on activated carbon are added, and hydrogenation is carried out at 100° C. and 100 bar. The catalyst is filtered off with suction, the filtrate is concentrated, and residue i... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.C1C[NH]C2(C1)C[NH]CCO2 | C1CNC2(C1)C[NH]CCO2 | C1CNC2(C1)C[NH]CCO2 | Other | [Pd].CO | null | null | CC(C)(C)OC(=O)N1CCOC2(CCCN2Cc2ccccc2)C1>[Pd].CO>CC(C)(C)OC(=O)N1CCOC2(CCCN2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-116ca2619590407d871a38a12f8418ca | O=C1C=CC(=O)N1.c1ccoc1>>O=C1NC(=O)C2C3CCC(O3)C12 | O1C=CC=C1.C1(C=CC(N1)=O)=O>>C12C3C(NC(C3C(CC1)O2)=O)=O | [O:1]=[C:2]1[NH:3][C:4](=[O:5])[CH:6]=[CH:12]1.[cH:7]1[cH:8][cH:9][cH:10][o:11]1>>[O:1]=[C:2]1[NH:3][C:4](=[O:5])[CH:6]2[CH:7]3[CH2:8][CH2:9][CH:10]([O:11]3)[CH:12]12 | O=C1C=CC(=O)N1.c1ccoc1 | O=C1NC(=O)C2C3CCC(O3)C12 | null | null | null | C-C Coupling | OtherReaction | 0bbfef2818b3d472c668fd12fcafcc8b9bbd90b6adc259410a5a9077224e2cc8 | 41110843b5eb83613b3bc8f414a9f2accf7a121ee6050cca3e0d09d78b8a5071 | O=C1NC(=O)C2C3CCC(O3)C12 | [O;D1;H0:1]=[C:2]1-[#7:3]-[C:4](=[O;D1;H0:5])-[CH;D2;+0:6]=[CH;D2;+0:7]-1.[cH;D2;+0:8]1:[cH;D2;+0:9]:[cH;D2;+0:10]:[cH;D2;+0:11]:[o;H0;D2;+0:12]:1>>[O;D1;H0:1]=[C:2]1-[#7:3]-[C:4](=[O;D1;H0:5])-[CH;D3;+0:6]2-[CH;D3;+0:7]-1-[CH;D3;+0:8]1-[CH2;D2;+0:9]-[CH2;D2;+0:10]-[CH;D3;+0:11]-2-[O;H0;D2;+0:12]-1 | null | [] | null | null | null | null | This compound can be obtained by Diels-Alder reaction of furan with maleimide, for example in analogy to Fisera, L., Melnikov, J., Pronayova, N., Ertl, P., Chem. Pap. 1995, 49 (4), 186–191.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | Ether | C1=CCNC1.c1ccoc1 | C1CC2OC1C1CNCC21 | C1CC2OC1C1CNCC21 | null | null | null | null | O=C1C=CC(=O)N1.c1ccoc1>>O=C1NC(=O)C2C3CCC(O3)C12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a07acd63003445368b57866a2cbc87ec | O=C1NC(=O)C2C3CCC(O3)C12>>C1CC2OC1C1CNCC21 | C12C3C(NC(C3C(CC1)O2)=O)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Na+]>>C12C3CNCC3C(CC1)O2 | O=[C:7]1[CH:6]2[CH:5]3[CH2:1][CH2:2][CH:3]([O:4]3)[CH:10]2[C:9](=O)[NH:8]1>>[CH2:1]1[CH2:2][CH:3]2[O:4][CH:5]1[CH:6]1[CH2:7][NH:8][CH2:9][CH:10]21 | O=C1NC(=O)C2C3CCC(O3)C12 | C1CC2OC1C1CNCC21 | null | null | C1CCOC1 | Reduction | OtherReaction | aac8dd7e4409c434437355e06194cbe7ad87ae4c46ba861757b15c50ca30f2c8 | 59c2ee763b7b622068443754ae5dd863ade167776adae5c559fe5aaf6c5ddfe9 | C1CC2OC1C1CNCC21 | O=[C;H0;D3;+0:1]1-[#7:2]-[C;H0;D3;+0:3](=O)-[C:4]2-[C:5]-[#8:6]-[C:7]-[C:8]-2-1>>[#7:2]1-[CH2;D2;+0:1]-[C:8]2-[C:7]-[#8:6]-[C:5]-[C:4]-2-[CH2;D2;+0:3]-1 | null | [] | 0 | CELSIUS | 8 | HOUR | 5.00 g (29.91 mmol) of 10-oxa-4-azatricyclo[5.2.1.02,6]decane-3,5-dione (example IV, step 1) were suspended in 150 ml of absolute THF under argon and cooled in an ice bath. 2.27 g (59.82 mmol) of lithium aluminum hydride are added in portions, and the mixture is stirred at 0° C. overnight. The reaction solution is hydr... | 10.6084/m9.figshare.5104873.v1 | null | Unsubstituted dicarboximide | null | C1CC2OC1C1CNCC21 | C1CC2OC1C1CNCC21 | C1CC2OC1C1CNCC21 | Other | C1CCOC1 | 0 | 8 | O=C1NC(=O)C2C3CCC(O3)C12>C1CCOC1>C1CC2OC1C1CNCC21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2b5e20797f2d4f3f95674291e28ba251 | Cc1ccc(S(=O)(=O)Cl)cc1.OCC1CCC(CO)O1>>Cc1ccc(S(=O)(=O)OCC2CCC(COS(=O)(=O)c3ccc(C)cc3)O2)cc1 | C1(=CC=C(C=C1)S(=O)(=O)Cl)C.OCC1OC(CC1)CO>>CC1=CC=C(C=C1)S(=O)(=O)OCC2CCC(O2)COS(=O)(=O)C3=CC=C(C=C3)C | Cl[S:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:29][cH:28]1)(=[O:7])=[O:8].[OH:9][CH2:10][CH:11]1[CH2:12][CH2:13][CH:14]([CH2:15][OH:16])[O:27]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[O:9][CH2:10][CH:11]2[CH2:12][CH2:13][CH:14]([CH2:15][O:16][S:17](=[O:18])(=[O:19])[c:20]3[cH:21][cH:22][c:23]([CH3:24])[cH:25... | Cc1ccc(S(=O)(=O)Cl)cc1.OCC1CCC(CO)O1 | Cc1ccc(S(=O)(=O)OCC2CCC(COS(=O)(=O)c3ccc(C)cc3)O2)cc1 | null | null | ClCCl.N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 75589024cce380ea992be9136d347463fabae9c01d441c790f0bfde6103b2eb4 | 9bad35860f0722eac416364029336fbb608c7c0a16fd35ad17e62b56f7080298 | O=S(=O)(OCC1CCC(COS(=O)(=O)c2ccccc2)O1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[OH;D1;+0:7]-[C:8]-[C:9]-[#8:10]-[C:11]-[C:12]-[OH;D1;+0:13]>>[O;D1;H0:14]=[#16:15](=[O;D1;H0:16])(-[c:17])-[O;H0;D2;+0:7]-[C:8]-[C:9]-[#8:10]-[C:11]-[C:12]-[O;H0;D2;+0:13]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | 24 | HOUR | 34.0 g (261 mmol) of 2,5-bis(hydroxymethyl)tetrahydrofuran are dissolved in 260 ml of dichloromethane. A solution of 99.0 g (521 mmol) of p-toluenesulfonyl chloride in 52 ml of pyridine and 130 ml of dichloromethane is added dropwise thereto. After stirring at room temperature for 24 hours, the precipitate is filtered ... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Primary alcohol.Primary alcohol.Sulfonyl halide | Tosylate.Tosylate | null | c1ccccc1 | c1ccccc1.C1CCOC1.c1ccccc1 | null | ClCCl.N1=CC=CC=C1 | null | 24 | Cc1ccc(S(=O)(=O)Cl)cc1.OCC1CCC(CO)O1>ClCCl.N1=CC=CC=C1>Cc1ccc(S(=O)(=O)OCC2CCC(COS(=O)(=O)c3ccc(C)cc3)O2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f28c838693d64d378a2dbf9cdb185727 | Cc1ccc(S(=O)(=O)OCC2CCC(COS(=O)(=O)c3ccc(C)cc3)O2)cc1.NCc1ccccc1>>c1ccc(CN2CC3CCC(C2)O3)cc1 | CC1=CC=C(C=C1)S(=O)(=O)OCC2CCC(O2)COS(=O)(=O)C3=CC=C(C=C3)C.C(C1=CC=CC=C1)N>>C(C1=CC=CC=C1)N1CC2CCC(C1)O2 | Cc1ccc(S(=O)(=O)O[CH2:7][CH:8]2[CH2:9][CH2:10][CH:11]([CH2:12]OS(=O)(=O)c3ccc(C)cc3)[O:13]2)cc1.[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH2:6])[cH:14][cH:15]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][N:6]2[CH2:7][CH:8]3[CH2:9][CH2:10][CH:11]([CH2:12]2)[O:13]3)[cH:14][cH:15]1 | Cc1ccc(S(=O)(=O)OCC2CCC(COS(=O)(=O)c3ccc(C)cc3)O2)cc1.NCc1ccccc1 | c1ccc(CN2CC3CCC(C2)O3)cc1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 2e8a5c0298a5afc15d589c200326ae8e159578b40fa008fd7ababe22424121ef | 2941ffc596cebe281459b6e26a9c302a8d54541a97758992e7c534d737e4273c | c1ccc(CN2CC3CCC(C2)O3)cc1 | C-c1:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]2-[#8:3]-[C:4](-[CH2;D2;+0:5]-O-S(=O)(=O)-c3:c:c:c(-C):c:c:3)-[C:6]-[C:7]-2):c:c:1.[NH2;D1;+0:8]-[C:9]-[c:10]>>[c:10]-[C:9]-[N;H0;D3;+0:8]1-[CH2;D2;+0:1]-[C:2]2-[#8:3]-[C:4](-[C:6]-[C:7]-2)-[CH2;D2;+0:5]-1 | null | [] | null | null | null | null | 112 g (250 mmol) of 2,5-anhydro-3,4-dideoxy-1,6-bis-O-[(4-methylphenyl)sulfonyl]-hexitol from step 1 and 90.7 g (840 mmol) of benzylamine in 500 ml of toluene are heated under reflux for 20 hours. The precipitate is then filtered off with suction and washed with toluene. The combined toluene phases are concentrated in ... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Tosylate.Primary amine | Tertiary amine | c1ccccc1.c1ccccc1 | C1CC2C[NH]CC1O2 | c1ccccc1.C1CC2C[NH]CC1O2 | TsOH.HO- | C1(=CC=CC=C1)C | null | null | Cc1ccc(S(=O)(=O)OCC2CCC(COS(=O)(=O)c3ccc(C)cc3)O2)cc1.NCc1ccccc1>C1(=CC=CC=C1)C>c1ccc(CN2CC3CCC(C2)O3)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e6c92f751d374d10a3c43575d67b3af8 | C1CC2CNCC1O2.CCOC(=O)C(Br)C(=O)OCC>>CCOC(=O)C(C(=O)OCC)N1CC2CCC(C1)O2 | BrC(C(=O)OCC)C(=O)OCC.C([O-])([O-])=O.[K+].[K+].C12CNCC(CC1)O2>>C12CN(CC(CC1)O2)C(C(=O)OCC)C(=O)OCC | [NH:12]1[CH2:13][CH:14]2[CH2:15][CH2:16][CH:17]([CH2:18]1)[O:19]2.Br[CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:7](=[O:8])[O:9][CH2:10][CH3:11]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([C:7](=[O:8])[O:9][CH2:10][CH3:11])[N:12]1[CH2:13][CH:14]2[CH2:15][CH2:16][CH:17]([CH2:18]1)[O:19]2 | C1CC2CNCC1O2.CCOC(=O)C(Br)C(=O)OCC | CCOC(=O)C(C(=O)OCC)N1CC2CCC(C1)O2 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | e9e2ea1658f2508d5a79536d07d0c339caa17b25bfaff8247fc5e7f7235b648b | 92ab7c81a3b645459368b537cad0bfcabc363bceb49c7616365687164708b039 | C1CC2CNCC1O2 | Br-[CH;D3;+0:1](-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5])-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9].[#8:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[C:9]-[#8:8]-[C:6](=[O;D1;H0:7])-[CH;D3;+0:1](-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5])-[N;H0;D3;+0:13]1-[C:12]-[C:11]-[#8:10]-[C:15]-[C:14]-1 | null | [] | 50 | CELSIUS | 8 | HOUR | 4.72 g (19.8 mmol) of diethyl 2-bromomalonate are introduced into 30 ml of acetonitrile. Then 3.82 g (27.7 mmol) of potassium carbonate and 2.46 g (21.7 mmol) of 8-oxa-3-azabicyclo[3.2.1]octane from step 4 are added. The suspension is stirred at 50° C. overnight. This is followed by filtration with suction and evaporat... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ester.Ester.Secondary amine | Ester.Ester.Tertiary amine | C1CC2CNCC1O2 | C1CC2C[NH]CC1O2 | C1CC2C[NH]CC1O2 | HBr | C(C)#N | 50 | 8 | C1CC2CNCC1O2.CCOC(=O)C(Br)C(=O)OCC>C(C)#N>CCOC(=O)C(C(=O)OCC)N1CC2CCC(C1)O2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c66547f1e8ed497f9aeea1ac5fc81abd | CCOC(=O)C(C(=O)OCC)N1CC2CCC(C1)O2.N=C(N)c1nn(Cc2ccccc2F)c2ncccc12>>Oc1nc(-c2nn(Cc3ccccc3F)c3ncccc23)nc(O)c1N1CC2CCC(C1)O2 | FC1=C(CN2N=C(C=3C2=NC=CC3)C(N)=N)C=CC=C1.C12CN(CC(CC1)O2)C(C(=O)OCC)C(=O)OCC>>FC1=C(CN2N=C(C=3C2=NC=CC3)C3=NC(=C(C(=N3)O)N3CC2CCC(C3)O2)O)C=CC=C1 | CCO[C:2](=[O:1])[CH:25]([C:23](OCC)=[O:24])[N:26]1[CH2:27][CH:28]2[CH2:29][CH2:30][CH:31]([CH2:32]1)[O:33]2.[NH:3]=[C:4]([c:5]1[n:6][n:7]([CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[F:15])[c:16]2[n:17][cH:18][cH:19][cH:20][c:21]12)[NH2:22]>>[OH:1][c:2]1[n:3][c:4](-[c:5]2[n:6][n:7]([CH2:8][c:9]3[cH:10][cH:11][cH:12... | CCOC(=O)C(C(=O)OCC)N1CC2CCC(C1)O2.N=C(N)c1nn(Cc2ccccc2F)c2ncccc12 | Oc1nc(-c2nn(Cc3ccccc3F)c3ncccc23)nc(O)c1N1CC2CCC(C1)O2 | null | null | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | d507ea5e988c6bcfe927f1b3a86f934f8a1c706f38171153cdf4dbd7aeb28e83 | 6504f33921726f64e36c5f3f322459b73652319c83071522ec21b8b88a33a5a7 | c1ccc(Cn2nc(-c3ncc(N4CC5CCC(C4)O5)cn3)c3cccnc32)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[CH;D3;+0:3](-[#7:4](-[C:5])-[C:6])-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-O-C-C.[C:9]-[#7;a:10]1:[#7;a:11]:[c;H0;D3;+0:12](-[C;H0;D3;+0:13](-[NH2;D1;+0:14])=[NH;D1;+0:15]):[c:16](:[c:17]):[c:18]:1:[#7;a:19]:[c:20]>>[C:5]-[#7:4](-[c;H0;D3;+0:3]1:[c;H0;D3;+0:1](-[OH;D1;+0:2]):[n;H0;D2;+0:1... | null | [] | 140 | CELSIUS | 8 | HOUR | 0.50 g (1.11 mmol) of 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboximidamide (example I, step 5) are suspended in 40 ml of toluene. Then 1.40 g (5.16 mmol) of diethyl 2-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)malonate from step 5 are added. The mixture is stirred at 140° C. overnight. The solid is then filtered off... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Primary amine | Aromatic alcohol.Aromatic alcohol | null | c1cncnc1 | c1cncnc1.c1ccccc1.c1[nH]nc2ncccc12.C1CC2C[NH]CC1O2 | HO- | C1(=CC=CC=C1)C | 140 | 8 | CCOC(=O)C(C(=O)OCC)N1CC2CCC(C1)O2.N=C(N)c1nn(Cc2ccccc2F)c2ncccc12>C1(=CC=CC=C1)C>Oc1nc(-c2nn(Cc3ccccc3F)c3ncccc23)nc(O)c1N1CC2CCC(C1)O2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-56e66fdfb1a7426089450f3a51e6ba10 | CO[C@H]1CN(C(=O)OC(C)(C)C)C[C@@H]1OC>>CO[C@H]1CNC[C@@H]1OC | CO[C@H]1CN(C[C@@H]1OC)C(=O)OC(C)(C)C>>CO[C@H]1CNC[C@@H]1OC | CC(C)(C)OC(=O)[N:5]1[CH2:4][C@H:3]([O:2][CH3:1])[C@@H:7]([O:8][CH3:9])[CH2:6]1>>[CH3:1][O:2][C@H:3]1[CH2:4][NH:5][CH2:6][C@@H:7]1[O:8][CH3:9] | CO[C@H]1CN(C(=O)OC(C)(C)C)C[C@@H]1OC | CO[C@H]1CNC[C@@H]1OC | null | null | Cl | Reduction | Boc amine deprotection | 7b506000be0005f6be41b2386b5bd6a8c45f704baa22d692d2f2ec984758e4ad | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | C1CCNC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1>>[C:3]1-[C:2]-[NH;D2;+0:1]-[C:5]-[C:4]-1 | null | [] | null | null | 8 | HOUR | 2.30 g (9.35 mmol; 94% pure) of tert-butyl (3S,4S)-3,4-dimethoxy-1-pyrrolidinecarboxylate (example XVI, step 2) are taken up in 50 ml of hydrochloric acid (4M in dioxane) and stirred at RT overnight. The solvent is removed in vacuo, and the residue is suspended in DCM, mixed with 1N sodium hydroxide solution and stirre... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]C1 | C1CCNC1 | C1CCNC1 | HO- | Cl | null | 8 | CO[C@H]1CN(C(=O)OC(C)(C)C)C[C@@H]1OC>Cl>CO[C@H]1CNC[C@@H]1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e2abdf35125f4a8789256a10ba8b5587 | CCO.O=C(O)c1ccc(F)cc1Br>>CCOC(=O)c1ccc(F)cc1Br | C(C(=O)Cl)(=O)Cl.BrC1=C(C(=O)O)C=CC(=C1)F.C(C)N(CC)CC.C(C)O>>BrC1=C(C(=O)OCC)C=CC(=C1)F | O[CH2:2][CH3:1].[OH:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][c:12]1[Br:13]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][c:12]1[Br:13] | CCO.O=C(O)c1ccc(F)cc1Br | CCOC(=O)c1ccc(F)cc1Br | null | null | O.C(Cl)Cl.C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Esterification of Carboxylic Acids | 3f9a9ace480b666da05fcfe5450d12b5c1ea5b0d435c195e1dd4bd20281604bb | dcbf04ec563ed0e9dfc79070490a028958024079a671c385858bb18cc8ec995a | c1ccccc1 | O-[CH2;D2;+0:1]-[C;D1;H3:2].[O;D1;H0:3]=[C:4](-[OH;D1;+0:5])-[c:6]>>[C;D1;H3:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[C:4](=[O;D1;H0:3])-[c:6] | null | [] | null | null | 4 | HOUR | 281 mg (2.21 mmol) of oxalyl chloride are added to a solution of 220 mg (1.01 mmol) of 2-bromo-4-fluorobenzoic acid in 5 ml of absolute toluene under argon, and the mixture is stirred at RT for 4 hours. The solvent is removed in vacuo, and the residue is taken up three times in DCM and the solvent is removed each time ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1 | HO- | O.C(Cl)Cl.C1(=CC=CC=C1)C | null | 4 | CCO.O=C(O)c1ccc(F)cc1Br>O.C(Cl)Cl.C1(=CC=CC=C1)C>CCOC(=O)c1ccc(F)cc1Br |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b7adf5f83e484202bbbfe8a0c301bb8c | COC(OC)N(C)C.O=C(Cc1cnc(-c2nn(Cc3ccccc3F)c3ncccc23)nc1)C1CC1>>CN(C)/C=C(/C(=O)C1CC1)c1cnc(-c2nn(Cc3ccccc3F)c3ncccc23)nc1 | C1(CC1)C(CC=1C=NC(=NC1)C1=NN(C2=NC=CC=C21)CC2=C(C=CC=C2)F)=O.COC(N(C)C)OC>>C1(CC1)C(\C(=C\N(C)C)\C=1C=NC(=NC1)C1=NN(C2=NC=CC=C21)CC2=C(C=CC=C2)F)=O | CO[CH:4](OC)[N:2]([CH3:1])[CH3:3].