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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
727,241 | ord_dataset-eb4226b4f7644a01a737e7547b70014a | null | 2006-01-01T00:09:00 | true | [C:1]1([CH:7]2[S:12][CH2:11][CH2:10][CH2:9][S:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.[C:18]([O:22][C:23](=[O:32])[NH:24][CH:25]([CH:30]=[O:31])[CH2:26][CH2:27][CH2:28][CH3:29])([CH3:21])([CH3:20])[CH3:19].C(O)(=O)C>C1COCC1>[C:18]([O:22][C:23](=[O:32])[NH:24][CH:25]([CH:30]([OH:31])[C:7]1([C:1]2[CH:2]=[CH:3][... | c1ccc(C2SCCCS2)cc1 | CCCCC(C=O)NC(=O)OC(C)(C)C | null | [Li]CCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | C1CCOC1 | null | null | null | null | null | null | null | null | null | -60 | 0.5 | 2-Phenyl-1,3-dithiane (Aldrich) (3.79 g; 19.3 mmol) was mixed with dry distilled THF (20 mL) under a nitrogen atmosphere. The solution was cooled to −60° C. and n-butyl lithium (1.6M in pentane, 1.56 mmol, 9.74 mL) was added slowly by syringe. The reaction mixture was warmed to −20° C. and held at that temperature for ... | CCCCC(NC(=O)OC(C)(C)C)C(O)C1(c2ccccc2)SCCCS1 | null | 56 | null |
51,321 | ord_dataset-8881493772e04c4b9495fc2114379967 | null | 1979-01-01T00:02:00 | true | Cl[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][N:3]=1.C(N)[CH2:22][NH2:23]>CN(C)P(N(C)C)(N(C)C)=O>[C:22]([C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[... | Clc1ccc(C(c2ccccc2)c2ccccc2)cn1 | NCCN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)P(=O)(N(C)C)N(C)C | null | null | null | null | null | null | null | null | null | null | null | null | Heat a mixture of 16.5 g. (0.059 mole) of 2-chloro-5-(diphenylmethyl)-pyridine and 10.6 g. (0.059 mole) of cuprous cyanide in 120 ml. of hexamethylphosphoramide with stirring at 210°-220° C. for 7 hours. Pour the cooled reaction mixture into a solution of 200 ml. of ethylenediamine in 500 ml. of water, and extract with... | N#Cc1ccc(C(c2ccccc2)c2ccccc2)cn1 | null | null | null |
107,099 | ord_dataset-64bb36b111c249e0afcce8c5ad9cdbd0 | null | 1983-01-01T00:07:00 | true | [CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][C:12]#[N:13])=[CH:5][CH:4]=1.B#B>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH2:12][NH2:13])=[CH:5][CH:4]=1 | COc1ccc(CCCC#N)cc1 | null | null | B#B | 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 | Reduction of the butyronitrile by reaction with diborane gave 4-(4-methoxyphenyl)butylamine. | COc1ccc(CCCCN)cc1 | null | null | null |
435,570 | ord_dataset-386da077ab2340638cada986e2ef0770 | null | 1999-01-01T00:07:00 | true | [CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]=[O:11])[C:5]=1[NH:12][S:13]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)(=[O:15])=[O:14].Br[CH2:26][C:27]1[CH:31]=[CH:30][S:29][CH:28]=1>>[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]=[O:11])[C:5]=1[N:12]([S:13]([C:1... | COC(=O)c1cccc(C=O)c1NS(=O)(=O)c1ccc(OC)cc1 | BrCc1ccsc1 | 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 | Following the procedure of Example 322, 1.0 g (2.865 mmol) of the product of Example 321 is reacted with 3-bromomethyl thiophene to give 1.10 g (86%) of the product as a white solid after chromatography on silica gel eluting with EtOAc/Hexanes (1:3). Electrospray Mass Spec: 446.1 (M+H)+. | COC(=O)c1cccc(C=O)c1N(Cc1ccsc1)S(=O)(=O)c1ccc(OC)cc1 | null | 86 | null |
373,721 | ord_dataset-ee5599340390470d8e5b5ac1feddf9d6 | null | 1997-01-01T00:08:00 | true | Br[C:2]1[C:3](=[O:16])[C:4]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:5]=2[NH:6][C:7](=[O:10])[C:8]=1[OH:9].[C:17]1([Sn](C)(C)C)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1COCC1>[Cl:15][C:12]1[CH:13]=[CH:14][C:4]2[C:3](=[O:16])[C:2]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:8]([OH:9])[C:7](=[O:10])[NH:6][C:5]=2[C... | O=c1[nH]c2cc(Cl)ccc2c(=O)c(Br)c1O | C[Sn](C)(C)c1ccccc1 | 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 | 25 | null | To a solution of 4-Bromo-8-chloro-3-hydroxy-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine (400 mg) in THF (10 mL) was added phenyltrimethylstannane (600 mg) and trans-Benzyl(chloro)bis (triphenyl-phosphinepalladium(II) (50 mg). The solution was heated to reflux for 5 hours at which time a dark gray precipitate formed. The re... | O=c1[nH]c2cc(Cl)ccc2c(=O)c(-c2ccccc2)c1O | null | 58 | null |
407,065 | ord_dataset-d5bb2294ac964841b8ffc9e0a34e93af | null | 1998-01-01T00:07:00 | true | C1(O[C:8](=[O:21])[NH:9][C:10]2[C:11]([O:19][CH3:20])=[N:12][C:13]([CH3:18])=[C:14]([CH2:16][CH3:17])[CH:15]=2)C=CC=CC=1.[C:22]1([N:36]2[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]2)[C:35]2[C:26](=[CH:27][C:28]3[C:33]([CH:34]=2)=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:25]=[CH:24][CH:23]=1>>[CH2:16]([C:14]1[CH:15]=[C:10]([NH:9][... | c1ccc2cc3c(N4CCNCC4)cccc3cc2c1 | CCc1cc(NC(=O)Oc2ccccc2)c(OC)nc1C | 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 | Phenyl-N-(5-ethyl-2-methoxy-6-methylpyridin-3-yl)carbamate and 1-(1-anthryl)piperazine were reacted by the same way with the example 1 to obtain the titled compound. | CCc1cc(NC(=O)N2CCN(c3cccc4cc5ccccc5cc34)CC2)c(OC)nc1C | null | 57 | null |
735,059 | ord_dataset-76dd1b78ee414d2da0ed30700ef026f7 | null | 2006-01-01T00:10:00 | true | [CH2:1]([O:3][C:4]([C:6]1[C:10]([C:11]#[CH:12])=[CH:9][S:8][C:7]=1[NH2:13])=[O:5])[CH3:2].I[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(NC(C)C)(C)C>CC#N.[Cu](I)I.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>[CH2:1]([O:3][C:4]([C:6]1[C:10]([C:11]#[C:12][C:15]2[CH:20]=[... | Ic1ccccc1 | C#Cc1csc(N)c1C(=O)OCC | null | Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1 | I[Cu]I | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)NC(C)C | CC#N | null | null | null | null | null | null | null | null | null | 25 | 0.5 | 2-Amino-4-ethynyl-thiophene-3-carboxylic acid ethyl ester (0.075 g, 0.385 mmol) was dissolved in anhydrous CH3CN (2.0 mL). This was treated with iodobenzene (0.129 mL, 1.15 mmol) followed by diisopropylamine (0.272 mL, 1.92 mmol). The solution was then degassed and treated with copper iodide (0.0018 g, 0.010 mmol) and ... | CCOC(=O)c1c(C#Cc2ccccc2)csc1N | null | 77.5 | null |
771,186 | ord_dataset-8214eb8444a44dc2900ccb42dbeff15e | null | 2007-01-01T00:05:00 | true | [N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C@@H:7]([O:26][Si](CC)(CC)CC)[CH2:8][NH:9][C@H:10]([CH3:25])[CH2:11][C:12]2[C:20]3[C:15](=[C:16]([C:21]([O:23][CH3:24])=[O:22])[CH:17]=[CH:18][CH:19]=3)[NH:14][CH:13]=2)[CH:2]=1>FC(F)(F)C(O)=O>[OH:26][C@H:7]([C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[CH2:8][NH:9][C@H:10]([CH3:25])[CH2:11]... | CC[Si](CC)(CC)O[C@@H](CN[C@H](C)Cc1c[nH]c2c(C(=O)OC)cccc12)c1cccnc1 | 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 | 25 | 24 | methyl 3-[(2R)-2-(2-pyridin-3-yl-(2R)-2-(triethylsilyloxy)ethyl-amino)propyl]-1H-indole-7-carboxylate (0.72 g, 1.54 mmol) is dissolved in trifluoroacetic acid (20 mL), and the mixture is stirred at room temperature for one day. After concentrated, to the residue is added ethyl acetate, and the mixture is washed with a ... | COC(=O)c1cccc2c(C[C@@H](C)NC[C@H](O)c3cccnc3)c[nH]c12 | null | 80.8 | null |
129,746 | ord_dataset-2f37329a4b254471a74f2eb0981f11ec | null | 1985-01-01T00:05:00 | true | [CH:1]([C:3]1[CH:13]=[C:12]([CH3:14])[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:5]([CH3:15])[C:4]=1[NH:16][C:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=O.[NH3:25]>>[C:18]1([C:17]2[N:25]=[CH:1][C:3]3[C:4](=[C:5]([CH3:15])[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:12]([CH3:14])[CH:13]=3)[N:16]=2)[CH:23]=[... | N | CCOC(=O)c1c(C)cc(C=O)c(NC(=O)c2ccccc2)c1C | 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 | Ethyl 4-formyl-2,6-dimethyl-3-benzoylaminobenzoate was used instead of the compound of formula (II) used in Example 1 and reacted with ammonia in the same way as in Example 1. The reaction product was chromatographed on a silica gel column in the same way as in Example 1. The solvent was evaporated, and the residue was... | CCOC(=O)c1c(C)cc2cnc(-c3ccccc3)nc2c1C | null | null | null |
83,541 | ord_dataset-7bed824f566d4af0b51d74d386b14bd6 | null | 1981-01-01T00:07:00 | true | [CH2:1]([S:3][C:4]1[S:8][C:7]([C:9]([NH2:11])=[O:10])=[N:6][N:5]=1)[CH3:2].[OH:12]O>C(O)(=O)C>[CH2:1]([S:3]([C:4]1[S:8][C:7]([C:9]([NH2:11])=[O:10])=[N:6][N:5]=1)=[O:12])[CH3:2] | OO | CCSc1nnc(C(N)=O)s1 | 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 | null | 3 | 38 g of 5-ethylthio-1,3,4-thiadiazole-2-carboxamide are dissolved at 40° C. in 400 ml of glacial acetic acid and are then slowly reacted with 22.6 ml of a 30% hydrogen peroxide upon stirring. The solution is kept for another 3 hours at the same temperature. At the end of this period the oxidation is sufficiently comple... | CCS(=O)c1nnc(C(N)=O)s1 | null | null | null |
318,269 | ord_dataset-eb32c2b9cbdf4fc39ce6c9fe0fa11430 | null | 1995-01-01T00:10:00 | true | C(O[C:4](=[O:29])[C:5](=[O:28])[N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([CH:20]=[C:21]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[CH:13]=2)[CH2:8][CH2:7]1)C.[NH2:30][OH:31].Cl.[OH-].[K+].CO>CO>[C:21]1(=[CH:20][C:14]2[CH:13]=[C:12]([CH:9]3[CH2:10][CH2:11][N:6]([C:5](=[O:28... | NO | CCOC(=O)C(=O)N1CCC(c2ccc(OC)c(C=C3CCCCCC3)c2)CC1 | null | Cl | [K+] | [OH-] | 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 | 8 | To a stirred solution of 2-[4-(3-cycloheptylidenemethyl-4-methoxy-phenyl)-piperidin-1-yl]-oxo-acetic acid ethyl ester (0.6 mmol, 0.250 g) in methanol (5 mL) was added hydroxylamine.HCl (2.4 mmol, 0.167 g, followed by KOH/MeOH solution (5M, 600 μL) dropwise at room temperature. A white solid precipitated out of solution... | COc1ccc(C2CCN(C(=O)C(=O)NO)CC2)cc1C=C1CCCCCC1 | null | null | null |
1,520,868 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | [CH:1]([N:4]([CH3:22])[C:5]1[C:6](=[O:21])[NH:7][C:8]2[C:13]([N:14]=1)=[CH:12][C:11]([C:15]([O:17][CH3:18])=[O:16])=[C:10]([O:19][CH3:20])[CH:9]=2)([CH3:3])[CH3:2].N1C=CC=CC=1.[O:29](S(C(F)(F)F)(=O)=O)[S:30]([C:33]([F:36])([F:35])[F:34])(=O)=[O:31]>ClCCl>[CH:1]([N:4]([CH3:22])[C:5]1[C:6]([O:21][S:30]([C:33]([F:36])([F:... | COC(=O)c1cc2nc(N(C)C(C)C)c(=O)[nH]c2cc1OC | O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 8 | To a solution of methyl 3-(isopropyl(methyl)amino)-7-methoxy-2-oxo-1,2-dihydroquinoxaline-6-carboxylate (2.0 g, 6.55 mmol) in dichloromethane (80 mL) was added Pyridine (2.0 g, 25.28 mmol) and Tf2O (3.66 g, 12.97 mmol) with stirring overnight under an atmosphere of nitrogen at room temperature. The reaction mixture was... | COC(=O)c1cc2nc(N(C)C(C)C)c(OS(=O)(=O)C(F)(F)F)nc2cc1OC | null | null | null |
1,421,637 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | [NH:1]([C:3]1[CH:12]=[C:11]([CH3:13])[C:10]2[C:5](=[C:6]([CH3:15])[CH:7]=[CH:8][C:9]=2[CH3:14])[N:4]=1)[NH2:2].[Cl:16][C:17]1[CH:18]=[C:19]([N:24]=[C:25]=[O:26])[CH:20]=[C:21]([Cl:23])[CH:22]=1>>[Cl:16][C:17]1[CH:18]=[C:19]([NH:24][C:25]([NH:2][NH:1][C:3]2[CH:12]=[C:11]([CH3:13])[C:10]3[C:5](=[C:6]([CH3:15])[CH:7]=[CH:... | Cc1ccc(C)c2c(C)cc(NN)nc12 | O=C=Nc1cc(Cl)cc(Cl)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 | A solution of 2-hydrazinyl-4,5,8-trimethylquinoline (100 mg, 0.50 mmol) and 93.53 mg (1.0 eq) of 3,5-dichlorophenyl isocyanate was reacted as outlined in Scheme 1 above to give the desired title compound. Spectroscopic data: 1H NMR (300 MHz, DMSO-d6) δ ppm 2.43 (s, 3 H) 2.73 (s, 3 H) 2.77 (s, 3 H) 6.69 (s, 1 H) 6.92 (d... | Cc1ccc(C)c2c(C)cc(NNC(=O)Nc3cc(Cl)cc(Cl)c3)nc12 | null | null | null |
