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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
140,560 | ord_dataset-a2a0fbbcd49a46ffaa432d7ceae8a506 | null | 1986-01-01T00:02:00 | true | [NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.Cl.[CH3:7][CH:8]1[CH2:12]OC(=O)[O:9]1>>[OH:9][CH:8]([CH3:12])[CH2:7][N:1]1[CH:5]=[N:4][CH:3]=[N:2]1 | c1nc[nH]n1 | CC1COC(=O)O1 | 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 | 0 | null | The starting material may be prepared as follows. A mixture of 1,2,4-triazole (5 g.) and 4-methyl-1,3-dioxolan-2-one was heated at 150° for 18 hours. Concentrated aqueous hydrochloric acid (8 ml.) was added dropwise to the ice-cooled mixture and the mixture was washed with chloroform. The aqueous phase was neutralised ... | CC(O)Cn1cncn1 | null | null | null |
1,135,960 | ord_dataset-aaeaab5f3720492494c1cbbdd0ed2820 | null | 2012-01-01T00:02:00 | true | [CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6]([N:8]1[CH2:13][CH:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[CH2:11][CH:10]([C:24](O)=[O:25])[CH2:9]1)=[O:7].O[N:28]=[C:29]([NH2:33])[CH:30]([CH3:32])[CH3:31]>>[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6]([N:8]1[CH2:13][CH:12]([C:14]2[CH:15]=[CH:16][C... | COCCNC(=O)N1CC(C(=O)O)CC(c2ccc(C(F)(F)F)cc2)C1 | CC(C)C(N)=NO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 100 mg (0.267 mmol) of the compound from Example 105A and 51 mg (0.497 mmol) of N′-hydroxy-2-methylpropanimidamide were reacted according to the General Method 2. Diastereomer separation of 83 mg of the cis/trans isomer mixture according to Method 14C gave 60.5 mg of the title compound and 6.7 mg of the trans isomer. | COCCNC(=O)N1CC(c2ccc(C(F)(F)F)cc2)CC(c2nc(C(C)C)no2)C1 | null | 51.4 | null |
1,660,647 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:16][OH:17])[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1.C(N(CC)CC)C>C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:16][O:17][S:24]([C:21]1[CH:22]=[CH:23][C:18]([CH3:28])... | COC(=O)CC[C@@H](CO)NC(=O)OC(C)(C)C | Cc1ccc(S(=O)(=O)Cl)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 25 | 8 | Methyl (4S)-4-[(tert-butoxy)carbonylamino]-5-hydroxypentanoate (9.11 mmol, 2.25 g) was dissolved in 30 mL of methylene chloride. p-Toluenesulfonyl chloride (9.1 mmol, 1.7 g) and triethylamine (27.33 mmol, 3.8 mL) were added and the reaction was stirred at room temperature overnight. Solvent was removed in vacuo and cru... | COC(=O)CC[C@@H](COS(=O)(=O)c1ccc(C)cc1)NC(=O)OC(C)(C)C | null | 54.2 | null |
889,291 | ord_dataset-11068b1e475b4c5b82e56726ab0dddb7 | null | 2009-01-01T00:07:00 | true | [Br:1][C:2]1[C:3]([F:12])=[C:4]([F:11])[C:5](F)=[C:6]([CH:9]=1)[CH:7]=[O:8].C(N(CC)CC)C.[CH3:20][C@H:21]1[O:26][C@H:25]([CH3:27])[CH2:24][NH:23][CH2:22]1.Cl>C(#N)C>[Br:1][C:2]1[C:3]([F:12])=[C:4]([F:11])[C:5]([N:23]2[CH2:22][CH:21]([CH3:20])[O:26][CH:25]([CH3:27])[CH2:24]2)=[C:6]([CH:9]=1)[CH:7]=[O:8] | O=Cc1cc(Br)c(F)c(F)c1F | C[C@@H]1CNC[C@@H](C)O1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 25 | null | 5-Bromo-2,3,4-trifluoro-benzaldehyde (10 g, 41.8 mmol) was dissolved in dry acetonitrile (70 mL). Triethylamine (6.4 mL, 46.0 mmol) was added, followed by trans-2,6-dimethylmorpholine (BASF, 5.3 g, 46 mmol). The mixture was refluxed for 24 hours, then cooled to room temperature, and treated with 1N HCl (58 mL). The ace... | CC1CN(c2c(C=O)cc(Br)c(F)c2F)CC(C)O1 | null | 90.6 | null |
1,471,894 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | CS(O[CH:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[O:19][CH:20]=[CH:21][N:22]=3)=[CH:14][CH:13]=2)[CH2:7]1)(=O)=O.[NH2:23][C@@H:24]1[CH2:29][CH2:28][CH2:27][CH2:26][C@H:25]1[NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34]>C(#N)C>[O:19]1[CH:20]=[CH:21][N:22]=[C:18]1[C:15]1[CH:16]=... | CS(=O)(=O)OC1CCCN(c2ccc(-c3ncco3)cc2)C1 | CC(C)(C)OC(=O)N[C@@H]1CCCC[C@H]1N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | 120 | 0.5 | To a solution of 1-(4-(oxazol-2-yl)phenyl)piperidin-3-yl methane sulfonate (110 mg, 0.341 mmol) in acetonitrile (4 mL) was added tert-butyl (1R,2R)-2-aminocyclohexylcarbamate (110 mg, 0.512 mmol). The reaction was stirred in a microwave at 120° C. for 30 min. After this time, LC/MS showed two pairs of products formed. ... | CC(C)(C)OC(=O)N[C@@H]1CCCC[C@H]1NC1CCCN(c2ccc(-c3ncco3)cc2)C1 | null | null | null |
713,931 | ord_dataset-c8a367b56b4f406b878f51867b157d19 | null | 2006-01-01T00:06:00 | true | C[O:2][C:3]1[C:4]([CH3:36])=[C:5]([C:27]([O:34]C)=[C:28]([O:32][CH3:33])[C:29]=1[O:30][CH3:31])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])=[C:11]([CH:20]=1)[C:12]([N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)=[O:13].O=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].... | COC(=O)COc1ccc(Cc2c(C)c(OC)c(OC)c(OC)c2OC)cc1C(=O)N1CCOCC1 | null | null | O=[N+]([O-])[O-] | [Ce+4] | [NH4+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | O | null | null | null | null | null | null | null | null | null | null | null | N-[5-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-(methoxycarbonylmethyloxy)benzoyl]morpholine (0.240 g, 0.478 mmol) was dissolved in a mixed solution of acetonitrile (12 ml) and water (4 ml) and after adding thereto CAN (0.655 g, 1.20 mmol) at room temperature, the solution was stirred at room temperature for 1 hour. The r... | COC(=O)COc1ccc(CC2=C(C)C(=O)C(OC)=C(OC)C2=O)cc1C(=O)N1CCOCC1 | null | 79.7 | null |
69,124 | ord_dataset-cb0fdfa937234c78b020ec878a93b94c | null | 1980-01-01T00:08:00 | true | C([NH:8][CH:9]([CH:11]1[O:16][C:15]2[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=2[O:13][CH2:12]1)[CH3:10])C1C=CC=CC=1>CO.Cl.[Pd]>[O:16]1[C:15]2[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=2[O:13][CH2:12][CH:11]1[CH:9]([NH2:8])[CH3:10] | CC(NCc1ccccc1)C1COc2ccccc2O1 | null | null | [Pd] | Cl | 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 | In 50 ml of methanol was dissolved 7 g of pure N-benzyl-1-(1,4-benzodioxan-2-yl)ethylamine (i1 '). After adding one drop of ethanolic hydrochloric acid and 0.5 g of 10% palladium charcoal to the solution, and catalytic reduction was performed at normal pressure until the absorption of hydrogen gas stopped. Then, pallad... | CC(N)C1COc2ccccc2O1 | null | 94.5 | null |
1,220,022 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | [F:1][C:2]1[CH:38]=[CH:37][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]4[CH:29]=[CH:28][N:27]=[C:26]5[NH:30][N:31]=[CH:32][C:25]=45)=[CH:19][CH:18]=3)=[O:15])=[CH:9][C:8]=2[C:33]([F:36])([F:35])[F:34])=[CH:4][CH:3]=1.CC[C:41]([C:43](Cl)=[O:44])=[O:42]>ClCCl.C1COCC... | CCC(=O)C(=O)Cl | O=C(Nc1ccc(Oc2ccnc3[nH]ncc23)cc1)Nc1ccc(Oc2ccc(F)cc2)c(C(F)(F)F)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | C1CCOC1 | null | null | null | null | null | null | null | null | null | 70 | 3 | 1-[4-(4-Fluorophenoxy)-3-trifluoromethyl-phenyl]-3-[4-(1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenyl]urea (50 mg, 0.15 mmol) was dissolved in dichloromethane (5 mL) and THF (3 mL), and ethyloxalyl chloride (70 μL) was added thereto. The resulting mixture was stirred at 70° C. for 3 hours. The reaction solution was concentra... | O=C1C(=O)N(c2ccc(Oc3ccc(F)cc3)c(C(F)(F)F)c2)C(=O)N1c1ccc(Oc2ccnc3[nH]ncc23)cc1 | null | 20 | null |
233,427 | ord_dataset-ed79ebfb2fff4cdbbc3a609c8edeac11 | null | 1991-01-01T00:08:00 | true | [Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.Cl.[H][H]>>[CH:10]1[C:11]2[C:6](=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:7]=[CH:8][CH:9]=1.[ClH:1] | Clc1cccc2ccccc12 | [H][H] | 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 | High conversions of 1-chloro- or 1-bromonaphthalene coupled with a long catalyst life can be achieved by the zeolites used according to the invention. The conversion of 1-chloronaphthalene over an amorphous aluminosilicate, in spite of an HCl atmosphere, dropped from 51 to 41% in the course of 4 hours (temperature 400°... | c1ccc2ccccc2c1 | null | null | null |
1,315,632 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | [CH:1]([NH2:4])([CH3:3])[CH3:2].[I-].[Na+].CS(O[CH2:12][C:13]1[CH:14]=[C:15]([NH:23][C:24]([N:26]2[C:34]3[C:29](=[CH:30][C:31]([O:35][C:36]4[C:37]5[CH2:45][CH2:44][N:43](C(OC(C)(C)C)=O)[CH2:42][C:38]=5[N:39]=[CH:40][N:41]=4)=[CH:32][CH:33]=3)[CH:28]=[CH:27]2)=[O:25])[CH:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:18]=1... | CC(C)(C)OC(=O)N1CCc2c(ncnc2Oc2ccc3c(ccn3C(=O)Nc3cc(COS(C)(=O)=O)cc(C(F)(F)F)c3)c2)C1 | CC(C)N | null | [I-] | [Na+] | 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 | 0.75 | To a solution of the above mixture (0.15 g, 0.227 mmol) in 3 mL of DCM, isopropyl amine (0.06 mL, 0.680 mmol) is added followed by sodium iodide (0.1 g, 0.68 mmol). After 45 min, LC-MS shows that tert-butyl 4-(1-(3-((methylsulfonyloxy)methyl)-5-(trifluoromethyl)phenylcarbamoyl)-1H-indol-5-yloxy)-5,6-dihydropyrido[3,4-d... | CC(C)NCc1cc(NC(=O)n2ccc3cc(Oc4ncnc5c4CCNC5)ccc32)cc(C(F)(F)F)c1 | null | null | null |
13,754 | ord_dataset-7f88a5da29d74264aae5239be74b3981 | null | 1976-01-01T00:10:00 | true | CC(O[CH2:5][C:6]1[CH2:15][S:14][C@@H:9]2[C@H:10]([NH2:13])[C:11](=[O:12])[N:8]2[C:7]=1[C:16]([OH:18])=[O:17])=O.[SH:19][C:20]1[N:24]([CH3:25])[CH:23]=[N:22][N:21]=1>>[NH2:13][CH:10]1[C:11](=[O:12])[N:8]2[C:7]([C:16]([OH:18])=[O:17])=[C:6]([CH2:5][S:19][C:20]3[N:24]([CH3:25])[CH:23]=[N:22][N:21]=3)[CH2:15][S:14][C@H:9]1... | Cn1cnnc1S | CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](N)[C@H]2SC1 | null | null | null | null | null | null | null | 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-Amino-3-(4-methyl-1,2,4-triazol-3-ylthiomethyl)-3-cephem-4-carboxylic acid was prepared from 7-ACA and 3-mercapto-4-methyl-1,2,4-triazole according to the first paragraph of Example 1. | Cn1cnnc1SCC1=C(C(=O)O)N2C(=O)C(N)[C@H]2SC1 | null | null | null |
1,542,029 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | [F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.C(O)(=O)[CH2:11][C:12]([OH:14])=[O:13].N1CCCCC1>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:11][C:12]([OH:14])=[O:13])[CH:7]=[CH:8][CH:9]=1 | O=Cc1cccc(F)c1 | O=C(O)CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCNCC1 | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | 3-Fluorobenzaldehyde (5 g, 40.28 mmol) in pyridine (50 mL) was reacted with malonic acid (5.4 g, 52.3 mmol) and piperidine (343 mg, 4.0 mmol) at 75° C. for 12 hours to afford 6.6 g (96.9%) of the crude product which was used in the next step without further purification. | O=C(O)C=Cc1cccc(F)c1 | null | 98.6 | null |
1,524,951 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | Cl[CH2:2][C:3]#[N:4].BrCC1CCCCO1.[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]2([C:25]3=[CH:26][C:27]4[O:31][CH2:30][O:29][C:28]=4[CH:32]=[C:24]3[O:23][CH2:22]2)[C:14]1=[O:33]>>[O:33]=[C:14]1[C:15]2([C:25]3=[CH:26][C:27]4[O:31][CH2:30][O:29][C:28]=4[CH:32]=[C:24]3[O:23][CH2:22]2)[C:16]2[C:21](=[CH:20][C... | N#CCCl | O=C1Nc2ccccc2C12COc1cc3c(cc12)OCO3 | null | BrCC1CCCCO1 | null | null | null | null | null | 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 as described in EXAMPLE 4 and making non-critical variations using chloroacetonitrile to replace 2-(bromomethyl)tetrahydro-2H-pyran, and spiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one to replace 5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2″(1′H)-one, (2′-oxospiro[furo[2,... | N#CCN1C(=O)C2(COc3cc4c(cc32)OCO4)c2ccccc21 | null | null | null |
