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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
419,413 | ord_dataset-94e21e9990034c729ea727e7d2ab0eb0 | null | 1998-01-01T00:12:00 | true | [NH2:1][C:2]1[C:11]([F:12])=[C:10]([F:13])[C:9]([CH3:14])=[C:8]2[C:3]=1[C:4](=[O:24])[C:5]([C:19]([O:21]CC)=[O:20])=[CH:6][N:7]2[C@@H:15]1[CH2:17][C@@H:16]1[F:18].C(O)(=O)C.Cl>O>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([F:13])[C:9]([CH3:14])=[C:8]2[C:3]=1[C:4](=[O:24])[C:5]([C:19]([OH:21])=[O:20])=[CH:6][N:7]2[C@@H:15]1[CH2:... | CCOC(=O)c1cn([C@@H]2C[C@@H]2F)c2c(C)c(F)c(F)c(N)c2c1=O | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | A 10.43 g (30.6 mmol) portion of ethyl 5-amino-6,7-difluoro-[(1R,2S)-2-fluorocyclopropyl]-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylate was mixed with 150 ml of acetic acid and 150 ml of concentrated hydrochloric acid and then heated under reflux for 1 hour. After completion of the reaction, the reaction solution w... | Cc1c(F)c(F)c(N)c2c(=O)c(C(=O)O)cn([C@@H]3C[C@@H]3F)c12 | null | 79 | null |
1,443,175 | ord_dataset-275a3da8f45f4536ad29727f0ef9ba66 | null | 2014-01-01T00:06:00 | true | [CH3:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:7][C:5]=2[N:6]=1.C1C(=O)N([Br:23])C(=O)C1>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:23][CH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]([F:13])([F:15])[F:14])[CH:8]=[CH:7][C:5]=2[N:6]=1 | O=C1CCC(=O)N1Br | Cc1nc2ccc(OC(F)(F)F)cc2s1 | null | O=C(OOC(=O)c1ccccc1)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 2-methyl-6-(trifluoromethoxy)benzo[d]thiazole (9 g, 0.0386 mol) and NBS (6.9 g, 0.0386 mol) and benzoyl peroxide (0.25 g) in CCl4 (250 ml) was heated to reflux under lamp light (150 Watt) for 4 hr. Then the mixture was filtered, evaporated and purified using the Combi-Flash instrument to give 4.3 g (28.5%)... | FC(F)(F)Oc1ccc2nc(CBr)sc2c1 | null | 38.2 | null |
34,621 | ord_dataset-2e96d163c3f64eb5b470e1ea1a41922a | null | 1977-01-01T00:12:00 | true | C(OC([NH:8][CH:9]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:10]([NH:12][CH:13]1[C:36](=[O:37])[N:15]2[C:16]([C:29]([O:31]C(C)(C)C)=[O:30])=[C:17]([CH:20]=[CH:21][C:22]([O:24]C(C)(C)C)=[O:23])[CH2:18][S:19][C@H:14]12)=[O:11])=O)(C)(C)C>C(O)=O>[NH2:8][CH:9]([C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)[C:10]([N... | CC(C)(C)OC(=O)C=CC1=C(C(=O)OC(C)(C)C)N2C(=O)C(NC(=O)C(NC(=O)OC(C)(C)C)c3ccccc3)[C@H]2SC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=CO | null | null | null | null | null | null | null | null | null | null | null | 1 | A solution of 25 mg. of tert-butyl 7-(2'-tert-butoxycarbonylamino-2'-phenylacetamido)-3-(2'-tert-butoxycarbonylvinyl)-3-cephem-4-carboxylate, prepared as described in Example 19, in 5 cc of 98-100 percent formic acid was allowed to stand for 1 hour at room temperature. After evaporating under reduced pressure the formi... | NC(C(=O)NC1C(=O)N2C(C(=O)O)=C(C=CC(=O)O)CS[C@H]12)c1ccccc1 | null | null | null |
1,696,880 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8]C)[C:3]=1[C:10]1[NH:29][C:13]2=[CH:14][C:15]3[C:16](=[O:28])[N:17]([CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])[C:18](=[O:22])[C:19]=3[C:20]([CH3:21])=[C:12]2[N:11]=1.Cl>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[C:3]=1[C:10]1[NH:29][C:13]2=[CH:14][C:15]3[C:16](=[O:28])... | COc1nccc(Cl)c1-c1nc2c(C)c3c(cc2[nH]1)C(=O)N(CCN(C)C)C3=O | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | 47.5 | null | A solution of 2-(4-chloro-2-methoxypyridin-3-yl)-6-(2-(dimethylamino)ethyl)-4-methylimidazo[4,5-f]isoindole-5,7(1H,6H)-dione in a mixture of 1,4-dioxane (14 mL) and concentrated HCl (2.5 mL) was heated at 45-50° C. for 14 h. After the end of reaction was established by TLC, the reaction mixture was concentrated under v... | Cc1c2c(cc3[nH]c(-c4c(Cl)cc[nH]c4=O)nc13)C(=O)N(CCN(C)C)C2=O | null | null | null |
1,004,694 | ord_dataset-70899a0178cc441482746c093624afa0 | null | 2010-01-01T00:10:00 | true | Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]3[O:15][CH2:16][CH2:17][O:18][C:11]=3[CH:10]=2)[C:5]([F:19])=[CH:4][N:3]=1.[CH3:20][O:21][C:22]1[CH:23]=[CH:24][C:25]([CH3:29])=[C:26]([CH:28]=1)[NH2:27]>>[CH2:17]1[CH2:16][O:15][C:12]2[CH:13]=[CH:14][C:9]([NH:8][C:6]3[C:5]([F:19])=[CH:4][N:3]=[C:2]([NH:27][C:26]4[CH... | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2 | COc1ccc(C)c(N)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 | In like manner to the preparation of 5-fluoro-N4-(3-hydroxyphenyl)-N2-[4-(3-phenyl-1,2,4-oxadiazol-5-yl)methyleneoxyphenyl]-2,4-pyrimidinediamine, 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine and 5-methoxy-2-methylaniline were reacted to provide N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(5-methoxy-2-... | COc1ccc(C)c(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 | null | null | null |
851,498 | ord_dataset-171b840ae6e84e45bab43b987d09f5c7 | null | 2008-01-01T00:11:00 | true | [Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][NH2:11].[N+:12]([C:15]1[CH:16]=[C:17]2[C:22](=O)[O:21][C:19](=[O:20])[C:18]2=[CH:24][CH:25]=1)([O-:14])=[O:13]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][N:11]1[C:22](=[O:21])[C:17]2[C:18](=[CH:24][CH:25]=[C:15](... | NCCc1ccc(Cl)cc1Cl | O=C1OC(=O)c2cc([N+](=O)[O-])ccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | 150 | 2 | 2-(2,4-dichlorophenyl)ethanamine was suspended in toluene with 4-nitrophthalic anhydride (1 eq) and heated to 150° C. After 2 hours, the reaction was cooled and checked for completion by LC/MS. The solvent was then removed in vacuo and the resulting product was taken on to the next step without further purification. Rt... | O=C1c2ccc([N+](=O)[O-])cc2C(=O)N1CCc1ccc(Cl)cc1Cl | null | null | null |
922,051 | ord_dataset-8e59bd24817446f7b1c68e805b8e5f1d | null | 2009-01-01T00:11:00 | true | [C:1]1([C:7](Cl)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:21][C:22]([F:34])([F:33])[C:23]1[C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:26][NH:25][N:24]=1.C(N(CC)CC)C>CN(C)C=O>[CH2:31]([O:30][C:28]([C:27]1[C:23]([C:22]([F:33])(... | ClC(c1ccccc1)(c1ccccc1)c1ccccc1 | CCOC(=O)c1c[nH]nc1C(F)(F)F | null | null | null | 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 | 8 | Triphenylmethyl chloride (1.1 g, 3.6 mmol) was added to a solution of ethyl 3-(trifluoromethyl)-pyrazole-4-carboxylate (0.75 g, 3.6 mmol) and triethylamine (1 mL, 7.2 mmol) in N,N-dimethylformamide (12 mL). This mixture was stirred at room temperature overnight, then the solvent was evaporated and the residue was dilut... | CCOC(=O)c1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)nc1C(F)(F)F | null | 78.9 | null |
