index int64 0 919k | original_index int64 2 1.77M | agent_000 stringlengths 1 540 ⌀ | agent_001 stringlengths 1 852 ⌀ | agent_002 stringlengths 1 240 ⌀ | date_of_experiment timestamp[ns] | extracted_from_file stringlengths 44 44 | grant_date timestamp[ns] | is_mapped bool 1
class | procedure_details stringlengths 13 24.5k | product_000 stringlengths 1 457 | product_001 stringlengths 1 208 ⌀ | reactant_000 stringlengths 1 696 | reactant_001 stringlengths 1 902 ⌀ | reactant_002 stringlengths 1 285 ⌀ | rxn_str stringlengths 87 6.12k | rxn_time float64 0 1.49k ⌀ | solvent_000 stringlengths 1 64 ⌀ | solvent_001 stringlengths 1 29 ⌀ | solvent_002 stringlengths 1 29 ⌀ | temperature float64 -230 30.1k ⌀ | yield_000 float64 0 90,205,156,600B ⌀ | yield_001 float64 0 100M ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
38,952 | 1,579,049 | null | null | null | null | ord_dataset-9741bb5fd93044078df2a45f45733054 | 2015-01-01T00:04:00 | true | The title product (590 mg, yield: 93%) was prepared using a procedure similar to the one described for the synthesis of INTERMEDIATE 24 utilizing (R)-4-(phenylthio)-3-(4-sulfamoyl-2-(trifluoromethylsulfonyl)phenylamino)butanoic acid (INTERMEDIATE 8, 400 mg, 0.8 mmol) and 2-(tert-butyldiphenylsilyloxy)-N-methylethanamin... | CN(CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)C(=O)C[C@H](CSc1ccccc1)Nc1ccc(S(N)(=O)=O)cc1S(=O)(=O)C(F)(F)F | null | CNCCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C | NS(=O)(=O)c1ccc(N[C@@H](CSc2ccccc2)CC(=O)O)c(S(=O)(=O)C(F)(F)F)c1 | null | [C:1]1([S:7][CH2:8][C@H:9]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([S:21](=[O:24])(=[O:23])[NH2:22])=[CH:17][C:16]=2[S:25]([C:28]([F:31])([F:30])[F:29])(=[O:27])=[O:26])[CH2:10][C:11]([OH:13])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Si:32]([O:49][CH2:50][CH2:51][NH:52][CH3:53])([C:45]([CH3:48])([CH3:47])[CH3:46])([C:39]1[CH:... | null | null | null | null | null | null | 92.9 |
650,218 | 336,298 | F[B-](F)(F)F | null | null | null | ord_dataset-65c44df6676d4ce3a1874db5d7958ca9 | 1996-01-01T00:08:00 | true | To a cold (-5° C.) suspension of 4.45 g (16.00 mmol) of compound (19) in 25 ml acetonitrile was added dropwise a suspension of 2.60 g (16.64 mmol) of nitronium tetrafluoroborate in 5 ml of acetonitrile. After ten minutes, the homogenous, light-yellow reaction mixture was poured into water and extracted twice with ethyl... | CC(=O)Nc1ccc([N+](=O)[O-])c2c(Br)ccc(C)c12 | null | O=[N+]=O | CC(=O)Nc1cccc2c(Br)ccc(C)c12 | null | [Br:1][C:2]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[NH:13][C:14](=[O:16])[CH3:15].F[B-](F)(F)F.[O:22]=[N+:23]=[O:24].O>C(#N)C>[Br:1][C:2]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]2[C:3]=1[C:4]([N+:23]([O-:24])=[O:22])=[CH:5][CH:6]=[C:7]2[NH:13][C:14](=[O:16])[CH3:15] | null | CC#N | O | null | null | null | null |
270,837 | 320,044 | COc1cccc(C2(O)CCCCC2CN(C)C)c1 | Cl | null | null | ord_dataset-0c61835e3a0b4986aabf2b61b708e322 | 1995-01-01T00:11:00 | true | First, tramadol N-oxide was prepared as set forth hereinafter. Tramadol hydrochloride (0.5 mol) was converted its free base in basified water (pH >9) and then extracted with ether. The ether was evaporated to yield the crystalline hydrate of tramadol. The solid was then heated with steam under a high vacuum to remove a... | COc1cccc(C2(O)CCCCC2C[N+](C)(C)[O-])c1 | null | O | null | null | [CH3:1][N:2]([CH2:4][CH:5]1[C:10]([OH:19])([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][CH:12]=2)[CH2:9][CH2:8][CH2:7][CH2:6]1)[CH3:3].Cl.[OH2:21]>>[CH3:3][N+:2]([O-:21])([CH2:4][CH:5]1[C:10]([OH:19])([C:11]2[CH:12]=[CH:13][CH:14]=[C:15]([O:17][CH3:18])[CH:16]=2)[CH2:9][CH2:8][CH2:7][CH2:6]1)[CH3:1].[CH3:3][N:2... | null | null | null | null | null | null | null |
424,827 | 56,329 | null | null | null | null | ord_dataset-12a0ec4f3cda46e2badc694da2072c39 | 1979-01-01T00:06:00 | true | A solution of dimethyl cyanodithioimidocarbonate (9.0 g, 0.615 mole) and 1,1-dimethylpropargylamine (90% amine, remainder water, 5.68 g, 0.0615 mole) in acetonitrile (125 ml) was stirred at reflux temperature for 13 days. The reaction mixture was evaporated under reduced pressure and the residue chromatographed on sili... | C#CC(C)(C)N=C(NC#N)SC | null | CSC(=NC#N)SC | C#CC(C)(C)N | null | [C:1]([N:3]=[C:4](SC)[S:5][CH3:6])#[N:2].[CH3:9][C:10]([NH2:14])([C:12]#[CH:13])[CH3:11]>C(#N)C>[C:1]([NH:3][C:4](=[N:14][C:10]([CH3:11])([C:12]#[CH:13])[CH3:9])[S:5][CH3:6])#[N:2] | null | CC#N | null | null | null | null | null |
723,673 | 187,577 | null | null | null | null | ord_dataset-3ec273742a0345ea916ad5fd071167f2 | 1989-01-01T00:04:00 | true | An amount of 843 g (2.1 mol) of 2-(p-nitrophenoxy]-myristoyl chloride is added dropwise in 60 min to a cooled (0°-5° C.) solution of 525 g (2 mol) of 2-benzamido-4-chloro-5-aminophenol in 6 l of tetrahydrofuran and 220 ml of quninoline. The temperature of the reaction mixture is kept below 10° C. The precipitate of qui... | CCCCCCCCCCCCC(Oc1ccc([N+](=O)[O-])cc1)C(=O)Nc1cc(O)c(NC(=O)c2ccccc2)cc1Cl | null | CCCCCCCCCCCCC(Oc1ccc([N+](=O)[O-])cc1)C(=O)Cl | Nc1cc(O)c(NC(=O)c2ccccc2)cc1Cl | null | [N+:1]([C:4]1[CH:26]=[CH:25][C:7]([O:8][CH:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:10](Cl)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:27]([NH:35][C:36]1[CH:41]=[C:40]([Cl:42])[C:39]([NH2:43])=[CH:38][C:37]=1[OH:44])(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:3... | null | C1CCOC1 | null | null | 5 | null | null |
152,488 | 194,413 | [Na+] | [OH-] | null | null | ord_dataset-b83b16f2fb1a4f8782f3d82c1766cc6b | 1989-01-01T00:08:00 | true | A mixture of 10.0 g (0.025 mole) of 2-[(7-benzoyl-1H-indol-3-yl)methyl]propanedioic acid diethyl ester in 150 ml of 3N sodium hydroxide was heated at reflux for 18 hr, then treated with charcoal, cooled and filtered. The dark yellow filtrate was acidified by the dropwise addition of 50 ml of concentration hydrochloric ... | O=C(c1ccccc1)c1cccc2c(CC(C(=O)O)C(=O)O)c[nH]c12 | null | CCOC(=O)C(Cc1c[nH]c2c(C(=O)c3ccccc3)cccc12)C(=O)OCC | null | null | C([O:3][C:4](=[O:29])[CH:5]([CH2:11][C:12]1[C:20]2[C:15](=[C:16]([C:21](=[O:28])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1)[C:6]([O:8]CC)=[O:7])C.C>[OH-].[Na+]>[C:21]([C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:15]=1[NH:14][CH:13]=[C:12]2[CH2:11][CH:5]([C:6]([OH:8])=[O:7])[C:4]... | null | null | null | null | null | null | 71.1 |
227,252 | 208,521 | null | null | null | null | ord_dataset-ac1c7aa04d6c4e588e723e3e05721681 | 1990-01-01T00:05:00 | true | 2-ethoxyethyl p-methoxycinnamate or "Cinoxate" according to the common international name, sold under the trade name Giv-Tan F; | COc1ccc(C=CC(=O)OC2CCCCC2)cc1 | null | CCOCCOC(=O)C=Cc1ccc(OC)cc1 | CCOCCOC(=O)/C=C/c1ccc(OC)cc1 | null | [CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH:7]=[CH:8][C:9]([O:11][CH2:12][CH2:13]OCC)=[O:10])=[CH:5][CH:4]=1.CCOCCO[C:25](/[CH:27]=[CH:28]/[C:29]1C=CC(OC)=CC=1)=O>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:7]=[CH:8][C:9]([O:11][CH:12]2[CH2:13][CH2:29][CH2:28][CH2:27][CH2:25]2)=[O:10])=[CH:17][CH:18]=1 | null | null | null | null | null | null | null |
787,400 | 504,570 | O=C([O-])[O-] | [I-] | [K+] | null | ord_dataset-631d58dab387485c8eb0db4c20a232b7 | 2001-01-01T00:06:00 | true | A mixture containing 4-piperazinoindole (0.2 mmole), potassium carbonate (0.5 mmole), potassium iodide (0.08 mmole) and 4-benzyl-5-chloromethyl-2-cyclohexyl oxazole (0.19 mmole) from example 2 was stirred in acetone (2 ml) for 16 hr. The mixture was concentrated in vacuo, water (10 ml) added, and the product extracted ... | c1ccc(Cc2nc(C3CCCCC3)oc2CN2CCN(c3cccc4[nH]ccc34)CC2)cc1 | null | c1cc(N2CCNCC2)c2cc[nH]c2c1 | ClCc1oc(C2CCCCC2)nc1Cc1ccccc1 | null | [N:1]1([C:7]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:8]=2[CH:9]=[CH:10][NH:11]3)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH2:24]([C:31]1[N:32]=[C:33]([CH:38]2[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]2)[O:34][C:35]=1[CH2:36]Cl)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CC(C)=O>[CH2:24]([C:31]... | null | CC(C)=O | null | null | null | null | 94 |
568,805 | 695,760 | [H-] | [Na+] | null | null | ord_dataset-a7baa616c65d42559e25ca0ba61e0744 | 2006-01-01T00:01:00 | true | A mixture of 2,4-dichloro-5-methoxyaniline (1.1 g, 5.7 mmol) and 60% sodium hydride (285 mg, 9.9 mmol) in 30 mL of tetrahydrofuran is heated at reflux for 1 hour. The solution is cooled and 4-chloro-2-iodothieno[2,3-b]pyridine-5-carbonitrile (1.0 g, 3.12 mmol) is added. The reaction mixture is heated at reflux for 5 ho... | COc1cc(Nc2c(C#N)cnc3sc(I)cc23)c(Cl)cc1Cl | null | COc1cc(N)c(Cl)cc1Cl | N#Cc1cnc2sc(I)cc2c1Cl | null | [Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[C:6]([O:10][CH3:11])=[CH:5][C:3]=1[NH2:4].[H-].[Na+].Cl[C:15]1[C:20]([C:21]#[N:22])=[CH:19][N:18]=[C:17]2[S:23][C:24]([I:26])=[CH:25][C:16]=12>O1CCCC1>[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[C:6]([O:10][CH3:11])=[CH:5][C:3]=1[NH:4][C:15]1[C:20]([C:21]#[N:22])=[CH:19][N:18]=[C:17]2[S:23][C:24](... | 8 | C1CCOC1 | null | null | 25 | 18.8 | null |
219,980 | 1,152,358 | [Ni] | null | null | null | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | 2012-01-01T00:04:00 | true | To a solution of 1-(1,1-dimethylethyl) 2-methyl (2R,5R)-2-(2-cyanoethyl)-5-{4-[(phenylmethyl)oxy]phenyl}-1,2-pyrrolidinedicarboxylate (D49, 215 mg, 0.46 mmol) in methanol (20 mL) was added Raney Nickel (slurry in water, 1 spatula) and the mixture was stirred under a hydrogen atmosphere (6 atm) for 4.5 hours. The cataly... | O=C1NCCC[C@]12CCC(c1ccc(O)cc1)N2 | null | COC(=O)[C@]1(CCC#N)CC[C@H](c2ccc(OCc3ccccc3)cc2)N1C(=O)OC(C)(C)C | null | null | [C:1]([CH2:3][CH2:4][C@@:5]1([C:31]([O:33]C)=O)[CH2:9][CH2:8][C@H:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16]CC3C=CC=CC=3)=[CH:12][CH:11]=2)[N:6]1C(OC(C)(C)C)=O)#[N:2].C(O)(C(F)(F)F)=O>CO.[Ni].ClCCl>[OH:16][C:13]1[CH:14]=[CH:15][C:10]([CH:7]2[CH2:8][CH2:9][C@:5]3([CH2:4][CH2:3][CH2:1][NH:2][C:31]3=[O:33])[NH:6]2)=[CH:11][CH... | 4.5 | ClCCl | CO | O=C(O)C(F)(F)F | 0 | 19.4 | null |
551,240 | 1,667,002 | CN(C)C(On1nnc2cccnc21)=[N+](C)C | F[P-](F)(F)(F)(F)F | null | null | ord_dataset-9cc455db05a444779921f786a45b21a6 | 2015-01-01T00:12:00 | true | A mixture of 3-amino-4-{(3S)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl acetate (15.0 mg, 0.0384 mmol), 6-[2,6-difluoro-4-(methylsulfonyl)phenyl]-5-fluoropyridine-2-carboxylic acid (15.3 mg, 0.0461 mmol), HATU (36.5 mg, 0.0960 mmol) in DMF (0.09 mL) and DIPEA (14.9 mg, 0.115 ... | CC(=O)OC1CCc2c1ncc(NC(=O)c1ccc(F)c(-c3c(F)cc(S(C)(=O)=O)cc3F)n1)c2N1CCC[C@H](NC(=O)OC(C)(C)C)C1 | null | CC(=O)OC1CCc2c1ncc(N)c2N1CCC[C@H](NC(=O)OC(C)(C)C)C1 | CS(=O)(=O)c1cc(F)c(-c2nc(C(=O)O)ccc2F)c(F)c1 | null | [C:1]([O:4][CH:5]1[C:9]2=[N:10][CH:11]=[C:12]([NH2:28])[C:13]([N:14]3[CH2:19][CH2:18][CH2:17][C@H:16]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:15]3)=[C:8]2[CH2:7][CH2:6]1)(=[O:3])[CH3:2].[F:29][C:30]1[CH:35]=[C:34]([S:36]([CH3:39])(=[O:38])=[O:37])[CH:33]=[C:32]([F:40])[C:31]=1[C:41]1[N:46]=[... | 16 | CCN(C(C)C)C(C)C | CN(C)C=O | null | 25 | null | 40.7 |