292,503 | ord_dataset-6c3ec086c8c9475e8d31a44641b49e02 | null | 1994-01-01T00:06:00 | true | [NH2:1][CH:2]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=2[N:4]([CH2:19][CH2:20][OH:21])[C:3]1=[O:22].[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[C:24]1[C:32](Cl)=[O:33].C(N(CC)CC)C>C(Cl)Cl>[OH:21][CH2:20][CH2:19][N:4]1[C:5]2[CH:18]=[CH:17][CH... | O=C(Cl)c1cc2ccccc2[nH]1 | NC1N=C(c2ccccc2)c2ccccc2N(CCO)C1=O | null | null | null | 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 | 0.17 | 3-(RS)-Amino-1,3-dihydro-1-(2-hydroxyethyl)-5-phenyl-2H-1,4-benzodiazepin-2-one (69.0 mg, 0.234 mmole), indole-2-carbonyl chloride (43.1 mg, 0.240 mmole) and triethylamine (33.3 μl, 0.240 mmole) were combined in CH2Cl2 (3 ml). The reaction was stirred for 10 minutes at room temperature then chromatographed on silica ge... | O=C(NC1N=C(c2ccccc2)c2ccccc2N(CCO)C1=O)c1cc2ccccc2[nH]1 | null | null | null |
943,071 | ord_dataset-ed680843f6d14f5c9901869b2a06b4a4 | null | 2010-01-01T00:03:00 | true | [H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:5]=1[N:11]1[C:16]2[N:17]=[C:18](S(C)(=O)=O)[N:19]=[C:20]([C:21]3[CH:22]=[C:23]([NH:28][C:29](=[O:38])[C:30]4[CH:35]=[CH:34][C:33]([CH3:36])=[C:32]([F:37])[CH:31]=4)[CH:24]=[CH:25][C:26]=3[CH3:27])[C:15]=2[CH2:14][NH:13][C:12]1=[O:43].[CH2:44]([OH:46])[CH3:45]>CC... | Cc1ccc(C(=O)Nc2ccc(C)c(-c3nc(S(C)(=O)=O)nc4c3CNC(=O)N4c3c(F)cccc3F)c2)cc1F | CCO | null | [H-] | [Na+] | 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 | 70 | 0.17 | Dry ethanol (2 mL) was treated with NaH (0.0056 mg, 0.140 mmol, 60% in mineral oil) under argon and stirred for 10 min. The compound N-{3-[8-(2,6-difluorophenyl)-2-(methylsulfonyl)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methylphenyl}-3-fluoro-4-methylbenzamide (0.064 g, 0.110 mmol) was added in ethano... | CCOc1nc(-c2cc(NC(=O)c3ccc(C)c(F)c3)ccc2C)c2c(n1)N(c1c(F)cccc1F)C(=O)NC2 | null | null | null |
1,216,574 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][C:31]=1[F:32])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([O:26]C)[C:10](=[O:25])[N:11]3[CH2:21][CH2:20][C:19](=[O:22])[CH2:18][N:17]([CH3:23])[C:16](=[O:24])[C:12]3=2)[C:7]1=[O:28].Br>C(O)(=O)C.O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][C:31]=1[F:32])[CH2:5][N:6]1[C... | COc1c2c(c3n(c1=O)CCC(=O)CN(C)C3=O)CCN(Cc1ccc(F)c(Cl)c1)C2=O | null | null | Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | C1COCCO1 | null | null | null | null | null | null | null | null | null | 25 | 1.5 | A mixture of 11-(3-chloro-4-fluorobenzyl)-9-methoxy-2-methyl-5,6,12,13-tetrahydro-2H[1,4]diazocino[2,1-a]-2,6-naphthyridine-1,4,8,10(3H, 11H)-tetrone (25 mg, 0.05 mmol) and 33% hydrogen bromide in acetic acid (0.5 mL) in dioxane (1 mL) was stirred at room temperature for 1.5 hour. The product mixture was concentrated u... | CN1CC(=O)CCn2c(c3c(c(O)c2=O)C(=O)N(Cc2ccc(F)c(Cl)c2)CC3)C1=O | null | null | null |
742,198 | ord_dataset-437aa6654d5044ddaef3346dc4c6e08a | null | 2006-01-01T00:11:00 | true | [N+:1]([C:4]1[CH:5]=[C:6]([C:12]2[O:13][C:14]3[CH:20]=[CH:19][C:18](Br)=[CH:17][C:15]=3[N:16]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])([O-:3])=[O:2].[CH3:22][O:23][C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=1>>[N+:1]([C:4]1[CH:5]=[C:6]([C:12]2[O:13][C:14]3[CH:20]=[CH:19][C:18]([C:28]4[CH:27]=[CH:26][CH:25]=[C:24]([... | COc1cccc(B(O)O)c1 | COc1ccc(-c2nc3cc(Br)ccc3o2)cc1[N+](=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 | null | null | null | null | Prepared by the method of Example 15d), from 2-(3-nitro-4-methoxyphenyl)-5-bromobenzoxazole (200 mg, 0.57 mmol) and 3-methoxyphenylboronic acid (131 mg, 0.86 mmol) the subtitle compound was obtained, (98 mg, 45%). 1H NMR (DMSO) δ 8.71(d, 1H), 8.52(dd, 1H), 8.35(t, 1H), 8.17(d, 1H), 7.93(d, 1H), 7.82(dd, 1H), 7.69(d, 1H... | COc1cccc(-c2ccc3oc(-c4ccc(OC)c([N+](=O)[O-])c4)nc3c2)c1 | null | null | null |
1,739,370 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([O:15]C(=O)C)[C@H:8]([O:19][CH3:20])[O:7][C@H:6]1[C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([CH2:28][C:29]2[CH:38]=[CH:37][C:32]3[O:33][CH2:34][CH2:35][O:36][C:31]=3[CH:30]=2)[CH:22]=1)(=O)C.C[O-].[Na+]>CO>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([C@H:6]2[C@H:5]([OH:4])[C@@H:... | CO[C@@H]1O[C@@H](c2ccc(Cl)c(Cc3ccc4c(c3)OCCO4)c2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O | null | 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 | null | 1 | To a suspension of compound 143 (40 mg, 0.07 mmol) in CH3OH (5.0 mL) was added NaOMe (100 μL, 25% solution in CH3OH) at room temperature. After 1 h, the resulting mixture was concentrated in vacuo. The crude was purified by preparative HPLC (reverse phase) to provide the title compound (12 mg, 42%) as a white solid. | CO[C@@H]1O[C@@H](c2ccc(Cl)c(Cc3ccc4c(c3)OCCO4)c2)[C@H](O)[C@@H](O)[C@@H]1O | null | 40.5 | null |
882,091 | ord_dataset-3592bd645cd143ee8274cd0d834ae581 | null | 2009-01-01T00:05:00 | true | Cl.CN(C)CCCN=C=NCC.[Cl:13][C:14]1[CH:31]=[C:30]([F:32])[C:29]([N:33]2[C:38](=[O:39])[CH:37]=[C:36]([C:40]([F:43])([F:42])[F:41])[N:35]([CH3:44])[C:34]2=[O:45])=[CH:28][C:15]=1[O:16][C:17]1[C:18]([O:23][CH2:24][C:25]([OH:27])=[O:26])=[N:19][CH:20]=[CH:21][CH:22]=1.[C:46]([O:50][CH3:51])(=[O:49])[CH2:47]O.CN(C)C=O>O>[Cl:... | Cn1c(C(F)(F)F)cc(=O)n(-c2cc(Oc3cccnc3OCC(=O)O)c(Cl)cc2F)c1=O | COC(=O)CO | null | CCN=C=NCCCN(C)C | Cl | 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 | null | 1.5 | First, 0.13 g of 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride was added to a mixture of 0.30 g of [3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-2-pyridyloxy]acetic acid (compound a-2), 60 mg of methyl glycolate, and 2 ml of N,N-dimethylformami... | COC(=O)COC(=O)COc1ncccc1Oc1cc(-n2c(=O)cc(C(F)(F)F)n(C)c2=O)c(F)cc1Cl | null | 52.3 | null |
1,230,368 | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | null | 2012-01-01T00:11:00 | true | N1(C2C=CC=CN=2)CCC(N[C:8]([N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)=[O:9])CC1.Cl.Cl.[N:23]1([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=2)[CH2:28][CH2:27][CH:26]([NH:29][C:30]([N:32]2[CH2:37][CH2:36][CH:35]([NH2:38])[CH2:34][CH2:33]2)=[O:31])[CH2:25][CH2:24]1>>[N:23]1([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=2)[CH2:28]... | O=C(NC1CCN(c2ccccn2)CC1)n1ccnc1 | NC1CCN(C(=O)NC2CCN(c3ccccn3)CC2)CC1 | 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 | The title product is prepared analogously to imidazole-1-carboxylic acid (3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-amide (Intermediate A1) by replacing 3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-ylamine dihydrochloride with 4-amino-piperidine-1-carboxylic acid (3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-amide di... | O=C(NC1CCN(c2ccccn2)CC1)N1CCC(NC(=O)n2ccnc2)CC1 | null | null | null |
1,300,052 | ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c | null | 2013-01-01T00:05:00 | true | [C:1]1([CH2:11][C:12]([OH:14])=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[NH2:15][C:16]1[S:17][CH:18]=[C:19]([CH3:25])[C:20]=1[C:21]([O:23][CH3:24])=[O:22]>>[CH3:25][C:19]1[C:20]([C:21]([O:23][CH3:24])=[O:22])=[C:16]([NH:15][C:12](=[O:14])[CH2:11][C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[... | COC(=O)c1c(C)csc1N | O=C(O)Cc1cccc2ccccc12 | 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 from 2-(naphthalen-1-yl)acetic acid (10 g, 54 mmol) and methyl 2-amino-4-methylthiophene-3-carboxylate (9.2 g, 54 mmol) according to protocol A (15.4 g, 85%) as a white solid. 1H NMR (CDCl3) δ11.0 (s, 1H), 8.05-7.85 (m, 3H), 7.63-7.50 (m, 4H), 6.36 (s, 1H), 4.29 (s, 2H), 3.57 (s, 3H), 2.... | COC(=O)c1c(C)csc1NC(=O)Cc1cccc2ccccc12 | null | null | null |
1,057,133 | ord_dataset-373415d3e0e54004837cf4831e67666f | null | 2011-01-01T00:05:00 | true | [CH3:1][C:2]1[S:10][C:9]2[CH2:8][CH2:7][N:6]=[C:5]([CH3:11])[C:4]=2[C:3]=1[CH3:12].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[CH3:1][C:2]1[S:10][C:9]2[CH2:8][CH2:7][NH:6][CH:5]([CH3:11])[C:4]=2[C:3]=1[CH3:12] | CC1=NCCc2sc(C)c(C)c21 | null | 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 | null | null | null | null | null | null | null | null | null | null | null | null | null | In close analogy to the procedure described above, 2,3,4-Trimethyl-6,7-dihydrothieno[3,2-c]pyridine is reacted with sodium triacetoxyborohydride to provide the title compound. | Cc1sc2c(c1C)C(C)NCC2 | null | 14 | null |
835,816 | ord_dataset-ec576c604a9d47258c87c732a043ec71 | null | 2008-01-01T00:08:00 | true | [F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5](I)[CH:6]=[CH:7][CH:8]=1.[CH2:12]([N:19]1[CH2:24][CH2:23][C:22](=[O:25])[CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[CH2:12]([N:19]1[CH2:24][CH2:23][C:22]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:11])([F:10])[F:1])[CH:4]=2)([OH:25])[CH2:21][CH2:20]1)[C:1... | FC(F)(F)c1cccc(I)c1 | O=C1CCN(Cc2ccccc2)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 | Beginning with 3-trifluoromethyl-iodobenzene (3 g) and 1-benzyl-4-piperidone (2.1 g), 1.75 g of the title compound was recovered by the procedure described in preparation 1. MS m/z (rel. intensity, 70 eV) 335 (M+, 29), 244 (22), 146 (19), 91 (bp), 56 (19). | OC1(c2cccc(C(F)(F)F)c2)CCN(Cc2ccccc2)CC1 | null | 47.3 | null |
1,287,223 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [CH3:1][S:2]([C:5]1[CH:29]=[CH:28][C:8]([CH2:9][N:10]2[C:18]3[C:13](=[CH:14][C:15]([CH:19]=[C:20]4[S:24][C:23](SC)=[N:22][C:21]4=[O:27])=[CH:16][CH:17]=3)[CH:12]=[N:11]2)=[C:7]([C:30]([F:33])([F:32])[F:31])[CH:6]=1)(=[O:4])=[O:3].[CH3:34][NH:35][CH2:36][CH:37]([OH:40])[CH2:38][OH:39]>>[OH:40][CH:37]([CH2:38][OH:39])[CH... | CNCC(O)CO | CSC1=NC(=O)C(=Cc2ccc3c(cnn3Cc3ccc(S(C)(=O)=O)cc3C(F)(F)F)c2)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 | 2-[(2,3-Dihydroxy-propyl)-methyl-amino]-5-[1-(4-methanesulfonyl-2-trifluoromethyl-benzyl)-1H-indazol-5-ylmethylene]-thiazol-4-one was prepared from 5-[1-(4-methanesulfonyl-2-trifluoromethyl-benzyl)-1H-indazol-5-ylmethylene]-2-methylsulfanyl-thiazol-4-one and 3-Methylamino-propane-1,2-diol following General Procedure C. | CN(CC(O)CO)C1=NC(=O)C(=Cc2ccc3c(cnn3Cc3ccc(S(C)(=O)=O)cc3C(F)(F)F)c2)S1 | null | null | null |
1,707,821 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | Cl[CH2:2][C:3]1[N:4]=[C:5]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)[O:6][C:7]=1[CH3:8].[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([O-:28])=[O:27])=[CH:22][CH:21]=1.[Na+]>>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([CH2:2][C:3]2[N:4]=[C:5]([C:9]3[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3... | O=S([O-])c1ccc(Cl)cc1 | COC(=O)c1ccc(-c2nc(CCl)c(C)o2)cc1 | null | [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 | null | null | null | Reaction of chloride 2 (268 mg, 1.0 mmol) and sodium 4-chlorobenzenesulfinate (198 mg, 1.0 mmol) gave benzoate 19 (273 mg, 67%) as a white powder: mp (EtOAc) 186-188° C.; 1H NMR (CDCl3) δ 8.08 (ddd, J=8.7, 1.9, 1.6 Hz, 2H, H-2, H-6), 7.90 (ddd, J=8.7, 1.9, 1.6 Hz, 2H, H-3, H-5), 7.74 (ddd, J=8.7, 2.4, 2.0 Hz, 2H, H-2′,... | COC(=O)c1ccc(-c2nc(CS(=O)(=O)c3ccc(Cl)cc3)c(C)o2)cc1 | null | 67.3 | null |