1,694,915 | ord_dataset-c1e70ad912eb438f8d34b1dc681f809a | null | 2016-01-01T00:02:00 | true | [C:1]([O:5][C:6]([N:8]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]2[N:25]=[C:24]([C:26]#[C:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[CH2:34][C:35]([O:37][CH3:38])=[O:36])[C:23]([C:39]([F:42])([F:41])[F:40])=[CH:22][N:21]=2)=[CH:15][CH:14]=1)[CH2:9][CH2:10][OH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCOC(C)=O... | COC(=O)Cc1ccccc1C#Cc1nc(Nc2ccc(CN(CCO)C(=O)OC(C)(C)C)cc2)ncc1C(F)(F)F | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | 18 | A suspension of methyl 2-(2-((2-((4-(((tert-butoxycarbonyl)(2-hydroxyethyl)amino)methyl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethynyl)phenyl)acetate (A72) (0.589 g, 1.00 mmol) and 10% Pd/C (0.300 g) in EtOAc (13 mL) was stirred under a hydrogen atmosphere for 18 hours. A further portion of 10% Pd/C (0.300 g) ... | COC(=O)Cc1ccccc1CCc1nc(Nc2ccc(CN(CCO)C(=O)OC(C)(C)C)cc2)ncc1C(F)(F)F | null | null | null |
1,575,282 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | [CH:1]1[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[NH:6][C:5]=2[CH:4]=[CH:3][N:2]=1.[Br:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1I.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cu]>[Br:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:6]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=2[C:13]2[CH:1]=[N:2][CH:3]=[CH:4][C:5... | c1ccc2c(c1)[nH]c1ccncc12 | Brc1ccccc1I | null | [Cu] | O=C([O-])[O-] | [K+] | 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 | 130 | 24 | A mixture of 84.1 g (500 mmol) of 5H-pyrido[4,3-b]indole [244-69-9], 147.1 g (520 mmol) of 2-bromoiodobenzene [583-55-1], 103.7 g (750 mmol) of potassium carbonate, 31.8 g (500 mmol) of copper powder and 300 g of glass beads (diameter 3 mm) in 800 ml of DMF is stirred at 130° C. for 24 h. After cooling, the mixture is ... | Brc1ccccc1-n1c2ccccc2c2cnccc21 | null | null | null |
654,280 | ord_dataset-fe016e2f90e741a590ad77fd5933161f | null | 2004-01-01T00:11:00 | true | Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8]C(=O)C(F)(F)F)=[C:4]([F:15])[CH:3]=1.[NH2:16][C:17]1[N:22]=[C:21]([NH2:23])[C:20]([CH2:24][C:25]2[CH:26]=[C:27]([O:40][CH2:41][CH3:42])[C:28](I)=[C:29]([O:31][S:32]([CH:35]([CH2:37][CH3:38])[CH3:36])(=[O:34])=[O:33])[CH:30]=2)=[CH:19][N:18]=1>>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([C:28]2[C:2... | CCOc1cc(Cc2cnc(N)nc2N)cc(OS(=O)(=O)C(C)CC)c1I | O=C(Nc1ccc(Br)cc1F)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 | null | Starting from 241 mg (0.84 mmol) N-(4-bromo-2-fluoro-phenyl)-2,2,2-trifluoro-acetamide and 214 mg (0.422 mmol) butane-2-sulphonic acid 5-(2,4-diamino-pyrimidin-5-ylmethyl)-3-ethoxy-2-iodo-phenyl ester, 85 mg of the tide compound are obtained as a pale brown powder. | CCOc1cc(Cc2cnc(N)nc2N)cc(OS(=O)(=O)C(C)CC)c1-c1ccc(N)c(F)c1 | null | null | null |
261,114 | ord_dataset-ab5ba9f863cb41d9924be0bb3c730818 | null | 1993-01-01T00:01:00 | true | [CH3:1][C:2]1[C:7](=[O:8])[C:6]([CH3:9])=[C:5]([CH3:10])[C:4](=[O:11])[C:3]=1[CH:12]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([NH:20][CH2:21][C:22]([O:24]CC1C=CC=CC=1)=[O:23])=[O:19]>C(O)C.[Pd]>[CH3:1][C:2]1[C:7](=[O:8])[C:6]([CH3:9])=[C:5]([CH3:10])[C:4](=[O:11])[C:... | CC1=C(C)C(=O)C(C(CCCCCC(=O)NCC(=O)OCc2ccccc2)c2ccccc2)=C(C)C1=O | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | Benzyl 7-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-7-phenylheptanoylglycinate (0.78 g) in ethanol (8 ml) was hydrogenated in the presence of 5% palladium-charcoal (0.08 g) at room temperature. After the reaction was completed, the catalyst was removed by filtration. The solution was treated with ferric chloride (0.51 g) i... | CC1=C(C)C(=O)C(C(CCCCCC(=O)NCC(=O)O)c2ccccc2)=C(C)C1=O | null | 98.5 | null |
1,662,837 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [CH:1]([NH:3][CH2:4][C:5]1[N:10]=[C:9]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)[C:8]([C:24]([O:26][CH3:27])=[O:25])=[CH:7][CH:6]=1)=[O:2].[Cl:28]N1C(=O)CCC1=O>O1CCCC1>[Cl:28][C:6]1[CH:7]=[C:8]([C:24]([O:26][CH3:27])=[O:25])[C:9]([N:11]2[CH2:16][CH2:15][N:1... | COC(=O)c1ccc(CNC=O)nc1N1CCN(C(=O)OC(C)(C)C)CC1 | O=C1CCC(=O)N1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | tert-Butyl 4-{6-[(formylamino)methyl]-3-(methoxycarbonyl)pyridin-2-yl}piperazine-1-carboxylate (4.85 g, 0.0128 mol) and N-chlorosuccinimide (2.1 g, 15 mmol) was stirred in tetrahydrofuran (85 mL) at 50° C. for 16 hours. Evaporation and purification on silica gel using ethyl acetate in hexanes (0-80%) gave the desired c... | COC(=O)c1cc(Cl)c(CNC=O)nc1N1CCN(C(=O)OC(C)(C)C)CC1 | null | 106 | null |
518,013 | ord_dataset-a495451286334c5c9bbcbd48a00c1350 | null | 2001-01-01T00:09:00 | true | [CH3:1][N:2]([CH3:26])[C:3](=[O:25])[CH2:4][C:5]1[CH:10]=[C:9]([C:11](=O)[CH3:12])[CH:8]=[CH:7][C:6]=1[NH:14][C:15]1[C:20]([F:21])=[C:19]([F:22])[CH:18]=[C:17]([F:23])[C:16]=1[F:24]>CC(O)=O.[Pd]>[CH3:26][N:2]([CH3:1])[C:3](=[O:25])[CH2:4][C:5]1[CH:10]=[C:9]([CH2:11][CH3:12])[CH:8]=[CH:7][C:6]=1[NH:14][C:15]1[C:20]([F:2... | CC(=O)c1ccc(Nc2c(F)c(F)cc(F)c2F)c(CC(=O)N(C)C)c1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | N,N-dimethyl-5-acetyl-2-(2′,3′,5′,6′-tetrafluoroanilino)phenylacetamide (30 g, 0.802 mol) is dissolved in HOAc (150 ml) and hydrogenated (55 psi) with a 10% Pd/C (1.5 g) catalyst for 8 hours. The catalyst is removed by filtration through Celite and the filtrate poured into water (500 ml) and EtOAc (500 ml). The organic... | CCc1ccc(Nc2c(F)c(F)cc(F)c2F)c(CC(=O)N(C)C)c1 | null | null | null |
372,071 | ord_dataset-15cdba4c7f064b3f9cd7343cb3187881 | null | 1997-01-01T00:07:00 | true | [Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11](OCC)=[O:12])=[C:7]2[C:16]([O:18]CC)=O.O.[NH2:22][NH2:23]>C(O)C>[Cl:1][C:2]1[C:10]2[NH:9][C:8]3[C:11](=[O:12])[N:22]=[N:23][C:16](=[O:18])[C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1 | NN | CCOC(=O)c1[nH]c2c(Cl)cccc2c1C(=O)OCC | 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 | 25 | null | To a stirred solution of diethyl 7-chloroindole-2,3-dicarboxylate (0.6 g, 2.0 mM) in ethanol (4 mL) was added hydrazine hydrate (2 mL, 40 mM). The resulting solution was heated to reflux for 3 hrs during which time a white precipitate formed. The solid was filtered, suspended in acetic acid (2 mL), and warmed to reflux... | O=C1N=NC(=O)c2c1[nH]c1c(Cl)cccc21 | null | 23 | null |