[CH2:5]([C:6](=[O:7])[CH:8]1[CH2:9][CH2:10]1)[c:11]1[cH:12][n:13][c:14](-[c:15]2[n:16][n:17]([CH2:18][c:19]3[cH:20][cH:21][cH:22][cH:23][c:24]3[F:25])[c:26]3[n:27][cH:28][cH:29][cH:30][c:31]23)[n:32][cH:33]1>>[CH3:1][N:2]([CH3:3])/[CH:4]=[C:5](/[C:6](=[O:7])[CH:8]1[CH2:9][CH2:10]1)[c:1... | COC(OC)N(C)C.O=C(Cc1cnc(-c2nn(Cc3ccccc3F)c3ncccc23)nc1)C1CC1 | CN(C)/C=C(/C(=O)C1CC1)c1cnc(-c2nn(Cc3ccccc3F)c3ncccc23)nc1 | null | null | CN(C)C=O | C-C Coupling | OtherReaction | 57f48fac7254684faf48980af66a0d538cb8dee0ab05f049059285d4840b8be4 | 49ae3600e90e05c7cda8811d9438748b91211f407b3eab7b1bcb51e798f4d85a | [CH]=C(C(=O)C1CC1)c1cnc(-c2nn(Cc3ccccc3)c3ncccc23)nc1 | C-O-[CH;D3;+0:1](-O-C)-[#7:2](-[C;D1;H3:3])-[C;D1;H3:4].[C:5]-[C:6](=[O;D1;H0:7])-[CH2;D2;+0:8]-[c:9]1:[c:10]:[#7;a:11]:[c:12]:[#7;a:13]:[c:14]:1>>[C:5]-[C:6](=[O;D1;H0:7])/[C;H0;D3;+0:8](=[CH;D2;+0:1]/[#7:2](-[C;D1;H3:3])-[C;D1;H3:4])-[c:9]1:[c:10]:[#7;a:11]:[c:12]:[#7;a:13]:[c:14]:1 | null | [] | 110 | CELSIUS | 2 | HOUR | 100 mg (0.26 mmol) of 1-cyclopropyl-2-{2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]-pyridin-3-yl]-5-pyrimidinyl}ethanone (example XXVI, step 1) are added to a solution of 123 mg (1.03 mmol) of N-(dimethoxymethyl)-N,N-dimethylamine in 1 ml of DMF. The reaction mixture is stirred at 110° C. for 2 hours and then poured into d... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Ether | Enamine | null | null | C1CC1.c1cncnc1.c1ccccc1.c1[nH]nc2ncccc12 | HO- | CN(C)C=O | 110 | 2 | COC(OC)N(C)C.O=C(Cc1cnc(-c2nn(Cc3ccccc3F)c3ncccc23)nc1)C1CC1>CN(C)C=O>CN(C)/C=C(/C(=O)C1CC1)c1cnc(-c2nn(Cc3ccccc3F)c3ncccc23)nc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3b9692a8f94a4325b9f1310600f39178 | CC(C)I.Fc1ccccc1Cn1nc(-c2ncc(N3CC4CC3CN4)cn2)c2cccnc21>>CC(C)N1CC2CC1CN2c1cnc(-c2nn(Cc3ccccc3F)c3ncccc23)nc1 | O.C([O-])([O-])=O.[Na+].[Na+].C12N(CC(NC1)C2)C=2C=NC(=NC2)C2=NN(C1=NC=CC=C12)CC1=C(C=CC=C1)F.IC(C)C>>FC1=C(CN2N=C(C=3C2=NC=CC3)C3=NC=C(C=N3)N3C2CN(C(C3)C2)C(C)C)C=CC=C1 | I[CH:2]([CH3:1])[CH3:3].[NH:4]1[CH2:5][CH:6]2[CH2:7][CH:8]1[CH2:9][N:10]2[c:11]1[cH:12][n:13][c:14](-[c:15]2[n:16][n:17]([CH2:18][c:19]3[cH:20][cH:21][cH:22][cH:23][c:24]3[F:25])[c:26]3[n:27][cH:28][cH:29][cH:30][c:31]23)[n:32][cH:33]1>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH:6]2[CH2:7][CH:8]1[CH2:9][N:10]2[c:11]1[cH:12... | CC(C)I.Fc1ccccc1Cn1nc(-c2ncc(N3CC4CC3CN4)cn2)c2cccnc21 | CC(C)N1CC2CC1CN2c1cnc(-c2nn(Cc3ccccc3F)c3ncccc23)nc1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 95a3aba3961f7ace3382eb51a0774a94b615823c8221e5054b03deda57b3c29e | fb63ba09935e18320be03869002f6d5d0f0321fe7dbcd94a5ae956c3effd182d | c1ccc(Cn2nc(-c3ncc(N4CC5CC4CN5)cn3)c3cccnc32)cc1 | I-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[#7:4]1-[C:5]-[C:6]2-[C:7]-[C:8]-1-[C:9]-[NH;D2;+0:10]-2>>[C;D1;H3:2]-[CH;D3;+0:1](-[C;D1;H3:3])-[N;H0;D3;+0:10]1-[C:9]-[C:8]2-[#7:4]-[C:5]-[C:6]-1-[C:7]-2 | null | [] | null | null | 8 | HOUR | 50 mg (0.13 mmol) of 3-[5-(2,5-diazabicyclo[2.2.1]hept-2-yl)-2-pyrimidinyl]-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine (example 9) are dissolved in 5 ml of absolute acetone, and 92 mg (0.87 mmol) of sodium carbonate are added. 64 mg (0.37 mmol) of 2-iodopropane are added to the suspension, and the mixture is stirred... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary amine | Tertiary amine | C1NC2C[NH]C1C2 | C1[NH]C2C[NH]C1C2 | C1[NH]C2C[NH]C1C2.c1cncnc1.c1ccccc1.c1[nH]nc2ncccc12 | HI | CC(=O)C | null | 8 | CC(C)I.Fc1ccccc1Cn1nc(-c2ncc(N3CC4CC3CN4)cn2)c2cccnc21>CC(=O)C>CC(C)N1CC2CC1CN2c1cnc(-c2nn(Cc3ccccc3F)c3ncccc23)nc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-95a3c85d0be542beac729e463c062d1c | Fc1ccccc1Cn1nc(-c2nc(Cl)c(N3CC4CCC(C3)O4)c(Cl)n2)c2cccnc21>>Fc1ccccc1Cn1nc(-c2ncc(N3CC4CCC(C3)O4)cn2)c2cccnc21 | ClC1=NC(=NC(=C1N1CC2CCC(C1)O2)Cl)C2=NN(C1=NC=CC=C12)CC1=C(C=CC=C1)F.C(=O)[O-].[NH4+]>>FC1=C(CN2N=C(C=3C2=NC=CC3)C3=NC=C(C=N3)N3CC2CCC(C3)O2)C=CC=C1 | Cl[c:14]1[n:13][c:12](-[c:11]2[n:10][n:9]([CH2:8][c:7]3[c:2]([F:1])[cH:3][cH:4][cH:5][cH:6]3)[c:31]3[c:26]2[cH:27][cH:28][cH:29][n:30]3)[n:25][c:24](Cl)[c:15]1[N:16]1[CH2:17][CH:18]2[CH2:19][CH2:20][CH:21]([CH2:22]1)[O:23]2>>[F:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH2:8][n:9]1[n:10][c:11](-[c:12]2[n:13][cH:14][c:15](... | Fc1ccccc1Cn1nc(-c2nc(Cl)c(N3CC4CCC(C3)O4)c(Cl)n2)c2cccnc21 | Fc1ccccc1Cn1nc(-c2ncc(N3CC4CCC(C3)O4)cn2)c2cccnc21 | null | [Pd] | CO | Reduction | OtherReaction | fcc37c9c611ca40bb9c411eab4802374f0106d75bef4c7f56886315f511a7627 | 0ecff68b4ffbd9fa417ba42b220387f06d93399a1e61c4d05eaeeacbdad5d93b | c1ccc(Cn2nc(-c3ncc(N4CC5CCC(C4)O5)cn3)c3cccnc32)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[c:4]:[#7;a:5]:[#7;a:6]):[#7;a:7]:[c;H0;D3;+0:8](-Cl):[c:9]:1-[#7:10]>>[#7:10]-[c:9]1:[cH;D2;+0:1]:[#7;a:2]:[c:3](-[c:4]:[#7;a:5]:[#7;a:6]):[#7;a:7]:[cH;D2;+0:8]:1 | null | [] | null | null | null | null | 400 mg (0.68 mmol) of 3-[4,6-dichloro-5-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-2-pyrimidinyl]-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine (example XII, step 7) are dissolved in 200 ml of methanol, and 86 mg of ammonium formate are added. Under argon, 26 mg of palladium on activated carbon (10%) are added, and the mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide | null | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.C1CC2C[NH]CC1O2.c1n[nH]c2ncccc12 | Other | [Pd].CO | null | null | Fc1ccccc1Cn1nc(-c2nc(Cl)c(N3CC4CCC(C3)O4)c(Cl)n2)c2cccnc21>[Pd].CO>Fc1ccccc1Cn1nc(-c2ncc(N3CC4CCC(C3)O4)cn2)c2cccnc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9f4ad61493c44fe6b1cd7d0ba4f2847c | CI.O[C@@H]1CCN(c2cnc(-c3nn(Cc4ccccc4F)c4ncccc34)nc2)C1>>CO[C@H]1CCN(c2cnc(-c3nn(Cc4ccccc4F)c4ncccc34)nc2)C1 | O.[H-].[Na+].FC1=C(CN2N=C(C=3C2=NC=CC3)C3=NC=C(C=N3)N3C[C@@H](CC3)O)C=CC=C1.IC>>FC1=C(CN2N=C(C=3C2=NC=CC3)C3=NC=C(C=N3)N3C[C@H](CC3)OC)C=CC=C1 | I[CH3:1].[OH:2][C@@H:3]1[CH2:4][CH2:5][N:6]([c:7]2[cH:8][n:9][c:10](-[c:11]3[n:12][n:13]([CH2:14][c:15]4[cH:16][cH:17][cH:18][cH:19][c:20]4[F:21])[c:22]4[n:23][cH:24][cH:25][cH:26][c:27]34)[n:28][cH:29]2)[CH2:30]1>>[CH3:1][O:2][C@H:3]1[CH2:4][CH2:5][N:6]([c:7]2[cH:8][n:9][c:10](-[c:11]3[n:12][n:13]([CH2:14][c:15]4[cH:1... | CI.O[C@@H]1CCN(c2cnc(-c3nn(Cc4ccccc4F)c4ncccc34)nc2)C1 | CO[C@H]1CCN(c2cnc(-c3nn(Cc4ccccc4F)c4ncccc34)nc2)C1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 31ec8f945a35f4f87287620e27b68692ce42732551035fbac056df61d9acce14 | 08f7221cae607d413f579138dcaa6997bebcad2bbb42d2f1b3b2a2d886befb37 | c1ccc(Cn2nc(-c3ncc(N4CCCC4)cn3)c3cccnc32)cc1 | I-[CH3;D1;+0:1].[#7:2]-[C:3]-[C:4](-[OH;D1;+0:5])-[C:6]>>[#7:2]-[C:3]-[C:4](-[O;H0;D2;+0:5]-[CH3;D1;+0:1])-[C:6] | null | [] | null | null | 2 | HOUR | 100 mg (0.21 mmol, purity 80%) of (3S)-1-{2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-pyrimidinyl}-3-pyrrolidinol (example XIX, step 3) are dissolved in 2 ml of DMF under argon and, while cooling in an ice bath 8 mg (0.33 mmol) of sodium hydride are added. 32 mg (0.23 mmol) of iodomethane are added dropwise... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ether | null | null | C1CC[NH]C1.c1cncnc1.c1ccccc1.c1[nH]nc2ncccc12 | HI | CN(C)C=O | null | 2 | CI.O[C@@H]1CCN(c2cnc(-c3nn(Cc4ccccc4F)c4ncccc34)nc2)C1>CN(C)C=O>CO[C@H]1CCN(c2cnc(-c3nn(Cc4ccccc4F)c4ncccc34)nc2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1b2965c8ee8a4c30837640f4245842fe | Fc1ccccc1Cn1nc(-c2ncc(Br)cn2)c2cccnc21.OCc1ccccc1B(O)O>>OCc1ccccc1-c1cnc(-c2nn(Cc3ccccc3F)c3ncccc23)nc1 | C([O-])([O-])=O.[Cs+].[Cs+].BrC=1C=NC(=NC1)C1=NN(C2=NC=CC=C21)CC2=C(C=CC=C2)F.OCC1=C(C=CC=C1)B(O)O>>FC1=C(CN2N=C(C=3C2=NC=CC3)C3=NC=C(C=N3)C3=C(C=CC=C3)CO)C=CC=C1 | Br[c:9]1[cH:10][n:11][c:12](-[c:13]2[n:14][n:15]([CH2:16][c:17]3[cH:18][cH:19][cH:20][cH:21][c:22]3[F:23])[c:24]3[n:25][cH:26][cH:27][cH:28][c:29]23)[n:30][cH:31]1.OB(O)[c:8]1[c:3]([CH2:2][OH:1])[cH:4][cH:5][cH:6][cH:7]1>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1-[c:9]1[cH:10][n:11][c:12](-[c:13]2[n:14][n:15]([... | Fc1ccccc1Cn1nc(-c2ncc(Br)cn2)c2cccnc21.OCc1ccccc1B(O)O | OCc1ccccc1-c1cnc(-c2nn(Cc3ccccc3F)c3ncccc23)nc1 | null | null | COCCOC | C-C Coupling | Suzuki | 5efc69cb0f56c6c241a71b9df28c03b094ed8fc2f31567997f12f88c03083478 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(Cn2nc(-c3ncc(-c4ccccc4)cn3)c3cccnc32)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1.O-B(-O)-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10](-[C:11]):[c:12]>>[C:11]-[c:10](:[c:12]):[c;H0;D3;+0:7](-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1):[c:8]:[c:9] | null | [] | null | null | null | null | 200 mg (0.52 mmol) of 3-(5-bromo-2-pyrimidinyl)-1-(2-fluorobenzyl)-1H-pyrazolo-[3,4-b]pyridine (example I, step 6), 90 mg (0.62 mmol) of 2-(hydroxymethyl)-phenylboronic acid, 40 mg (0.05 mmol) of 1,1′-bis(diphenylphosphino)-ferrocenepalladium(II) chloride and 200 mg (0.62 mmol) of cesium carbonate are taken up in 2 ml ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1.c1[nH]nc2ncccc12 | HBr.B | COCCOC | null | null | Fc1ccccc1Cn1nc(-c2ncc(Br)cn2)c2cccnc21.OCc1ccccc1B(O)O>COCCOC>OCc1ccccc1-c1cnc(-c2nn(Cc3ccccc3F)c3ncccc23)nc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7c6f09ea434c4011b97048e317709430 | O=[N+]([O-])c1ccc(F)c(F)c1>>O=[N+]([O-])Nc1ccccc1 | FC=1C=C(C=CC1F)[N+](=O)[O-].CNC.CCN(C(C)C)C(C)C.C(C)(=O)OCC>>[N+](=O)([O-])NC1=CC=CC=C1 | F[c:5]1[cH:6][cH:7][c:8]([N+:2](=[O:1])[O-:3])[cH:9][c:10]1F>>[O:1]=[N+:2]([O-:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1 | O=[N+]([O-])c1ccc(F)c(F)c1 | O=[N+]([O-])Nc1ccccc1 | null | null | Cl | Miscellaneous | OtherReaction | 85413616a84a2fddd0eb13518d6b10edd90e0c52f269ee1fd9f6527b98518a7e | 3f465b1468aa13034499106561e1703a7809e9dbbdc0d0537c7786a0231b78d4 | c1ccccc1 | F-[c;H0;D3;+0:1]1:[c:2]:[c;H0;D3;+0:3](-[N+;H0;D3:4](-[O;-;D1;H0:5])=[O;D1;H0:6]):[c:7]:[c:8]:[c;H0;D3;+0:9]:1-F>>[O;-;D1;H0:5]-[N+;H0;D3:4](=[O;D1;H0:6])-[#7:10]-[c;H0;D3;+0:9]1:[c:8]:[c:7]:[cH;D2;+0:3]:[c:2]:[cH;D2;+0:1]:1 | null | [] | null | null | 8 | HOUR | 3,4-Difluoronitrobenzene (3 mL, 27.1 mmol) was added to a solution of dimethyl amine (15 mL, 29.8 mmol) and i-Pr2NEt (5.2 ml, 29.8 mmol) in ethyl acetate (20 mL) at 0° C. and the mixture was stirred at room temperature overnight. The yellow solution was concentrated and redissolved in methylene chloride (100 mL) and th... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Nitro group | Hydrazine | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | Cl | null | 8 | O=[N+]([O-])c1ccc(F)c(F)c1>Cl>O=[N+]([O-])Nc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-054b7a2c02c6492294fcf260040320fc | CCOC(=O)C(C(=O)OCC)c1ccc(C)cc1.N=CN>>Cc1ccc(-c2c(O)ncnc2O)cc1 | C[O-].[Na+].C(C)OC(C(C(=O)OCC)C1=CC=C(C=C1)C)=O.Cl.C(=N)N>>C1(=CC=C(C=C1)C=1C(=NC=NC1O)O)C | CCO[C:7]([CH:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:15][cH:14]1)[C:12](OCC)=[O:13])=[O:8].[NH:9]=[CH:10][NH2:11]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c:7]([OH:8])[n:9][cH:10][n:11][c:12]2[OH:13])[cH:14][cH:15]1 | CCOC(=O)C(C(=O)OCC)c1ccc(C)cc1.N=CN | Cc1ccc(-c2c(O)ncnc2O)cc1 | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | d507ea5e988c6bcfe927f1b3a86f934f8a1c706f38171153cdf4dbd7aeb28e83 | 6504f33921726f64e36c5f3f322459b73652319c83071522ec21b8b88a33a5a7 | c1ccc(-c2cncnc2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[CH;D3;+0:3](-[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-O-C-C)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10].[NH2;D1;+0:11]-[CH;D2;+0:12]=[NH;D1;+0:13]>>[OH;D1;+0:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:11]:[cH;D2;+0:12]:[n;H0;D2;+0:13]:[c;H0;D3;+0:4](-[OH;D1;+0:5]):[c;H0;D3;+0:3]:1-[c;H0;D3;+0:6](:[c:7]... | null | [] | null | null | 1 | HOUR | Sodium methylate (17 g) was dissolved in methanol (600 ml) at 0° C. 2-p-tolyl-malonic acid diethyl ester (24.5 ml, commercially available from Aldrich), dissolved in 150 ml methanol, was added within 30 min. Stirring was continued for 1 h while slowly warming the mixture to rt. Formamidine hydrochloride (9.9 g, commerc... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Primary amine | Aromatic alcohol.Aromatic alcohol | null | c1cncnc1 | c1ccccc1.c1cncnc1 | HO- | CO | null | 1 | CCOC(=O)C(C(=O)OCC)c1ccc(C)cc1.N=CN>CO>Cc1ccc(-c2c(O)ncnc2O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-aefda4e42cde42d1b7ffd52f52e1272a | N.O=S(=O)(Cl)CCc1ccccc1>>NS(=O)(=O)CCc1ccccc1 | C1(=CC=CC=C1)CCS(=O)(=O)Cl.N.Cl>>C1(=CC=CC=C1)CCS(=O)(=O)N | [NH3:1].Cl[S:2](=[O:3])(=[O:4])[CH2:5][CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[NH2:1][S:2](=[O:3])(=[O:4])[CH2:5][CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1 | N.O=S(=O)(Cl)CCc1ccccc1 | NS(=O)(=O)CCc1ccccc1 | null | null | C1CCOC1 | Miscellaneous | OtherReaction | 419151dfc49d0719bc8d3fc5b23cdd08248d27df18761ee59c11624194c4c5ab | ae33b93faeb632e8ec1263862cc7a6f628747ed893339f281ddf88c6e380b60a | c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4]-[C:5].