1,384,166 | ord_dataset-31641fb65b34430fa7435229b949b604 | null | 2014-01-01T00:01:00 | true | [CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.Cl[C:17]1([C:29]2[C:30]([O:35][CH2:36][CH3:37])=[N:31][CH:32]=[CH:33][CH:34]=2)[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([C:26]#[N:27])[CH:24]=2)[NH:19][C:18]1=[O:28].CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>ClCCl>[CH2:3... | CN1CCN(Cc2ccc(N)cc2)CC1 | CCOc1ncccc1C1(Cl)C(=O)Nc2ccc(C#N)cc21 | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 2 | 4-(4-Methyl-piperazin-1-ylmethyl)phenylamine (425 mg, 2.07 mmol) was added to a solution of 3-chloro-3-(2-ethoxypyridin-3-yl)-2-oxo-2,3-dihydro-1H-indole-5-carbonitrile (500 mg, 1.59 mmol) in dichloromethane (50 ml) and DIPEA (0.27 ml, 159 mmol) at 0° C. The reaction mixture was stirred at room temperature for 2 h and ... | CCOc1ncccc1C1(Nc2ccc(CN3CCN(C)CC3)cc2)C(=O)Nc2ccc(C#N)cc21 | null | 103.1 | null |
558,369 | ord_dataset-f483e698250b4da0a84f425c7bfa965a | null | 2002-01-01T00:08:00 | true | [CH3:1][C:2]1([CH3:16])[C:7]2[CH:8]=[C:9](B(O)O)[CH:10]=[CH:11][C:6]=2[NH:5][C:4](=[O:15])[O:3]1.Br[C:18]1[N:23]=[C:22]([CH2:24][C:25]#[N:26])[CH:21]=[CH:20][CH:19]=1>>[CH3:1][C:2]1([CH3:16])[C:7]2[CH:8]=[C:9]([C:18]3[N:23]=[C:22]([CH2:24][C:25]#[N:26])[CH:21]=[CH:20][CH:19]=3)[CH:10]=[CH:11][C:6]=2[NH:5][C:4](=[O:15])... | CC1(C)OC(=O)Nc2ccc(B(O)O)cc21 | N#CCc1cccc(Br)n1 | null | null | null | null | null | null | null | 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-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)pyridin-2-yl]acetonitrile was prepared, according to the procedure of Example 5 using (1,4-dihydro-4,4-dimethyl-2-oxo-2H-3,1-benzoxazin-6-yl)boronic acid and (6-bromo-2-pyridyl)acetonitrile (J. Org. Chem. 1988, 53, 786-790), as an off-white solid: mp 210-212.5° ... | CC1(C)OC(=O)Nc2ccc(-c3cccc(CC#N)n3)cc21 | null | null | null |
662,884 | ord_dataset-5a3d853c53674888a5691dce2e398792 | null | 2005-01-01T00:03:00 | true | CC1(C)C(C)(C)OB([C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH:11]=[CH:12][NH:13]3)O1.Br[C:20]1[CH:21]=[C:22]([CH2:26][C:27]([OH:29])=[O:28])[CH:23]=[CH:24][CH:25]=1.[OH-].[Na+]>C1COCC1.[Pd].C(OCC)(=O)C>[NH:13]1[C:14]2[C:10](=[C:9]([C:20]3[CH:21]=[C:22]([CH2:26][C:27]([OH:29])=[O:28])[CH:23]=[CH:24][CH:25]=3)[CH:17]=[... | O=C(O)Cc1cccc(Br)c1 | CC1(C)OB(c2cccc3[nH]ccc23)OC1(C)C | null | [Pd] | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 70 | null | To a mixture of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole (15.52 g, 63.72 mmol), and 3-bromo-phenylacetic acid (13.78 g, 63.72 mmol) in THF (192 mL) were added Palladium catalyst Pd(PPh3)4 (2.21 g, 1.9 mmol) and the freshly prepared sodium hydroxide solution (7.65 g in 90 mL of water). The system was d... | O=C(O)Cc1cccc(-c2cccc3[nH]ccc23)c1 | null | 84.3 | null |
1,705,056 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | [Br:1][C:2]1[C:10]2[O:9][CH:8]=[C:7]([CH3:11])[C:6]=2[C:5]([F:12])=[C:4]([F:13])[CH:3]=1.C1C(=O)[N:18](Br)[C:16](=O)C1.[C-]#N.[Na+].[OH-].[Na+]>O.C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[C:10]2[O:9][CH:8]=[C:7]([CH2:11][C:16]#[N:18])[C:6]=2[C:5]([F:12])=[C:4]([F:13])[CH:3]=1 | Cc1coc2c(Br)cc(F)c(F)c12 | O=C1CCC(=O)N1Br | null | [C-]#N | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | ClC(Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | 50 | 0.5 | To the compound (98.8 mg, 0.400 mmol) of Step 1 of Example 21, NBS (78.3 mg, 0.440 mmol), and a catalytic amount of BPO, carbon tetrachloride (4 mL) was added, and heated under reflux overnight. The resultant was returned to room temperature, and the solvent was distilled away under reduced pressure. The resulting resi... | N#CCc1coc2c(Br)cc(F)c(F)c12 | null | 36 | null |
332,277 | ord_dataset-1558660634294cc8ad7e01746e9083fd | null | 1996-01-01T00:06:00 | true | C([Li])CCC.[C:6]1([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CN(C)[CH:21]=[O:22].OS(O)(=O)=O>CCOCC>[O:12]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=1[CH:21]=[O:22])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1 | c1ccc(Oc2ccccc2)cc1 | CN(C)C=O | null | O=S(=O)(O)O | [Li]CCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | null | null | null | null | null | null | null | null | null | null | 0 | 1.5 | At room temperature, under an argon atmosphere, n-butyllithium (15.45 mL of a 2.5M solution in hexanes, 38.61 mmol) was added to a solution of diphenyl ether (5.0 g; 29.38 mmol) in 100 mL of ether, and the reaction mixture was gently refluxed for 4 hrs. After cooling to 0° C., N,N-dimethylformamide (22.73 mL; 0.293 mol... | O=Cc1ccccc1Oc1ccccc1 | null | 68.7 | null |
364,332 | ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | null | 1997-01-01T00:05:00 | true | [N:1]([CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]1[C:13]([O:14][CH3:15])=N[C@H](C(C)C)C(OC)=[N:9]1)=[N+:2]=[N-:3].Cl.[OH2:22].N>O1CCOCC1>[NH2:9][C@@H:8]([CH2:7][CH2:6][CH2:5][CH2:4][N:1]=[N+:2]=[N-:3])[C:13]([O:14][CH3:15])=[O:22] | O | COC1=N[C@H](C(C)C)C(OC)=N[C@H]1CCCCN=[N+]=[N-] | null | Cl | N | 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 | 8 | 1-Azido-4-[(2R,5S)-3,6-dimethoxy-2-isopropyl-2,5-dihydro-5-pyrazinyl]butane (2.17 g, 7.72 mmol) was dissolved in 30 ml dioxane and a solution of 1.28 ml conc. HCl in 30 ml water (15.45 mmol) was added dropwise, the mixture stirred under argon at ambient temperature overnight. Ammonia solution was added until pH 9 was r... | COC(=O)[C@@H](N)CCCCN=[N+]=[N-] | null | null | null |
617,606 | ord_dataset-2952e63264f5422a84e12cca1e0541ee | null | 2003-01-01T00:12:00 | true | [CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][C:4]=1[O:10][CH2:11][CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)C=1.[C:23]1([CH:29]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:30](Cl)=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C>CC(N(C)C)=O>[CH3:1][O:2][C:3]1[CH... | COc1ccc(N)cc1OCCc1ccc2ccccc2c1 | O=C(Cl)C(c1ccccc1)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)N(C)C | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 25 | 16 | N-[4-methoxy-3-(naphthylmethoxy)phenyl]-2,2-diphenylethanamide (Exemplary Compound 49) was prepared using the same experimental conditions used to prepare Example 52 (Scheme X). From 4-methoxy-3-(2-naphthylethoxy)phenylamine (350 mg, 1.25 mmol) and diphenylacetyl chloride (290 mg, 1.25 mmol) in 10 mL of dimethyl acetam... | COc1ccc(NC(=O)C(c2ccccc2)c2ccccc2)cc1OCc1cccc2ccccc12 | null | null | null |
815,359 | ord_dataset-50f99930fc41474db226bc80774b38df | null | 2008-01-01T00:04:00 | true | [CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([OH:24])CC2C(F)=CC=CC=2Cl)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:31][O:32][C:33]1[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][C:34]=1[CH2:35][Mg]Cl>>[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]([C:2... | OC(Cc1c(F)cccc1Cl)(c1ccccc1)C1CN(Cc2ccccc2)CCO1 | COc1ccc(OC)c(C[Mg]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 | The procedure for the synthesis of example 18a, 1-(4-Benzyl-morpholin-2-yl)-2-(2-chloro-6-fluoro-phenyl)-1-phenyl-ethanol, using 2,5-dimethoxybenzyl magnesium chloride as starting material (available from Rieke Metals) was followed making non-critical variations, to yield the title compound. This material was used in s... | COc1ccc(OC)c(CC(O)(c2ccccc2)C2CN(Cc3ccccc3)CCO2)c1 | null | null | null |
1,389,509 | ord_dataset-31641fb65b34430fa7435229b949b604 | null | 2014-01-01T00:01:00 | true | [N:1]1[CH:6]=[C:5](/[CH:7]=[CH:8]/[C:9]([O:11][CH3:12])=[O:10])[CH:4]=[N:3][CH:2]=1>CO.[Pd]>[N:1]1[CH:6]=[C:5]([CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:4]=[N:3][CH:2]=1 | COC(=O)/C=C/c1cncnc1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | A solution of methyl (2E)-3-(5-pyrimidinyl)-2-propenoate (19.2 g, 117 mmol) and Pd/C (2 g, 1.879 mmol) in methanol (100 mL) was stirred under H2 at 50° C. overnight. The mixture was filtered through a pad of celite and concentrated to give the crude title compound as yellow oil (18 g, 55.6% yield). LCMS: rt=1.11 min, [... | COC(=O)CCc1cncnc1 | null | 92.6 | null |
1,634,087 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | [CH2:1]([N:8]1[C:13]([CH3:15])([CH3:14])[CH2:12][N:11]([C:16]([C:18]2[CH:23]=[C:22]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:25]=3OC)[N:21]=[C:20]3[N:34]([CH:38]4[CH2:43][CH2:42][CH2:41][CH2:40][O:39]4)[N:35]=[C:36]([CH3:37])[C:19]=23)=O)[C:10]([CH3:45])([CH3:44])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][... | COc1ccc(-c2cc(C(=O)N3CC(C)(C)N(Cc4ccccc4)CC3(C)C)c3c(C)nn(C4CCCCO4)c3n2)c(OC)c1 | C1CCOC1 | null | B | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CSC | null | null | null | null | null | null | null | null | null | null | null | null | To a solution of 1.54 g of (4-benzyl-2,2,5,5-tetramethyl-piperazin-1-yl)-[6-(4-methoxy-methoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-yl]-methanone in 9 ml of dry THF 20 ml of borane-dimethylsulfide complex (1 M in DCM) was added slowly at r.t., and the reaction was heated to reflux for ... | COCOc1ccc(-c2cc(CN3CC(C)(C)N(Cc4ccccc4)CC3(C)C)c3c(C)nn(C4CCCCO4)c3n2)cc1 | null | 96 | null |
444,322 | ord_dataset-ba7561dae3884c07a8beddd0b9f1222e | null | 1999-01-01T00:10:00 | true | [CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[OH:14])=[CH:4][CH:3]=1.[H-].[Na+].F[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1.O>CN(C)C=O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:14][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=... | O=[N+]([O-])c1ccc(F)cc1 | Cc1ccc(-c2ccccc2O)cc1 | 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 | 25 | 0.5 | A solution of 184 mg (1.0 mmol) of 4-methyl-2'-hydroxy-1,1'-biphenyl (Example 12, Step C) in 3 mL of dimethylformamide was treated with 55 mg of 60% sodium hydride (33 mg NaH, 1.4 mmol). The reaction mixture was stirred at room temperature for 30 minutes then treated with 169 mg (1.19 mmol) of 1-fluoro-4-nitrobenzene. ... | Cc1ccc(-c2ccccc2Oc2ccc([N+](=O)[O-])cc2)cc1 | null | 89 | null |
1,417,665 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | [CH:1]1([N:6]2[C:15]3[N:14]=[C:13]([NH:16][C:17]4[CH:18]=[CH:19][C:20]([C:27]([O-:29])=[O:28])=[C:21]5[C:25]=4[O:24][CH:23]([CH3:26])[CH2:22]5)[N:12]=[CH:11][C:10]=3[N:9]([CH3:30])[C:8](=[O:31])[C@H:7]2[CH2:32][CH3:33])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Li+].Cl>CO.O1CCCC1>[CH:1]1([N:6]2[C:15]3[N:14]=[C:13]([NH:16][C:... | CC[C@@H]1C(=O)N(C)c2cnc(Nc3ccc(C(=O)[O-])c4c3OC(C)C4)nc2N1C1CCCC1 | null | null | Cl | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CO | null | null | null | null | null | null | null | null | null | null | 12 | 7-[[(7R)-8-Cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2-methyl-2,3-dihydrobenzofuran-4-carboxylate 30c (100 mg, 0.21 mmol) and 1 M lithium hydroxide solution were dissolved in 50 mL of the mixture solvent of methanol and tetrahydrofuran (V/V=1:1). The reaction solution was stirred for 12 hours followed ... | CC[C@@H]1C(=O)N(C)c2cnc(Nc3ccc(C(=O)O)c4c3OC(C)C4)nc2N1C1CCCC1 | null | 94.9 | null |