185,952 | 1,355,001 | [K+] | [OH-] | null | null | ord_dataset-6034127657614f02860ed057b62b882e | 2013-01-01T00:10:00 | true | To a stirred suspension of ethyl 1-(2-{[bis(benzyloxy)phosphoryl]oxy}ethyl)-6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (Example 30, 210 mg, 0.2511 mmol) in ethanol (20 mL), 10% potassium hydroxide (0.2 mL) was added. The reaction ... | CCNC(=O)Nc1cc(-c2nc(C(F)(F)F)cs2)c(-c2cnc3c(c2)c(=O)c(C(=O)O)cn3CCOP(=O)(OCc2ccccc2)OCc2ccccc2)cn1 | null | CCNC(=O)Nc1cc(-c2nc(C(F)(F)F)cs2)c(-c2cnc3c(c2)c(=O)c(C(=O)OCC)cn3CCOP(=O)(OCc2ccccc2)OCc2ccccc2)cn1 | null | null | [CH2:1]([O:8][P:9]([O:19][CH2:20][CH2:21][N:22]1[C:31]2[C:26](=[CH:27][C:28]([C:32]3[CH:33]=[N:34][C:35]([NH:47][C:48](=[O:52])[NH:49][CH2:50][CH3:51])=[CH:36][C:37]=3[C:38]3[S:39][CH:40]=[C:41]([C:43]([F:46])([F:45])[F:44])[N:42]=3)=[CH:29][N:30]=2)[C:25](=[O:53])[C:24]([C:54]([O:56]CC)=[O:55])=[CH:23]1)([O:11][CH2:12... | null | CCO | null | null | 60 | null | 73.9 |
435,543 | 592,899 | null | null | null | null | ord_dataset-278fb6af8a994ac69e4d95e6e6eff756 | 2003-01-01T00:05:00 | true | A solution of 7-methylindoline (10.2 g) in acetic anhydride (25 ml) was refluxed for 30 min. After cooling, the reaction solution was poured into ice water (250 ml) and the resulting crystal was filtered by means of suction, heated and vacuum dried to yield the end product (11.7 g). | CC(=O)N1CCc2cccc(C)c21 | null | CC(=O)OC(C)=O | Cc1cccc2c1NCC2 | null | [CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH2:8][CH2:7]2.[C:11](OC(=O)C)(=[O:13])[CH3:12]>>[C:11]([N:9]1[C:10]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[CH3:1])[CH2:7][CH2:8]1)(=[O:13])[CH3:12] | null | null | null | null | 0 | null | null |
165,700 | 621,765 | null | null | null | null | ord_dataset-c9f990dde2dc45d0948ecbe037a0d819 | 2004-01-01T00:01:00 | true | (2R,3R,4 R,5R)-4-(acetyloxy)-2-(2,6-dichloro-9H-purin-9-yl)-5-(5-ethylisoxazol-3-yl)tetrahydrofuran-3-yl acetate (125 mg) was dissolved in isopropanol (5 ml) and the solution was treated with diisopropylethylamine (0.06 ml) followed by 1-ethylpropylamine (0.044 ml). The mixture was heated at 50° C. under nitrogen for 1... | CCc1cc([C@H]2O[C@@H](n3cnc4c(NC(CC)CC)nc(Cl)nc43)[C@H](OC(C)=O)[C@@H]2OC(C)=O)no1 | null | CCc1cc([C@H]2O[C@@H](n3cnc4c(Cl)nc(Cl)nc43)[C@H](OC(C)=O)[C@@H]2OC(C)=O)no1 | CCC(N)CC | null | [C:1]([O:4][C@@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([C:14]2[CH:18]=[C:17]([CH2:19][CH3:20])[O:16][N:15]=2)[O:7][C@H:6]1[N:21]1[CH:29]=[N:28][C:27]2[C:22]1=[N:23][C:24]([Cl:31])=[N:25][C:26]=2Cl)(=[O:3])[CH3:2].C(N(C(C)C)CC)(C)C.[CH2:41]([CH:43]([NH2:46])[CH2:44][CH3:45])[CH3:42]>C(O)(C)C>[C:1]([O:4][C@@H... | null | CCN(C(C)C)C(C)C | CC(C)O | null | 50 | null | null |
460,023 | 1,220,566 | CC[SiH](CC)CC | O=C([O-])[O-] | [K+] | null | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | 2012-01-01T00:10:00 | true | To a solution of the crude (2R,5R)-2-(tert-butyldiphenylsilanyloxy)-6-oxo-spiro[4.5]de cane-7-carboxylic acid methyl ester (1.65 g) obtained in Step 4 in toluene (1.6 mL) were added trifluoroacetic acid (5 mL) and triethylsilane (0.52 mL) under ice-cooling, followed by stirring the mixture under ice-cooling for 3 hours... | COC(=O)C1CCC[C@]2(CC[C@@H](O[Si](c3ccccc3)(c3ccccc3)C(C)(C)C)C2)C1O | null | COC(=O)C1CCC[C@]2(CC[C@@H](O[Si](c3ccccc3)(c3ccccc3)C(C)(C)C)C2)C1=O | null | null | [CH3:1][O:2][C:3]([CH:5]1[CH2:32][CH2:31][CH2:30][C@@:7]2([CH2:11][C@H:10]([O:12][Si:13]([C:26]([CH3:29])([CH3:28])[CH3:27])([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:9][CH2:8]2)[C:6]1=[O:33])=[O:4].FC(F)(F)C(O)=O.C([SiH](CC)CC)C.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=... | null | O=C(O)C(F)(F)F | Cc1ccccc1 | O | null | 106.2 | null |
587,458 | 584,709 | null | null | null | null | ord_dataset-cb5dd7a8b94e4f19a9148a1904b0dcb6 | 2003-01-01T00:03:00 | true | Methanesulfonyl chloride (0.94 ml) was added to a solution of ethyl 3-(4-benzyloxyphenyl)lactate (3.32 g), which is the product of Reference example 1(b), in anhydrous dichloromethane (30 ml). To this mixture triethylamine (2.47 ml) was added dropwise in an ice bath. The mixture was stirred at ambient temperature for 3... | CCOC(=O)C(Cc1ccc(OCc2ccccc2)cc1)OS(C)(=O)=O | null | CCOC(=O)C(O)Cc1ccc(OCc2ccccc2)cc1 | CS(=O)(=O)Cl | null | [CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([O:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH:21]([OH:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C>ClCCl>[CH2:6]([O:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH:21]([O:27][S:2]([CH3:1])(=[O:4])=[O:3])[C:22]([O:... | 3 | CCN(CC)CC | ClCCl | null | 25 | null | null |
257,838 | 870,677 | [I-] | null | null | null | ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | 2009-01-01T00:03:00 | true | As described for example 84b, 2-(4-methyl-imidazol-1-yl)-5-trifluoromethoxy benzonitrile (+regioisomer) was reacted with Eschenmoser's salt in DMF for 24 h at 90° C. Evaporation of the solvent, aqueous workup and chromatography afforded the title compound as a colorless oil that was sufficiently pure to be used in the ... | Cc1ncn(-c2ccc(OC(F)(F)F)cc2C#N)c1CN(C)C | null | Cc1cn(-c2ccc(OC(F)(F)F)cc2C#N)cn1 | C=[N+](C)C | null | [CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][C:8]=2[C:9]#[N:10])[CH:6]=1.[CH3:20][N+:21]([CH3:23])=[CH2:22].[I-]>CN(C=O)C>[CH3:20][N:21]([CH2:23][C:6]1[N:5]([C:7]2[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:17])[F:18])=[CH:11][C:8]=2[C:9]#[N:10])[CH:4]=[N:3][C... | null | CN(C)C=O | null | null | null | null | 38 |
33,451 | 910,370 | null | null | null | null | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | 2009-01-01T00:09:00 | true | This compound was made in the following manner: 50 mg of 3-(S)-benzyl-1-(2′-chloro-5′-methyl-biphenyl-4-ylmethyl)-piperazine was dissolved in THF, 2 equiv. of acetylchloride and 2 equiv. of N,N-diisopropylethylamine were added. The reaction was stirred at room temperature overnight. The reaction was diluted with DCM, w... | CC(=O)N1CCN(Cc2ccc(-c3cc(C)ccc3Cl)cc2)C[C@@H]1Cc1ccccc1 | null | CC(=O)Cl | Cc1ccc(Cl)c(-c2ccc(CN3CCN[C@@H](Cc4ccccc4)C3)cc2)c1 | null | [CH2:1]([C@@H:8]1[NH:13][CH2:12][CH2:11][N:10]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[C:25]([CH3:27])[CH:24]=[CH:23][C:22]=3[Cl:28])=[CH:17][CH:16]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:29](Cl)(=[O:31])[CH3:30].C(N(CC)C(C)C)(C)C>C1COCC1.C(Cl)Cl>[CH2:1]([C@H:8]1[CH2:9][N:10]([CH2:14][C:15]... | 8 | CCN(C(C)C)C(C)C | ClCCl | C1CCOC1 | 25 | null | null |
885,386 | 1,755,849 | [O-][Cl+3]([O-])([O-])O | null | null | null | ord_dataset-97eb2ab57fec4160922caae33b54d956 | 2016-01-01T00:08:00 | true | To a solution of 2,6-dichloro-4-methylnicotinic acid (1.00 g, 4.85 mmol, 1 equiv) in tert-butyl acetate (24 mL) was added 70% perchloric acid (0.88 mL, 14.56 mmol, 3 equiv). After 1 h, reaction was diluted with DCM, washed cautiously with saturated aqueous sodium bicarbonate solution, dried (Na2SO4), and concentrated i... | Cc1cc(Cl)nc(Cl)c1C(=O)OC(C)(C)C | null | Cc1cc(Cl)nc(Cl)c1C(=O)O | null | null | [Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[C:7]([CH3:12])[C:3]=1[C:4]([OH:6])=[O:5].Cl(O)(=O)(=O)=O>C(OC(C)(C)C)(=O)C.C(Cl)Cl>[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[C:7]([CH3:12])[C:3]=1[C:4]([O:6][C:3]([CH3:7])([CH3:4])[CH3:2])=[O:5] | 1 | CC(=O)OC(C)(C)C | ClCCl | null | null | 190.4 | null |
701,363 | 1,118,058 | null | null | null | null | ord_dataset-4226e9b4f9f845db967ed997270dcafc | 2011-01-01T00:12:00 | true | 3-{1-[5-chloro-2-(trifluoromethyl)benzyl]-1,2,3,4-tetrahydropyrido[2,3-b]pyrazin-7-yl}benzoic acid was reacted with 4-phenylpiperidine as in General Procedure 10 to give the title compound. LCMS: m/z=590.98 (M+H+); retention time=1.03 minutes. | O=C(c1cccc(-c2cnc3c(c2)N(Cc2cc(Cl)ccc2C(F)(F)F)CCN3)c1)N1CCC(c2ccccc2)CC1 | null | c1ccc(C2CCNCC2)cc1 | O=C(O)c1cccc(-c2cnc3c(c2)N(Cc2cc(Cl)ccc2C(F)(F)F)CCN3)c1 | null | [Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:28]([F:31])([F:30])[F:29])=[C:6]([CH:27]=1)[CH2:7][N:8]1[CH2:13][CH2:12][NH:11][C:10]2[N:14]=[CH:15][C:16]([C:18]3[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=3)[C:21](O)=[O:22])=[CH:17][C:9]1=2.[C:32]1([CH:38]2[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>>... | null | null | null | null | null | null | null |
396,337 | 276,504 | O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F | null | null | null | ord_dataset-02ee2261663048188cf6d85d2cc96e3f | 1993-01-01T00:09:00 | true | A solution of trifluoromethanesulfonic anhydride (0.954 g, 3.38 mmol) in methylene chloride (5 ml) was cooled to -78° C. under nitrogen, and a solution of 2-n-butyl-1-(2-chlorophenyl)methyl-5-(2-hydroxyethyl)-1H-imidazole (0.9 g, 3.07 mmol), diisopropylethylamine (0.44 g. 3.38 mmol) and methylene chloride (10 ml) was a... | CCCCc1ncc(CCN[C@@H](Cc2ccccc2)C(=O)OC)n1Cc1ccccc1Cl | null | COC(=O)[C@@H](N)Cc1ccccc1 | CCCCc1ncc(CCO)n1Cc1ccccc1Cl | null | FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[CH2:16]([C:20]1[N:21]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[Cl:35])[C:22]([CH2:25][CH2:26]O)=[CH:23][N:24]=1)[CH2:17][CH2:18][CH3:19].C(N(C(C)C)CC)(C)C.[CH3:45][O:46][C:47](=[O:57])[C@H:48]([CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[NH2:49]>C(Cl)Cl>[CH3:... | 0.25 | CCN(C(C)C)C(C)C | ClCCl | null | -78 | null | 64.6 |
383,228 | 1,709,383 | null | null | null | null | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | 2016-01-01T00:04:00 | true | The title compound was prepared using 6-bromo-3-phenoxy-4-(trifluoromethyl)quinolin-2(1H)-one (Intermediate 8, step a) in place of 6-bromo-3-(4-chlorophenoxy)-4-(trifluoromethyl)quinolin-2(1H)-one (Intermediate 7, step c) according to the procedure described in Intermediate 7, step d. | FC(F)(F)c1c(Oc2ccccc2)c(Cl)nc2ccc(Br)cc12 | null | O=c1[nH]c2ccc(Br)cc2c(C(F)(F)F)c1Oc1ccc(Cl)cc1 | O=c1[nH]c2ccc(Br)cc2c(C(F)(F)F)c1Oc1ccccc1 | null | [Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=O)[C:6]([O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[C:5]2[C:20]([F:23])([F:22])[F:21].BrC1C=C2C(=CC=1)NC(=O)C(OC1C=CC([Cl:43])=CC=1)=C2C(F)(F)F>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([Cl:43])[C:6]([O:13][C:14]1[CH:19]=[CH:18... | null | null | null | null | null | null | null |
352,605 | 188,369 | null | null | null | null | ord_dataset-3ec273742a0345ea916ad5fd071167f2 | 1989-01-01T00:04:00 | true | A solution of 3-butyl-6-hydrazino-1-(4-methoxybenzyl)uracil 0.64 g, 2 mM) and ethyl isothiocyanate (0.53 ml, 6 mM) in DMF (6 ml) was stirred at 90° C. for 14 hours and then at 110° C. for 14 hours. To the solution was added water (2 ml) and the mixture was cooled to give crystals. Recrystallization from DMF/ethanol/wat... | CCCCn1c(=O)c2c(NCC)n[nH]c2n(Cc2ccc(OC)cc2)c1=O | null | CCN=C=S | CCCCn1c(=O)cc(NN)n(Cc2ccc(OC)cc2)c1=O | null | [CH2:1]([N:5]1[C:10](=[O:11])[CH:9]=[C:8]([NH:12][NH2:13])[N:7]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[C:6]1=[O:23])[CH2:2][CH2:3][CH3:4].[CH2:24]([N:26]=[C:27]=S)[CH3:25].O>CN(C=O)C>[CH2:1]([N:5]1[C:10](=[O:11])[C:9]2[C:27]([NH:26][CH2:24][CH3:25])=[N:13][NH:12][C:8]=2[N:7]([CH2:14][C:1... | 14 | O | CN(C)C=O | null | null | null | 70 |
912,230 | 965,217 | CC(=O)O[BH-](OC(C)=O)OC(C)=O | [Na+] | [OH-] | null | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | 2010-01-01T00:06:00 | true | To a solution of 3-[5-(6-Methyl-pyridin-3-yl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-propionaldehyde (Prep59, 90 mg, 0.35 mmol), (1S,5R)-1-(4-trifluoromethyl-phenyl)-3-aza-bicyclo[3.1.0]hexane (Prep4, 71 mg, 0.31 mmol) and AcOH (21 mg, 0.35 mmol) in dichloroethane (2 mL), NaBH(AcO)3 (77 mg, 0.36 mmol) was added porti... | Cc1ccc(-c2cn(CCCN3C[C@@H]4C[C@]4(c4ccc(C(F)(F)F)cc4)C3)c(=O)[nH]c2=O)cn1 | Cl | Cc1ccc(-c2cn(CCC=O)c(=O)[nH]c2=O)cn1 | CC(Cl)Cl | FC(F)(F)c1ccc([C@@]23CNC[C@@H]2C3)cc1 | [CH3:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[C:9](=[O:19])[NH:10][C:11](=[O:18])[N:12]([CH2:14][CH2:15][CH:16]=O)[CH:13]=2)=[CH:4][CH:3]=1.[F:20][C:21]([F:35])([F:34])[C:22]1[CH:27]=[CH:26][C:25]([C@:28]23[CH2:33][C@H:32]2[CH2:31][NH:30][CH2:29]3)=[CH:24][CH:23]=1.CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[Na+].[Cl:5... | 0.75 | CC(=O)O | null | null | 0 | 40 | null |