[NH3;D0;+0:6]>>[C:5]-[C:4]-[S;H0;D4;+0:1](-[NH2;D1;+0:6])(=[O;D1;H0:2])=[O;D1;H0:3] | null | [] | null | null | 16 | HOUR | A solution of 2-phenylethanesulfonyl chloride (40.94 g) in THF (250 ml) was cooled to −20° C. before it was treated with sat. aq. ammonia (50 ml). The brown suspension was stirred at rt for 16 h. The mixture was neutralised with aq. HCl and the organic solvent was evaporated. The remaining suspension was diluted with w... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | Sulfonamide | null | null | c1ccccc1 | HCl | C1CCOC1 | null | 16 | N.O=S(=O)(Cl)CCc1ccccc1>C1CCOC1>NS(=O)(=O)CCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-de2c64610930487e978e7f18ba39fabb | Cc1ccc(-c2c(Cl)ncnc2Cl)cc1.NS(=O)(=O)CCc1ccccc1>>Cc1ccc(-c2c(Cl)ncnc2NS(=O)(=O)CCc2ccccc2)cc1 | [K].C1(=CC=CC=C1)CCS(=O)(=O)N.ClC1=NC=NC(=C1C1=CC=C(C=C1)C)Cl.CCN(C(C)C)C(C)C>>ClC1=C(C(=NC=N1)NS(=O)(=O)CCC1=CC=CC=C1)C1=CC=C(C=C1)C | Cl[c:12]1[c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:26][cH:25]2)[c:7]([Cl:8])[n:9][cH:10][n:11]1.[NH2:13][S:14](=[O:15])(=[O:16])[CH2:17][CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c:7]([Cl:8])[n:9][cH:10][n:11][c:12]2[NH:13][S:14](=[O:15])(=[O:16])[CH2:17][CH2:18][c:19]2... | Cc1ccc(-c2c(Cl)ncnc2Cl)cc1.NS(=O)(=O)CCc1ccccc1 | Cc1ccc(-c2c(Cl)ncnc2NS(=O)(=O)CCc2ccccc2)cc1 | null | null | CS(=O)C.O | Heteroatom Alkylation and Arylation | OtherReaction | 345edf40ad678aea0250ec5b3d6cc512d8eac020b2f4324f423c18b59726753e | e7974806b40218fa965bb62bf9c430cac38870897b20726116f8b48ae128dc55 | O=S(=O)(CCc1ccccc1)Nc1ncncc1-c1ccccc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[Cl;D1;H0:6]):[c:7]:1-[c:8].[C:9]-[#16:10](-[NH2;D1;+0:11])(=[O;D1;H0:12])=[O;D1;H0:13]>>[C:9]-[#16:10](=[O;D1;H0:12])(=[O;D1;H0:13])-[NH;D2;+0:11]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[Cl;D1;H0:6]):[c:7]:1-[c:8] | 59.6 | [{"value": 59.6, "product": "ClC1=C(C(=NC=N1)NS(=O)(=O)CCC1=CC=CC=C1)C1=CC=C(C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 5 | CELSIUS | null | null | A solution of 2-phenyl-ethanesulfonic acid amide potassium salt (3.0 g), 4,6-dichloro-5-p-tolyl-pyrimidine (2.15 g) and Hunig's base (1.57 ml) in DMSO (50 ml) was stirred at rt for 20 h before it was diluted with water (500 ml) and extracted twice with diethyl ether (250 ml). The aqueous phase was acidified with acetic... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Aromatic halide | Sulfonamide | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HCl | CS(=O)C.O | 5 | null | Cc1ccc(-c2c(Cl)ncnc2Cl)cc1.NS(=O)(=O)CCc1ccccc1>CS(=O)C.O>Cc1ccc(-c2c(Cl)ncnc2NS(=O)(=O)CCc2ccccc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dea881c46bfd42ccbdd4a59a1edaad4c | Cc1ccc(-c2c(Cl)ncnc2NS(=O)(=O)CCc2ccccc2)cc1.O=C(O)CC(O)(CC(=O)O)C(=O)O>>Cc1ccc(-c2c(NS(=O)(=O)CCc3ccccc3)ncnc2OCCO)cc1 | ClC1=C(C(=NC=N1)NS(=O)(=O)CCC1=CC=CC=C1)C1=CC=C(C=C1)C.C(CC(O)(C(=O)O)CC(=O)O)(=O)O>>OCCOC1=C(C(=NC=N1)NS(=O)(=O)CCC1=CC=CC=C1)C1=CC=C(C=C1)C | Cl[c:23]1[c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:29][cH:28]2)[c:7]([NH:8][S:9](=[O:10])(=[O:11])[CH2:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[n:20][cH:21][n:22]1.O=C(O)CC(C(=O)O)([OH:24])[CH2:25][C:26](=O)[OH:27]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c:7]([NH:8][S:9](=[O:10])(=[O:11])[CH2:12][CH2:13... | Cc1ccc(-c2c(Cl)ncnc2NS(=O)(=O)CCc2ccccc2)cc1.O=C(O)CC(O)(CC(=O)O)C(=O)O | Cc1ccc(-c2c(NS(=O)(=O)CCc3ccccc3)ncnc2OCCO)cc1 | null | null | C(CO)O.O | Heteroatom Alkylation and Arylation | OtherReaction | b18ba87fb2ec0987a978e901bb5a53033e53fbf47b9296eda6a432ff7972ccf1 | 0d57d11c1ca6b9fbb36ccec54ea803b423eb00045b608c0a6b2fdbd90fbd86af | O=S(=O)(CCc1ccccc1)Nc1ncncc1-c1ccccc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]):[c:7]:1-[c:8].O-C(=O)-C-C(-[OH;D1;+0:9])(-[CH2;D2;+0:10]-[C;H0;D3;+0:11](=O)-[O;D1;H1:12])-C(-O)=O>>[#7:6]-[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:9]-[CH2;D2;+0:10]-[CH2;D2;+0:11]-[O;D1;H1:12]):[c:7]:1-[c:8] | null | [] | 120 | CELSIUS | 27 | HOUR | 2-Phenyl-ethanesulfonic acid (6-chloro-5-p-tolyl-pyrimidin-4-yl)-amide (850 mg) was added to a solution of K-tert. butylate (1.1 g) in ethylene glycol (15 ml). The mixture was stirred at 120° C. for 27 h before it was diluted with water (100 ml), acidified with 10% aq. citric acid (13 ml). The resulting precipitate was... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carboxylic acid.Carboxylic acid.Carboxylic acid.Tertiary alcohol | Ether.Primary alcohol | c1cncnc1 | c1cncnc1 | c1ccccc1.c1ccccc1.c1cncnc1 | HCl | C(CO)O.O | 120 | 27 | Cc1ccc(-c2c(Cl)ncnc2NS(=O)(=O)CCc2ccccc2)cc1.O=C(O)CC(O)(CC(=O)O)C(=O)O>C(CO)O.O>Cc1ccc(-c2c(NS(=O)(=O)CCc3ccccc3)ncnc2OCCO)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f98f5a335bf343b985a425cce2db865f | N#Cc1ccncc1.[Cl-].[NH4+]>>Cl.N=C(N)c1ccncc1 | C(C)OCC.[Cl-].[NH4+].[Na].C(#N)C1=CC=NC=C1>>Cl.C(N)(=N)C1=CC=NC=C1 | [N:2]#[C:3][c:5]1[cH:6][cH:7][n:8][cH:9][cH:10]1.[Cl-:1].[NH4+:4]>>[ClH:1].[NH:2]=[C:3]([NH2:4])[c:5]1[cH:6][cH:7][n:8][cH:9][cH:10]1 | N#Cc1ccncc1.[Cl-].[NH4+] | Cl.N=C(N)c1ccncc1 | null | null | CO | Functional Group Interconversion | OtherReaction | 3b047a13c16a607c445b1c419e256808e8c9a0097d8fb9efd4e7970deb782b70 | 2882e57127fc469aa16ca9a2fd53388b6d97c74c76c010e6eb01be5726f46aa5 | c1ccncc1 | [Cl-;H0;D0:1].[N;H0;D1;+0:2]#[C;H0;D2;+0:3]-[c:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1.[NH4+;D0:10]>>[ClH;D0;+0:1].[NH2;D1;+0:10]-[C;H0;D3;+0:3](=[NH;D1;+0:2])-[c:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1 | 93 | [{"value": 93.0, "product": "Cl.C(N)(=N)C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | To a solution of sodium (0.23 g) in methanol (40 ml) was added 4-cyanopyridine (10.62 g) at room temperature. Stirring was continued for 6 h followed by the addition of ammoniumchloride (5.9 g) and stirring was continued for another 10 h. Then diethylether (120 ml) was added and the precipitate was filtered off after 3... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccncc1 | null | CO | null | 6 | N#Cc1ccncc1.[Cl-].[NH4+]>CO>Cl.N=C(N)c1ccncc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b939b42b0d324149bc288dcb9f098465 | Cc1ccc(-c2c(Cl)nc(-c3ccncc3)nc2Cl)cc1.NS(=O)(=O)CCc1ccccc1>>Cc1ccc(-c2c(Cl)nc(-c3ccncc3)nc2NS(=O)(=O)CCc2ccccc2)cc1 | ClC1=NC(=NC(=C1C1=CC=C(C=C1)C)Cl)C1=CC=NC=C1.[K].C1(=CC=CC=C1)CCS(=O)(=O)N.CCN(C(C)C)C(C)C>>ClC1=C(C(=NC(=N1)C1=CC=NC=C1)NS(=O)(=O)CCC1=CC=CC=C1)C1=CC=C(C=C1)C | Cl[c:18]1[c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:32][cH:31]2)[c:7]([Cl:8])[n:9][c:10](-[c:11]2[cH:12][cH:13][n:14][cH:15][cH:16]2)[n:17]1.[NH2:19][S:20](=[O:21])(=[O:22])[CH2:23][CH2:24][c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c:7]([Cl:8])[n:9][c:10](-[c:11]3[cH:12][cH:13][... | Cc1ccc(-c2c(Cl)nc(-c3ccncc3)nc2Cl)cc1.NS(=O)(=O)CCc1ccccc1 | Cc1ccc(-c2c(Cl)nc(-c3ccncc3)nc2NS(=O)(=O)CCc2ccccc2)cc1 | null | null | CS(=O)C.O | Heteroatom Alkylation and Arylation | OtherReaction | 345edf40ad678aea0250ec5b3d6cc512d8eac020b2f4324f423c18b59726753e | e7974806b40218fa965bb62bf9c430cac38870897b20726116f8b48ae128dc55 | O=S(=O)(CCc1ccccc1)Nc1nc(-c2ccncc2)ncc1-c1ccccc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](-[Cl;D1;H0:7]):[c:8]:1-[c:9].[C:10]-[#16:11](-[NH2;D1;+0:12])(=[O;D1;H0:13])=[O;D1;H0:14]>>[C:10]-[#16:11](=[O;D1;H0:13])(=[O;D1;H0:14])-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](-[Cl;D1;H0:7]):[c:8]:1-[c:9] | 21.8 | [{"value": 21.8, "product": "ClC1=C(C(=NC(=N1)C1=CC=NC=C1)NS(=O)(=O)CCC1=CC=CC=C1)C1=CC=C(C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4,6-dichloro-2-(4-pyridyl)-5-(p-tolyl)-pyrimidine (1.5 g), 2-phenyl-ethanesulfonic acid amide potassium salt (1.44 g, Referential Example 1e) and Hunig's base (1 ml) in DMSO (20 ml) was stirred at rt for 24 h before it was diluted with water (150 ml) and extracted twice with diethyl ether. The aqueous lay... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Aromatic halide | Sulfonamide | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccncc1.c1ccccc1 | HCl | CS(=O)C.O | null | null | Cc1ccc(-c2c(Cl)nc(-c3ccncc3)nc2Cl)cc1.NS(=O)(=O)CCc1ccccc1>CS(=O)C.O>Cc1ccc(-c2c(Cl)nc(-c3ccncc3)nc2NS(=O)(=O)CCc2ccccc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2f674e412cd94d6e9616d8a0d73b8925 | Cc1ccc(-c2c(Cl)nc(-c3ccncc3)nc2NS(=O)(=O)CCc2ccccc2)cc1.O=C(O)CC(O)(CC(=O)O)C(=O)O>>Cc1ccc(-c2c(NS(=O)(=O)CCc3ccccc3)nc(-c3ccncc3)nc2OCCO)cc1 | ClC1=C(C(=NC(=N1)C1=CC=NC=C1)NS(=O)(=O)CCC1=CC=CC=C1)C1=CC=C(C=C1)C.C(CC(O)(C(=O)O)CC(=O)O)(=O)O>>OCCOC1=C(C(=NC(=N1)C1=CC=NC=C1)NS(=O)(=O)CCC1=CC=CC=C1)C1=CC=C(C=C1)C | Cl[c:29]1[c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:35][cH:34]2)[c:7]([NH:8][S:9](=[O:10])(=[O:11])[CH2:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[n:20][c:21](-[c:22]2[cH:23][cH:24][n:25][cH:26][cH:27]2)[n:28]1.O=C(O)CC(C(=O)O)([OH:30])[CH2:31][C:32](=O)[OH:33]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c:7](... | Cc1ccc(-c2c(Cl)nc(-c3ccncc3)nc2NS(=O)(=O)CCc2ccccc2)cc1.O=C(O)CC(O)(CC(=O)O)C(=O)O | Cc1ccc(-c2c(NS(=O)(=O)CCc3ccccc3)nc(-c3ccncc3)nc2OCCO)cc1 | null | null | C(CO)O.O | Heteroatom Alkylation and Arylation | OtherReaction | b18ba87fb2ec0987a978e901bb5a53033e53fbf47b9296eda6a432ff7972ccf1 | 0d57d11c1ca6b9fbb36ccec54ea803b423eb00045b608c0a6b2fdbd90fbd86af | O=S(=O)(CCc1ccccc1)Nc1nc(-c2ccncc2)ncc1-c1ccccc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](-[#7:7]):[c:8]:1-[c:9].O-C(=O)-C-C(-[OH;D1;+0:10])(-[CH2;D2;+0:11]-[C;H0;D3;+0:12](=O)-[O;D1;H1:13])-C(-O)=O>>[#7:7]-[c:6]1:[#7;a:5]:[c:3](-[c:4]):[#7;a:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:10]-[CH2;D2;+0:11]-[CH2;D2;+0:12]-[O;D1;H1:13]):[c:8]:1-[c:9] | null | [] | 11 | CELSIUS | 72 | HOUR | 2-Phenyl-ethanesulfonic acid (6-chloro-2-pyridin-4-yl-5-p-tolyl-pyrimidin-4-yl)-amide (480 mg) was added to a solution of K-tert. butylate (580 mg) in ethylene glycol (5 ml). The mixture was stirred at 11° C. for 72 h before it was diluted with water (100 ml), acidified with 10% aq. citric acid (13 ml). The resulting p... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carboxylic acid.Carboxylic acid.Carboxylic acid.Tertiary alcohol | Ether.Primary alcohol | c1cncnc1 | c1cncnc1 | c1ccccc1.c1ccccc1.c1cncnc1.c1ccncc1 | HCl | C(CO)O.O | 11 | 72 | Cc1ccc(-c2c(Cl)nc(-c3ccncc3)nc2NS(=O)(=O)CCc2ccccc2)cc1.O=C(O)CC(O)(CC(=O)O)C(=O)O>C(CO)O.O>Cc1ccc(-c2c(NS(=O)(=O)CCc3ccccc3)nc(-c3ccncc3)nc2OCCO)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a49db3e4ff1840bf80f49c0406a40f8c | CCOC(C)=O.Cc1ccc(Br)cc1C.O=P([O-])([O-])[O-]>>COC(=O)C(C(=O)OC)c1ccc(C)c(C)c1 | [O-]P(=O)([O-])[O-].[K+].[K+].[K+].BrC1=CC(=C(C=C1)C)C.CC(OCC)=O>>COC(C(C(=O)OC)C1=CC(=C(C=C1)C)C)=O | [CH2:1]([O:2][C:3](=[O:4])[CH3:5])[CH3:6].Br[c:10]1[cH:11][cH:12][c:13]([CH3:14])[c:15]([CH3:16])[cH:17]1.[O-]P([O-])(=[O:7])[O-:8]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([C:6](=[O:7])[O:8][CH3:9])[c:10]1[cH:11][cH:12][c:13]([CH3:14])[c:15]([CH3:16])[cH:17]1 | CCOC(C)=O.Cc1ccc(Br)cc1C.O=P([O-])([O-])[O-] | COC(=O)C(C(=O)OC)c1ccc(C)c(C)c1 | null | CC(=O)[O-].CC(=O)[O-].[Pd+2].C(C)(C)(C)P(C1=C(C=CC=C1)C1=CC=CC=C1)C(C)(C)C | C1CCOC1 | Acylation | OtherReaction | ac625cc5be219ad0882aee2a58a398097d18e0d3b80eb4bab2acee5e648b3151 | dff5b5ca87e4b238f4d0d4aa4fe50bb5b3c87259a2931b4da63c193c1c251085 | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[CH3;D1;+0:6]-[C:7](=[O;D1;H0:8])-[#8:9]-[CH2;D2;+0:10]-[CH3;D1;+0:11].[O-;H0;D1:12]-P(-[O-])(-[O-])=[O;H0;D1;+0:13]>>[C;D1;H3:14]-[O;H0;D2;+0:12]-[C;H0;D3;+0:11](=[O;H0;D1;+0:13])-[CH;D3;+0:6](-[C:7](=[O;D1;H0:8])-[#8:9]-[CH3;D1;+0:10])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:... | null | [] | null | null | null | null | (In analogy to a procedure given in J. Am. Chem. Soc. 122 (2000), 1360-1370.) To a suspension of Pd(OAc)2 (455 mg), 2-(di-tert.-butylphosphino)-biphenyl (1.21 g) and K3PO4 (39.6 g) in THF (200 ml) dimethylmalonate (12.85 g) and 1-bromo-3,4-dimethyl-benzene 15.0 g) was added under argon. The mixture was refluxed for 16 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester | Ester.Ester | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | CC(=O)[O-].CC(=O)[O-].[Pd+2].C(C)(C)(C)P(C1=C(C=CC=C1)C1=CC=CC=C1)C(C)(C)C.C1CCOC1 | null | null | CCOC(C)=O.Cc1ccc(Br)cc1C.O=P([O-])([O-])[O-]>CC(=O)[O-].CC(=O)[O-].[Pd+2].C(C)(C)(C)P(C1=C(C=CC=C1)C1=CC=CC=C1)C(C)(C)C.C1CCOC1>COC(=O)C(C(=O)OC)c1ccc(C)c(C)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-82f8576a87f140efbfe729c5f4cccf25 | CCOC(C)=O.Cc1ccc(Br)c(C)c1.O=P([O-])([O-])[O-]>>COC(=O)C(C(=O)OC)c1ccc(C)cc1C | CC(OCC)=O.[O-]P(=O)([O-])[O-].[K+].[K+].[K+].BrC1=C(C=C(C=C1)C)C>>COC(C(C(=O)OC)C1=C(C=C(C=C1)C)C)=O | [CH3:1][CH2:9][O:8][C:6]([CH3:5])=[O:7].Br[c:10]1[cH:11][cH:12][c:13]([CH3:14])[cH:15][c:16]1[CH3:17].[O-]P([O-])([O-:2])=[O:4]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([C:6](=[O:7])[O:8][CH3:9])[c:10]1[cH:11][cH:12][c:13]([CH3:14])[cH:15][c:16]1[CH3:17] | CCOC(C)=O.Cc1ccc(Br)c(C)c1.O=P([O-])([O-])[O-] | COC(=O)C(C(=O)OC)c1ccc(C)cc1C | null | CC(=O)[O-].CC(=O)[O-].[Pd+2] | C1CCOC1 | Acylation | OtherReaction | ac625cc5be219ad0882aee2a58a398097d18e0d3b80eb4bab2acee5e648b3151 | dff5b5ca87e4b238f4d0d4aa4fe50bb5b3c87259a2931b4da63c193c1c251085 | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C;D1;H3:5]):[c:6].[CH3;D1;+0:7]-[CH2;D2;+0:8]-[#8:9]-[C:10](-[CH3;D1;+0:11])=[O;D1;H0:12].