1,685,332 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | [H-].[Na+].[I:3][C:4]1[CH:5]=[N:6][NH:7][CH:8]=1.Br[CH2:10][C:11]1[CH:16]=[CH:15][NH:14][C:13](=[O:17])[CH:12]=1>C1COCC1>[I:3][C:4]1[CH:5]=[N:6][N:7]([CH2:10][C:11]2[CH:16]=[CH:15][NH:14][C:13](=[O:17])[CH:12]=2)[CH:8]=1 | O=c1cc(CBr)cc[nH]1 | Ic1cn[nH]c1 | null | [H-] | [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 | 0.5 | Sodium hydride (19 mg, 0.48 mmol, 60 wt %) was added to a solution of 4-iodo-1H-pyrazole (47 mg, 0.24 mmol) in THF (2 mL) at 0° C. After 30 minutes, 4-(bromomethyl)pyridin-2(1H)-one (30 mg, 0.16 mmol) was added. The mixture was stirred at 25° C. for 12 hours. The organic layer was dried over anhydrous sodium sulfate, f... | O=c1cc(Cn2cc(I)cn2)cc[nH]1 | null | null | null |
767,094 | ord_dataset-7a8649d55889427e85b208ae89475895 | null | 2007-01-01T00:04:00 | true | C(O[C:4](=[O:31])[CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH:13]([CH3:15])[CH3:14])[CH:10]=[CH:9][C:8]=1[CH2:16][CH2:17][NH:18][S:19]([C:22]1[CH:27]=[C:26]([C:28]#[N:29])[CH:25]=[CH:24][C:23]=1[OH:30])(=[O:21])=[O:20])C.O.[NH2:33][NH2:34]>C(O)C>[C:28]([C:26]1[CH:25]=[CH:24][C:23]([OH:30])=[C:22]([S:19]([NH:18][CH2:17][CH2:16]... | NN | CCOC(=O)COc1cc(C(C)C)ccc1CCNS(=O)(=O)c1cc(C#N)ccc1O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | O | null | null | null | null | null | null | null | null | null | null | null | Ethyl[2-[2-(5-cyano-2-hydroxybenzenesulfonylamino)-ethyl]-5-isoproylphenoxy]acetate (0.266 g) was dissolved in 5 mL of ethanol. To the solution was added 0.087 mL of hydrazine monohydrate at room temperature, and the mixture was refluxed for 1 hour. The solvent was removed under reduced pressure to give 0.258 g of 5-cy... | CC(C)c1ccc(CCNS(=O)(=O)c2cc(C#N)ccc2O)c(OCC(=O)NN)c1 | null | null | null |
1,409,472 | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | null | 2014-01-01T00:03:00 | true | [NH2:1][C:2]1[CH:6]=[CH:5][N:4]([C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=2)[N:3]=1.C(O)(=O)C.[CH:19]1([CH:22]=O)[CH2:21][CH2:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH:19]1([CH2:22][NH:1][C:2]2[CH:6]=[CH:5][N:4]([C:7]3[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=3)[N:3]=2)[CH2:21][CH2:20]1 | N#Cc1ccc(-n2ccc(N)n2)cc1 | O=CC1CC1 | 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 | ClCCCl | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | Dissolve 4-(3-amino-pyrazol-1-yl)-benzonitrile (200 mg) in 1,2-dichloroethane (12 mL). Add acetic acid (0.36 mL) and cyclopropanecarboxaldehyde (0.08 mL, 1.06 mmol) and stir the mixture at room temperature under a nitrogen atmosphere for 40 min. Add sodium triacetoxyborohydride (674 mg, 3.18 mmol) and stir for 3 h at r... | N#Cc1ccc(-n2ccc(NCC3CC3)n2)cc1 | null | 53.8 | null |
84,006 | ord_dataset-7bed824f566d4af0b51d74d386b14bd6 | null | 1981-01-01T00:07:00 | true | [C:1]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]1[CH:31]=[CH:30][C:24]([C:25]([O:27]CC)=[O:26])=[CH:23][CH:22]=1)([O:3]C)=[O:2].[OH-].[K+].C(O)C.Cl>O>[C:1]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH... | CCOC(=O)c1ccc(NCCCCCCCCCCCCCCCC(=O)OC)cc1 | null | null | Cl | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCO | null | null | null | null | null | null | null | null | null | null | null | A solution of 8.8 g. of ethyl 4-(15-carbomethoxypentadecylamino)benzoate, 4.5 g. of potassium hydroxide, and 10 ml. of water in 90 ml. of ethanol is stirred at 75° for 10 hours, cooled, diluted with water, brought to pH 4 with dilute hydrochloric acid, and filtered. The solid is dried and crystallized from acetic acid ... | O=C(O)CCCCCCCCCCCCCCCNc1ccc(C(=O)O)cc1 | null | null | null |
1,214,798 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | [C@H:1]12[CH2:6][C@H:5]1[CH2:4][C@@H:3]([CH2:7][NH:8][C:9]([C:11]1[N:18]3[C:14]([S:15][CH:16]=[CH:17]3)=[N:13][C:12]=1[CH3:19])=[O:10])[NH:2]2.[F:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[S:31][C:30]([CH3:32])=[N:29][C:28]=2[C:33](O)=[O:34])=[CH:23][CH:22]=1>>[F:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]2[S:31][C:30]([CH3:32... | Cc1nc2sccn2c1C(=O)NC[C@@H]1C[C@@H]2C[C@@H]2N1 | Cc1nc(C(=O)O)c(-c2ccc(F)cc2)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 | prepared by reaction of 6-methyl-imidazo[2,1-b]thiazole-5-carboxylic acid [(1S,3S,5S)-2-aza-bicyclo[3.1.0]hex-3-ylmethyl]-amide with 5-(4-fluoro-phenyl)-2-methyl-thiazole-4-carboxylic acid. LC-MS (basic): tR=1.29 min; [M+H]+=496.1. | Cc1nc(C(=O)N2[C@H](CNC(=O)c3c(C)nc4sccn34)C[C@@H]3C[C@@H]32)c(-c2ccc(F)cc2)s1 | null | null | null |
106,046 | ord_dataset-e7e9fe3dd42b4f499d5b17fe63bbf336 | null | 1983-01-01T00:06:00 | true | [OH:1][C:2]1[C:15]2[C@:14]34[CH2:16][CH2:17][N:18]([CH3:19])[C@@H:8]([C@@H:9]3[CH2:10][CH2:11][C:12](=[O:20])[CH2:13]4)[CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:21](OC(=O)C)(=[O:23])[CH3:22]>N1C=CC=CC=1>[C:21]([O:1][C:2]1[C:15]2[C@:14]34[CH2:16][CH2:17][N:18]([CH3:19])[C@@H:8]([C@@H:9]3[CH2:10][CH2:11][C:12](=[O:20])[CH2:... | CC(=O)OC(C)=O | CN1CC[C@]23CC(=O)CC[C@H]2[C@H]1Cc1cccc(O)c13 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | 25 | 8 | A mixture of (-)-4-hydroxy-N-methylmorphinan-6-one (500 mg, 1.84 mmol), acetic anhydride (5 ml), and pyridine (10 ml) was stirred at room temperature overnight. Acetic anhydride and pyridine were evaporated under vacuum and the residue was taken into toluene and evaporated again. The crude product was taken into CHCl3 ... | CC(=O)Oc1cccc2c1[C@]13CCN(C)[C@H](C2)[C@@H]1CCC(=O)C3 | null | null | null |
1,542,285 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | [NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8][CH3:9])=[O:7].[H-].[Na+].[F:12][CH2:13][CH2:14]I.O>CN(C=O)C>[F:12][CH2:13][CH2:14][N:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8][CH3:9])=[O:7] | COC(=O)c1ccc[nH]1 | FCCI | 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 | Methyl 1H-pyrrole-2-carboxylate (3.0 g, 23.3 mmol) was solved in DMF (40 ml). Sodium hydride (1.40 g, 34.9 mmol, 60% in oil) was added and the mixture was stirred for 30 minutes at room-temperature. 1-Fluoro-2-iodoethane (4.1 g, 23.2 mmol) was added and the mixture was stirred for 15 h at 50° C. Water was added and the... | COC(=O)c1cccn1CCF | null | null | null |
547,955 | ord_dataset-e967d076b4894c2c854795f019ed3c39 | null | 2002-01-01T00:06:00 | true | [O:1]=[C:2]([C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)[CH:3]([CH2:9]N1CCCCC1)[CH2:4][C:5]([O:7][CH3:8])=[O:6]>C(O)C.Cl.O1CCOCC1>[N:18]1[CH:19]=[CH:20][CH:21]=[C:16]([C:2]([C:3](=[CH2:9])[CH2:4][C:5]([O:7][CH3:8])=[O:6])=[O:1])[CH:17]=1 | COC(=O)CC(CN1CCCCC1)C(=O)c1cccnc1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | CCO | null | null | null | null | null | null | null | null | null | null | null | A solution of methyl 4-oxo-3-(piperidylmethyl)-4-(3-pyridyl)butanoate (4 g) in ethanol (10 mL) and 4N HCl/dioxane (4.0 mL) was heated at 80° C. for 12 hrs. The reaction mixture was concentrated and purified on flash chromatography (SIO2, CHCl3: MeOH: CH3COOH=10: 1:0.5) to give 2.28 g of the title compound. | C=C(CC(=O)OC)C(=O)c1cccnc1 | null | 80.7 | null |
390,476 | ord_dataset-44d518e567bd4c039d77233023f78bb2 | null | 1998-01-01T00:01:00 | true | [Li+].[CH3:2][CH:3]([N-]C(C)C)[CH3:4].[CH3:9][CH:10]([CH3:34])[CH2:11][C:12]1([CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]1=[O:25].C(Br)C=C>C1COCC1>[CH3:9][CH:10]([CH3:34])[CH2:11][C:12]1([CH:26]([C:3]([CH3:4... | CC(C)CC1(CC(=O)OC(C)(C)C)CCN(CCc2ccccc2)C1=O | CC(C)[N-]C(C)C | null | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | C=CCBr | null | null | null | null | null | null | null | null | null | -78 | 0.75 | LDA (2.0M, 7.7 mL, 16 mmol) is added to a solution of tert-butyl 3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetate (EXAMPLE 1, step 3; 4.62 g, 12.9 mmol) and THF (45 mL) at -78° C. The solution is stirred at -78° C. for 45 minutes and allyl bromide (1.3 mL, 16 mmol) is added. The solution is allowed to wa... | C=C(C)C(C(=O)OC(C)(C)C)C1(CC(C)C)CCN(CCc2ccccc2)C1=O | null | 85.9 | null |
236,708 | ord_dataset-1acb071a357f438ea5993287375971cf | null | 1991-01-01T00:10:00 | true | C[O:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][C:15]=1[O:16]C)[C:6]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[O:7].Br>>[OH:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][C:15]=1[OH:16])[C:6]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[O:7] | COc1ccc(C(=O)CCC(=O)O)cc1OC | null | null | Br | null | null | null | null | null | 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 5-carboxymethyl-4-(3,4-disubstituted phenyl)-2-mercaptothiazole derivative can be produced by reacting veratrole with succinic anhydride in the presence of anhydrous aluminum chloride to obtain 3-(3,4-dimethoxybenzoyl)propionic acid, subjecting the propionic acid to demethylation with hydrobromic acid to obtain 3-(3,... | O=C(O)CCC(=O)c1ccc(O)c(O)c1 | null | null | null |
977,375 | ord_dataset-f886e51ba1484c76a94bce1482f1eab9 | null | 2010-01-01T00:07:00 | true | [CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[N:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][N:21]2C(=O)C3C(=CC=CC=3)C2=O)[C:15](=[O:32])[CH2:14]1.O.NN>CCO>[NH2:21][CH2:20][CH2:19][N:16]1[CH2:17][CH2:18][N:13]([C:6]2[C:5]3[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[N:4]=3)[N:9]=[CH:8][C... | COc1ccc2nccc(N3CCN(CCN4C(=O)c5ccccc5C4=O)C(=O)C3)c2n1 | null | null | NN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | O | null | null | null | null | null | null | null | null | null | null | 2 | To a solution of 2-(2-{4-[6-(methyloxy)-1,5-naphthyridin-4-yl]-2-oxo-1-piperazinyl}ethyl)-1H-isoindole-1,3(2H)-dione (100 mg, 0.232 mmol) in EtOH (2 mL) was added hydrazine hydrate (120 μL, 3.85 mmol). After 2 h at 85° C., the solution was concentrated and the residue purified by column chromatography (silica, 5-10% Me... | COc1ccc2nccc(N3CCN(CCN)C(=O)C3)c2n1 | null | 65.8 | null |
781,538 | ord_dataset-8034115bd2ec4d3e95bd3ff7cfde0bde | null | 2007-01-01T00:07:00 | true | C(N(CC)CC)C.[NH2:8][C:9]1[CH:10]=[C:11]([C:23](=[O:25])[CH3:24])[CH:12]=[C:13]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:14]=1[O:15][CH2:16][O:17][CH3:18].[C:26](Cl)(=[O:28])[CH3:27]>O1CCCC1>[C:23]([C:11]1[CH:12]=[C:13]([C:19]([CH3:20])([CH3:21])[CH3:22])[C:14]([O:15][CH2:16][O:17][CH3:18])=[C:9]([NH:8][C:26](=[O:28])[CH3:... | CC(=O)Cl | COCOc1c(N)cc(C(C)=O)cc1C(C)(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | 0.17 | Triethylamine (60 ml, 430 mmol) was added to a solution of the 1-[3-amino-5-(tert-butyl)-4-(methoxymethoxy)phenyl]-1-ethanone (53.9 g, 215 mmol) in tetrahydrofuran (270 ml) while cooling on ice under a nitrogen atmosphere and then acetyl chloride (23 ml, 323 mmol) was added dropwise. After stirring at the same temperat... | COCOc1c(NC(C)=O)cc(C(C)=O)cc1C(C)(C)C | null | 89.1 | null |