508,022 | 22,450 | N#CCCl | null | null | null | ord_dataset-19b9e29d593f4660ab77c07b459da9bb | 1977-01-01T00:04:00 | true | A mixture of 7-methoxy-2-tetralone (472 g., 2.68 mole), pyrrolidine (241 g., 3.40 mole) and benzene (2.5l) was refluxed under nitrogen with water separation (Dean-Stark trap) for 2 hrs. and then distilled for a further 1 hr. (1.2l) of distillate). Chloroacetonitrile (324 g., 4.30 mole) was added during 15 mins. and the... | COc1ccc2c(c1)C(CC#N)C(=O)CC2 | null | C1CCNC1 | COc1ccc2c(c1)CC(=O)CC2 | null | [CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=[O:13])[CH2:10]2)=[CH:5][CH:4]=1.[NH:14]1CC[CH2:16][CH2:15]1.C1C=CC=CC=1.ClCC#N>O>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=[O:13])[CH:10]2[CH2:16][C:15]#[N:14])=[CH:5][CH:4]=1 | 8 | O | c1ccccc1 | null | null | null | null |
737,433 | 1,025,907 | null | null | null | null | ord_dataset-136cfada6ce247b4919085a57363459e | 2011-01-01T00:01:00 | true | 4,5-Dimethyl-thiazol-2-ylamine and 2-(2-bromo-ethoxy)-1,1,1,-trifluoro-ethane were mixed and heated at 65° C. for 4 hours. The residue was triturated with hexane to afford the title compound. MS (ESI+) m/z 255 (M+H)+. | Br | Cc1sc(=N)n(CCOCC(F)(F)F)c1C | FC(F)(F)COCCBr | Cc1nc(N)sc1C | null | [CH3:1][C:2]1[N:3]=[C:4]([NH2:8])[S:5][C:6]=1[CH3:7].[Br:9][CH2:10][CH2:11][O:12][CH2:13][C:14]([F:17])([F:16])[F:15]>>[BrH:9].[CH3:1][C:2]1[N:3]([CH2:10][CH2:11][O:12][CH2:13][C:14]([F:17])([F:16])[F:15])[C:4](=[NH:8])[S:5][C:6]=1[CH3:7] | null | null | null | null | 65 | null | null |
840,860 | 1,320,599 | null | null | null | null | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | 2013-01-01T00:07:00 | true | To a solution of methyl 2-amino-6-[4-fluoro-3-({[3-(trifluoromethyl)phenyl]acetyl}amino)phenoxy]-1,3-benzothiazole-7-carboxylate (2.50 mg, 4.81 mmol) in tetrahydrofuran (20 mL) were added pyridine (770 μL, 9.62 mmol) and cyclopropanecarbonyl chloride (790 μL, 8.66 mmol), and the mixture was stirred at room temperature ... | COC(=O)c1c(Oc2ccc(F)c(NC(=O)Cc3cccc(C(F)(F)F)c3)c2)ccc2nc(NC(=O)C3CC3)sc12 | null | COC(=O)c1c(Oc2ccc(F)c(NC(=O)Cc3cccc(C(F)(F)F)c3)c2)ccc2nc(N)sc12 | O=C(Cl)C1CC1 | null | [NH2:1][C:2]1[S:3][C:4]2[C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([O:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[C:18]([NH:23][C:24](=[O:36])[CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=4)[CH:17]=3)[CH:8]=[CH:7][C:5]=2[N:6]=1.N1C=CC=CC=1.[CH:43]1([C:46](Cl)=[O:47])[CH2:45][CH2:44]1>O... | 12 | c1ccncc1 | CCOC(C)=O | C1CCOC1 | 25 | null | 79.6 |
481,568 | 970,863 | null | null | null | null | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | 2010-01-01T00:06:00 | true | The title compound was prepared from N-(5-iodo-2,3-dihydro-1H-inden-2-yl)-2-propanesulfonamide and [3-(aminosulfonyl)phenyl]boronic acid (WO2003004472) in a similar manner to Example 1. | CC(C)S(O)(O)NC1Cc2ccc(-c3cccc(S(N)(=O)=O)c3)cc2C1 | null | CC(C)S(=O)(=O)NC1Cc2ccc(I)cc2C1 | NS(=O)(=O)c1cccc(B(O)O)c1 | null | I[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH:6]([NH:11][S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH2:5]2.[NH2:18][S:19]([C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1)(=[O:21])=[O:20]>>[OH:13][S:12]([NH:11][CH:6]1[CH2:5][C:4]2[C:8](=[CH:9][CH:10]=[C:2]([C:26]3[CH:27]=[C:22]([S:19]([NH2:18])(=[O:... | null | null | null | null | null | null | null |
7,417 | 64,192 | Cl | [Al+3] | [Cl-] | null | ord_dataset-b1bf0950b5cb430abbb1d80744f5df84 | 1980-01-01T00:03:00 | true | To a solution maintained at 0° C. of 12.5 g of the ester obtained according to (a) and 8.79 g thiophene-2-carboxylic acid chloride in 130 ml methylene chloride, there are added little by little 7.9 g aluminium chloride. The mixture is then maintained at reflux temperature for 6 hours and then poured into a mixture of i... | COC(=O)COc1ccc(C(=O)c2cccs2)c2c1CCCC2 | null | O=C(Cl)c1cccs1 | COC(=O)COc1cccc2c1CCCC2 | null | [C:1]1([O:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[S:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[C:22](Cl)=[O:23].[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(Cl)Cl>[C:18]1([C:22]([C:4]2[C:5]3[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=3[C:1]([O:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=... | null | ClCCl | null | null | null | 85 | null |
371,507 | 66,295 | null | null | null | null | ord_dataset-8af141577c90485cb9c91079a5ef96b3 | 1980-01-01T00:05:00 | true | A mixture of ethyl N-(6-amino-5-chloro-2-pyridyl)carbamate (64.7 g., 0.3 mole), dimethylamine (45 g., 1.0 mole) and 300 ml. of ethanol is heated at 120° C. for 24 hours in a pressure vessel. The reaction mixture is then concentrated in vacuo and 68 g. of brown solid is obtained. Recrystallization from n-butyl chloride ... | CN(C)C(=O)Nc1ccc(Cl)c(N)n1 | null | CNC | CCOC(=O)Nc1ccc(Cl)c(N)n1 | null | [NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9](=[O:13])OCC)[CH:5]=[CH:4][C:3]=1[Cl:14].[CH3:15][NH:16][CH3:17]>C(O)C>[CH3:15][N:16]([CH3:17])[C:9]([NH:8][C:6]1[CH:5]=[CH:4][C:3]([Cl:14])=[C:2]([NH2:1])[N:7]=1)=[O:13] | null | CCO | null | null | null | null | null |
391,247 | 406,435 | null | null | null | null | ord_dataset-d5bb2294ac964841b8ffc9e0a34e93af | 1998-01-01T00:07:00 | true | Compound 14g is prepared in a manner similar to that used for preparation of Compound 14 h using previously prepared Compound 13 and 2-thienylcarbonylmethyl chloride. | CC(C)(C)OC(=O)NC1C(=O)N(CC(=O)c2cccs2)c2ccccc2N(CC(=O)c2cccs2)C1=O | null | CC(C)(C)OC(=O)NC1C(=O)Nc2ccccc2NC1=O | O=C(CCl)c1cccs1 | null | [C:1]([O:5][C:6]([NH:8][CH:9]1[C:15](=[O:16])[NH:14][C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2[NH:11][C:10]1=[O:21])=[O:7])([CH3:4])([CH3:3])[CH3:2].[S:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[C:27]([CH2:29]Cl)=[O:28]>>[S:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[C:27]([CH2:29][N:14]1[C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2... | null | null | null | null | null | null | null |
835,433 | 752,824 | CCN=C=NCCCN(C)C | Cl | On1nnc2ccccc21 | null | ord_dataset-844a22e1fcab44a5b59c5e2922b2855a | 2007-01-01T00:01:00 | true | 2′-Methyl-5′-(5-methyl-1,3,4-oxadiazol-2-yl)-1,1′-biphenyl-4-carboxylic acid (11.3 mg, 0.034 mmol), HOBT (6.0 mg, 0.044 mmol), 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (8.0 mg, 0.042 mmol) and 2-methylbutylamine (0.34 mmol) were mixed in DMF (0.7 ml) and the reaction left at room temperature for 18 ... | CCC(C)CNC(=O)c1ccc(-c2cc(-c3nnc(C)o3)ccc2C)cc1 | null | Cc1nnc(-c2ccc(C)c(-c3ccc(C(=O)O)cc3)c2)o1 | CCC(C)CN | null | [CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:13])=[N:11][N:12]=2)=[CH:4][C:3]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20]([OH:22])=O)=[CH:16][CH:15]=1.C1C=CC2N(O)N=NC=2C=1.Cl.CN(C)CCCN=C=NCC.[CH3:45][CH:46]([CH2:49][CH3:50])[CH2:47][NH2:48]>CN(C=O)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:13])=[N:11][... | 18 | CN(C)C=O | null | null | null | null | null |
392,293 | 715,344 | null | null | null | null | ord_dataset-c8a367b56b4f406b878f51867b157d19 | 2006-01-01T00:06:00 | true | 15.2 ml (101 mmol) of 1-morpholino-1-cyclopentene is carefully added in drops to a solution of 20.0 g (101 mmol) of 3-bromophenylisocyanate in 100 ml of chloroform. The batch is refluxed for 15 minutes and concentrated by evaporation in a vacuum. Column chromatography on silica gel with hexane-ethyl acetate yielded 25.... | O=C1CCCC1C(=O)Nc1cccc(Br)c1 | null | C1=C(N2CCOCC2)CCC1 | O=C=Nc1cccc(Br)c1 | CCOC(C)=O | O1CCN([C:7]2[CH2:11][CH2:10][CH2:9][CH:8]=2)CC1.[Br:12][C:13]1[CH:14]=[C:15]([N:19]=[C:20]=[O:21])[CH:16]=[CH:17][CH:18]=1.CCCCCC.C(OCC)(=[O:30])C>C(Cl)(Cl)Cl>[Br:12][C:13]1[CH:14]=[C:15]([NH:19][C:20]([CH:7]2[CH2:8][CH2:9][CH2:10][C:11]2=[O:30])=[O:21])[CH:16]=[CH:17][CH:18]=1 | null | ClC(Cl)Cl | CCCCCC | null | null | null | null |
218,565 | 1,084,872 | null | null | null | null | ord_dataset-afd812677c134591a99f46ce28de2524 | 2011-01-01T00:08:00 | true | Step 2 Trifluoroacetic acid (0.56 mL, 7.3 mmol) was added to a solution of tert-butyl 2-[4-(2-oxopropoxy)phenyl]ethylcarbamate (216 mg, 0.74 mmol) in CH2Cl2 (4 mL). The reaction mixture was stirred for 3 hr at ambient temperature, and then reaction mixture was stripped of volatiles in vacuo. The residue (143 mg) was us... | CC(=O)COc1ccc(CCN)cc1 | null | CC(=O)COc1ccc(CCNC(=O)OC(C)(C)C)cc1 | null | null | FC(F)(F)C(O)=O.[O:8]=[C:9]([CH3:28])[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][NH:20]C(=O)OC(C)(C)C)=[CH:14][CH:13]=1>C(Cl)Cl>[NH2:20][CH2:19][CH2:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][CH2:10][C:9]([CH3:28])=[O:8])=[CH:13][CH:14]=1 | 3 | ClCCl | O=C(O)C(F)(F)F | null | 25 | null | null |
297,973 | 1,103,208 | O=S(=O)(O)O | null | null | null | ord_dataset-375a420ee9b042918ddca20f02df37d3 | 2011-01-01T00:11:00 | true | Nitric acid (10 mL) was slowly added to sulfuric acid (10 mL) at 0° C., and the mixture was stirred at the same temperature for 10 min. To this solution was slowly added 1-benzothiophene 1,1-dioxide (3.99 g) at 0° C., and the mixture was further stirred at the same temperature for 30 min. The reaction mixture was poure... | O=[N+]([O-])c1ccc2c(c1)S(=O)(=O)C=C2 | null | O=[N+]([O-])O | O=S1(=O)C=Cc2ccccc21 | null | [N+:1]([O-:4])(O)=[O:2].[S:5]1(=[O:15])(=[O:14])[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH:7]=[CH:6]1>S(=O)(=O)(O)O>[N+:1]([C:11]1[CH:12]=[CH:13][C:8]2[CH:7]=[CH:6][S:5](=[O:15])(=[O:14])[C:9]=2[CH:10]=1)([O-:4])=[O:2] | 0.17 | null | null | null | 0 | null | 84 |
717,569 | 495,402 | [H-] | [Na+] | null | null | ord_dataset-9df8b3ec9c8742b3802e0efaac6f6ef3 | 2001-01-01T00:03:00 | true | 2.0 g (4.15 mmol) of 4-{[6-(quinolin-8-yl-sulphonylamino)-1-methyl-2-oxo-1,2-dihydroquinoxalin-3-yl]-methyl}-benzonitrile are dissolved in 150 ml tetrahydrofuran and after the addition of 0.2 g (4.15 mmol) of sodium hydride (50% in oil) stirred for 2 hours at ambient temperature. After the addition of 0.47 ml (4.15 mmo... | COC(=O)CN(c1ccc2c(c1)nc(Cc1ccc(C#N)cc1)c(=O)n2C)S(=O)(=O)c1cccc2cccnc12 | null | Cn1c(=O)c(Cc2ccc(C#N)cc2)nc2cc(NS(=O)(=O)c3cccc4cccnc34)ccc21 | CCOC(=O)CBr | null | [N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[S:11]([NH:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[N:21]([CH3:25])[C:20](=[O:26])[C:19]([CH2:27][C:28]2[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[CH:30][CH:29]=2)=[N:18]3)(=[O:13])=[O:12])[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:39][C:40]([O:42][CH2:43]C)=[O:41]>O1CCCC... | 2 | C1CCOC1 | null | null | 25 | null | null |
533,328 | 500,355 | COc1ccc(C(C)=O)cc1 | COc1ccc([C@H](C)O)cc1 | null | null | ord_dataset-18e9ed24dbd44e98b33bdc22aa7580a8 | 2001-01-01T00:04:00 | true | As shown here, the biochemical conversion reaction of immobilized soy bean protein for the substrate (±)-1-(4-methoxyphenyl)ethanol (200 mg) requires 5 days by going through bioconversion to 4-methoxyacetophenone accompanying sterically selective oxidation of (S)-1-(4-methoxyphenyl)ethanol to obtain 96 mg of (R)-1-(4-m... | COc1ccc([C@@H](C)O)cc1 | null | COc1ccc(C(C)O)cc1 | null | null | [CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([OH:11])[CH3:10])=[CH:5][CH:4]=1.CC(C1C=CC(OC)=CC=1)=O.COC1C=CC([C@@H](O)C)=CC=1>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]([OH:11])[CH3:10])=[CH:5][CH:4]=1 | 120 | null | null | null | null | null | 48 |