123,015 | ord_dataset-a9b95e50436441ff8f3f12dd60d1e1b2 | null | 1984-01-01T00:10:00 | true | [CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[CH3:11].[Cl:12][C:13]1=[C:14]([Cl:20])[C:15]([O:17][C:18]1=[O:19])=[O:16]>C(Cl)CCl>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:15](=[O:16])[C:14]([Cl:20])=[C:13]([Cl:12])[C:18]([OH:19])=[O:17])=[C:3]1[CH3:11] | O=C1OC(=O)C(Cl)=C1Cl | Cc1cc2ccccc2n1C | 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 | null | A mixture of 10.0 g (0.07 mole) of 1,2-dimethylindole, 12.0 g (0.07 mole) of dichloromaleic anhydride and 200 ml of ethylene dichloride was stirred at ambient temperature for approximately eighteen hours. The solid present in the reaction mixture was collected by filtration. After drying at 60° C. in vacuo there was ob... | Cc1c(C(=O)C(Cl)=C(Cl)C(=O)O)c2ccccc2n1C | null | 91.5 | null |
357,036 | ord_dataset-58ec5adfcd8648dc9e26ee757d289517 | null | 1997-01-01T00:03:00 | true | [C:1]([C:4]1[C:5]([CH3:10])=[N:6][O:7][C:8]=1[CH3:9])(=[O:3])[CH3:2].Br[C:12]1[CH:16]=[CH:15][S:14][CH:13]=1>>[CH3:10][C:5]1[C:4]([C:1]([C:12]2[CH:16]=[CH:15][S:14][CH:13]=2)([OH:3])[CH3:2])=[C:8]([CH3:9])[O:7][N:6]=1 | CC(=O)c1c(C)noc1C | Brc1ccsc1 | 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 following the general method of Example 4 but starting with 4-acetyl-3,5-dimethylisoxazole and 3-bromothiophene. M.p. 93.5°-95° C. | Cc1noc(C)c1C(C)(O)c1ccsc1 | null | null | null |
952,592 | ord_dataset-3feb2a95f66e4706a4a50c977ccd9bf8 | null | 2010-01-01T00:04:00 | true | C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH3:11][O:12][CH2:13][CH:14]([OH:16])[CH3:15].[Br:17][C:18]1[CH:19]=[C:20]([CH:23]=[C:24](F)[CH:25]=1)[C:21]#[N:22].O>CN(C=O)C>[Br:17][C:18]1[CH:19]=[C:20]([CH:23]=[C:24]([O:16][CH:14]([CH3:15])[CH2:13][O:12][CH3:11])[CH:25]=1)[C:21]#[N:22] | COCC(C)O | N#Cc1cc(F)cc(Br)c1 | null | C[Si](C)(C)[N-][Si](C)(C)C | [Na+] | 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 | 25 | null | NaHMDS (148 mmol; 27.2 g) was charged to a 1000 ml round-bottomed flask (4 necks, thermometer, pressure-equalising dropping funnel, stopper, nitrogen inlet, magnetically stirred, oven dried, nitrogen purged), followed by DMF (300 ml). The mixture was stirred for 5 minutes then 1-methoxy-2-propanol (1.50 equiv; 148 mmol... | COCC(C)Oc1cc(Br)cc(C#N)c1 | null | 94.9 | null |
593,608 | ord_dataset-278fb6af8a994ac69e4d95e6e6eff756 | null | 2003-01-01T00:05:00 | true | [NH:1]1[CH2:6][CH2:5][S:4][CH2:3][C:2]1=[O:7].[F:8][C:9]([F:18])([F:17])[C:10]1[CH:15]=[CH:14][C:13](I)=[CH:12][CH:11]=1>[Cu]>[F:8][C:9]([F:18])([F:17])[C:10]1[CH:15]=[CH:14][C:13]([N:1]2[CH2:6][CH2:5][S:4][CH2:3][C:2]2=[O:7])=[CH:12][CH:11]=1 | O=C1CSCCN1 | FC(F)(F)c1ccc(I)cc1 | null | [Cu] | 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 | 192.5 | null | A mixture of thiomorpholin-3-one (500 mg, 4.27 mmol), 4-trifluoromethyl-1-iodobenzene (1.25 mL, 8.5 mmol) and copper metal (814 mg, 12.8 mmol) was heated in a sealed glass tube at 185-200° C. for 18 hours. The residue was then purified by flash chromatography to give 260 mg of the title product as a white solid. | O=C1CSCCN1c1ccc(C(F)(F)F)cc1 | null | 23.3 | null |
1,478,678 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:11]2[CH2:14][CH:13]([O:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[CH2:12]2)=[C:6]([CH:10]=1)[C:7](O)=[O:8].Cl.[NH2:24][C:25]1([C:28]2[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][CH:29]=2)[CH2:27][CH2:26]1>>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:11]2[CH2:12][CH:1... | O=C(O)c1cc(Cl)cnc1N1CC(Oc2ccc(F)cc2)C1 | COC(=O)c1ccc(C2(N)CC2)cc1 | 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 | The title compound (D150) (75 mg) was prepared according to the experimental procedure described in Description 146 starting from 5-chloro-2-(3-(4-fluorophenoxy)azetidin-1-yl)nicotinic acid (D102) (70 mg, 0.216 mmol) and solution methyl 4-(1-aminocyclopropyl)benzoate (D7) (49.18 mg, 0.216 mmol). | COC(=O)c1ccc(C2(NC(=O)c3cc(Cl)cnc3N3CC(Oc4ccc(F)cc4)C3)CC2)cc1 | null | 70 | null |
1,767,326 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | Cl[C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[NH2:11][CH2:12][C@H:13]1[C@@H:18]([O:19][CH3:20])[CH2:17][CH2:16][CH2:15][N:14]1[C:21]([C:23]1[N:24]=[C:25]([CH3:35])[S:26][C:27]=1[C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=1)=[O:22]>>[S:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[NH:11... | CO[C@H]1CCCN(C(=O)c2nc(C)sc2-c2ccc(F)cc2)[C@H]1CN | Clc1nc2ccccc2s1 | 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 following the same general protocol as described for Example 12 using 2-chlorobenzothiazole and rac-cis-(2-(aminomethyl)-3-methoxypiperidin-1-yl)(5-(4-fluorophenyl)-2-methylthiazol-4-yl)methanone. MS (ESI) 497.0 (M+H). | CO[C@H]1CCCN(C(=O)c2nc(C)sc2-c2ccc(F)cc2)[C@H]1CNc1nc2ccccc2s1 | null | null | null |
1,159,691 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | Cl.F[C:3](F)([O:15][NH2:16])[C:4]1[C:9]([F:10])=[C:8]([F:11])[C:7]([F:12])=[C:6]([F:13])[C:5]=1[F:14].[N:18]12[CH2:27][CH:22]3[CH2:23][CH:24]([CH2:26][CH:20]([C:21]3=O)[CH2:19]1)[CH2:25]2>C(O)C>[F:10][C:9]1[C:4]([CH2:3][O:15][N:16]=[C:21]2[CH:22]3[CH2:27][N:18]4[CH2:25][CH:24]([CH2:26][CH:20]2[CH2:19]4)[CH2:23]3)=[C:5]... | NOC(F)(F)c1c(F)c(F)c(F)c(F)c1F | O=C1C2CC3CC1CN(C3)C2 | null | Cl | 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 | 25 | null | Solid O-(perfluorobenzyl)hydroxylamine HCl (167 mg, 0.669 mmol, Aldrich Chemical Co.) was added to a warm solution of 1-azatricyclo[3.3.1.13,7]decan-4-one (102 mg, 0.675 mmol) (prepared as reported in: Becker, D. P. and Flynn, D. L. Synthesis 1992, 1080-1082) in ethanol (1 mL). The mixture was swirled with warming to d... | Fc1c(F)c(F)c(CON=C2C3CC4CC2CN(C4)C3)c(F)c1F | null | null | null |
654,355 | ord_dataset-fe016e2f90e741a590ad77fd5933161f | null | 2004-01-01T00:11:00 | true | [Si:1]([C:23]1(Br)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:16]1(Br)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:9]1(Br)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:2]1(Br)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:30]=[CH:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>>[C:3]1([CH:30]=[CH:31][C:32]2[CH:37]=[CH:36][CH:35... | C=Cc1ccccc1 | 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 | null | Use of tetrakis(4-bromophenyl)silane (Si(C6H4Br)4) gives access to structural analogs containing a silicon atom at the tetrahedral junction. Thus, reaction of Si(C6H4Br)4 with excess styrene gives tetrastilbenylsilane (Si(STB)4) in 52% yield using Pd(OAc)2 under phase transfer conditions. Similarly, (Si(C6H4Br)4) and 4... | C(=Cc1ccccc1[Si](c1ccccc1C=Cc1ccccc1)(c1ccccc1C=Cc1ccccc1)c1ccccc1C=Cc1ccccc1)c1ccccc1 | null | 52 | null |
473,380 | ord_dataset-cd531114850e4f239b2a3661044ae672 | null | 2000-01-01T00:08:00 | true | [CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH:12]2[C:17](=[O:18])[NH:16][C:15](=[O:19])[NH:14][C:13]2=[O:20])=[CH:5][CH:4]=1.[Br:21]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:21][C:12]1([CH2:11][CH2:10][CH2:9][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[C:13](=[O:... | COc1ccc(CCCC2C(=O)NC(=O)NC2=O)cc1 | O=C1CCC(=O)N1Br | null | O=C(OOC(=O)c1ccccc1)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 5-[3-(4-methoxyphenyl)propyl]barbituric acid (2.5 g), N-bromosuccinimide (2 g) and dibenzoyl peroxide (catalytic amount) in 110 ml of carbon tetrachloride is refluxed for about 1 hour then the solid which separated is filtered. The solid is redissolved in ethyl acetate and filtered through a silica gel cak... | COc1ccc(CCCC2(Br)C(=O)NC(=O)NC2=O)cc1 | null | 87.1 | null |
245,011 | ord_dataset-5eb2900a93c842ee98f26c305e657b61 | null | 1992-01-01T00:04:00 | true | [C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[C:11]([C:15]1[CH:16]=[C:17]([CH:21]=[C:22]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:23]=1[OH:24])[C:18](Cl)=[O:19])([CH3:14])([CH3:13])[CH3:12]>COCCOC>[C:1]([C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][C:18](=[O:19])[C:17]1[CH:21]=[C:22]([C:25]([CH3:... | Nc1ccccc1C(=O)O | CC(C)(C)c1cc(C(=O)Cl)cc(C(C)(C)C)c1O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COCCOC | null | null | null | null | null | null | null | null | null | null | 75 | 48 | A solution of 8.6g (0.063 mole) of anthranilic acid in 50 ml of 1,2-dimethoxyethane was added to a suspension of 8.0g (0.0298 mole) of 3,5-di-t-butyl-4-hydroxybenzoyl chloride in 150 ml of 1,2-dimethoxyethane. The reaction mixture was heated at approximately 75° C. for 30 minutes after which time it was stirred for 48 ... | CC(C)(C)c1cc(C(=O)Nc2ccccc2C(=O)O)cc(C(C)(C)C)c1O | null | 48.1 | null |
1,005,015 | ord_dataset-7448b89163bf426c9d9777809ce24cec | null | 2010-01-01T00:11:00 | true | [CH2:1]([O:3][C:4]([N:6]=[S:7]([C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]2[N:22]=[C:21]([NH:23][CH2:24][CH2:25][CH:26]([OH:28])[CH3:27])[C:20]([C:29]3[S:30][CH:31]=[CH:32][CH:33]=3)=[CH:19][N:18]=2)=[CH:12][CH:11]=1)([CH3:9])=[O:8])=[O:5])[CH3:2].C[N+]1([O-])CCOCC1>ClCCl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH2... | CCOC(=O)N=S(C)(=O)c1ccc(Nc2ncc(-c3cccs3)c(NCCC(C)O)n2)cc1 | null | null | O=[Ru](=O)(=O)[O-] | CCC[N+](CCC)(CCC)CCC | C[N+]1([O-])CCOCC1 | 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 | 0.25 | (RS)—N(ethoxycarbonyl)-(4-{[4-{(3-hydroxybutyl)amino}-5-(thiophen-2-yl)-pyrimidin-2-yl]amino}phenyl)-S-methylsulfoximide (169 mg, 0.35 mmol) is dissolved in dichloromethane (15 ml) and N-methylmorpholin-N-oxid (123 mg, 1.05 mmol) and molecular sieve (4 A, 496 mg) is added. The mixture is stirred for 15 min at RT. Then ... | CCOC(=O)N=S(C)(=O)c1ccc(Nc2ncc(-c3cccs3)c(NCCC(C)=O)n2)cc1 | null | null | null |
517,549 | ord_dataset-a495451286334c5c9bbcbd48a00c1350 | null | 2001-01-01T00:09:00 | true | [CH2:1]([O:3][C:4](=[O:10])[CH2:5][CH:6]1[CH2:9][NH:8][CH2:7]1)[CH3:2].C1COCC1.[C:16](Cl)([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]>C(=O)(O)[O-].[Na+]>[CH2:19]([O:18][C:16]([N:8]1[CH2:9][CH:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:10])[CH2:7]1)=[O:17])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:2... | CCOC(=O)CC1CNC1 | O=C(Cl)OCc1ccccc1 | null | O=C([O-])O | [Na+] | 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 | 2 | To a stirring mixture of azetidin-3-yl-acetic acid ethyl ester (1.0 g, 6.98 mmol), in saturated aqueous sodium bicarbonate (5 mL) and THF (5 mL) at 0° C. was added carbobenzyloxy chloride (1.1 mL, 7.68 mmol) dropwise. The ice bath was removed and the reaction mixture was stirred at room temperature for 2 hrs, then extr... | CCOC(=O)CC1CN(C(=O)OCc2ccccc2)C1 | null | 15.5 | null |