611,560 | ord_dataset-5c4ee54447b84205a10f9c0473172972 | null | 2003-01-01T00:10:00 | true | [N+:1]([C:4]1[CH:5]=[C:6]([C:14](=[O:16])[CH3:15])[CH:7]=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10])([O-:3])=[O:2].B.C1COCC1.C1COCC1>O>[N+:1]([C:4]1[CH:5]=[C:6]([CH:14]([OH:16])[CH3:15])[CH:7]=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10])([O-:3])=[O:2] | COC(=O)c1cc(C(C)=O)cc([N+](=O)[O-])c1 | null | null | B | null | 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 | 25 | 24 | An oven-dried round bottom flask fitted with a magnetic stirring bar was charged with compound methyl 5-nitro-3-acetylbenzoate (0,5 g), prepared in step 1 of Intermediate 13, BH3THF (1 M solution in THF, 5 mol equiv.), and anhydrous THF. After stirring at room temperature for 24 h, H2O (20 mL) was added and the solutio... | COC(=O)c1cc(C(C)O)cc([N+](=O)[O-])c1 | null | null | null |
739,982 | ord_dataset-437aa6654d5044ddaef3346dc4c6e08a | null | 2006-01-01T00:11:00 | true | [CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([N:22]2[CH2:27][CH2:26][CH:25]([OH:28])[CH2:24][CH2:23]2)[N:9]([CH3:21])[C:10](=[O:20])[C:11]=1[O:12]CC1C=CC=CC=1)=[O:5])[CH3:2].[F:29][C:30]([F:35])([F:34])[C:31](O)=[O:32]>>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([N:22]2[CH2:27][CH2:26][CH:25]([O:28][C:31](=[O:32])[C:30]([F:35])([F:3... | CCOC(=O)c1nc(N2CCC(O)CC2)n(C)c(=O)c1OCc1ccccc1 | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 10 | 5-Benzyloxy-2-(4-hydroxypiperidin-1-yl)-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxylic acid ethyl ester (0.760 g, 1.96 mmol) was treated with trifluroacetic acid (20 mL) at ambient temperature. After 10 h, the reaction mixture was concentrated and purified on silica gel column using 2–5% MeOH/CH2Cl2 to afford desire... | CCOC(=O)c1nc(N2CCC(OC(=O)C(F)(F)F)CC2)n(C)c(=O)c1O | null | null | null |
1,536,847 | ord_dataset-8d5c200bca27407ab9febe7598e16458 | null | 2015-01-01T00:01:00 | true | [Cl:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([C:13](=O)[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]#[N:21])[CH:15]=2)[CH:3]=1.O.[NH2:24][NH2:25]>CCO.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5]([C:6](=[O:7])[NH:24][N:25]=[C:13]2[C:14]2[CH:15]=[C:16]([CH:17]=[CH:18][CH:19]=2)[C:20]#[N:21])=[CH:9][C:10]=1[O:11... | COc1cc(C(=O)O)c(C(=O)c2cccc(C#N)c2)cc1Cl | NN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCO | null | null | null | null | null | null | null | null | null | null | null | A solution of 4-chloro-2-(3-cyanobenzoyl)-5-methoxybenzoic acid (3.0 g, 9.50 mmol) in hydrazine hydrate (0.6 mL 11.4 mmol) and EtOH (40 mL) was heated at 80° C. for 2 h. The reaction mixture was diluted with water (100 mL), and the precipitate was filtered and dried to obtain 3-(7-chloro-6-methoxy-4-oxo-3,4-dihydrophth... | COc1cc2c(=O)[nH]nc(-c3cccc(C#N)c3)c2cc1Cl | null | 20.3 | null |
1,255,184 | ord_dataset-266f60b4555945d6afb2d2bdf5fa04e0 | null | 2013-01-01T00:02:00 | true | [C:1]1([C:7]2[CH:12]=[C:11]([C:13]3[N:17]4[CH:18]=[CH:19][C:20]([CH:22]5[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]5)=[CH:21][C:16]4=[N:15][CH:14]=3)[CH:10]=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:35](Cl)(=[O:37])[CH3:36].C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]1([C:7]2[CH:12]=[C:11]([C:13]3[N:17]4[CH:18]=[... | CC(=O)Cl | c1ccc(-c2cc(-c3cnc4cc(C5CCNCC5)ccn34)ccn2)cc1 | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 25 | 2 | To a solution of 3-(2-phenyl-pyridin-4-yl)-7-piperidin-4-yl-imidazo[1,2-a]pyridine (Ex. 1.198) (1.0 eq, 0.20 mmol, 80 mg) in CH2Cl2 (2 ml) is added triethylamine (3 eq, 0.61 mmol, 0.09 ml) and acetyl chloride (1.5 eq, 0.31 mmol, 0.02 ml) and the reaction mixture is stirred at room temperature for 2 h. The reaction mixt... | CC(=O)N1CCC(c2ccn3c(-c4ccnc(-c5ccccc5)c4)cnc3c2)CC1 | null | null | null |
1,324,179 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | [CH2:1]([O:3][C:4](=[O:20])[C:5]#[C:6][C:7]1[S:11][C:10]([NH:12]C(OC(C)(C)C)=O)=[N:9][CH:8]=1)[CH3:2].FC(F)(F)C(O)=O.C(=O)(O)[O-]>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:20])[C:5]#[C:6][C:7]1[S:11][C:10]([NH2:12])=[N:9][CH:8]=1)[CH3:2] | CCOC(=O)C#Cc1cnc(NC(=O)OC(C)(C)C)s1 | null | null | O=C([O-])O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | 25 | 8 | (2-tert-Butoxycarbonylamino-thiazol-5-yl)-propynoic acid ethyl ester (1.2 g, 4.049 mmol) was dissolved in DCM (20 ml), trifluoroacetic acid (4.617 g, 40.93 mmol) was added in drop wise fashion at 0° C. After complete addition the reaction was allowed to stir for overnight at room temperature. Additional 3 ml of TFA was... | CCOC(=O)C#Cc1cnc(N)s1 | null | null | null |
517,856 | ord_dataset-a495451286334c5c9bbcbd48a00c1350 | null | 2001-01-01T00:09:00 | true | C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][O:21][C:22](=[O:24])[CH3:23])=[CH:15][CH:14]=3)=[O:12])=[C:9]([C:25]3[CH:30]=[CH:29][C:28]([O:31]C)=[CH:27][CH:26]=3)[S:8][C:7]=2[CH:33]=1.C(S)C.[Cl-].[Al+3].[Cl-].[Cl-]>>[OH:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11]([C:13]3[CH:14]=... | COc1ccc(-c2sc3cc(OC)ccc3c2C(=O)c2ccc(OCOC(C)=O)cc2)cc1 | null | null | [Al+3] | [Cl-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCS | null | null | null | null | null | null | null | null | null | null | null | null | [6-Methoxy-2-(4-methoxyphenyl)benzo[b]thiophen-3-yl][4-(Acetoxymethoxy)phenyl]methanone (1.7 g, 2.5 mmol) was converted to the title compound by the procedure of Example 3 using 500 mg (7.5 mmol) of ethanethiol and 1.0 g (7.5 mmol) of aluminum chloride except that the total reaction time was 4 hours. | CC(=O)OCOc1ccc(C(=O)c2c(-c3ccc(O)cc3)sc3cc(O)ccc23)cc1 | null | 29 | null |
857,571 | ord_dataset-faa0236be76c4501841c954527cd1b6c | null | 2008-01-01T00:12:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:12]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=2)[OH:13])[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10]>C(Cl)Cl.O=[Mn]=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[... | COc1cc(C(O)c2cc(OC)c(OC)c(OC)c2)ccc1[N+](=O)[O-] | null | null | O=[Mn]=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 | 25 | 48 | A suspension of (3-methoxy-4-nitro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanol (2.1 g, 6.1 mmol) and MnO2 (6.0 g, 69 mmol) in CH2Cl2 (100 mL) was stirred at room temperature for 2 days. The mixture was filtered through Celite and the filtrate was concentrated. The crude product was purified by flash chromatography (sili... | COc1cc(C(=O)c2cc(OC)c(OC)c(OC)c2)ccc1[N+](=O)[O-] | null | 47.2 | null |
1,244,021 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | [CH3:1][N:2]1[CH2:6][CH2:5][CH:4]([NH2:7])[CH2:3]1.C(N(CC)C(C)C)(C)C.Cl[S:18]([C:21]1[CH:22]=[C:23]([C:27]2[C:36]([CH3:38])([CH3:37])[CH2:35][C:34]3[C:29](=[CH:30][CH:31]=[C:32]([C:39]([O:41][CH3:42])=[O:40])[CH:33]=3)[N:28]=2)[CH:24]=[CH:25][CH:26]=1)(=[O:20])=[O:19]>ClCCl>[CH3:37][C:36]1([CH3:38])[CH2:35][C:34]2[C:29... | COC(=O)c1ccc2c(c1)CC(C)(C)C(c1cccc(S(=O)(=O)Cl)c1)=N2 | CN1CCC(N)C1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | 25 | 3 | To a stirred solution of 1-methylpyrrolidin-3-amine (52 mg, 0.52 mmol) and N,N-diisopropylethylamine (112 mg, 0.86 mmol) in dichloromethane (4 mL) was added methyl 2-(3-(chlorosulfonyl)phenyl)-3,3-dimethyl-3,4-dihydroquinoline-6-carboxylate (170 mg, 0.43 mmol) portionwise. The resultant yellow solution was stirred for ... | COC(=O)c1ccc2c(c1)CC(C)(C)C(c1cccc(S(=O)(=O)NC3CCN(C)C3)c1)=N2 | null | 77.6 | null |
1,361,296 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | [F:1][C:2]([C:5]1[O:9][C:8]([CH2:10][N:11]2[N:15]=[C:14]([NH2:16])[CH:13]=[N:12]2)=[CH:7][CH:6]=1)([F:4])[CH3:3].[C:17]1([C:23]2[O:27][CH:26]=[N:25][C:24]=2[C:28](O)=[O:29])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[F:4][C:2]([C:5]1[O:9][C:8]([CH2:10][N:11]2[N:15]=[C:14]([NH:16][C:28]([C:24]3[N:25]=[CH:26][O:27][C:23]=3... | CC(F)(F)c1ccc(Cn2ncc(N)n2)o1 | O=C(O)c1ncoc1-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 general procedure Z2, starting from 2-[5-(1,1-difluoro-ethyl)-furan-2-ylmethyl]-2H-[1,2,3]triazol-4-ylamine and 5-phenyl-oxazole-4-carboxylic acid. | CC(F)(F)c1ccc(Cn2ncc(NC(=O)c3ncoc3-c3ccccc3)n2)o1 | null | null | null |
528,330 | ord_dataset-f027aa93238e424fbbf9bad1c7699adc | null | 2001-01-01T00:12:00 | true | [NH2:1][C:2]1[N:10]=[C:9]([SH:11])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([OH:19])[N:6]2[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:26]([O:33][CH2:34]Cl)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C)C=O>[NH2:1][C:2]1[N:10]=[C:9]([S:11][CH2:34][O:33][CH2:26][C:27]2[CH:32]=[CH:31][C... | ClCOCc1ccccc1 | Nc1nc(S)nc2c1nc(O)n2Cc1ccccc1 | null | O=C([O-])[O-] | [K+] | 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 | 4 | Crude 6-amino-9-benzyl-8-hydroxy-2-mercaptopurine (134 mg, 0.49 mmol) was suspended in dimethylformamide (60 ml). To the suspension were added potassium carbonate (100 mg, 0.72 mmol) and benzyloxymethyl chloride (0.1 ml, 0.7 mmol) in order. The mixture was stirred at room temperature for 4 hours. The solvent was remove... | Nc1nc(SCOCc2ccccc2)nc2c1nc(O)n2Cc1ccccc1 | null | 46.7 | null |
890,383 | ord_dataset-11068b1e475b4c5b82e56726ab0dddb7 | null | 2009-01-01T00:07:00 | true | [CH3:1][O:2][C:3](=[O:27])[CH:4]([C:9]1[CH:10]=[C:11]([C:16]2[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([F:26])[CH:17]=2)[CH:12]=[C:13]([OH:15])[CH:14]=1)[CH2:5][CH:6]([CH3:8])[CH3:7].[F:28][C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[C:33]([F:35])[CH:34]=1>>[CH3:1][O:2][C:3](=[O:27])[CH:4]([C:9]1[CH:10]=[C:11]... | COC(=O)C(CC(C)C)c1cc(O)cc(-c2cc(F)cc(C(F)(F)F)c2)c1 | OB(O)c1cc(F)cc(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 in 83% yield from 2-(3′-fluoro-5-hydroxy-5′-trifluoromethyl-biphenyl-3-yl)-4-methyl-pentanoic acid methyl ester (prepared in Example B) and 3,5-difluorobenzene boronic acid under the conditions described in Example 15, step (g). | COC(=O)C(CC(C)C)c1cc(Oc2cc(F)cc(F)c2)cc(-c2cc(F)cc(C(F)(F)F)c2)c1 | null | 83 | null |
1,542,521 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | [OH:1][CH2:2][CH2:3][SH:4].[NH2:5][C:6]1[CH:11]=[N:10][C:9](Br)=[CH:8][N:7]=1>CN(C)C=O.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:5][C:6]1[N:7]=[CH:8][C:9]([S:4][CH2:3][CH2:2][OH:1])=[N... | OCCS | Nc1cnc(Br)cn1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 120 | 3 | According to the method described in WO2004/052869, 2-hydroxy-1-ethanethiol (0.93 mL) and tetrakis(triphenylphosphine)palladium (3.39 g) were added to a solution of 2-amino-5-bromopyrazine (1.00 g, 5.75 mmol) in N,N-dimethylformamide (15.1 mL), and the mixture was heated and stirred at 120° C. in a sealed tube for abou... | Nc1cnc(SCCO)cn1 | null | null | null |
684,811 | ord_dataset-359b8fc87f4244be89d6f02bc5036eac | null | 2005-01-01T00:09:00 | true | [F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][S:10][C:11]1[N:16]=[C:15]([NH2:17])[C:14]([NH2:18])=[C:13]([NH2:19])[N:12]=1.[C:20](OCC)(=O)[CH:21]=[O:22].O.Cl>[Na].CO>[NH2:17][C:15]1[C:14]2[N:18]=[CH:20][C:21](=[O:22])[NH:19][C:13]=2[N:12]=[C:11]([S:10][CH2:9][C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=2[F:1... | Nc1nc(SCc2cccc(F)c2F)nc(N)c1N | CCOC(=O)C=O | null | Cl | [Na] | 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 | 0.25 | The product of example 2, step (c) (100 mg) was dissolved in a solution of sodium (0.05 g) in methanol (5 ml). This was left to stir for 15 min at room temperature, then ethyl glyoxalate (134 μl) was added to the mixture which was left to stir for 12 hr at room temperature. Water (5 ml) was added, then concentrated hyd... | Nc1nc(SCc2cccc(F)c2F)nc2[nH]c(=O)cnc12 | null | null | null |