110,962 | ord_dataset-ac04cf1ba5724e9b93d39b77e9740b21 | null | 1983-01-01T00:11:00 | true | [CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.[ClH:11].NCCC1C=CC(OC)=C2C=1[CH2:17][C:18](=[O:26])[NH:19]2>>[ClH:11].[NH2:8][CH2:7][C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[C:4]2[C:5]=1[CH2:17][C:18](=[O:26])[NH:19]2 | COc1ccc(CCN)c2c1NC(=O)C2 | COc1ccc(CN)cc1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Using 65 g of p-methoxybenzylamine for the starting material of Example 1 gives 4-aminomethyl-7-methoxy-2(3H)-indolone hydrochloride. This material (2 g) was converted to the base and alkylated using 1 mole equivalent of isovaleraldehyde as in Example 2 to give 4-isopentylaminomethyl-7-methoxy-2(3H)-indolone hydrobromi... | COc1ccc(CN)c2c1NC(=O)C2 | null | null | null |
252,721 | ord_dataset-49bd993346b64eeeb2a8fe2643164a0a | null | 1992-01-01T00:08:00 | true | [NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C@@H:6]1[CH2:10][C@@H:9]([OH:11])[CH2:8][N:7]1[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1)=[O:13].[N+:25]([C:28]1[CH:38]=[CH:37][C:31]([CH2:32][O:33][C:34](Cl)=[O:35])=[CH:30][CH:29]=1)([O-:27])=[O:26].[OH-].[Na+]>O.O1CCCC1>[OH:11][C@H:9]1... | O=C(OCc1ccc([N+](=O)[O-])cc1)N1C[C@H](O)C[C@H]1c1ncc[nH]1 | O=C(Cl)OCc1ccc([N+](=O)[O-])cc1 | null | [Na+] | [OH-] | 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 | null | null | To a solution of (2S,4R)-2-(imidazol-2-yl)-4-hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1.0 g) in a mixture of water (10 ml) and tetrahydrofuran (20 ml) was dropwise added a solution of 4-nitrobenzyloxycarbonyl chloride (0.85 g) in tetrahydrofuran (5 ml) under ice-cooling with stirring, keeping the pH between 9 a... | O=C(OCc1ccc([N+](=O)[O-])cc1)N1C[C@H](O)C[C@H]1c1nccn1C(=O)OCc1ccc([N+](=O)[O-])cc1 | null | 63 | null |
662,696 | ord_dataset-5a3d853c53674888a5691dce2e398792 | null | 2005-01-01T00:03:00 | true | [Cl:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]([CH2:14]OS(C)(=O)=O)=[CH:10][C:9]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([F:28])[CH:21]=3)=[N:8]2)=[CH:4][CH:3]=1.[CH3:31][NH:32][CH3:33]>>[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]([CH2:14][N:32]([CH3:33])[CH3:31]... | COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(Cc3ccc(Cl)cc3)n2)cc1F | CNC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Following the procedure of Example 7, 2-(4-chlorobenzyl)-6-(3-fluoro-4-methoxyphenyl)-4-methanesulfonyloxymethyl-2H-pyridazin-3-one and dimethylamine were reacted to yield the title compound as a slightly-yellow crystalline powder (yield: 74.7%). | COc1ccc(-c2cc(CN(C)C)c(=O)n(Cc3ccc(Cl)cc3)n2)cc1F | null | 74.7 | null |
1,440,845 | ord_dataset-275a3da8f45f4536ad29727f0ef9ba66 | null | 2014-01-01T00:06:00 | true | [NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[CH:11]=[C:10]([C:12]3[CH:17]=[N:16][N:15]4[C:18]([C:21]5[CH:22]=[C:23]([NH:27][C:28]([NH:30][CH2:31][C:32]([F:35])([F:34])[F:33])=[O:29])[CH:24]=[CH:25][CH:26]=5)=[CH:19][N:20]=[C:14]4[CH:13]=3)[CH:9]=[N:8]2)[CH2:3][CH2:2]1.[CH3:36][O:37][CH2:38][C:39](Cl)=[O:40].C(N(CC)C(C)C)(C)C>CS(... | O=C(NCC(F)(F)F)Nc1cccc(-c2cnc3cc(-c4cnn(C5CCNCC5)c4)cnn23)c1 | COCC(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | null | null | A mixture of N-{3-[7-(1-piperidin-4-yl-1H-pyrazol-4-yl)imidazo[1,2-b]pyridazin-3-yl]phenyl}-N′-(2,2,2-trifluoroethyl)urea (20.0 mg, 0.0413 mmol), methoxyacetyl chloride (5.66 μL, 0.0619 mmol) and N,N-diisopropylethylamine (40.0 μL, 0.230 mmol, Aldrich, Cat. No. M9653) in dimethylsulfoxide (DMSO) (0.5 mL) was stirred at... | COCC(=O)N1CCC(n2cc(-c3cnn4c(-c5cccc(NC(=O)NCC(F)(F)F)c5)cnc4c3)cn2)CC1 | null | null | null |
558,125 | ord_dataset-f483e698250b4da0a84f425c7bfa965a | null | 2002-01-01T00:08:00 | true | Cl.C(O[C:7](=O)[C@H:8]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[NH2:9])(C)(C)C.[CH3:18][O:19][C:20]1[CH:25]=[C:24]([CH3:26])[C:23]([S:27](Cl)(=[O:29])=[O:28])=[C:22]([CH3:31])[C:21]=1[CH3:32].C(N(CC)C(C)C)(C)C>CN(C)C=O>[CH3:18][O:19][C:20]1[CH:25]=[C:24]([CH3:26])[C:23]([S:27]([NH:9][C@H:8]([CH2:10][C:11... | CC(C)(C)OC(=O)[C@@H](N)Cc1ccccc1 | COc1cc(C)c(S(=O)(=O)Cl)c(C)c1C | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 2 | To a solution of 0.5 g of L-phenylalanine t-butyl ester hydrochloride in 4 mL of N,N-dimethylformamide were added 0.67 g of 4-methoxy-2,3,6-trimethylphenylsulfonylchloride and 0.96 mL of N,N-diisopropylethylamine. After stirring for 2 hours at room temperature the reaction mixture was concentrated and the residue disso... | COc1cc(C)c(S(=O)(=O)N[C@@H](C)Cc2ccccc2)c(C)c1C | null | 96.4 | null |
818,342 | ord_dataset-50f99930fc41474db226bc80774b38df | null | 2008-01-01T00:04:00 | true | C[Si]([C:5]#[C:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)(C)C.Cl[C:14]1[N:15]=[N:16][C:17]([CH3:20])=[CH:18][CH:19]=1.[I-].C(N(CC)CC)C>COCCOC>[CH3:20][C:17]1[N:16]=[N:15][C:14]([C:5]#[C:6][C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)=[CH:19][CH:18]=1 | Cc1ccc(Cl)nn1 | C[Si](C)(C)C#Cc1cccnc1 | null | [I-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | COCCOC | null | null | null | null | null | null | null | null | null | 80 | 12 | To the solution of 3-[(trimethylsilyl)ethynyl]pyridine (0.175g, 1.0 mmol), 3-chloro-6-methylpyridazine (0.128 g, 1.0 mmol), cupper (I) iodide (0.019 g, 0.1 mmol), triethylamine (0.202 g, 2.1 mmol), in 20 ml Ethylene glycol dimethyl ether was added tetrakis(triphenlyphosphine)palladium (0) (60 mg, 0.052 mmol). The resul... | Cc1ccc(C#Cc2cccnc2)nn1 | null | null | null |
1,082,805 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | [N+](C1C=CC(C([O:10][CH2:11][CH2:12][C:13]([CH3:26])([CH3:25])[CH2:14][CH:15]([O:21][N+:22]([O-:24])=[O:23])[CH2:16][O:17][N+:18]([O-:20])=[O:19])=O)=CC=1)([O-])=O.[OH-].[Na+]>C1COCC1.CCO.C(=O)(O)[O-].[Na+]>[N+:18]([O-:20])([O:17][CH2:16][CH:15]([O:21][N+:22]([O-:24])=[O:23])[CH2:14][C:13]([CH3:26])([CH3:25])[CH2:12][C... | CC(C)(CCOC(=O)c1ccc([N+](=O)[O-])cc1)CC(CO[N+](=O)[O-])O[N+](=O)[O-] | null | null | O=C([O-])O | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 3 | To a solution of 3,3-dimethyl-5,6-bis(nitrooxy)hexyl 4-nitrobenzoate (1.9 g, 4.73 mmol) in THF:EtOH 1:1 (12 ml) a aqueous solution of NaOH 3N (3.8 ml, 11.4 mmol) was added and the mixture was stirred at room temperature for 3 hrs. Then the mixture was diluted with a saturated solution of sodium bicarbonate and the prod... | CC(C)(CCO)CC(CO[N+](=O)[O-])O[N+](=O)[O-] | null | null | null |
