original_index int64 2 1.77M | extracted_from_file stringclasses 489
values | date_of_experiment timestamp[ns]date | grant_date timestamp[ns]date 1976-01-01 00:01:00 2016-01-01 00:09:00 | is_mapped bool 1
class | rxn_str stringlengths 87 6.12k | reactant_000 stringlengths 1 902 | reactant_001 stringlengths 1 902 ⌀ | reactant_002 null | agent_000 stringlengths 1 540 ⌀ | agent_001 stringlengths 1 852 ⌀ | agent_002 stringlengths 1 247 ⌀ | agent_003 null | agent_004 null | agent_005 null | agent_006 null | agent_007 null | agent_008 null | agent_009 null | agent_010 null | agent_011 null | agent_012 null | agent_013 null | agent_014 null | agent_015 null | agent_016 null | solvent_000 stringclasses 446
values | solvent_001 stringclasses 405
values | solvent_002 null | solvent_003 null | solvent_004 null | solvent_005 null | solvent_006 null | solvent_007 null | solvent_008 null | solvent_009 null | solvent_010 null | temperature float64 -230 30.1k ⌀ | rxn_time float64 0 2.16k ⌀ | procedure_details stringlengths 8 24.5k | product_000 stringlengths 1 484 | product_001 null | yield_000 float64 0 90,205,156,600B ⌀ | yield_001 float64 0 100M ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
1,579,767 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | CC(O)=O.[NH2:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[C:11]([CH3:16])[C:10]([C:17]([O:19][CH3:20])=[O:18])=[C:9]2[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[CH2:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:29][C:28]1=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[CH2:27]1[C:35]2[C:30](=[CH:3... | COC(=O)c1c(C)nc2ccc(N)cc2c1-c1ccccc1 | O=C1Cc2ccccc2C1 | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | ClCCCl | null | null | null | null | null | null | null | null | null | 25 | 8 | A method of Abdel-Magid et al (J. Org. Chem., 61, 3849, 1996) was used: Glacial AcOH (0.2 ml) was added to a solution of the product of Step 2 (0.91 g, 3.31 mmol), 1H-inden-2(3H)-one (0.41 g, 3.31 mmol) and NaBH(OAc)3 (1.05 g, 4.9 mmol) in anhydrous 1,2-dichloroethane (12.5 ml). The resulting mixture was stirred overni... | COC(=O)c1c(C)nc2ccc(NC3Cc4ccccc4C3)cc2c1-c1ccccc1 | null | 72.5 | null |
341,143 | ord_dataset-4706e7a7f3cd421bb42b7f877cff8af9 | null | 1996-01-01T00:09:00 | true | [CH3:1][C:2]1([CH3:16])[C:11]2[C:6](=[C:7]([CH3:13])[CH:8]=[C:9]([CH3:12])[CH:10]=2)[C:5]([CH3:15])([CH3:14])[CH2:4][CH2:3]1.[CH:17]([O:20]C)(Cl)Cl>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[CH3:13][C:7]1[C:6]2[C:5]([CH3:15])([CH3:14])[CH2:4][CH2:3][C:2]([CH3:16])([CH3:1])[C:11]=2[CH:10]=[C:9]([CH3:12])[C:8]=1[CH:17]=[O:20] | COC(Cl)Cl | Cc1cc(C)c2c(c1)C(C)(C)CCC2(C)C | null | Cl[Ti](Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 1,2,3,4-tetrahydro-1,1,4,4,5,7-hexamethylnaphthalene (5.0 g) of TiCl4 (7.32 g) in methylene chloride (40 ml) was treated with Cl2CHOCH3 (2.66 g) in methylene chloride (5 ml), at 0° and over 20 min. The temperature of the reaction mixture was allowed to reach 20° (20 min) and said mixture was then poured on... | Cc1cc2c(c(C)c1C=O)C(C)(C)CCC2(C)C | null | 71.9 | null |
1,590,332 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [N:1]1[C:6]2[NH:7][CH:8]=[CH:9][C:5]=2[C:4]([N:10]2[CH2:15][CH2:14][CH:13]([NH2:16])[CH2:12][CH2:11]2)=[N:3][CH:2]=1.[N:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23](O)=[O:24])[CH:18]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C>[NH:1]1[C:6]2=[N:7][CH:8]=[CH:9][C:5]2... | NC1CCN(c2ncnc3[nH]ccc23)CC1 | O=C(O)c1cccnc1 | null | CN(C)C(On1nnc2cccnc21)=[N+](C)C | F[P-](F)(F)(F)(F)F | On1nnc2cccnc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 2 | To a mixture of 1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-4-piperidinamine D2 (100 mg), 3-pyridinecarboxylic acid (56.7 mg, 0.460 mmol), HATU (210 mg, 0.552 mmol) and HOAt (37.60 mg, 0.276 mmol) in DMF (2.3 mL) was added DIPEA (386 μL, 2.209 mmol). The reaction mixture was stirred at room temperature for 2 hours then the sol... | O=C(NC1CCN(c2nc[nH]c3nccc2-3)CC1)c1cccnc1 | null | null | null |
184,320 | ord_dataset-8537fa92abf34c849134600c0c2bbcc7 | null | 1989-01-01T00:02:00 | true | [N+:1]([C:4]1[CH:58]=[CH:57][C:7]([O:8][P:9]2([O:47][C:48]3[CH:53]=[CH:52][C:51]([N+:54]([O-])=O)=[CH:50][CH:49]=3)[N:14]=[P:13]([O:25][C:26]3[CH:31]=[CH:30][C:29]([N+:32]([O-])=O)=[CH:28][CH:27]=3)([O:15][C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=3)[N:12]=[P:11]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][... | [H][H] | O=[N+]([O-])c1ccc(OP2(Oc3ccc([N+](=O)[O-])cc3)=NP(Oc3ccc([N+](=O)[O-])cc3)(Oc3ccc([N+](=O)[O-])cc3)=NP(c3ccccc3)(c3ccccc3)=N2)cc1 | null | O=[Pt] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Nc1ccccc1 | C1CCCCC1 | null | null | null | null | null | null | null | null | null | null | null | 2,2,4,4-Tetra(p-nitrophenoxy)-6,6-diphenylcyclotriphosphazene (16.01 g, 0.021 moles), platinum oxide catalyst (0.09 g, 0.0004 moles), and 50 mls aniline are added to a 500 ml Fischer-Porter reaction vessel. The reaction is heated to 50° C. at 50-60 psi of hydrogen pressure for 65 hours. The reaction mixture is then coo... | Nc1ccc(OP2(Oc3ccc(N)cc3)=NP(Oc3ccc(N)cc3)(Oc3ccc(N)cc3)=NP(c3ccccc3)(c3ccccc3)=N2)cc1 | null | 78 | null |
1,449,239 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [CH3:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[C:10]1[CH:18]=[C:17]2[C:13]([C:14]3([CH2:23][CH2:22][CH2:21][CH2:20]3)[C:15](=[O:19])[NH:16]2)=[CH:12][CH:11]=1.[NH2:24][OH:25].C([O-])(=O)C.[Na+]>C(O)C.O>[OH:25]/[N:24]=[C:6](/[NH2:7])\[C:5]1[CH:8]=[CH:9][C:2]([CH3:1])=[C:3]([C:10]2[CH:18]=[C:17]3[C:13]([C:14]... | Cc1ccc(C#N)cc1-c1ccc2c(c1)NC(=O)C21CCCC1 | NO | null | CC(=O)[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | O | null | null | null | null | null | null | null | null | null | 85 | 6 | A stirred mixture of 4-methyl-3-(2′-oxospiro[cyclopentane-1,3′-indoline]-6′-yl)benzonitrile (preparation 54b, 0.06 g, 0.20 mmol), hydroxylamine (0.02 g, 0.24 mmol) and sodium acetate (0.02 g, 0.27 mmol) in ethanol (0.60 mL) and water (0.10 mL) were heated to 85° C. in a sealed tube. After 6 hours, the mixture was coole... | Cc1ccc(/C(N)=N\O)cc1-c1ccc2c(c1)NC(=O)C21CCCC1 | null | 89.4 | null |
611,745 | ord_dataset-5c4ee54447b84205a10f9c0473172972 | null | 2003-01-01T00:10:00 | true | Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[OH:8][C:9]1[CH:10]=[C:11]([CH:14]=[C:15]([OH:18])[C:16]=1[OH:17])[CH:12]=[O:13]>>[CH2:2]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[C:15]([O:18][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[C:16]=1[O:17][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[CH:12]=[O:13])[CH2:3][CH2:4][CH2:5][C... | O=Cc1cc(O)c(O)c(O)c1 | CCCCCCBr | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared according to the method described in Example 9 above from 1-bromohexan and 3,4,5-trihydroxy-benzaldehyde. | CCCCCCOc1cc(C=O)cc(OCCCCCC)c1OCCCCCC | null | null | null |
1,451,255 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [C-:1]#[N:2].[K+].Cl[CH2:5][C:6]1[N:7]=[C:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:9][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O>CS(C)=O>[C:17]1([C:8]2[O:9][C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:6]([CH2:5][C:1]#[N:2])[N:7]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1 | [C-]#N | ClCc1nc(-c2ccccc2)oc1-c1ccccc1 | null | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | O | null | null | null | null | null | null | null | null | null | 45 | 3 | To a suspension of potassium cyanide (67.1 mg, 0.999 mmol) in DMSO (2 mL) was added dropwise at RT a solution of 4-(chloromethyl)-2,5-diphenyloxazole (245 mg, 908 μmol) in DMSO (3 mL) over a period of 5 min. The reaction mixture was stirred at RT for 2 h and at 45° C. for another 3 h. The reaction mixture was cooled to... | N#CCc1nc(-c2ccccc2)oc1-c1ccccc1 | null | 103.7 | null |
1,073,879 | ord_dataset-5df93261afc143c3ae919a57ff4fc1d4 | null | 2011-01-01T00:07:00 | true | [Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11](=O)[CH3:12])=[CH:4][CH:3]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>>[Br:1][C:2]1[CH:7]=[C:6]2[C:5]([CH2:8][CH2:9][N:10]=[C:11]2[CH3:12])=[CH:4][CH:3]=1 | CC(=O)NCCc1ccc(Br)cc1 | null | null | O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | In close analogy to the procedure described above, N-[2-(4-bromo-phenyl)-ethyl]-acetamide is reacted with phosphorus pentoxide to provide the title compound. | CC1=NCCc2ccc(Br)cc21 | null | null | null |
1,493,988 | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | null | 2014-01-01T00:10:00 | true | [Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([CH2:9][CH2:10][C:11]([OH:13])=O)=[C:4]([F:14])[CH:3]=1.O=S(Cl)Cl.[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[Br:1][C:2]1[C:7]([F:8])=[C:6]2[C:5]([CH2:9][CH2:10][C:11]2=[O:13])=[C:4]([F:14])[CH:3]=1 | O=C(O)CCc1cc(F)c(Br)cc1F | null | null | [Al+3] | [Cl-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=S(Cl)Cl | null | null | null | null | null | null | null | null | null | 25 | 18 | To a solution of 3-(4-bromo-2,5-difluorophenyl)propanoic acid (1.10 g) in DCM (20 mL) was added SOCl2 (2.45 g). The mixture was stirred at room temperature for 18 hours. The solvent was removed by evaporation under reduced pressure. The residue was dried under high vacuum to give a crude solid. To the residue was added... | O=C1CCc2c(F)cc(Br)c(F)c21 | null | null | null |
1,660,893 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [NH:1]1[CH2:5][CH2:4][C@H:3]([OH:6])[CH2:2]1.Br[C:8]1[CH:9]=[N:10][C:11]([N:14]2[CH2:19][CH2:18][CH:17]([C:20]3[C:29]([CH:30]([F:41])[C:31]4[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][CH:32]=4)=[C:28]([CH:42]4[CH2:47][CH2:46][C:45]([F:49])([F:48])[CH2:44][CH2:43]4)[C:27]4[CH:26]([O:50]CC5C=CC(OC)=CC=5)[... | COc1ccc(COC2CC(C)(C)Cc3nc(C4CCN(c5ncc(Br)cn5)CC4)c(C(F)c4ccc(C(F)(F)F)cc4)c(C4CCC(F)(F)CC4)c32)cc1 | O[C@H]1CCNC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Reactions similar to those of Reference Example 13 were performed except for using (3S)-3-pyrrolidinol instead of isonipecotic acid ethyl ester, and from 100 mg (0.120 mmol) of (−)-2-[1-(5-Bromopyrimidin-2-yl)piperidin-4-yl]-4-(4,4-difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-5-[(4-methoxybenzyl)oxy]... | CC1(C)Cc2nc(C3CCN(c4ncc(N5CC[C@H](O)C5)cn4)CC3)c(C(F)c3ccc(C(F)(F)F)cc3)c(C3CCC(F)(F)CC3)c2C(O)C1 | null | null | null |
500,764 | ord_dataset-18e9ed24dbd44e98b33bdc22aa7580a8 | null | 2001-01-01T00:04:00 | true | [C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COCCN(S(F)(F)[F:20])CCOC>C(Cl)Cl>[C:1]([F:20])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1 | O=C(Cl)c1ccccc1 | COCCN(CCOC)S(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 16 | A solution of benzoyl chloride (141 mg, 1 mmol) in CH2Cl2 (5.0 mL) was added to bis(methoxyethyl)aminosulfur trifluoride (567 mg, 3.0 mmol ) under N2 and stirred for 16 h at room temperature. After work-up as above benzoyl fluoride (124 mg, quantitative yield) was obtained. The product was identified by g.c.m.s. M+=124 | O=C(F)c1ccccc1 | null | 99.9 | null |