1,582,960 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | [NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[CH:10]=2)[C:6]=1[C:7]#[N:8].[C:16]([O:22][CH2:23][CH3:24])(=[O:21])[CH2:17][C:18]([CH3:20])=O.Cl[Sn](Cl)(Cl)Cl>C1(C)C=CC=CC=1>[NH2:8][C:7]1[C:17]([C:16]([O:22][CH2:23][CH3:24])=[O:21])=[C:18]([CH3:20])[N:1]=[C:2]2[S:3][CH:4]=[C:5]([C:9]3[CH:14... | Cc1cccc(-c2csc(N)c2C#N)c1 | CCOC(=O)CC(C)=O | null | Cl[Sn](Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | 25 | null | To a stirred solution of 2-amino-4-(3-methylphenyl)-3-thiophenecarbonitrile (Description 56) (2.98 g, 13.91 mmol) in toluene (75 mL) at RT was added ethyl acetoacetate (1.76 mL, 13.91 mmol) and SnCl4 (3.26 mL, 27.8 mmol). The reaction mixture was refluxed under a nitrogen atmosphere for ca. 4 h and was then cooled to R... | CCOC(=O)c1c(C)nc2scc(-c3cccc(C)c3)c2c1N | null | 19.4 | null |
214,126 | ord_dataset-b67d30cd146f49dcbf24faee022f1a09 | null | 1990-01-01T00:08:00 | true | [Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13](=O)[CH3:14])=[CH:8][CH:7]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:22].[Na+]>CO>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH:13]([NH2:22])[CH3:14])=[CH:8][CH:7]=1 | CC(=O)Cc1ccc(OCCCCl)cc1 | [BH3-]C#N | null | CC(=O)[O-] | [NH4+] | [Na+] | 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 | 5 | A 1.36 g sample of 4-(3-chloropropoxy)phenylacetone, prepared above, was dissolved in 200 mL of methanol. To this was added 7.71 g of ammonium acetate followed by 0.76 g sodium cyanoborohydride with stirring. After 5 hours, the solvent was evaporated in vacuo, the residue was dissolved in 150 mL diethylether and 200 ml... | CC(N)Cc1ccc(OCCCCl)cc1 | null | null | null |
1,226,646 | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | null | 2012-01-01T00:11:00 | true | [Cl:1][C:2]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14](=[O:17])[N:13]([CH2:18][CH2:19][O:20][C:21]3[C:30]4[C:25](=[CH:26][C:27]([O:31][CH3:32])=[CH:28][CH:29]=4)[N:24]=[CH:23][CH:22]=3)[N:12]=2)[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=O.N1C=CC=CC=1.S(Cl)(Cl)=O>>[Cl:1][C:2]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14](=[O:17])[... | COc1ccc2c(OCCn3nc(-c4ccc(C(N)=O)c(Cl)c4)ccc3=O)ccnc2c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=S(Cl)Cl | c1ccncc1 | null | null | null | null | null | null | null | null | null | 23 | 18 | See example 75 for a general synthesis. To a solution of 2-chloro-4-(1-(2-(7-methoxyquinolin-4-yloxy)ethyl)-6-oxo-1,6-dihydropyridazin-3-yl)benzamide (120 mg, 266 μmol) in pyridine (10763 μL, 133075 μmol) was added thionyl chloride (194 μL, 2661 μmol). The reaction was then stirred overnight at 23° C. for 18 hours. The... | COc1ccc2c(OCCn3nc(-c4ccc(C#N)c(Cl)c4)ccc3=O)ccnc2c1 | null | null | null |
1,086,834 | ord_dataset-52a37d876ddb453e86de0c15fa233d29 | null | 2011-01-01T00:09:00 | true | C(N(CC)CC)C.Cl.[CH3:9][O:10][C:11](=[O:24])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][NH2:19])[C:13]=1[C:20]([O:22][CH3:23])=[O:21].[C:25](Cl)(=[O:27])[CH3:26]>ClCCl>[CH3:9][O:10][C:11](=[O:24])[C:12]1[C:13](=[C:14]([CH2:18][NH:19][C:25](=[O:27])[CH3:26])[CH:15]=[CH:16][CH:17]=1)[C:20]([O:22][CH3:23])=[O:21] | CC(=O)Cl | COC(=O)c1cccc(CN)c1C(=O)OC | 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 | 4 | null | Triethylamine (1.87 g, 18 mmol) was added slowly to a stirred suspension of methyl-3-(aminomethyl)-2-(methoxycarbonyl)benzoate hydrochloride (2.0 g, 8 mmol) in dichloromethane (30 ml). The resulting mixture was cooled in an ice bath to 4° C. Acetyl chloride (0.73 g, 9 mmol) was added dropwise at a rate such that the te... | COC(=O)c1cccc(CNC(C)=O)c1C(=O)OC | null | 77.8 | null |
285,273 | ord_dataset-d63ab258f4634f87bdebbaff0a341c28 | null | 1994-01-01T00:02:00 | true | [N+]([O-])(O)=[O:2].[CH3:5][C:6]1([CH3:15])[CH2:11][CH2:10][CH2:9][C@@H:8]([CH3:12])[C@@H:7]1[CH:13]=[O:14]>>[CH3:15][C:6]1([CH3:5])[CH2:11][CH2:10][CH2:9][C@@H:8]([CH3:12])[C@@H:7]1[C:13]([OH:2])=[O:14] | C[C@@H]1CCCC(C)(C)[C@H]1C=O | O=[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 | 55 | 2 | In a 300-ml 4-necked flask equipped with a condenser, a thermometer, a dropping funnel, and a stirrer was placed 38 g of nitric acid (aqueous 60% solution) and heated to 55° C. Then, 90 g of (1S,6R)-2,2,6-trimethylcyclohexanecarbaldehyde (14) [composition: 91% of the (1S,6R)-form, 9% of the (1R,6R)-form] synthesized in... | C[C@@H]1CCCC(C)(C)[C@H]1C(=O)O | null | 98.7 | null |
907,571 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | [CH3:1][NH:2][CH3:3].[Cl:4][C:5]1[CH:13]=[CH:12][C:8]([C:9](O)=[O:10])=[CH:7][N:6]=1>>[Cl:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([N:2]([CH3:3])[CH3:1])=[O:10])=[CH:7][N:6]=1 | CNC | O=C(O)c1ccc(Cl)nc1 | null | null | null | null | null | null | null | 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 (D36) was prepared from dimethylamine and 6-chloronicotinic acid according to the procedure described for Description 35. MS electrospray (+ve ion) 185 (MH+). | CN(C)C(=O)c1ccc(Cl)nc1 | null | null | null |
1,514,733 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | [CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]1([C:15]2[NH:19][N:18]=[C:17]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:16]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH2:1]([N:19]1[C:15]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:16][C:17]([C:20]([O:22][CH2:23][CH3... | BrCc1ccccc1 | CCOC(=O)c1cc(-c2ccccc2)[nH]n1 | null | O=C([O-])[O-] | [K+] | 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 | null | Benzyl bromide (696 mg, 4.01 mmol) was added to ethyl 5-phenyl-1H-pyrazole-3-carboxylate (880 mg, 4.1 mmol) and potassium carbonate (562 mg, 4.01) in DMF (8 mL). The reaction was stirred for several h and then diluted with water. The mixture was washed several times with ethyl acetate and the combine extracts were drie... | CCOC(=O)c1cc(-c2ccccc2)n(Cc2ccccc2)n1 | null | 105.8 | null |
362,280 | ord_dataset-0b24d1f58a024ed7bc2bda95b2430c72 | null | 1997-01-01T00:04:00 | true | C([NH:4][C:5]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[C:7]([C:15]([F:18])([F:17])[F:16])[C:6]=1[N+:19]([O-:21])=[O:20])(=O)C>Cl.CCO>[N+:19]([C:6]1[C:7]([C:15]([F:16])([F:17])[F:18])=[CH:8][C:9]([C:11]([F:12])([F:13])[F:14])=[CH:10][C:5]=1[NH2:4])([O-:21])=[O:20] | CC(=O)Nc1cc(C(F)(F)F)cc(C(F)(F)F)c1[N+](=O)[O-] | 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 | null | null | A mixture of 1-acetamido-2-nitro-3,5-bis(trifluoromethyl)benzene (200 mg, 0.63 mmol) in concentrated HCl (3 mL) and EtOH (3 mL) was refluxed overnight, then it was extracted by ethyl acetate (2×3 mL). The extract was dried over Mg2SO4 and evaporated to give 2-nitro-3,5-bis(trifluoromethyl)aniline 123 mg (71%). 1H NMR (... | Nc1cc(C(F)(F)F)cc(C(F)(F)F)c1[N+](=O)[O-] | null | 71.2 | null |
1,673,857 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=O)[CH:8]([NH:14][C:15]([C:17]1[O:21][N:20]=[C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:18]=1[C:28]([F:31])([F:30])[F:29])=O)[CH2:7][CH2:6]2.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:41])=CC=1>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:1... | COc1ccc2c(c1)CCC(NC(=O)c1onc(-c3ccccc3)c1C(F)(F)F)C2=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 | 140 | null | A mixture of N-(6-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)-3-phenyl-4-(trifluoromethyl)isoxazole-5-carboxamide (Preparation 56A, 337 mg, 0.783 mmol) and Lawesson's reagent (2,4-Bis-[4-methoxyphenyl]-1,3-dithia-2,4-diphosphetane 2,4-disulfide) (475 mg, 1.175 mmol) in THF (4.0 ml) was heated for 33 min at 140° C.... | COc1ccc2c(c1)CCc1nc(-c3onc(-c4ccccc4)c3C(F)(F)F)sc1-2 | null | 108.8 | null |
1,393,148 | ord_dataset-12dc3bd21bcf44d09e5b4249afe15161 | null | 2014-01-01T00:02:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]([NH:16]C(=O)OCC2C=CC=CC=2)[CH3:15])[CH:6]=[CH:7][C:8]=1[NH:9][S:10]([CH3:13])(=[O:12])=[O:11].C(N)C>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]([NH2:16])[CH3:15])[CH:6]=[CH:7][C:8]=1[NH:9][S:10]([CH3:13])(=[O:12])=[O:11] | COc1cc(C(C)NC(=O)OCc2ccccc2)ccc1NS(C)(=O)=O | null | null | CCN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Through similar procedure to that in Example 1-2 excepting using Benzyl N-{1-[3-methoxy-4-(methylsulfonylamino)phenyl]ethyl}carbamate (14-1) as a starting material, □1□3-Methoxy-4-(methylsulfonylamino)phenyl]ethyl amine (14-3, CHK-570) having following physicochemical properties was synthesized: | COc1cc(C(C)N)ccc1NS(C)(=O)=O | null | null | null |
225,796 | ord_dataset-67612e25ea9d4b29966a776893a43d59 | null | 1991-01-01T00:04:00 | true | [NH2:1][CH:2]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[F:15])[C:6]2[CH:16]=[CH:17][CH:18]=[CH:19][C:5]=2[NH:4][C:3]1=[O:20].[C:21](Cl)(=[O:30])[CH:22]=[CH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(CC)CC)C>C(Cl)Cl>[C:21]([NH:1][CH:2]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[F:... | O=C(Cl)C=Cc1ccccc1 | NC1N=C(c2ccccc2F)c2ccccc2NC1=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 | null | 16 | 3-(RS)-Amino-1,3-dihydro-5-(2'-fluorophenyl)-2H-1,4-benzodiazepin-2-one (50 mg, 0.186 mmol) was suspended in methylene chloride (1 ml). Cinnamoyl chloride (34.5 mg, 0.207 mol) was added to the methylene chloride mixture. The pH of the stirred mixture was adjusted to ~9 with 50 μl of triethylamine. After stirring for 16... | O=C(C=Cc1ccccc1)NC1N=C(c2ccccc2F)c2ccccc2NC1=O | null | null | null |
1,310,455 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | C(N(CC)CC)C.[NH2:8][C:9]1[C:18]2[N:19]=[C:20]([CH2:31][O:32][CH2:33][CH3:34])[N:21]([CH2:22][C:23]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])([CH3:25])[CH3:24])[C:17]=2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1.Cl[C:36]([O:38][CH2:39][CH2:40][CH3:41])=[O:37]>ClCCl>[CH2:33]([O:32][CH2:31][C:20]1[N:21]([CH2:22][... | CCOCc1nc2c(N)nc3ccccc3c2n1CC(C)(C)NS(C)(=O)=O | CCCOC(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 0 | 24 | Triethylamine (2.67 mL, 5 eq) was added to a chilled (ice/water bath) suspension of N-{2-[4-amino-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}methanesulfonamide (1.5 g, 1 eq) in dichloromethane (150 mL). A solution of propyl chloroformate (1.55 g, 3.3 eq) in dichloromethane (5 mL) was added dropwis... | CCCOC(=O)Nc1nc2ccccc2c2c1nc(COCC)n2CC(C)(C)NS(C)(=O)=O | null | 67.2 | null |
1,709,415 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | [CH3:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:18][CH2:19][OH:20]>CN(C=O)C.CCOC(C)=O>[CH3:1][C:2]1[N:6]([CH2:18][CH2:19][OH:20])[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1 | Cc1nc2ccccc2[nH]1 | OCCBr | null | O=C([O-])[O-] | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 150 | 1 | To a solution of 2-methyl-1H-benzimidazole (3.50 g, 25.95 mmol) in DMF (70.0 mL), Cs2CO3 (12.08 g, 36.33 mmol) and 2-bromoethanol (2.5 mL, 34.15 mmol) was added. After stirring at 150° C. for 1 h, the reaction mixture was allowed to reach rt and was diluted with EtOAc. The org. layer was separated and the aq. layer was... | Cc1nc2ccccc2n1CCO | null | null | null |