387,928 | ord_dataset-44d518e567bd4c039d77233023f78bb2 | null | 1998-01-01T00:01:00 | true | [Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH3:22])[C:7](=[O:21])[C:8]3[CH:18]=[C:17]([CH2:19]Cl)[CH:16]=[N:15][C:9]=3[N:10]([CH2:13][CH3:14])[C:11]=2[N:12]=1.[OH:23][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH3:22])[C:7](=[O:21])[C:8]3[CH:18]=[C:17]([CH2:19][O:23][C:24]4[CH:25]=[N... | CCN1c2ncc(CCl)cc2C(=O)N(C)c2ccc(Cl)nc21 | Oc1cccnc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Using a procedure analogous to that described in Example 98, the title compound, m.p. 183°-184° C., was prepared from 2-chloro-8-chloromethyl-5,11-dihydro-11-ethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one and 3-hydroxypyridine. The yield was 72% of theory. | CCN1c2ncc(COc3cccnc3)cc2C(=O)N(C)c2ccc(Cl)nc21 | null | 72 | null |
829,923 | ord_dataset-47bd90bf5ec74fcd99ce250a56e18c8f | null | 2008-01-01T00:07:00 | true | [CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]([O:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][N:32]4[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]4)=[CH:25][CH:24]=3)=[C:13]3[C:18](=[CH:19][CH:20]=2)[CH:17]=[C:16]([OH:21])[CH:15]=[CH:14]3)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(N(CC)CC)C.[CH3:45][N:46]=[C:47]=[O:48... | CN=C=O | CS(=O)(=O)c1ccc(-c2ccc3cc(O)ccc3c2Oc2ccc(OCCN3CCCCC3)cc2)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 | null | 0.5 | Dissolve the compound of Example 3 (201 mg, 0.38 mmol) in dichloromethane (4 L) and add triethylamine (0.50 mL, 3.5 mmol) followed by methylisocyanate (500 mg, 8.7 mmol). After stirring for 30 minutes, pour the reaction mixture into saturated aqueous sodium bicarbonate and extract with dichloromethane. Dry the organic ... | CNC(=O)Oc1ccc2c(Oc3ccc(OCCN4CCCCC4)cc3)c(-c3ccc(S(C)(=O)=O)cc3)ccc2c1 | null | 59.5 | null |
986,770 | ord_dataset-35b56288528641309a040cc2b6710b61 | null | 2010-01-01T00:08:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([N:10]2[CH:18]([CH:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[CH:17]3[C:12]([C:13]4[CH:27]=[CH:26][C:25]([C:28]([OH:30])=[O:29])=[CH:24][C:14]=4[CH2:15][CH2:16]3)=[N:11]2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].[CH:31]1([CH2:37]O)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1>>[Cl:1][C:2]1[CH:3]=[C:4]([N:10]2[C... | OCC1CCCCC1 | N#Cc1ccc(N2N=C3c4ccc(C(=O)O)cc4CCC3C2C2CCCC2)cc1Cl | null | null | null | null | null | null | null | 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 (±)-(3SR,3aRS)-2-(3-chloro-4-cyanophenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylic acid, Example 15 and cyclohexylmethanol according to Method E (yellow solid, 165 mg, 0.320 mmol, 67% yield). ES-HRMS m/z calc. for C31H35ClN3O2 (M+H) 516.2412, found 516.2403... | N#Cc1ccc(N2N=C3c4ccc(C(=O)OCC5CCCCC5)cc4CCC3C2C2CCCC2)cc1Cl | null | 67 | null |
932,782 | ord_dataset-d8a5dc784dde4465894ec7c69d2e3ba6 | null | 2010-01-01T00:01:00 | true | [Cl:1][C:2]1[C:11]([S:12](Cl)(=[O:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C([O-])([O-])=O.[K+].[K+].[CH2:22]([NH2:24])[CH3:23]>C1C=CC=CC=1>[Cl:1][C:2]1[C:11]([S:12]([NH:24][CH2:22][CH3:23])(=[O:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5] | COC(=O)c1cccc(S(=O)(=O)Cl)c1Cl | CCN | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | To a solution of methyl 2-chloro-3-(chlorosulfonyl)benzoate (608 mg, 2.26 mmol) and K2CO3 (770 mg, 5.6 mmol) in 10 mL benzene was added ethylamine (5.6 mL, 11.2 mmol). Purification of the product provided methyl 2-chloro-3-[(ethylamino)sulfonyl]benzoate (335 mg, 53%) as a solid. 1H NMR (400 MHz, CDCl3), δ 8.24 (dd, 1H,... | CCNS(=O)(=O)c1cccc(C(=O)OC)c1Cl | null | 53.4 | null |
1,704,853 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | [O:1]=[S:2]1(=[O:13])[CH2:6][CH2:5][C:4]2[CH:7]=[C:8]([CH2:11][OH:12])[CH:9]=[CH:10][C:3]1=2.C(Cl)Cl>>[O:1]=[S:2]1(=[O:13])[CH2:6][CH2:5][C:4]2[CH:7]=[C:8]([CH2:11][O:12][S:2]([CH3:3])(=[O:13])=[O:1])[CH:9]=[CH:10][C:3]1=2 | O=S1(=O)CCc2cc(CO)ccc21 | null | 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 | 3 | To a solution of (1,1-Dioxo-2,3-dihydro-1H-1lambda*6*-benzo[b]thiophen-5-yl)-methanol (crude, 160 mg, 0.64 mmol) and triethylamne (180 ul, 1.29 mmol) in DCM (7 ml) Methanesulfonylchloride (60 ul, 0.77 mmol) was added at rt. The reaction mixture was stirred at it for 3 hours. | CS(=O)(=O)OCc1ccc2c(c1)CCS2(=O)=O | null | null | null |
32,982 | ord_dataset-8f61d01cf5b34e85a3ccc89f8901797b | null | 1977-01-01T00:11:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N:9]([CH2:17][C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:19])[CH2:10][CH2:11][N:12]([CH2:15][CH3:16])[CH2:13][CH3:14].[CH3:26][Mg]I>C(OCC)C>[CH2:15]([N:12]([CH2:13][CH3:14])[CH2:11][CH2:10][N:9]([CH2:17][C:18]([OH:19])([C:20]1[CH:21]=[CH:22][CH:23]=[CH:... | CCN(CC)CCN(CC(=O)c1ccccc1)c1cc(Cl)ccc1Cl | C[Mg]I | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 0.10 mole of 2-[N-(2,5-dichlorophenyl)-N-(β-diethylaminoethyl)amino]acetophenone in 200 ml of dry diethylether is added to a solution of 0.10 mole of methylmagnesium iodide in 500 ml of dry diethylether maintained at a temperature of from 0° to -5° C under nitrogen atmosphere. Thirty minutes after the add... | CCN(CC)CCN(CC(C)(O)c1ccccc1)c1cc(Cl)ccc1Cl | null | null | null |
249,738 | ord_dataset-4f3b2ca6df1d41ef8b5008f1f39da0e2 | null | 1992-01-01T00:06:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[CH2:6][NH:7][CH2:8][CH:9](O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CS(O)(=O)=O>ClCCl>[CH3:21][O:20][C:19]1[CH:18]=[C:17]2[C:5](=[CH:4][C:3]=1[O:2][CH3:1])[CH2:6][NH:7][CH2:8][CH:9]2[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1 | COc1ccc(CNCC(O)c2ccccc2)cc1OC | null | null | CS(=O)(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 8 | Add the amino-alcohol from step A (2.2 g) to a mixture of methanesulfonic acid (100 mL) and dichloromethane (150 mL) and stir overnight at room temperature. Pour the mixture into ice-water, separate and concentrate the organic layer to a residue. Triturate with benzene then recrystallize from ethanol to give 8.7 g of t... | COc1cc2c(cc1OC)C(c1ccccc1)CNC2 | null | 421.9 | null |