435,382 | ord_dataset-386da077ab2340638cada986e2ef0770 | null | 1999-01-01T00:07:00 | true | [C:1]1([C:7]2[NH:8][C:9](=[O:24])[N:10]([S:12]([C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[NH:20][CH2:19][CH2:18]4)(=[O:14])=[O:13])[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[CH2:31]([O:33][C:34](Cl)=[O:35])[CH3:32]>ClCCl>[C:1]1([C:7]2[NH:8][C:9](=[O:24])[N:10]([S:12]([C:15]3[CH:16]=[C:17]4[C:21](=[C... | O=c1[nH]c(-c2ccccc2)cn1S(=O)(=O)c1ccc2c(c1)CCN2 | CCOC(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | c1ccncc1 | null | null | null | null | null | null | null | null | null | 25 | 1 | 4-Phenyl-1-(indoline-5-sulfonyl)-2-imidazolone (150 mg, 0.44 mmol) prepared in Preparation 3 was dissolved in 10 m of dichloromethane and then pyridine (39 μ, 0.484 mmol) and ethylchloroformate (46 μ, 0.484 mmol) were added thereto one after another. After the reaction mixture was stirred for one hour at room temperatu... | CCOC(=O)N1CCc2cc(S(=O)(=O)n3cc(-c4ccccc4)[nH]c3=O)ccc21 | null | 95.1 | null |
1,074,077 | ord_dataset-5df93261afc143c3ae919a57ff4fc1d4 | null | 2011-01-01T00:07:00 | true | [Br:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[C:9]([C:11]([OH:13])=O)[CH:10]=2)[CH:7]=1.[CH3:14][O:15][C:16]1[N:21]=[C:20]([O:22][CH3:23])[C:19]([C:24]2[CH:25]=[C:26]3[C:31](=[CH:32][CH:33]=2)[CH:30]([CH3:34])[NH:29][CH2:28][CH2:27]3)=[CH:18][N:17]=1>>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[C:9]([C:11]([N:29]3[CH2:28][... | COc1ncc(-c2ccc3c(c2)CCNC3C)c(OC)n1 | O=C(O)c1cc2ncc(Br)cn2n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | In close analogy to the procedure described in Example 1, 6-bromo-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid is reacted with 6-(2,4-Dimethoxy-pyrimidin-5-yl)-1-methyl-1,2,3,4-tetrahydro-isoquinoline to provide the title compound in moderate yield. | COc1ncc(-c2ccc3c(c2)CCN(C(=O)c2cc4ncc(Br)cn4n2)C3C)c(OC)n1 | null | null | null |
1,639,484 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | C(N(CC)CC)C.Cl.Cl.[C:10]([O:13][CH2:14][C@@H:15]1[C@@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@H:19]([O:25][C:26](=[O:28])[CH3:27])[C@@H:18]([O:29][C:30](=[O:32])[CH3:31])[C@H:17]([N:33]2[C:41]3[C:36](=[C:37]([CH3:42])[CH:38]=[CH:39][CH:40]=3)[C:35]([CH2:43][C:44]3[CH:49]=[CH:48][C:47](/[CH:50]=[CH:51]/[CH2:52][CH2:53][N:... | CC(=O)OC[C@H]1O[C@@H](n2cc(Cc3ccc(/C=C/CCN4CCCC5(CCNCC5)C4)cc3)c3c(C)cccc32)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O | CC(C)(C)OC(=O)NCC(=O)O | null | Cl | O=C(n1ccnc1)n1ccnc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 0.75 | Add 4N HCl in 1,4-dioxane (112 5 mmol) to a solution of tert-butyl 4-[(E)-4-[4-[[4-methyl-1-[(2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydropyran-2-yl]indol-3-yl]methyl]phenyl]but-3-enyl]-4,9-diazaspiro[5.5]undecane-9-carboxylate (22.5 mmol) in dichloromethane (200 mL) at room temperature. Stir for 3 hour... | CC(=O)OC[C@H]1O[C@@H](n2cc(Cc3ccc(/C=C/CCN4CCCC5(CCN(C(=O)CNC(=O)OC(C)(C)C)CC5)C4)cc3)c3c(C)cccc32)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O | null | 450 | null |
538,601 | ord_dataset-1884c7bf3d544afdb8d17b5d41b90a27 | null | 2002-01-01T00:03:00 | true | [Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C[O-].[Na+].[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([N:34]2[CH:38]=[CH:37][C:36]([O:39][C:40]3[C:45]([C:46](=O)[C:47]([O:49][CH3:50])=[O:48])=[CH:44][CH:43]=[CH:42][N:41]=3)=[N:35]2)=[CH:30][CH:29]=1.O>CN(C)C=O>[CH3:2][O:3][CH:4]=[C:46]([C:45]1[C:40]([O:39]... | COC[P+](c1ccccc1)(c1ccccc1)c1ccccc1 | COC(=O)C(=O)c1cccnc1Oc1ccn(-c2ccc(Cl)cc2)n1 | null | C[O-] | [Cl-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | O | null | null | null | null | null | null | null | null | null | null | 0.17 | At room temperature, a mixture of 1.86 g (5.4 mmol) of methoxymethyltriphenylphosphonium chloride and 0.98 g (5.4 mmol) of sodium methoxide solution (30% strength in methanol) in 15 ml of dimethylformamide was stirred for 10 minutes. Subsequently, the reaction mixture was admixed with 1.0 g (2.72 mmol) of methyl [2-(1-... | COC=C(C(=O)OC)c1cccnc1Oc1ccn(-c2ccc(Cl)cc2)n1 | null | 57.2 | null |
1,297,706 | ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c | null | 2013-01-01T00:05:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12](=[O:13])[C:11]([C:14]([O:16]CC)=[O:15])=[CH:10][N:9]1[CH3:19].O1CCCC1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12](=[O:13])[C:11]([C:14]([OH:16])=[O:15])=[CH:10][N:9]1[CH3:19] | CCOC(=O)c1cn(C)n(-c2ccccc2Cl)c1=O | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | In the same manner as in Reference Example 65 and using ethyl 2-(2-chlorophenyl)-1-methyl-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylate (2.8 g, 9.9 mmol), tetrahydrofuran (6 mL), methanol (5 mL) and 4N aqueous sodium hydroxide solution (8 mL) as starting materials, the title compound (2.3 g, 91%) was obtained as a white ... | Cn1cc(C(=O)O)c(=O)n1-c1ccccc1Cl | null | 92 | null |
621,908 | ord_dataset-c9f990dde2dc45d0948ecbe037a0d819 | null | 2004-01-01T00:01:00 | true | [NH:1]([C:8]1[N:9]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:10]2[C:15]([C:16](=[O:18])[CH:17]=1)=[CH:14][C:13](/[CH:19]=[CH:20]/[C:21]([O:23]C)=[O:22])=[C:12]([CH3:25])[N:11]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CC#N.O>[NH:1]([C:8]1[N:9]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:10]2[... | COC(=O)/C=C/c1cc2c(=O)cc(Nc3ccccc3)n(-c3ccccc3)c2nc1C | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | O | null | null | null | null | null | null | null | null | null | 25 | 18 | To a suspension of 2-anilino-6-[(E)-3-methoxy-3-oxo-1-propenyl]-7-methyl-1-phenyl-1,8-naphthyridin-4(1H)-one (10 mg, 0.025 mmol) in CH3CN (2.0 mL) was added 1N NaOH (2.0 mL). The suspension was stirred at room temperature for 18 h. The mixture was diluted with water (10 mL) and extracted with EtOAc. The organic layer w... | Cc1nc2c(cc1/C=C/C(=O)O)c(=O)cc(Nc1ccccc1)n2-c1ccccc1 | null | 62.4 | null |
1,333,583 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | [Cl:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[CH:4][N:3]=1.[S:9]1[CH:13]=[CH:12][CH:11]=[C:10]1B(O)O.C1COCC1.C(=O)([O-])[O-].[Na+].[Na+]>O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([C:10]2[S:9][CH:13]=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]=1 | OB(O)c1cccs1 | Clc1cc(I)ccn1 | null | Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1 | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1CCOC1 | null | null | null | null | null | null | null | null | null | 70 | 8 | A round-bottomed flask was charged with 2-chloro-4-iodopyridine (600 mg, 2.5 mmol), thiophen-2-ylboronic acid (385 mg, 3.0 mmol), trans-dichlorobis(triphenylphosphine)palladium (II) (176 mg, 0.251 mmol), THF (9 mL) and 2M aqueous sodium carbonate (3.0 mL, 6.0 mmol). The reaction mixture was stirred at 70° C. overnight.... | Clc1cc(-c2cccs2)ccn1 | null | 87.9 | null |
381,551 | ord_dataset-f367d8d2baac490b9204609a79420961 | null | 1997-01-01T00:11:00 | true | [CH3:1][N:2]=[C:3]=[O:4].[NH2:5][C:6]1[CH:7]=[C:8]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:9]2[O:13][CH2:12][C:11]([CH3:15])([CH3:14])[C:10]=2[CH:16]=1>CCOCC>[C:17]([C:8]1[C:9]2[O:13][CH2:12][C:11]([CH3:14])([CH3:15])[C:10]=2[CH:16]=[C:6]([NH:5][C:3]([NH:2][CH3:1])=[O:4])[CH:7]=1)([CH3:20])([CH3:19])[CH3:18] | CN=C=O | CC(C)(C)c1cc(N)cc2c1OCC2(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | null | null | null | null | null | null | null | null | null | null | null | 0.5 | Methylisocyanate (0.14 mL, 2.28 mmol) is added dropwise to a solution of 5-amino-7-tert-butyl-2,3-dihydro-3,3-dimethylbenzofuran (500 mg, 2.28 mmol) in Et2O (5 mL). A solid forms over 0.5 h and the reaction is quenched with H2O (10 mL) after 1 h. The reaction is extracted with Et2O (3×10 mL) and the organic layers drie... | CNC(=O)Nc1cc(C(C)(C)C)c2c(c1)C(C)(C)CO2 | null | 55.5 | null |
709,838 | ord_dataset-c8069773c1a148aca8ab417108daacc5 | null | 2006-01-01T00:05:00 | true | [C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C@@H:10]([OH:13])[CH2:11]O)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[OH-].[Na+]>C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C@H:10]1[O:13][CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH... | CC(C)(C)OC(=O)N[C@@H](Cc1ccccc1)[C@@H](O)CO | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | c1ccncc1 | null | null | null | null | null | null | null | null | null | 0 | 4 | To the mixture of (2R,3S)-3-(t-butoxycarbonyl)amino-4-phenyl-butane-1,2-diol (44 g) and 400 ml of pyridine, 60 g (2 equivalents) of p-TsCl was added and the solution was stirred at 0° C. for 4 hours. After pH of the solution was adjusted 10 with 25% NaOH and it was stirred at 0° C. for 3 hours. 400 ml of methylene chlo... | CC(C)(C)OC(=O)N[C@@H](Cc1ccccc1)[C@@H]1CO1 | null | null | null |
1,743,455 | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | null | 2016-01-01T00:07:00 | true | [CH2:1]([O:3][C:4]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[N:7]=[CH:6][C:5]=1[C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27]([OH:29])=O)=[C:22]([F:30])[CH:21]=1)[CH3:2].[NH2:31][C:32]1[CH:33]=[C:34]([C:43]([F:46])([F:45])[F:44])[C:35]([C:38]([CH3:42])([CH3:41])[CH2:39][OH:4... | CCOc1cc(OCc2ccc(OC)cc2)ncc1-c1ccc(CC(=O)O)c(F)c1 | CC(C)(CO)c1ncc(N)cc1C(F)(F)F | null | CN(C)C(On1nnc2cccnc21)=[N+](C)C | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | null | null | A solution of 2-(4-(4-ethoxy-6-((4-methoxybenzyl)oxy)pyridin-3-yl)-2-fluorophenyl)acetic acid (50 mg, 0.122 mmol), 2-(5-amino-3-(trifluoromethyl)pyridin-2-yl)-2-methylpropan-1-ol (28.5 mg, 0.122 mmol), HATU (92 mg, 0.243 mmol) and DIEA (0.064 mL, 0.365 mmol) in DCM (10 mL) was stirred at 25° C. After LCMS analysis show... | CCOc1cc(OCc2ccc(OC)cc2)ncc1-c1ccc(CC(=O)Nc2cnc(C(C)(C)CO)c(C(F)(F)F)c2)c(F)c1 | null | 26.2 | null |
1,686,070 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | [NH2:1][C@@H:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][OH:4].CCN(CC)CC.[Cl:18][CH2:19][C:20](Cl)=[O:21]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:18][CH2:19][C:20]([NH:1][C@@H:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][OH:4])=[O:21] | N[C@H](CO)c1ccccc1 | O=C(Cl)CCl | null | CN(C)c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 0 | 0.25 | To a solution of (S)-2-amino-2-phenylethanol (0.852 g, 6.21 mmol), Et3N (0.952 mL, 6.83 mmol), DMAP (76 mg, 0.621 mmol) in CH2Cl2 (10 mL) at 0° C. was added 2-chloroacetyl chloride (0519 mL, 6.52 mmol), and the resulting mixture was stirred at 0° C. for 15 min. The reaction mixture was washed with aqueous HCl (1 M, 20 ... | O=C(CCl)N[C@H](CO)c1ccccc1 | null | 45.2 | null |
1,679,351 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | [C:1]([C:5]1[S:9][C:8]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)=O.CC(C)=O.C([Li])CCC.[B:27](OC)([O:30]C)[O:28]C>C1COCC1>[C:1]([C:5]1[S:9][C:8]([C:10]2[S:11][C:12]([B:27]([OH:30])[OH:28])=[CH:13][CH:14]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3] | COB(OC)OC | CC(C)(C)c1ccc(-c2cccs2)s1 | null | O=C=O | [Li]CCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 0.25 | In a flame-dried, 500 mL round bottom flask, 5-(t-butyl)-2,2′-bithiophene (from U152-001, 13 g, 58.5 mmol) was dissolved in anhydrous THF (200 mL) and the solution was cooled to −78° C. (dry ice/acetone). n-butyl lithium (2.5 M in hexanes, 25.7 mL, 64.3 mmol) was added dropwise over a period of 10 minutes, and the resu... | CC(C)(C)c1ccc(-c2ccc(B(O)O)s2)s1 | null | 96 | null |