477,206 | ord_dataset-21c1b1c06c7e4e09a38b5b1c71a32e52 | null | 2000-01-01T00:10:00 | true | [C:1]([C:4]1[CH:15]=[CH:14][C:7]([CH:8]=[CH:9][C:10]([O:12][CH3:13])=[O:11])=[CH:6][C:5]=1[O:16][CH3:17])(O)=[O:2].Cl.CN.Cl.[CH2:22]([N:24]=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>CN(C)C=O.O>[CH3:17][O:16][C:5]1[CH:6]=[C:7]([CH:14]=[CH:15][C:4]=1[C:1](=[O:2])[NH:24][CH3:22])[CH:8]=[CH:9][C:10]([O:12][CH3:13])=[O:11] | COC(=O)C=Cc1ccc(C(=O)O)c(OC)c1 | CCN=C=NCCCN(C)C | null | CN | Cl | On1nnc2ccccc21 | 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 | 18 | To a solution of methyl 4-carboxy-3-methoxycinnamate (400 mg) in N,N-dimethylformamide were added methylamine hydrochloride (126 mg), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (390 mg) and 1-hydroxybenzotriazole (320 mg) at ambient temperature, and the mixture was stirred for 18 hours at the same tem... | CNC(=O)c1ccc(C=CC(=O)OC)cc1OC | null | 75.6 | null |
1,283,324 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][N:3]=1.[H-].[Na+].I[CH3:12].O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:12])=[CH:4][N:3]=1 | CI | Oc1ccc(Br)nc1 | null | [H-] | [Na+] | null | 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 | 72 | 2-Bromo-5-hydroxypyridine (5 mmol) is dissolved in DMF (10 ml) and NaH (1.4 eq., 60% suspension in liquid paraffin) is added. After 30 min iodomethane (2 eq.) is added and the reaction solution is stirred 3 days. The reaction solution is pored into water and extracted with methyl-tert.-butyl ether. The combined organic... | COc1ccc(Br)nc1 | null | 79 | null |
1,034,636 | ord_dataset-3af92aec23dc4810b92eb0d8c60023ee | null | 2011-01-01T00:03:00 | true | [CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5](=[O:15])[N:6]([CH3:14])[C:7](=[O:13])[NH:8]2.[H-].[Na+].Br[CH2:19][CH:20]([CH2:23][CH3:24])[CH2:21][CH3:22]>CN(C)C=O.O>[CH2:4]([CH:3]([CH2:12][CH3:11])[CH2:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5](=[O:15])[N:6]([CH3:14])[C:7](=[O:13])[N:8]2[CH2:1... | COc1cccc2[nH]c(=O)n(C)c(=O)c12 | CCC(CC)CBr | null | [H-] | [Na+] | 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 | 0.25 | To a solution of 5-methoxy-3-methylquinazoline-2,4(1H,3H)-dione (47 mg, 0.228 mmol) [example 5] in N,N-dimethylformamide (1 ml) was added sodium hydride (8.6 mg, 0.342 mmol). The mixture was stirred at 80° C. for 15 min and 1-bromo-2-ethylbutane (0.064 ml, 0.0753 mmol) was added. The resulting mixture was stirred at 80... | CCC(CC)COc1cccc2c1c(=O)n(C)c(=O)n2CC(CC)CC | null | 33.2 | null |
1,335,882 | ord_dataset-08852243bba44cb28769a5833f1515fe | null | 2013-01-01T00:09:00 | true | [CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([C:17]([O:19][CH3:20])=[O:18])=[CH:8][C:9](=[O:16])[N:10]2[CH2:13][CH:14]=O)=[CH:5][CH:4]=1.[O:21]1[C:26]2[CH:27]=[CH:28][C:29]([CH2:31][N:32]3[CH2:37][CH2:36][CH:35]([NH2:38])[CH2:34][CH2:33]3)=[CH:30][C:25]=2[O:24][CH2:23][CH2:22]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O... | NC1CCN(Cc2ccc3c(c2)OCCO3)CC1 | COC(=O)c1cc(=O)n(CC=O)c2cc(OC)ccc12 | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | 25 | 1 | To 10 mL of a chloroform solution containing 111 mg of methyl 7-methoxy-2-oxo-1-(2-oxoethyl)-1,2-dihydroquinoline-4-carboxylate and 93 mg of 1-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)piperidin-4-ylamine, 23 μL of acetic acid was added and stirred at room temperature for 1 hour. To the reaction mixture, 132 mg of sodium... | COC(=O)c1cc(=O)n(CCNC2CCN(Cc3ccc4c(c3)OCCO4)CC2)c2cc(OC)ccc12 | null | 70.5 | null |
951,162 | ord_dataset-3feb2a95f66e4706a4a50c977ccd9bf8 | null | 2010-01-01T00:04:00 | true | [F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=O)=[CH:4][CH:3]=1.[CH3:13][Mg]I>>[F:1][C:2]1[CH:11]=[C:10]2[C:5](=[CH:4][CH:3]=1)[CH2:6][CH2:7][CH:8]=[C:9]2[CH3:13] | O=C1CCCc2ccc(F)cc21 | C[Mg]I | 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 | Using general procedure A (Exp. 1.1), 7-fluoro-3,4-dihydro-2H-naphthalen-1-one (Lit. 16) was reacted with MeMgI to give 6-fluoro-4-methyl-1,2-dihydro-naphthalene as a colorless oil. | CC1=CCCc2ccc(F)cc21 | null | null | null |
93,640 | ord_dataset-f0d0fe3f599c471ca1c011dbbcdeeff2 | null | 1982-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:9]=[O:10])[CH:5]=[CH:6][CH:7]=1.[N+:17]([CH3:20])([O-:19])=[O:18]>>[N+:17]([CH2:20][CH:9]([OH:10])[CH:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)([O-:19])=[O:18] | O=CC(c1ccccc1)c1cccc(Cl)c1 | C[N+](=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 | null | null | null | null | the reaction of m-chlorophenyl-phenylacetaldehyde with nitromethane in the presence of a base to yield 3-nitro-1-phenyl-1-(m-chlorophenyl)propan-2-ol | O=[N+]([O-])CC(O)C(c1ccccc1)c1cccc(Cl)c1 | null | null | null |
1,760,131 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | [OH:1][C:2]1[N:7]2[N:8]=[C:9]([CH3:16])[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:6]2[CH:5]=[C:4]([CH3:17])[CH:3]=1.[F:18][C:19]1[C:26]([F:27])=[CH:25][CH:24]=[C:23]([F:28])[C:20]=1[CH2:21]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(/C(OC(C)C)=O)=N\C(OC(C)C)=O>C1COCC1.COC(C)(C)C>[CH3:16][C:9]1[C:10]([C:11]([O:13][... | CCOC(=O)c1c(C)nn2c(O)cc(C)cc12 | OCc1c(F)ccc(F)c1F | null | CC(C)OC(=O)/N=N/C(=O)OC(C)C | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COC(C)(C)C | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 1 | 1.2 g (5.25 mmol) of ethyl 7-hydroxy-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxylate from Example 8A were dissolved in 48 ml of THF. 1.7 g (10.50 mmol) of 2,3,6-trifluorobenzyl alcohol and 2.9 g (11.03 mmol) of triphenylphosphine were added. Subsequently, 2.2 ml (11.03 mmol) of diisopropyl (E)-diazene-1,2-dicarboxyla... | CCOC(=O)c1c(C)nn2c(OCc3c(F)ccc(F)c3F)cc(C)cc12 | null | 60.4 | null |
965,100 | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | null | 2010-01-01T00:06:00 | true | C([N:9]1[C:14](=[O:15])[C:13]([I:16])=[CH:12][N:11]([CH2:17][CH2:18][CH2:19][N:20]2[CH2:25][C@H:24]3[C@:22]([C:26]4[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=4)([CH2:23]3)[CH2:21]2)[C:10]1=[O:36])(=O)C1C=CC=CC=1>N.CO>[I:16][C:13]1[C:14](=[O:15])[NH:9][C:10](=[O:36])[N:11]([CH2:17][CH2:18][CH2:19... | O=C(c1ccccc1)n1c(=O)c(I)cn(CCCN2C[C@@H]3C[C@]3(c3ccc(C(F)(F)F)cc3)C2)c1=O | null | null | N | 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 | 3-Benzoyl-5-iodo-1-{3-[(1S,5R)-1-(4-trifluoromethyl-phenyl)-3-aza-bicyclo[3.1.0]hex-3-yl]-propyl}-1H-pyrimidine-2,4-dione (Prep 39, 840 mg, 1.38 mmol) was dissolved in 10% NH3 in MeOH solution (5 mL). The mixture was stirred at room temperature for 1 hour, the solvent was then evaporated under vacuum and the crude puri... | O=c1[nH]c(=O)n(CCCN2C[C@@H]3C[C@]3(c3ccc(C(F)(F)F)cc3)C2)cc1I | null | 73.9 | null |
297,097 | ord_dataset-ec7cb3d5a8704f64b01d401ea555974f | null | 1994-01-01T00:09:00 | true | [CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]2[NH:8][C:7]3[CH2:12][CH:13]([C:15]([OH:17])=[O:16])[CH2:14][C:6]=3[C:5]=2[CH:4]=1.Cl.[CH2:19](O)[CH3:20]>>[CH2:19]([O:16][C:15]([CH:13]1[CH2:12][C:7]2[NH:8][C:9]3[CH:10]=[CH:11][C:3]([O:2][CH3:1])=[CH:4][C:5]=3[C:6]=2[CH2:14]1)=[O:17])[CH3:20] | CCO | COc1ccc2[nH]c3c(c2c1)CC(C(=O)O)C3 | 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 | 25 | null | To a suspension of 1,2,3,4-tetrahydro-7-methoxycyclopent[b]indole-2-carboxylic acid (10 g, 0.043 mole) in 100 ml of absolute ethanol, was added 3 ml of ethereal HCl solution, and the mixture was stirred at ambient temperature for twenty hours. The mixture was concentrated to a brown oil (10 g), which was eluted on a si... | CCOC(=O)C1Cc2[nH]c3ccc(OC)cc3c2C1 | null | null | null |
632,354 | ord_dataset-de283386b8034acd99fba96d3c7d3227 | null | 2004-01-01T00:04:00 | true | Cl[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[N:3]=1.[F:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH2:19]>>[F:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH:19][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[N:3]=1 | Cc1cc(Cl)nc(-c2ccccn2)n1 | Nc1cccc(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 prepared from 4-chloro-6-methyl-2-(2-pyridinyl)pyrimidine (100 mg, 0.486 mmol) and 3-fluoroaniline (47 μl, 0.486 mmol) similar to Example 11 and isolated as a light brown solid (74 mg, 54%). 1H NMR (CDCl3): 8.83 (d, J=4.8 Hz, 1H), 8.47 (d, J=9 Hz, 1H), 7.88 (m, 1H), 7.44-7.30 (m, 4H), 7.18-7.14 (... | Cc1cc(Nc2cccc(F)c2)nc(-c2ccccn2)n1 | null | null | null |
128,229 | ord_dataset-d6b60b593b1c4668bc6843cd65a5d232 | null | 1985-01-01T00:04:00 | true | [CH2:1]([O:3][C:4]([C@@H:6]([NH:15][C@@H:16]([CH3:20])[C:17]([OH:19])=O)[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])[CH3:2].C1C(=O)N(O)C(=O)C1.C1(N=C=NC2CCCCC2)CCCCC1.[CH3:44][N:45]1[CH2:49][C@@H:48]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[NH:47][C:46]1=[O:57]>>[CH3:44][N:45]1[CH... | CCOC(=O)[C@H](CCc1ccccc1)N[C@@H](C)C(=O)O | CN1C[C@@H](C(=O)OC(C)(C)C)NC1=O | null | C(=NC1CCCCC1)=NC1CCCCC1 | O=C1CCC(=O)N1O | 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 | 560 mg of (2S)-2-[N-((1S)-1-ethoxycarbonyl-3-phenylpropyl)amino]propionic acid, 230 mg of 1-hydroxysuccinimide, 413 mg of dicyclohexylcarbodiimide and 400 mg of tert.-butyl (4S)-1-methyl-2-oxo-imidazolidine-4-carboxylate are treated in the same manner as described in Example 1-(1), whereby 650 mg of tert.-butyl (4S)-1-... | CCOC(=O)[C@H](CCc1ccccc1)N[C@@H](C)C(=O)N1C(=O)N(C)C[C@H]1C(=O)OC(C)(C)C | null | 70.5 | null |
162,521 | ord_dataset-f5dc3e448c204058b116bf1970695bef | null | 1987-01-01T00:09:00 | true | Cl[C:2]1[N:3]=[C:4]([N:14]2[CH2:19][CH2:18][S:17](=[O:20])[CH2:16][CH2:15]2)[C:5]2[N:11]=[CH:10][N:9]=[C:8]([NH:12][CH3:13])[C:6]=2[N:7]=1.[NH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>O1CCOCC1>[CH3:13][NH:12][C:8]1[C:6]2[N:7]=[C:2]([N:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[N:3]=[C:4]([N:14]3[CH2:19][CH2:18][... | CNc1ncnc2c(N3CCS(=O)CC3)nc(Cl)nc12 | C1CNCCN1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | null | This compound was prepared analogous to Example 118 from 2-chloro-8-methylamino-4-(1-oxido-thiomorpholino)-pyrimido-[5,4-d]-pyrimidine (m.p.: 278°-280° C.) and piperazine in dioxane at 80° C. | CNc1ncnc2c(N3CCS(=O)CC3)nc(N3CCNCC3)nc12 | null | null | null |
1,586,651 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | [O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:8]=[C:9]([CH:27]=[CH:28][CH:29]=2)[CH2:10][N:11]2[C:15]3=[N:16][C:17]([NH:20][C:21]4[CH:22]=[N:23][N:24]([CH3:26])[CH:25]=4)=[N:18][CH:19]=[C:14]3[CH:13]=[N:12]2)[CH2:3][CH2:2]1>CO.[Pd]>[CH3:26][N:24]1[CH:25]=[C:21]([NH:20][C:17]2[N:16]=[C:15]3[N:11]([CH2:10][C:9]4[CH:27]=[CH:28][CH:... | Cn1cc(Nc2ncc3cnn(Cc4cccc(C5=CCOCC5)c4)c3n2)cn1 | 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 | 8 | 1-(3-(3,6-dihydro-2H-pyran-4-yl)benzyl)-N-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine was dissolved in methanol (8 mL) and palladium on carbon was added under an inert atmosphere. The reaction mixture was stirred overnight at rt under a hydrogen atmosphere. The mixture was filtered over Celite, then ... | Cn1cc(Nc2ncc3cnn(Cc4cccc(C5CCOCC5)c4)c3n2)cn1 | null | 38 | null |