244,776 | 673,054 | [I-] | [Na+] | null | null | ord_dataset-e90cd41afe844e49875435eb99903799 | 2005-01-01T00:05:00 | true | 3,4-dimethoxyphenylsulfonyl chloride (2.3 mmol) was dissolved in acetone (60 mL), and then NaI (3.4 g, 23 mmol) and fluoroacetic anhydride (1.45 mL, 6.9 mmol) were added and the mixture was stirred at room temperature for one hour. The reaction solution was concentrated, water was added, extraction was performed with e... | COc1ccc(SSc2ccc(OC)c(OC)c2)cc1OC | null | O=C(CF)OC(=O)CF | COc1ccc(S(=O)(=O)Cl)cc1OC | null | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11](Cl)(=O)=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[Na+].[I-].FC[C:19]([O:21][C:22](=O)[CH2:23]F)=O>CC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11][S:11][C:5]2[CH:6]=[CH:23][C:22]([O:21][CH3:19])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10] | 1 | CC(C)=O | null | null | 25 | null | null |
73,269 | 967,286 | null | null | null | null | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | 2010-01-01T00:06:00 | true | 3,5 difluorophenylacetonitrile (5 g) was dissolved in THF (100 mL) and a solution of BH3 in THF (200 mL of 1 M) was added dropwise. The mixture was refluxed overnight, cooled in an ice bath, and the reaction quenched with methanol (20 mL). The solvent was removed by rotary evaporation and the residue partitioned betwee... | NCCc1cc(F)cc(F)c1 | null | N#CCc1cc(F)cc(F)c1 | null | null | [F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]#[N:11])[CH:5]=[C:6]([F:8])[CH:7]=1>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][NH2:11])[CH:5]=[C:6]([F:8])[CH:7]=1 | null | C1CCOC1 | null | null | null | null | null |
759,184 | 115,117 | null | null | null | null | ord_dataset-d182ca8cf3f34de69c7a38343db8c930 | 1984-01-01T00:03:00 | true | Using the method of Example 15, 1-(p-chlorophenyl)-3-azabicyclo[3.1.0]hexane (Example 1) is reacted with acetyl chloride to give 3-acetyl-1-(p-chlorophenyl)-3-azabicyclo[3.1.0]hexane and then is converted to 1-(p-chlorophenyl)-3-ethyl-3-azabicyclo[3.1.0]hexane which is obtained as a brown oil. | CC(=O)N1CC2CC2(c2ccc(Cl)cc2)C1 | null | Clc1ccc(C23CNCC2C3)cc1 | CC(=O)Cl | null | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]23[CH2:13][CH:12]2[CH2:11][NH:10][CH2:9]3)=[CH:4][CH:3]=1.[C:14](Cl)(=[O:16])[CH3:15]>>[C:14]([N:10]1[CH2:11][CH:12]2[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)([CH2:13]2)[CH2:9]1)(=[O:16])[CH3:15] | null | null | null | null | null | null | null |
884,588 | 588,339 | null | null | null | null | ord_dataset-7a74d48eeefd45aba53e7258f3ae067a | 2003-01-01T00:04:00 | true | Using 6-(dimethylamino)-hexylamine and N-[2-(3-Cyano-1H-indol-5-yl)-ethyl]-4-[2-chloro-pyrimidin-4-yl]-benzamide (reference example 1az) as substrates. MS (ion spray) m/z 510 (M+H)+. | CN(C)CCCCCCNc1nccc(-c2ccc(C(=O)NCCc3ccc4[nH]cc(C#N)c4c3)cc2)n1 | null | CN(C)CCCCCCN | N#Cc1c[nH]c2ccc(CCNC(=O)c3ccc(-c4ccnc(Cl)n4)cc3)cc12 | null | [CH3:1][N:2]([CH3:10])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH2:9].[C:11]([C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([CH2:22][CH2:23][NH:24][C:25](=[O:39])[C:26]3[CH:31]=[CH:30][C:29]([C:32]4[CH:37]=[CH:36][N:35]=[C:34](Cl)[N:33]=4)=[CH:28][CH:27]=3)[CH:20]=2)[NH:15][CH:14]=1)#[N:12]>>[C:11]([C:13]1[C:21]2[C:16](... | null | null | null | null | null | null | null |
274,597 | 50,110 | null | null | null | null | ord_dataset-e5870fef54544989915ccced8dd8d849 | 1979-01-01T00:01:00 | true | Analogously to Example 10, 5-amino-N-(2-hydroxy-1,1-dimethylethyl)-2,4,6-triiodoisophthalamic acid is reacted with hexanedioic acid dichloride in dimethylacetamide, and the reaction mixture is worked up. The thus-obtained product melts at 280°-281° C., with decomposition. | CC(C)(CO)NC(=O)c1c(I)c(NC(=O)CCCCC(=O)Nc2c(I)c(C(=O)O)c(I)c(C(=O)NC(C)(C)CO)c2I)c(I)c(C(=O)O)c1I | null | O=C(Cl)CCCCC(=O)Cl | CC(C)(CO)NC(=O)c1c(I)c(N)c(I)c(C(=O)O)c1I | null | [NH2:1][C:2]1[C:3]([I:21])=[C:4]([C:13]([NH:15][C:16]([CH3:20])([CH3:19])[CH2:17][OH:18])=[O:14])[C:5]([I:12])=[C:6]([C:10]=1[I:11])[C:7]([OH:9])=[O:8].[C:22](Cl)(=[O:30])[CH2:23][CH2:24][CH2:25][CH2:26][C:27](Cl)=[O:28]>CC(N(C)C)=O>[C:22]([NH:1][C:2]1[C:3]([I:21])=[C:4]([C:13]([NH:15][C:16]([CH3:19])([CH3:20])[CH2:17]... | null | CC(=O)N(C)C | null | null | null | null | null |
606,606 | 1,413,310 | null | null | null | null | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | 2014-01-01T00:04:00 | true | According to the method of 1-7 of Example 1, a target compound was prepared from 2-fluoro-N-(2-iodo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenyl)-3-(methylamino)benzamide and 2,2,2-trichloroethoxycarbonylchloride. | CN(C(=O)OCC(Cl)(Cl)Cl)c1cccc(C(=O)Nc2c(I)cc(C(F)(C(F)(F)F)C(F)(F)C(F)(F)F)cc2C(F)(F)F)c1F | null | CNc1cccc(C(=O)Nc2c(I)cc(C(F)(C(F)(F)F)C(F)(F)C(F)(F)F)cc2C(F)(F)F)c1F | O=C(Cl)OCC(Cl)(Cl)Cl | null | [F:1][C:2]1[C:34]([NH:35][CH3:36])=[CH:33][CH:32]=[CH:31][C:3]=1[C:4]([NH:6][C:7]1[C:12]([C:13]([F:16])([F:15])[F:14])=[CH:11][C:10]([C:17]([F:29])([C:22]([F:28])([F:27])[C:23]([F:26])([F:25])[F:24])[C:18]([F:21])([F:20])[F:19])=[CH:9][C:8]=1[I:30])=[O:5].[Cl:37][C:38]([Cl:45])([Cl:44])[CH2:39][O:40][C:41](Cl)=[O:42]>>... | null | null | null | null | null | null | null |
20,395 | 1,745,766 | null | null | null | null | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | 2016-01-01T00:07:00 | true | 4,6-Dichloro-N-(3-fluoro-5-methoxyphenyl)pyrimidine-5-carboxamide (800 mg, 1.42 mmol) was dissolved in dioxane (5 ml) and cooled in an ice bath. Ammonia solution (1 ml, 7N in MeOH) was added dropwise and the mixture was stirred at 0° C. for 6 h and overnight at room temperature. After evaporation of the solvent under r... | COc1cc(F)cc(NC(=O)c2c(N)ncnc2Cl)c1 | null | COc1cc(F)cc(NC(=O)c2c(Cl)ncnc2Cl)c1 | N | null | [Cl:1][C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[C:13]([F:19])[CH:12]=2)=[O:9])=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[NH3:21]>O1CCOCC1>[NH2:21][C:6]1[C:7]([C:8]([NH:10][C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[C:13]([F:19])[CH:12]=2)=[O:9])=[C:2]([Cl:1])[N:3]=[CH:4][N:5]=1 | 8 | C1COCCO1 | null | null | 0 | null | null |
477,885 | 1,488,149 | CCCC[N+](CCCC)(CCCC)CCCC | [F-] | null | null | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | 2014-01-01T00:09:00 | true | To a solution of 8-{[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methoxyphenyl]amino}-N-(2,6-diethylphenyl)-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide (300 mg, 0.48 mmol) in 6 ml of dry THF, 800 μl of commercial TBAF solution in THF were added. The mixture was stirred at room temperature for 1 h ... | CCc1cccc(CC)c1NC(=O)c1nn(C)c2c1CCc1cnc(Nc3ccc(CO)cc3OC)nc1-2 | null | CCc1cccc(CC)c1NC(=O)c1nn(C)c2c1CCc1cnc(Nc3ccc(CO[Si](C)(C)C(C)(C)C)cc3OC)nc1-2 | null | null | [Si]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]2[N:26]=[CH:25][C:24]3[CH2:23][CH2:22][C:21]4[C:27]([C:31]([NH:33][C:34]5[C:39]([CH2:40][CH3:41])=[CH:38][CH:37]=[CH:36][C:35]=5[CH2:42][CH3:43])=[O:32])=[N:28][N:29]([CH3:30])[C:20]=4[C:19]=3[N:18]=2)=[C:12]([O:44][CH3:45])[CH:11]=1)(C(C)(C)C)(C)C>C1COCC1.CCCC... | 1 | C1CCOC1 | null | null | 25 | null | 85 |
864,645 | 704,612 | CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)c2ccccc21 | null | null | null | ord_dataset-c408dfed796e4354b61e312e67f7143f | 2006-01-01T00:04:00 | true | A solution of (R)-2-Cyclohexylmethyl-N-{(S)-1-[hydroxy-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-methyl]-propyl}-4-morpholin-4-yl-4-oxo-butyramide (324 mg, 0.661 mmol) in methylene chloride (10 ml) was treated with Dess Martin periodinane (308 mg, 0.726 mmol) and stirred at room temperature for 90 minutes. The reaction ... | CC[C@H](NC(=O)[C@@H](CC(=O)N1CCOCC1)CC1CCCCC1)C(=O)c1noc(C(F)(F)F)n1 | null | CC[C@H](NC(=O)[C@@H](CC(=O)N1CCOCC1)CC1CCCCC1)C(O)c1noc(C(F)(F)F)n1 | null | null | [CH:1]1([CH2:7][C@H:8]([CH2:26][C:27]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)=[O:28])[C:9]([NH:11][C@H:12]([CH:15]([OH:25])[C:16]2[N:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[O:18][N:17]=2)[CH2:13][CH3:14])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH:1]1(... | 1.5 | ClCCl | null | null | 25 | null | null |
240,518 | 1,249,175 | Cl | null | null | null | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | 2013-01-01T00:01:00 | true | The title compound was prepared as described in Example 1d from 6-chloro-N-{3-[8-(2,6-difluorophenyl)-2-(methylsulfonyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-4-yl]-4-methylphenyl}-3-pyridinecarboxamide and (1H-imidazol-2-ylmethyl)amine dihydrochloride: LC-MS m/z 599 (M+H)+, 1.92 min (ret time). | Cc1ccc(NC(=O)c2ccc(Cl)nc2)cc1-c1nc(NCc2ncc[nH]2)nc2c1ccc(=O)n2-c1c(F)cccc1F | null | Cc1ccc(NC(=O)c2ccc(Cl)nc2)cc1-c1nc(S(C)(=O)=O)nc2c1ccc(=O)n2-c1c(F)cccc1F | NCc1ncc[nH]1 | null | [Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([C:18]3[C:19]4[CH:31]=[CH:30][C:29](=[O:32])[N:28]([C:33]5[C:38]([F:39])=[CH:37][CH:36]=[CH:35][C:34]=5[F:40])[C:20]=4[N:21]=[C:22](S(C)(=O)=O)[N:23]=3)[CH:12]=2)=[O:9])=[CH:4][CH:3]=1.Cl.Cl.[NH:43]1[CH:47]=[CH:46][N:45]=[C:44]1[CH... | null | null | null | null | null | null | null |
305,482 | 497,277 | Cl | null | null | null | ord_dataset-9df8b3ec9c8742b3802e0efaac6f6ef3 | 2001-01-01T00:03:00 | true | Following General Procedure A and using N-(3,5-difluorophenylacetyl)-L-alanine (from Example B2 above) and methyl (S)-2-amino-3-(thiazol-4-yl)propionate hydrochloride (General Procedure H with methanol and HCl on methyl (S)-2-amino-3-(thiazol-4-yl)propyl acid (Synthetech)), the title compound was prepared as a solid (m... | COC(=O)[C@H](Cc1cscn1)NC(=O)[C@H](C)NC(=O)Cc1cc(F)cc(F)c1 | null | C[C@H](NC(=O)Cc1cc(F)cc(F)c1)C(=O)O | COC(=O)[C@@H](N)Cc1cscn1 | null | [F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([NH:12][C@H:13]([C:15]([OH:17])=O)[CH3:14])=[O:11])[CH:5]=[C:6]([F:8])[CH:7]=1.Cl.[NH2:19][C@@H:20]([CH2:25][C:26]1[N:27]=[CH:28][S:29][CH:30]=1)[C:21]([O:23][CH3:24])=[O:22]>CO.C(Cl)Cl>[F:8][C:6]1[CH:5]=[C:4]([CH2:9][C:10]([NH:12][C@H:13]([C:15]([NH:19][C@@H:20]([CH2:25][C:26]2[N:... | null | CO | ClCCl | null | null | null | null |
392,773 | 1,632,215 | null | null | null | null | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | 2015-01-01T00:09:00 | true | Using N-((2S)-1-((2-(4-(benzyloxy)-3,5-difluorophenyl)-1,3-benzoxazol-6-yl)oxy)propan-2-yl)acetamide and iodoethane, and in the same manner as in Example 5, the title compound was obtained. | CCOc1c(F)cc(-c2nc3ccc(OC[C@H](C)NC(C)=O)cc3o2)cc1F | null | CC(=O)N[C@@H](C)COc1ccc2nc(-c3cc(F)c(OCc4ccccc4)c(F)c3)oc2c1 | null | null | [CH2:1]([O:8][C:9]1[C:14]([F:15])=[CH:13][C:12]([C:16]2[O:17][C:18]3[CH:24]=[C:23]([O:25][CH2:26][C@@H:27]([NH:29][C:30](=[O:32])[CH3:31])[CH3:28])[CH:22]=[CH:21][C:19]=3[N:20]=2)=[CH:11][C:10]=1[F:33])[C:2]1C=CC=CC=1.ICC>>[CH2:1]([O:8][C:9]1[C:10]([F:33])=[CH:11][C:12]([C:16]2[O:17][C:18]3[CH:24]=[C:23]([O:25][CH2:26]... | null | CCI | null | null | null | null | null |