1,585,228 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | [CH:1]1([C:4]2[O:5][C:6]3[C:12]([C:13]4[CH:18]=[C:17]([CH3:19])[C:16](=[O:20])[N:15]([CH3:21])[CH:14]=4)=[CH:11][C:10]([NH:22][S:23]([CH2:26][CH3:27])(=[O:25])=[O:24])=[CH:9][C:7]=3[CH:8]=2)[CH2:3][CH2:2]1>CO.[Pd]>[CH3:21][N:15]1[C:16](=[O:20])[C:17]([CH3:19])=[CH:18][C:13]([C:12]2[C:6]3[O:5][CH:4]([CH2:1][CH2:2][CH3:3... | CCS(=O)(=O)Nc1cc(-c2cc(C)c(=O)n(C)c2)c2oc(C3CC3)cc2c1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | 1 | A mixture of the title compound from Step 4 (70 mg, 0.18 mmol) and 10 mg of Pd/C in 40 mL of MeOH was stirred under a H2 atmosphere at room temperature for 1 h. The resulting mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by prep-HPLC to give the title compound (... | CCCC1Cc2cc(NS(=O)(=O)CC)cc(-c3cc(C)c(=O)n(C)c3)c2O1 | null | 14.2 | null |
1,322,092 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | [Cl:1]C1C=C2C(C=CN=C2)=CC=1F.[ClH:13].[NH:14]1[CH2:19][CH2:18][CH:17]([O:20][C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=2)[CH:27]=[N:26][CH:25]=[CH:24]3)[CH2:16][CH2:15]1>>[ClH:1].[Cl:13][C:30]1[CH:29]=[C:28]2[C:23]([CH:24]=[CH:25][N:26]=[CH:27]2)=[CH:22][C:21]=1[O:20][CH:17]1[CH2:18][CH2:19][NH:14][CH2:15][CH2:16]1 | Fc1cc2ccncc2cc1Cl | c1cc2cc(OC3CCNCC3)ccc2cn1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Starting from 7-Chloro-6-fluoro-isoquinoline (150), the title compound was prepared by the same synthetic route as for compound 124. Rt=0.66 min (Method #1), detected mass: 263.1/265.1 (M+H+). | Clc1cc2cnccc2cc1OC1CCNCC1 | null | null | null |
794,758 | ord_dataset-744b04e8228742eb9aa4bde36f5dedf1 | null | 2007-01-01T00:10:00 | true | [C:1]1([C:11]([OH:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[N+:14]([O-])([OH:16])=[O:15]>S(=O)(=O)(O)O>[N+:14]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[CH:4]=[CH:3][N:2]=[C:1]2[C:11]([OH:13])=[O:12])([O-:16])=[O:15] | O=C(O)c1nccc2ccccc12 | O=[N+]([O-])O | null | O=S(=O)(O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 0 | 1 | Isoquinoline-1-carboxylic acid (3.98 g, 23.0 mmol) was dissolved in conc. sulfuric acid (16 ml) at 0° C. A mixture of conc. sulfuric acid (5 ml) and fuming nitric acid (5 ml) was added over 10 min. and the reaction stirred for a further 1 h at 0° C., then poured into ice-water (400 ml). The solid was collected by filtr... | O=C(O)c1nccc2c([N+](=O)[O-])cccc12 | null | 82 | null |
840,739 | ord_dataset-074f86301ec5441ab3b52d902ac06949 | null | 2008-01-01T00:09:00 | true | [CH3:1][C:2]1[O:11][C:5]2[N:6]=[CH:7][N:8]=[C:9](Cl)[C:4]=2[CH:3]=1.[CH3:12][S-:13].[Na+]>C(#N)C>[CH3:1][C:2]1[O:11][C:5]2[N:6]=[CH:7][N:8]=[C:9]([S:13][CH3:12])[C:4]=2[CH:3]=1 | C[S-] | Cc1cc2c(Cl)ncnc2o1 | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 6-methyl-4-chlorofuro[2,3-d]pyrimidine (U.S. Pat. No. 3,577,420, example IG) (219 mg) in acetonitrile (25 mL) was heated under reflux with sodium thiomethoxide (190 mg) for 16 hours. The mixture was filtered and the solids washed with acetonitrile. Evaporation of the solvent afforded the title compound as... | CSc1ncnc2oc(C)cc12 | null | 90 | null |
195,117 | ord_dataset-b83b16f2fb1a4f8782f3d82c1766cc6b | null | 1989-01-01T00:08:00 | true | [SH:1][CH2:2][C:3]([OH:5])=[O:4].[Cl:6][C:7]1[CH:17]=[CH:16][C:10]([CH:11]=[CH:12][C:13]([OH:15])=[O:14])=[CH:9][CH:8]=1.C(N(CC)CC)C.S(=O)(=O)(O)O>O1CCOCC1>[C:3]([CH2:2][S:1][CH:11]([C:10]1[CH:9]=[CH:8][C:7]([Cl:6])=[CH:17][CH:16]=1)[CH2:12][C:13]([OH:15])=[O:14])([OH:5])=[O:4] | O=C(O)CS | O=C(O)C=Cc1ccc(Cl)cc1 | null | O=S(=O)(O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | null | To a stirred mixture of mercaptoacetic acid (5.04 g, 3.8 ml, 54.7 mmol) and 4-chlorocinnamic acid (10.0 g, 54.7 mmol) in 20 ml of dioxane is added dropwise a solution of triethylamine (6.90 g, 9.53 ml, 68.0 mmol) in 20 ml of dioxane. The mixture is heated under reflux for 5 hours, then cooled and poured into ice, acidi... | O=C(O)CSC(CC(=O)O)c1ccc(Cl)cc1 | null | null | null |
1,667,275 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | [C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2].[NH2:8][C:9]1[N:14]=[CH:13][N:12]=[C:11]2[N:15]([CH:19]([C:21]3[C:22]([O:38][CH3:39])=[C:23]([CH2:29][CH2:30][C:31]([O:33]C(C)(C)C)=[O:32])[C:24]([CH3:28])=[C:25]([Cl:27])[CH:26]=3)[CH3:20])[N:16]=[C:17]([CH3:18])[C:10]=12>C(Cl)Cl>[F:4][C:3]([F:6])([F:5])[C:1]([OH:7])=[O:2]... | COc1c(C(C)n2nc(C)c3c(N)ncnc32)cc(Cl)c(C)c1CCC(=O)OC(C)(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 2 | TFA (0.3 mL, 4 mmol) was added to a solution of tert-butyl 3-{3-[1-(4-amino-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl}propanoate (35 mg, 0.076 mmol) in methylene chloride (0.2 mL) and the mixture was stirred at room temperature for 2 h. The solvent was removed and the product wa... | COc1c(C(C)n2nc(C)c3c(N)ncnc32)cc(Cl)c(C)c1CCC(=O)O | null | null | null |
1,750,366 | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | null | 2016-01-01T00:07:00 | true | [OH:1][CH2:2][CH2:3][N:4]([CH3:32])[C:5]1[CH:10]=[C:9]([C:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH:12]=2)[CH:8]=[C:7]([NH:24][C:25]2[CH:30]=[C:29]([CH3:31])[CH:28]=[CH:27][N:26]=2)[N:6]=1>CO.[Pd]>[OH:1][CH2:2][CH2:3][N:4]([CH3:32])[C:5]1[CH:10]=[C:9]([CH:11]2[CH2:12... | Cc1ccnc(Nc2cc(C3=CCN(C(=O)OC(C)(C)C)CC3)cc(N(C)CCO)n2)c1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | tert-butyl 4-(2-((2-hydroxyethyl)(methyl)amino)-6-(4-methylpyridin-2-ylamino)pyridin-4-yl)-5,6-dihydropyridine-1(2H)-carboxylate (130 mg, 0.29 mmol) was dissolved in MeOH (50 mL). The resulting solution was hydrogenated in H-Cube hydrogenation reactor, with 10% Pd/C cartridge under 40 bar, eluded 1 mL/min at 30° C. for... | Cc1ccnc(Nc2cc(C3CCN(C(=O)OC(C)(C)C)CC3)cc(N(C)CCO)n2)c1 | null | 78.1 | null |
1,354,305 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | [CH2:1]([O:8][C:9](=[O:16])[NH:10][C@@H:11]([CH3:15])[CH2:12][CH2:13][OH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])(C)C.N1C=CN=C1>CN(C=O)C.CCOC(C)=O>[CH2:1]([O:8][C:9](=[O:16])[NH:10][C@@H:11]([CH3:15])[CH2:12][CH2:13][O:14][SiH2:17][C:20]([CH3:23])([CH3:22])[CH3:21])[C... | C[C@@H](CCO)NC(=O)OCc1ccccc1 | CC(C)(C)[Si](C)(C)Cl | null | c1c[nH]cn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 1 | (3-Hydroxy-1-(S)-methyl-propyl)-carbamic acid benzyl ester (8.02 g, 35.9 mmol) was taken up in DMF (75 mL). tert-Butyl-dimethylsilyl chloride (8.12 g, 53.9 mmol) was added to the solution followed by imidazole (4.15 g, 61.0 mmol). The reaction was stirred at rt and monitored by TLC. The reaction was determined to be co... | C[C@@H](CCO[SiH2]C(C)(C)C)NC(=O)OCc1ccccc1 | null | 114.6 | null |
803,562 | ord_dataset-ed846b4b229e4bb09ad9dba95ad7ebeb | null | 2008-01-01T00:01:00 | true | C[O:2][C:3](=[O:23])[CH:4]([NH:15]C(OC(C)(C)C)=O)[CH2:5][C:6]1[CH:11]=[C:10]([Br:12])[C:9]([OH:13])=[C:8]([Br:14])[CH:7]=1.Br[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[F:32]>>[NH2:15][CH:4]([CH2:5][C:6]1[CH:7]=[C:8]([Br:14])[C:9]([O:13][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[F:32])=[C:10]([Br:1... | COC(=O)C(Cc1cc(Br)c(O)c(Br)c1)NC(=O)OC(C)(C)C | Fc1ccccc1CBr | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Methyl-2-tert-butoxycarbonylamino-3-(3,5-dibromo-4-hydroxyphenyl)propionate (0.035 mmol) was coupled with 1-bromomethyl-2-fluorobenzene and hydrolyzed using the method described in “General procedure for the preparation of Examples 8-22”. This gave 10% yield of 2-amino-3-[3,5-dibromo-4-(2-fluorobenzyloxy)phenyl]propion... | NC(Cc1cc(Br)c(OCc2ccccc2F)c(Br)c1)C(=O)O | null | 10 | null |
1,660,575 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [Si:1]([O:8][C@H:9]1[C@H:13]2[O:14][CH2:15][C@@H:16]([O:17][C:18]3[N:40]([CH2:41][O:42][CH2:43][CH2:44][Si:45]([CH3:48])([CH3:47])[CH3:46])[C:21]4=[N:22][C:23]([C:27]5[CH:32]=[CH:31][C:30]([C@H:33]6[CH2:38][CH2:37][C@H:36]([OH:39])[CH2:35][CH2:34]6)=[CH:29][CH:28]=5)=[C:24]([Cl:26])[CH:25]=[C:20]4[N:19]=3)[C@H:12]2[O:1... | O=C(Cl)N1CCOCC1 | CC(C)(C)[Si](C)(C)O[C@@H]1CO[C@H]2[C@@H]1OC[C@H]2Oc1nc2cc(Cl)c(-c3ccc([C@H]4CC[C@H](O)CC4)cc3)nc2n1COCC[Si](C)(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | 50 | 12 | (trans)-4-(4-(2-((3R,3aR,6R,6aS)-6-(tert-Butyldimethylsilyloxy)hexahydrofuro[3,2-b]-furan-3-yloxy)-6-chloro-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-b]pyridin-5-yl)phenyl)cyclohexanol (50 mg) is dissolved in pyridine (1 mL), treated with morpholine-4-carbonyl chloride (25 μL) and stirred for 12 hours at 50° ... | CC(C)(C)[Si](C)(C)O[C@@H]1CO[C@H]2[C@@H]1OC[C@H]2Oc1nc2cc(Cl)c(-c3ccc([C@H]4CC[C@H](OC(=O)N5CCOCC5)CC4)cc3)nc2n1COCC[Si](C)(C)C | null | null | null |
1,139,610 | ord_dataset-68715347640045adb1b09e6a04722b0e | null | 2012-01-01T00:03:00 | true | [CH3:1][NH:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][CH:10]=2)[CH:4]=1.[CH2:22]([N:29]=[C:30]=[O:31])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>>[CH2:22]([NH:29][C:30](=[O:31])[N:2]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[CH:10]=[CH:1... | CCCCCCCN=C=O | CCOC(=O)CCc1ccc(-c2cc(NC)ccn2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 270 mg (0.63 mmol, 1 eq) of ethyl 3-[4-(4-methylaminopyrid-2-yl)phenyl]propanoate are mixed with 0.6 mL (3.7 mmol, 6 eq) of heptyl isocyanate and then irradiated in a microwave machine for 2 times 30 minutes, while keeping the temperature constant at 100° C. The reaction mixture is chromatographed on silica gel (90/10 ... | CCCCCCCNC(=O)N(C)c1ccnc(-c2ccc(CCC(=O)OCC)cc2)c1 | null | 97 | null |
1,694,685 | ord_dataset-c1e70ad912eb438f8d34b1dc681f809a | null | 2016-01-01T00:02:00 | true | FC(F)(F)S(O[Si:7]([CH3:18])([CH3:17])[CH:8]1[C:12]([CH3:13])=[C:11]([CH3:14])[C:10]([CH3:15])=[C:9]1[CH3:16])(=O)=O.[C:21]([C:25]1[CH:30]=[CH:29][C:28]([C-:31]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH:33]=[CH:32]2)=[CH:27][CH:26]=1)([CH3:24])([CH3:23])[CH3:22].[Li+]>CCOCC>[C:21]([C:25]1[CH:26]=[CH:27][C:28]([... | CC1=C(C)C([Si](C)(C)OS(=O)(=O)C(F)(F)F)C(C)=C1C | CC(C)(C)c1ccc(-[c-]2ccc3ccccc32)cc1 | null | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | null | null | null | null | null | null | null | null | null | null | null | 18 | To a solution of dimethyl(2,3,4,5-tetramethylcyclopenta-2,4-dien-1-yl)silyl trifluoromethanesulfonate (Compound C, 7.50 g, 22.8 mmol, 1.00 eq.) in ether (25 mL) at −35° C. was added lithium (1-(4-t-butylphenyl)indenide) (6.20 g, 24.4 mmol, 1.07 eq.). The reaction was stirred for 18 hours, and was then evaporated under ... | CC1=C(C)C([Si](C)(C)C2C=C(c3ccc(C(C)(C)C)cc3)c3ccccc32)C(C)=C1C | null | null | null |
518,493 | ord_dataset-a495451286334c5c9bbcbd48a00c1350 | null | 2001-01-01T00:09:00 | true | [OH:1][CH2:2][CH:3]([CH2:5][OH:6])[OH:4]>[Pt].O>[OH:1][CH2:2][C:3]([C@H:5]([C@H:2]([CH2:3][OH:4])[OH:1])[OH:6])=[O:4] | OCC(O)CO | null | null | [Pt] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | null | 48 | One hundred ml aliquots of a nutrient culture medium, consisting of 2 w/v % trypton soya broth, one w/v % glycerol and deionized water, were distributed to ten 500-ml shaking flasks, followed by autoclaving the flasks at 120° C. for 20 min. Thereafter, the flasks were cooled and inoculated with a seed culture of Glucon... | O=C(CO)[C@@H](O)[C@@H](O)CO | null | null | null |