1,557,205 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | Br[CH:2]([CH3:11])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[CH3:12][C:13]1[C:14]2[N:15]([N:19]=[C:20]([C:22]3[CH:27]=[CH:26][N:25]=[C:24]([NH2:28])[CH:23]=3)[N:21]=2)[CH:16]=[CH:17][N:18]=1.C(N(CC)C(C)C)(C)C>C(O)C>[CH3:12][C:13]1[C:14]2[N:15]([N:19]=[C:20]([C:22]3[CH:27]=[CH:26][N:25]4[C:2]([CH3:11])=[C:3]([C... | Cc1nccn2nc(-c3ccnc(N)c3)nc12 | CC(Br)C(=O)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | 80 | null | 2-Bromopropiophenone (0.034 ml, 0.221 mmol) was added to a solution of 4-(8-methyl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)pyridin-2-amine (0.025 g, 0.111 mmol) in Ethanol (2.2 ml) and the mixture was heated at 80° C. for 40 hours. LC/MS analysis of the reaction mixture indicates reaction approximately 40% complete. The rea... | Cc1nccn2nc(-c3ccn4c(C)c(-c5ccccc5)nc4c3)nc12 | null | 18 | null |
967,822 | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | null | 2010-01-01T00:06:00 | true | [C:1]([O:5][C:6](=[O:22])[CH:7](P(OC)(OC)=O)[NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])([CH3:4])([CH3:3])[CH3:2].[C:23]([C:27]1[O:31][CH:30]=[N:29][C:28]=1[CH:32]=O)([CH3:26])([CH3:25])[CH3:24].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[C:1]([O:5][C:6]([C:7]([NH:8][C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:... | COP(=O)(OC)C(NC(=O)OC(C)(C)C)C(=O)OC(C)(C)C | CC(C)(C)c1ocnc1C=O | null | O=C([O-])[O-] | [Cs+] | 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 | 14 | To a solution of N-(tert-Butoxycarbonyl)-α-dimethylphosphonoglycine-tert-butyl ester (11.8 g, 34.68 mmol) and 5-tert-butyloxazole-4-carboxaldehyde (6.9 g, 45.08 mmol) in DMF (50 mL) was added Cs2CO3 (12.4 g, 38.15 mmol) under an argon atmosphere at room temperature. The reaction mixture was stirred for 14 h at room tem... | CC(C)(C)OC(=O)NC(=Cc1ncoc1C(C)(C)C)C(=O)OC(C)(C)C | null | 47.2 | null |
1,119,274 | ord_dataset-4226e9b4f9f845db967ed997270dcafc | null | 2011-01-01T00:12:00 | true | C([CH:8]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[C:20]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:19]=1)[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:10])C1C=CC=CC=1>CCOC(C)=O.[Pt]>[NH2:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][CH:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C... | O=C(c1ccccc1)C(Cc1ccccc1)Cc1ccc([N+](=O)[O-])c(OCc2ccccc2)c1 | null | null | [Pt] | 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 solution of 2-benzyl-3-(3-benzyloxy-4-nitrophenyl)-1-phenylpropan-1-one (200 mg) in EtOAc (5 mL) is hydrogenated over 5% Pt/C (15 mg) at 1 atm for 18 h. The catalyst is filtered and the filtrate evaporated to give the title compound as a gum: (M+1)+=422. | Nc1ccc(CC(C(=O)c2ccccc2)c2ccccc2)cc1OCc1ccccc1 | null | null | null |
1,673,682 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | [CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[C:20]([CH:21]=[O:22])=[CH:19][N:18]=[C:17]3[NH:23][CH:24]=[CH:25][C:16]=23)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34].O>CN(C)C=O>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14... | O=Cc1cnc2[nH]ccc2c1NC1CCN(Cc2ccccc2)CC1 | C[Si](C)(C)CCOCCl | null | [H-] | [Na+] | 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 | null | 0.5 | 4-[(1-Benzylpiperidin-4-yl)amino]-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (672 mg, 2.01 mmol) in N,N-dimethylformamide (5 mL) was mixed with sodium hydride (55 wt % dispersion in mineral oil, 436 mg, 10.0 mmol) under cooling with ice, and the reaction mixture was stirred for 30 minutes. The reaction mixture was stirre... | C[Si](C)(C)CCOCn1ccc2c(NC3CCN(Cc4ccccc4)CC3)c(C=O)cnc21 | null | 42 | null |
173,410 | ord_dataset-3844acbccc714c04ab757ec4fca10bd0 | null | 1988-01-01T00:06:00 | true | [Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10](Cl)=[O:11].[Cl-].[Al+3].[Cl-].[Cl-].[CH2:17]=[CH2:18]>C(Cl)Cl>[Cl:8][C:6]1[CH:5]=[C:4]2[C:3](=[C:2]([Cl:1])[CH:7]=1)[CH2:9][C:10](=[O:11])[CH2:18][CH2:17]2 | O=C(Cl)Cc1ccc(Cl)cc1Cl | C=C | null | [Al+3] | [Cl-] | 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 | 0 | 72 | 149.4 g of 2,4-dichlorophenylacetyl chloride dissolved in 200 ml of methylene chloride were added dropwise within 60 minutes to 115 g of aluminum chloride in 700 ml of methylene chloride while stirring at 0° to 5°. Thereafter, ethylene was introduced at between 0° and 5° during 30 minutes, whereupon the mixture was sti... | O=C1CCc2cc(Cl)cc(Cl)c2C1 | null | null | null |
434,171 | ord_dataset-386da077ab2340638cada986e2ef0770 | null | 1999-01-01T00:07:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][C:22]=1[Br:23])[O:6][CH:7]([C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=O)[C:8]([O:10][CH2:11][CH3:12])=[O:9].S(=O)(=O)(O)O>>[Br:23][C:22]1[C:3]([O:2][CH3:1])=[CH:4][C:5]2[O:6][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:20]=2... | CCOC(=O)C(=O)C(Oc1ccc(Br)c(OC)c1)C(=O)OCC | null | 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 | null | Diethyl 3-methoxy-4-bromophenoxyoxalacetate (D10) (7.8 g, 20 mmoles) was stirred with concentrated sulphuric acid (50 ml) for 30 mins. The mixture was then poured into ice water (500 ml) and extracted with diethyl ether (250 ml). The organics were washed with saturated aqueous sodium bicarbonate, dried (Na2SO4) and eva... | CCOC(=O)c1oc2cc(OC)c(Br)cc2c1C(=O)OCC | null | 44.3 | null |
1,403,449 | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | null | 2014-01-01T00:03:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[N:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][C@@H:18]3[CH3:30])=[CH:13][CH:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[N:7]=1>Cl.C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:12]=[CH:13][C:14]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][C@@H:18]3[CH3:30])=[CH:15]... | C[C@H]1CN(C(=O)OC(C)(C)C)CCN1c1ccc(Nc2cc(Cl)nn(C)c2=O)nc1 | null | null | Cl | 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 | 25 | 2 | A mixture of 117a (3.0 g, 6.9 mmol) and 4.0M HCl/ethanol (20 mL) was stirred at room temperature for 2 h. The mixture was then concentrated under reduced pressure to afford crude 117b as a yellow solid (2.5 g, 98%), which was used in the next step without further purification. MS-ESI: [M+H]+ 335.1. | C[C@H]1CNCCN1c1ccc(Nc2cc(Cl)nn(C)c2=O)nc1 | null | 108.2 | null |
1,225,931 | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | null | 2012-01-01T00:11:00 | true | [NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.C(N(CC)CC)C.[S:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[C:22](Cl)=[O:23]>ClCCl>[C:8]([C:5]1[N:6]=[CH:7][C:2]([NH:1][C:22]([C:18]2[S:17][CH:21]=[CH:20][CH:19]=2)=[O:23])=[CH:3][CH:4]=1)#[N:9] | N#Cc1ccc(N)cn1 | O=C(Cl)c1cccs1 | null | null | null | 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 | 0 | null | To a suspension of 5-amino-2-cyanopyridine (2.00 g, 16.8 mmol) in dry dichloromethane (50 mL) was added triethylamine (2.54 g, 25.21 mmol) and the mixture was stirred at 0° C. To the reaction mixture 2-thiophene carbonyl chloride (3.70 g, 25.21 mmol) was added drop wise over a period of 15 minutes, and the reaction mix... | N#Cc1ccc(NC(=O)c2cccs2)cn1 | null | 11.2 | null |
1,609,485 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | [F:1][C:2]([F:14])([F:13])[C:3]1[N:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1.CO.S(=O)(=O)(O)O.[CH2:22](O)[CH3:23]>>[CH2:22]([O:11][C:10](=[O:12])[CH2:9][C:6]1[CH:7]=[N:8][C:3]([C:2]([F:13])([F:1])[F:14])=[CH:4][CH:5]=1)[CH3:23] | CCO | O=C(O)Cc1ccc(C(F)(F)F)nc1 | null | O=S(=O)(O)O | 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 | 4.23 g (20.6 mmol) (6-trifluoromethylpyridin-3-yl)acetic acid [obtainable from [6-trifluoromethyl)pyridin-3-yl]methanol analogously to the reaction sequence of Examples 37A, 38A and 41] are initially introduced into 200 ml ethanol under argon, 0.2 ml concentrated sulfuric acid are added and the mixture is heated under ... | CCOC(=O)Cc1ccc(C(F)(F)F)nc1 | null | null | null |
1,460,757 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [F:1][C:2]([F:9])([F:8])[C:3]1[N:4]=[N:5][NH:6][N:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][C:18]([C:20]1[CH:24]=[C:23]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[N:22]([C:30]2[C:35]([Cl:36])=[CH:34][CH:33]=[CH:32][N:31]=2)[N:21]=1)=[O:19]>C(#N)C>[Cl:36][C:35]1[C:30]([N:22]2[C:23]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH... | FC(F)(F)c1nn[nH]n1 | CCOC(=O)c1cc(C(=O)CBr)nn1-c1ncccc1Cl | null | O=C([O-])[O-] | [K+] | 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 | 25 | 0.25 | 1.24 g (2.04 mmol) of 5-(trifluoromethyl)-2H-tetrazole and 348 mg (2.52 mmol) of potassium carbonate were initially charged in 15 ml of acetonitrile and stirred at RT for 15 min. 693 mg (1.57 mmol) of ethyl 3-(bromoacetyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylate, dissolved in 5 ml of acetonitrile, were added... | CCOC(=O)c1cc(C(=O)Cn2nnc(C(F)(F)F)n2)nn1-c1ncccc1Cl | null | null | null |
620,103 | ord_dataset-2952e63264f5422a84e12cca1e0541ee | null | 2003-01-01T00:12:00 | true | P(Cl)(Cl)(Cl)(Cl)[Cl:2].[Na+].[F:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][S:17]([O-:20])(=O)=[O:18])=[CH:11][CH:10]=1>C1(C)C=CC=CC=1.O>[F:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][S:17]([Cl:2])(=[O:20])=[O:18])=[CH:11][CH:10]=1 | O=S(=O)([O-])CCc1ccc(F)cc1 | ClP(Cl)(Cl)(Cl)Cl | null | [Na+] | 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 | 25 | 8 | Phosphorus pentachloride (5.6 g, 27 mmol) was added portionwise over 10 minutes to a stirred suspension of 2-(4-fluorophenyl)ethanesulfonic acid sodium salt (9 mmol, contaminated with sodium bromide, total weight 2.87 g) in dry toluene (15 ml) at room temperature. The reaction mixture was heated under reflux for 90 min... | O=S(=O)(Cl)CCc1ccc(F)cc1 | null | 34.9 | null |
1,692,509 | ord_dataset-c1e70ad912eb438f8d34b1dc681f809a | null | 2016-01-01T00:02:00 | true | [C:1]([O:5][C:6]([N:8]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][C:21]([O:23]C)=[O:22])=[CH:15][CH:14]=1)[S:9]([CH3:12])(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-]>C1COCC1.Cl>[C:1]([O:5][C:6]([N:8]([C:13]1[CH:14]=[CH:15][C:16]([CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[CH:17][CH:18]=1)[S:9]([CH3:12]... | COC(=O)CCc1ccc(N(C(=O)OC(C)(C)C)S(C)(=O)=O)cc1 | null | null | Cl | [Li+] | [OH-] | 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 | 6 | Methyl 3-(4-(N-(tert-butoxycarbonyl)methylsulfonamido)phenyl)propanoate (300 mg, 0.86 mmol) was dissolved in THF (3 ml), then LiOH 1N (2 ml) was added, and the mixture was stirred at RT for 6 hours. The reaction was diluted with HCl 1N, and the product was extracted with EtOAc. The organic phase was dried over Na2SO4 a... | CC(C)(C)OC(=O)N(c1ccc(CCC(=O)O)cc1)S(C)(=O)=O | null | 84.7 | null |
1,298,949 | ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c | null | 2013-01-01T00:05:00 | true | [I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[H-].[Na+].[CH2:11](Br)[CH:12]=[CH:13][CH3:14]>CN(C=O)C>[CH2:11]([O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[I:1])[CH:12]=[CH:13][CH3:14] | CC=CCBr | Oc1ccccc1I | 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 | 25 | 8 | An ice-cold solution of 2-iodophenol (10.0 g, 45.4 mmol) in DMF (100 mL) was added dropwise to a solution of NaH (2.16 g, 90.8 mmol) in DMF at 0° C. Crotylbromide (7.97 g, 59.0 mmol) was then added. The mixture was warmed to room temperature and stirred overnight. The reaction was quenched with water (50 mL) and the mi... | CC=CCOc1ccccc1I | null | 98 | null |