563,762 | 387,896 | O=[Pt] | null | null | null | ord_dataset-44d518e567bd4c039d77233023f78bb2 | 1998-01-01T00:01:00 | true | The title compound was prepared by hydrogenation of 5,11-dihydro-3,4-dimethyl-11-ethyl-5-methyl-8-(phenylethynyl)-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one over platinum oxide, as described in Example 42b. The product crystallized from ether/petroleum ether, m.p. 187°-188° C. | CCN1c2ncc(CCc3ccccc3)cc2C(=O)N(C)c2c1ncc(C)c2C | null | CCN1c2ncc(C#Cc3ccccc3)cc2C(=O)N(C)c2c1ncc(C)c2C | null | null | [CH3:1][C:2]1[CH:12]=[N:11][C:10]2[N:9]([CH2:13][CH3:14])[C:8]3[N:15]=[CH:16][C:17]([C:19]#[C:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:18][C:7]=3[C:6](=[O:27])[N:5]([CH3:28])[C:4]=2[C:3]=1[CH3:29]>[Pt]=O>[CH3:1][C:2]1[CH:12]=[N:11][C:10]2[N:9]([CH2:13][CH3:14])[C:8]3[N:15]=[CH:16][C:17]([CH2:19][CH2:20][C... | null | null | null | null | null | null | null |
755,460 | 1,015,220 | null | null | null | null | ord_dataset-f024e9664ab64906a71a2ff6004cb3d0 | 2010-01-01T00:12:00 | true | This was prepared analogously from 2-{1-[1-(3-bromo-phenyl)-1H-benzoimidazol-5-yl]-ethyl}-isoindole-1,3-dione and 5-pyrimidineboronic acid. | CC(c1ccc2c(c1)ncn2-c1cccc(-c2cncnc2)c1)N1C(=O)c2ccccc2C1=O | null | CC(c1ccc2c(c1)ncn2-c1cccc(Br)c1)N1C(=O)c2ccccc2C1=O | OB(O)c1cncnc1 | null | Br[C:2]1[CH:3]=[C:4]([N:8]2[C:12]3[CH:13]=[CH:14][C:15]([CH:17]([N:19]4[C:27](=[O:28])[C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[C:20]4=[O:29])[CH3:18])=[CH:16][C:11]=3[N:10]=[CH:9]2)[CH:5]=[CH:6][CH:7]=1.[N:30]1[CH:35]=[C:34](B(O)O)[CH:33]=[N:32][CH:31]=1>>[N:30]1[CH:35]=[C:34]([C:2]2[CH:3]=[C:4]([N:8]3[C:12]4[CH... | null | null | null | null | null | null | null |
404,815 | 2,616 | O=C([O-])[O-] | [Na+] | null | null | ord_dataset-a0bc986c3cf848c2a1ea93b297d1ad89 | 1976-01-01T00:02:00 | true | A stirred mixture of 8.0 g of (4.6-dichloro-2-pyrimidinylthio)acetic acid ethyl ester, 2.8 g of aniline and 3.2 g of sodium carbonate in 100 ml. of ethanol was heated under reflux for 5 hr. The reaction mixture was filtered and water was added to the filtrate to start precipitation. The crude product was recrystallized... | CCOC(=O)CSc1nc(Cl)cc(Nc2ccccc2)n1 | null | Nc1ccccc1 | CCOC(=O)CSc1nc(Cl)cc(Cl)n1 | null | [CH2:1]([O:3][C:4](=[O:15])[CH2:5][S:6][C:7]1[N:12]=[C:11]([Cl:13])[CH:10]=[C:9](Cl)[N:8]=1)[CH3:2].[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][S:6][C:7]1[N:8]=[C:9]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:10]=[C:11]([Cl:1... | null | CCO | null | null | null | 69.1 | null |
12,353 | 899,471 | c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd-4]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | [Cs+] | [F-] | null | ord_dataset-de6bce51790e4004a27e1a8f2bcc7ded | 2009-01-01T00:08:00 | true | According to the procedure described for example 26b the use of 1-bromo-3-methanesulfonyl-benzene (1.07 g, 4.55 mmol), (E)-3-cyclohexyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol (1.57 g, 5.92 mmol), caesium fluoride (2.07 g, 13.7 mmol) and tetrakis(triphenylphosphino)palladium(0) (525 mg, 455 μmol... | CS(=O)(=O)c1cccc(/C(=C\C2CCCCC2)CO)c1 | null | CS(=O)(=O)c1cccc(Br)c1 | CC1(C)OB(/C(=C\C2CCCCC2)CO)OC1(C)C | null | Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:3]=1.[CH:12]1(/[CH:18]=[C:19](\B2OC(C)(C)C(C)(C)O2)/[CH2:20][OH:21])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.[F-].[Cs+]>O1CCOCC1.C1(P([Pd-4](P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C... | null | C1COCCO1 | null | null | null | 51.7 | null |
30,740 | 89,761 | [Na+] | [OH-] | null | null | ord_dataset-aeb5378e6e67443e8a4f5c7a5ec3de51 | 1981-01-01T00:12:00 | true | To an ice cold solution of 1.60 g (0.04 mol) of NaOH in 45 ml of water is added 9.64 g (0.04 mol) of 5-cyano-1-(2,6-dimethylphenyl)uracil, obtained as in Example 1. After dissolution, 50 ml of ice cold dichloromethane is added, followed by a solution of 9.36 g (0.04 mol) of 1,1,2,2-tetrachloroethanesulphenyl chloride (... | Cc1cccc(C)c1-n1cc(C#N)c(=O)n(SC(Cl)(Cl)C(Cl)Cl)c1=O | null | Cc1cccc(C)c1-n1cc(C#N)c(=O)[nH]c1=O | ClSC(Cl)(Cl)C(Cl)Cl | null | [OH-].[Na+].[C:3]([C:5]1[C:6](=[O:20])[NH:7][C:8](=[O:19])[N:9]([C:11]2[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:18])[CH:10]=1)#[N:4].[Cl:21][C:22]([Cl:28])([S:26]Cl)[CH:23]([Cl:25])[Cl:24].ClCCl>O>[C:3]([C:5]1[C:6](=[O:20])[N:7]([S:26][C:22]([Cl:28])([Cl:21])[CH:23]([Cl:25])[Cl:24])[C:8](=[O:19])[N:9]([C:11]... | 0.5 | ClCCl | O | null | 25 | null | null |
627,780 | 25,292 | CCN1C(=CC#CC2N(CC)c3nc4ccccc4nc3[NH+]2CC)N(CC)c2nc3ccccc3nc21 | [O-][Cl+3]([O-])([O-])[O-] | null | null | ord_dataset-fcf7c02bbb814fe696760b5fbfee16bb | 1977-01-01T00:05:00 | true | Phosphoryl chloride (1.0 ml) is added to a stirred suspension of 1,3-Bis(1-methyl-2-(1H)-quinolylidene)acetone (0.68 g, 0.002 mol) in pyridine (10 ml). The mixture is stirred for 5 min., then the solid is collected and washed with a little pyridine, then with ether. The dye is converted to its perchlorate salt by solut... | CN1C(=CC#Cc2ccc3ccccc3[n+]2C)C=Cc2ccccc21 | null | CN1C(=CC(=O)C=C2C=Cc3ccccc3N2C)C=Cc2ccccc21 | null | null | P(Cl)(Cl)(Cl)=O.[CH3:6][N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]1=[CH:17][C:18]([CH:20]=[C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]1[CH3:31])=O.[Cl:32]([O-:36])(=[O:35])(=[O:34])=[O:33].C([NH+]1C2=NC3C(N=C2N(CC)C1C#CC=C1N(CC)C2=NC4C(N=C2N1CC)=CC=CC=4)=CC=CC... | 0.08 | O=P(Cl)(Cl)Cl | c1ccncc1 | CC#N | null | 35 | null |
130,467 | 560,636 | null | null | null | null | ord_dataset-7c28974b7fcf4c9c86d5f2a42ba328a2 | 2002-01-01T00:09:00 | true | The title compound was prepared from N-[5-((1R)-2-Amino-1-hydroxy-ethyl)-2-hydroxy-phenyl]-methanesulfonamide and Reference Example 14, 1-[4-(4-oxo-piperidin-1-yl)-benzenesulfonyl]-pyrrolidine-2-carboxylic acid isopropyl ester, according to the procedure of Example 1 as an off-white solid; mp 52-58° C.; 1H NMR (300 MHz... | CC(C)OC(=O)C1CCCN1S(=O)(=O)c1ccc(N2CCC(NCC(O)c3ccc(O)c(NS(C)(=O)=O)c3)CC2)cc1 | null | CS(=O)(=O)Nc1cc([C@@H](O)CN)ccc1O | CC(C)OC(=O)C1CCCN1S(=O)(=O)c1ccc(N2CCC(=O)CC2)cc1 | null | [NH2:1][CH2:2][C@@H:3]([C:5]1[CH:6]=[CH:7][C:8]([OH:16])=[C:9]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:10]=1)[OH:4].[CH:17]([O:20][C:21]([CH:23]1[CH2:27][CH2:26][CH2:25][N:24]1[S:28]([C:31]1[CH:36]=[CH:35][C:34]([N:37]2[CH2:42][CH2:41][C:40](=O)[CH2:39][CH2:38]2)=[CH:33][CH:32]=1)(=[O:30])=[O:29])=[O:22])([CH3:19])... | null | null | null | null | null | null | null |
109,351 | 1,756,725 | null | null | null | null | ord_dataset-97eb2ab57fec4160922caae33b54d956 | 2016-01-01T00:08:00 | true | 4-(chlorosulfonyl)benzoic acid (500 mg, 2.27 mmol) was treated with 6-methoxy-1,2,3,4-tetrahydroquinoline (1.0 g, 6.13 mmol) using method A to give 4-(6-methoxy-3,4-dihydroquinolin-1(2H)-ylsulfonyl)benzoic acid as an off-white solid. Yield: 358 mg (46%). 1H-NMR: 8.04 (d, J=8.5 Hz, 2H), 7.64 (d, J=8.5 Hz, 2H), 7.52 (d, ... | COc1ccc2c(c1)CCCN2S(=O)(=O)c1ccc(C(=O)O)cc1 | null | O=C(O)c1ccc(S(=O)(=O)Cl)cc1 | COc1ccc2c(c1)CCCN2 | null | Cl[S:2]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[NH:22][CH2:21][CH2:20][CH2:19]2>>[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[N:22]([S:2]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=... | null | null | null | null | null | null | null |
204,582 | 1,228,110 | [I-] | [Zn+2] | null | null | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | 2012-01-01T00:11:00 | true | To a mixture of 0.83 g of 4-[5-[3,5-bis(trifluoromethyl)phenyl]-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]benzaldehyde and 0.36 g of trimethylsilylcyanide, 0.01 g of zinc iodide was added while stirring the mixture at 0° C. The resultant mixture was stirred at 60° C. for 10 minutes, and then left to be cooled down to... | N#CC(N)c1ccc(C2=NOC(c3cc(C(F)(F)F)cc(C(F)(F)F)c3)(C(F)(F)F)C2)cc1 | null | C[Si](C)(C)C#N | O=Cc1ccc(C2=NOC(c3cc(C(F)(F)F)cc(C(F)(F)F)c3)(C(F)(F)F)C2)cc1 | N | [F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([C:13]2([C:26]([F:29])([F:28])[F:27])[O:17][N:16]=[C:15]([C:18]3[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=3)[CH2:14]2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C[Si]([C:36]#[N:37])(C)C.[NH3:38].CO>[I-].[Zn+2].[I-]>[NH2:38][CH:22]([C:21]1[CH:24]=[CH:25][C:18]([C... | null | CO | null | null | 0 | null | null |
29,434 | 764,662 | CN | null | null | null | ord_dataset-7a8649d55889427e85b208ae89475895 | 2007-01-01T00:04:00 | true | A mixture of 2-{cis-4-[(4-methyl-1-tetrahydro-2H-pyran-2-yl-1H-indazol-5-yl)oxy]cyclohexyl}-1H-isoindole-1,3(2H)-dione (95.5 mg, 0.208 mmol) and a 30% methylamine-ethanol solution (5.0 ml) was stirred with heating under reflux for 2 hours. The reaction solution was allowed to cool, and then was concentrated under reduc... | Cc1c(O[C@H]2CC[C@@H](N)CC2)ccc2c1cnn2C1CCCCO1 | null | Cc1c(O[C@H]2CC[C@@H](N3C(=O)c4ccccc4C3=O)CC2)ccc2c1cnn2C1CCCCO1 | null | null | [CH3:1][C:2]1[C:10]([O:11][C@@H:12]2[CH2:17][CH2:16][C@H:15]([N:18]3C(=O)C4C(=CC=CC=4)C3=O)[CH2:14][CH2:13]2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][O:30]1.CN.C(O)C>>[CH3:1][C:2]1[C:10]([O:11][C@@H:12]2[CH2:13][CH2:14][C@H:15]([NH2:18])[CH2:16][CH2:17]2)=[CH:9][CH:8]=[C:7]2... | null | CCO | null | null | null | null | null |
350,390 | 449,628 | [H-] | [Na+] | null | null | ord_dataset-a4f0b79f6b9847168861270b79f84afa | 1999-01-01T00:11:00 | true | A mixture of 1-[[1-(3,4-dimethoxyphenyl)cyclopropyl]methyl]-1,3-dihydro-2H-imidazol-2-one (1.9 g) in DMF (20 ml) was stirred at RT. Sodium hydride (60%) (0.28 g) was added portionwise over 15 minutes. The mixture was stirred for 30 minutes. A solution of bromomethylbenzene (1.45 g) in DMF (5 ml) was added dropwise over... | COc1ccc(C2(Cn3ccn(Cc4ccccc4)c3=O)CC2)cc1OC | null | BrCc1ccccc1 | COc1ccc(C2(Cn3cc[nH]c3=O)CC2)cc1OC | null | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2([CH2:14][N:15]3[CH:19]=[CH:18][NH:17][C:16]3=[O:20])[CH2:13][CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[H-].[Na+].Br[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2([CH2:14][N:15]3[CH:19]=[CH:18][N:17]([CH2:24][C:25]4[CH:30]=[... | null | CN(C)C=O | null | null | 25 | null | 51.5 |
512,871 | 1,465,539 | [Na+] | [OH-] | null | null | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | 2014-01-01T00:08:00 | true | A solution of 1.5 g (3.59 mmol) of 4-{2-[4-(3-carboxyphenyl)piperazin-1-yl]ethyl}piperidine-1-carboxylic acid tert-butyl ester in 20 mL of dry tetrahydrofuran is cooled to −10° C. under argon. An addition of 11 mL of a 1M solution of boranetetrahydrofuran complex in tetrahydrofuran is performed at −10° C. Stirring is m... | CC(C)(C)OC(=O)N1CCC(CCN2CCN(c3cccc(CO)c3)CC2)CC1 | null | CC(C)(C)OC(=O)N1CCC(CCN2CCN(c3cccc(C(=O)O)c3)CC2)CC1 | null | null | [C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28](O)=[O:29])[CH:23]=3)[CH2:18][CH2:17]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][N:16]2[CH2:... | null | C1CCOC1 | null | null | 25 | 69 | null |
728,187 | 216,123 | Br | null | null | null | ord_dataset-67ed03c283094854909157b1038e38e3 | 1990-01-01T00:10:00 | true | 1.21 g (7.6 mmol) of bromine in 5 ml of glacial acetic acid are added to a solution of 1.2 g (7.5 mmol) of 5-acetylbenzimidazole and 1.35 g of 48% strength aqueous HBr (=8 mmol of HB) in 15 ml of glacial acetic acid at room temperature. The mixture is stirred at 40° C. for 30 minutes and cooled and the product which ha... | O=C(CBr)c1ccc2nc[nH]c2c1 | null | CC(=O)c1ccc2nc[nH]c2c1 | BrBr | null | [Br:1]Br.[C:3]([C:6]1[CH:14]=[CH:13][C:9]2[N:10]=[CH:11][NH:12][C:8]=2[CH:7]=1)(=[O:5])[CH3:4].[BrH:15]>C(O)(=O)C>[BrH:1].[Br:15][CH2:4][C:3]([C:6]1[CH:14]=[CH:13][C:9]2[N:10]=[CH:11][NH:12][C:8]=2[CH:7]=1)=[O:5] | 0.5 | CC(=O)O | null | null | 40 | null | null |