1,139,637 | ord_dataset-68715347640045adb1b09e6a04722b0e | null | 2012-01-01T00:03:00 | true | [CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[N:11]1[CH:15]=[C:14]([CH:16]3[CH2:18][CH2:17]3)[NH:13][C:12]1=[O:19])[CH2:8]2.Br[CH2:21][CH:22]1[CH2:24][CH2:23]1>>[CH:1]12[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH:2]1[N:11]1[CH:15]=[C:14]([CH:16]3[CH2:17][CH2:18]3)[N:13]([CH2:21][CH:22]3... | O=c1[nH]c(C2CC2)cn1C1C2CC3CC(C2)CC1C3 | BrCC1CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | This material was obtained in analogy to the procedure outlined in example 23 from 1-adamantan-2-yl-4-cyclopropyl-1,3-dihydro-imidazol-2-one (obtained in example 15, 100 mg) by alkylation with bromomethylcyclopropane (57 mg). 1-Adamantan-2-yl-4-cyclopropyl-3-cyclopropylmethyl-1,3-dihydro-imidazol-2-one was obtained as ... | O=c1n(C2C3CC4CC(C3)CC2C4)cc(C2CC2)n1CC1CC1 | null | null | null |
917,390 | ord_dataset-8e59bd24817446f7b1c68e805b8e5f1d | null | 2009-01-01T00:11:00 | true | [Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([NH2:9])[CH:3]=1.[Cl:10][C:11]([F:16])([F:15])[C:12](O)=O>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[NH:8][C:12]([C:11]([Cl:10])([F:16])[F:15])=[N:9][C:4]=2[CH:3]=1 | O=C(O)C(F)(F)Cl | Nc1ccc(Br)cc1N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 4-bromo-phenylene-diamine (1.00 g, 5.35 mmol), chlorodifluoroacetic acid (3.0 mL, 35.4 mmol), and a drop of water was heated to 80° C. for 14 hours. The crude product was purified by chromatography (silica, hexanes: EtOAc, 4:1) to afford the title compound as a colorless oil (0.63 g, 42%). | FC(F)(Cl)c1nc2cc(Br)ccc2[nH]1 | null | 41.8 | null |
1,541,702 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | C(Cl)(=O)C(C)(C)C.[CH3:8][O:9][C:10]([C:12]1[CH:13]=[C:14]([CH:20]=[CH:21][CH:22]=1)[O:15][CH2:16][C:17]([OH:19])=O)=[O:11].C(N(CC)CC)C.[CH3:30][O:31][C:32]1[CH:37]=[C:36]([O:38][C:39]2[CH:40]=[C:41]([NH:46][CH3:47])[C:42]([NH2:45])=[CH:43][CH:44]=2)[CH:35]=[CH:34][N:33]=1>ClCCl>[CH3:30][O:31][C:32]1[CH:37]=[C:36]([O:3... | COC(=O)c1cccc(OCC(=O)O)c1 | CNc1cc(Oc2ccnc(OC)c2)ccc1N | null | CC(C)(C)C(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 25 | 1 | Pivaloyl chloride (1.74 mL, 14.2 mmol) was added dropwise to a solution of [3-(methoxycarbonyl)phenoxy]acetic acid produced in Example (1c) (3.27 g, 15.6 mmol) and triethylamine (1.97 mL, 14.2 mmol) in dichloromethane (40 mL) in a nitrogen atmosphere at 0° C. After one hour, a solution of 4-[(2-methoxypyridin-4-yl)oxy]... | CNc1cc(Oc2ccnc(OC)c2)ccc1NC(=O)COc1cccc(C(=O)OC)c1 | null | 77.4 | null |
1,684,407 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | [F:1][CH:2]([F:12])[O:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([CH2:10]O)[CH:5]=1.C(Br)(Br)(Br)[Br:14].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[Br:14][CH2:10][C:6]1[CH:5]=[C:4]([O:3][CH:2]([F:12])[F:1])[CH:9]=[CH:8][N:7]=1 | OCc1cc(OC(F)F)ccn1 | BrC(Br)(Br)Br | null | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 1 | A solution of (4-(difluoromethoxy)pyridin-2-yl)methanol (250 mg; 1.42 mmol) in anh. DCM (12 ml) was treated at rt with CBr4 (473 mg; 1.42 mmol), and with PPh3 (374 mg; 1.42 mmol). The resulting mixture was further stirred at rt, under nitrogen, for 1 h. Concentration to dryness under reduced pressure, and subsequent pu... | FC(F)Oc1ccnc(CBr)c1 | null | null | null |
892,257 | ord_dataset-11068b1e475b4c5b82e56726ab0dddb7 | null | 2009-01-01T00:07:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]=[O:18])=[CH:13][CH:12]=1)[C:5]#[N:6].C(=O)([O-])[O-:20].[K+].[K+].OO>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]=[O:18])=[CH:13][CH:12]=1)[C:5]([NH2:6])=[O:20] | N#Cc1ccc(Oc2ccc(C=O)cc2)c(Cl)c1 | O=C([O-])[O-] | null | OO | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | null | null | null | null | null | null | null | null | null | null | 25 | 3 | Cool a solution of 3-chloro-4-(4-formyl-phenoxy)-benzonitrile (1.57 g, 6.10 mmol) in dimethylsulfoxide (50 mL) to 0° C. Add potassium carbonate (0.42 g, 3.05 mmol) followed by 30% aqueous hydrogen peroxide (1.83 mL, 6.10 mmol). Remove the cooling bath and let stir at rt for 3 hrs. Pour into water (100 mL) and after tri... | NC(=O)c1ccc(Oc2ccc(C=O)cc2)c(Cl)c1 | null | 166.5 | null |
750,622 | ord_dataset-844a22e1fcab44a5b59c5e2922b2855a | null | 2007-01-01T00:01:00 | true | [C:1]([O:5][C:6](=[O:24])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]2[C:19](=[O:20])[C:18]([CH3:21])=[C:17](Cl)[NH:16][C:15]2=[O:23])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[SH2:25].[Na]>CN(C)C=O>[C:1]([O:5][C:6](=[O:24])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]2[C:19](=[O:20])[C:18]([CH3:21])=[C:17]([SH:25])[NH:16][... | S | Cc1c(Cl)[nH]c(=O)n(Cc2ccc(C(=O)OC(C)(C)C)cc2)c1=O | null | [Na] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 60 | 1 | The product of Example 1, Step (A) (0.54 g) was dissolved in dimethylformamide (5 mL) wand treated with sodium hydrogen sulfide (0.29 g) and heated at 60° C. for 18 hours. The solvent was removed in a vacuum and the residue stirred with 1 M hydrochloric acid (15 mL) for 1 hour. The resulting solid was filtered, rinsed ... | Cc1c(S)[nH]c(=O)n(Cc2ccc(C(=O)OC(C)(C)C)cc2)c1=O | null | 88.6 | null |
1,224,304 | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | null | 2012-01-01T00:11:00 | true | [F:1][C:2]1[CH:3]=[C:4]([CH2:10][CH:11]([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]=[C:6]([F:9])[C:7]=1[OH:8].C(=O)([O-])[O-].[K+].[K+].[CH2:24](Cl)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C=O)C.O>[CH2:24]([O:8][C:7]1[C:2]([F:1])=[CH:3][C:4]([CH2:10][CH:11]([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:... | ClCc1ccccc1 | CCOC(=O)C(C)Cc1cc(F)c(O)c(F)c1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 50 | 8 | To a mixture of ethyl 3-(3,5-difluoro-4-hydroxyphenyl)-2-methylpropanoate (9) (930 mg, 3.81 mmol) and potassium carbonate (1.05 g, 7.62 mmol) in DMF (8 mL) was added benzyl chloride (0.53 mL, 4.57 mmol) and stirred overnight at 50° C. The reaction was diluted with water and extracted with ethyl acetate (3×25 mL). The o... | CCOC(=O)C(C)Cc1cc(F)c(OCc2ccccc2)c(F)c1 | null | null | null |
748,127 | ord_dataset-4b705442211b4a3988e26d5f65098160 | null | 2006-01-01T00:12:00 | true | [CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]([CH:9]([CH2:17][CH2:18][CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:10]([O:12]C(C)(C)C)=[O:11])=[O:8])[CH:3]=1>FC(F)(F)C(O)=O>[CH2:24]([O:23][C:21](=[O:22])[CH2:20][CH2:19][CH2:18][CH2:17][CH:9]([C:7]([C:4]1[CH:3]=[C:2]([CH3:1])[O:6][N:5]=1)=[O:8])[C:10]([OH:12])=[O:11])[... | CCOC(=O)CCCCC(C(=O)OC(C)(C)C)C(=O)c1cc(C)on1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 1-tert-butyl 7-ethyl 2-[(5-methyl-3-isoxazolyl)carbonyl]heptanedioate (126 mg) in trifluoroacetic acid (1 mL) was stirred for 1.5 hour at room temperature. The volatile was evaporated off, and azeotroped with toluene to give 7-ethoxy-2-[(5-methyl-3-isoxazolyl)carbonyl]-7-oxoheptanoic acid as a pale orange... | CCOC(=O)CCCCC(C(=O)O)C(=O)c1cc(C)on1 | null | 100 | null |
870,968 | ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | null | 2009-01-01T00:03:00 | true | C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20][C:21]([Br:24])(Br)Br.[C:25]([O:29][C:30]([N:32]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:34]([CH:41]=O)=[CH:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26].CCCCCC>C(Cl)Cl>[C:25]([O:29][C:30]([N:32]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:34]([CH:41]=[C:21]([Br... | CC(C)(C)OC(=O)n1cc(C=O)c2ccccc21 | BrC(Br)(Br)Br | null | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCCCCC | null | null | null | null | null | null | null | null | null | 0 | 1 | Triphenylphosphane (17.2 g, 65.5 mmole) was added in portions at 0° C., while stirring and within 60 min to a solution of tetrabromocarbon (10.9 g, 32.7 mmole) in DCM (120 ml) and post-stirred for 1 h at 0° C. 3-formyl-indole-1-carboxylic acid-tert-butylester (4 g, 16.4 mmole) dissolved in DCM (30 ml) was subsequently ... | CC(C)(C)OC(=O)n1cc(C=C(Br)Br)c2ccccc21 | null | 95.2 | null |
1,058,330 | ord_dataset-373415d3e0e54004837cf4831e67666f | null | 2011-01-01T00:05:00 | true | [CH3:1][O:2][C@H:3]1[CH2:20][CH2:19][C@@:18]2([CH3:21])[C:5](=[CH:6][CH2:7][C@@H:8]3[C@@H:17]2[CH2:16][CH2:15][C@@:13]2([CH3:14])[C@H:9]3[CH2:10][CH2:11][C@@H:12]2[OH:22])[CH2:4]1.[OH:23]N1C(=O)C2=CC=CC=C2C1=O>>[CH3:1][O:2][C@H:3]1[CH2:20][CH2:19][C@@:18]2([CH3:21])[C:5](=[CH:6][C:7](=[O:23])[C@@H:8]3[C@@H:17]2[CH2:16]... | O=C1c2ccccc2C(=O)N1O | CO[C@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4CC[C@H](O)[C@@]4(C)CC[C@@H]32)C1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 3β-methoxyandrost-5-ene-17β-ol (27) was subjected to air oxidation in the presence of N-hydroxyphthalimide and the producT 3β-methoxy-17β-hydroxyandrost-5-ene-7-one (28) was obtained in 53% yield. An analytical sample was obtained by recrystallization from acetone-hexane, m.p. 202-4° C. | CO[C@H]1CC[C@@]2(C)C(=CC(=O)[C@H]3[C@@H]4CC[C@H](O)[C@@]4(C)CC[C@@H]32)C1 | null | 53 | null |
375,328 | ord_dataset-ee5599340390470d8e5b5ac1feddf9d6 | null | 1997-01-01T00:08:00 | true | [C:1]([N:4]1[CH:8](O)[CH2:7][CH:6]([CH2:10][CH3:11])[C:5]1([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])(=[O:3])[CH3:2].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(Cl)Cl>[C:1]([N:4]1[CH2:8][CH2:7][CH:6]([CH2:10][CH3:11])[C:5]1([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:1... | CCOC(=O)C1(C(=O)OCC)C(CC)CC(O)N1C(C)=O | null | null | CC[SiH](CC)CC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | 25 | null | To a solution of diethyl 1-acetyl-5-hydroxy-3-ethylpyrrolidine-2,2-dicarboxylate (287 g, 0.95 mol) and triethylsilane (228 mL, 1.43 mol) in CH2Cl2 (3 L) under argon was added trifluoroacetic acid (735 mL, 9.53 mol) dropwise with stirring while maintaining the internal temperature at 25° C. by means of an ice bath. Afte... | CCOC(=O)C1(C(=O)OCC)C(CC)CCN1C(C)=O | null | 137.6 | null |
1,027,560 | ord_dataset-83acb82dc5ba4f7aba439b9875aaac43 | null | 2011-01-01T00:02:00 | true | [CH:1]([C:3]1[CH:8]=[C:7]([C@@H:9]([NH:12][C:13]([C:15]2[C:16]3[CH:23]=[N:22][N:21]([C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=4)[C:17]=3[CH:18]=[N:19][CH:20]=2)=[O:14])[CH2:10][CH3:11])[CH:6]=[CH:5][N:4]=1)=[O:2].[BH4-].[Na+]>C1COCC1.CO>[OH:2][CH2:1][C:3]1[CH:8]=[C:7]([C@@H:9]([NH:12][C:13]([C:15]2[C:16]3[CH:... | CC[C@H](NC(=O)c1cncc2c1cnn2-c1ccc(F)cc1)c1ccnc(C=O)c1 | null | null | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 1.5 | To a chilled (0° C.) solution of 1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid [(S)-1-(2-formyl-pyridin-4-yl)-propyl]-amide (95 mg, 0.24 mmol) in THF (2 mL) and methanol (2 mL) was added sodium borohydride (17.8 mg, 0.47 mmol). The mixture was then warmed to room temperature. After 1.5 hours, the mixt... | CC[C@H](NC(=O)c1cncc2c1cnn2-c1ccc(F)cc1)c1ccnc(CO)c1 | null | null | null |
757,009 | ord_dataset-1b0cd79134f0450eaac8396a4f956c30 | null | 2007-01-01T00:02:00 | true | [NH2:1][C:2]1[N:6]([CH2:7][CH2:8][OH:9])[N:5]=[CH:4][C:3]=1[C:10]#N.Cl.C[OH:14]>[C].[Pd]>[NH2:1][C:2]1[N:6]([CH2:7][CH2:8][OH:9])[N:5]=[CH:4][C:3]=1[CH:10]=[O:14] | N#Cc1cnn(CCO)c1N | CO | null | [Pd] | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 0.25 | To a solution of 5-amino-1-(2-hydroxyethyl)-1H-pyrazole-4-carbonitrile (15 g) in methanol (300 ml) was added hydrochloric acid (1.8 ml) under ice-cooling. The resulting solution was stirred for 15 minutes. The mixture was treated with 10% palladium carbon (7.5 g) under a hydrogen atmosphere at room temperature for 3 ho... | Nc1c(C=O)cnn1CCO | null | null | null |