223,766 | ord_dataset-59f453c3a3d34a89bfd97b6b8b151908 | null | 1991-01-01T00:02:00 | true | [CH3:1][C:2]([CH3:6])=[CH:3][CH2:4][NH2:5].C[N:8](N=O)[C:9]([NH:11][N+:12]([O-:14])=[O:13])=N>CCO.O>[CH3:1][C:2]([CH3:6])=[CH:3][CH2:4][NH:5][C:9]([NH:11][N+:12]([O-:14])=[O:13])=[NH:8] | CC(C)=CCN | CN(N=O)C(=N)N[N+](=O)[O-] | 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 | 25 | 18 | 3-methyl-2-butenylamine (3.0 g) is added dropwise at room temperature to a slurry of 1-methyl-3-nitro-1 -nitrosoguanidine (4.3 g) in 50 ml of EtOH/H2O (1/1). After stirring the mixture at room temperature for 18 hours, the precipitate which forms is removed by filtration. The solid is then slurred with dilute hydrochlo... | CC(C)=CCNC(=N)N[N+](=O)[O-] | null | null | null |
850,047 | ord_dataset-171b840ae6e84e45bab43b987d09f5c7 | null | 2008-01-01T00:11:00 | true | I[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[N+:12]([O-:14])=[O:13].[C:15]1([S:21]([O-:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Na+]>CN(C)C=O>[N+:12]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[N:4]=[CH:3][C:2]([S:21]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:23])=[O:22])=[CH... | O=[N+]([O-])c1cccc2cc(I)cnc12 | O=S([O-])c1ccccc1 | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 65 | null | 3-Iodo-8-nitroquinoline (D3) (135 g, 0.45 mol), was suspended in dimethylformamide (2.4 L) in a 5 L 3-necked flask fitted with an overhead stirrer, under an argon atmosphere. This mixture was treated successively with anhydrous sodium phenylsulfinate (99.6 g 0.608 mol), and bis-(copper (I) triflate) benzene complex (17... | O=[N+]([O-])c1cccc2cc(S(=O)(=O)c3ccccc3)cnc12 | null | 57.6 | null |
567,013 | ord_dataset-5c8a417a8ba04cf0b7f78b9db9af1d01 | null | 2002-01-01T00:10:00 | true | [CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][C:4]=1[CH3:13].[Br:14]Br>C(O)(=O)C.[Cl-].[Na+].O>[Br:14][C:8]1[CH:7]=[C:6]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[C:4]([CH3:13])[C:3]=1[O:2][CH3:1] | COc1ccc(CC(=O)O)cc1C | BrBr | null | [Cl-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | To a solution of 4-methoxy-3-methylphenylacetic acid (0.43 g) in glacial acetic acid (7 mL) was added 0.2 mL of neat bromine carefully while stirring. The mixture was stirred in dark at ambient temperature for 27 h. The resulting mixture was diluted with brine, extracted with ethyl acetate, dried and concentrated in va... | COc1c(C)cc(CC(=O)O)cc1Br | null | null | null |
1,522,452 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH:10]=2)[N:3]=1.[F:20][C:21]1([F:33])[O:25][C:24]2[CH:26]=[CH:27][CH:28]=[C:29](B(O)O)[C:23]=2[O:22]1>>[F:33][C:21]1([F:20])[O:22][C:23]2[CH:29]=[CH:28][CH:27]=[C:26]([C:2]3[N:7]=[CH:6][N:5]=[C:4]([NH:8]... | CS(=O)(=O)Cc1cccc(Nc2ncnc(Cl)n2)c1 | OB(O)c1cccc2c1OC(F)(F)O2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Example 6 was prepared under similar conditions as described in the preparation of Example 1 using crude 4-chloro-N-{3-[(methylsulfonyl)methyl]phenyl}-1,3,5-triazin-2-amine and (2,2-difluoro-1,3-benzodioxol-4-yl)boronic acid (Aalen Chemical Co., Ltd.). The batch was purified by preparative HPLC: | CS(=O)(=O)Cc1cccc(Nc2ncnc(-c3cccc4c3OC(F)(F)O4)n2)c1 | null | null | null |
1,576,242 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([S:12]([NH:15][C:16]3[S:17][CH:18]=[CH:19][N:20]=3)(=[O:14])=[O:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:27]1([CH:33]2[CH2:37][CH2:36][NH:35][CH2:34]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C=O)C>[C:27]1([CH:33]2[CH2:37][CH2:36][N:35]([C:2]3[C:11]4[C:6... | O=S(=O)(Nc1nccs1)c1ccc2c(Cl)nccc2c1 | c1ccc(C2CCNC2)cc1 | 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 | 110 | 8 | 1-Chloro-N-(thiazol-2-yl)isoquinoline-6-sulfonamide (from Example 73, step 2; 0.050 g, 0.153 mmol) and potassium carbonate (0.106 g, 0.767 mmol) were dissolved in DMF (1.023 ml). 3-Phenyl-pyrrolidine (0.032 ml, 0.230 mmol) was added and the reaction was stirred overnight at 110° C. The reaction was filtered through a s... | O=S(=O)(Nc1nccs1)c1ccc2c(N3CCC(c4ccccc4)C3)nccc2c1 | null | null | null |
382,414 | ord_dataset-f367d8d2baac490b9204609a79420961 | null | 1997-01-01T00:11:00 | true | [C:1]([C:4]1[C:5]([O:16][CH3:17])=[CH:6][C:7]([O:14][CH3:15])=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10])(=[O:3])[CH3:2].[BH4-].[Na+].Cl>CO>[CH3:15][O:14][C:7]1[CH:6]=[C:5]([O:16][CH3:17])[C:4]([CH:1]([OH:3])[CH3:2])=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10] | COC(=O)c1cc(C(C)=O)c(OC)cc1OC | null | null | Cl | [BH4-] | [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 | 25 | 0.17 | A 1.00 g portion of methyl 5-acetyl-2,4-dimethoxybenzoate was dissolved in 10 ml of methanol, and 0.24 g of sodium borohydride was added in small portions. After 10 minutes of stirring at room temperature, 1N hydrochloric acid aqueous solution was added thereto, and the thus precipitated product of interest was collect... | COC(=O)c1cc(C(C)O)c(OC)cc1OC | null | null | null |
7,105 | ord_dataset-653be8036d754ce7b8a1c4cd419eaf55 | null | 1976-01-01T00:05:00 | true | C(N(CC)CC)C.[CH3:8][O:9][CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.[N+:16]([C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[C:21]([C:29]([F:32])([F:31])[F:30])[CH:20]=1)([O-:18])=[O:17]>C(Cl)Cl>[CH3:8][O:9][CH:10]1[CH2:15][CH2:14][N:13]([S:25]([C:22]2[CH:23]=[CH:24][C:19]([N+:16]([O-:18])=[O:17])=[CH:20]... | O=[N+]([O-])c1ccc(S(=O)(=O)Cl)c(C(F)(F)F)c1 | COC1CCNCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 2 | Triethylamine (1.0 g) and 4-methoxypiperidine (1.15 g) were added to a solution of 4-nitro-2-trifluoromethyl-benzene sulphonyl chloride (2.89 g) in methylene chloride (40 ml). The mixture was stirred at 25°C. for 2 hours and then evaporated to dryness in vacuo. The residual oil was triturated with 1:1 aqueous isopropan... | COC1CCN(S(=O)(=O)c2ccc([N+](=O)[O-])cc2C(F)(F)F)CC1 | null | null | null |
165,119 | ord_dataset-12ef86aced0149e0917be82ce22190e2 | null | 1987-01-01T00:11:00 | true | C[Si](C)(C)[O:3][C:4]1[N:13]=[C:12]([O:14][Si](C)(C)C)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.[Br:21][CH2:22][CH2:23][CH2:24]Br.C(=O)(O)[O-].[Na+]>>[Br:21][CH2:22][CH2:23][CH2:24][N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:12](=[O:14])[NH:13][C:4]1=[O:3] | BrCCCBr | C[Si](C)(C)Oc1nc(O[Si](C)(C)C)c2ccccc2n1 | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 25 | 2 | A mixture of 2,4-bis(trimethylsiloxy)-quinazoline (9.14 g) and 1,3-dibromopropane (30 g) was stirred for 2 hours at 130°-140° C. The reaction mixture was cooled at ambient temperature and a mixture of ice-water and saturated sodium bicarbonate aqueous solution was added to the reaction mixture and then the mixture was ... | O=c1[nH]c(=O)n(CCCBr)c2ccccc12 | null | 25.1 | null |