260,182 | 275,000 | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | ord_dataset-02ee2261663048188cf6d85d2cc96e3f | 1993-01-01T00:09:00 | true | 3-Ethenylbenzyl alcohol (5.26 g) was dissolved in carbon tetrachloride (100 ml) and triphenylphosphine (10.2 g) added. The solution was refluxed overnight and then left to cool. A white precipitate formed which was filtered through celite. The filtrate was evaporated in vacuo to yield a crude product. The residue was p... | C=Cc1cccc(CCl)c1 | null | C=Cc1cccc(CO)c1 | ClC(Cl)(Cl)Cl | null | [CH:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6]O)=[CH2:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:31]>>[CH:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][Cl:31])=[CH2:2] | null | null | null | null | null | null | null |
722,732 | 531,825 | null | null | null | null | ord_dataset-7774db17e619477ea20ee621abe71257 | 2002-01-01T00:01:00 | true | To a solution of the diamine of Step A (3.28 g) in dry chloroform (48 mL) was added dropwise under nitrogen at 0° C. triethylamine (3.62 mL). Thiophosgene (1.49 mL) was then added dropwise via syringe and the mixture was stirred in the cold for another 15 minutes. Stirring was continued at room temperature for 1.5 hour... | Cc1cccc(Cl)c1N1CCCN(C2CCC2)C1=S | null | Cc1cccc(Cl)c1NCCCNC1CCC1 | S=C(Cl)Cl | null | [Cl:1][C:2]1[C:7]([NH:8][CH2:9][CH2:10][CH2:11][NH:12][CH:13]2[CH2:16][CH2:15][CH2:14]2)=[C:6]([CH3:17])[CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:25](Cl)(Cl)=[S:26].O>C(Cl)(Cl)Cl>[Cl:1][C:2]1[C:7]([N:8]2[CH2:9][CH2:10][CH2:11][N:12]([CH:13]3[CH2:16][CH2:15][CH2:14]3)[C:25]2=[S:26])=[C:6]([CH3:17])[CH:5]=[CH:4][CH:3]=1 | 0.25 | ClC(Cl)Cl | CCN(CC)CC | O | null | null | 81 |
594,519 | 515,028 | null | null | null | null | ord_dataset-41760195182e4bb4bc779bd722456071 | 2001-01-01T00:08:00 | true | The title compound was prepared according to the procedure described in step 2 of Example 1 from 2-[(ethoxycarbonyl)amino]-4fluorobenzonitrile (step 1) and 2-bromoacetophenone. | CCOC(=O)n1c(C(=O)c2ccccc2)c(N)c2ccc(F)cc21 | null | CCOC(=O)Nc1cc(F)ccc1C#N | O=C(CBr)c1ccccc1 | null | [CH2:1]([O:3][C:4]([NH:6][C:7]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:8]=1[C:9]#[N:10])=[O:5])[CH3:2].Br[CH2:17][C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:19]>>[NH2:10][C:9]1[C:8]2[C:7](=[CH:14][C:13]([F:15])=[CH:12][CH:11]=2)[N:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:17]=1[C:18](=[O:19])[C:20]1[CH:25]=[... | null | null | null | null | null | null | null |
343,996 | 79,849 | C[O-] | [Na+] | null | null | ord_dataset-2d589ad46f82417ab9ddc07f7655411c | 1981-01-01T00:04:00 | true | To a solution of 1.42 g. sodium methoxide in 250 ml. methanol is added 8.0 g. of 4-[2-(1-naphthyloxy)ethylamino]benzoic acid. After one-half hour, the mixture is concentrated under vacuum to a solid which is washed with methanol and then CH2Cl2. This solid is immediately dried in a vacuum oven to minimize absorption of... | O=C([O-])c1ccc(NCCOc2cccc3ccccc23)cc1 | null | O=C(O)c1ccc(NCCOc2cccc3ccccc23)cc1 | null | null | C[O-].[Na+:3].[C:4]1([O:14][CH2:15][CH2:16][NH:17][C:18]2[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=2)[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1>CO>[C:4]1([O:14][CH2:15][CH2:16][NH:17][C:18]2[CH:19]=[CH:20][C:21]([C:22]([O-:24])=[O:23])=[CH:25][CH:26]=2)[C:13]2[C:8](=[CH:9][CH:... | null | CO | null | null | null | null | null |
350,802 | 1,392,605 | CC(C)OC(=O)N=NC(=O)OC(C)C | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | ord_dataset-12dc3bd21bcf44d09e5b4249afe15161 | 2014-01-01T00:02:00 | true | A mixture of 2-(1-methyl-1H-pyrazol-5-yl)ethanol (1.00 g), 4-hydroxybenzotrifluoride (2.57 g), 1.9 M diisopropyl azodicarboxylate (6.26 mL, toluene solution), triphenylphosphine (3.12 g) and tetrahydrofuran (50 mL) was stirred at a room temperature for 2 days. Thereafter, water was added to the reaction solution, and t... | Cn1nccc1CCOc1ccc(C(F)(F)F)cc1 | null | Cn1nccc1CCO | Oc1ccc(C(F)(F)F)cc1 | null | [CH3:1][N:2]1[C:6]([CH2:7][CH2:8][OH:9])=[CH:5][CH:4]=[N:3]1.O[C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O.O1CCCC1>[CH3:1][N:2]1[C:6]([CH2:7][CH2:8][O:9][C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][... | 48 | C1CCOC1 | O | null | 25 | 54.6 | null |
166,508 | 72,553 | null | null | null | null | ord_dataset-520610070b3c4780a03b44c7fcecc28f | 1980-01-01T00:10:00 | true | A solution of 4.75 g. of N-trifluoroacetyl-4-(4-tetradecenylamino)benzoyl chloride and 1.2 g. of triethylamine in 200 ml. of warm ether is treated with 1.55 g. alanine ethyl ester and refluxed for 24 hours. The hot solution is filtered, the residue is washed with hot ether, and the combined filtrate and washings are ev... | CCCCCCCCCC=CCCCNc1ccc(C(=O)N[C@@H](C)C(=O)O)cc1 | null | CCOC(=O)[C@H](C)N | CCCCCCCCCC=CCCCN(C(=O)C(F)(F)F)c1ccc(C(=O)Cl)cc1 | null | FC(F)(F)C([N:5]([CH2:15][CH2:16][CH2:17][CH:18]=[CH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:6]1[CH:14]=[CH:13][C:9]([C:10](Cl)=[O:11])=[CH:8][CH:7]=1)=O.C(N(CC)CC)C.C([O:40][C:41](=[O:45])[C@H:42]([CH3:44])[NH2:43])C>CCOCC>[CH2:15]([NH:5][C:6]1[CH:7]=[CH:8][C:9]([C:10]([NH:43][C@H... | null | CCN(CC)CC | CCOCC | null | null | null | null |
154,482 | 1,387,562 | null | null | null | null | ord_dataset-31641fb65b34430fa7435229b949b604 | 2014-01-01T00:01:00 | true | 2-{6-[8-(2-Methoxy-5-trifluoromethyl-phenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-ylamino]-3,4-dihydro-1H-isoquinolin-2-yl}-N,N-dimethyl-acetamide was prepared from [8-(2-methoxy-5-trifluoromethyl-phenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-yl]-(1,2,3,4-tetrahydro-isoquinolin-6-yl)-amine (0.150 g, 0.341 mmol) and 2-chloro-N,N... | COc1ccc(C(F)(F)F)cc1-c1cccn2nc(Nc3ccc4c(c3)CCN(CC(=O)N(C)C)C4)nc12 | null | COc1ccc(C(F)(F)F)cc1-c1cccn2nc(Nc3ccc4c(c3)CCNC4)nc12 | CN(C)C(=O)CCl | null | [CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:4]=1[C:13]1[C:14]2[N:15]([N:19]=[C:20]([NH:22][C:23]3[CH:24]=[C:25]4[C:30](=[CH:31][CH:32]=3)[CH2:29][NH:28][CH2:27][CH2:26]4)[N:21]=2)[CH:16]=[CH:17][CH:18]=1.Cl[CH2:34][C:35]([N:37]([CH3:39])[CH3:38])=[O:36]>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:... | null | null | null | null | null | null | null |
390,321 | 595,376 | null | null | null | null | ord_dataset-278fb6af8a994ac69e4d95e6e6eff756 | 2003-01-01T00:05:00 | true | To a solution of 2-chloro-5-nitropyridine (30 mmol, 5.0 g) in absolute ethanol was added a solution of hydrazine hydrate (320 mmol, 15.8 g) in ethanol using syringe pump. At the end of the addition, the reaction was refrigerated. The named product precipitated from the reaction medium, was collected by filtration, and ... | NNc1ccc([N+](=O)[O-])cn1 | null | NN | O=[N+]([O-])c1ccc(Cl)nc1 | null | Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.O.[NH2:12][NH2:13]>C(O)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:12][NH2:13])=[N:3][CH:4]=1)([O-:10])=[O:9] | null | CCO | O | null | null | null | null |
210,529 | 1,395,602 | Cl | [Li+] | [OH-] | null | ord_dataset-12dc3bd21bcf44d09e5b4249afe15161 | 2014-01-01T00:02:00 | true | To a mixture of EtOH (0.2 mL) and H2O (0.1 mL) was suspended ethyl 5-hydroxy-4-[1-hydroxyimino-3-[3-propyl-6-(trifluoromethyl)-benzothiophen-2-yl]propyl]-2-methylphenoxyacetate (7.5 mg, 0.0143 mmol) obtained above. After the addition of lithium hydroxide monohydrate (1.8 mg, 0.0429 mmol), the mixture was heated for 1 h... | CCCc1c(CCC(=NO)c2cc(C)c(OCC(=O)O)cc2O)sc2cc(C(F)(F)F)ccc12 | null | CCCc1c(CCC(=NO)c2cc(C)c(OCC(=O)OCC)cc2O)sc2cc(C(F)(F)F)ccc12 | null | null | CCO.[OH:4][C:5]1[C:6]([C:19](=[N:38][OH:39])[CH2:20][CH2:21][C:22]2[S:23][C:24]3[CH:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[CH:30][C:25]=3[C:26]=2[CH2:27][CH2:28][CH3:29])=[CH:7][C:8]([CH3:18])=[C:9]([CH:17]=1)[O:10][CH2:11][C:12]([O:14]CC)=[O:13].O.[OH-].[Li+].Cl>O>[OH:4][C:5]1[C:6]([C:19](=[N:38][OH:39])[CH2... | null | O | CCO | null | 25 | null | 112.9 |
187,619 | 1,511,149 | null | null | null | null | ord_dataset-1a1aa5d1c3224edca0aec6e3398da985 | 2014-01-01T00:11:00 | true | tert-Butyl 4-(quinolin-8-yl)piperazine-1-carboxylate (2.4 g, 7.66 mmol) was dissolved in methanol (50 ml) and SOCl2 was added to the solution dropwise at 0° C. The resulting solution was refluxed for 1 day and evaporated under reduced pressure. EtOAc (50 ml) was added to the residue and stirred for 2 hours to produce l... | Cl | c1cnc2c(N3CCNCC3)cccc2c1 | O=S(Cl)Cl | CC(C)(C)OC(=O)N1CCN(c2cccc3cccnc23)CC1 | null | [N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N:11]2[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]2)[CH:4]=[CH:3][CH:2]=1.O=S(Cl)[Cl:26]>CO>[ClH:26].[N:11]1([C:9]2[CH:8]=[CH:7][CH:6]=[C:5]3[C:10]=2[N:1]=[CH:2][CH:3]=[CH:4]3)[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1 | 2 | CO | null | null | null | null | null |
164,256 | 1,581,679 | Cl | null | null | null | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | 2015-01-01T00:05:00 | true | Prepared from 5-(4-Methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophene-2-carboxylic acid and 4-N-Boc-2-(R)-methyl-piperazine by the method described in Example 2 Method B. The reaction mixture was evaporated to a solid, triturated and filtered with the aid of water, then washed with a 1 N aqueous hydrochloric acid soluti... | Cc1c(-c2ccc(C(=O)N3CCNC[C@H]3C)s2)noc1C(F)(F)F | null | Cc1c(-c2ccc(C(=O)O)s2)noc1C(F)(F)F | C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1 | null | [CH3:1][C:2]1[C:3]([C:11]2[S:15][C:14]([C:16]([OH:18])=O)=[CH:13][CH:12]=2)=[N:4][O:5][C:6]=1[C:7]([F:10])([F:9])[F:8].C([N:26]1[CH2:31][CH2:30][NH:29][C@H:28]([CH3:32])[CH2:27]1)(OC(C)(C)C)=O.[ClH:33]>O1CCOCC1>[ClH:33].[CH3:32][C@@H:28]1[CH2:27][NH:26][CH2:31][CH2:30][N:29]1[C:16]([C:14]1[S:15][C:11]([C:3]2[C:2]([CH3:... | 2 | C1COCCO1 | null | null | null | 86 | null |
464,205 | 761,382 | null | null | null | null | ord_dataset-2e58cb8db2bf482bbea23283b7e04488 | 2007-01-01T00:03:00 | true | 1-(2-Amino-4,5-dimethoxy-phenyl)-2-(3,4-dichloro-phenyl)-ethanone (5.52 g, 16.24 mmol) was dissolved in dichloromethane (20 ml), distilled water was then added (2 ml) and the resulting solution was cooled at −5° C. under nitrogen. Bromoacetylbromide (1.63 ml, 18.68 mmol) was dissolved in dichloromethane (10 ml) and add... | COc1cc(NC(=O)CBr)c(C(=O)Cc2ccc(Cl)c(Cl)c2)cc1OC | null | COc1cc(N)c(C(=O)Cc2ccc(Cl)c(Cl)c2)cc1OC | O=C(Br)CBr | null | [NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1[C:12](=[O:22])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=1.[Br:23][CH2:24][C:25](Br)=[O:26]>ClCCl>[Br:23][CH2:24][C:25]([NH:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1[C:12](=[O:22])[CH2:13][C:... | 0.25 | ClCCl | null | null | -5 | 70.1 | null |
195,649 | 1,469,717 | null | null | null | null | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | 2014-01-01T00:08:00 | true | The compound prepared in Example 126 (1.00 g) was suspended in tetrahydrofuran (20 mL) and dimethylamine (2 M) (7.66 mL) added and the reaction mixture stirred at room temperature for 3 hours. The reaction mixture was partitioned between saturated aqueous sodium bicarbonate and ethyl acetate. The organics were washed w... | CCOC(=O)c1sc(-c2ccccc2)nc1CN(C)C | null | CCOC(=O)c1sc(-c2ccccc2)nc1CBr | CNC | null | Br[CH2:2][C:3]1[N:4]=[C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[S:6][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[CH3:19][NH:20][CH3:21]>O1CCCC1>[CH3:19][N:20]([CH2:2][C:3]1[N:4]=[C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[S:6][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:21] | 3 | C1CCOC1 | null | null | 25 | null | null |