[O-;H0;D1:13]-P(-[O-])(-[O-])=[O;H0;D1;+0:14]>>[C;D1;H3:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[CH;D3;+0:11](-[C:15](=[O;H0;D1;+0:14])-[O;H0;D2;+0:13]-[CH3;D1;+0:7])-[C:10](=[O;D1;H0:12])-[#8:9]-[... | null | [] | null | null | null | null | (In analogy to a procedure given in J. Am. Chem. Soc. 122 (2000), 1360–1370.) To a suspension of Pd(OAc)2 (758 mg), 2-(di-tert.-butlylphosphino)-biphenyl (2.02 g) and K3PO4 (65.95 g) in THF (350 ml) dimethylmalonate (21.42 g) and 1-bromo-2,4-dimethyl-benzene (25 g) was added under argon. The mixture was refluxed for 96... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester | Ester.Ester | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | CC(=O)[O-].CC(=O)[O-].[Pd+2].C1CCOC1 | null | null | CCOC(C)=O.Cc1ccc(Br)c(C)c1.O=P([O-])([O-])[O-]>CC(=O)[O-].CC(=O)[O-].[Pd+2].C1CCOC1>COC(=O)C(C(=O)OC)c1ccc(C)cc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-442b1ca72e0741b6b6941fed4e97a70d | COC(=O)C(Cl)C(=O)OC.COc1ccccc1O>>COC(=O)C(Oc1ccccc1OC)C(=O)OC | COC(C(C(=O)OC)Cl)=O.COC1=C(C=CC=C1)O.C([O-])([O-])=O.[K+].[K+]>>COC(C(C(=O)OC)OC1=C(C=CC=C1)OC)=O | Cl[CH:5]([C:3]([O:2][CH3:1])=[O:4])[C:15](=[O:16])[O:17][CH3:18].[OH:6][c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[O:13][CH3:14]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([O:6][c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[O:13][CH3:14])[C:15](=[O:16])[O:17][CH3:18] | COC(=O)C(Cl)C(=O)OC.COc1ccccc1O | COC(=O)C(Oc1ccccc1OC)C(=O)OC | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 1abe5687f21dfe01b11318540a21f9edb38806e03f96e75bf8c2106db3fe9462 | 51ddfc8e04785767c04eb49244add5bfc6d44a3e44b55034aace28217a5407e3 | c1ccccc1 | Cl-[CH;D3;+0:1](-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5])-[C:6](=[O;D1;H0:7])-[#8:8]-[C;D1;H3:9].[OH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C;D1;H3:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH;D3;+0:1](-[O;H0;D2;+0:10]-[c:11](:[c:12]):[c:13])-[C:6](=[O;D1;H0:7])-[#8:8]-[C;D1;H3:9] | null | [] | 45 | CELSIUS | null | null | 2-methoxy-phenol (guaiacol) (48 ml) was slowly added to a stirred suspension of potassium carbonate (70.8 g) in acetone (480 ml) followed by heating to 45° C. Then dimethylchloromalonate (63.2 ml) in acetone (50 ml) was added within 20 min. The reaction mixture was heated to reflux for 16 h. The solvent was evaporated ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ester.Ester.Aromatic alcohol | Ester.Ester.Ether | null | null | c1ccccc1 | HCl | CC(=O)C | 45 | null | COC(=O)C(Cl)C(=O)OC.COc1ccccc1O>CC(=O)C>COC(=O)C(Oc1ccccc1OC)C(=O)OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-505c53311be54335b86ddee8a50835c0 | COC(=O)C(Oc1ccccc1OC)C(=O)OC.C[O-].N=C(N)c1ccncc1>>COc1ccccc1OC1C(=O)NC(c2ccncc2)NC1=O.COc1ccccc1Oc1c(O)nc(-c2ccncc2)nc1O | Cl.C(N)(=N)C1=CC=NC=C1.C[O-].[Na+].COC(C(C(=O)OC)OC1=C(C=CC=C1)OC)=O>>COC1=C(OC=2C(=NC(=NC2O)C2=CC=NC=C2)O)C=CC=C1.COC1=C(OC2C(NC(NC2=O)C2=CC=NC=C2)=O)C=CC=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[O:9][CH:10]([C:11](=[O:12])[O:25][CH3:26])[C:37](=[O:23])[O:35][CH3:22].[O-:32][CH3:42].[NH2:13][C:14]([c:15]1[cH:16][cH:17][n:18][cH:19][cH:20]1)=[NH:41]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[O:9][CH:10]1[C:11](=[O:12])[NH:13][CH:14]([c:15]2[cH:16][cH:17][n:... | COC(=O)C(Oc1ccccc1OC)C(=O)OC.C[O-].N=C(N)c1ccncc1 | COc1ccccc1OC1C(=O)NC(c2ccncc2)NC1=O.COc1ccccc1Oc1c(O)nc(-c2ccncc2)nc1O | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | 9a9c0fd8914a5b3de7aba449e4ac4cbba3f03126794a16d273cbee744dcc1f15 | 925a303272c4ce46a1ce7a4b7eda08f07751d881b6ec912720ab6b3c7ea2b3b6 | O=C1NC(c2ccncc2)NC(=O)C1Oc1ccccc1.c1ccc(Oc2cnc(-c3ccncc3)nc2)cc1 | [CH3;D1;+0:1]-[O-;H0;D1:2].[CH3;D1;+0:3]-[O;H0;D2;+0:4]-[C;H0;D3;+0:5](=[O;H0;D1;+0:6])-[CH;D3;+0:7](-[#8:8]-[c:9])-[C;H0;D3;+0:10](=[O;D1;H0:11])-[O;H0;D2;+0:12]-[CH3;D1;+0:13].[NH2;D1;+0:14]-[C;H0;D3;+0:15](=[NH;D1;+0:16])-[c:17]1:[c:18]:[c:19]:[#7;a:20]:[c:21]:[c:22]:1>>[C;D1;H3:23]-[O;H0;D2;+0:12]-[c;H0;D3;+0:13](:... | null | [] | null | null | 30 | MINUTE | To a stirred solution of sodium methylate (9.7 g) in methanol (100 ml) a solution of dimethyl-(2-methoxyphenoxy)malonate (21.7 g) in methanol (50 ml) was added within 15 min and stirring was continued for 30 min followed by the addition of 4-amidino-pyridine hydrochloride (15 g, Referential Example 2) followed by stirr... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ether.Primary amine | Ether.Ether.Ether.Secondary amide.Secondary amide.Aromatic alcohol.Aromatic alcohol | null | C1CNCNC1.c1ccccc1.c1cncnc1.c1ccncc1 | c1ccccc1.C1CNCNC1.c1ccncc1.c1ccccc1.c1cncnc1.c1ccncc1 | null | CO | null | 0.5 | COC(=O)C(Oc1ccccc1OC)C(=O)OC.C[O-].N=C(N)c1ccncc1>CO>COc1ccccc1OC1C(=O)NC(c2ccncc2)NC1=O.COc1ccccc1Oc1c(O)nc(-c2ccncc2)nc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-50ab374672784712afdda58eb7ef9ef4 | COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1Cl.NS(=O)(=O)CCc1ccccc1>>COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1NS(=O)(=O)CCc1ccccc1 | ClC1=NC(=NC(=C1OC1=C(C=CC=C1)OC)Cl)C1=CC=NC=C1.[K].C1(=CC=CC=C1)CCS(=O)(=O)N>>ClC1=C(C(=NC(=N1)C1=CC=NC=C1)NS(=O)(=O)CCC1=CC=CC=C1)OC1=C(C=CC=C1)OC | Cl[c:22]1[c:10]([O:9][c:8]2[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]2)[c:11]([Cl:12])[n:13][c:14](-[c:15]2[cH:16][cH:17][n:18][cH:19][cH:20]2)[n:21]1.[NH2:23][S:24](=[O:25])(=[O:26])[CH2:27][CH2:28][c:29]1[cH:30][cH:31][cH:32][cH:33][cH:34]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[O:9][c:10]1[c:11]([Cl:12])... | COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1Cl.NS(=O)(=O)CCc1ccccc1 | COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1NS(=O)(=O)CCc1ccccc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 345edf40ad678aea0250ec5b3d6cc512d8eac020b2f4324f423c18b59726753e | e7974806b40218fa965bb62bf9c430cac38870897b20726116f8b48ae128dc55 | O=S(=O)(CCc1ccccc1)Nc1nc(-c2ccncc2)ncc1Oc1ccccc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](-[Cl;D1;H0:7]):[c:8]:1-[#8:9].[C:10]-[#16:11](-[NH2;D1;+0:12])(=[O;D1;H0:13])=[O;D1;H0:14]>>[#8:9]-[c:8]1:[c:6](-[Cl;D1;H0:7]):[#7;a:5]:[c:3](-[c:4]):[#7;a:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:12]-[#16:11](-[C:10])(=[O;D1;H0:13])=[O;D1;H0:14] | 78.1 | [{"value": 78.1, "product": "ClC1=C(C(=NC(=N1)C1=CC=NC=C1)NS(=O)(=O)CCC1=CC=CC=C1)OC1=C(C=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4,6-dichloro-5-(2-methoxyphenoxy)-2-(4-pyridyl)-pyrimidine (2 g) and 2-phenyl-ethanesulfonic acid amide potassium salt (2.82 g, Referential Example 1e) in DMF (50 ml) was stirred at rt for 16 h. Bulk of the solvent was evaporated before it was diluted with diethyl ether (50 ml). The mixture was acidified ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Aromatic halide | Sulfonamide | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccncc1.c1ccccc1 | HCl | CN(C)C=O | null | null | COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1Cl.NS(=O)(=O)CCc1ccccc1>CN(C)C=O>COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1NS(=O)(=O)CCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1651722f46a94c749ccc1cc5a9bbb235 | COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1NS(=O)(=O)CCc1ccccc1.OCCO>>COc1ccccc1Oc1c(NS(=O)(=O)CCc2ccccc2)nc(-c2ccncc2)nc1OCCO | [H-].[Na+].C(CO)O.[H-].[Na+].ClC1=C(C(=NC(=N1)C1=CC=NC=C1)NS(=O)(=O)CCC1=CC=CC=C1)OC1=C(C=CC=C1)OC>>OCCOC1=C(C(=NC(=N1)C1=CC=NC=C1)NS(=O)(=O)CCC1=CC=CC=C1)OC1=C(C=CC=C1)OC | Cl[c:33]1[c:10]([O:9][c:8]2[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]2)[c:11]([NH:12][S:13](=[O:14])(=[O:15])[CH2:16][CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[n:24][c:25](-[c:26]2[cH:27][cH:28][n:29][cH:30][cH:31]2)[n:32]1.[OH:34][CH2:35][CH2:36][OH:37]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[O:9]... | COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1NS(=O)(=O)CCc1ccccc1.OCCO | COc1ccccc1Oc1c(NS(=O)(=O)CCc2ccccc2)nc(-c2ccncc2)nc1OCCO | null | null | CC(OCC)=O.COCCOC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a445000eb5ed501274d93689ad5b9d45095af02deca02b6b541c8a834890a276 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | O=S(=O)(CCc1ccccc1)Nc1nc(-c2ccncc2)ncc1Oc1ccccc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](-[#7:7]):[c:8]:1-[#8:9].[C:10]-[C:11]-[OH;D1;+0:12]>>[#7:7]-[c:6]1:[#7;a:5]:[c:3](-[c:4]):[#7;a:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:12]-[C:11]-[C:10]):[c:8]:1-[#8:9] | null | [] | 90 | CELSIUS | 16 | HOUR | To a suspension of NaH (644 mg, 60% in mineral oil) in DME (15 ml) was added ethylene glycol (15 ml). After evolution of gas had ceased, 2-phenyl-ethanesulfonic acid [6-chloro-5-(2-methoxy-phenoxy)-2-pyridin-4-yl-pyrimidin-4-yl]-amide (800 mg) was added and the resulting solution was stirred at 90° C. for 16 h. A furth... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cncnc1 | c1cncnc1 | c1ccccc1.c1ccccc1.c1cncnc1.c1ccncc1 | HCl | CC(OCC)=O.COCCOC | 90 | 16 | COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1NS(=O)(=O)CCc1ccccc1.OCCO>CC(OCC)=O.COCCOC>COc1ccccc1Oc1c(NS(=O)(=O)CCc2ccccc2)nc(-c2ccncc2)nc1OCCO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9112175213df4b35b132a5d7ccb85bbe | COc1ccccc1Oc1c(Cl)nc(-c2ncccn2)nc1Cl.Cc1ccc(-c2c(NS(=O)(=O)CCc3ccccc3)ncnc2OCCO)cc1>>COc1ccccc1Oc1c(Cl)nc(-c2ncccn2)nc1NS(=O)(=O)CCc1ccccc1 | ClC1=NC(=NC(=C1OC1=C(C=CC=C1)OC)Cl)C1=NC=CC=N1.OCCOC1=C(C(=NC=N1)NS(=O)(=O)CCC1=CC=CC=C1)C1=CC=C(C=C1)C>>ClC1=C(C(=NC(=N1)C1=NC=CC=N1)NS(=O)(=O)CCC1=CC=CC=C1)OC1=C(C=CC=C1)OC | Clc1[c:10]([O:9][c:8]2[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]2)[c:11]([Cl:12])[n:13][c:14](-[c:15]2[n:16][cH:17][cH:18][cH:19][n:20]2)[n:21]1.Cc1ccc(-c2c(OCCO)ncn[c:22]2[NH:23][S:24](=[O:25])(=[O:26])[CH2:27][CH2:28][c:29]2[cH:30][cH:31][cH:32][cH:33][cH:34]2)cc1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[O:... | COc1ccccc1Oc1c(Cl)nc(-c2ncccn2)nc1Cl.Cc1ccc(-c2c(NS(=O)(=O)CCc3ccccc3)ncnc2OCCO)cc1 | COc1ccccc1Oc1c(Cl)nc(-c2ncccn2)nc1NS(=O)(=O)CCc1ccccc1 | null | null | null | Miscellaneous | OtherReaction | 0e6f2567d4c562f14851b1dd7af1104e53febf1b11abb67209ab40b7814aba4d | a4ad9cbe1d770d0f3d821718f8588f982b41c905eae3856a390144d3f315b3f4 | O=S(=O)(CCc1ccccc1)Nc1nc(-c2ncccn2)ncc1Oc1ccccc1 | C-c1:c:c:c(-c2:[c;H0;D3;+0:1](-[#7:2]-[#16:3]):n:c:n:c:2-O-C-C-O):c:c:1.Cl-c1:[n;H0;D2;+0:4]:[c:5](-[c:6](:[#7;a:7]):[#7;a:8]):[#7;a:9]:[c:10](-[Cl;D1;H0:11]):[c;H0;D3;+0:12]:1-[#8:13]-[c:14]>>[#16:3]-[#7:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:4]:[c:5](-[c:6](:[#7;a:7]):[#7;a:8]):[#7;a:9]:[c:10](-[Cl;D1;H0:11]):[c;H0;D3;+0:12]... | null | [] | null | null | null | null | 2-Phenylethanesulfonic acid [6-chloro-5-(2-methoxy-phenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-amide was prepared in analogy to Referential Example 7 from 4,6-dichloro-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-pyrimidine (prepared as disclosed in [6]) and 2-phenylethane sulfonamide potassium salt (Referential Example 1). LC... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Ether.Primary alcohol | Ether | c1cncnc1.c1ccccc1.c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1cncnc1.c1ccccc1 | HCl | null | null | null | COc1ccccc1Oc1c(Cl)nc(-c2ncccn2)nc1Cl.Cc1ccc(-c2c(NS(=O)(=O)CCc3ccccc3)ncnc2OCCO)cc1>>COc1ccccc1Oc1c(Cl)nc(-c2ncccn2)nc1NS(=O)(=O)CCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e984f0b46860489fa5ffafd050372951 | COC(=O)C(Cl)C(=O)OC.COc1cccc(O)c1>>COC(=O)C(Oc1cccc(OC)c1)C(=O)OC | COC(C(C(=O)OC)Cl)=O.COC=1C=C(C=CC1)O.C(=O)([O-])[O-].[K+].[K+]>>COC(C(C(=O)OC)OC1=CC(=CC=C1)OC)=O | Cl[CH:5]([C:3]([O:2][CH3:1])=[O:4])[C:15](=[O:16])[O:17][CH3:18].[OH:6][c:7]1[cH:8][cH:9][cH:10][c:11]([O:12][CH3:13])[cH:14]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([O:6][c:7]1[cH:8][cH:9][cH:10][c:11]([O:12][CH3:13])[cH:14]1)[C:15](=[O:16])[O:17][CH3:18] | COC(=O)C(Cl)C(=O)OC.COc1cccc(O)c1 | COC(=O)C(Oc1cccc(OC)c1)C(=O)OC | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 1abe5687f21dfe01b11318540a21f9edb38806e03f96e75bf8c2106db3fe9462 | 51ddfc8e04785767c04eb49244add5bfc6d44a3e44b55034aace28217a5407e3 | c1ccccc1 | Cl-[CH;D3;+0:1](-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5])-[C:6](=[O;D1;H0:7])-[#8:8]-[C;D1;H3:9].[OH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C;D1;H3:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH;D3;+0:1](-[O;H0;D2;+0:10]-[c:11](:[c:12]):[c:13])-[C:6](=[O;D1;H0:7])-[#8:8]-[C;D1;H3:9] | null | [] | 40 | CELSIUS | 15 | MINUTE | To a solution of 3-methoxyphenol (115 g) in acetone (1000 ml) was added K2CO3 (115 g). The suspension was stirred at 40° C. for 15 min. A solution of dimethylchloromalonate (133 ml) in acetone was added over a period of 45 min. The resulting brown suspension was stirred overnight at 70° C. Finally, the solvent was remo... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ester.Ester.Aromatic alcohol | Ester.Ester.Ether | null | null | c1ccccc1 | HCl | CC(=O)C | 40 | 0.25 | COC(=O)C(Cl)C(=O)OC.COc1cccc(O)c1>CC(=O)C>COC(=O)C(Oc1cccc(OC)c1)C(=O)OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c7258cdcfc7c44909a8bab2d91687812 | COC(=O)C(Oc1cccc(OC)c1)C(=O)OC.N=C(N)N1CCOCC1>>COc1cccc(Oc2c(O)nc(N3CCOCC3)nc2O)c1 | Br.N1(CCOCC1)C(=N)N.COC(C(C(=O)OC)OC1=CC(=CC=C1)OC)=O.C[O-].[Na+]>>COC=1C=C(OC=2C(=NC(=NC2O)N2CCOCC2)O)C=CC1 | CO[C:10]([CH:9]([O:8][c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:23]1)[C:21](OC)=[O:22])=[O:11].