704,611 | ord_dataset-c408dfed796e4354b61e312e67f7143f | null | 2006-01-01T00:04:00 | true | [CH:1]1([CH2:7][C@H:8]([CH2:12][C:13]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[O:14])[C:9]([OH:11])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O.[NH2:28][CH:29]([CH2:41][CH3:42])[C@@H:30]([C:32]1[N:36]=[C:35]([C:37]([F:40])([F:39])[F:38])[O:34][N:33]=1)[OH:31].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C... | O=C(O)[C@@H](CC(=O)N1CCOCC1)CC1CCCCC1 | CCC(N)[C@H](O)c1noc(C(F)(F)F)n1 | null | CN(C)C(On1nnc2cccnc21)=[N+](C)C | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 8 | A solution of (R)-2-Cyclohexylmethyl-4-morpholin-4-yl-4-oxo-butyric acid (223 mg, 0.788 mmol) in dimethylformamide (10 ml) was treated successively with (S)-2-Amino-1-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-butan-1-ol; compound with trifluoroacetic acid (267 mg, 0.788 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetram... | CC[C@H](NC(=O)[C@@H](CC(=O)N1CCOCC1)CC1CCCCC1)C(O)c1noc(C(F)(F)F)n1 | null | 83.8 | null |
605,072 | ord_dataset-273fda773e864aaf9b71a30a2d9f2162 | null | 2003-01-01T00:08:00 | true | [CH2:1]([NH:9][C:10]([N:12]1[CH2:17][CH2:16][CH:15]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][NH:27][CH2:28][C@@H:29]([C:31]3[CH:36]=[CH:35][C:34]([O:37]CC4C=CC=CC=4)=[C:33]([NH:45][S:46]([CH3:49])(=[O:48])=[O:47])[CH:32]=3)[OH:30])=[CH:21][CH:20]=2)[CH2:14][CH2:13]1)=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:... | [H][H] | CCCCCCCCNC(=O)N1CCC(Nc2ccc(CCNC[C@H](O)c3ccc(OCc4ccccc4)c(NS(C)(=O)=O)c3)cc2)CC1 | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | 4-(4-{2-[(2R)-2-(4-Benzyloxy-3-methanesulfonylamino-phenyl)-2-hydroxy-ethylamino]-ethyl}-phenylamino)-piperidine-1-carboxylicacid octylamide (0.152 g, 0.219 mmol) was dissolved in ethanol (40 mL) and 10% palladium on carbon (0.05 g) added. The solution was shaken in a Parr apparatus at 50 psi hydrogen atmosphere for 2 ... | CCCCCCCCNC(=O)N1CCC(Nc2ccc(CCNC[C@H](O)c3ccc(O)c(NS(C)(=O)=O)c3)cc2)CC1 | null | 62.1 | null |
1,760,489 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | [C:1]([OH:12])(=O)/[CH:2]=[CH:3]/[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[S:13]1[CH2:17][CH2:16][NH:15][CH2:14]1>>[C:1]([N:15]1[CH2:16][CH2:17][S:13][CH2:14]1)(=[O:12])/[CH:2]=[CH:3]/[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10] | CCCCCCC/C=C/C(=O)O | C1CSCN1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The same procedures as in Example 1 were carried out using (E)-2-decenoic acid and thiazolidine as starting raw materials, to produce an intended compound. | CCCCCCC/C=C/C(=O)N1CCSC1 | null | null | null |
209,819 | ord_dataset-e0a818f9350b46cdb184d2ac404ede9f | null | 1990-01-01T00:06:00 | true | [Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[N:11][C:10]([O:13][CH:14]([C:16]([O:18]CC)=[O:17])[CH3:15])=[N:9]2)=[CH:4][CH:3]=1.[OH-].[K+]>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[N:11][C:10]([O:13][CH:14]([C:16]([OH:18])=[O:17])[CH3:15])=[N:9]2)=[CH:4][CH:3]=1 | CCOC(=O)C(C)Oc1ncn(-c2ccc(Br)cc2)n1 | null | null | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | Ten g of the compound of Example 19 was refluxed for 10 minutes with 3.3 g of potassium hydroxide in 150 ml of ethanol, and the product was collected as described in Example 22 and recrystallized from ethanol to obtain 8.0 g of the desired product, m.p. 195°-197°. | CC(Oc1ncn(-c2ccc(Br)cc2)n1)C(=O)O | null | null | null |
1,709,107 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | Br[CH2:2][C:3]1[C:7]([O:8][CH3:9])=[N:6][N:5]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[N:4]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[F:28][C:29]([F:46])([F:45])[C:30]1[CH:35]=[C:34](B2OC(C)(C)C(C)(C)O2)[CH:33]=[CH:32][N:31]=1>O1CCCC1.O.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=... | CC1(C)OB(c2ccnc(C(F)(F)F)c2)OC1(C)C | COc1nn(-c2ccc(C(F)(F)F)cc2)nc1CBr | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=P([O-])([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 17 | To a solution of 4-(bromomethyl)-5-methoxy-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazole (i.e. the product of Step D, 0.525 g, 66 weight %, 1.0 mmol) in tetrahydrofuran/water (3:1, 4 mL total), was added tetrakis(triphenylphosphine)palladium(0) (0.059 g, 0.05 mmol), potassium phosphate tribasic (0.43 g, 2.0 mmol) and... | COc1nn(-c2ccc(C(F)(F)F)cc2)nc1Cc1ccnc(C(F)(F)F)c1 | null | null | null |
1,738,934 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([N:13]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[C:14]2[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=2)[C:17]([OH:19])=O)[C:5]2[N:6]([C:8]([C:11]#[N:12])=[CH:9][N:10]=2)[N:7]=1.[CH3:32][N:33]([CH3:37])[CH2:34][CH2:35][NH2:36].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C... | CN(C)CCN | COc1ccc(CN(c2cccc(C(=O)O)c2)c2cc(Cl)nn3c(C#N)cnc23)cc1 | null | CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 25 | 1 | A stirred solution of 253C (55 mg, 0.127 mmol) in DMF (1.0 mL) was treated with N1,N1-dimethylethane-1,2-diamine (0.021 mL, 0.190 mmol), BOP (72.9 mg, 0.165 mmol) and TEA (0.035 mL, 0.254 mmol), and the reaction mixture was stirred at ambient temperature for 1 hour. The reaction mixture was concentrated, triturated wit... | COc1ccc(CN(c2cccc(C(=O)NCCN(C)C)c2)c2cc(Cl)nn3c(C#N)cnc23)cc1 | null | 93.7 | null |
1,555,618 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | B([C:4]1[S:8][C:7]([C:9]([OH:11])=[O:10])=[CH:6][CH:5]=1)(O)O.Br[C:13]1[N:17]2[N:18]=[C:19]([NH:22][CH2:23][CH2:24][CH2:25][N:26]3[CH2:30][CH2:29][CH2:28][C:27]3=[O:31])[CH:20]=[CH:21][C:16]2=[N:15][CH:14]=1>>[O:31]=[C:27]1[CH2:28][CH2:29][CH2:30][N:26]1[CH2:25][CH2:24][CH2:23][NH:22][C:19]1[CH:20]=[CH:21][C:16]2[N:17]... | O=C1CCCN1CCCNc1ccc2ncc(Br)n2n1 | O=C(O)c1ccc(B(O)O)s1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The Suzuki coupling of 5-boronothiophene-2-carboxylic acid and 1-(3-((3-bromoimidazo[1,2-b]pyridazin-6-yl)amino)propyl)pyrrolidin-2-one using the procedure described in example 5.6.19 yielded 64% of the titled compound. | O=C(O)c1ccc(-c2cnc3ccc(NCCCN4CCCC4=O)nn23)s1 | null | 64 | null |
1,556,317 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | [C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([S:20][C:21]3[C:30]4[C:25](=[CH:26][C:27]([O:35][CH3:36])=[C:28]([O:31][CH2:32][CH2:33]Cl)[CH:29]=4)[N:24]=[CH:23][N:22]=3)[CH:15]=2)=[O:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH:37]1[CH2:42][CH2:41][S:40](=[O:44])(=[O:43])[CH2:39][... | COc1cc2ncnc(Sc3cccc(NC(=O)Nc4cc(C(C)(C)C)on4)c3)c2cc1OCCCl | O=S1(=O)CCNCC1 | null | CCCC[N+](CCCC)(CCCC)CCCC | [I-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared as described in Example 57B by using 1-(5-tert-butylisoxazol-3-yl)-3-(3-(6-(2-chloroethoxy)-7-methoxyquinazolin-4-ylthio)phenyl)urea from Example 65A (200 mg, 0.38 mmol), thiomorpholine 1,1-dioxide (154 mg, 1.14 mmol), tetrabutylammonium iodide (140 mg, 0.38 mmol) and N,N′-diisopropyleth... | COc1cc2ncnc(Sc3cccc(NC(=O)Nc4cc(C(C)(C)C)on4)c3)c2cc1OCCN1CCS(=O)(=O)CC1 | null | 23.6 | null |
1,548,664 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | [NH2:1][C:2]1[C:11]([C:12]([O:14]N2C3C=CC=CC=3N=N2)=O)=[C:5]2[N:6]=[CH:7][C:8]([F:10])=[CH:9][N:4]2[N:3]=1.[CH3:24][N:25]1[CH2:30][CH2:29][CH2:28][C@@H:27]([O:31][C:32]2[C:37]([NH2:38])=[CH:36][N:35]=[CH:34][N:33]=2)[CH2:26]1>CN1C(=O)CCC1>[NH2:1][C:2]1[C:11]([C:12]([NH:38][C:37]2[C:32]([O:31][C@@H:27]3[CH2:28][CH2:29][... | Nc1nn2cc(F)cnc2c1C(=O)On1nnc2ccccc21 | CN1CCC[C@@H](Oc2ncncc2N)C1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN1CCCC1=O | null | null | null | null | null | null | null | null | null | null | 25 | null | A solution of benzotriazol-1-yl 2-amino-6-fluoro-pyrazolo[1,5-a]pyrimidine-3-carboxylate 6a (125 mg, 0.3990 mmol) and 4-[[(3R)-1-methyl-3-piperidyl]oxy]pyrimidin-5-amine 7a (83.10 mg, 0.3990 mmol) in NMP (2 mL) was heated at 100° C. overnight. The reaction mixture was cooled to RT, passed through a SCX cartridge, eluti... | CN1CCC[C@@H](Oc2ncncc2NC(=O)c2c(N)nn3cc(F)cnc23)C1 | null | null | null |
1,556,029 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | [Br:1][C:2]1[CH:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)[C:5]([NH2:17])=[CH:4][CH:3]=1.[CH:18](O)=O>C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:17]=[CH:18][N:8]([CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=3)[C:6]=2[CH:7]=1 | Nc1ccc(Br)cc1NCc1cccc(F)c1 | O=CO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of Example 2B (299 mg, 1.013 mmol) in formic acid (500 μL, 13.25 mmol) was stirred at 90° C. for 1 hour. The cooled mixture was diluted with ethyl acetate, washed with water and brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel flash chromatography (Isco®, Redi-Sep® co... | Fc1cccc(Cn2cnc3ccc(Br)cc32)c1 | null | null | null |
290,707 | ord_dataset-5fb693db3950403e9ce1a516570153bf | null | 1994-01-01T00:05:00 | true | [F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([NH:9][CH:10]=[C:11]([C:16]([O:18][CH3:19])=[O:17])[C:12]([O:14][CH3:15])=[O:13])[C:3]=1[O:20][CH2:21][CH:22]([OH:24])[CH3:23].[C:25]1([CH3:35])[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1.C(OCC)(=O)C>N1C=CC=CC=1>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]... | Cc1ccc(S(=O)(=O)Cl)cc1 | COC(=O)C(=CNc1ccc(F)c(F)c1OCC(C)O)C(=O)OC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 5 | 72 | To a solution of 2.07 g of the compound obtained in Example 6 in 4.2 ml of pyridine was added 1.49 g of p-toluenesulfonyl chloride and the mixture was stirred at an external temperature of 5° C. for 3 days. To the mixture was added ethyl acetate, and the solution was washed successively with 1 N hydrochloric acid, a sa... | COC(=O)C(=CNc1ccc(F)c(F)c1OCC(C)OS(=O)(=O)c1ccc(C)cc1)C(=O)OC | null | 92.2 | null |
154,770 | ord_dataset-d1c545e3afc447099315419421478aab | null | 1987-01-01T00:03:00 | true | [CH:1]([C:4]1([CH3:21])[C:19](=[O:20])[N:7]2[C:8](=[O:18])[C:9]3[CH:10]=[C:11]4[CH:17]=[CH:16][O:15][C:12]4=[N:13][C:14]=3[C:6]2=[N:5]1)([CH3:3])[CH3:2].C[O-].[Na+].[C:25](O)(=[O:27])C>CO>[CH:1]([C:4]1([CH3:21])[C:19](=[O:20])[NH:7][C:6]([C:14]2[N:13]=[C:12]3[O:15][CH:16]=[CH:17][C:11]3=[CH:10][C:9]=2[C:8]([O:27][CH3:2... | CC(=O)O | CC(C)C1(C)N=C2c3nc4occc4cc3C(=O)N2C1=O | null | C[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | 72 | The compound prepared in Example 40 (10.5 g, 0.037 mol) is suspended in 150 mL absolute methanol and 4.0 g sodium methoxide is added. After stirring for 72 hours at room temperature the mixture is poured onto ice containing acetic acid to maintain the pH at 3-4. A white solid forms and is filtered yielding 9.8 g (84%) ... | COC(=O)c1cc2ccoc2nc1C1=NC(C)(C(C)C)C(=O)N1 | null | 84 | null |
267,301 | ord_dataset-134cf2fa32ab464880d75db06c38f35a | null | 1993-01-01T00:05:00 | true | C[O:2][C:3]1[CH:19]=[CH:18][C:6]2[NH:7][C:8]3[CH:15]=[CH:14][C:13]([O:16]C)=[CH:12][C:9]=3[CH2:10][CH2:11][C:5]=2[CH:4]=1.B(Br)(Br)Br.O.[K+].[Br-]>CN(C)C=O>[OH:2][C:3]1[CH:19]=[CH:18][C:6]2[N:7]=[C:8]3[CH:15]=[CH:14][C:13](=[O:16])[CH:12]=[C:9]3[CH2:10][CH2:11][C:5]=2[CH:4]=1 | COc1ccc2c(c1)CCc1cc(OC)ccc1N2 | null | null | BrB(Br)Br | [Br-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 0 | 3.75 | A solution of 2,8-dimethoxy-10,11-dihydro-5H-dibenz[b,f]azepine (7) (1.0 g; 3.9 mmol) in CH2Cl2 (23.5 mL; dried over molecular sieve 4A), maintained under a CaSO4 drying tube, was cooled to 0° C. and treated with BBr3 (1.85 mL; 19.6 mmol; 5 eq). After 5 minutes the reaction was warmed and allowed to stir at ambient tem... | O=C1C=CC2=Nc3ccc(O)cc3CCC2=C1 | null | null | null |