102,932 | ord_dataset-bdb961f26fac426eaa2de8f54a284acf | null | 1983-01-01T00:02:00 | true | [OH:1][N:2]=[C:3]([C:9](=[O:11])[CH3:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].[Cl:12][C:13]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:14]=1[CH2:15]Cl.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(OCC)(=O)C>[Cl:12][C:13]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:14]=1[CH2:15][O:1][N:2]=[C:3]([C:9](=[O:11])[CH3:10])[C:4]([O:6][CH2:7][C... | CCOC(=O)C(=NO)C(C)=O | ClCc1ccc(Cl)cc1Cl | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | Ethyl 2-hydroxyimino-3-oxobutyrate (syn isomer, 17.0 g.), 2,4-dichlorobenzyl chloride (25 g.), potassium carbonate (22.0 g.), N,N-dimethylformamide (25 ml.) and ethyl acetate (25 ml.) were treated in a similar manner to that of Example A-(1) to give ethyl 2-(2,4-dichlorobenzyloxyimino)-3-oxobutyrate (syn isomer, 33.7 g... | CCOC(=O)C(=NOCc1ccc(Cl)cc1Cl)C(C)=O | null | 99.2 | null |
1,182,019 | ord_dataset-9cd817a75dfc4fe7ad19d4232772d5ff | null | 2012-01-01T00:07:00 | true | [CH3:1][C:2]12[CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:3]1[NH:4][CH2:5][CH2:6][CH2:7]2.[C:15](O)(=O)[CH3:16].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCCl>[CH2:15]([N:4]1[CH2:5][CH2:6][CH2:7][C:2]2([CH3:1])[CH2:14][C:13]3[C:8]([CH:3]12)=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH3:16] | CC(=O)O | CC12CCCNC1c1ccccc1C2 | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O | [Na+] | [OH-] | 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 | 70 | 3 | To a solution of (4aRS,9bRS)-4a-methyl-2,3,4,4a,5,9b-hexahydro-1H-indeno[1,2-b]pyridine (140 mg) in 1,2-dichloroethane (3 ml) were added acetic acid (0.214 ml) and sodium triacetoxyborohydride (1.1 g), followed by heating and stirring at 70° C. for 3 hours. The reaction solution was basified by adding a 1 M aqueous sod... | CCN1CCCC2(C)Cc3ccccc3C12 | null | null | null |
459,136 | ord_dataset-aa5bc55d09b7465ab353e144a7ac3ad1 | null | 2000-01-01T00:03:00 | true | C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9]1[S:13][C:12](=[O:14])[NH:11][N:10]=1.Cl[CH2:16][C:17](=[O:19])[CH3:18]>O1CCOCC1>[CH3:7][O:8][C:9]1[S:13][C:12](=[O:14])[N:11]([CH2:16][C:17](=[O:19])[CH3:18])[N:10]=1 | CC(=O)CCl | COc1n[nH]c(=O)s1 | null | O=C([O-])[O-] | [K+] | 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 | 20 | 69 g of potassium carbonate are added to a solution of 33 g of 5-methoxy-3H-[1,3,4]thiadiazol-2-one in 400 ml of dioxane and the reaction mixture is heated to 60°. Then 21 g of chloroacetone are added dropwise within a short period of time and the reaction mixture is stirred at 70° for 20 hours and then, at 20°, is fil... | COc1nn(CC(C)=O)c(=O)s1 | null | null | null |
407,819 | ord_dataset-d5bb2294ac964841b8ffc9e0a34e93af | null | 1998-01-01T00:07:00 | true | Cl.C[O:3][C:4](=[O:29])[C@H:5]([CH2:19][C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[NH:22][CH:21]=1)[NH:6][C:7](=[O:18])[C@@H:8]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[NH:9][CH3:10].[C:30]1([CH3:39])[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([OH:38])=O)[CH:31]=1>>[CH3:39][C:30]1[CH:31]=[C:32]([CH:3... | CN[C@H](Cc1ccccc1)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)OC | Cc1cccc(C(=O)O)c1 | 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 | Coupling of N-methyl-(D)-phenylalanyl-(L)-tryptophan methyl ester hydrochloride (see example 1) with m-toluic acid according to example 12 followed by hydrolysis of the methyl ester moiety according to example 1 gives N-(3-methylbenzoyl)-N-methyl-(D)-phenylalanyl-(L)-tryptophan; FAB-MS m/e 484 (M+H)+. | Cc1cccc(C(=O)N(C)[C@H](Cc2ccccc2)C(=O)N[C@@H](Cc2c[nH]c3ccccc23)C(=O)O)c1 | null | null | null |
1,638,137 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | [CH3:1][N:2]1[CH:6]=[C:5]([CH:7]=[O:8])[C:4]([CH:9]([F:11])[F:10])=[N:3]1.S(Cl)([Cl:15])(=O)=O>ClC1C=CC=CC=1>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]([Cl:15])=[O:8])[C:4]([CH:9]([F:10])[F:11])=[N:3]1 | O=S(=O)(Cl)Cl | Cn1cc(C=O)c(C(F)F)n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Clc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | The solution of 16 g (100 mol) of 1-methyl-3-difluoromethyl-1H-pyrazole-4-carbaldehyde, 13.5 g (100 mmol) of sulphuryl chloride and 0.2 g of 2,2-azoisobutyronitrile in 50 ml of chlorobenzene was stirred at 70-80° C. for 6 h. The reaction solution was concentrated. 18.8 g of the product (95% yield) was obtained as an oi... | Cn1cc(C(=O)Cl)c(C(F)F)n1 | null | 96.6 | null |
1,243,131 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[O:11][CH3:12].[F:13][C:14]([F:19])([F:18])C([O-])=O.[K+].C1(C)C=CC=CC=1>CN(C)C=O>[CH3:12][O:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[C:14]([F:19])([F:18])[F:13] | COc1cc([N+](=O)[O-])ccc1Br | O=C([O-])C(F)(F)F | null | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | 155 | 20 | To a solution of 1-bromo-2-methoxy-4-nitrobenzene (10.0 g, 43.0 mmol) in N,N-dimethylformamide (200 mL) were added potassium trifluoroacetate (13.0 g, 86.0 mmol), copper iodide(I) and toluene (40 mL), and the mixture was stirred at 155° C. for 20 hr while removing the produced water drops by a Dean-Stark trap. The reac... | COc1cc([N+](=O)[O-])ccc1C(F)(F)F | null | 72.1 | null |
32,397 | ord_dataset-8f61d01cf5b34e85a3ccc89f8901797b | null | 1977-01-01T00:11:00 | true | [C:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=O)(=O)[CH3:2].[CH2:13]([NH2:17])[CH2:14][CH2:15][NH2:16]>>[CH3:2][C:1]12[NH:17][CH2:13][CH2:14][CH2:15][N:16]1[C:6](=[O:8])[C:5]1[C:4]2=[CH:12][CH:11]=[CH:10][CH:9]=1 | CC(=O)c1ccccc1C(=O)O | NCCCN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 16.4 Parts of o-acetyl-benzoic acid and 8 parts of 1,3-propanediamine are heated for 2 hours at 150°-160°. The reaction mixture is then distilled under high vacuum. The 10b-methyl-1,3,4,10b-tetrahydro-pyrimido[2,1-a]isoindol -6(2H)-one obtained of the formula ##STR35## boils at 120°-123°/0.1 Torr. After recrystallising... | CC12NCCCN1C(=O)c1ccccc12 | null | null | null |
251,240 | ord_dataset-41ea179beba54bed8cd874a5ec3469f7 | null | 1992-01-01T00:07:00 | true | O.[C:2]1([CH3:11])[CH:7]=[CH:6][C:5]([S:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[Na+].Br[CH2:14][CH2:15][CH:16]1[O:20][CH2:19][CH2:18][O:17]1.N>CN(C=O)C>[CH2:19]1[O:20][CH:16]([CH2:15][CH2:14][S:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:11])=[CH:3][CH:4]=2)(=[O:10])=[O:9])[O:17][CH2:18]1 | BrCCC1OCCO1 | Cc1ccc(S(=O)[O-])cc1 | null | N | [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 | 0 | null | A mixture of sodium 4-toluenesulphinate monohydrate (37.2 g, 0.19 mole) and 2-(2-bromoethyl)-1,3-dioxolane (20 ml, 0.17 mole) in dry DMF (100 ml) was stirred at room temperature for 64h, resulting in a homogenous solution. This was poured into ice/water (1 liter) containing conc. ammonia solution (100 ml) and stirred v... | Cc1ccc(S(=O)(=O)CCC2OCCO2)cc1 | null | 65.9 | null |
436,669 | ord_dataset-a1e9aa99368e4e5da8b1786b1c05521d | null | 1999-01-01T00:08:00 | true | [CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:34])=[C:11]([C:15]4[CH:16]=[C:17]5[C:21](=[CH:22][CH:23]=4)[CH2:20][N:19](S(C4C=CC(C)=CC=4)(=O)=O)[CH2:18]5)[C:12]=3[CH3:14])[C:7](=[O:35])[C:6]([C:36]([OH:38])=[O:37])=[CH:5]2)[CH2:3][CH2:2]1.C1(O)C=CC=CC=1.C(O)(=O)CC.[BrH:51]>>[BrH:51].[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:1... | Cc1ccc(S(=O)(=O)N2Cc3ccc(-c4c(F)cc5c(=O)c(C(=O)O)cn(C6CC6)c5c4C)cc3C2)cc1 | null | null | Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCC(=O)O | Oc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | In 5.3 ml of 47% hydrobromic acid was suspended 0.53 g of 1-cyclopropyl-6-fluoro-8-methyl-7-[2-(p-toluenesulfonyl)isoindolin-5-yl]-1,4-dihydro-4-oxoquinoline-3 carboxylic acid, and 0.28 g of phenol and 3.2 ml of propionic acid were added to the suspension, after which the resulting mixture was heated under reflux for o... | Cc1c(-c2ccc3c(c2)CNC3)c(F)cc2c(=O)c(C(=O)O)cn(C3CC3)c12 | null | null | null |
959,083 | ord_dataset-ed65749688da45af8a8432967b017729 | null | 2010-01-01T00:05:00 | true | [CH:1]1([C:6]2[CH:7]=[C:8]3[C:13](=[CH:14][CH:15]=2)[C:12](=[O:16])[NH:11][C:10](=[O:17])[CH2:9]3)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:18][O:19][CH:20](OC)OC>C(O)(=O)C>[CH:1]1([C:6]2[CH:7]=[C:8]3[C:13](=[CH:14][CH:15]=2)[C:12](=[O:16])[NH:11][C:10](=[O:17])[C:9]3=[CH:18][O:19][CH3:20])[CH2:2][CH2:3][CH2:4][CH2:5]1 | O=C1Cc2cc(C3CCCC3)ccc2C(=O)N1 | COC(OC)OC | 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 | 90 | null | A mixture of 6-cyclopentyl-4H-isoquinoline-1,3-dione (222 mg, 0.97 mmole), 10 mL of acetic acid and trimethylorthoformate (212 mg, 2.0 mmole) is stirred and heated to 90° C. After 2 hours at that temperature the reaction mixture is cooled and the solvents were removed in-vacuo and the residue taken up in 4% methanol in... | COC=C1C(=O)NC(=O)c2ccc(C3CCCC3)cc21 | null | null | null |
1,600,877 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [F:1][C:2]([F:14])([F:13])[C:3]1[CH:12]=[CH:11][C:10]2[CH:8]3[O:9][CH:7]3[CH2:6][C:5]=2[CH:4]=1.[CH3:15][C@@H:16]1[NH:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]1>C(O)C>[OH:9][CH:7]1[CH2:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([C:2]([F:14])([F:13])[F:1])[CH:4]=2)[CH:8]1[N:21]... | C[C@H]1CN(C(=O)OC(C)(C)C)CCN1 | FC(F)(F)c1ccc2c(c1)CC1OC21 | null | null | 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 | 95 | null | A mixture of 4-(trifluoromethyl)-6,6a-dihydro-1aH-indeno[1,2-b]oxirene (1.2 g, 6.0 mmol) and tert-butyl (3S)-3-methylpiperazine-1-carboxylate (1.4 g, 7.2 mol) in ethanol (20 mL) was refluxed overnight. Another gram of tert-butyl (3S)-3-methylpiperazine-1-carboxylate was added. The mixture was transferred into a sealed ... | C[C@H]1CN(C(=O)OC(C)(C)C)CCN1C1c2ccc(C(F)(F)F)cc2CC1O | null | null | null |
1,334,917 | ord_dataset-08852243bba44cb28769a5833f1515fe | null | 2013-01-01T00:09:00 | true | CC1C=CC(S(O[CH2:12][C@H:13]2[O:18][C:17]3[CH:19]=[C:20]([S:23]([CH3:26])(=[O:25])=[O:24])[CH:21]=[CH:22][C:16]=3[O:15][CH2:14]2)(=O)=O)=CC=1.[CH3:27][CH:28]([CH3:31])[CH2:29][NH2:30]>C(#N)C>[CH3:27][CH:28]([CH3:31])[CH2:29][NH:30][CH2:12][C@H:13]1[O:18][C:17]2[CH:19]=[C:20]([S:23]([CH3:26])(=[O:24])=[O:25])[CH:21]=[CH:... | Cc1ccc(S(=O)(=O)OC[C@@H]2COc3ccc(S(C)(=O)=O)cc3O2)cc1 | CC(C)CN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | 120 | null | A mixture of [(2S)-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate (0.2 g, 0.5 mmol), 2-methylpropane-1-amine (1 ml) and ACN (2 ml) was heated under microwave radiation at 120° C. for 30 min. Purification on SCX-3 column (TEA/MeOH) and flash column chromatography (EtOAc/MeOH). Yield:... | CC(C)CNC[C@@H]1COc2ccc(S(C)(=O)=O)cc2O1 | null | null | null |