[NH2:12][C:13]([N:14]1[CH2:15][CH2:16][O:17][CH2:18][CH2:19]1)=[NH:20]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([O:8][c:9]2[c:10]([OH:11])[n:12][c:13]([N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)[n:20][c:21]2[OH:22])... | COC(=O)C(Oc1cccc(OC)c1)C(=O)OC.N=C(N)N1CCOCC1 | COc1cccc(Oc2c(O)nc(N3CCOCC3)nc2O)c1 | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | 796aa162e0a30c54f338ba814a50cc53fed7c215d3c57f65326fb9776d23e139 | a50cc796d897bf9b166ec1e8e95b10119ae9505acba8e8cb752173a4740126a8 | c1ccc(Oc2cnc(N3CCOCC3)nc2)cc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[CH;D3;+0:3](-[#8:4]-[c:5])-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-O-C.[C:8]-[#7:9](-[C;H0;D3;+0:10](-[NH2;D1;+0:11])=[NH;D1;+0:12])-[C:13]>>[C:8]-[#7:9](-[c;H0;D3;+0:10]1:[n;H0;D2;+0:11]:[c;H0;D3;+0:1](-[OH;D1;+0:2]):[c;H0;D3;+0:3](-[#8:4]-[c:5]):[c;H0;D3;+0:6](-[OH;D1;+0:7]):[n;H0;D2;+0:1... | 75.7 | [{"value": 75.7, "product": "COC=1C=C(OC=2C(=NC(=NC2O)N2CCOCC2)O)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | To a solution of dimethyl-(3-methoxyphenoxy)-malonate (11.19 g) in methanol (100 ml) was added sodium methylate (6.48 g). The yellow solution was stirred for 6 h at rt. Then, morpholine-4-carboxamidine hydrobromide (8.40 g) was added and the mixture was stirred at rt for 16 h. The solvent was removed in vacuo and the r... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ether.Primary amine | Ether.Aromatic alcohol.Aromatic alcohol | null | c1cncnc1 | c1ccccc1.c1cncnc1.C1COCC[NH]1 | HO- | CO | null | 6 | COC(=O)C(Oc1cccc(OC)c1)C(=O)OC.N=C(N)N1CCOCC1>CO>COc1cccc(Oc2c(O)nc(N3CCOCC3)nc2O)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-50b2dcef9ed84e548750be65d0cf0b62 | COc1cccc(Oc2c(Cl)nc(N3CCOCC3)nc2Cl)c1.NS(=O)(=O)CCc1ccccc1>>COc1cccc(Oc2c(Cl)nc(N3CCOCC3)nc2NS(=O)(=O)CCc2ccccc2)c1 | ClC1=NC(=NC(=C1OC1=CC(=CC=C1)OC)Cl)N1CCOCC1.[K].C1(=CC=CC=C1)CCS(=O)(=O)N>>ClC1=C(C(=NC(=N1)N1CCOCC1)NS(=O)(=O)CCC1=CC=CC=C1)OC1=CC(=CC=C1)OC | Cl[c:21]1[c:9]([O:8][c:7]2[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:34]2)[c:10]([Cl:11])[n:12][c:13]([N:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)[n:20]1.[NH2:22][S:23](=[O:24])(=[O:25])[CH2:26][CH2:27][c:28]1[cH:29][cH:30][cH:31][cH:32][cH:33]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([O:8][c:9]2[c:10]([Cl:11])[n:1... | COc1cccc(Oc2c(Cl)nc(N3CCOCC3)nc2Cl)c1.NS(=O)(=O)CCc1ccccc1 | COc1cccc(Oc2c(Cl)nc(N3CCOCC3)nc2NS(=O)(=O)CCc2ccccc2)c1 | null | null | CS(=O)C.O | Heteroatom Alkylation and Arylation | OtherReaction | 345edf40ad678aea0250ec5b3d6cc512d8eac020b2f4324f423c18b59726753e | e7974806b40218fa965bb62bf9c430cac38870897b20726116f8b48ae128dc55 | O=S(=O)(CCc1ccccc1)Nc1nc(N2CCOCC2)ncc1Oc1ccccc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6](-[Cl;D1;H0:7]):[c:8]:1-[#8:9].[C:10]-[#16:11](-[NH2;D1;+0:12])(=[O;D1;H0:13])=[O;D1;H0:14]>>[#7:4]-[c:3]1:[#7;a:5]:[c:6](-[Cl;D1;H0:7]):[c:8](-[#8:9]):[c;H0;D3;+0:1](-[NH;D2;+0:12]-[#16:11](-[C:10])(=[O;D1;H0:13])=[O;D1;H0:14]):[#7;a:2]:1 | 90.3 | [{"value": 90.3, "product": "ClC1=C(C(=NC(=N1)N1CCOCC1)NS(=O)(=O)CCC1=CC=CC=C1)OC1=CC(=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-[4,6-dichloro-5-(3-methoxy-phenoxy)-pyrimidin-2-yl]-morpholine (1.0 g) and 2-phenyl-ethanesulfonic acid amide potassium salt (1.57 g, Referential Example 1e) in DMSO (15 ml) was stirred at 60° C. for 24 h. The solution was diluted with water (75 ml) and extracted twice with diethyl ether (75 ml) before ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Aromatic halide | Sulfonamide | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.C1COCC[NH]1.c1ccccc1 | HCl | CS(=O)C.O | null | null | COc1cccc(Oc2c(Cl)nc(N3CCOCC3)nc2Cl)c1.NS(=O)(=O)CCc1ccccc1>CS(=O)C.O>COc1cccc(Oc2c(Cl)nc(N3CCOCC3)nc2NS(=O)(=O)CCc2ccccc2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d9955e3e540d4e58a5a30ceda7476e84 | COc1cccc(Oc2c(Cl)nc(N3CCOCC3)nc2NS(=O)(=O)CCc2ccccc2)c1.OCCO>>COc1cccc(Oc2c(NS(=O)(=O)CCc3ccccc3)nc(N3CCOCC3)nc2OCCO)c1 | ClC1=C(C(=NC(=N1)N1CCOCC1)NS(=O)(=O)CCC1=CC=CC=C1)OC1=CC(=CC=C1)OC.C(CO)O>>OCCOC1=C(C(=NC(=N1)N1CCOCC1)NS(=O)(=O)CCC1=CC=CC=C1)OC1=CC(=CC=C1)OC | Cl[c:32]1[c:9]([O:8][c:7]2[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:37]2)[c:10]([NH:11][S:12](=[O:13])(=[O:14])[CH2:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[n:23][c:24]([N:25]2[CH2:26][CH2:27][O:28][CH2:29][CH2:30]2)[n:31]1.[OH:33][CH2:34][CH2:35][OH:36]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([O:8][c:... | COc1cccc(Oc2c(Cl)nc(N3CCOCC3)nc2NS(=O)(=O)CCc2ccccc2)c1.OCCO | COc1cccc(Oc2c(NS(=O)(=O)CCc3ccccc3)nc(N3CCOCC3)nc2OCCO)c1 | null | null | C(CC(O)(C(=O)O)CC(=O)O)(=O)O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a445000eb5ed501274d93689ad5b9d45095af02deca02b6b541c8a834890a276 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | O=S(=O)(CCc1ccccc1)Nc1nc(N2CCOCC2)ncc1Oc1ccccc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6](-[#7:7]):[c:8]:1-[#8:9].[C:10]-[C:11]-[OH;D1;+0:12]>>[#7:7]-[c:6]1:[#7;a:5]:[c:3](-[#7:4]):[#7;a:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:12]-[C:11]-[C:10]):[c:8]:1-[#8:9] | null | [] | 100 | CELSIUS | 12 | DAY | A suspension of 2-phenyl-ethanesulfonic acid [6-chloro-5-(3-methoxy-phenoxy)-2-morpholin-4-yl-pyrimidin-4-yl]-amide (1.27 g) in ethylene glycol (12 ml) was treated with K-tert.-butylate (2.82 g). The resulting solution was stirred at 100° C. for 12 d. The solution was cooled to rt, diluted with 10% aq. citric acid (150... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cncnc1 | c1cncnc1 | c1ccccc1.c1ccccc1.c1cncnc1.C1COCC[NH]1 | HCl | C(CC(O)(C(=O)O)CC(=O)O)(=O)O | 100 | 288 | COc1cccc(Oc2c(Cl)nc(N3CCOCC3)nc2NS(=O)(=O)CCc2ccccc2)c1.OCCO>C(CC(O)(C(=O)O)CC(=O)O)(=O)O>COc1cccc(Oc2c(NS(=O)(=O)CCc3ccccc3)nc(N3CCOCC3)nc2OCCO)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-328b84d8da60496abda56ebd596892ca | N.O=S(=O)(Cl)CCc1cccs1>>NS(=O)(=O)CCc1cccs1 | Cl.S1C(=CC=C1)CCS(=O)(=O)Cl.N>>S1C(=CC=C1)CCS(=O)(=O)N | [NH3:1].Cl[S:2](=[O:3])(=[O:4])[CH2:5][CH2:6][c:7]1[cH:8][cH:9][cH:10][s:11]1>>[NH2:1][S:2](=[O:3])(=[O:4])[CH2:5][CH2:6][c:7]1[cH:8][cH:9][cH:10][s:11]1 | N.O=S(=O)(Cl)CCc1cccs1 | NS(=O)(=O)CCc1cccs1 | null | null | C1CCOC1 | Miscellaneous | OtherReaction | 419151dfc49d0719bc8d3fc5b23cdd08248d27df18761ee59c11624194c4c5ab | ae33b93faeb632e8ec1263862cc7a6f628747ed893339f281ddf88c6e380b60a | c1ccsc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4]-[C:5].[NH3;D0;+0:6]>>[C:5]-[C:4]-[S;H0;D4;+0:1](-[NH2;D1;+0:6])(=[O;D1;H0:2])=[O;D1;H0:3] | null | [] | null | null | 16 | HOUR | A solution of crude 2-thiophen-2-yl-ethanesulfonyl chloride (25 g) in THF (400 ml) was treated with sat. aq. ammonia (60 ml) at 0° C. The mixture was stirred at rt for 16 h before it was neutralised with 25% aq. HCl (60 ml). Bulk of the THF was evaporated. The aq. solution was extracted twice with EA. The organic phase... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | Sulfonamide | null | null | c1ccsc1 | HCl | C1CCOC1 | null | 16 | N.O=S(=O)(Cl)CCc1cccs1>C1CCOC1>NS(=O)(=O)CCc1cccs1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e37da2d3f11443b5b8ecacc187d5f905 | COC(=O)Cc1ccc(Cl)cc1.COC(=O)OC>>COC(=O)C(C(=O)OC)c1ccc(Cl)cc1 | COC(OC)=O.COC(CC1=CC=C(C=C1)Cl)=O.[H-].[Na+].Cl>>COC(C(C(=O)OC)C1=CC=C(C=C1)Cl)=O | [CH2:5]([C:6](=[O:7])[O:8][CH3:9])[c:10]1[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]1.CO[C:3]([O:2][CH3:1])=[O:4]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([C:6](=[O:7])[O:8][CH3:9])[c:10]1[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]1 | COC(=O)Cc1ccc(Cl)cc1.COC(=O)OC | COC(=O)C(C(=O)OC)c1ccc(Cl)cc1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 69ad31798612cc024412db069fd4b3f753274b5ebc165452c0b89ef436d4a3ab | eeabb7f2ce16e721442da76c0e2b13b4cc973fc4801d0657325337ef5e588f96 | c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[C;D1;H3:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[CH2;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[C;D1;H3:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:9](-[C:7](=[O;D1;H0:8])-[#8:6]-[C;D1;H3:5])-[c:10](:[c:11]):[c:12] | null | [] | null | null | 40 | MINUTE | At 35° C. a solution of 4-chlorophenylacetic acid methyl ester (52 g) in THF (170 ml) was carefully added over a period of 70 min to a suspension of NaH (15.6 g) in dry THF (550 ml). Stirring was continued for 40 min without heating and the temperature dropped to 290C. The evolution of gas had stopped before dimethylca... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Ester | Ester.Ester | null | null | c1ccccc1 | HO- | C1CCOC1 | null | 0.666667 | COC(=O)Cc1ccc(Cl)cc1.COC(=O)OC>C1CCOC1>COC(=O)C(C(=O)OC)c1ccc(Cl)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b4421387e1174e2989ff360b17023739 | COC(=O)C(C(=O)OC)c1ccc(Cl)cc1.N=CN>>Oc1ncnc(O)c1-c1ccc(Cl)cc1 | COC(C(C(=O)OC)C1=CC=C(C=C1)Cl)=O.C[O-].[Na+].Cl.C(=N)N>>ClC1=CC=C(C=C1)C=1C(=NC=NC1O)O | CO[C:2](=[O:1])[CH:8]([C:6](OC)=[O:7])[c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]1.[NH:3]=[CH:4][NH2:5]>>[OH:1][c:2]1[n:3][cH:4][n:5][c:6]([OH:7])[c:8]1-[c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]1 | COC(=O)C(C(=O)OC)c1ccc(Cl)cc1.N=CN | Oc1ncnc(O)c1-c1ccc(Cl)cc1 | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | d507ea5e988c6bcfe927f1b3a86f934f8a1c706f38171153cdf4dbd7aeb28e83 | 6504f33921726f64e36c5f3f322459b73652319c83071522ec21b8b88a33a5a7 | c1ccc(-c2cncnc2)cc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[CH;D3;+0:3](-[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-O-C)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10].[NH2;D1;+0:11]-[CH;D2;+0:12]=[NH;D1;+0:13]>>[OH;D1;+0:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:13]:[cH;D2;+0:12]:[n;H0;D2;+0:11]:[c;H0;D3;+0:4](-[OH;D1;+0:5]):[c;H0;D3;+0:3]:1-[c;H0;D3;+0:6](:[c:7]:[c:... | 94.8 | [{"value": 94.8, "product": "ClC1=CC=C(C=C1)C=1C(=NC=NC1O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | A solution of 2-(4-chlorophenyl)-malonic acid dimethyl ester (18.90 g) in methanol (200 ml) was added dropwise at 0° C. to a solution sodium methylate (14.60 g) in methanol (150 ml). The mixture was stirred for 1 h at 0° C. before formamidine hydrochloride (7.66 g) was added. The suspension was stirred at rt for 20 h. ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Primary amine | Aromatic alcohol.Aromatic alcohol | null | c1cncnc1 | c1cncnc1.c1ccccc1 | HO- | CO | null | 20 | COC(=O)C(C(=O)OC)c1ccc(Cl)cc1.N=CN>CO>Oc1ncnc(O)c1-c1ccc(Cl)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c9c2f8cbb6934fe4be43d947331b2f89 | Clc1ccc(-c2c(Cl)ncnc2Cl)cc1.NS(=O)(=O)CCc1cccs1>>O=S(=O)(CCc1cccs1)Nc1ncnc(Cl)c1-c1ccc(Cl)cc1 | ClC1=NC=NC(=C1C1=CC=C(C=C1)Cl)Cl.[K].S1C(=CC=C1)CCS(=O)(=O)N.CCN(C(C)C)C(C)C>>ClC1=C(C(=NC=N1)NS(=O)(=O)CCC=1SC=CC1)C1=CC=C(C=C1)Cl | Cl[c:12]1[n:13][cH:14][n:15][c:16]([Cl:17])[c:18]1-[c:19]1[cH:20][cH:21][c:22]([Cl:23])[cH:24][cH:25]1.[O:1]=[S:2](=[O:3])([CH2:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][s:10]1)[NH2:11]>>[O:1]=[S:2](=[O:3])([CH2:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][s:10]1)[NH:11][c:12]1[n:13][cH:14][n:15][c:16]([Cl:17])[c:18]1-[c:19]1[cH:20][cH:2... | Clc1ccc(-c2c(Cl)ncnc2Cl)cc1.NS(=O)(=O)CCc1cccs1 | O=S(=O)(CCc1cccs1)Nc1ncnc(Cl)c1-c1ccc(Cl)cc1 | null | null | CS(=O)C.O | Heteroatom Alkylation and Arylation | OtherReaction | 345edf40ad678aea0250ec5b3d6cc512d8eac020b2f4324f423c18b59726753e | e7974806b40218fa965bb62bf9c430cac38870897b20726116f8b48ae128dc55 | O=S(=O)(CCc1cccs1)Nc1ncncc1-c1ccccc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[Cl;D1;H0:6]):[c:7]:1-[c:8].[C:9]-[#16:10](-[NH2;D1;+0:11])(=[O;D1;H0:12])=[O;D1;H0:13]>>[C:9]-[#16:10](=[O;D1;H0:12])(=[O;D1;H0:13])-[NH;D2;+0:11]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[Cl;D1;H0:6]):[c:7]:1-[c:8] | 68.7 | [{"value": 68.7, "product": "ClC1=C(C(=NC=N1)NS(=O)(=O)CCC=1SC=CC1)C1=CC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4,6-dichloro-5-(4-chlorophenyl)pyrimidine (848 mg), 2-thiophen-2-yl-ethanesulfonic acid amide potassium salt (1.5 g, Referential Example 14) and Hunig's base (1 ml) in DMSO (20 ml) was stirred at rt for 24 h before it was diluted with water (200 ml) and extracted twice with diethyl ether. The aqueous laye... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Aromatic halide | Sulfonamide | c1cncnc1 | c1cncnc1 | c1ccsc1.c1cncnc1.c1ccccc1 | HCl | CS(=O)C.O | null | null | Clc1ccc(-c2c(Cl)ncnc2Cl)cc1.NS(=O)(=O)CCc1cccs1>CS(=O)C.O>O=S(=O)(CCc1cccs1)Nc1ncnc(Cl)c1-c1ccc(Cl)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8a743ff8858e40c99c6d6143fe72b8cd | O=C(O)CC(O)(CC(=O)O)C(=O)O.O=S(=O)(CCc1cccs1)Nc1ncnc(Cl)c1-c1ccc(Cl)cc1>>O=S(=O)(CCc1cccs1)Nc1ncnc(OCCO)c1-c1ccc(Cl)cc1 | ClC1=C(C(=NC=N1)NS(=O)(=O)CCC=1SC=CC1)C1=CC=C(C=C1)Cl.C(CC(O)(C(=O)O)CC(=O)O)(=O)O>>ClC1=CC=C(C=C1)C=1C(=NC=NC1OCCO)NS(=O)(=O)CCC=1SC=CC1 | O=C(O)CC(C(=O)O)([OH:17])[CH2:18][C:19](=O)[OH:20].Cl[c:16]1[n:15][cH:14][n:13][c:12]([NH:11][S:2](=[O:1])(=[O:3])[CH2:4][CH2:5][c:6]2[cH:7][cH:8][cH:9][s:10]2)[c:21]1-[c:22]1[cH:23][cH:24][c:25]([Cl:26])[cH:27][cH:28]1>>[O:1]=[S:2](=[O:3])([CH2:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][s:10]1)[NH:11][c:12]1[n:13][cH:14][n:15]... | O=C(O)CC(O)(CC(=O)O)C(=O)O.O=S(=O)(CCc1cccs1)Nc1ncnc(Cl)c1-c1ccc(Cl)cc1 | O=S(=O)(CCc1cccs1)Nc1ncnc(OCCO)c1-c1ccc(Cl)cc1 | null | null | C(CO)O.O | Heteroatom Alkylation and Arylation | OtherReaction | b18ba87fb2ec0987a978e901bb5a53033e53fbf47b9296eda6a432ff7972ccf1 | 0d57d11c1ca6b9fbb36ccec54ea803b423eb00045b608c0a6b2fdbd90fbd86af | O=S(=O)(CCc1cccs1)Nc1ncncc1-c1ccccc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]):[c:7]:1-[c:8].O-C(=O)-C-C(-[OH;D1;+0:9])(-[CH2;D2;+0:10]-[C;H0;D3;+0:11](=O)-[O;D1;H1:12])-C(-O)=O>>[#7:6]-[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:9]-[CH2;D2;+0:10]-[CH2;D2;+0:11]-[O;D1;H1:12]):[c:7]:1-[c:8] | null | [] | 110 | CELSIUS | 12 | HOUR | 2-Thiophen-2-yl-ethanesulfonic acid [6-chloro-5-(4-chloro-phenyl)-pyrimidin-4-yl]-amide (930 mg) was added to a solution of K-tert. butylate (1.16 g) in ethylene glycol (10 ml). The mixture was stirred at 110° C. for 12 h before it was diluted with water (150 ml), acidified with 10% aq. citric acid (13 ml). The resulti... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carboxylic acid.Carboxylic acid.Carboxylic acid.Tertiary alcohol | Ether.Primary alcohol | c1cncnc1 | c1cncnc1 | c1ccsc1.c1cncnc1.c1ccccc1 | HCl | C(CO)O.O | 110 | 12 | O=C(O)CC(O)(CC(=O)O)C(=O)O.O=S(=O)(CCc1cccs1)Nc1ncnc(Cl)c1-c1ccc(Cl)cc1>C(CO)O.O>O=S(=O)(CCc1cccs1)Nc1ncnc(OCCO)c1-c1ccc(Cl)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-42c3a2963f314b3f80a28108b2f9c847 | COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1Cl.NS(=O)(=O)CCc1ccccn1>>COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1NS(=O)(=O)CCc1ccccn1 | ClC1=NC(=NC(=C1OC1=C(C=CC=C1)OC)Cl)C1=CC=NC=C1.[K].N1=C(C=CC=C1)CCS(=O)(=O)N.C(C)N(CC)CC>>ClC1=C(C(=NC(=N1)C1=CC=NC=C1)NS(=O)(=O)CCC1=NC=CC=C1)OC1=C(C=CC=C1)OC | Cl[c:22]1[c:10]([O:9][c:8]2[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]2)[c:11]([Cl:12])[n:13][c:14](-[c:15]2[cH:16][cH:17][n:18][cH:19][cH:20]2)[n:21]1.[NH2:23][S:24](=[O:25])(=[O:26])[CH2:27][CH2:28][c:29]1[cH:30][cH:31][cH:32][cH:33][n:34]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[O:9][c:10]1[c:11]([Cl:12])[... | COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1Cl.NS(=O)(=O)CCc1ccccn1 | COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1NS(=O)(=O)CCc1ccccn1 | null | null | CS(=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 345edf40ad678aea0250ec5b3d6cc512d8eac020b2f4324f423c18b59726753e | e7974806b40218fa965bb62bf9c430cac38870897b20726116f8b48ae128dc55 | O=S(=O)(CCc1ccccn1)Nc1nc(-c2ccncc2)ncc1Oc1ccccc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](-[Cl;D1;H0:7]):[c:8]:1-[#8:9].[C:10]-[#16:11](-[NH2;D1;+0:12])(=[O;D1;H0:13])=[O;D1;H0:14]>>[#8:9]-[c:8]1:[c:6](-[Cl;D1;H0:7]):[#7;a:5]:[c:3](-[c:4]):[#7;a:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:12]-[#16:11](-[C:10])(=[O;D1;H0:13])=[O;D1;H0:14] | 38 | [{"value": 38.0, "product": "ClC1=C(C(=NC(=N1)C1=CC=NC=C1)NS(=O)(=O)CCC1=NC=CC=C1)OC1=C(C=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 96 | HOUR | A solution of 4,6-dichloro-5-(2-methoxyphenoxy)-2-(4-pyridyl)-pyrimidine (1.75 g, Referential Example 7) and 2-pyridin-2-yl-ethanesulfonic acid amide potassium salt (1.13 g) in DMSO (30 ml) was stirred at rt for 24 h. Triethylamine (657 mg) was added and stirring was continued for another 96 h before the mixture was di... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Aromatic halide | Sulfonamide | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccncc1.c1ccncc1 | HCl | CS(=O)C.C(C)(=O)OCC | null | 96 | COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1Cl.NS(=O)(=O)CCc1ccccn1>CS(=O)C.C(C)(=O)OCC>COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1NS(=O)(=O)CCc1ccccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e28236ae2b274d9c96885e7fe9ca69d9 | COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1NS(=O)(=O)CCc1ccccn1.OCCO>>COc1ccccc1Oc1c(NS(=O)(=O)CCc2ccccn2)nc(-c2ccncc2)nc1OCCO | Cl.C(CO)O.[H-].[Na+].ClC1=C(C(=NC(=N1)C1=CC=NC=C1)NS(=O)(=O)CCC1=NC=CC=C1)OC1=C(C=CC=C1)OC>>OCCOC1=C(C(=NC(=N1)C1=CC=NC=C1)NS(=O)(=O)CCC1=NC=CC=C1)OC1=C(C=CC=C1)OC | Cl[c:33]1[c:10]([O:9][c:8]2[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]2)[c:11]([NH:12][S:13](=[O:14])(=[O:15])[CH2:16][CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][n:23]2)[n:24][c:25](-[c:26]2[cH:27][cH:28][n:29][cH:30][cH:31]2)[n:32]1.[OH:34][CH2:35][CH2:36][OH:37]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[O:9][... | COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1NS(=O)(=O)CCc1ccccn1.OCCO | COc1ccccc1Oc1c(NS(=O)(=O)CCc2ccccn2)nc(-c2ccncc2)nc1OCCO | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a445000eb5ed501274d93689ad5b9d45095af02deca02b6b541c8a834890a276 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | O=S(=O)(CCc1ccccn1)Nc1nc(-c2ccncc2)ncc1Oc1ccccc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](-[#7:7]):[c:8]:1-[#8:9].[C:10]-[C:11]-[OH;D1;+0:12]>>[#7:7]-[c:6]1:[#7;a:5]:[c:3](-[c:4]):[#7;a:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:12]-[C:11]-[C:10]):[c:8]:1-[#8:9] | null | [] | 90 | CELSIUS | 40 | HOUR | To a suspension of NaH (701 mg, 60% in mineral oil) in DMF (15 ml) was added ethylene glycol (15 ml). After the evolution of gas had ceased, 2-pyridin-2-yl-ethanesulfonic acid [6-chloro-5-(2-methoxy-phenoxy)-2-pyridin-4-yl-pyrimidin-4-yl]-amide (800 mg) was added and the resulting solution was stirred at 90° C. for 40 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cncnc1 | c1cncnc1 | c1ccccc1.c1ccncc1.c1cncnc1.c1ccncc1 | HCl | CN(C)C=O | 90 | 40 | COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1NS(=O)(=O)CCc1ccccn1.OCCO>CN(C)C=O>COc1ccccc1Oc1c(NS(=O)(=O)CCc2ccccn2)nc(-c2ccncc2)nc1OCCO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d079313d911f414dad920cc4c299001d | Cc1ccc(-c2c(NS(=O)(=O)CCc3ccccc3)ncnc2OCCO)cc1.Clc1ncccn1>>Cc1ccc(-c2c(NS(=O)(=O)CCc3ccccc3)ncnc2OCCOc2ncccn2)cc1 | [H-].[Na+].OCCOC1=C(C(=NC=N1)NS(=O)(=O)CCC1=CC=CC=C1)C1=CC=C(C=C1)C.ClC1=NC=CC=N1>>N1=C(N=CC=C1)OCCOC1=C(C(=NC=N1)NS(=O)(=O)CCC1=CC=CC=C1)C1=CC=C(C=C1)C | [CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c:7]([NH:8][S:9](=[O:10])(=[O:11])[CH2:12][CH2:13][c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[n:20][cH:21][n:22][c:23]2[O:24][CH2:25][CH2:26][OH:27])[cH:34][cH:35]1.Cl[c:28]1[n:29][cH:30][cH:31][cH:32][n:33]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c:7]([NH:8][S:9](=[O:10])(=[O:1... | Cc1ccc(-c2c(NS(=O)(=O)CCc3ccccc3)ncnc2OCCO)cc1.Clc1ncccn1 | Cc1ccc(-c2c(NS(=O)(=O)CCc3ccccc3)ncnc2OCCOc2ncccn2)cc1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a445000eb5ed501274d93689ad5b9d45095af02deca02b6b541c8a834890a276 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | O=S(=O)(CCc1ccccc1)Nc1ncnc(OCCOc2ncccn2)c1-c1ccccc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | 74.6 | [{"value": 74.6, "product": "N1=C(N=CC=C1)OCCOC1=C(C(=NC=N1)NS(=O)(=O)CCC1=CC=CC=C1)C1=CC=C(C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 17 | HOUR | To sodium hydride (50 mg, 60% in mineral oil) was added THF (25 ml) followed by 2-phenyl-ethanesulfonic acid [6-(2-hydroxy-ethoxy)-5-p-tolyl-pyrimidin-4-yl]-amide (150 mg, Referential Example 1). The mixture was stirred for 1 h at rt before 2-chloro-pyrimidine (86 mg) was added. Stirring was continued for 17 h at 80° C... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cncnc1 | c1cncnc1 | c1ccccc1.c1ccccc1.c1cncnc1.c1cncnc1 | HCl | C1CCOC1 | 0 | 17 | Cc1ccc(-c2c(NS(=O)(=O)CCc3ccccc3)ncnc2OCCO)cc1.Clc1ncccn1>C1CCOC1>Cc1ccc(-c2c(NS(=O)(=O)CCc3ccccc3)ncnc2OCCOc2ncccn2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7ba9c64b1ade4f3bbbe979f0ff322f01 | Cc1ccc(-c2c(NS(=O)(=O)CCc3ccccc3)ncnc2OCCO)cc1.FC(F)(F)c1ccc(Cl)nc1>>Cc1ccc(-c2c(NS(=O)(=O)CCc3ccccc3)ncnc2OCCOc2ccc(C(F)(F)F)cn2)cc1 | [H-].[Na+].OCCOC1=C(C(=NC=N1)NS(=O)(=O)CCC1=CC=CC=C1)C1=CC=C(C=C1)C.ClC1=NC=C(C=C1)C(F)(F)F>>C1(=CC=C(C=C1)C=1C(=NC=NC1OCCOC1=NC=C(C=C1)C(F)(F)F)NS(=O)(=O)CCC1=CC=CC=C1)C | [CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c:7]([NH:8][S:9](=[O:10])(=[O:11])[CH2:12][CH2:13][c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[n:20][cH:21][n:22][c:23]2[O:24][CH2:25][CH2:26][OH:27])[cH:38][cH:39]1.Cl[c:28]1[cH:29][cH:30][c:31]([C:32]([F:33])([F:34])[F:35])[cH:36][n:37]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c... | Cc1ccc(-c2c(NS(=O)(=O)CCc3ccccc3)ncnc2OCCO)cc1.FC(F)(F)c1ccc(Cl)nc1 | Cc1ccc(-c2c(NS(=O)(=O)CCc3ccccc3)ncnc2OCCOc2ccc(C(F)(F)F)cn2)cc1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | ea617b323b892eda23f5ae30e789991ea9692064ef355a16e8ed81c16e743d2b | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | O=S(=O)(CCc1ccccc1)Nc1ncnc(OCCOc2ccccn2)c1-c1ccccc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 88.8 | [{"value": 88.8, "product": "C1(=CC=C(C=C1)C=1C(=NC=NC1OCCOC1=NC=C(C=C1)C(F)(F)F)NS(=O)(=O)CCC1=CC=CC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 17 | HOUR | To sodium hydride (27 mg, 60% in mineral oil) was added THF (15 ml) followed by 2-phenyl-ethanesulfonic acid [6-(2-hydroxy-ethoxy)-5-p-tolyl-pyrimidin-4-yl]-amide (80 mg, Referential Example 1). The mixture was stirred for 1 h at rt before 2-chloro-5-trifluoromethyl-pyridine (86 mg) was added. Stirring was continued fo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccccc1.c1cncnc1.c1ccncc1 | HCl | C1CCOC1 | null | 17 | Cc1ccc(-c2c(NS(=O)(=O)CCc3ccccc3)ncnc2OCCO)cc1.FC(F)(F)c1ccc(Cl)nc1>C1CCOC1>Cc1ccc(-c2c(NS(=O)(=O)CCc3ccccc3)ncnc2OCCOc2ccc(C(F)(F)F)cn2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f82597da22f34e6c9d823c81ffb52c3e | Cc1ccc(-c2c(Cl)ncnc2NS(=O)(=O)CCc2ccccc2)cc1.OCCOc1ccc(Br)cc1>>Cc1ccc(-c2c(NS(=O)(=O)CCc3ccccc3)ncnc2OCCOc2ccc(Br)cc2)cc1 | [H-].[Na+].BrC1=CC=C(OCCO)C=C1.ClC1=C(C(=NC=N1)NS(=O)(=O)CCC1=CC=CC=C1)C1=CC=C(C=C1)C>>BrC1=CC=C(OCCOC2=C(C(=NC=N2)NS(=O)(=O)CCC2=CC=CC=C2)C2=CC=C(C=C2)C)C=C1 | Cl[c:23]1[c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:36][cH:35]2)[c:7]([NH:8][S:9](=[O:10])(=[O:11])[CH2:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[n:20][cH:21][n:22]1.[OH:24][CH2:25][CH2:26][O:27][c:28]1[cH:29][cH:30][c:31]([Br:32])[cH:33][cH:34]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c:7]([NH:8][S:9](=[... | Cc1ccc(-c2c(Cl)ncnc2NS(=O)(=O)CCc2ccccc2)cc1.OCCOc1ccc(Br)cc1 | Cc1ccc(-c2c(NS(=O)(=O)CCc3ccccc3)ncnc2OCCOc2ccc(Br)cc2)cc1 | null | null | COCCOC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a445000eb5ed501274d93689ad5b9d45095af02deca02b6b541c8a834890a276 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | O=S(=O)(CCc1ccccc1)Nc1ncnc(OCCOc2ccccc2)c1-c1ccccc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]):[c:7]:1-[c:8].[C:9]-[C:10]-[OH;D1;+0:11]>>[#7:6]-[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:11]-[C:10]-[C:9]):[c:7]:1-[c:8] | 86.7 | [{"value": 86.7, "product": "BrC1=CC=C(OCCOC2=C(C(=NC=N2)NS(=O)(=O)CCC2=CC=CC=C2)C2=CC=C(C=C2)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 16 | HOUR | To a suspension of NaH (17 mg, 60% in mineral oil) in DME (5 ml) was added 2-(4-bromo-phenoxy)-ethanol (111 mg). The mixture was stirred at 50° C. for 1 h before 2-phenyl-ethanesulfonic acid (6-chloro-5-p-tolyl-pyrimidin-4-yl)-amide (100 mg, Referential Example 1f) and K-tert.-butylate (25 mg) was added. The mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cncnc1 | c1cncnc1 | c1ccccc1.c1ccccc1.c1cncnc1.c1ccccc1 | HCl | COCCOC | 70 | 16 | Cc1ccc(-c2c(Cl)ncnc2NS(=O)(=O)CCc2ccccc2)cc1.OCCOc1ccc(Br)cc1>COCCOC>Cc1ccc(-c2c(NS(=O)(=O)CCc3ccccc3)ncnc2OCCOc2ccc(Br)cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-62e21300892c4773a62144aa95cd1bda | CCCBr.CCOC(=O)C(C#N)NC(C)=O>>CCCC(C#N)(NC(C)=O)C(=O)OCC | BrCCC.C(C)(=O)NC(C(=O)OCC)C#N.[Na].BrCCC>>C(C)(=O)NC(C(=O)OCC)(CCC)C#N | Br[CH2:3][CH2:2][CH3:1].[CH:4]([C:5]#[N:6])([NH:7][C:8]([CH3:9])=[O:10])[C:11](=[O:12])[O:13][CH2:14][CH3:15]>>[CH3:1][CH2:2][CH2:3][C:4]([C:5]#[N:6])([NH:7][C:8]([CH3:9])=[O:10])[C:11](=[O:12])[O:13][CH2:14][CH3:15] | CCCBr.CCOC(=O)C(C#N)NC(C)=O | CCCC(C#N)(NC(C)=O)C(=O)OCC | null | null | C(C)O | C-C Coupling | OtherReaction | cce1a125a1ff1ac49e6bca841c71f39abbf2c962f7edb2747b8c98f3307cb502 | 0061a06af9fc64155952582b91b574e4abd8908ca14244f15179c2400b24dd08 | null | Br-[CH2;D2;+0:1]-[C:2]-[C;D1;H3:3].[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[CH;D3;+0:8](-[#7:9]-[C:10](-[C;D1;H3:11])=[O;D1;H0:12])-[C:13]#[N;D1;H0:14]>>[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[C;H0;D4;+0:8](-[#7:9]-[C:10](-[C;D1;H3:11])=[O;D1;H0:12])(-[C:13]#[N;D1;H0:14])-[CH2;D2;+0:1]-[C:2]-[C;D1;H3:3] | null | [] | 0 | CELSIUS | 2 | HOUR | 1.35 g of sodium (58.8 mmol) are dissolved in 200 ml of ethanol and the resulting solution is cooled down to 0° C. 10 g (58.8 mmol) of ethyl acetamidocyanoacetate are added. After a clear solution has formed, a solution of 7.23 g (58.8 mmol) of bromopropane in 10 ml of ethanol is added dropwise and the reaction mixture... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | null | null | null | HBr | C(C)O | 0 | 2 | CCCBr.CCOC(=O)C(C#N)NC(C)=O>C(C)O>CCCC(C#N)(NC(C)=O)C(=O)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ce3fd0b48b39417c9f1ac902d61127bf | CCBr.N#Cc1ccccc1O>>CCOc1ccccc1C#N | OC1=C(C#N)C=CC=C1.C([O-])([O-])=O.[K+].[K+].C(C)Br>>C(C)OC1=C(C#N)C=CC=C1 | Br[CH2:2][CH3:1].[OH:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[C:10]#[N:11]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[C:10]#[N:11] | CCBr.N#Cc1ccccc1O | CCOc1ccccc1C#N | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C;D1;H3:2].