999,591 | ord_dataset-70899a0178cc441482746c093624afa0 | null | 2010-01-01T00:10:00 | true | Br[C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C... | CC(C)(C)OC(=O)N1CCN(c2ccc(Br)cn2)CC1 | OB(O)c1ccccc1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | CCO | null | null | null | null | null | null | null | null | null | null | null | A mixed solution of tert-butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate (1.00 g, 2.92 mmol), phenylboronic acid (535 mg, 4.38 mmol), ethanol (2.5 ml), 2N aqueous solution of sodium carbonate (12 ml), tetrakis(triphenylphosphine)palladium (404 mg, 0.350 mmol) and toluene (23 ml) was stirred at 95° C. for 12 hours... | CC(C)(C)OC(=O)N1CCN(c2ccc(-c3ccccc3)cn2)CC1 | null | 80.7 | null |
1,472,839 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | [NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]=[C:13]([Br:15])[CH:12]=[C:11]([C:16]([NH2:18])=[O:17])[C:7]=3[NH:8][C:9]=2[CH:10]=1.[Cl:19][CH2:20][CH2:21][O:22][CH2:23][C:24](Cl)=[O:25]>C1(C)C=CC=CC=1>[Br:15][C:13]1[CH:12]=[C:11]([C:16]([NH2:18])=[O:17])[C:7]2[NH:8][C:9]3[CH:10]=[C:2]([NH:1][C:24](=[O:25])[CH2:23][O:22][... | O=C(Cl)COCCCl | NC(=O)c1cc(Br)nc2c1[nH]c1cc(N)ccc12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | 100 | 12 | A mixture of 7-amino-2-bromo-5H-pyrido[3,2-b]indole-4-carboxamide (200 mg, 0.655 mmol) and 2-(2-chloroethoxy)acetyl chloride (113 mg, 0.721 mmol) in toluene (1.5 mL) was stirred at 100° C. for 12 hr. The solvent was removed and preparative HPLC (100×30 mm Luna C18 column, Solvent A=10% Methanol, 90% H2O, 0.1% TFA; Solv... | NC(=O)c1cc(Br)nc2c1[nH]c1cc(NC(=O)COCCCl)ccc12 | null | 29 | null |
1,052,694 | ord_dataset-373415d3e0e54004837cf4831e67666f | null | 2011-01-01T00:05:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:16][C@H:17]2[CH2:21][CH2:20][C:19]([F:23])([F:22])[CH2:18]2)[C:13](O)=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].C(Cl)(=O)C([Cl:27])=O>C(Cl)Cl.CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:16][C@H:17]2[CH2:21][CH2:20][C:19]([F:23])([F:22])[CH2:18]2)[C:13]([Cl:27])=[... | CS(=O)(=O)c1ccc(C(C[C@H]2CCC(F)(F)C2)C(=O)O)cc1Cl | O=C(Cl)C(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | ClCCl | null | null | null | null | null | null | null | null | null | 0 | 0.25 | A solution of 2-(3-chloro-4-methanesulfonyl-phenyl)-3-((R)-3,3-difluoro-cyclopentyl)-propionic acid (240 mg, 0.65 mmol) was dissolved in methylene chloride (10 mL) and N,N-dimethylformamide (one drop) and cooled to 0° C. To this solution was added dropwise a solution of oxalyl chloride in methylene chloride (2 M soluti... | CS(=O)(=O)c1ccc(C(C[C@H]2CCC(F)(F)C2)C(=O)Cl)cc1Cl | null | null | null |
1,744,918 | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | null | 2016-01-01T00:07:00 | true | [Br:1][C:2]1[N:3]=[C:4]([NH2:7])[S:5][CH:6]=1.[C:8](OC(=O)C)(=[O:10])[CH3:9]>C(O)(=O)C>[Br:1][C:2]1[N:3]=[C:4]([NH:7][C:8](=[O:10])[CH3:9])[S:5][CH:6]=1 | CC(=O)OC(C)=O | Nc1nc(Br)cs1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | 25 | null | A solution of 4-bromothiazol-2-amine (0.500 g, 2.81 mmol), acetic anhydride (0.43 mL, 4.50 mmol) and acetic acid (5 mL) was refluxed for 2 h. The reaction mixture was cooled to room temperature and concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with 25% ethyl acetat... | CC(=O)Nc1nc(Br)cs1 | null | 48.3 | null |
1,752,568 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | [CH3:1][C:2]1[N:7]2[CH:8]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.[Br:16]N1C(=O)CCC1=O>C(#N)C>[Br:16][C:8]1[N:7]2[C:2]([CH3:1])=[CH:3][CH:4]=[CH:5][C:6]2=[N:10][C:9]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12] | O=C1CCC(=O)N1Br | CCOC(=O)c1cn2c(C)cccc2n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | 20 | 0.5 | A solution of ethyl 5-methylimidazo[1,2-a]pyridine-2-carboxylate (5.0 g, 25 mmol) in acetonitrile (94 mL) was treated with N-bromosuccinimide (4.8 g, 27 mmol) in acetonitrile (47 mL) dropwise and stirred at 20° C. for 30 min. The reaction mixture was concentrated, diluted with dichloromethane (200 mL), and washed with ... | CCOC(=O)c1nc2cccc(C)n2c1Br | null | 56.5 | null |
1,497,029 | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | null | 2014-01-01T00:10:00 | true | Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[NH:12][CH:13]=[C:14]([C:16]#[N:17])[N:15]=2)=[O:10])=[C:4]([C:18]2[CH2:23][CH2:22][C:21]([CH3:25])([CH3:24])[CH2:20][CH:19]=2)[CH:3]=1.[CH3:26][C:27]12[O:34][C:31]([CH3:35])([CH2:32][CH2:33]1)[CH2:30][C:29](=[O:36])[CH2:28]2>>[CH3:24][C:21]1([CH3:25])[CH2:22][CH2:23][C:18]... | CC12CCC(C)(CC(=O)C1)O2 | CC1(C)CC=C(c2cc(Br)ccc2NC(=O)c2nc(C#N)c[nH]2)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared as described in Example 1, step (h) using 4-cyano-1H-imidazole-2-carboxylic acid [4-bromo-2-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-amide (as prepared in Example 1, step (g)) and 1,5-dimethyl-8-oxa-bicyclo[3.2.1]octan-3-one (J. Org. Chem., 64(10), 3398-3408 (1999)). 1H-NMR (DMSO-d6; 400 M... | CC1(C)CC=C(c2cc(C3(O)CC4(C)CCC(C)(C3)O4)ccc2NC(=O)c2nc(C#N)c[nH]2)CC1 | null | null | null |
1,631,278 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | [CH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[NH2:11].[C:12]([CH:15]([CH2:20][C:21]([O:23][CH3:24])=[O:22])[C:16]([O:18][CH3:19])=[O:17])(=O)[CH3:13]>>[CH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[NH:11][C:12](=[C:15]([CH2:20][C:21]([O:23][CH3:24])=[O:22])[C:16]([O:18][CH... | COC(=O)CC(C(C)=O)C(=O)OC | Nc1ccc2c(c1)CCCC2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 72 | The 5,6,7,8-tetrahydronaphthalen-2-amine (10 g; 68 mmol) and dimethyl acetylsuccinate (11.6 g; 62 mmol) were mixed together, placed in a dessicator and the homogeneous mixture was stirred under vacuum (3 mbars) for 3 days. Purification by flash chromatography on silica gel using a gradient of ethyl acetate (1 to 20%) i... | COC(=O)CC(C(=O)OC)=C(C)Nc1ccc2c(c1)CCCC2 | null | 65.6 | null |
910,167 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | Cl.C([NH:5][C:6]([CH2:17][C:18]1[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[C:21]([NH2:28])=[C:20]([Cl:29])[CH:19]=1)(C(OCC)=O)[C:7]([O:9]CC)=[O:8])(=O)C>CC(O)=O.O>[ClH:29].[NH2:5][CH:6]([CH2:17][C:18]1[CH:23]=[C:22]([C:24]([F:26])([F:27])[F:25])[C:21]([NH2:28])=[C:20]([Cl:29])[CH:19]=1)[C:7]([OH:9])=[O:8] | CCOC(=O)C(Cc1cc(Cl)c(N)c(C(F)(F)F)c1)(NC(C)=O)C(=O)OCC | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC(=O)O | null | null | null | null | null | null | null | null | null | 140 | 0.25 | 50 mL conc. HCl were added to a solution of 40.0 g (94.16 mmol) of diethyl 2-acetylamino-2-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-malonate in 110 mL AcOH and 150 mL of water and the reaction mixture was heated to 140° C. for 4 h. The precipitate formed was filtered off and discarded. The filtrate was evaporated do... | Nc1c(Cl)cc(CC(N)C(=O)O)cc1C(F)(F)F | null | null | null |
7,777 | ord_dataset-653be8036d754ce7b8a1c4cd419eaf55 | null | 1976-01-01T00:05:00 | true | C1([N:7]2[CH2:12][CH2:11][C:10]3([C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH2:14][O:13]3)[CH2:9][CH2:8]2)C=CC=CC=1.Cl>[Pd].C(O)C>[C:15]1([CH:14]2[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:10]3([CH2:9][CH2:8][NH:7][CH2:12][CH2:11]3)[O:13]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1 | c1ccc(N2CCC3(CC2)OCc2ccccc23)cc1 | null | null | [Pd] | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 2.9 G. of 1'-benzyl-1,3-dihydro-3-phenylspiro[phenylspiro[isobenzofuran-1,4'-piperidine], (Example 4), 0.4 g. of 10% palladium on carbon, 20 ml. of 95% ethanol, and 2 ml. of conc. hydrochloric acid is hydrogenated at 50 p.s.i. and 50°. After hydrogen uptake ceases, the mixture is filtered and the filtrate ... | c1ccc(C2OC3(CCNCC3)c3ccccc32)cc1 | null | null | null |
1,182,099 | ord_dataset-9cd817a75dfc4fe7ad19d4232772d5ff | null | 2012-01-01T00:07:00 | true | [F:1][C:2]1[C:10]([O:11][C:12]2[C:21]3[C:16](=[CH:17][C:18]([O:24][CH2:25][CH2:26][N:27]4[CH2:33][C:32](=[O:34])[C:29]5([CH2:31][CH2:30]5)[CH2:28]4)=[C:19]([O:22][CH3:23])[CH:20]=3)[N:15]=[CH:14][CH:13]=2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:35])[NH:6]2.[H-].[Na+].S(OC)([C:41]1C=CC(C)=CC=1)(=O)=O>CN(C=O)C>[F:1]... | COS(=O)(=O)c1ccc(C)cc1 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3F)ccnc2cc1OCCN1CC(=O)C2(CC2)C1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 0 | 0.17 | The above product from Example 2 (60 mg) was dissolved into DMF (4 ml) and cooled at 0° C. NaH (1.1 eq) was added to the reaction and stirred for 10 minutes. To the reaction was added TsOMe (1.2 eq), the solution was heated at 80° C. for two hours. The reaction was quenched with water and extracted with EtOAc followed ... | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3F)ccnc2cc1OCCN1CC(OC)C2(CC2)C1 | null | null | null |
46,285 | ord_dataset-becaf7dc22c44672b22e4b94335cbf08 | null | 1978-01-01T00:09:00 | true | [NH:1]([C:3]1[CH2:9][N:8]=[C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:6]2[CH:16]=[C:17]([C:20]([F:23])([F:22])[F:21])[CH:18]=[CH:19][C:5]=2[N:4]=1)[NH2:2].[C:24]([O-])([O-])(OCC)[CH3:25].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[CH3:24][C:25]1[N:4]2[C:5]3[CH:19]=[CH:18][C:17]([C:20]([F:23])... | NNC1=Nc2ccc(C(F)(F)F)cc2C(c2ccccc2)=NC1 | CCOC(C)([O-])[O-] | null | Cc1ccc(S(=O)(=O)O)cc1 | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | To a mixture of 9,5 parts of 2-hydrazino-5-phenyl-7-trifluoromethyl-3-H-1,4-benzodiazepine prepared in Example 4, 29 parts of ethyl orthoacetate and 150 parts by volume of chloroform, is added dropwise 23 parts of p-toluenesulfonic acid with stirring under ice-cooling below 10° C and then the mixture is stirred at room... | Cc1nnc2n1-c1ccc(C(F)(F)F)cc1C(c1ccccc1)=NC2 | null | null | null |
1,397,154 | ord_dataset-12dc3bd21bcf44d09e5b4249afe15161 | null | 2014-01-01T00:02:00 | true | [Cl:1][CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=1[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=O>CC(O)=O>[Cl:1][CH2:2][C:3]1[N:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:7]2[CH:8]=[C:9]([F:12])[CH:10]=[CH:11][C:6]=2[N:5]=1 | O=C(CCl)Nc1ccc(F)cc1Nc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | 70 | null | 2-Chloro-N-(4-fluoro-2-phenylaminophenyl)acetamide (740 mg, 2.62 mmol) was dissolved in AcOH (20 mL) and the mixture heated at 70° C. under a nitrogen atmosphere for 5 h. The volatiles were removed in vacuo and the resulting residue partitioned between DCM and a saturated aqueous solution of NaHCO3. The aqueous phase w... | Fc1ccc2nc(CCl)n(-c3ccccc3)c2c1 | null | null | null |