1,404,221 | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | null | 2014-01-01T00:03:00 | true | [C:1]([O:5][C:6]([N:8]1[CH:13]([C:14]2[NH:15][C:16]([C:19]3[CH:24]=[CH:23][C:22]([Br:25])=[CH:21][CH:20]=3)=[CH:17][N:18]=2)[CH:12]2[CH2:26][CH:9]1CC2)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O[C:32]([N:34]1C(C(=O)NCC(C2C=CC(Br)=CC=2)=O)C2CC1CC2)=O)(C)(C)C>>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:26]([C:32]#[N:34])[CH2:12][CH:13]1... | CC(C)(C)OC(=O)N1C2CCC(C2)C1C(=O)NCC(=O)c1ccc(Br)cc1 | CC(C)(C)OC(=O)N1C2CCC(C2)C1c1ncc(-c2ccc(Br)cc2)[nH]1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Title compound was prepared according to the method employed to prepare 3-[5-(4-Bromo-phenyl)-1H-imidazol-2-yl]-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (Example AS), and substituting 2-[2-(4-Bromo-phenyl)-2-oxo-ethylcarbamoyl]-4-cyano-pyrrolidine-1-carboxylic acid tert-butyl ester for 3-[2-(4-bro... | CC(C)(C)OC(=O)N1CC(C#N)CC1c1ncc(-c2ccc(Br)cc2)[nH]1 | null | null | null |
1,518,120 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | [F:1][C:2]1[CH:31]=[C:30]([N+:32]([O-])=O)[CH:29]=[CH:28][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[N:19]=[CH:18][C:17]([CH2:20][N:21]4[C:25](=[O:26])[CH2:24][CH2:23][C:22]4=[O:27])=[CH:16][CH:15]=3)[S:13][C:6]=12.[NH4+].[Cl-]>CO.O.[Zn]>[NH2:32][C:30]1[CH:29]=[CH:28][C:3]([O:4][C:5]2[CH:10]=[CH:... | O=C1CCC(=O)N1Cc1ccc(-c2cc3nccc(Oc4ccc([N+](=O)[O-])cc4F)c3s2)nc1 | null | null | [Cl-] | [NH4+] | [Zn] | 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 | null | To a suspension of 138 (100 mg, 0.209 mmol) in MeOH (10 mL) was added zinc (109 mg, 1.672 mmol) and NH4Cl (44.7 mg, 0.836 mmol) in water (1 mL) and the reaction mixture was heated to reflux for 48 hrs, cooled to RT and concentrated. The crude product was dissolved in MeOH/DCM and washed with water. The organic phase wa... | Nc1ccc(Oc2ccnc3cc(-c4ccc(CN5C(=O)CCC5=O)cn4)sc23)c(F)c1 | null | 85.4 | null |
182,340 | ord_dataset-f25e1b7f8ef54305a5170f5395a768c7 | null | 1989-01-01T00:01:00 | true | [K].[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.I[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][OH:25].C1OCCOCCOCCOCCOCCOC1>C1(C)C=CC=CC=1>[OH:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13]... | O=[N+]([O-])c1ccc(-c2ccc(O)cc2)cc1 | OCCCCCCI | null | C1COCCOCCOCCOCCOCCO1 | [K] | 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 500 ml of toluene in a one liter round bottom flask, fitted with a condenser and magnetic stirrer, are added 7.6 g (0.03M) of the potassium salt of 4-hydroxy-4'-nitrobiphenyl, 4.9 g (0.035M) of 6-iodo-1-hexanol, and 0.5 g of 18-crown-6 ether. The mixture is refluxed for about 20 hours until all of the potassium salt... | O=[N+]([O-])c1ccc(-c2ccc(OCCCCCCO)cc2)cc1 | null | null | null |
1,159,931 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | C[O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])(=[O:12])=[O:11])[CH2:7][N:6]1[C:20]1[S:21][C:22]([C:25]([F:28])([F:27])[F:26])=[N:23][N:24]=1)=[O:4].[OH-].[Li+]>>[Cl:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[S:10]([C@H:8]1[CH2:7][N:6]([C:20]2[S:21][C:22]([C:25]([... | COC(=O)[C@@H]1C[C@@H](S(=O)(=O)c2ccccc2Cl)CN1c1nnc(C(F)(F)F)s1 | null | null | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | In analogy to the procedure described in example 253e, (2S,4R)-4-(2-chloro-benzenesulfonyl)-1-(5-trifluoromethyl-[1,3,4]thiadiazol-2-yl)-pyrrolidine-2-carboxylic acid methyl ester was saponified in the presence of lithium hydroxide to give the title compound as yellow oil. MS (ESI): m/z=442.0 [M+H]+. | O=C(O)[C@@H]1C[C@@H](S(=O)(=O)c2ccccc2Cl)CN1c1nnc(C(F)(F)F)s1 | null | null | null |
1,544,734 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | N1(O[C:11]2[N:16]=[C:15]([NH:17][C:18]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:19]=3[CH:20]=[CH:21][N:22]4[CH3:27])[C:14]([C:28]([NH2:30])=[O:29])=[CH:13][N:12]=2)C2C=CC=CC=2N=N1.[NH2:31][C@@H:32]1[CH2:37][CH2:36][CH2:35][CH2:34][C@@H:33]1[NH:38]C(=O)OCCCC.CCN(C(C)C)C(C)C>>[NH2:31][C@H:32]1[CH2:37][CH2:36][CH2:35][CH2:34][C@H... | CCCCOC(=O)N[C@H]1CCCC[C@H]1N | Cn1ccc2c(Nc3nc(On4nnc5ccccc54)ncc3C(N)=O)cccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | null | 80 | null | To a solid of 2-(1H-benzo[d][1,2,3]triazol-1-yloxy)-4-(1-methyl-1H-indol-4-ylamino)pyrimidine-5-carboxamide (100 mg, 0.25 mmol) in vial was added ten butyl (1S,2R)-2-aminocyclohexylcarbamate (0.3 M solution in NMP, 1.25 mL, 0.375 mmol) and DIPEA (0.09 mL, 0.5 mmol). It was heated at 80° C. for 2 h, cooled and purified ... | Cn1ccc2c(Nc3nc(N[C@@H]4CCCC[C@@H]4N)ncc3C(N)=O)cccc21 | null | 22.1 | null |
52,507 | ord_dataset-3d470a6df4a04b1996e024a38c53e818 | null | 1979-01-01T00:03:00 | true | Cl[C:2]1[C:7](=[O:8])[C:6]([Cl:9])=[N:5][S:4][N:3]=1.[OH:10][C:11]1[CH:12]=[N:13][C:14]([CH3:17])=[CH:15][CH:16]=1.C(N(CC)CC)C>O1CCCC1>[Cl:9][C:6]1[C:7](=[O:8])[C:2]([O:10][C:11]2[CH:12]=[N:13][C:14]([CH3:17])=[CH:15][CH:16]=2)=[N:3][S:4][N:5]=1 | O=c1c(Cl)nsnc1Cl | Cc1ccc(O)cn1 | 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 | null | This compound was prepared in the manner of Example 3, using 14.6 grams (0.08 mole) of 3,5-dichloro-4H-1,2,6-thiadiazin-4-one, 8.7 grams (0.08 mole) of 3-hydroxy-6-methylpyridine and 8.9 grams (0.088 mole) of triethylamine in 300 ml of tetrahydrofuran. The crude product was recrystallized from ethanol to give 15.8 gram... | Cc1ccc(Oc2nsnc(Cl)c2=O)cn1 | null | 77.2 | null |
1,362,307 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | [CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:13]([CH2:15][CH2:16][O:17][CH2:18][C:19]([OH:21])=O)[CH3:14])(=[O:12])=[O:11])=[C:5]([CH3:22])[CH:4]=1.Cl.Cl.[N:25]1[CH:30]=[CH:29][C:28]([CH2:31][C:32]2([OH:38])[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)=[CH:27][CH:26]=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[OH:3... | COc1cc(C)c(S(=O)(=O)N(C)CCOCC(=O)O)c(C)c1 | OC1(Cc2ccncc2)CCNCC1 | null | Cl | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 25 | 1 | N,N′-Carbonyldiimidazole (77 mg, 0.475 mmol) was added to a solution of 2-(2-(4-methoxy-N,2,6-trimethylphenylsulfonamido)-ethoxy)acetic acid (acid unit S2) (150 mg, 0.453 mmol) in methylene chloride (7 ml), and the mixture was stirred for 1 h at room temperature. A solution of 4-(pyridin-4-ylmethyl)piperidin-4-ol dihyd... | COc1cc(C)c(S(=O)(=O)N(C)CCOCC(=O)N2CCC(O)(Cc3ccncc3)CC2)c(C)c1 | null | null | null |