159,306 | ord_dataset-41c90677d90b4fa5836ab66e2f5b4f51 | null | 1987-01-01T00:06:00 | true | [CH2:1]([O:3][C:4](=[O:12])[C:5]1[C:6](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH2:7])[CH3:2].[C:13](O)(=O)[C:14]1C(=CC=C[CH:20]=1)N>>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[C:6](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:7][CH:14]([CH3:20])[CH3:13])[CH3:2] | CCOC(=O)c1ccccc1N | Nc1ccccc1C(=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 | Following the reaction procedure of Example 8 but substituted a molar equivalent amount of anthranilic acid ethyl ester for the anthranilic acid, there is obtained N-isopropylanthranilic acid ethyl ester. | CCOC(=O)c1ccccc1NC(C)C | null | null | null |
58,294 | ord_dataset-cb9f452f8418479ab5fd99c835dbe015 | null | 1979-01-01T00:09:00 | true | [CH:1]([NH:4][C:5]1[C:18]2[C:17](=[O:19])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[OH:20])[C:10](=[O:21])[C:9]=2[C:8](Br)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].[CH:23]1([NH2:29])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.C([O-])(=O)C.[K+].[Cl-]>CO>[CH:1]([NH:4][C:5]1[C:18]2[C:17](=[O:19])[C:16]3[C:11](=[CH:12][CH:13]=[CH:... | CC(C)Nc1ccc(Br)c2c1C(=O)c1c(O)cccc1C2=O | NC1CCCCC1 | null | CC(=O)[O-] | [Cl-] | [K+] | 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 | 18 g of 1-isopropylamino-4-bromo-8-hydroxy-anthraquinone, 36 ml of cyclohexylamine, 6.5 of potassium acetate and catalytic amounts of copperI chloride are stirred at 80°-90° until only a little starting material is still detectable. The mixture is now diluted with 36 ml of methanol and the reaction product which has se... | CC(C)Nc1ccc(NC2CCCCC2)c2c1C(=O)c1c(O)cccc1C2=O | null | null | null |
395,866 | ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | null | 1998-01-01T00:03:00 | true | [NH2:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.[NH2:11][C:12]1[N:17]=[C:16](Cl)[CH:15]=[C:14]([CH3:19])[N:13]=1.Cl.[OH-].[K+]>O>[C:8]([C:4]1[CH:3]=[C:2]([NH:1][C:16]2[CH:15]=[C:14]([CH3:19])[N:13]=[C:12]([NH2:11])[N:17]=2)[CH:7]=[CH:6][CH:5]=1)(=[O:10])[CH3:9] | CC(=O)c1cccc(N)c1 | Cc1cc(Cl)nc(N)n1 | null | Cl | [K+] | [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 | Compound No. 15: A suspension of m-aminoacetophenone (2.7 g) and 2-amino-4-chloro-6-methylpyrimidine (2.87 g) in 40 mL water was treated with 1.7 mL concentrated HCl and heated at reflux for 1 hour. Addition of 40 mL 1N KOH gave a light buff solid, which was filtered out and dried to give 3.8 g 4-(3-acetylphenyl)amino-... | CC(=O)c1cccc(Nc2cc(C)nc(N)n2)c1 | null | 78.5 | null |
947,790 | ord_dataset-3feb2a95f66e4706a4a50c977ccd9bf8 | null | 2010-01-01T00:04:00 | true | ClC(Cl)(Cl)[C:3]([C:5]1[N:14]2[C:8]([CH2:9][N:10]([C:19](=[O:29])[CH2:20][S:21][C:22]3[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=3)[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[CH2:13]2)=[CH:7][CH:6]=1)=[O:4].[F:32][C:33]([F:43])([F:42])[C:34]1[CH:35]=[C:36]([CH:39]=[CH:40][CH:41]=1)[CH2:37][NH2:38]>>[Br:28][C:25]1[... | O=C(CSc1ccc(Br)cc1)N1Cc2ccc(C(=O)C(Cl)(Cl)Cl)n2Cc2ccccc21 | NCc1cccc(C(F)(F)F)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was synthesized in the manner of Example 81 from 2,2,2-trichloro-1-[10-{[(4-bromophenyl)thio]acetyl}-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-yl]-ethanone of Example 80 and 3-trifluoromethylbenzylamine, m.p. 102° C. MS [(+)ESI, m/z]: 614 [M+H]+ Anal. Calcd for C29H23BrF3N3O2S: C, 56.69; H... | O=C(NCc1cccc(C(F)(F)F)c1)c1ccc2n1Cc1ccccc1N(C(=O)CSc1ccc(Br)cc1)C2 | null | null | null |
1,362,972 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | [C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([N:14]3[CH:18]=[C:17]([CH3:19])[N:16]=[CH:15]3)=[CH:11][CH:12]=2)[CH:7]([NH:20][C:21]2[N:26]=[CH:25][C:24]([C:27]([OH:29])=[O:28])=[CH:23][CH:22]=2)[CH2:6][CH:5]1[CH3:30])(=[O:3])[CH3:2].Cl.[CH3:32]O>>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([N:14]3[CH:18]=[C:17]([CH3:19])[N:16]=[CH... | CC(=O)N1c2ccc(-n3cnc(C)c3)cc2C(Nc2ccc(C(=O)O)cn2)CC1C | CO | 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 | 1 | A solution of 6-{[1-acetyl-2-methyl-6-(4-methyl-1H-imidazol-1-yl)-1,2,3,4-tetrahydro-4-quinolinyl]amino}-3-pyridinecarboxylic acid (for a preparation see example 143) (40 mg, 0.099 mmol) in dry methanol (2 mL) was treated at room temperature with HCl (4M in 1,4-dioxane, 200 μl, 0.800 mmol) and the resulting mixture was... | COC(=O)c1ccc(N[C@@H]2C[C@H](C)N(C(C)=O)c3ccc(-n4cnc(C)c4)cc32)nc1 | null | 29 | null |
1,596,780 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [N:1]1[N:2]([C:10]2[N:31]=[CH:30][CH:29]=[CH:28][C:11]=2[C:12]([NH:14][CH:15]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:16]([OH:20])[C:17](O)=[O:18])=[O:13])[CH:3]=[C:4]2[C:9]=1[CH2:8][CH2:7][CH2:6][CH2:5]2.Cl.[CH3:33][O:34][NH2:35]>>[OH:20][CH:16]([C:17]([NH:35][O:34][CH3:33])=[O:18])[CH:15]([NH:14][C... | CON | O=C(NC(Cc1ccccc1)C(O)C(=O)O)c1cccnc1-n1cc2c(n1)CCCC2 | 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 reaction was carried out in analogy to reaction step 3.1 by reacting 3-[2-(4,5,6,7-tetrahydro-2H-indazol-2-yl)nicotinamido]-2-hydroxy-4-phenylbutanoic acid and O-methylhydroxylamine hydrochloride. | CONC(=O)C(O)C(Cc1ccccc1)NC(=O)c1cccnc1-n1cc2c(n1)CCCC2 | null | null | null |
78,883 | ord_dataset-0c37e633e9814a6e886187796cacf216 | null | 1981-01-01T00:03:00 | true | [C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[Na].[CH3:13][C:14]([CH3:18])=[C:15]=[CH:16]Br.O>C(O)C>[CH3:13][C:14]([CH3:18])([C:15]#[CH:16])[CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8] | CCOC(=O)CC(=O)OCC | CC(C)=C=CBr | null | [Na] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | O | null | null | null | null | null | null | null | null | null | null | null | Diethyl malonate (34.8 g.) was added to a solution of sodium (5.0 g.) in ethanol (500 ml.) and the mixture stirred for a few minutes. 3,3-Dimethyl-1-bromoallene (32.0 g.) was then added dropwise at the ambient temperature after which the mixture was refluxed for 3 hours. The ethanolic solution obtained was poured into ... | C#CC(C)(C)C(C(=O)OCC)C(=O)OCC | null | null | null |
975,642 | ord_dataset-f886e51ba1484c76a94bce1482f1eab9 | null | 2010-01-01T00:07:00 | true | [Br:1]N1C(=O)CCC1=O.OS(O)(=O)=O.[O:14]1[C:18]2[CH:19]=[CH:20][C:21]([C:23]3[C:24]4[CH2:38][O:37][C:36](=[O:39])[C:25]=4[CH:26]=[C:27]4[C:35]=3[C:31]3[O:32][CH2:33][O:34][C:30]=3[CH:29]=[CH:28]4)=[CH:22][C:17]=2[O:16][CH2:15]1>C1COCC1.CCOC(C)=O>[O:14]1[C:18]2[CH:19]=[CH:20][C:21]([C:23]3[C:24]4[CH2:38][O:37][C:36](=[O:3... | O=C1OCc2c1cc1ccc3c(c1c2-c1ccc2c(c1)OCO2)OCO3 | O=C1CCC(=O)N1Br | null | O=S(=O)(O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 20 | N-bromosuccinimide (10.7 mg, 0.06 mmol) and concentrated H2SO4 (5 μL) were added to a solution of 2 (15.4 mg, 0.044 mmol) in THF (1 mL). The solution was stirred at room temperature for 20 h, and then diluted with EtOAc (30 μL). The same workup and purification procedure as described for the isolation of 37 gave 38 (12... | O=C1OCc2c1cc1c(Br)cc3c(c1c2-c1ccc2c(c1)OCO2)OCO3 | null | 63.8 | null |
102,083 | ord_dataset-72d9f7ef86df410fac4765c9632d459b | null | 1983-01-01T00:01:00 | true | O=[C:2]1[CH2:7][CH2:6][C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)([C:8]#[N:9])[CH2:4][CH2:3]1.[C:16]1([C:22]2([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CC1C=CC(S(O)(=O)=O)=CC=1.CC1C=CC=CC=1>O>[C:8]([C:5]1([C:10]2[CH:15]=[CH:14][CH:13]... | CCOC(=O)C1(c2ccccc2)CCNCC1 | N#CC1(c2ccccn2)CCC(=O)CC1 | null | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | O | null | null | null | null | null | null | null | null | null | null | null | A mixture of 4.5 parts of 4-oxo-1-(2-pyridinyl)cyclohexanecarbonitrile, 5.2 parts of ethyl 4-phenyl-4-piperidinecarboxylate, 1 part of 4-methylbenzenesulfonic acid and 225 parts of methylbenzene is stirred and refluxed overnight using a water-separator. The reaction mixture is evaporated and the residue is crystallized... | CCOC(=O)C1(c2ccccc2)CCN(C2=CCC(C#N)(c3ccccn3)CC2)CC1 | null | 45 | null |
59,779 | ord_dataset-09e9a37ee5794dc28c0ad7bf7a442c18 | null | 1979-01-01T00:11:00 | true | [C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:8]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH2:9][C:10]([OH:12])=[O:11]>ClCCl>[C:1]1([S:7][O:12][C:10](=[O:11])[CH2:9][NH:8][C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:... | Sc1ccccc1 | O=C(O)CNC(=O)OCc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | null | Using thiophenol and Z-Gly.OH, Example 78 was repeated; except that dichloromethane was used in place of ethyl acetate as the extraction solvent, to obtain N-benzyloxycarbonyl-glycine-phenythio ester (hereinafter represented by ##STR12## in a yield of 62%. | O=C(CNC(=O)OCc1ccccc1)OSc1ccccc1 | null | 62 | null |
965,666 | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | null | 2010-01-01T00:06:00 | true | [N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7](O)=O.Cl.CN(C)CCCN=C=NCC.N1C=CC=CC=1.[N:28]1[CH:33]=[CH:32][CH:31]=[C:30]([O:34][C:35]2[CH:36]=[C:37]([NH2:49])[C:38]([NH2:48])=[CH:39][C:40]=2[O:41][C:42]2[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=2)[CH:29]=1>C(OCC)(=O)C>[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1[NH:49][C:37]2[C... | Nc1cc(Oc2cccnc2)c(Oc2cccnc2)cc1N | O=C(O)c1cnccn1 | null | CCN=C=NCCCN(C)C | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | c1ccncc1 | null | null | null | null | null | null | null | null | null | 25 | 8 | 7.7 mg of pyrazine-2-carboxylic acid and 20 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide monohydrochloride were added to a pyridine (1 ml) solution of 15 mg of 4,5-bis(pyridin-3-yloxy)-benzene-1,2-diamine obtained in Example 1 (step 3), and the reaction liquid was stirred overnight at room temperature. The react... | c1cncc(Oc2cc3nc(-c4cnccn4)[nH]c3cc2Oc2cccnc2)c1 | null | null | null |
1,065,588 | ord_dataset-ffbef48837674f39816de887b5dc8bae | null | 2011-01-01T00:06:00 | true | [F:1][C:2]([F:18])([F:17])[CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[C:15]([CH3:16])=[CH:14][S:13][CH:12]=1)[OH:4].[NH2:19][C:20]1[N:25]=[C:24](Cl)[CH:23]=[C:22]([Cl:27])[N:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O1CCOCC1>C(OCC)(=O)C>[Cl:27][C:22]1[CH:23]=[C:24]([O:4][CH:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=... | Cc1cscc1-c1ccccc1C(O)C(F)(F)F | Nc1nc(Cl)cc(Cl)n1 | null | O=C([O-])[O-] | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 110 | null | A mixture of 2,2,2-trifluoro-1-[2-(4-methyl-thiophen-3-yl)-phenyl]-ethanol (100 mg, 0.37 mmol), 2-amino-4,6-dichloro-pyrimidine (54 mg, 0.33 mmol), cesium carbonate (481 mg, 1.48 mmol) and 1,4-dioxane (1 ml) was heated at 110° C. overnight. The reaction mixture was cooled to room temperature; 10 ml of ethyl acetate was... | Cc1cscc1-c1ccccc1C(Oc1cc(Cl)nc(N)n1)C(F)(F)F | null | 75.8 | null |