654,603 | ord_dataset-fe016e2f90e741a590ad77fd5933161f | null | 2004-01-01T00:11:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.Br[CH2:24][CH2:25][C:26]([F:29])([F:28])[F:27].C(=O)([O-])O.[Na+]>CN(C)C=O>[F:27][C:26]([F:29])([F:28])[CH2:25][CH2:24][N:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][C... | CC(C)(C)OC(=O)N1CCNCC1 | FC(F)(F)CCBr | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | 60 | 4 | To a solution of 1-(tert-butoxycarbonyl)piperazine (5.00 g) and N,N-diisopropylethylamine (4.68 ml) in N,N-dimethylformamide (13 ml) was added 1-bromo-3,3,3-trifluoropropane (5.00 ml) at 60° C. The mixture was stirred at 60° C. for 4 hours. The reaction mixture was poured into saturated aqueous sodium hydrogencarbonate... | CC(C)(C)OC(=O)N1CCN(CCC(F)(F)F)CC1 | null | null | null |
382,797 | ord_dataset-f367d8d2baac490b9204609a79420961 | null | 1997-01-01T00:11:00 | true | [C:1]([O:9][C@H:10]1[CH2:34][CH2:33][C@@:32]2([CH3:35])[C@@H:12]([CH2:13][C:14](=O)[C:15]3[C@@H:31]2[CH2:30][CH2:29][C@@:28]2([CH3:36])[C:16]=3[C:17](=O)[CH2:18][C@@H:19]2[C@H:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NN>C(O)C>[C:1]([O:9][C... | CC(C)CCC[C@@H](C)[C@H]1CC(=O)C2=C3C(=O)C[C@H]4C[C@@H](OC(=O)c5ccccc5)CC[C@]4(C)[C@H]3CC[C@@]21C | null | null | NN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 90 | null | To 3β-benzoyloxy-5α-cholest-8(14)-ene-7,15-dione 10 (180 mg, 0.35 mmol) dissolved in ethanol (14 mL) was added anhydrous hydrazine (12 μl, 0.38 mmol) and the mixture was heated to 90° C. for 0.75 h. The solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography on 4 g of s... | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](OC(=O)c5ccccc5)CC[C@]4(C)[C@H]3CC[C@]12C | null | 73.6 | null |
1,384,538 | ord_dataset-31641fb65b34430fa7435229b949b604 | null | 2014-01-01T00:01:00 | true | [NH2:1][N:2]1[N:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:16].[CH3:17][C:18]1[S:22][C:21]([CH2:23][C:24](O)=[O:25])=[CH:20][CH:19]=1>>[CH3:17][C:18]1[S:22][C:21]([CH2:23][C:24]([NH:1][N:2]2[N:11]=[C:10]([C:12]([F:15])([F:13])[F:14])[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=... | Nn1nc(C(F)(F)F)c2ccccc2c1=O | Cc1ccc(CC(=O)O)s1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The product of Example 11B and 2-(5-methylthiophen-2-yl)acetic acid were treated using a method similar to that described in Example 5 to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 11.85-11.96 (m, 1H), 8.43 (d, J=6.9 Hz, 1H), 8.10-8.17 (m, 1H), 8.01-8.08 (m, 2H), 6.81 (d, J=3.4 Hz, 1H), 6.66-6.68 (m, 1H),... | Cc1ccc(CC(=O)Nn2nc(C(F)(F)F)c3ccccc3c2=O)s1 | null | null | null |
905,989 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | C([O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[C:11]([O:19][CH3:20])[CH:10]=1)C1C=CC=CC=1>CO.[Pd]>[CH3:18][S:15]([C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][C:11]=1[O:19][CH3:20])(=[O:16])=[O:17] | COc1cc(OCc2ccccc2)ccc1S(C)(=O)=O | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | 3 | Dissolve 4-benzyloxy-1-methanesulfonyl-2-methoxy-benzene (5.57 g, 19.09 mmol) in MeOH (200 mL), under N2, and add 5% Pd—C (900 mg). Evacuate the reaction vessel and flush with hydrogen gas (3 times). Stir the reaction mixture at room temperature for 3 hours, under 1 atmosphere of hydrogen gas. Filter, concentrate, and ... | COc1cc(O)ccc1S(C)(=O)=O | null | 83.9 | null |
1,244,879 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | [CH3:1][N:2]1[C:6]([C:7](=[O:23])[NH:8][C:9]2[CH:14]=[CH:13][N:12]3[N:15]=[C:16]([N:18]4[CH2:22][CH2:21][CH2:20][CH2:19]4)[N:17]=[C:11]3[CH:10]=2)=[C:5]([C:24](O)=[O:25])[CH:4]=[N:3]1.[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.CCCP(=O)=O.C(N(CC)C(C)C)(C)C>O1CCCC1>[N:18]1([C:16]2[N:17]=[C:11]3[CH:10]=[C:9]([NH:8][C... | Cn1ncc(C(=O)O)c1C(=O)Nc1ccn2nc(N3CCCC3)nc2c1 | C1COCCN1 | null | CCCP(=O)=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | 70 | 18 | A mixture of 1-methyl-5-(2-(pyrrolidin-1-yl)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid (150 mg, 422 μmol), morpholine (368 μl, 4.22 mmol), propylphosphonic anhydride (50% in ethyl acetate, 622 μl, 1.06 mmol) and N,N-diisopropylethylamine (215 μl, 1.27 mmol) in tetrahydrofuran (6 ml) was... | Cn1ncc(C(=O)N2CCOCC2)c1C(=O)Nc1ccn2nc(N3CCCC3)nc2c1 | null | 60.9 | null |
1,488,721 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]2[C:23]([NH2:24])=[CH:22][N:21]=[CH:20][N:19]=2)=[CH:13][CH:12]=1.[C:25](=O)(ON1C(=O)CCC1=O)[O:26]N1C(=O)CCC1=O>CN(C=O)C.O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]1[CH:16]=[CH:15][C:14... | O=C(ON1C(=O)CCC1=O)ON1C(=O)CCC1=O | Nc1cncnc1Nc1ccc(Nc2nc3ccccc3o2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 80 | 8 | A mixture of N4-[4-(1,3-benzoxazol-2-ylamino)phenyl]pyrimidine-4,5-diamine (55 mg) and bis(2,5-dioxopyrrolidin-1-yl) carbonate (53 mg) in DMF (5 mL) was stirred overnight at 80° C. then at 95° C. for 3 h. After this time, the reaction mixture was cooled to ambient temperature, diluted with water (50 mL) and extracted w... | O=c1[nH]c2cncnc2n1-c1ccc(Nc2nc3ccccc3o2)cc1 | null | 31.9 | null |
645,788 | ord_dataset-c975a50a7600448fabd558f4a94a3e29 | null | 2004-01-01T00:08:00 | true | [N+:1]([O-:4])([O-])=[O:2].[Na+].[Br:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][CH:8]=1>S(=O)(=O)(O)O>[Br:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][C:8]=1[N+:1]([O-:4])=[O:2] | O=Cc1ccc(Br)cc1 | O=[N+]([O-])[O-] | null | O=S(=O)(O)O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 10 | null | A suspension of sodium nitrate (1.37 g, 16.2 mmol) in concentrated sulfuric acid(15 mL) was stirred at 10° C. until a homogeneous solution was obtained. The solution was treated with 4-bromobenzaldehyde (2.50 g, 13.5 mmol) in portionwise fashion over a 20 minute period. The mixture was poured onto ice (50 g) and the re... | O=Cc1ccc(Br)c([N+](=O)[O-])c1 | null | 94.8 | null |
1,479,531 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[CH3:15][NH:16][CH3:17].[H-].[Na+].O>O1CCCC1>[CH3:15][N:16]([CH3:17])[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12] | O=[N+]([O-])c1ccc(F)c(C(F)(F)F)c1 | CNC | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | O | null | null | null | null | null | null | null | null | null | 50 | 16 | To a solution of 1-floro-4-nitro-2-trifluoromethylbenzene (2.0 g) in tetrahydrofuran (20 mL) were added dimethyamine (0.64 g) and sodium hydride (0.34 g) at room temperature, and this mixture was stirred at 50° C. for 16 hours. This reaction mixture was poured into water, and this mixture was extracted with ethyl aceta... | CN(C)c1ccc([N+](=O)[O-])cc1C(F)(F)F | null | 42 | null |
230,940 | ord_dataset-67c9ee844bf341888b345c8e36183b40 | null | 1991-01-01T00:07:00 | true | [CH2:1]([O:8][C:9](=[O:52])[CH:10]([CH2:36][CH2:37][C:38](=[O:51])[NH:39]CC1C=CC(OC)=CC=1OC)[CH2:11][C:12]1([C:17](=[O:35])[NH:18][C@H:19]2[CH2:24][CH2:23][C@@H:22]([C:25]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:26])[CH2:21][CH2:20]2)[CH2:16][CH2:15][CH2:14][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[... | COc1ccc(CNC(=O)CCC(CC2(C(=O)N[C@H]3CC[C@@H](C(=O)OCc4ccccc4)CC3)CCCC2)C(=O)OCc2ccccc2)c(OC)c1 | null | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | O | null | null | null | null | null | null | null | null | null | 25 | 18 | 3-{1-[(cis-4-Benzyloxycarbonyl-cyclohexyl)carbamoyl]cyclopentyl}-2-{2-[(2,4-dimethoxyphenyl)methylcarbamoyl]ethyl}propanoic acid benzyl ester (Example 164) (0.37 g, 0.52 mmole) was dissolved in trifluoroacetic acid (10 ml). After stirring for 18 hours at room temperature the deep pink reaction mixture was poured into i... | NC(=O)CCC(CC1(C(=O)N[C@H]2CC[C@@H](C(=O)OCc3ccccc3)CC2)CCCC1)C(=O)OCc1ccccc1 | null | 37.6 | null |
1,549,541 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | [CH3:1][C:2]1[N:3]=[C:4]([C:8]2[NH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][C:11]=3[NH2:17])[S:5][C:6]=1[CH3:7].[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[S:23](Cl)(=[O:25])=[O:24]>N1C=CC=CC=1>[CH3:1][C:2]1[N:3]=[C:4]([C:8]2[NH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][C:11]=3[NH:17][S:23]([C:19]2[S:18][CH:... | O=S(=O)(Cl)c1cccs1 | Cc1nc(-c2cc3cccc(N)c3[nH]2)sc1C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | 25 | 15 | To a mixture of 2-(4,5-dimethyl-1,3-thiazol-2-yl)-1H-indole-7-amine (0.10 g) and pyridine (8 mL) was added thiophene-2-sulfonyl chloride (0.090 g) at 4° C., and the mixture was stirred at room temperature for 15 hr. The reaction solution was concentrated. The obtained residue was diluted with ethyl acetate, washed with... | Cc1nc(-c2cc3cccc(NS(=O)(=O)c4cccs4)c3[nH]2)sc1C | null | 88.7 | null |
1,601,505 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [Br:1][C:2]1[CH:3]=[C:4]([Cl:14])[C:5]2[O:9][C:8]([CH2:10][CH2:11][OH:12])=[CH:7][C:6]=2[CH:13]=1.C(N(CC)CC)C.[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>ClCCl>[CH3:32][C:22]1[CH:27]=[CH:26][C:25]([S:28]([O:12][CH2:11][CH2:10][C:8]2[O:9][C:5]3[C:4]([Cl:14])=[CH:3][C:2]([Br:1])=[C... | OCCc1cc2cc(Br)cc(Cl)c2o1 | Cc1ccc(S(=O)(=O)Cl)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 25 | 12 | To a solution of the product of step B (3.5 g, 12.7 mmol) in dichloromethane (30 mL) was added triethylamine (3.7 mL, 25.4 mmol) followed by p-toluenesulfonyl chloride (3.6 mL, 19.05 mmol) at 0° C. The reaction mixture was stirred at ambient temperature for 12 h and concentrated in vacuo. The reaction mixture was quenc... | Cc1ccc(S(=O)(=O)OCCc2cc3cc(Br)cc(Cl)c3o2)cc1 | null | 93.5 | null |
1,456,710 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [NH2:1][CH2:2][CH2:3][OH:4].[F:5][C:6]1[CH:7]=[C:8]([C:22]2[N:23]=[C:24]([N:36]3[CH2:41][CH2:40][O:39][CH2:38][C@@H:37]3[CH3:42])[C:25]3[CH2:30][N:29]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:28][C:26]=3[N:27]=2)[CH:9]=[CH:10][C:11]=1[NH:12][C:13](OC1C=CC=CC=1)=[O:14]>>[CH2:34]([O:33][C:31]([N:29]1[CH2:30][C:25]2[C:2... | NCCO | CCOC(=O)N1Cc2nc(-c3ccc(NC(=O)Oc4ccccc4)c(F)c3)nc(N3CCOC[C@@H]3C)c2C1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Method as described for example 51, using 2-aminoethanol and (S)-ethyl 2-(3-fluoro-4-((phenoxycarbonyl)amino)phenyl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate as starting materials. The mixture was reduced in vacuo and purified by flash SCX2 chromatography affording the title compound (10 mg,... | CCOC(=O)N1Cc2nc(-c3ccc(NC(=O)NCCO)c(F)c3)nc(N3CCOC[C@@H]3C)c2C1 | null | 36 | null |
1,257,971 | ord_dataset-266f60b4555945d6afb2d2bdf5fa04e0 | null | 2013-01-01T00:02:00 | true | Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]([F:15])[C:9]2[N:10]=[N:11][N:12]([CH3:14])[CH:13]=2)[N:3]=1.[NH2:16][C:17]1[S:18][C:19]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([OH:34])([CH3:33])[CH3:32])=[CH:27][C:26]=2[F:35])=[CH:20][C:21]=1[C:22]([NH2:24])=[O:23]>>[F:35][C:26]1[CH:27]=[C:28]([C:31]([OH:34])([CH3:32])[CH3:33])[C... | Cn1cc(C(F)c2cccc(Br)n2)nn1 | CC(C)(O)c1ccc(-c2cc(C(N)=O)c(N)s2)c(F)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was synthesized from 2-bromo-6-[fluoro(1-methyl-1H-1,2,3-triazol-4-yl)methyl]pyridine (111 mg, 0.41 mmol) and 2-amino-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide (120 mg, 0.41 mmol) according to the general procedure in Example 1. | Cn1cc(C(F)c2cccc(Nc3sc(-c4ccc(C(C)(C)O)cc4F)cc3C(N)=O)n2)nn1 | null | null | null |
642,336 | ord_dataset-ce71a906ea9c4399a2014cbaaff88c8f | null | 2004-01-01T00:07:00 | true | [CH3:1][N:2]([CH3:18])[CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:7]=1[N+:15]([O-:17])=[O:16].[C:19](Cl)(=[O:21])[CH3:20]>>[CH3:1][N:2]([CH3:18])[CH2:3][CH2:4][N:5]([C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:7]=1[N+:15]([O-:17])=[O:16])[C:19](=[O:21])[CH3:20] | CN(C)CCNc1ccc([N+](=O)[O-])cc1[N+](=O)[O-] | CC(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared from 4-(2-dimethylamino-ethyl-amino)-1,3-dinitrobenzene and acetyl chloride | CC(=O)N(CCN(C)C)c1ccc([N+](=O)[O-])cc1[N+](=O)[O-] | null | null | null |