1,038,728 | ord_dataset-3af92aec23dc4810b92eb0d8c60023ee | null | 2011-01-01T00:03:00 | true | [NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=2)[C:12]([O:14][CH3:15])=[O:13])[CH2:4]1.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][C:29]([C:32](O)=[O:33])=[CH:28][CH:27]=2)=[CH:22][CH:21]=1>>[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]2[CH:31]=[CH:30][C:29]([C:... | O=C(O)c1ccc(-c2ccc(Cl)cc2)cc1 | COC(=O)c1cccc(N2CCCC(CN)C2)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 | Using methyl 3-[3-(aminomethyl)piperidin-1-yl]benzoate (76.2 mg, 0.307 mmol) and 4′-chlorobiphenyl-4-carboxylic acid (77.2 mg, 0.332 mmol), the same procedure was followed as in Step 61e of Example 61 to give 117 mg (82%) of the desired compound as a pale yellow powder. | COC(=O)c1cccc(N2CCCC(CNC(=O)c3ccc(-c4ccc(Cl)cc4)cc3)C2)c1 | null | 82.3 | null |
986,728 | ord_dataset-35b56288528641309a040cc2b6710b61 | null | 2010-01-01T00:08:00 | true | [F:1][C:2]1[CH:24]=[CH:23][C:5]([CH:6]=[C:7]2[CH2:16][CH2:15][C:14]3[CH:13]=[C:12]([C:17]([O:19]CC)=[O:18])[CH:11]=[CH:10][C:9]=3[C:8]2=O)=[CH:4][CH:3]=1.[NH:25]([C:27]1[CH:28]=[C:29]2[C:34](=[CH:35][CH:36]=1)[C:33](=[O:37])[NH:32][CH2:31][CH2:30]2)[NH2:26].C(O)C.[O-]CC.[Na+]>CN(C)C=O>[F:1][C:2]1[CH:24]=[CH:23][C:5]([C... | CCOC(=O)c1ccc2c(c1)CCC(=Cc1ccc(F)cc1)C2=O | NNc1ccc2c(c1)CCNC2=O | null | CC[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | CN(C)C=O | null | null | null | null | null | null | null | null | null | 80 | null | To ethyl 6-(4-fluorobenzylidene)-5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate (Preparation 16; 303 mg, 1.07 mmol) and 6-hydrazinyl-3,4-dihydroisoquinolin-1(2H)-one (240 mg, 1.3 mmol) (U.S. Pat. No. 6,432,974, Kelly et al., Aug. 13, 2002, intermediate 2) was added ethanol (8 mL) and 21% sodium ethoxide in ethanol (... | O=C(O)c1ccc2c(c1)CCC1C2=NN(c2ccc3c(c2)CCNC3=O)C1c1ccc(F)cc1 | null | 63 | null |
748,979 | ord_dataset-844a22e1fcab44a5b59c5e2922b2855a | null | 2007-01-01T00:01:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[Cl:17])[CH2:5][N:6]1[CH2:11][CH2:10][O:9][CH:8]([CH2:12][NH2:13])[CH2:7]1.[N:18]([CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)=[C:19]=[O:20]>>[CH:21]1([NH:18][C:19]([NH:13][CH2:12][CH:8]2[O:9][CH2:10][CH2:11][N:6]([CH2:5][C:4]3[CH:14]=[CH:15][C:16]([Cl:17])=[C:2]([C... | O=C=NC1CCCCC1 | NCC1CN(Cc2ccc(Cl)c(Cl)c2)CCO1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Example 7 was prepared in an analogous manner to Example 1 using a mixture of Intermediate 3 (0.025 g) and isocyanatocyclohexane (17.4 μl) to give the title compound (0.0298 g). LC-MS (System A): Rt 2.26 mins, Mass Spectrum m/z 400 [MH+]. | O=C(NCC1CN(Cc2ccc(Cl)c(Cl)c2)CCO1)NC1CCCCC1 | null | null | null |
1,388,114 | ord_dataset-31641fb65b34430fa7435229b949b604 | null | 2014-01-01T00:01:00 | true | [CH:1]1([C:4]2[CH:13]=[C:12]3[C:7]([C:8](SC)=[N:9][C:10]([C:14]([F:23])([F:22])[C:15]4[CH:20]=[CH:19][C:18]([F:21])=[CH:17][N:16]=4)=[N:11]3)=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.ClC1C=C(C=CC=1)C(OO)=O.[CH3:37][C:38]1[NH:42][N:41]=[C:40]([NH2:43])[CH:39]=1>C(Cl)Cl.C1COCC1>[CH:1]1([C:4]2[CH:13]=[C:12]3[C:7]([C:8]([NH:43][C:40... | CSc1nc(C(F)(F)c2ccc(F)cn2)nc2cc(C3CC3)ccc12 | Cc1cc(N)n[nH]1 | null | O=C(OO)c1cccc(Cl)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | ClCCl | null | null | null | null | null | null | null | null | null | 0 | 0.33 | To 7-cyclopropyl-2-(difluoro(5-fluoropyridin-2-yl)methyl)-4-(methylthio)quinazoline from Step A (137 mg, 0.378 mmol) in DCM (5 mL) at 0° C. was added 70% meta-chloroperoxybenzoic acid (139 mg, 0.567 mmol). The mixture was stirred for at 0° C. for 20 min, then DCM (15 mL) was added and the mixture was washed with satura... | Cc1cc(Nc2nc(C(F)(F)c3ccc(F)cn3)nc3cc(C4CC4)ccc23)n[nH]1 | null | 7.7 | null |
876,131 | ord_dataset-e1c3af9b105b4af09a5171403bbfc06f | null | 2009-01-01T00:04:00 | true | [CH2:1]([N:8]1[CH2:14][CH:13]([CH3:15])[C:12](=[O:16])[NH:11][C:10]2[CH:17]=[N:18][C:19]([Cl:21])=[N:20][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[CH3:23].[H-].[Na+]>CN(C)C=O>[CH2:1]([N:8]1[CH2:14][CH:13]([CH3:15])[C:12](=[O:16])[N:11]([CH3:23])[C:10]2[CH:17]=[N:18][C:19]([Cl:21])=[N:20][C:9]1=2)[C:2]1[CH:3]=[... | CI | CC1CN(Cc2ccccc2)c2nc(Cl)ncc2NC1=O | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 0 | 2 | To an ice cooled mixture of 1.38 g (0.0046 mole) of (rac)-9-benzyl-2-chloro-7-methyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VI-42), 0.43 mL (0.0068 mole) of iodomethane and 15 mL of dimethylformamide was added 0.27 g (0.0068 mole) of a 60% oil dispersion of sodium hydride. The mixture was stirred at 0 d... | CC1CN(Cc2ccccc2)c2nc(Cl)ncc2N(C)C1=O | null | 93.3 | null |
1,325,220 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | [CH3:1][N:2]1[C:7](=[O:8])[C:6]([C:9]2[C:14]([CH2:15][CH3:16])=[CH:13][C:12]([CH2:17][CH3:18])=[CH:11][C:10]=2[CH2:19][CH3:20])=[C:5]([O:21][CH2:22]SC)[C:4]([CH3:25])=[N:3]1.S(Cl)([Cl:29])(=O)=O>C(Cl)(Cl)Cl>[Cl:29][CH2:22][O:21][C:5]1[C:4]([CH3:25])=[N:3][N:2]([CH3:1])[C:7](=[O:8])[C:6]=1[C:9]1[C:14]([CH2:15][CH3:16])=... | O=S(=O)(Cl)Cl | CCc1cc(CC)c(-c2c(OCSC)c(C)nn(C)c2=O)c(CC)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | 2.5 | To a mixture of 0.31 g of 2,6-dimethyl-5-methylthiomethoxy-4-(2,4,6-triethylphenyl)-3(2H)-pyridazinone [compound (I-2-2)] and 3 mL of chloroform, 0.08 mL of sulfuryl chloride was added, followed by stirring under ice cooling for 2.5 hours. The reaction mixture was concentrated under reduced pressure. The residue was su... | CCc1cc(CC)c(-c2c(OCCl)c(C)nn(C)c2=O)c(CC)c1 | null | null | null |
1,640,793 | ord_dataset-bcc0b01d4f58457a8733b10a099f43ba | null | 2015-01-01T00:10:00 | true | [CH3:1][C:2]1[N:3]=[N:4][N:5]([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:6]=1.[Li]CCCC.[C:31]([C:34]1[CH:39]=[CH:38][C:37]([S:40]([N:43]([C:48]2[CH:53]=[CH:52][C:51]([CH3:54])=[CH:50][C:49]=2[CH3:55])[CH2:44][CH:45... | CC(=O)c1ccc(S(=O)(=O)N(CC(C)C)c2ccc(C)cc2C)cc1 | Cc1nnn(C(c2ccccc2)(c2ccccc2)c2ccccc2)n1 | null | [Li]CCCC | 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 | -78 | 0.75 | To a solution of 5-methyl-2-trityl-2H-tetrazole (68.5 mg, 0.21 mmol) in tetrahydrofuran (THF) (1 mL) stirred under nitrogen at −70° C., was added a solution of n-BuLi (1.6 M in hexanes, 0.144 mL, 0.231 mmol) and tetrahydrofuran (THF) (1 mL) dropwise over 1 minute. The reaction mixture was stirred at −78° C. for 45 minu... | Cc1ccc(N(CC(C)C)S(=O)(=O)c2ccc(C(C)(O)Cc3nnn(C(c4ccccc4)(c4ccccc4)c4ccccc4)n3)cc2)c(C)c1 | null | 15.3 | null |