[OH;D1;+0:3]-[c:4](:[c:5]):[c:6]>>[C;D1;H3:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:3]-[c:4](:[c:5]):[c:6] | 97.1 | [{"value": 97.0, "product": "C(C)OC1=C(C#N)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.1, "product": "C(C)OC1=C(C#N)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 25 g (210 mmol) of 2-hydroxylbenzonitrile are heated, together with 87 g of potassium carbonate and 34.3 g (314.8 mmol) of ethyl bromide, in 500 ml of acetone under reflux overnight. The solid is filtered off, the solvent is removed in vacuo and the residue is distilled in vacuo. 30.0 g (97%) of a colorless liquid are ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | CC(=O)C | null | null | CCBr.N#Cc1ccccc1O>CC(=O)C>CCOc1ccccc1C#N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b0655c26605e4b4cb0926cd201146d73 | CCCc1nc(C)n2c(=O)[nH]c(-c3ccccc3OCC)nc12.O=S(=O)(O)Cl>>CCCc1nc(C)n2c(=O)[nH]c(-c3cc(S(=O)(=O)Cl)ccc3OCC)nc12 | C(C)OC1=C(C=CC=C1)C1=NC=2N(C(N1)=O)C(=NC2CCC)C.ClS(=O)(=O)O>>C(C)OC1=C(C=C(C=C1)S(=O)(=O)Cl)C1=NC=2N(C(N1)=O)C(=NC2CCC)C | [CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]([CH3:7])[n:8]2[c:9](=[O:10])[nH:11][c:12](-[c:13]3[cH:14][cH:15][cH:20][cH:21][c:22]3[O:23][CH2:24][CH3:25])[n:26][c:27]12.O=[S:16]([OH:17])(=[O:18])[Cl:19]>>[CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]([CH3:7])[n:8]2[c:9](=[O:10])[nH:11][c:12](-[c:13]3[cH:14][c:15]([S:16](=[O:17])(=[O:18... | CCCc1nc(C)n2c(=O)[nH]c(-c3ccccc3OCC)nc12.O=S(=O)(O)Cl | CCCc1nc(C)n2c(=O)[nH]c(-c3cc(S(=O)(=O)Cl)ccc3OCC)nc12 | null | null | ClCCl | Protection | Aromatic sulfonyl chlorination | c55ee9a7393fdf3f247a23f751c8b9bb8a24c2b053414c59e6d87cc0f6e27124 | c731d053565135be022f3edbe36cf28a9b4364ca579bdb183b2db9578bab4695 | O=c1[nH]c(-c2ccccc2)nc2cncn12 | O=[S;H0;D4;+0:1](-[Cl;D1;H0:2])(=[O;D1;H0:3])-[OH;D1;+0:4].[c:5]:[c:6]:[cH;D2;+0:7]:[c:8]:[c:9]>>[Cl;D1;H0:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;H0;D1;+0:4])-[c;H0;D3;+0:7](:[c:6]:[c:5]):[c:8]:[c:9] | 99 | [{"value": 99.0, "product": "C(C)OC1=C(C=C(C=C1)S(=O)(=O)Cl)C1=NC=2N(C(N1)=O)C(=NC2CCC)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | 1.64 g (5.25 mmol) of 2-(2-ethoxyphenyl)-6-methyl-8-propyl-3H-imidazo[1,5-a][1,3,5]triazin-4-one (example VI) are added in portions to 3.14 ml of chlorosulfonic acid while cooling with ice. The reaction mixture is stirred at room temperature for 16 hours, then diluted with dichloromethane and poured onto ice water. The... | 10.6084/m9.figshare.5104873.v1 | null | null | Sulfonyl halide | c1ccccc1 | c1ccccc1 | c1ncn2cncc2n1.c1ccccc1 | HO- | ClCCl | null | 16 | CCCc1nc(C)n2c(=O)[nH]c(-c3ccccc3OCC)nc12.O=S(=O)(O)Cl>ClCCl>CCCc1nc(C)n2c(=O)[nH]c(-c3cc(S(=O)(=O)Cl)ccc3OCC)nc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6f110095d41b437f9aec3433c29d3d1d | CCOc1ccccc1-c1nc2c(C3CCCC3)nc(C)n2c(=O)[nH]1.O=S(=O)(O)Cl>>CCOc1ccc(S(=O)(=O)Cl)cc1-c1nc2c(C3CCCC3)nc(C)n2c(=O)[nH]1 | C1(CCCC1)C=1N=C(N2C1N=C(NC2=O)C2=C(C=CC=C2)OCC)C.ClS(=O)(=O)O>>C(C)OC1=C(C=C(C=C1)S(=O)(=O)Cl)C1=NC=2N(C(N1)=O)C(=NC2C2CCCC2)C | [CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][cH:7][cH:12][c:13]1-[c:14]1[n:15][c:16]2[c:17]([CH:18]3[CH2:19][CH2:20][CH2:21][CH2:22]3)[n:23][c:24]([CH3:25])[n:26]2[c:27](=[O:28])[nH:29]1.O[S:8](=[O:9])(=[O:10])[Cl:11]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([S:8](=[O:9])(=[O:10])[Cl:11])[cH:12][c:13]1-[c:14]1[n:15][c:16]2... | CCOc1ccccc1-c1nc2c(C3CCCC3)nc(C)n2c(=O)[nH]1.O=S(=O)(O)Cl | CCOc1ccc(S(=O)(=O)Cl)cc1-c1nc2c(C3CCCC3)nc(C)n2c(=O)[nH]1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | Aromatic sulfonyl chlorination | 04bb0e110ac9bc3104a40572864ecdd042b39019cff0ea96d1a0ad7c9eb6ecf3 | d32b60b8f9bfd187c6c9f1eef6a22a00f53525a7532b83aba763d5389c9e4280 | O=c1[nH]c(-c2ccccc2)nc2c(C3CCCC3)ncn12 | O-[S;H0;D4;+0:1](-[Cl;D1;H0:2])(=[O;D1;H0:3])=[O;D1;H0:4].[c:5]:[c:6]:[cH;D2;+0:7]:[c:8]:[c:9]>>[Cl;D1;H0:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[c;H0;D3;+0:7](:[c:6]:[c:5]):[c:8]:[c:9] | null | [] | null | null | 8 | HOUR | 372.3 mg (1.1 mmol) of 8-cyclopentyl-2-(2-ethoxy-phenyl)-6-methyl-3H-imidazo[1,5-a][1,3,5]triazin-4-one (example IX) are added in portions to 0.66 ml (9.9 mmol) of ice-cooled chlorosulfonic acid. The mixture is subsequently stirred overnight at room temperature before being diluted with dichloromethane and poured onto ... | 10.6084/m9.figshare.5104873.v1 | null | null | Sulfonyl halide | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CCCC1.c1ncn2cncc2n1 | HO- | ClCCl | null | 8 | CCOc1ccccc1-c1nc2c(C3CCCC3)nc(C)n2c(=O)[nH]1.O=S(=O)(O)Cl>ClCCl>CCOc1ccc(S(=O)(=O)Cl)cc1-c1nc2c(C3CCCC3)nc(C)n2c(=O)[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d2b9031c556f4c90a7f67469ddf953db | CCCc1nc(C)n2c(=O)[nH]c(-c3cc(S(=O)(=O)Cl)ccc3OCC)nc12.OCCN1CCNCC1>>CCCc1nc(C)n2c(=O)[nH]c(-c3cc(S(=O)(=O)N4CCN(CCO)CC4)ccc3OCC)nc12 | OCCN1CCNCC1.C(C)OC1=C(C=C(C=C1)S(=O)(=O)Cl)C1=NC=2N(C(N1)=O)C(=NC2CCC)C>>C(C)OC1=C(C=C(C=C1)S(=O)(=O)N1CCN(CC1)CCO)C1=NC=2N(C(N1)=O)C(=NC2CCC)C | Cl[S:16]([c:15]1[cH:14][c:13](-[c:12]2[nH:11][c:9](=[O:10])[n:8]3[c:6]([CH3:7])[n:5][c:4]([CH2:3][CH2:2][CH3:1])[c:35]3[n:34]2)[c:30]([O:31][CH2:32][CH3:33])[cH:29][cH:28]1)(=[O:17])=[O:18].[NH:19]1[CH2:20][CH2:21][N:22]([CH2:23][CH2:24][OH:25])[CH2:26][CH2:27]1>>[CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]([CH3:7])[n:8]2[c:9... | CCCc1nc(C)n2c(=O)[nH]c(-c3cc(S(=O)(=O)Cl)ccc3OCC)nc12.OCCN1CCNCC1 | CCCc1nc(C)n2c(=O)[nH]c(-c3cc(S(=O)(=O)N4CCN(CCO)CC4)ccc3OCC)nc12 | null | null | ClCCl | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | 8c5bae95a7afc59a07547e375f0b07a72ef45ce3f019f7996b69ec8802313118 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | O=c1[nH]c(-c2cccc(S(=O)(=O)N3CCNCC3)c2)nc2cncn12 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1)-[c:4](:[c:5]):[c:6] | null | [] | null | null | 16 | HOUR | 86 mg (0.66 mmol) of hydroxylethylpiperazine are added to a solution of 90 mg (0.22 mmol) of 4-ethoxy-3-(6-methyl-4-oxo-8-propyl-3,4-dihydro-imidazo[1,5-a][1,3,5]triazin-2-yl)-benzenesulfonyl chloride (example VI) in 5 ml of dichloromethane and the reaction mixture is stirred at room temperature for 16 hours. After chr... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ncn2cncc2n1.c1ccccc1.C1C[NH]CC[NH]1 | HCl | ClCCl | null | 16 | CCCc1nc(C)n2c(=O)[nH]c(-c3cc(S(=O)(=O)Cl)ccc3OCC)nc12.OCCN1CCNCC1>ClCCl>CCCc1nc(C)n2c(=O)[nH]c(-c3cc(S(=O)(=O)N4CCN(CCO)CC4)ccc3OCC)nc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-54768539979e4dcbbd6e3efae4ee2e77 | CCCc1nc(C)n2c(=O)[nH]c(-c3cc(S(=O)(=O)Cl)ccc3OCC)nc12.CN1CCNCC1>>CCCc1nc(C)n2c(=O)[nH]c(-c3cc(S(=O)(=O)N4CCN(C)CC4)ccc3OCC)nc12 | CN1CCNCC1.C(C)OC1=C(C=C(C=C1)S(=O)(=O)Cl)C1=NC=2N(C(N1)=O)C(=NC2CCC)C>>C(C)OC1=C(C=C(C=C1)S(=O)(=O)N1CCN(CC1)C)C1=NC=2N(C(N1)=O)C(=NC2CCC)C | Cl[S:16]([c:15]1[cH:14][c:13](-[c:12]2[nH:11][c:9](=[O:10])[n:8]3[c:6]([CH3:7])[n:5][c:4]([CH2:3][CH2:2][CH3:1])[c:33]3[n:32]2)[c:28]([O:29][CH2:30][CH3:31])[cH:27][cH:26]1)(=[O:17])=[O:18].[NH:19]1[CH2:20][CH2:21][N:22]([CH3:23])[CH2:24][CH2:25]1>>[CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]([CH3:7])[n:8]2[c:9](=[O:10])[nH:1... | CCCc1nc(C)n2c(=O)[nH]c(-c3cc(S(=O)(=O)Cl)ccc3OCC)nc12.CN1CCNCC1 | CCCc1nc(C)n2c(=O)[nH]c(-c3cc(S(=O)(=O)N4CCN(C)CC4)ccc3OCC)nc12 | null | null | ClCCl | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | 8c5bae95a7afc59a07547e375f0b07a72ef45ce3f019f7996b69ec8802313118 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | O=c1[nH]c(-c2cccc(S(=O)(=O)N3CCNCC3)c2)nc2cncn12 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1)-[c:4](:[c:5]):[c:6] | null | [] | null | null | 2 | HOUR | 73 mg (0.73 mmol) of N-methylpiperazine are added to a solution of 100 mg (0.24 mmol) of 4-ethoxy-3-(6-methyl-4-oxo-8-propyl-3,4-dihydro-imidazo[1,5-a][1,3,5]triazin-2-yl)-benzenesulfonyl chloride (example VI) in 5 ml of dichloromethane and the reaction mixture is stirred at room temperature for 2 hours. After chromato... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ncn2cncc2n1.c1ccccc1.C1C[NH]CC[NH]1 | HCl | ClCCl | null | 2 | CCCc1nc(C)n2c(=O)[nH]c(-c3cc(S(=O)(=O)Cl)ccc3OCC)nc12.CN1CCNCC1>ClCCl>CCCc1nc(C)n2c(=O)[nH]c(-c3cc(S(=O)(=O)N4CCN(C)CC4)ccc3OCC)nc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1e7af79867e74406a2bab6bfb9b7df2d | CCCc1nc(C)n2c(=O)[nH]c(-c3cc(S(=O)(=O)Cl)ccc3OCC)nc12.CCN1CCNCC1>>CCCc1nc(C)n2c(=O)[nH]c(-c3cc(S(=O)(=O)N4CCN(CC)CC4)ccc3OCC)nc12 | C(C)N1CCNCC1.C(C)OC1=C(C=C(C=C1)S(=O)(=O)Cl)C1=NC=2N(C(N1)=O)C(=NC2CCC)C>>C(C)OC1=C(C=C(C=C1)S(=O)(=O)N1CCN(CC1)CC)C1=NC=2N(C(N1)=O)C(=NC2CCC)C | Cl[S:16]([c:15]1[cH:14][c:13](-[c:12]2[nH:11][c:9](=[O:10])[n:8]3[c:6]([CH3:7])[n:5][c:4]([CH2:3][CH2:2][CH3:1])[c:34]3[n:33]2)[c:29]([O:30][CH2:31][CH3:32])[cH:28][cH:27]1)(=[O:17])=[O:18].[NH:19]1[CH2:20][CH2:21][N:22]([CH2:23][CH3:24])[CH2:25][CH2:26]1>>[CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]([CH3:7])[n:8]2[c:9](=[O:1... | CCCc1nc(C)n2c(=O)[nH]c(-c3cc(S(=O)(=O)Cl)ccc3OCC)nc12.CCN1CCNCC1 | CCCc1nc(C)n2c(=O)[nH]c(-c3cc(S(=O)(=O)N4CCN(CC)CC4)ccc3OCC)nc12 | null | null | ClCCl | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | 8c5bae95a7afc59a07547e375f0b07a72ef45ce3f019f7996b69ec8802313118 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | O=c1[nH]c(-c2cccc(S(=O)(=O)N3CCNCC3)c2)nc2cncn12 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1)-[c:4](:[c:5]):[c:6] | null | [] | null | null | 2 | HOUR | 83 mg (0.73 mmol) of N-ethylpiperazine are added to a solution of 100 mg (0.24 mmol) of 4-ethoxy-3-(6-methyl-4-oxo-8-propyl-3,4-dihydro-imidazo[1,5-a]-[1,3,5]triazin-2-yl)-benzenesulfonyl chloride (example VI) in 5 ml of dichloromethane and the reaction mixture is stirred at room temperature for 2 hours. After chromato... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ncn2cncc2n1.c1ccccc1.C1C[NH]CC[NH]1 | HCl | ClCCl | null | 2 | CCCc1nc(C)n2c(=O)[nH]c(-c3cc(S(=O)(=O)Cl)ccc3OCC)nc12.CCN1CCNCC1>ClCCl>CCCc1nc(C)n2c(=O)[nH]c(-c3cc(S(=O)(=O)N4CCN(CC)CC4)ccc3OCC)nc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-936d5bb6add248b09e6db41a86e6f77c | CCCc1nc(C)n2c(=O)[nH]c(-c3cc(S(=O)(=O)Cl)ccc3OCC)nc12.CNCCc1ccc(OC)c(OC)c1>>CCCc1nc(C)n2c(=O)[nH]c(-c3cc(S(=O)(=O)N(C)CCc4ccc(OC)c(OC)c4)ccc3OCC)nc12 | COC=1C=C(C=CC1OC)CCNC.C(C)OC1=C(C=C(C=C1)S(=O)(=O)Cl)C1=NC=2N(C(N1)=O)C(=NC2CCC)C>>COC=1C=C(C=CC1OC)CCN(S(=O)(=O)C1=CC(=C(C=C1)OCC)C1=NC=2N(C(N1)=O)C(=NC2CCC)C)C | Cl[S:16]([c:15]1[cH:14][c:13](-[c:12]2[nH:11][c:9](=[O:10])[n:8]3[c:6]([CH3:7])[n:5][c:4]([CH2:3][CH2:2][CH3:1])[c:40]3[n:39]2)[c:35]([O:36][CH2:37][CH3:38])[cH:34][cH:33]1)(=[O:17])=[O:18].[NH:19]([CH3:20])[CH2:21][CH2:22][c:23]1[cH:24][cH:25][c:26]([O:27][CH3:28])[c:29]([O:30][CH3:31])[cH:32]1>>[CH3:1][CH2:2][CH2:3][... | CCCc1nc(C)n2c(=O)[nH]c(-c3cc(S(=O)(=O)Cl)ccc3OCC)nc12.CNCCc1ccc(OC)c(OC)c1 | CCCc1nc(C)n2c(=O)[nH]c(-c3cc(S(=O)(=O)N(C)CCc4ccc(OC)c(OC)c4)ccc3OCC)nc12 | null | null | ClCCl | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | abeb6d9a0c70fe5baef0a8e555c2cd55ac2317f763ce7a0831775db7a04777d8 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | O=c1[nH]c(-c2cccc(S(=O)(=O)NCCc3ccccc3)c2)nc2cncn12 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C;D1;H3:10]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[C;D1;H3:10])-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | 2 | HOUR | 143 mg (0.73 mmol) of N-(3,4-dimethoxyphenylethyl)-N-methylamine are added to a solution of 100 mg (0.24 mmol) of 4-ethoxy-3-(6-methyl-4-oxo-8-propyl-3,4-dihydro-imidazo[1,5-a][1,3,5]triazin-2-yl)-benzenesulfonyl chloride (example VI) in 5 ml of dichloromethane and the reaction mixture is stirred at room temperature fo... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | null | null | c1ncn2cncc2n1.c1ccccc1.c1ccccc1 | HCl | ClCCl | null | 2 | CCCc1nc(C)n2c(=O)[nH]c(-c3cc(S(=O)(=O)Cl)ccc3OCC)nc12.CNCCc1ccc(OC)c(OC)c1>ClCCl>CCCc1nc(C)n2c(=O)[nH]c(-c3cc(S(=O)(=O)N(C)CCc4ccc(OC)c(OC)c4)ccc3OCC)nc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0dfab5ad94fb4f82b5caaa410a7bfb95 | CCCc1nc(C)n2c(=O)[nH]c(-c3cc(S(=O)(=O)Cl)ccc3OCC)nc12.COCCN>>CCCc1nc(C)n2c(=O)[nH]c(-c3cc(S(=O)(=O)NCCOC)ccc3OCC)nc12 | COCCN.C(C)OC1=C(C=C(C=C1)S(=O)(=O)Cl)C1=NC=2N(C(N1)=O)C(=NC2CCC)C>>C(C)OC1=C(C=C(C=C1)S(=O)(=O)NCCOC)C1=NC=2N(C(N1)=O)C(=NC2CCC)C | Cl[S:16]([c:15]1[cH:14][c:13](-[c:12]2[nH:11][c:9](=[O:10])[n:8]3[c:6]([CH3:7])[n:5][c:4]([CH2:3][CH2:2][CH3:1])[c:31]3[n:30]2)[c:26]([O:27][CH2:28][CH3:29])[cH:25][cH:24]1)(=[O:17])=[O:18].[NH2:19][CH2:20][CH2:21][O:22][CH3:23]>>[CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]([CH3:7])[n:8]2[c:9](=[O:10])[nH:11][c:12](-[c:13]3[c... | CCCc1nc(C)n2c(=O)[nH]c(-c3cc(S(=O)(=O)Cl)ccc3OCC)nc12.COCCN | CCCc1nc(C)n2c(=O)[nH]c(-c3cc(S(=O)(=O)NCCOC)ccc3OCC)nc12 | null | null | ClCCl | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=c1[nH]c(-c2ccccc2)nc2cncn12 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | 2 | HOUR | 55 mg (0.73 mmol) of 2-methoxyethylamine are added to a solution of 100 mg (0.24 mmol) of 4-ethoxy-3-(6-methyl-4-oxo-8-propyl-3,4-dihydro-imidazo[1,5-a][1,3,5]triazin-2-yl)-benzenesulfonyl chloride (example VI) in 5 ml of dichloromethane and the reaction mixture is stirred at room temperature for 2 hours. After chromat... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ncn2cncc2n1.c1ccccc1 | HCl | ClCCl | null | 2 | CCCc1nc(C)n2c(=O)[nH]c(-c3cc(S(=O)(=O)Cl)ccc3OCC)nc12.COCCN>ClCCl>CCCc1nc(C)n2c(=O)[nH]c(-c3cc(S(=O)(=O)NCCOC)ccc3OCC)nc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3576d222a16847d3975b9255760ce381 | CCCc1nc(C)n2c(=O)[nH]c(-c3cc(S(=O)(=O)Cl)ccc3OCC)nc12.OC1CCNCC1>>CCCc1nc(C)n2c(=O)[nH]c(-c3cc(S(=O)(=O)N4CCC(O)CC4)ccc3OCC)nc12 | OC1CCNCC1.C(C)OC1=C(C=C(C=C1)S(=O)(=O)Cl)C1=NC=2N(C(N1)=O)C(=NC2CCC)C>>C(C)OC1=C(C=C(C=C1)S(=O)(=O)N1CCC(CC1)O)C1=NC=2N(C(N1)=O)C(=NC2CCC)C | Cl[S:16]([c:15]1[cH:14][c:13](-[c:12]2[nH:11][c:9](=[O:10])[n:8]3[c:6]([CH3:7])[n:5][c:4]([CH2:3][CH2:2][CH3:1])[c:33]3[n:32]2)[c:28]([O:29][CH2:30][CH3:31])[cH:27][cH:26]1)(=[O:17])=[O:18].