1,381,642 | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | null | 2013-01-01T00:12:00 | true | [C:1]([CH:3]1[CH2:5][CH2:4]1)#[CH:2].[N+:6]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])([O-])=[O:7].C1N2CCN(CC2)C1>C(O)C>[CH:3]1([C:1]2[O:7][N:6]=[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:2]=2)[CH2:5][CH2:4]1 | C#CC1CC1 | CCOC(=O)C[N+](=O)[O-] | null | C1CN2CCN1CC2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | A solution of ethynylcyclopropane (0.40 mL; 4.58 mmol), ethyl 2-nitroacetate (1.30 mL; 11.46 mmol), and 1,4-diazobicyclo[2.2.2]octane (DABCO, 0.053 g; 0.458 mmol) in ethanol (3 mL) was irradiated in a microwave oven at 150° C. for 20 min and was then evaporated. The residue was dissolved in ethyl acetate and the soluti... | CCOC(=O)c1cc(C2CC2)on1 | null | 92.2 | null |
1,104,360 | ord_dataset-375a420ee9b042918ddca20f02df37d3 | null | 2011-01-01T00:11:00 | true | [C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[C:7]([NH2:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[N:13]([C:16]1[C:17]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=2)=[N:18][CH:19]=[CH:20][CH:21]=1)=[C:14]=S>ClCCCl>[C:1]([C:5]1[CH:10]=[CH:9][C:8]2[N:11]=[C:14]([NH:13][C:16]3[C:17]([O:22][C:... | CC(C)(C)c1ccc(N)c(N)c1 | FC(F)(F)c1cccc(Oc2ncccc2N=C=S)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCCl | null | null | null | null | null | null | null | null | null | null | 25 | 18 | To a solution of 4-(tert-butyl)-1,2-diaminobenzene (20 mg, 0.12 mmol) in DCE (1 mL) was slowly added 3c (19 mg, 0.06 mmol). The reaction was stirred 18 h at rt and concentrated. The crude mixture containing 3d and 3d′ was used in the next step without further purification. | CC(C)(C)c1ccc2nc(Nc3cccnc3Oc3cccc(C(F)(F)F)c3)[nH]c2c1 | null | null | null |
770,959 | ord_dataset-8214eb8444a44dc2900ccb42dbeff15e | null | 2007-01-01T00:05:00 | true | [Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[F:9].[N+:10]([O-])([O-:12])=[O:11].[K+]>OS(O)(=O)=O>[Br:1][C:2]1[CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]([CH3:8])=[CH:4][C:3]=1[F:9] | Cc1ccc(Br)c(F)c1 | O=[N+]([O-])[O-] | null | O=S(=O)(O)O | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 25 | 8 | To a stirred solution of 4-bromo-3-fluorotoluene (10 g, 52.9 mmol) in H2SO4 (100 mL) was added KNO3 (5.34 g, 52.9 mmol) at 0° C. After stirring overnight at room temperature, the reaction mixture was poured into ice (200 g) and extracted with EtOAc (3×300 mL). The organic solution was washed with brine (200 mL), dried ... | Cc1cc(F)c(Br)cc1[N+](=O)[O-] | null | 99.8 | null |
88,260 | ord_dataset-6dbd68e494f94ae796187f53698183da | null | 1981-01-01T00:11:00 | true | [NH:1]([C:29]([O:31]CC1C=CC=CC=1)=O)[C@H:2]([C:8]([NH:10][C@H:11]([C:18]([N:20]1[CH2:28][CH2:27][CH2:26][CH2:25][C@H:21]1[C:22]([NH2:24])=[O:23])=[O:19])[CH2:12][C:13]1[N:17]=[CH:16][NH:15][CH:14]=1)=[O:9])[CH2:3][CH2:4]C(=O)N>C(O)(=O)C.[Pd]>[NH:1]1[C:29](=[O:31])[CH2:4][CH2:3][C@H:2]1[C:8]([NH:10][C@H:11]([C:18]([N:20... | NC(=O)CC[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@@H](Cc1c[nH]cn1)C(=O)N1CCCC[C@H]1C(N)=O | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | 2.1 g (4 mmoles) of Z-Gln-His-HPro-NH2 are dissolved in 40 ml of acetic acid, 0.4 g of a 10% palladium-on-carbon catalyst are added, and hydrogen is bubbled through the mixture for one hour. The catalyst is filtered off, the filtrate is heated to 60°-70° C., maintained at this temperature for 30 minutes, and then evapo... | NC(=O)[C@@H]1CCCCN1C(=O)[C@H](Cc1c[nH]cn1)NC(=O)[C@@H]1CCC(=O)N1 | null | 41 | null |
45,693 | ord_dataset-becaf7dc22c44672b22e4b94335cbf08 | null | 1978-01-01T00:09:00 | true | [N+](C(C)C)([O-])=[O:2].[Na].Br[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[O:18][N:17]=2)=[CH:12][CH:11]=1>C(O)C.CN(C)C=O>[CH:9]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[O:18][N:17]=2)=[CH:12][CH:11]=1)=[O:2] | BrCc1ccc(-c2noc3ccccc23)cc1 | CC(C)[N+](=O)[O-] | null | [Na] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCO | null | null | null | null | null | null | null | null | null | 50 | 1 | 115.8 g of 2-nitropropane are introduced at about 30° C. into a solution of 23.13 g of sodium in 2,700 ml of anhydrous ethanol. The mixture is stirred for a further one hour and a solution of 288.1 g of 3-(p-bromomethyl-phenyl)-1,2-benzisoxazole in 350 ml of dimethylformamide is now added. Subsequently, the reaction mi... | O=Cc1ccc(-c2noc3ccccc23)cc1 | null | null | null |
1,053,101 | ord_dataset-373415d3e0e54004837cf4831e67666f | null | 2011-01-01T00:05:00 | true | Cl[CH2:2][C:3]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([N:14]3[C:18](=[O:19])[C:17]([CH3:21])([CH3:20])[N:16]([CH2:22][C:23]4[CH:28]=[CH:27][N:26]=[C:25]([Cl:29])[CH:24]=4)[C:15]3=[O:30])[CH:12]=2)[C:7]([CH3:32])([CH3:31])[CH2:6]1)=[O:4].[CH3:33][NH:34][CH3:35]>O1CCCC1>[Cl:29][C:25]1[CH:24]=[C:23]([CH2:22][N:16]2[C:17... | CC1(C)CN(C(=O)CCl)c2cc(N3C(=O)N(Cc4ccnc(Cl)c4)C(C)(C)C3=O)ccc21 | CNC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 0.951 g of 3-[1-(chloroacetyl)-3,3-dimethyl-2,3-dihydro-1H-indol-6-yl]-1-[(2-chloropyridin-4-yl)methyl]-5,5-dimethylimidazolidine-2,4-dione obtained in stage j) of Example 3 in 80 mL of a 2M solution of dimethylamine in tetrahydrofuran is heated at 60° C. for 4 hours. The reaction mixture is then concentr... | CN(C)CC(=O)N1CC(C)(C)c2ccc(N3C(=O)N(Cc4ccnc(Cl)c4)C(C)(C)C3=O)cc21 | null | null | null |
124,475 | ord_dataset-6d96290c60d941d098c4ddc9d0cb01a0 | null | 1984-01-01T00:12:00 | true | O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:13]12[C:26](=[O:27])[O:25][C:23](=O)[C:14]=1[CH2:15][CH2:16][C:17]1[C:22]2=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH2:28]([NH2:31])[CH2:29][NH2:30]>C1(C)C=CC=CC=1>[NH2:30][CH2:29][CH2:28][N:31]1[C:23](=[O:25])[C:14]2[CH2:15][CH2:16][C:17]3[C:22]([C:13]=2[C:26]1=[O:27])=[CH:21][CH:20]=[CH:19][C... | NCCN | O=C1OC(=O)C2=C1CCc1ccccc12 | null | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | O | null | null | null | null | null | null | null | null | null | 60 | null | 27.6 g of toluene-p-sulphonic acid monohydrate are added to a solution of 27.62 g (0.138 mol) of 3,4-dihydronaphthalene-1,2-dicarboxylic acid anhydride in 300 ml of toluene, followed by 8.69 g of ethylenediamine. The mixture is heated to 60° C. for 30 minutes and then refluxed for 30 minutes, removing continuously the ... | NCCN1C(=O)C2=C(C1=O)c1ccccc1CC2 | null | 97.8 | null |
1,429,149 | ord_dataset-5e6956e6e8c24a168866a253f4a66c6c | null | 2014-01-01T00:05:00 | true | C1(S([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([Cl:19])[CH:18]=[C:13]3[C:12]([CH2:20][C:21]3[S:25][C:24]([NH:26][CH2:27][C:28]4[CH:29]=[N:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=4)=[N:23][C:22]=3[Cl:36])=[CH:11]2)(=O)=O)C=CC=CC=1.CO.[OH-].[K+]>C(O)(=O)C>[Cl:36][C:22]1[N:23]=[C:24]([NH:26][CH2:27][C:28]2[CH:29]=[N:30][C:31](... | COc1ccc(CNc2nc(Cl)c(Cc3cn(S(=O)(=O)c4ccccc4)c4ncc(Cl)cc34)s2)cn1 | null | null | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | CC(=O)O | null | null | null | null | null | null | null | null | null | 80 | null | [5-(1-Benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-4-chloro-thiazol-2-yl]-(6-methoxy-pyridin-3-ylmethyl)-amine 619 was combined with methanol: potassium hydroxide (1M) (1:1, 0.5 mL). The mixture was heated at 80° C. for 2 hours. Acetic acid (0.1 mL) was added and the solvents removed under reduced pressure. The... | COc1ccc(CNc2nc(Cl)c(Cc3c[nH]c4ncc(Cl)cc34)s2)cn1 | null | null | null |
1,526,504 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | Cl[C:2]1[N:7]2[N:8]=[C:9]([CH3:11])[CH:10]=[C:6]2[N:5]=[C:4]([NH:12][C:13](=[O:24])[C:14]2[CH:19]=[CH:18][C:17]([C:20]([OH:23])([CH3:22])[CH3:21])=[CH:16][CH:15]=2)[CH:3]=1.[O:25]1[CH2:31][CH2:30][CH2:29][O:28][C:27]2[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][C:26]1=2.O1CCOCC1>CO.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1... | OB(O)c1ccc2c(c1)OCCCO2 | Cc1cc2nc(NC(=O)c3ccc(C(C)(C)O)cc3)cc(Cl)n2n1 | null | Cl[Pd]Cl | [Fe+2] | c1ccc(P(c2ccccc2)[c-]2cccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | CO | null | null | null | null | null | null | null | null | null | 110 | null | A suspension of N-(7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide (2F, 60 mg, 0.174 mmol), 3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-ylboronic acid (49 mg, 0.226 mmol), and 1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (7 mg, 9.5 μmol) in 2:1 1,4-dioxane/saturated aqueous Na... | Cc1cc2nc(NC(=O)c3ccc(C(C)(C)O)cc3)cc(-c3ccc4c(c3)OCCCO4)n2n1 | null | 26.1 | null |
20,359 | ord_dataset-2a1960001e7d4e89987253631df1362a | null | 1977-01-01T00:02:00 | true | C([O:3][C:4]([CH:6]1[CH2:18][CH2:17][C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([Cl:19])[CH:14]=3)[N:9]([CH3:20])[C:8]=2[CH2:7]1)=[O:5])C.[OH-].[Na+]>C(O)C>[Cl:19][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH3:20])[C:8]1[CH2:7][CH:6]([C:4]([OH:5])=[O:3])[CH2:18][CH2:17][C:16]2=1 | CCOC(=O)C1CCc2c(n(C)c3ccc(Cl)cc23)C1 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 25 | 6 | A mixture of 4.6 g. of 6-chloro-9-methyl-1,2,3,4-tetrahydrocarbazole-2-carboxylic acid ethyl ester, 25 ml. of ethanol and 25 ml. of 3N sodium hydroxide was refluxed and stirred for 6 hours. Upon cooling to room temperature, the reaction mixture was concentrated to dryness under reduced pressure. The residue was dissolv... | Cn1c2c(c3cc(Cl)ccc31)CCC(C(=O)O)C2 | null | null | null |
1,529,210 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | [CH3:1][NH:2][CH2:3][C:4]1[N:8]([CH2:9][CH:10](O)[CH3:11])[N:7]=[C:6]([N+:13]([O-:15])=[O:14])[CH:5]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH3:1][N:2]1[CH:10]([CH3:11])[CH2:9][N:8]2[N:7]=[C:6]([N+:13]([O-:15])=[O:14])[CH:5]=[C:4]2[CH2:3]1 | CNCc1cc([N+](=O)[O-])nn1CC(C)O | null | null | CC(C)OC(=O)N=NC(=O)OC(C)C | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 0 | 5 | To a mixture of 250c (1.129 g, 5.27 mmol) and triphenylphosphine (4.14 g, 15.8 mmol) in anhydrous THF (40 mL) cooled at 0° C. was added the solution of di-isopropyl azodicarboxylate (DIAD) (3.19 g, 15.8 mmol) in THF (15 mL) over a period of 30 minutes while maintaining the internal temperature below 5° C. The reaction ... | CC1Cn2nc([N+](=O)[O-])cc2CN1C | null | 80.3 | null |
737,651 | ord_dataset-76dd1b78ee414d2da0ed30700ef026f7 | null | 2006-01-01T00:10:00 | true | [OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.O[CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[O:1][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:2... | Oc1ccccn1 | CC(C)(C)OC(=O)N1CCC(O)CC1 | null | CCOC(=O)N=NC(=O)OCC | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 4 | To a solution of 2-hydroxypyridine (2.0 g), tert-butyl 4-hydroxy-1-piperidinecarboxylate (5.3 g) and triphenylphosphine (8.3 g) in tetrahydrofuran (63 ml) was slowly added diethyl azodicarboxylate (5.5 g) at 8° C., and the mixture was stirred at room temperature for 4 hours. The reaction mixture was concentrated in vac... | CC(C)(C)OC(=O)N1CCC(Oc2ccccn2)CC1 | null | null | null |
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