498,286 | 419,882 | C[O-] | Cc1ccc(S(=O)(=O)O)cc1 | [Na+] | null | ord_dataset-94e21e9990034c729ea727e7d2ab0eb0 | 1998-01-01T00:12:00 | true | 21.1 g (114 mmol) of 4-bromobenzaldehyde and 20 ml (182 mmol) of trimethyl orthoformate (both Fluka, Buchs, Switzerland) are dissolved in 35 ml of methanol, and 0.65 g (3.4 mmol) of p-toluenesulfonic acid monohydrate is added at room temperature (exothermic reaction). The reaction mixture is stirred at room temperature... | COC(OC)c1ccc(Br)cc1 | null | COC(OC)OC | O=Cc1ccc(Br)cc1 | null | [Br:1][C:2]1[CH:9]=[CH:8][C:5](C=O)=[CH:4][CH:3]=1.[CH:10](OC)([O:13][CH3:14])[O:11][CH3:12].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C[O-].[Na+]>CO>[CH3:12][O:11][CH:10]([O:13][CH3:14])[C:5]1[CH:8]=[CH:9][C:2]([Br:1])=[CH:3][CH:4]=1 | 20 | CO | O | null | 25 | null | null |
831,299 | 1,605,142 | [Fe] | [Cl-] | [NH4+] | null | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | 2015-01-01T00:07:00 | true | Iron (2.41 g, 42.3 mmol) and ammonium chloride (2.58 g, 48.4 mmol) are added to a solution of 5-nitro-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridine (3 g, 12 mmol) in ethanol/THF/H2O (4:2:1, 35 mL). The mixture is heated at 100° C. for 2 h. The iron is removed by filtration through pad of Celite® and the filtr... | Nc1cnc2c(cnn2C2CCOCC2)c1 | null | O=[N+]([O-])c1cnc2c(cnn2C2CCOCC2)c1 | null | null | [Cl-].[NH4+].[N+:3]([C:6]1[CH:7]=[C:8]2[CH:14]=[N:13][N:12]([CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[C:9]2=[N:10][CH:11]=1)([O-])=O>C(O)C.C1COCC1.O.[Fe]>[O:18]1[CH2:17][CH2:16][CH:15]([N:12]2[C:9]3=[N:10][CH:11]=[C:6]([NH2:3])[CH:7]=[C:8]3[CH:14]=[N:13]2)[CH2:20][CH2:19]1 | null | O | C1CCOC1 | CCO | 100 | null | 108.8 |
729,905 | 4,309 | null | null | null | null | ord_dataset-a5669edbeffe43bf8514c1bfede8f882 | 1976-01-01T00:04:00 | true | 69 g of bromine were added to a mixture of 69.2 g of 4-ethoxycarbonyl-4-thiazoline-2-one in 500 ml of chloroform and the mixture was refluxed for 20 hours. The mixture was distilled to dryness under reduced pressure and after the addition of isopropyl ether, the mixture was vacuum filtered to obtain 75.2 g of 5-bromo-4... | CCOC(=O)c1[nH]c(=O)sc1Br | null | CCOC(=O)c1csc(=O)[nH]1 | BrBr | null | [Br:1]Br.[CH2:3]([O:5][C:6]([C:8]1[NH:9][C:10](=[O:13])[S:11][CH:12]=1)=[O:7])[CH3:4]>C(Cl)(Cl)Cl>[Br:1][C:12]1[S:11][C:10](=[O:13])[NH:9][C:8]=1[C:6]([O:5][CH2:3][CH3:4])=[O:7] | null | ClC(Cl)Cl | null | null | null | null | 74.7 |
642,869 | 1,141,391 | Cn1c(=O)c2c(-c3cc(F)ccc3Br)c(CN)c(N3CCOCC3)nc2n(C)c1=O | null | null | null | ord_dataset-68715347640045adb1b09e6a04722b0e | 2012-01-01T00:03:00 | true | The title compound was prepared from Compound 47a (Example and 1,2-diphenylethanamine, according to procedure described in the synthesis of Compound 47. MS [m+H] calc'd C30H28BrFN5O2 588; found 588. | Cn1c(=O)c2c(-c3cc(F)ccc3Br)c(CN)c(NC(Cc3ccccc3)c3ccccc3)nc2n(C)c1=O | null | Cn1c(=O)c2c(-c3cc(F)ccc3Br)c(C#N)c(Cl)nc2n(C)c1=O | NC(Cc1ccccc1)c1ccccc1 | null | [Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[C:18]2[C:17](=[O:19])[N:16]([CH3:20])[C:15](=[O:21])[N:14]([CH3:22])[C:13]=2[N:12]=[C:11](Cl)[C:10]=1[C:24]#[N:25].[C:26]1([CH:32]([NH2:40])[CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.NCC1C(N2CCOCC2)=NC2N(C)C(=O... | null | null | null | null | null | null | null |
208,370 | 885,939 | [H-] | [Na+] | null | null | ord_dataset-d728a2f811c0424cbcdb5a84d02b93ae | 2009-01-01T00:06:00 | true | To a cooled (0° C.) suspension of NaH (45 mg, 1.1 mmol, 60% w/w in mineral oil) in DMF (0.5 ml) is added a solution of 2-Methyl-3-{4-[2-(3-methyl-2-oxo-imidazolidin-4-yl)-ethoxy]-phenyl}-2-phenoxy-propionic acid ethyl ester (320 mg, 0.75 mmol) in DMF (1.5 ml). After 5 minutes, the reaction mixture is removed from the c... | CCOC(=O)C(C)(Cc1ccc(OCCC2CN(Cc3ccc(C(=O)c4ccccc4)cc3)C(=O)N2C)cc1)Oc1ccccc1 | null | CCOC(=O)C(C)(Cc1ccc(OCCC2CNC(=O)N2C)cc1)Oc1ccccc1 | O=C(c1ccccc1)c1ccc(CBr)cc1 | null | [H-].[Na+].[CH2:3]([O:5][C:6](=[O:33])[C:7]([CH3:32])([O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH:18]2[CH2:22][NH:21][C:20](=[O:23])[N:19]2[CH3:24])=[CH:11][CH:10]=1)[CH3:4].Br[CH2:35][C:36]1[CH:49]=[CH:48][C:39]([C:40]([C:42]2[CH:47]=[CH:46][CH:45]=... | 0.08 | CN(C)C=O | null | null | 25 | null | 10.9 |
550,139 | 35,539 | O=C([O-])[O-] | [K+] | null | null | ord_dataset-c8db783fb93842e89cdcd41afa59a141 | 1978-01-01T00:01:00 | true | A mixture of 7.6 g of the product of Step A, 9.5 g of diethyl chlorothiophosphate and 7 g of potassium carbonate in 50 ml of acetone was stirred overnight at room temperature and the mixture was then filtered. The filtrate was concentrated by evaporation under reduced pressure and was chromatographed over silica. Eluti... | CCOP(=S)(OCC)Oc1nsc(SC)n1 | null | CCOP(=S)(Cl)OCC | CSc1nc(O)ns1 | null | [OH:1][C:2]1[N:6]=[C:5]([S:7][CH3:8])[S:4][N:3]=1.[P:9](Cl)([O:14][CH2:15][CH3:16])([O:11][CH2:12][CH3:13])=[S:10].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:12]([O:11][P:9]([O:1][C:2]1[N:6]=[C:5]([S:7][CH3:8])[S:4][N:3]=1)([O:14][CH2:15][CH3:16])=[S:10])[CH3:13] | 8 | CC(C)=O | null | null | 25 | null | null |
410,107 | 1,375,730 | [Pt] | null | null | null | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | 2013-01-01T00:12:00 | true | 4-Bromo-3-methyl-2-nitrophenol (10 g, 43.1 mmol) was dissolved in methanol (254 ml), purged with nitrogen and loaded with Pt/C (1.013 g, 10.13 mmol). The reaction was stirred under 60 psi of hydrogen for 5 hours. When complete, the reaction was filtered carefully on Celite™. The top was covered by more Celite™, flushed... | Cc1c(Br)ccc(O)c1N | null | [H][H] | Cc1c(Br)ccc(O)c1[N+](=O)[O-] | null | [Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([N+:9]([O-])=O)[C:3]=1[CH3:12].[H][H]>CO.[Pt]>[NH2:9][C:4]1[C:3]([CH3:12])=[C:2]([Br:1])[CH:7]=[CH:6][C:5]=1[OH:8] | null | CO | null | null | null | 98.8 | null |
393,786 | 1,749,047 | CN(C)C(On1nnc2cccnc21)=[N+](C)C | F[P-](F)(F)(F)(F)F | null | null | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | 2016-01-01T00:07:00 | true | 66 mg (0.228 mmol) of the compound of Example 6A and 74 mg (0.228 mmol) of the compound of Example 32A were dissolved in 1.5 ml of anhydrous DMF, and 104 mg (0.273 mmol) of HATU and 48 μl (0.273 mmol) of N,N-diisopropylethylamine were added in succession. The reaction mixture was stirred at RT for 4 h and then separate... | Cc1ccc(NC(=O)c2cc(S(C)(=O)=O)cc(S(F)(F)(F)(F)F)c2)cc1-n1ccn2nc(-c3cccnc3)cc12 | null | Cc1ccc(N)cc1-n1ccn2nc(-c3cccnc3)cc12 | CS(=O)(=O)c1cc(C(=O)O)cc(S(F)(F)(F)(F)F)c1 | null | [CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N:9]1[C:16]2[N:12]([N:13]=[C:14]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH:15]=2)[CH:11]=[CH:10]1.[CH3:23][S:24]([C:27]1[CH:28]=[C:29]([CH:33]=[C:34]([S:36]([F:41])([F:40])([F:39])([F:38])[F:37])[CH:35]=1)[C:30](O)=[O:31])(=[O:26])=[O:25].CN(C(ON1N=NC2C=CC=... | 4 | CCN(C(C)C)C(C)C | CN(C)C=O | null | 25 | null | null |
637,694 | 1,222,283 | null | null | null | null | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | 2012-01-01T00:11:00 | true | To a solution of 6-(3-nitrophenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-amine (3.49 g, 12.9 mmol) in N,N-dimethylacetamide (20 mL) was added with stirring under ice-cooling cyclopropanecarbonyl chloride (2.46 mL, 27.0 mmol), and the mixture was stirred at room temperature for 15 hr. Water (40 mL) was added to the reaction m... | O=C(Nc1nc2ccc(Oc3cccc([N+](=O)[O-])c3)cn2n1)C1CC1 | null | O=C(Cl)C1CC1 | Nc1nc2ccc(Oc3cccc([N+](=O)[O-])c3)cn2n1 | null | [N+:1]([C:4]1[CH:5]=[C:6]([CH:18]=[CH:19][CH:20]=1)[O:7][C:8]1[CH:9]=[CH:10][C:11]2[N:12]([N:14]=[C:15]([NH2:17])[N:16]=2)[CH:13]=1)([O-:3])=[O:2].[CH:21]1([C:24](Cl)=[O:25])[CH2:23][CH2:22]1.O>CN(C)C(=O)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:18]=[CH:19][CH:20]=1)[O:7][C:8]1[CH:9]=[CH:10][C:11]2[N:12]([N:14]=[C:15]([NH:17][C:... | null | CC(=O)N(C)C | O | null | null | null | 88.2 |
828,787 | 318,202 | O=C([O-])[O-] | [K+] | null | null | ord_dataset-eb32c2b9cbdf4fc39ce6c9fe0fa11430 | 1995-01-01T00:10:00 | true | Isovanillin (50 g, 0.328 mol) is placed in a 1 liter round bottom flask which is equipped with a stir bar and reflux condensor and is charged with 500 ml of dimethylformamide. Potassium carbonate (45.3 g, 0.328 mol) is added to the reaction mixture which is heated to 80° C. At this temperature exo-2-bromonorbornane (12... | COc1ccc(C=O)c(OC2CC3CCC2C3)c1 | null | BrC1CC2CCC1C2 | CN(C)C=O | COc1ccc(C=O)cc1O | [O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:7]([O:8][CH3:9])=[C:5](O)[CH:4]=1.CN(C)[CH:14]=[O:15].C(=O)([O-])[O-].[K+].[K+].[CH2:23]1[CH:27]2C[CH:29](Br)[CH:25]([CH2:26]2)[CH2:24]1>O>[CH:27]12[CH2:26][CH:25]([CH2:24][CH2:23]1)[CH2:29][CH:14]2[O:15][C:4]1[CH:5]=[C:7]([O:8][CH3:9])[CH:10]=[CH:11][C:3]=1[CH:2]=[O:1] | null | O | null | null | 80 | null | null |
356,102 | 879,957 | Cl | null | null | null | ord_dataset-3592bd645cd143ee8274cd0d834ae581 | 2009-01-01T00:05:00 | true | Trans-3-[4-aminocyclohexylcarbonylamino]-N-(4-chlorophenyl)benzofuran-2-carboxamide hydrochloride (150 mg) obtained in Example 225 is suspended in acetonitrile/methanol (5/1, 6 ml), and thereto is added triethylamine (93 μl), and the mixture is stirred at room temperature for several minutes. The reaction solution is c... | O=C(Nc1ccc(Cl)cc1)c1oc2ccccc2c1NC(=O)[C@H]1CC[C@H](NCCO)CC1 | null | OCCI | N[C@H]1CC[C@H](C(=O)Nc2c(C(=O)Nc3ccc(Cl)cc3)oc3ccccc23)CC1 | null | Cl.[NH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([NH:11][C:12]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[O:14][C:13]=2[C:21]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)=[O:22])=[O:10])[CH2:5][CH2:4]1.C(N(CC)CC)C.I[CH2:39][CH2:40][OH:41]>C(Cl)(Cl)Cl.CO>[OH:41][CH2:40][CH2:39][NH:2][C@H:3]1[CH2:8][CH2... | null | CO | CCN(CC)CC | ClC(Cl)Cl | 25 | null | null |
101,191 | 1,394,935 | null | null | null | null | ord_dataset-12dc3bd21bcf44d09e5b4249afe15161 | 2014-01-01T00:02:00 | true | The title compound was synthesized in analogy to Example 1 using 5-(4-chlorophenyl)-6-(2,2,2-trifluoroethoxy)-3-pyridinecarboxylic acid (CAN 1018782-82-5) and 4-(t-butyl-dimethyl-silanyloxymethyl)-piperidin-1-ylamine trifluoroacetate (1:1) as starting materials; the silyl protecting group was lost during reaction and w... | O=C(NN1CCC(CCO)CC1)c1cnc(OCC(F)(F)F)c(-c2ccc(Cl)cc2)c1 | null | O=C(O)C(F)(F)F | O=C(O)c1cnc(OCC(F)(F)F)c(-c2ccc(Cl)cc2)c1 | CC(C)(C)[SiH2]OC(C)(C)C1CCN(N)CC1 | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:20]([OH:22])=O)[CH:11]=[N:12][C:13]=2[O:14][CH2:15][C:16]([F:19])([F:18])[F:17])=[CH:4][CH:3]=1.F[C:24](F)(F)[C:25]([OH:27])=O.C([SiH2]OC(C)(C)[CH:37]1[CH2:42][CH2:41][N:40]([NH2:43])[CH2:39][CH2:38]1)(C)(C)C>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:20... | null | null | null | null | null | null | null |