[NH:19]1[CH2:20][CH2:21][CH:22]([OH:23])[CH2:24][CH2:25]1>>[CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]([CH3:7])[n:8]2[c:9](=[O:10])[nH:1... | CCCc1nc(C)n2c(=O)[nH]c(-c3cc(S(=O)(=O)Cl)ccc3OCC)nc12.OC1CCNCC1 | CCCc1nc(C)n2c(=O)[nH]c(-c3cc(S(=O)(=O)N4CCC(O)CC4)ccc3OCC)nc12 | null | null | ClCCl | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | d63e07b47df62aebedb35134f6d0504cfcbed5ccfdec31c2c42bba6875c15fe7 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | O=c1[nH]c(-c2cccc(S(=O)(=O)N3CCCCC3)c2)nc2cncn12 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6])-[C:10]-[C:11] | null | [] | null | null | 2 | HOUR | 74 mg (0.73 mmol) of 4-hydroxylpiperidine are added to a solution of 100 mg (0.24 mmol) of 4-ethoxy-3-(6-methyl-4-oxo-8-propyl-3,4-dihydro-imidazo[1,5-a][1,3,5]triazin-2-yl)-benzenesulfonyl chloride (example VI) in 5 ml of dichloromethane and the reaction mixture is stirred at room temperature for 2 hours. After chroma... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ncn2cncc2n1.c1ccccc1.C1CC[NH]CC1 | HCl | ClCCl | null | 2 | CCCc1nc(C)n2c(=O)[nH]c(-c3cc(S(=O)(=O)Cl)ccc3OCC)nc12.OC1CCNCC1>ClCCl>CCCc1nc(C)n2c(=O)[nH]c(-c3cc(S(=O)(=O)N4CCC(O)CC4)ccc3OCC)nc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9fdbebea0cd2417a98d35f38d61d0e08 | COc1cc([N+](=O)[O-])ccc1Cl>>O=[N+]([O-])c1ccc(Cl)c(O)c1 | ClC1=C(C=C(C=C1)[N+](=O)[O-])OC>>ClC1=C(C=C(C=C1)[N+](=O)[O-])O | C[O:10][c:9]1[c:7]([Cl:8])[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:11]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([Cl:8])[c:9]([OH:10])[cH:11]1 | COc1cc([N+](=O)[O-])ccc1Cl | O=[N+]([O-])c1ccc(Cl)c(O)c1 | null | null | Br.CC(=O)O | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 3 | HOUR | 2-Chloro-5-nitroanisole (310 g, 1.7 mol) was taken up in a mixture of 48% HBr (1.5 L) and AcOH (1.2 L) and heated at reflux for 3 days. The dark solution was allowed to cool to room temperature, poured into ice water (10 L), and let stand for 3 h. The resultant dull yellow solid was filtered, washed with water, and dri... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1 | Other | Br.CC(=O)O | null | 3 | COc1cc([N+](=O)[O-])ccc1Cl>Br.CC(=O)O>O=[N+]([O-])c1ccc(Cl)c(O)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-03a6ba3e17a44728844857814bf2bd02 | O=[N+]([O-])c1ccc(Cl)c(O)c1>>Nc1ccc(Cl)c(O)c1 | ClC1=C(C=C(C=C1)[N+](=O)[O-])O>>ClC1=C(C=C(C=C1)N)O | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([Cl:6])[c:7]([OH:8])[cH:9]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([Cl:6])[c:7]([OH:8])[cH:9]1 | O=[N+]([O-])c1ccc(Cl)c(O)c1 | Nc1ccc(Cl)c(O)c1 | null | [Pt] | 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]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 6 | HOUR | A solution of 2-chloro-5-nitrophenol (114 g, 0.66 mol) in ethyl acetate (500 mL) was treated with 5% Pt/C (510 mg, 0.5 weight %) and the mixture shaken under a hydrogen atmosphere (30 psi) for 6 h. The mixture was filtered through Celite® and the residue washed well with ethyl acetate. Evaporation of the ethyl acetate ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Pt].C(C)(=O)OCC | null | 6 | O=[N+]([O-])c1ccc(Cl)c(O)c1>[Pt].C(C)(=O)OCC>Nc1ccc(Cl)c(O)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ccbe68207e224ea698fc109773a904a3 | CC(C)(C)OC(=O)Nc1ccc(Cl)c(O)c1.CN1CC[C@H](O)C1>>CN1CC[C@@H](Oc2cc(N)ccc2Cl)C1 | CC(C)OC(=O)/N=N/C(=O)OC(C)C.C(C)(C)(C)OC(NC1=CC(=C(C=C1)Cl)O)=O.CN1C[C@H](CC1)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>ClC1=C(C=C(N)C=C1)O[C@H]1CN(CC1)C | CC(C)(C)OC(=O)[NH:10][c:9]1[cH:8][c:7]([OH:6])[c:13]([Cl:14])[cH:12][cH:11]1.O[C@H:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:15]1>>[CH3:1][N:2]1[CH2:3][CH2:4][C@@H:5]([O:6][c:7]2[cH:8][c:9]([NH2:10])[cH:11][cH:12][c:13]2[Cl:14])[CH2:15]1 | CC(C)(C)OC(=O)Nc1ccc(Cl)c(O)c1.CN1CC[C@H](O)C1 | CN1CC[C@@H](Oc2cc(N)ccc2Cl)C1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 1c4f78464edae36f36cc21af01f1a35b2b61bd1b4381e8d8731e49ab2651a18e | 8a76680998597d1b44abd3611e7dd1de349d47cee3c268c5d1e953d495442aac | c1ccc(O[C@@H]2CCNC2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5](-[OH;D1;+0:6]):[c:7].O-[C@@H;D3;+0:8]1-[C:9]-[#7:10](-[C;D1;H3:11])-[C:12]-[C:13]-1>>[C;D1;H3:11]-[#7:10]1-[C:9]-[C@H;D3;+0:8](-[O;H0;D2;+0:6]-[c:5](:[c:7]):[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3])-[C:13]-[C:12]-1 | 80 | [{"value": 80.0, "product": "ClC1=C(C=C(N)C=C1)O[C@H]1CN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.7, "product": "ClC1=C(C=C(N)C=C1)O[C@H]1CN(CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | To a cooled (0° C.) solution of 4-chloro-3-hydroxyphenylcarbamic acid tert-butyl ester (55 g, 0.23 mol), (S)-1-methyl-pyrrolidin-3-ol (24 g, 0.24 mol), and triphenylphosphine (89 g, 0.34 mol) in THF (1.1 L) was added dropwise via addition funnel a solution of DIAD (67 mL, 0.34 mol) in THF (100 mL) over 1 h. The resulta... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Secondary alcohol.Aromatic alcohol.Boc | Ether.Primary amine | C1CC[NH]C1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccccc1 | HO- | C1CCOC1 | null | 4 | CC(C)(C)OC(=O)Nc1ccc(Cl)c(O)c1.CN1CC[C@H](O)C1>C1CCOC1>CN1CC[C@@H](Oc2cc(N)ccc2Cl)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2f30ba84e4194cd6b9cb4784c4f11ab7 | O=S(=O)(Cl)c1cc(Cl)sc1Cl>>O=S(=O)(Cl)c1c(Cl)sc(Cl)c1Cl | ClC=1SC(=CC1S(=O)(=O)Cl)Cl.[S]Cl.O>>ClC=1SC(=C(C1S(=O)(=O)Cl)Cl)Cl | [O:1]=[S:2](=[O:3])([Cl:4])[c:5]1[c:6]([Cl:7])[s:8][c:9]([Cl:10])[cH:11]1>>[O:1]=[S:2](=[O:3])([Cl:4])[c:5]1[c:6]([Cl:7])[s:8][c:9]([Cl:10])[c:11]1[Cl:12] | O=S(=O)(Cl)c1cc(Cl)sc1Cl | O=S(=O)(Cl)c1c(Cl)sc(Cl)c1Cl | null | [Cl-].[Cl-].[Cl-].[Al+3] | S(=O)(=O)(Cl)Cl | Functional Group Addition | Aromatic chlorination | 88b0b5b06f95ec554e4957a444dff536f4d3c982d2ea1fdc7e4f9fc090256342 | 0a2f22058f27970cef4a98a778644dbe9c44e91f66c74cd24db321993177608a | c1ccsc1 | [#16:1]-[c:2]1:[cH;D2;+0:3]:[c:4](-[Cl;D1;H0:5]):[#16;a:6]:[c:7]:1-[Cl;D1;H0:8]>>[#16:1]-[c:2]1:[c:7](-[Cl;D1;H0:8]):[#16;a:6]:[c:4](-[Cl;D1;H0:5]):[c;H0;D3;+0:3]:1-[Cl;D1;H0:9] | 991.6 | [{"value": 33.0, "product": "ClC=1SC(=C(C1S(=O)(=O)Cl)Cl)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 991.6, "product": "ClC=1SC(=C(C1S(=O)(=O)Cl)Cl)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | A mixture of 2,5-dichlorothiophene-3-sulfonyl chloride (1.2 g, 5 mmol) and sulfur monochloride (10 mg) in sulfuryl chloride (500 mg) was heated at 60° C. for 30 min, at which time was added dropwise a mixture of aluminum trichloride (10 mg) in sulfuryl chloride (500 mg). The reaction was heated at 60° C. for an additio... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccsc1 | c1ccsc1 | c1ccsc1 | Other | [Cl-].[Cl-].[Cl-].[Al+3].S(=O)(=O)(Cl)Cl | 60 | null | O=S(=O)(Cl)c1cc(Cl)sc1Cl>[Cl-].[Cl-].[Cl-].[Al+3].S(=O)(=O)(Cl)Cl>O=S(=O)(Cl)c1c(Cl)sc(Cl)c1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d3a94c6cd2a949a99cb74eb9ff971a3b | Cc1ccsc1.O=S(=O)(Cl)Cl.O=S(=O)(O)Cl>>Cc1c(Cl)sc(Cl)c1S(=O)(=O)Cl | CC1=CSC=C1.ClCCl.S(=O)(=O)(Cl)Cl.ClCCl.ClS(=O)(=O)O>>ClC=1SC(=C(C1S(=O)(=O)Cl)C)Cl | [CH3:1][c:2]1[cH:3][s:5][cH:6][cH:8]1.O=S(=O)([Cl:4])[Cl:7].O=[S:9]([OH:10])(=[O:11])[Cl:12]>>[CH3:1][c:2]1[c:3]([Cl:4])[s:5][c:6]([Cl:7])[c:8]1[S:9](=[O:10])(=[O:11])[Cl:12] | Cc1ccsc1.O=S(=O)(Cl)Cl.O=S(=O)(O)Cl | Cc1c(Cl)sc(Cl)c1S(=O)(=O)Cl | null | null | null | Protection | OtherReaction | 88fc2805172902e489e60e440c3c497d599837486da34ea8cbac0db27b64a0fa | 25e7350e36d768e0ac1e09821f7d8a1f3272be61afb3f9fe971c2cbad91885f2 | c1ccsc1 | O=S(=O)(-[Cl;H0;D1;+0:1])-[Cl;H0;D1;+0:2].O=[S;H0;D4;+0:3](-[Cl;D1;H0:4])(=[O;D1;H0:5])-[OH;D1;+0:6].[C;D1;H3:7]-[c:8]1:[cH;D2;+0:9]:[#16;a:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:1>>[C;D1;H3:7]-[c:8]1:[c;H0;D3;+0:9](-[Cl;H0;D1;+0:1]):[#16;a:10]:[c;H0;D3;+0:11](-[Cl;H0;D1;+0:2]):[c;H0;D3;+0:12]:1-[S;H0;D4;+0:3](-[Cl;D1;H0:4])(... | 25 | [{"value": 25.0, "product": "ClC=1SC(=C(C1S(=O)(=O)Cl)C)Cl", "details": "PERCENTYIELD", "is_desired": false}] | 10 | CELSIUS | 16 | HOUR | To a cooled (10° C.) solution of 3-methylthiophene (5 g, 50 mmol) in dichloromethane (15 mL) was added a solution of sulfuryl chloride (8.6 mL) in dichloromethane (5 mL). The reaction mixture was maintained at 10° C. for 30 minutes, then at ambient temperature for 16 hours. The reaction was concentrated and redissolved... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide.Aromatic halide.Sulfonyl halide | c1ccsc1 | c1ccsc1 | c1ccsc1 | HO- | null | 10 | 16 | Cc1ccsc1.O=S(=O)(Cl)Cl.O=S(=O)(O)Cl>>Cc1c(Cl)sc(Cl)c1S(=O)(=O)Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-faf8ea38427d47c980c4409fde19d250 | CN1CC[C@@H](O)C1.O=[N+]([O-])c1ccc(C(F)(F)F)c(F)c1>>CN1CC[C@@H](Oc2cc([N+](=O)[O-])ccc2C(F)(F)F)C1 | FC1=C(C=CC(=C1)[N+](=O)[O-])C(F)(F)F.CN1C[C@@H](CC1)O.[H-].[Na+]>>CN1C[C@@H](CC1)OC1=C(C=CC(=C1)[N+](=O)[O-])C(F)(F)F | [CH3:1][N:2]1[CH2:3][CH2:4][C@@H:5]([OH:6])[CH2:20]1.F[c:7]1[cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13][cH:14][c:15]1[C:16]([F:17])([F:18])[F:19]>>[CH3:1][N:2]1[CH2:3][CH2:4][C@@H:5]([O:6][c:7]2[cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13][cH:14][c:15]2[C:16]([F:17])([F:18])[F:19])[CH2:20]1 | CN1CC[C@@H](O)C1.O=[N+]([O-])c1ccc(C(F)(F)F)c(F)c1 | CN1CC[C@@H](Oc2cc([N+](=O)[O-])ccc2C(F)(F)F)C1 | null | null | CO.CCOC(=O)C.O1CCCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | fc6e1b465ae75176f3fa192a660d0d622bdf538cea285b0e2b9dc00b273004b2 | 1f70dbbaebc288b3a5d3f37803812d9d22b151831cd4b8351080508554b19875 | c1ccc(O[C@@H]2CCNC2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8]):[c:9].[#7:10]-[C:11]-[C:12](-[OH;D1;+0:13])-[C:14]>>[#7:10]-[C:11]-[C:12](-[O;H0;D2;+0:13]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8]):[c:9])-[C:14] | 46 | [{"value": 46.0, "product": "CN1C[C@@H](CC1)OC1=C(C=CC(=C1)[N+](=O)[O-])C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.6, "product": "CN1C[C@@H](CC1)OC1=C(C=CC(=C1)[N+](=O)[O-])C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | A solution of 2-fluoro-4-nitrobenzotrifluoride (12.4 g, 59.3 mmol, 1.0 eq) and (R)-1-methyl-pyrrolidin-3-ol (6.0 g, 59.3 mmol, 1.0 eq) in anhydrous tetrahydrofuran (150 ml) was cooled to 0° C. then slowly treated with portions of 60% sodium hydride (4.7 g, 0.12 mol, 2 eq) over 5 min. Without removing the ice bath, the ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary alcohol | Ether | c1ccccc1 | c1ccccc1 | C1CC[NH]C1.c1ccccc1 | HF | CO.CCOC(=O)C.O1CCCC1 | null | 48 | CN1CC[C@@H](O)C1.O=[N+]([O-])c1ccc(C(F)(F)F)c(F)c1>CO.CCOC(=O)C.O1CCCC1>CN1CC[C@@H](Oc2cc([N+](=O)[O-])ccc2C(F)(F)F)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6bc67ca7fb6f48d4b4d2e9c4d8a61c2c | CN1CC[C@@H](Oc2cc([N+](=O)[O-])ccc2C(F)(F)F)C1>>CN1CC[C@@H](Oc2cc(N)ccc2C(F)(F)F)C1 | CN1C[C@@H](CC1)OC1=C(C=CC(=C1)[N+](=O)[O-])C(F)(F)F.[H][H].S(=O)(=O)([O-])[O-].[Mg+2]>>CN1C[C@@H](CC1)OC=1C=C(C=CC1C(F)(F)F)N | O=[N+:10]([O-])[c:9]1[cH:8][c:7]([O:6][C@@H:5]2[CH2:4][CH2:3][N:2]([CH3:1])[CH2:18]2)[c:13]([C:14]([F:15])([F:16])[F:17])[cH:12][cH:11]1>>[CH3:1][N:2]1[CH2:3][CH2:4][C@@H:5]([O:6][c:7]2[cH:8][c:9]([NH2:10])[cH:11][cH:12][c:13]2[C:14]([F:15])([F:16])[F:17])[CH2:18]1 | CN1CC[C@@H](Oc2cc([N+](=O)[O-])ccc2C(F)(F)F)C1 | CN1CC[C@@H](Oc2cc(N)ccc2C(F)(F)F)C1 | null | [Pt] | C(C)(=O)OCC | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(O[C@@H]2CCNC2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | A solution of 2-((R)-1-Methyl-pyrrolidin-3-yloxy)-4-nitrobenzotrifluoride (7.8 g, 26.9 mmol) in ethyl acetate (50 ml) was treated with 10% platinum on carbon (200 mg) then subjected to 40 psi hydrogen pressure for 3 hrs. The slurry was treated with anhydrous magnesium sulfate (5 g) then filtered through a pad of Celite... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | C1CC[NH]C1.c1ccccc1 | Other | [Pt].C(C)(=O)OCC | null | null | CN1CC[C@@H](Oc2cc([N+](=O)[O-])ccc2C(F)(F)F)C1>[Pt].C(C)(=O)OCC>CN1CC[C@@H](Oc2cc(N)ccc2C(F)(F)F)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-581af56aec3a433e9adb69447c08ffc7 | BrCCBr.NCc1cccc(F)c1>>Fc1cccc(CNCCBr)c1 | C([O-])([O-])=O.[Na+].[Na+].FC=1C=C(CN)C=CC1.BrCCBr>>BrCCNCC1=CC(=CC=C1)F | Br[CH2:9][CH2:10][Br:11].[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][NH2:8])[cH:12]1>>[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][NH:8][CH2:9][CH2:10][Br:11])[cH:12]1 | BrCCBr.NCc1cccc(F)c1 | Fc1cccc(CNCCBr)c1 | null | null | O | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[Br;D1;H0:3].[NH2;D1;+0:4]-[C:5]-[c:6]>>[Br;D1;H0:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[C:5]-[c:6] | null | [] | null | null | null | null | Combine 3-fluorobenzylamine (5.0 g, 0.0400 mol), fused sodium acetate (3.28 g, 0.0400 mol) and 1,2-dibromoethane (7.51 g, 0.0400 mol) and reflux for several hours. Pour the mixture into water and add sodium carbonate to create a basic pH. Remove the unreacted 1,2-dibromoethane by distillation. Extract the left-over res... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1 | HBr | O | null | null | BrCCBr.NCc1cccc(F)c1>O>Fc1cccc(CNCCBr)c1 |
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