1,464,139 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | [Br:1][C:2]1[C:6]([C:7]#[N:8])=[C:5](Br)[S:4][C:3]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11].C(=O)([O-])[O-].[Cs+].[Cs+].[OH:21][CH2:22][CH:23]1[O:28][CH2:27][CH2:26][NH:25][CH2:24]1.O1CCCC1>O>[Br:1][C:2]1[C:6]([C:7]#[N:8])=[C:5]([N:25]2[CH2:26][CH2:27][O:28][CH:23]([CH2:22][OH:21])[CH2:24]2)[S:4][C:3]=1[C:10]([O:12][CH2:... | CCOC(=O)c1sc(Br)c(C#N)c1Br | OCC1CNCCO1 | null | O=C([O-])[O-] | [Cs+] | 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 | 90 | 4 | Ethyl 3,5-dibromo-4-cyanothiophene-2-carboxylate (0.360 g, 1.06 mmol), cesium carbonate (1.05 g, 3.21 mmol), 2-hydroxymethylmorpholine (137 mg, 1.17 mmol), and tetrahydrofuran (4.5 mL, 36 mmol) were combined in a 15 mL pressure vessel equipped with a stir bar. The vessel was sealed, and the r×n was heated @ 90° C. with... | CCOC(=O)c1sc(N2CCOC(CO)C2)c(C#N)c1Br | null | 41 | null |
652,325 | ord_dataset-fe016e2f90e741a590ad77fd5933161f | null | 2004-01-01T00:11:00 | true | [Br:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([F:13])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9].B(Br)(Br)Br.[CH2:18](O)[CH:19]=C>C(Cl)Cl>[Br:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([F:13])=[C:7]([CH:12]=1)[C:8]([O:10][CH2:11][CH:18]=[CH2:19])=[O:9] | COC(=O)c1cc(CBr)ccc1F | C=CCO | null | BrB(Br)Br | 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 | 8 | To a solution of methyl 5-bromomethyl-2-fluorobenzoate (12.49 g, 50.6 mmol) in methylene chloride (150 mL) at 0° C. is added BBr3 (5.26 mL, 55.62 mmol) slowly, via syringe. The solution is then warmed to room temperature over 2.5 hours, and then is cooled back down to 0° C., and allyl alcohol (103 mL, 1.52 mol) is adde... | C=CCOC(=O)c1cc(CBr)ccc1F | null | null | null |
1,412,326 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([NH2:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[S:13]1[CH:17]=[C:16]([C:18](O)=[O:19])[N:15]=[CH:14]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([NH:12][C:18]([C:16]3[N:15]=[CH:14][S:13][CH:17]=3)=[O... | Nc1cccc2ccc(Cl)nc12 | O=C(O)c1cscn1 | 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 | CCN(C(C)C)C(C)C | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | A solution of 2-chloroquinolin-8-amine (222 mg), thiazole-4-carboxylic acid (129 mg, 1 eq), HATU (570 mg, 1.5 eq), and DIEA (246 uL, 2.0 eq) in DMF (3 mL) was stirred at room temperature overnight. The product was precipitated by the addition of water (20 mL), the product was collected by filtration and recrystallized ... | O=C(Nc1cccc2ccc(Cl)nc12)c1cscn1 | null | 67 | null |
477,381 | ord_dataset-21c1b1c06c7e4e09a38b5b1c71a32e52 | null | 2000-01-01T00:10:00 | true | F[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[NH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>>[N:10]1([C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[C:4]#[N:5])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1 | C1CCNCC1 | N#Cc1ccccc1F | 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 | According to a similar manner to that in Reference Example 12, the title compound was synthesized from 2-fluorobenzonitrile and piperidine. | N#Cc1ccccc1N1CCCCC1 | null | null | null |
7,850 | ord_dataset-ad879e603f9440f6bfb7fbd18e5e8761 | null | 1976-01-01T00:06:00 | true | [C:1]1([N:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]2[N:13]=[C:12](Cl)[N:11]=[C:10](Cl)[N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:22]1([NH:28][C:29]#[N:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[Na]>CC(C)=O.O>[C:1]1([N:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]2[N:13]=[C:12]([N:28]([C:29]... | N#CNc1ccccc1 | Clc1nc(Cl)nc(N(c2ccccc2)c2ccccc2)n1 | null | [Na] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | O | null | null | null | null | null | null | null | null | null | 25 | 1 | To a solution of 31.7g (0.10 mole) of a 2-diphenylamino-4,6-dichloro-s-triazine in 325 ml of acetone at room temperature was added dropwise to a solution of 0.20 mole of sodium phenylcyanamide in 100 ml of water over a 30 minute period. After stirring for 1 hour at room temperature, the reaction mixture was heated at r... | N#CN(c1ccccc1)c1nc(N(C#N)c2ccccc2)nc(N(c2ccccc2)c2ccccc2)n1 | null | 106.1 | null |
405,301 | ord_dataset-55e306db9b6b4befbc22504c12b7113d | null | 1998-01-01T00:06:00 | true | [CH3:1][C:2]([Si:5]([CH3:42])([CH3:41])[O:6][CH:7]([C:22]1[CH:27]=[CH:26][C:25]([O:28]CC2C=CC=CC=2)=[C:24]([NH:36][S:37]([CH3:40])(=[O:39])=[O:38])[CH:23]=1)[CH2:8][NH:9][C@@H:10]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[C:11]([OH:13])=[O:12])([CH3:4])[CH3:3]>CO.[Pd]>[CH3:4][C:2]([Si:5]([CH3:41])(... | COc1ccc([C@H](NCC(O[Si](C)(C)C(C)(C)C)c2ccc(OCc3ccccc3)c(NS(C)(=O)=O)c2)C(=O)O)cc1 | 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 | 0.67 | A solution of (R), (S)-α-[[2-[((1,1-dimethylethyl)dimethylsilyl)oxy]-2-[4-phenylmethoxy-3-[(methylsulfonyl)amino]phenyl]ethyl]amino]-4-methoxy-benzeneacetic acid (4.04 g, 6.5 mmol) in MeOH (50 mL) containing 0.42 g of 10% Pd/C was sparged with H2 at 20° C. By TLC (10% MeOH/CH2Cl2), the reaction was complete after 40 mi... | COc1ccc([C@H](NCC(O[Si](C)(C)C(C)(C)C)c2ccc(O)c(NS(C)(=O)=O)c2)C(=O)O)cc1 | null | 111.4 | null |
1,637,036 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | CC(C)([O-])C.[K+].[C:7]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:14])[C:8]1C=CC=CC=1.[N:21](OCCC(C)C)=[O:22]>C(O)(C)(C)C>[O:14]=[C:7]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:8]=[N:21][OH:22] | CC(C)CCON=O | O=C(c1ccccc1)c1ccccc1 | null | CC(C)(C)[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)(C)O | null | null | null | null | null | null | null | null | null | null | null | null | A flask was charged with potassium tert-butoxide (58 mmol) and 63 mL of tert-butyl alcohol. The mixture was stirred until a solution was formed, and a solution of the appropriate benzophenone (50 mmol) in 35 mL of tert-butyl alcohol added dropwise over 15 min. The reaction mixture was stirred for 1 hr, and the neat iso... | O=C(C=NO)c1ccccc1 | null | null | null |
1,633,748 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | [CH:1]1([C:6]2[CH:11]=[C:10]([C:12]3[O:16][N:15]=[C:14]([C:17]4[CH:22]=[C:21]([CH3:23])[C:20]([O:24][CH2:25][C@@H:26]5[CH2:28][O:27]5)=[C:19]([CH2:29][CH3:30])[CH:18]=4)[N:13]=3)[CH:9]=[C:8]([O:31][CH3:32])[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C([O:35][C:36](=[O:41])[CH2:37][CH2:38][NH:39][CH3:40])C>>[CH:1]1([C:6]2[CH:... | CCOC(=O)CCNC | CCc1cc(-c2noc(-c3cc(OC)nc(C4CCCC4)c3)n2)cc(C)c1OC[C@@H]1CO1 | 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 is prepared starting from (S)-5-(2-cyclopentyl-6-methoxypyridin-4-yl)-3-(3-ethyl-5-methyl-4-(oxiran-2-ylmethoxy)phenyl)-1,2,4-oxadiazole and ethyl-3-(methylamino)-propanoate in analogy to Example 9; LC-MS: tR=0.95 min, [M+H]+=539.53; 1H NMR (CDCl3): δ 7.84 (s, 1H), 7.82 (s, 1H), 7.48 (s, 1H), 7.27 (s... | CCc1cc(-c2noc(-c3cc(OC)nc(C4CCCC4)c3)n2)cc(C)c1OC[C@@H](O)CN(C)CCC(=O)O | null | null | null |
1,663,745 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | Cl[CH2:2][C:3]([NH:5][CH2:6][C:7]1[N:8]=[C:9]2[C:14](=[C:15]3[C:20]=1[CH:19]=[CH:18][CH:17]=[CH:16]3)[CH:13]=[CH:12][CH:11]=[CH:10]2)=[O:4].[NH:21]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28][NH:27][CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH:13]1[C:14]2[C:9](=[N:8][C:7]([CH2:6][NH:5][C:3](=[O:4])[C... | O=C(CCl)NCc1nc2ccccc2c2ccccc12 | C1CNCCNCCNCCN1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | 25 | null | A solution of the chloro 9 (20.0 mg, 70.2 μmol) in anhydrous CHCl3 (5 mL) was added to a solution of cyclen (48.4 mg, 0.281 mmol) and triethylamine (11.7 μL, 84.2 μmol) in anhydrous CHCl3 (15 mL) under N2 (g). The reaction mixture was heated to reflux under N2 (g) for 23 hours. The reaction mixture was then allowed to ... | O=C(CN1CCNCCNCCNCC1)NCc1nc2ccccc2c2ccccc12 | null | 47.1 | null |
1,144,736 | ord_dataset-68715347640045adb1b09e6a04722b0e | null | 2012-01-01T00:03:00 | true | [CH:1]1[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH:11]([CH2:12][CH2:13][CH2:14][C:15]([O:17]CC)=[O:16])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Cl>CO>[CH:1]1[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH:11]([CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])[C:5]=2[CH:4]=[CH:3][CH:2]=1 | CCOC(=O)CCCC1CCCCc2ccccc21 | null | null | Cl | [Na+] | [OH-] | 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 | A solution of ethyl 4-(6,7,8,9-tetrahydro-5H-5-benzocycloheptenyl)butyrate (0.534 g) in methanol (10 ml) was added with 2 N aqueous sodium hydroxide (2 ml), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was added with 2 N aqueous hydrochloric acid and thereby made acidic, and the mix... | O=C(O)CCCC1CCCCc2ccccc21 | null | null | null |
1,118,913 | ord_dataset-4226e9b4f9f845db967ed997270dcafc | null | 2011-01-01T00:12:00 | true | [CH2:1]([O:3][C:4](=[O:14])[CH:5]([C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=1)[CH3:6])[CH3:2].[C:15]([S-:17])#[N:16].[K+].BrBr>CC(O)=O>[CH2:1]([O:3][C:4](=[O:14])[CH:5]([C:7]1[CH:8]=[CH:9][C:10]2[N:13]=[C:15]([NH2:16])[S:17][C:11]=2[CH:12]=1)[CH3:6])[CH3:2] | CCOC(=O)C(C)c1ccc(N)cc1 | N#C[S-] | null | BrBr | [K+] | 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 | 1 | A mixture of 3 (3.13 g, 1 mmol) in CH3COOH (15 ml) was cooled to −5□ in iced bath. A mixture KSCN (6.36 g, 4.04 mmol) in CH3COOH (15 ml) added to the flask that contained 4 and CH3COOH at −5° in iced bath. A solution of bromine (0.80 ml) in CH3COOH (10 ml) is added dropwise to a stirred mixture of 4, KSCN and CH3COOH a... | CCOC(=O)C(C)c1ccc2nc(N)sc2c1 | null | null | null |
816,207 | ord_dataset-50f99930fc41474db226bc80774b38df | null | 2008-01-01T00:04:00 | true | [CH3:1][C:2]([NH:8][CH2:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH3:21])[CH:18]=2)[N:13]=[CH:12][C:11]=1[Cl:22])([CH3:7])[C:3]([O:5]C)=O.[F:23][C:24]([F:36])([F:35])[O:25][C:26]1[CH:31]=[CH:30][C:29]([N:32]=[C:33]=[O:34])=[CH:28][CH:27]=1>>[CH3:7][C:2]1([CH3:1])[N:8]([CH2:9][C:10]2[C:19]3[C:14](=[CH:15][CH... | O=C=Nc1ccc(OC(F)(F)F)cc1 | COC(=O)C(C)(C)NCc1c(Cl)cnc2ccc(OC)cc12 | 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 is prepared according to the procedure described in Example 59, starting with 180 mg of methyl 2-methyl-2-[(3-chloro-6-methoxyquinol-4-ylmethyl)amino]propanoate instead of methyl 2-methyl-2-[(quinol-4-ylmethyl)amino]propanoate used in Example 59 and 267 mg of 4-(trifluoromethoxy)phenyl isocyanate. After pur... | COc1ccc2ncc(Cl)c(CN3C(=O)N(c4ccc(OC(F)(F)F)cc4)C(=O)C3(C)C)c2c1 | null | null | null |
1,616,260 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | [NH:1]1[C:5]([C:6]2[C:7]3[CH2:15][CH2:14][N:13]([C:16]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[C:19]=4[Cl:28])=[O:17])[CH2:12][C:8]=3[N:9]=[CH:10][N:11]=2)=[CH:4][CH:3]=[N:2]1.[H-].[Na+].[CH3:31]I>CN(C=O)C.O>[Cl:28][C:19]1[C:20]([C:24]([F:25])([F:27])[F:26])=[CH:21][CH:22]=[CH:23][C:18]=1[C:1... | O=C(c1cccc(C(F)(F)F)c1Cl)N1CCc2c(ncnc2-c2ccn[nH]2)C1 | CI | null | [H-] | [Na+] | 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 | null | null | To a solution of Example 18 (137 mg, 0.33 mmol) in DMF (3 mL) was added NaH, 60% dispersion in mineral oil (16 mg, 0.40 mmol). After 30 minutes MeI (0.03 mL, 0.40 mmol) was then added. After several hours the reaction was diluted with water and then extracted with EtOAc. The combined organic layers were washed with wat... | Cn1ccc(-c2ncnc3c2CCN(C(=O)c2cccc(C(F)(F)F)c2Cl)C3)n1 | null | 44 | null |