694,949 | 1,500,354 | null | null | null | null | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | 2014-01-01T00:10:00 | true | The mixture of 2,4,6-trichloroquinoline (300 mg, 1.29 mmol), 7-bromo-2,3,4,5-tetrahydro-1H-2-benzazepine (291 mg, 1.29 mmol) and n-butanol (3 mL) was heated with stirring in a 10 mL microwave process vial for 1 hour at 160° C. under microwave irradiation. The mixture was cooled to room temperature and diluted with ethy... | Clc1ccc2nc(N3CCCc4cc(Br)ccc4C3)cc(Cl)c2c1 | null | Clc1ccc2nc(Cl)cc(Cl)c2c1 | Brc1ccc2c(c1)CCCNC2 | null | Cl[C:2]1[CH:11]=[C:10]([Cl:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:13])[CH:8]=2)[N:3]=1.[Br:14][C:15]1[CH:16]=[CH:17][C:18]2[CH2:24][NH:23][CH2:22][CH2:21][CH2:20][C:19]=2[CH:25]=1.C(O)CCC>C(OCC)(=O)C>[Br:14][C:15]1[CH:16]=[CH:17][C:18]2[CH2:24][N:23]([C:2]3[CH:11]=[C:10]([Cl:12])[C:9]4[C:4](=[CH:5][CH:6]=[C:7]([Cl:13]... | 1 | CCCCO | CCOC(C)=O | null | 160 | 40.8 | null |
373,927 | 930,185 | null | null | null | null | ord_dataset-d8a5dc784dde4465894ec7c69d2e3ba6 | 2010-01-01T00:01:00 | true | To a stirred and cooled suspension of N-tert-butyl-3-[6-methyl-4-(4-trifluoromethylphenyl)-[2,4′]bipyridinyl-2′-yl]-benzenesulfonamide (example 287) (0.239 g, 0.455 mmol) in dichloromethane (1.5 mL) was added TFA (10 mL) and the reaction mixture was allowed to stir at room temperature for 16 h. The mixture was evaporat... | Cc1cc(-c2ccc(C(F)(F)F)cc2)cc(-c2ccnc(-c3cccc(S(N)(=O)=O)c3)c2)n1 | null | Cc1cc(-c2ccc(C(F)(F)F)cc2)cc(-c2ccnc(-c3cccc(S(=O)(=O)NC(C)(C)C)c3)c2)n1 | null | null | C([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[CH:20]=[C:19]([C:21]3[CH:26]=[C:25]([C:27]4[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=4)[CH:24]=[C:23]([CH3:37])[N:22]=3)[CH:18]=[CH:17][N:16]=2)[CH:10]=1)(=[O:8])=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[CH3:37][C:23]1[N:22]=[C:21]([C:19]2[... | null | ClCCl | O=C(O)C(F)(F)F | null | null | 93.6 | null |
779,260 | 1,377,807 | Cl | [BH4-] | [Na+] | null | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | 2013-01-01T00:12:00 | true | Sodium borohydride (63.58 mg; 1.68 mmol; 0.07 eq) is suspended in DME (6.5 mL) at room temperature. Borane-methyl sulfide complex (39.61 mL; 2 M; 79.22 mmol; 3.3 eq) is added dropwise. After 30 min stirring at room temperature, a solution of 4-(4-methoxy-2-nitrobenzylidene)tetrahydro-2H-thiopyran (6.37 g; 24.01 mmol; 1... | COc1ccc(CC2CCSCC2)c(N)c1 | null | COc1ccc(C=C2CCSCC2)c([N+](=O)[O-])c1 | null | null | [BH4-].[Na+].[CH3:3][O:4][C:5]1[CH:17]=[CH:16][C:8]([CH:9]=[C:10]2[CH2:15][CH2:14][S:13][CH2:12][CH2:11]2)=[C:7]([N+:18]([O-])=O)[CH:6]=1.Cl>COCCOC.CO>[CH3:3][O:4][C:5]1[CH:17]=[CH:16][C:8]([CH2:9][CH:10]2[CH2:15][CH2:14][S:13][CH2:12][CH2:11]2)=[C:7]([CH:6]=1)[NH2:18] | 0.5 | CO | COCCOC | null | 25 | null | 41.9 |
637,305 | 1,132,803 | [Cu]Br | O=N[O-] | [Na+] | null | ord_dataset-aaeaab5f3720492494c1cbbdd0ed2820 | 2012-01-01T00:02:00 | true | A mixture of ethyl 5-amino-2-methylbenzoate (1.50 g, 8.3 mmol) in 48% HBr (12 mL) and water (24 mL) was cooled with an ice-bath for 15 min. Sodium nitrite (0.59 g, 8.6 mmol) was then added dropwise as a solution in water (2 mL), and the resulting mixture stirred for 5 min. After this time, the mixture was added to an i... | CCOC(=O)c1cc(Br)ccc1C | null | CCOC(=O)c1cc(N)ccc1C | Br | null | N[C:2]1[CH:3]=[CH:4][C:5]([CH3:13])=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].N([O-])=O.[Na+].[BrH:18]>O.C(OCC)C.[Cu]Br>[Br:18][C:2]1[CH:3]=[CH:4][C:5]([CH3:13])=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8] | 0.08 | CCOCC | O | null | 70 | 69 | null |
15,380 | 590,662 | Cl | null | null | null | ord_dataset-7a74d48eeefd45aba53e7258f3ae067a | 2003-01-01T00:04:00 | true | Dissolve 2-phenylpropionic acid (30 g) in 2B ethanol (100 mL and add anhydrous HCl (10 g). Allow to sit for 48-72 hours, evaporate the solvent in vacuo and purify by distillation to give ethyl 2-phenylpropionate (31 g); bp 100 C at 6 mm. | CCOC(=O)C(C)c1ccccc1 | null | CC(C(=O)O)c1ccccc1 | CCO | null | [C:1]1([CH:7]([CH3:11])[C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH2:13](O)[CH3:14]>>[C:1]1([CH:7]([CH3:11])[C:8]([O:10][CH2:13][CH3:14])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1 | 60 | null | null | null | null | null | null |
446,250 | 1,025,106 | O=C([O-])[O-] | [K+] | null | null | ord_dataset-136cfada6ce247b4919085a57363459e | 2011-01-01T00:01:00 | true | A mixture of 2,4-difluoro-1-nitrobenzene (50 g, 314 mmol), 4-methyl-1H-imidazole (25.7 g, 314 mmol) and potassium carbonate (100 g, 725 mmol) in dichloromethane (600 mL) was stirred at room temperature for 4 days. The mixture was washed with water then dried over magnesium sulfate. Solvent was removed under reduced pre... | Cc1cn(-c2cc(F)ccc2[N+](=O)[O-])cn1 | null | Cc1c[nH]cn1 | O=[N+]([O-])c1ccc(F)cc1F | null | F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH3:12][C:13]1[N:14]=[CH:15][NH:16][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[F:8][C:6]1[CH:5]=[CH:4][C:3]([N+:9]([O-:11])=[O:10])=[C:2]([N:16]2[CH:17]=[C:13]([CH3:12])[N:14]=[CH:15]2)[CH:7]=1 | 96 | ClCCl | null | null | 25 | null | 50.4 |
256,324 | 431,994 | null | null | null | null | ord_dataset-8cbb58558c904b2b85fa7a1b084a0de9 | 1999-01-01T00:06:00 | true | 2-Amino-4-chloro-6-hydroxy-5-nitropyrimidine (4 g), 3-methylbutylamine (1.8 g) and triethylamine (6 ml) were heated at reflux for 5 h then left stirring overnight at room temperature in ethanol. The precipitate was filtered and washed with water and air dried to yield the title compound as a yellow solid. | CC(C)CCNc1nc(N)nc(O)c1[N+](=O)[O-] | null | CC(C)CCN | Nc1nc(O)c([N+](=O)[O-])c(Cl)n1 | null | [NH2:1][C:2]1[N:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[C:4]([OH:12])[N:3]=1.[CH3:13][CH:14]([CH3:18])[CH2:15][CH2:16][NH2:17].C(N(CC)CC)C>C(O)C>[NH2:1][C:2]1[N:7]=[C:6]([NH:17][CH2:16][CH2:15][CH:14]([CH3:18])[CH3:13])[C:5]([N+:9]([O-:11])=[O:10])=[C:4]([OH:12])[N:3]=1 | null | CCO | CCN(CC)CC | null | null | null | null |
516,145 | 683,395 | null | null | null | null | ord_dataset-359b8fc87f4244be89d6f02bc5036eac | 2005-01-01T00:09:00 | true | A mixture of the title compound of Example 89 (30 mg, 0.06 mmol) and N,N-dimethylmethyleneiminium iodide (57 mg, 0.23 mmol) in anhydrous dichloromethane was stirred at room temperature overnight. The reaction mixture was purified by solid phase extraction using a Varian Bond Elut SCX cartridge (methanol for washing, me... | CCCOc1ccc(S(=O)(=O)N2CCN(C)CC2)cc1-c1[nH]c2c(c1CN(C)C)c(=O)n(C)c(=O)n2CCC | null | CCCOc1ccc(S(=O)(=O)N2CCN(C)CC2)cc1-c1cc2c(=O)n(C)c(=O)n(CCC)c2[nH]1 | null | null | [CH3:1][N:2]1[C:7](=[O:8])[C:6]2[CH:9]=[C:10]([C:12]3[CH:17]=[C:16]([S:18]([N:21]4[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]4)(=[O:20])=[O:19])[CH:15]=[CH:14][C:13]=3[O:28][CH2:29][CH2:30][CH3:31])[NH:11][C:5]=2[N:4]([CH2:32][CH2:33][CH3:34])[C:3]1=[O:35]>ClCCl>[CH3:1][N:2]([CH2:7][C:9]1[C:6]2[C:7](=[O:8])[N:2]([... | 8 | ClCCl | null | null | 25 | null | 190.2 |
140,088 | 1,591,795 | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [Na+] | null | ord_dataset-e8c6a25568b64529b960953990e6921f | 2015-01-01T00:06:00 | true | A mixture of 6.5 g (14 mmol) of 2-(4-(10-bromoanthracen-9-yl)naphthalene-1-yl)thiophene, 7.53 g (16 mmol) of 2-(10,10-dimethyl-10H-indeno[1,2-b]triphenylen-12-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 0.16 g (0.14 mmol) of tetrakis(triphenylphosphine)palladium, 11 ml of 2M Na2CO3, 30 ml of EtOH and 65 ml toluene was... | CC1(C)C=C(c2c3ccccc3c(-c3ccc(-c4cccs4)c4ccccc34)c3ccccc23)C=C2C=c3cc4c5ccccc5c5ccccc5c4cc3=C21 | null | CC1(C)C=C(B2OC(C)(C)C(C)(C)O2)C=C2C=c3cc4c5ccccc5c5ccccc5c4cc3=C21 | Brc1c2ccccc2c(-c2ccc(-c3cccs3)c3ccccc23)c2ccccc12 | null | Br[C:2]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]([C:26]3[S:27][CH:28]=[CH:29][CH:30]=3)=[CH:18][CH:17]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[CH:7]2.[CH3:31][C:32]1([CH3:66])[C:56]2[C:36]([CH:37]=[C:38]3[CH:55]=[C:54]4[C:41]([C:42]5[C:47]([C:48]6[C:... | null | CO | Cc1ccccc1 | CCO | 90 | null | 62.7 |
364,106 | 1,735,814 | [Al+3] | [Cl-] | null | null | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | 2016-01-01T00:06:00 | true | To 11-(2-ethylhexyl)-11H-benzo[a]carbazole (10.0 g, 30.6 mmol) in CH2Cl2 (150 mL) are added 4-fluorobenzoyl chloride (5.03 g, 31.7 mmol) and AlCl3 (4.58 g, 34.3 mmol) at 0° C. After stirring for 0.5 hour, the reaction mixture is stirred for 2 hours at room temperature. The reaction mixture is poured into ice-water, and... | CCCCC(CC)Cn1c2ccccc2c2cc(C(=O)c3ccc(F)cc3)c3ccccc3c21 | null | CCCCC(CC)Cn1c2ccccc2c2ccc3ccccc3c21 | O=C(Cl)c1ccc(F)cc1 | null | [CH2:1]([CH:3]([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:4][N:5]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]3=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH3:2].[F:26][C:27]1[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][CH:28]=1.[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[CH2:1]([CH:3]([CH2:22][CH2... | 0.5 | ClCCl | null | null | 0 | null | null |
522,456 | 1,281,159 | null | null | null | null | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | 2013-01-01T00:04:00 | true | Using the same method as in Example 19-(ii), 3-thiopheneboronic acid was reacted with the 2-[((2-[(3-bromobenzyl)amino]-2-oxoethoxy)acetyl)amino]-5-chlorobenzoic acid methyl ester to give 5-chloro-2-([(2-oxo-2-([3-(thiophene-3-yl)benzyl]amino)ethoxy)acetyl]amino)benzoic acid.methyl ester (yield: 77%). | O=C(COCC(=O)Nc1ccc(Cl)cc1C(=O)O)NCc1cccc(-c2ccsc2)c1 | null | OB(O)c1ccsc1 | COC(=O)c1cc(Cl)ccc1NC(=O)COCC(=O)NCc1cccc(Br)c1 | null | [S:1]1[CH:5]=[CH:4][C:3](B(O)O)=[CH:2]1.C[O:10][C:11](=[O:36])[C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[NH:19][C:20](=[O:35])[CH2:21][O:22][CH2:23][C:24]([NH:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30](Br)[CH:29]=1)=[O:25]>>[Cl:18][C:16]1[CH:15]=[CH:14][C:13]([NH:19][C:20](=[O:35])[CH2:21][O:22][CH2:23]... | null | null | null | null | null | null | null |
796,545 | 1,597,439 | null | null | null | null | ord_dataset-e8c6a25568b64529b960953990e6921f | 2015-01-01T00:06:00 | true | To a mixture of 1-(3-fluorophenyl)-N-methoxy-N-methyl-1H-indole-2-carboxamide (0.52 g, 1.7 mmol) in tetrahydrofuran (10 mL) was added 3.0 M methylmagnesium bromide in ether (4.6 mL, 0.014 mol). The reaction was stirred at room temperature overnight. The reaction was quenched with saturated NH4Cl solution and extracted ... | CC(=O)c1cc2ccccc2n1-c1cccc(F)c1 | null | CON(C)C(=O)c1cc2ccccc2n1-c1cccc(F)c1 | C[Mg]Br | null | [F:1][C:2]1[CH:3]=[C:4]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[C:9]2[C:17](N(OC)C)=[O:18])[CH:5]=[CH:6][CH:7]=1.[CH3:23][Mg]Br.CCOCC>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[C:9]2[C:17](=[O:18])[CH3:23])[CH:5]=[CH:6][CH:7]=1 | 8 | C1CCOC1 | CCOCC | null | 25 | 91 | null |
1,022 | 1,198,953 | CC(C)(C)[O-] | [K+] | null | null | ord_dataset-fb72428f30234761b4216139dc228d0c | 2012-01-01T00:09:00 | true | A solution of 5-fluoro-1H-indole (16.9 mmol) and potassium tert-butoxide (33.8 mmol) in DMF (76 mL) is stirred at rt under N2 for 2 h. 0.15 M NH2Cl. in ether (169.2 mL) is added drop-wise for 15 minutes at rt. The reaction mixture is stirred at rt for 2 h, then quenched with 10% Na2S2O3 aqueous solution and extracted w... | Nn1ccc2cc(F)ccc21 | null | Fc1ccc2[nH]ccc2c1 | NCl | null | [F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.CC(C)([O-])C.[K+].[NH2:17]Cl>CN(C=O)C.CCOCC>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([NH2:17])[CH:6]=[CH:5]2 | 2 | CN(C)C=O | CCOCC | null | 25 | null | 30 |
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