463,925 | ord_dataset-6c36eb0f817d4144988b8963c5d58879 | null | 2000-01-01T00:05:00 | true | [N+:1]([C:4]1[CH:5]=[C:6]([OH:13])[CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1)([O-:3])=[O:2].Br[CH2:15][C:16]#[N:17].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CC(=O)CC>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1)[O:13][CH2:15][C:16]#[N:17])([O-:3])=[O:2] | N#CCBr | O=[N+]([O-])c1cc(O)cc([N+](=O)[O-])c1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCC(C)=O | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 70 | null | 3,5-Dinitrophenol (15.0 g) and 10.75 g of bromoacetonitrile were dissolved in 85 ml of 2-butanone and the solution was treated with 33.78 g of potassium carbonate. The heterogenous mixture was stirred and heated at 70° C. for 5 hours, cooled to room temperature, poured into ethyl acetate, washed with water, dried over ... | N#CCOc1cc([N+](=O)[O-])cc([N+](=O)[O-])c1 | null | 61.8 | null |
1,133,787 | ord_dataset-aaeaab5f3720492494c1cbbdd0ed2820 | null | 2012-01-01T00:02:00 | true | C[O:2][C:3](=[O:52])[C:4]1[CH:51]=[CH:50][C:7]([C:8]([NH:10][C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([S:20]([C:23]4[CH:28]=[C:27]([F:29])[CH:26]=[C:25]([F:30])[CH:24]=4)(=[O:22])=[O:21])[CH:18]=3)[N:13]([C:31]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[C:32]3[CH:3... | COC(=O)c1ccc(C(=O)Nc2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)c3ccc(S(=O)(=O)c4cc(F)cc(F)c4)cc23)cc1 | null | null | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 8 | A mixture of N-[5-(3,5-difluoro-benzenesulfonyl)-1-trityl-1H-indazol-3-yl]-terephthalamic acid methyl ester (400 mg, 0.56 mmol), tetrahydrofuran (8 mL), water (4 mL) and lithium hydroxide hydrate (35 mg, 1.5 eq) was stirred at room temperature overnight. The solvents were evaporated to dryness. The residue was taken up... | O=C(O)c1ccc(C(=O)Nc2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)c3ccc(S(=O)(=O)c4cc(F)cc(F)c4)cc23)cc1 | null | null | null |
931,676 | ord_dataset-d8a5dc784dde4465894ec7c69d2e3ba6 | null | 2010-01-01T00:01:00 | true | [Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.[CH3:10][CH:11]1[CH2:16][NH:15][CH2:14][CH2:13][NH:12]1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:15]2[CH2:14][CH2:13][NH:12][CH:11]([CH3:10])[CH2:16]2)=[CH:4][CH:3]=1 | Clc1ccc(CBr)cc1 | CC1CNCCN1 | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 16 | 3.49 g (17.0 mmol) 4-Chlorobenzylbromide was added dropwise to a mixture of 2.04 g (20.4 mmol) 2-Methyl piperazine and 2.40 ml (17 mmol) triethylamine in 60 ml DMF at room temperature. The reaction mixture was stirred for 16 hours at room temperature, the poured onto aq. sodium bicarbonate solution and extracted with e... | CC1CN(Cc2ccc(Cl)cc2)CCN1 | null | 59.4 | null |
1,479,971 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | Br[C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[F:22])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([Cl:18])([F:17])[F:16])=[CH:10][CH:9]=1)=[O:6].[F:23][C:24]1[CH:25]=[N:26][NH:27][C:28]=1[Sn](CCCC)(CCCC)CCCC.C([O-])([O-])=O.[Na+].[Na+]>CS(C)=O.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P... | CCCC[Sn](CCCC)(CCCC)c1[nH]ncc1F | O=C(Nc1ccc(OC(F)(F)Cl)cc1)c1ccc(F)c(Br)c1 | 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 | CS(C)=O | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 100 | 20 | A mixture of 3-bromo-N-(4-(chlorodifluoromethoxy)phenyl)-4-fluorobenzamide (Stage 20.2, 200 mg, 0.497 mmol), 4-fluoro-5-(tributylstannyl)-1H-pyrazole (211 mg, 0.472 mmol) and Pd(PPh3)4 (28.7 mg, 0.025 mmol) in DMSO (1.5 mL) in a sealed vial was stirred at 100° C. for 20 h under an argon atmosphere. The RM was diluted w... | O=C(Nc1ccc(OC(F)(F)Cl)cc1)c1ccc(F)c(-c2[nH]ncc2F)c1 | null | null | null |
1,186,039 | ord_dataset-9cd817a75dfc4fe7ad19d4232772d5ff | null | 2012-01-01T00:07:00 | true | Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:3].[CH2:14]([CH:17]1[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]1)[C:15]#[CH:16]>>[CH2:14]([CH:17]1[CH2:22][CH2:21][N:20]([C:2]([O:4][C:5]2[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=2)=[O:3])[CH2:19][CH2:18]1)[C:... | C#CCC1CCN(C(=O)OC(C)(C)C)CC1 | O=C(Cl)Oc1ccc([N+](=O)[O-])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 | 4-(nitro)phenyl chloroformate (5.0 g, 24.8 mmol) was added to a solution of tert-butyl 4-(prop-2-ynyl)piperidine-1-carboxylate (4.25 g, 19.0 mmol) according to general procedure 1. Yield=5.72 g, 80%. m/z MH+=289.04. HPLC rt=10.4 min. | C#CCC1CCN(C(=O)Oc2ccc([N+](=O)[O-])cc2)CC1 | null | null | null |
1,478,662 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [CH3:1][C:2]1[O:6][N:5]=[C:4]([O:7][CH:8]2[CH2:11][N:10]([C:12]3[N:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][C:13]=3[C:14]([O:16]C)=[O:15])[CH2:9]2)[CH:3]=1.O.[OH-].[Li+]>O1CCOCC1.O>[CH3:1][C:2]1[O:6][N:5]=[C:4]([O:7][CH:8]2[CH2:11][N:10]([C:12]3[N:21]=[CH:20][C:19]([C:22]([F:25])([F:23])[F:24])=[CH:18][C... | COC(=O)c1cc(C(F)(F)F)cnc1N1CC(Oc2cc(C)on2)C1 | null | null | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | To a solution of methyl 2-(3-((5-methylisoxazol-3-yl)oxy)azetidin-1-yl)-5-(trifluoromethyl)nicotinate (D88) (20 mg, 0.056 mmol) in 1,4-dioxane/water (3 ml/1 ml), lithium hydroxide monohydrate (3.52 mg, 0.084 mmol) and the resulting mixture was heated at 130° C. under microwave irradiation 10 min (2 cycles of 5 min each... | Cc1cc(OC2CN(c3ncc(C(F)(F)F)cc3C(=O)O)C2)no1 | null | 98.8 | null |
1,097,178 | ord_dataset-af85e6f81c2d49f08086afd6d9e6959c | null | 2011-01-01T00:10:00 | true | [N:1]1[CH:6]=[CH:5][C:4]([CH2:7][NH:8][C:9]2[CH:28]=[CH:27][CH:26]=[CH:25][C:10]=2[C:11]([NH:13][O:14][CH2:15][C:16]2[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][CH:17]=2)=[O:12])=[CH:3][CH:2]=1.[CH3:29][N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1>>[CH3:29][N:30]1[CH2:35][CH2:34][N:33]([C:20]([C:19]2[CH:18]=[CH:1... | CN1CCNCC1 | O=C(O)c1ccc(CONC(=O)c2ccccc2NCc2ccncc2)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 | Prepared by a similar procedure as described for preparation of example 405. Starting materials: 4-{2-[(Pyridin-4-ylmethyl)-amino]-benzoylaminooxymethyl}-benzoic acid (see example 404) and 1-methylpiperazine. The title compound was crystallised from toluene. 13C-NMR (DMSO-d6) δ 168.6, 167.2, 149.5, 148.9, 148.2, 137.3,... | CN1CCN(C(=O)c2ccc(CONC(=O)c3ccccc3NCc3ccncc3)cc2)CC1 | null | null | null |
736,539 | ord_dataset-76dd1b78ee414d2da0ed30700ef026f7 | null | 2006-01-01T00:10:00 | true | [NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([CH3:15])([CH3:14])[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:6]=1.[Cl:16][C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([CH3:24])[C:18]=1[S:25](Cl)(=[O:27])=[O:26]>>[Cl:16][C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([CH3:24])[C:18]=1[S:25]([NH:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([CH... | Cc1cc(Cl)cc(Cl)c1S(=O)(=O)Cl | CCOC(=O)CC(C)(C)c1csc(N)n1 | null | null | null | null | null | null | null | 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 ethyl 3-(2-amino-1,3-thiazol-4-yl)-3-methylbutanoate (METHOD I) and 2,4-dichloro-6-methylbenzenesulfonyl chloride as described in the synthetic method to give a white solid (55.0 mg) with purity >90%. MS (pos) m/z 451.2, 453.2. | CCOC(=O)CC(C)(C)c1csc(NS(=O)(=O)c2c(C)cc(Cl)cc2Cl)n1 | null | null | null |
109,864 | ord_dataset-406d20cb3f314e2c967b14f55925f895 | null | 1983-01-01T00:10:00 | true | [CH2:1]([N:3]1[CH2:7][C:6](O[Si](C)(C)C)=[C:5](O[Si](C)(C)C)[CH2:4]1)[CH3:2].Cl.Cl.[NH2:20][CH2:21][C:22]([NH2:24])=[NH:23]>>[CH2:1]([N:3]1[CH2:7][C:6]2[C:5](=[N:23][C:22]([NH2:24])=[CH:21][N:20]=2)[CH2:4]1)[CH3:2] | N=C(N)CN | CCN1CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C1 | 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 | This compound was prepared analogous to Example 22 from 1-ethyl-2,5-dihydro-3,4-bis(trimethylsilyloxy)-pyrrole and α-amino-acetamidine dihydrochloride. | CCN1Cc2ncc(N)nc2C1 | null | null | null |
1,019,989 | ord_dataset-f024e9664ab64906a71a2ff6004cb3d0 | null | 2010-01-01T00:12:00 | true | [Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([NH2:13])=[O:12])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:14]1[CH2:19][CH2:18][N:17]([S:20]([CH:23]=[CH2:24])(=[O:22])=[O:21])[CH2:16][CH2:15]1.[CH3:25][O-:26].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([NH2:13])=[O:12])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:14]1[CH2:19][CH2:18... | C=CS(=O)(=O)N1CCC(c2c[nH]c3c(C(N)=O)cc(Br)cc23)CC1 | C[O-] | null | [Na+] | 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 | 80 | 1 | The mixture of 5-bromo-3-[1-(ethenylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide (150 mg, 0.36 mmol), sodium methoxide in methanol (25%, 1.0 mL) and methanol (2.0 mL) was stirred at 80° C. for 1 hr. After which time the reaction mixture was concentrated under reduced pressure. The residue was purified by combiflash... | COCCS(=O)(=O)N1CCC(c2c[nH]c3c(C(N)=O)cc(Br)cc23)CC1 | null | 63 | null |
1,011,397 | ord_dataset-7448b89163bf426c9d9777809ce24cec | null | 2010-01-01T00:11:00 | true | [CH:1]([C:3]1[O:7][C:6]([B:8]([OH:10])[OH:9])=[CH:5][CH:4]=1)=O.[CH3:11][NH:12][CH3:13]>COCCOC.C1COCC1>[CH3:11][N:12]([CH2:1][C:3]1[O:7][C:6]([B:8]([OH:10])[OH:9])=[CH:5][CH:4]=1)[CH3:13] | CNC | O=Cc1ccc(B(O)O)o1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COCCOC | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 0.08 | To a solution of (5-formyl-2-furyl)boronic acid (50 mg, 0.36 mmol) in DME (1.0 mL) was added a 2.0M solution of dimethylamine in THF (0.53 mL, 1.0 mmol). The reaction mixture stirred for 5 minutes before resin bound MP-BH(OAc)3 (2.2 mmol/g, 0.33 g, 0.714 mmol) was added. The reaction mixture was stirred at room tempera... | CN(C)Cc1ccc(B(O)O)o1 | null | null | null |
1,636,106 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | [CH3:1][C:2]1([CH3:28])[CH2:5][CH:4]([CH:6]([NH:16][C:17]2[C:26]([CH3:27])=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=2)[C:7]2[CH:15]=[CH:14][C:10]([C:11](O)=[O:12])=[CH:9][CH:8]=2)[CH2:3]1.Cl.CN(C)CCCN=C=NCC.Cl.[CH3:42][O:43][C:44](=[O:48])[CH2:45][CH2:46][NH2:47].C(N(CC)CC)C>ClCCl>[CH3:42][O:43][C:4... | Cc1cc2ccccc2nc1NC(c1ccc(C(=O)O)cc1)C1CC(C)(C)C1 | COC(=O)CCN | null | CCN=C=NCCCN(C)C | Cl | 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 | null | null | (+/−)-4-[(3,3-dimethyl-cyclobutyl)-(3-methyl-quinolin-2-ylamino)-methyl]-benzoic acid (Intermediate 26, 1.0 eq.), 1-hydrobenzotriazole hydrate (1.2 eq.), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (1.2 eq.), beta-alanine methyl ester hydrochloride (1.1 eq.), and triethylamine (1.3 eq.) were combined i... | COC(=O)CCNC(=O)c1ccc(C(Nc2nc3ccccc3cc2C)C2CC(C)(C)C2)cc1 | null | null | null |
1,703,114 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | [CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH:6]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:7]1.CCN(CC)CC>C(Cl)Cl>[CH3:1][S:2]([N:6]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:16])([CH3:15])[CH3:17])[CH2:7]1)(=[O:4])=[O:3] | CC(C)(C)OC(=O)N[C@H]1CCNC1 | CS(=O)(=O)Cl | 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 | null | 2 | Methane sulfonyl chloride (204 mg, 1.78 mmol) was added to a solution of (S)-tert-butyl pyrrolidin-3-ylcarbamate (300 mg, 1.62 mmol) and Et3N (197 mg, 1.94 mmol) in DCM (6 mL) at 0-5° C.; stirring was continued at 20-35° C. for 2 h. The reaction mixture was diluted with DCM, washed with water, aqueous NaHCO3 solution f... | CC(C)(C)OC(=O)N[C@H]1CCN(S(C)(=O)=O)C1 | null | 58.4 | null |
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