849,481 | ord_dataset-171b840ae6e84e45bab43b987d09f5c7 | null | 2008-01-01T00:11:00 | true | Br[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][N:3]=1.C([Li])CCC.[O:17]=[C:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]1>C(Cl)Cl>[OH:17][C:18]1([C:2]2[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][N:3]=2)[CH2:19][CH2:20][N:21]([C:24]([O:26][C:... | CC(C)(C)OC(=O)N1CCC(=O)CC1 | FC(F)(F)c1ccnc(Br)c1 | null | [Li]CCCC | 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 | -78 | 0.67 | To a slightly cloudy solution of 2-bromo-4-(trifluoromethyl)pyridine (4.0 g, 14.2 mmol) in dry methylene chloride (52.7 mL) cooled at −78° C. was added a 1.6 M solution of n-butyllithium in hexanes (9.65 mL). After being stirred for 40 min at −78° C., a solution of tert-butyl 4-oxo-1-piperidinecarboxylate (2.59 g, 12.9... | CC(C)(C)OC(=O)N1CCC(O)(c2cc(C(F)(F)F)ccn2)CC1 | null | 58.9 | null |
1,407,328 | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | null | 2014-01-01T00:03:00 | true | [OH:1][C:2]1[CH:3]=[C:4]([O:14][C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][CH:16]=2)[CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11](O)=[O:12])=[CH:7]2.[CH2:25]([S:32][CH:33]([CH:36]([O:39][CH3:40])[O:37][CH3:38])[CH2:34][NH2:35])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N... | COC(OC)C(CN)SCc1ccccc1 | CS(=O)(=O)c1ccc(Oc2cc(O)c3[nH]c(C(=O)O)cc3c2)cc1 | null | CCN=C=NCCCN(C)C | Cl | On1nnc2ccccc21 | 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 | null | To an ice-cooled and stirred mixture of 7-hydroxy-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylic acid (2.1 g) and 2-(benzylsulfanyl)-3,3-dimethoxypropan-1-amine (2.9 g) in N,N-dimethylformamide (50 mL) were added 1-hydroxybenzotriazole (1.1 g), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.6 ... | COC(OC)C(CNC(=O)c1cc2cc(Oc3ccc(S(C)(=O)=O)cc3)cc(O)c2[nH]1)SCc1ccccc1 | null | 50.1 | null |
961,638 | ord_dataset-ed65749688da45af8a8432967b017729 | null | 2010-01-01T00:05:00 | true | [CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[C:13]([N+:15]([O-:17])=[O:16])[CH:14]=1)[NH:11][C:10]([C:18]([O:20]CC)=[O:19])=[CH:9]2.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C.O1CCCC1.[OH-].[Na+]>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[C:13]([N+:15]([O-:17])=[O:16])[CH:14]=1)[NH:11][C:10]([C:18]... | CCOC(=O)c1cc2cc(OCCOC)cc([N+](=O)[O-])c2[nH]1 | null | null | O=C(O)CC(O)(CC(=O)O)C(=O)O | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | C1CCOC1 | null | null | null | null | null | null | null | null | null | 50 | 1.5 | Ethyl 5-(2-methoxyethoxy)-7-nitro-1H-indole-2-carboxylate (7.7 g) was dissolved in a mixed solvent of ethanol (75 mL) and tetrahydrofuran (75 mL), 1N aqueous sodium hydroxide solution (75 mL) was added to this solution, and the mixture was stirred at 50° C. for 1.5 hr. Aqueous citric acid solution was added to the reac... | COCCOc1cc([N+](=O)[O-])c2[nH]c(C(=O)O)cc2c1 | null | 97.2 | null |
1,179,136 | ord_dataset-0f9d2dbe929a45c3892ae75e81e99443 | null | 2012-01-01T00:06:00 | true | C([O:3][C:4](=O)[CH2:5][C:6]1[C:7]([CH2:18][CH:19]([CH3:21])[CH3:20])=[N:8][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[C:10]=1[CH3:11])C.[H-].C([Al+]CC(C)C)C(C)C>O1CCCC1>[CH2:18]([C:7]1[C:6]([CH2:5][CH:4]=[O:3])=[C:10]([CH3:11])[N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[N:8]=1)[CH:19]([CH3:21])[CH3:2... | CCOC(=O)Cc1c(CC(C)C)nn(-c2ccccn2)c1C | null | null | CC(C)C[Al+]CC(C)C | [H-] | 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 | -78 | 6 | Dissolve (3-isobutyl-5-methyl-1-pyridin-2-yl-1H-pyrazol-4-yl)-acetic acid ethyl ester (3.35 g, 11.11 mmol) in tetrahydrofuran (50 mL) and cool to −78° C. Add diisobutylaluminum hydride (33.3 mL, 33.3 mmol, 1 M in toluene) dropwise. Continue stirring at −78° C. for 6 hr. Quench with saturated aqueous potassium sodium ta... | Cc1c(CC=O)c(CC(C)C)nn1-c1ccccn1 | null | null | null |
265,649 | ord_dataset-a2ae447c4340438c8c3a827109aeb425 | null | 1993-01-01T00:04:00 | true | [N:1]1([C:6]2[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[OH-].[Na+].Br[CH2:16][CH2:17][CH2:18][Cl:19]>CO>[Cl:19][CH2:18][CH2:17][CH2:16][O:12][C:9]1[CH:10]=[CH:11][C:6]([N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[CH:7][CH:8]=1 | ClCCCBr | Oc1ccc(-n2ccnc2)cc1 | null | [Na+] | [OH-] | 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 | 70 | 18 | To a stirring solution of 4-(imidazol-1-yl)phenol (20 g, 125 mmol) and NaOH (5.0 g, 125 mmol) in methanol (600 mL) was added 1-bromo-3-chloropropane (49 mL, 500 mmol). The reaction was stirred for 18 hours at 70° C. under nitrogen, concentrated, and partitioned between 1.0N NaOH/CH2Cl2. The organic phase was dried and ... | ClCCCOc1ccc(-n2ccnc2)cc1 | null | 20.3 | null |
1,404,385 | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | null | 2014-01-01T00:03:00 | true | [OH:1][CH2:2][C@H:3]([NH:8][C:9]([C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1C(OC(C)(C)C)=O)=[O:10])[C:4]([O:6][CH3:7])=[O:5].Cl>O1CCOCC1>[OH:1][CH2:2][C@H:3]([NH:8][C:9]([C@@H:11]1[CH2:15][CH2:14][CH2:13][NH:12]1)=[O:10])[C:4]([O:6][CH3:7])=[O:5] | COC(=O)[C@H](CO)NC(=O)[C@@H]1CCCN1C(=O)OC(C)(C)C | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | 25 | 4 | (S)-Tert-butyl-2-((S)-3-hydroxy-1-methoxy-1-oxopropan-2-ylcarbamoyl)-pyrrolidine-1-carboxylate (3) (500 mg, 1.58 mmol) was dissolved in 1,4-dioxane (3 mL) and a HCl solution in dioxane (3.16 mL, 3.16 mmol) was added stirred at RT for 4 h. The volatiles were evaporated under reduced pressure to afford compound 4 (280 mg... | COC(=O)[C@H](CO)NC(=O)[C@@H]1CCCN1 | null | 82 | null |
712,230 | ord_dataset-c8a367b56b4f406b878f51867b157d19 | null | 2006-01-01T00:06:00 | true | [CH2:1]([C:9]1([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:21]2[CH:20]=[C:19](B(O)O)[CH:18]=[CH:17][C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Br:33][C:34]1[CH:46]=[CH:45][C:44]2[C:43]3[C:38](=[CH:39][C:40](Br)=[CH:41][CH:42]=3)[C:37]... | CCCCCCCCC1(CCCCCCCC)c2cc(Br)ccc2-c2ccc(Br)cc21 | CCCCCCCCC1(CCCCCCCC)c2ccccc2-c2ccc(B(O)O)cc21 | 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 | null | null | null | null | null | null | null | null | null | null | 90 | 48 | A mixture of 9,9-bis(n-octyl)fluoren-2-yl-boronic acid (2a) (2.0 g, 4.60 mmol), 2,7-dibromo-9,9-bis(n-octyl)fluorene (3a) (4.0 g, 7.32 mmol), Pd(PPh3)4 (50 mg, 0.043 mmol), Na2CO3 (2.0 M aqueous solution, 12.0 mL, 24.0 mmol), and toluene (20 mL) is stirred at 90° C. for 2 days. After the mixture is cooled to room tempe... | CCCCCCCCC1(CCCCCCCC)c2ccccc2-c2ccc(-c3ccc4c(c3)C(CCCCCCCC)(CCCCCCCC)c3cc(Br)ccc3-4)cc21 | null | 63.8 | null |
1,597,842 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][C:7]1[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][CH:8]=1.[ClH:20]>C(Cl)Cl.C(OCC)C>[ClH:20].[NH:10]1[CH2:9][CH:8]=[C:7]([CH2:6][C:2]2[S:1][CH:5]=[CH:4][N:3]=2)[CH2:12][CH2:11]1 | CC(C)(C)OC(=O)N1CC=C(Cc2nccs2)CC1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCOCC | null | null | null | null | null | null | null | null | null | 27.5 | 2 | To a stirred solution of tert-butyl 4-(thiazol-2-ylmethyl)-5,6-dihydropyridine-1(2H)-carboxylate (F) (1.5 g, 5.36 mmol) in CH2Cl2 (20 mL) was added 2M HCl in diethyl ether (5 mL) dropwise at 0° C. and the reaction mixture was allowed to stir at 20-35° C. for 2 h. Then the reaction mixture was rotary evaporated under va... | C1=C(Cc2nccs2)CCNC1 | null | null | null |
63,750 | ord_dataset-b1bf0950b5cb430abbb1d80744f5df84 | null | 1980-01-01T00:03:00 | true | [C:1]([NH:4]C1C=C(C=CC=1N=NC1C([N+]([O-])=O)=CC(Br)=CC=1Br)N(CC)CC)(=O)C.Br[C:30]1[CH:35]=[C:34]([N+:36]([O-:38])=[O:37])[CH:33]=[CH:32][C:31]=1[N:39]=[N:40][C:41]1[CH:59]=[CH:58][C:44]([N:45]([CH2:52][CH2:53][O:54][C:55](=[O:57])[CH3:56])[CH2:46][CH2:47][O:48][C:49](=[O:51])[CH3:50])=[CH:43][CH:42]=1>>[C:1]([C:30]1[CH... | CCN(CC)c1ccc(N=Nc2c(Br)cc(Br)cc2[N+](=O)[O-])c(NC(C)=O)c1 | CC(=O)OCCN(CCOC(C)=O)c1ccc(N=Nc2ccc([N+](=O)[O-])cc2Br)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 | 7 | When the 3-acetylamino-4-(2',4'-di-bromo-6'-nitrophenylazo)-N,N-diethylaniline employed in Example 9 was replaced by 4-(2'-bromo-4'-nitrophenylazo)-N,N-di(β-acetoxyethyl)aniline (4.8 parts) reaction was effectively complete in 7 hours at 90° C. Isolation of the product by the method of Example 9 gave 4-(2'-cyano-4'-nit... | CC(=O)OCCN(CCOC(C)=O)c1ccc(N=Nc2ccc([N+](=O)[O-])cc2C#N)cc1 | null | 15.95 | null |
982,419 | ord_dataset-35b56288528641309a040cc2b6710b61 | null | 2010-01-01T00:08:00 | true | C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[C:8]#[C:9][CH3:10].CN(C)C=O.[CH3:17][N:18]1[C:23](=[O:24])[C:22]2[NH:25][C:26]([N:28]3[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]3)=[N:27][C:21]=2[CH:20]=[N:19]1>O>[CH2:7]([N:25]1[C:22]2[C:23](=[O:24])[N:18]([CH3:17])[N:19]=[CH:20... | CC#CCBr | Cn1ncc2nc(N3CCN(C(=O)OC(C)(C)C)CC3)[nH]c2c1=O | 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 | 25 | 22 | 43.9 g of potassium carbonate and 27.8 ml of 2-butynyl bromide were successively added to a 5.5-L N,N-dimethylformamide solution of 88.4 g of t-butyl 4-(6-methyl-7-oxo-6,7-dihydro-1H-imidazo[4,5-d]pyridazin-2-yl)piperazine-1-carboxylate at 15° C. under a nitrogen atmosphere. The reaction solution was stirred at room te... | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2cnn(C)c(=O)c21 | null | null | null |
928,800 | ord_dataset-cc0899cd744f4f7f8e7f2463560faad1 | null | 2009-01-01T00:12:00 | true | [C:1]([O:5][C:6]([NH:8][CH:9]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=1)[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[NH2:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][CH:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:10]([O:12][CH3:13])=[O:11])=[CH:20][CH... | COC(=O)C(Cc1ccc([N+](=O)[O-])cc1)NC(=O)OC(C)(C)C | 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 | 2 | To a solution of methyl 2-[(tert-butoxycarbonyl)amino]-3-(4 nitrophenyl)propanoate 3 (69.4 g) and NH4HCO2 (6.5 equ.) in CH3OH (20 ml/g) is added 5% Pd/C (15% in weight, 10 g). The temperature rises to 40° C. and then decreases. After stirring for 2 h at room temperature, the solution is filtered over celite and the sol... | COC(=O)C(Cc1ccc(N)cc1)NC(=O)OC(C)(C)C | null | null | null |
966,827 | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | null | 2010-01-01T00:06:00 | true | Cl.[F:2][C:3]1[C:8]([F:9])=[CH:7][CH:6]=[CH:5][C:4]=1[C@H:10]1[CH2:16][N:15]2[CH:17]([CH2:20][CH3:21])[CH2:18][N:19]=[C:14]2[C@H:13]([NH:22]C(=O)OC(C)(C)C)[CH2:12][CH2:11]1>O1CCOCC1>[F:2][C:3]1[C:8]([F:9])=[CH:7][CH:6]=[CH:5][C:4]=1[C@H:10]1[CH2:16][N:15]2[CH:17]([CH2:20][CH3:21])[CH2:18][N:19]=[C:14]2[C@H:13]([NH2:22]... | CCC1CN=C2[C@H](NC(=O)OC(C)(C)C)CC[C@@H](c3cccc(F)c3F)CN21 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | 1 | Hydrochloric acid (4.0 M in dioxane; 3 mL, 12.0 mmol) was added to a solution of tert-butyl [(6S,9R)-6-(2,3-difluorophenyl)-3-ethyl-2,5,6,7,8,9-hexahydro-3H-imidazo[1,2-a]azepin-9-yl]carbamate (122 mg, 0.310 mmol) in 1,4-dioxane (3 mL). After 1 h, the reaction was concentrated to give the title compound as a bis hydroc... | CCC1CN=C2[C@H](N)CC[C@@H](c3cccc(F)c3F)CN21 | null | null | null |
625,590 | ord_dataset-e44331dc51de453ca14b7032593c1958 | null | 2004-01-01T00:02:00 | true | [C:1]([O:5][C:6]12[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:14][C:8]([C:16]([OH:18])=[O:17])([CH2:9]3)[CH2:7]1)[CH2:13]2)(=[O:4])[CH:2]=[CH2:3].[CH2:19]=[C:20]([CH3:22])[CH3:21].S(=O)(=O)(O)O>ClCCl>[C:1]([O:5][C:6]12[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:14][C:8]([C:16]([O:18][C:20]([CH3:22])([CH3:21])[CH3:19])=[O:17])([CH2:9... | C=C(C)C | C=CC(=O)OC12CC3CC(C1)CC(C(=O)O)(C3)C2 | null | O=S(=O)(O)O | 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 5 mmole of 1-acryloyloxy-3-carboxyadamantane thus obtained, 50 mmole of isobutene, 0.5 mmole of sulfuric acid and 50 ml of dichloromethane was stirred at 0° C. for 24 hours. After concentrating the reaction mixture, the concentrate was subjected to column chromatography on a silica gel to thereby yield the... | C=CC(=O)OC12CC3CC(C1)CC(C(=O)OC(C)(C)C)(C3)C2 | null | 81 | null |
165,133 | ord_dataset-12ef86aced0149e0917be82ce22190e2 | null | 1987-01-01T00:11:00 | true | [OH-].[K+].[NH2:3][C:4]1[CH:9]=[C:8]([Cl:10])[N:7]=[C:6]([S:11][CH3:12])[N:5]=1.Cl[C:14]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][C:17]([C:23]([F:26])([F:25])[F:24])=[C:16]([Cl:27])[C:15]=1[N+:28]([O-:30])=[O:29]>CS(C)=O>[Cl:27][C:16]1[C:15]([N+:28]([O-:30])=[O:29])=[C:14]([N:7]2[C:8]([Cl:10])=[CH:9][C:4]([NH2:3])=[N:5]... | O=[N+]([O-])c1cc(C(F)(F)F)c(Cl)c([N+](=O)[O-])c1Cl | CSc1nc(N)cc(Cl)n1 | null | [K+] | [OH-] | 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 | null | 7.9 parts of finely powdered 85% potassium hydroxide are dissolved in 70 ml of dimethylsulfoxide. To this solution is added dropwise a solution of 17.6 parts of 4-amino-6-chloro-2-methylmercaptopyrimidine in 80 ml of dimethylsulfoxide at about 15° C., and the reaction mixture is subsequently stirred for half an hour at... | CSC1N=C(N)C=C(Cl)N1c1c([N+](=O)[O-])cc(C(F)(F)F)c(Cl)c1[N+](=O)[O-] | null | null | null |
1,682,006 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | [OH:1][C@@H:2]1[CH2:25][CH2:24][C@@:23]2([CH3:26])[C@H:4](/[C:5](=[CH:29]\[CH3:30])/[C:6](=[O:28])[C@@H:7]3[C@@H:22]2[CH2:21][CH2:20][C@@:19]2([CH3:27])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:18])[CH2:13][CH2:14][C:15]([OH:17])=[O:16])[CH2:3]1.[OH-].[Na+]>[Pd].O>[OH:1][C@@H:2]1[CH2:25][CH2:24][C@@:23]2([CH3:26])... | C/C=C1/C(=O)[C@@H]2[C@H](CC[C@]3(C)[C@@H]([C@H](C)CCC(=O)O)CC[C@@H]23)[C@@]2(C)CC[C@@H](O)C[C@@H]12 | null | null | [Pd] | [Na+] | [OH-] | 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 | In one embodiment in Step 5, E-3α-hydroxy-6-ethylidene-7-keto-5β-cholan-24-oic acid (5), water, NaOH solution (e.g. 50% wt.), and Pd/C are mixed at about 5 bar of H2 gas and at a temperature at about 100° C. to about 105° C. until H2 uptake has ceased. The reaction mixture is cooled to about 40° C. to about 50° C. and ... | CC[C@H]1C(=O)[C@@H]2[C@H](CC[C@]3(C)[C@@H]([C@H](C)CCC(=O)O)CC[C@@H]23)[C@@]2(C)CC[C@@H](O)C[C@@H]12 | null | null | null |
1,298,093 | ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c | null | 2013-01-01T00:05:00 | true | [CH3:1][Si:2]([CH3:11])([CH3:10])[C:3]#[C:4][C:5]1[S:6][CH:7]=[CH:8][N:9]=1.[O:12]1[C:16]2([CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]2)[O:15][CH2:14][CH2:13]1>>[CH3:11][Si:2]([CH3:10])([CH3:1])[C:3]#[C:4][C:5]1[S:6][C:7]([C:19]2([OH:22])[CH2:20][CH2:21][C:16]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:17][CH2:18]2)=[CH:8... | C[Si](C)(C)C#Cc1nccs1 | O=C1CCC2(CC1)OCCO2 | 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 a white solid from 2-trimethylsilanylethynyl-thiazole, as prepared in the previous step, and 1,4-dioxa-spiro[4.5]decan-8-one using the procedure described in Step A of Example 33. | C[Si](C)(C)C#Cc1ncc(C2(O)CCC3(CC2)OCCO3)s1 | null | null | null |
959,092 | ord_dataset-ed65749688da45af8a8432967b017729 | null | 2010-01-01T00:05:00 | true | [Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:5]([O:15][CH3:16])[CH:4]=1.[F:17]C1C=CC(C2C=CC(CO)=CC=2OC)=CC=1>>[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([F:17])=[CH:11][CH:10]=2)=[C:5]([O:15][CH3:16])[CH:4]=1 | COc1cc(CO)ccc1-c1ccc(F)cc1 | COc1cc(CCl)ccc1-c1ccccc1 | 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 | Following the same procedure for the preparation of 4-Chloromethyl-2-methoxy-biphenyl, the title compound is prepared from (4′-Fluoro-2-methoxy-biphenyl-4-yl)-methanol (crude material from the previous step). The crude material is used directly in the next step. | COc1cc(CCl)ccc1-c1ccc(F)cc1 | null | null | null |
1,702,260 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | Br[C:2]1[C:10]2[N:9]3[CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:16])[C:8]3=[C:7]([CH3:17])[C:6]=2[CH:5]=[C:4]([C:18]#[N:19])[CH:3]=1.[N:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1>>[CH3:17][C:7]1[C:6]2[CH:5]=[C:4]([C:18]#[N:19])[CH:3]=[C:2]([C:23]3[CH:24]=[CH:25][N:20]=[CH:21][CH:22]=3)[C:10]=2[N:9]2[CH2:11][CH2:1... | Cc1c2n(c3c(Br)cc(C#N)cc13)CCCNC2=O | OB(O)c1ccncc1 | 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, white solid (64 mg, 81%), MS (ISP) m/z=317.5 [(M+H)+], mp 285° C., was prepared in accordance with the general method of example 1 from 7-bromo-11-methyl-1-oxo-2,3,4,5-tetrahydro-[1,4]diazepino[1,2-a]indole-9-carbonitrile (intermediate 17) (79.5 mg, 0.25 mmol) and commercially available pyridin-4-yl... | Cc1c2n(c3c(-c4ccncc4)cc(C#N)cc13)CCCNC2=O | null | null | null |
1,480,910 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [C:1]([O:5][C:6]([NH:8][C@H:9]([C:17]([NH2:19])=O)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].COC1C=CC(P2(=S)SP(C3C=CC(OC)=CC=3)(=S)[S:29]2)=CC=1>O1CCCC1>[NH2:19][C:17](=[S:29])[C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:10][C:11]1[CH:16]=[CH:15][CH:1... | CC(C)(C)OC(=O)N[C@@H](Cc1ccccc1)C(N)=O | COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1 | 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 | 25 | null | To a solution of #12 (14.060 g, 53.192 mmol, 1 eq.) in tetrahydrofuran (180 mL, 0.296 M), was added 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-dithione (Lawesson's reagent) (12.70 g, 31.40 mmol, 0.59 eq.) and the reaction was refluxed for 90 minutes. The reaction was cooled to room temperature and quenche... | CC(C)(C)OC(=O)N[C@@H](Cc1ccccc1)C(N)=S | null | 130.6 | null |
1,682,417 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | [NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[Br:14].[CH3:15][Si](C=[N+]=[N-])(C)C>ClCCl.CO>[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6]([O:8][CH3:15])=[O:7])=[CH:4][C:3]=1[Br:14] | C[Si](C)(C)C=[N+]=[N-] | Nc1c(Br)cc(C(=O)O)cc1[N+](=O)[O-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | ClCCl | null | null | null | null | null | null | null | null | null | 25 | null | To a solution of 4-amino-3-bromo-5-nitrobenzoic acid (3.65 g, 14.0 mmol) in dichloromethane (35 mL) and methanol (35 mL) at 0° C. was slowly added trimethylsilyl-diazomethane (8.74 mL, 17.5 mmol). The mixture was allowed to warm to ambient temperature and concentrated. Purification by silica gel chromatography (100% he... | COC(=O)c1cc(Br)c(N)c([N+](=O)[O-])c1 | null | 40 | null |
1,265,838 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | O[Li].O.[C:4]1([N:10]2[C:18]3[CH2:17][CH2:16][CH2:15][CH:14]([CH2:19][C:20]([O:22]CC)=[O:21])[C:13]=3[CH:12]=[N:11]2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O.CO>[C:4]1([N:10]2[C:18]3[CH2:17][CH2:16][CH2:15][CH:14]([CH2:19][C:20]([OH:22])=[O:21])[C:13]=3[CH:12]=[N:11]2)[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1 | CCOC(=O)CC1CCCc2c1cnn2-c1ccccc1 | null | null | [Li]O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | O | null | null | null | null | null | null | null | null | null | 25 | 1 | LiOH.H2O (120 mg, 2.85 mmol), dissolved in 1 ml of water, is added to a solution of ethyl 2-(4,5,6,7-tetrahydro-1-phenyl-1H-indazol-4-yl)acetate (808 mg, 2.85 mmol) in methanol (20 mL) and is stirred at room temperature for 1 hour following the reaction by means of TLC. The methanol is evaporated under reduced pressure... | O=C(O)CC1CCCc2c1cnn2-c1ccccc1 | null | 55.8 | null |
676,401 | ord_dataset-50cdc205280641d2a3e264f32908e3d0 | null | 2005-01-01T00:07:00 | true | CN1[CH2:7][CH:6]=[C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[NH:10][CH:9]=2)CC1.[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[C:17]([N:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][N:12]=2)[C:8]([CH:5]2[CH2:6][CH:7]=[CH:8][CH2:9][N:10]2[CH3:11])=[CH:9]1)(=[O:24])[C:18]1[CH:23]=[CH:22][C... | CN1CC=C(c2c[nH]c3ncccc23)CC1 | O=C(Cl)c1ccccc1 | 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 | (6.7 mg, 18%); from 3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)-1H-7-azaindole (25.0 mg, 0.12 mmol) and benzoyl chloride (28 μL, 0.24 mmol); HRMS-FAB+for C20H19N3O: calculated MH+:318.16064; found:318.16191. | CN1CC=CCC1c1cn(C(=O)c2ccccc2)c2ncccc12 | null | null | null |
1,289,575 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | Cl.Cl.[F:3][C:4]([F:24])([F:23])[C:5]([C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[CH:13][CH:12]=1)([OH:10])[C:6]([F:9])([F:8])[F:7].C(N(CC)CC)C.[N+:32]([C:35]1[CH:40]=[CH:39][C:38]([S:41](Cl)(=[O:43])=[O:42])=[CH:37][CH:36]=1)([O-:34])=[O:33]>C(Cl)Cl>[N+:32]([C:35]1[CH:36]=[CH:37][C:3... | OC(c1ccc(N2CCNCC2)cc1)(C(F)(F)F)C(F)(F)F | O=[N+]([O-])c1ccc(S(=O)(=O)Cl)cc1 | null | Cl | null | 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 | 0 | null | A 25-mL round-bottomed flask was cooled to 0° C. and charged with 1,1,1,3,3,3-hexafluoro-2-(4-(1-piperazinyl)phenyl)-2-propanol dihydrochloride (250 mg, 0.62 mmol, Example 91, Step 1), CH2Cl2 (5 mL) and triethylamine (0.26 mL, 1.87 mmol). 4-Nitrobenzenesulfonyl chloride (166 mg, 0.75 mmol, Sigma-Aldrich, St. Louis, Mo.... | O=[N+]([O-])c1ccc(S(=O)(=O)N2CCN(c3ccc(C(O)(C(F)(F)F)C(F)(F)F)cc3)CC2)cc1 | null | 56.5 | null |
958,017 | ord_dataset-ed65749688da45af8a8432967b017729 | null | 2010-01-01T00:05:00 | true | [CH3:1][C:2]1([CH3:19])[C:10]2[C:5](=[CH:6][C:7]([N+:15]([O-:17])=[O:16])=[C:8]([NH:11]C(=O)C)[CH:9]=2)[NH:4][C:3]1=[O:18].Cl[CH2:21][C:22]1[S:26][C:25]([CH3:27])=[N:24][C:23]=1[CH3:28].C([O-])([O-])=O.[K+].[K+].C1CCN2C(=NCCC2)CC1>CO>[NH2:11][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][C:7]=1[N+:15]([O-:17])=[O:16])[N:4]([CH2:21]... | Cc1nc(C)c(CCl)s1 | CC(=O)Nc1cc2c(cc1[N+](=O)[O-])NC(=O)C2(C)C | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCC2=NCCCN2CC1 | CO | null | null | null | null | null | null | null | null | null | null | null | Analogously to general procedure (I) N-(3,3-dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide (1.77 g) is alkylated using 5-chloromethyl-2,4-dimethyl-thiazole (1.09 g; 6.74 mmol) (Zh. Obshch. Khim. 1956, engl. transl. 3835) and K2CO3 (1.05 g; 7.41 mmol) at 60° C. for 3 days. After aqueous work-up the crude ma... | Cc1nc(C)c(CN2C(=O)C(C)(C)c3cc(N)c([N+](=O)[O-])cc32)s1 | null | 61.8 | null |
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