603,057 | ord_dataset-82e842e611ef4a05b6e7f9ea0a46d52d | null | 2003-01-01T00:07:00 | true | [CH:1]([O:4][C:5]([N:7]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([F:20])([F:19])[F:18])=[CH:14][CH:15]=2)[C@H:10]([NH2:21])[CH2:9][C@@H:8]1[CH2:22][CH3:23])=[O:6])([CH3:3])[CH3:2].[F:24][C:25]([F:39])([F:38])[C:26]1[CH:27]=[C:28]([CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=1)[CH:29]=O>>[CH:1]([O:4][C:5]([N:7]1[C:16]... | CC[C@H]1C[C@@H](N)c2cc(C(F)(F)F)ccc2N1C(=O)OC(C)C | O=Cc1cc(C(F)(F)F)cc(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 | treating said cis-4-amino-2-ethyl-6-trifluoromethyl-3,4,-dihydro-2H-quinoline-1-carboxylic acid isopropyl ester first with 3,5-bis-trifluoromethyl-benzaldehyde under acidic conditions followed by a reducing agent to form cis-4-(3,5-bis-trifluoromethyl-benzylamino)-2-ethyl-6-trifluoromethyl-3,4,-dihydro-2H-quinoline-1-c... | CC[C@H]1C[C@@H](NCc2cc(C(F)(F)F)cc(C(F)(F)F)c2)c2cc(C(F)(F)F)ccc2N1C(=O)OC(C)C | null | null | null |
1,269,641 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | [N:1]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([N:21]4[C:26](=[O:27])[CH:25]=[CH:24][CH:23]=[N:22]4)=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH2:5][CH2:4][C@@H:3]2[CH2:6][NH:7][CH2:8][C@H:2]12.[C:28]1(=O)[CH2:31][CH2:30][CH2:29]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[CH:28]1([N:7]2[CH2:6][C@@H:3]3[C@@H:2]... | O=c1cccnn1-c1ccc(-c2ccc(N3CC[C@@H]4CNC[C@@H]43)cc2)cc1 | O=C1CCC1 | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The product from Example 85B (0.033 g, 0.092 mmol), cyclobutanone (8.00 μL, 0.101 mmol), and sodium triacetoxyborohydride (0.025 g, 0.0.120 mmol) were processed as described in Example 85C to provide the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.91 (d, J=1.7 Hz, 1H), 7.63 (s, 4H), 7.50 (d, J=8.5 Hz, 2H), 7.23 (d,... | O=c1cccnn1-c1ccc(-c2ccc(N3CC[C@@H]4CN(C5CCC5)C[C@@H]43)cc2)cc1 | null | null | null |
611,050 | ord_dataset-73916d628db147c89020b3baac642d48 | null | 2003-01-01T00:09:00 | true | C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[S:12](=[O:14])(=[O:13])[CH2:11][CH2:10][C:9]([C:15]([O:17]C)=[O:16])=[CH:8][C:7]=2[CH:19]=1.Br>C(O)(=O)C>[OH:2][C:3]1[CH:4]=[CH:5][C:6]2[S:12](=[O:14])(=[O:13])[CH2:11][CH2:10][C:9]([C:15]([OH:17])=[O:16])=[CH:8][C:7]=2[CH:19]=1 | COC(=O)C1=Cc2cc(OC)ccc2S(=O)(=O)CC1 | null | null | Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of methyl 7-methoxy-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate (300 mg), 48% hydrobromic acid (3 ml) and acetic acid (3 ml) was heated at reflux for 4 hours. After concentration under reduced pressure, 48% hydrobromic acid (3 ml) and acetic acid (3 ml) were further added to the reaction mixture, whic... | O=C(O)C1=Cc2cc(O)ccc2S(=O)(=O)CC1 | null | 82.9 | null |
1,403,247 | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | null | 2014-01-01T00:03:00 | true | [NH2:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[O:12][CH:13]=[CH:14][CH:15]=3)[N:9]=2)[S:4][C:3]=1[C:16]([OH:18])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.Cl.[NH2:53][C:54]1[CH:55]=[C:56]([NH:61][C:62](=[O:74])[C:63]2[CH:68]=[CH:67][CH:66]=[C:65]([C:69]([C:72]#[N:73])([CH3:71])[CH3:... | Cc1ccc(NC(=O)c2cccc(C(C)(C)C#N)c2)cc1N | Nc1c(C(=O)O)sc2ncc(-c3ccco3)nc12 | null | CN(C)C(On1nnc2cccnc21)=[N+](C)C | Cl | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | CN(C)C=O | null | null | null | null | null | null | null | null | null | 80 | 8 | A solution of 7-amino-2-(furan-2-yl)thieno[2,3-b]pyrazine-6-carboxylic acid 59 (66 mg, 0.253 mmol), HATU (106 mg, 0.278 mmol) and DIPEA (0.104 mL, 0.632 mmol) in DMF (2 mL) was stirred at rt for 30 min. N-(3-amino-4-methylphenyl)-3-(2-cyanopropan-2-yl)benzamide hydrochloride 6 (83 mg, 0.253 mmol) was added and stirred ... | Cc1ccc(NC(=O)c2cccc(C(C)(C)C#N)c2)cc1NC(=O)c1sc2ncc(-c3ccco3)nc2c1N | null | 34.6 | null |
1,003,119 | ord_dataset-70899a0178cc441482746c093624afa0 | null | 2010-01-01T00:10:00 | true | [F:1][C:2]1[CH:3]=[C:4]([CH:33]=[CH:34][CH:35]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([NH:15][C:16]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][C:24]=4[O:26][C@@H:27]([CH3:32])[C:28](OC)=[O:29])[N:19]=[CH:18][N:17]=3)=[CH:12][CH:13]=2)[CH:8]=[N:7]1.[NH:36]1[CH2:40][CH2:39][CH2:38][CH2:37]1>>[F:1][C:2]1[CH:3]=[C:4]([CH:33... | COC(=O)[C@H](C)Oc1cccc2ncnc(Nc3ccc4c(cnn4Cc4cccc(F)c4)c3)c12 | C1CCNC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Using the same procedure as in Example 26, methyl (2S)-2-[(4-{[1-(3-fluorobenzyl)-1H-indazol-5-yl]amino}quinazolin-5-yl)oxy]propanoate (200 mg, 0.42 mmol) was reacted with pyrrolidine (0.35 ml, 4.2 mmol) to give the title compound as a solid (135 mg, 62%), except that the mixture was heated at 55° C. for 20 hours and p... | C[C@H](Oc1cccc2ncnc(Nc3ccc4c(cnn4Cc4cccc(F)c4)c3)c12)C(=O)N1CCCC1 | null | 63 | null |
1,685,047 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | [O:1]=[C:2]1[CH2:8][CH:7]2[N:9]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:4]([CH2:5][CH2:6]2)[CH2:3]1.C([N-]C(C)C)(C)C.[Li+].C([C:27]([O:29][CH3:30])=[O:28])#N>O1CCCC1>[O:1]=[C:2]1[CH2:3][CH:4]2[N:9]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:7]([CH2:6][CH2:5]2)[CH:8]1[C:27]([O:29][CH... | CC(C)(C)OC(=O)N1C2CCC1CC(=O)C2 | COC(=O)C#N | null | CC(C)[N-]C(C)C | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | 1 | Tetrahydrofuran (55.5 mL) was added to a flask containing tert-butyl 3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate (10 g, 0.0444 mol). At −78° C., lithium diisopropylamide (24.4 mL, 0.0488 mol) was added dropwise to the reaction. The reaction was allowed to stir for 1 hr, then methyl cyanoformate (4.226 mL, 0.05326 mol... | COC(=O)C1C(=O)CC2CCC1N2C(=O)OC(C)(C)C | null | 88 | null |
389,176 | ord_dataset-44d518e567bd4c039d77233023f78bb2 | null | 1998-01-01T00:01:00 | true | C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[N:8]2[CH:12]=[C:11]([CH2:13][CH2:14][CH2:15][O-:16])[N:10]=[CH:9]2)C=CC=CC=1.[Na+].C1(C)C=CC=CC=1.C1OCCOCCOCCOCCOC1.Cl[CH2:53][CH2:54][CH2:55][CH:56]1[CH2:61][CH2:60][CH2:59][CH2:58][CH2:57]1>C(OCC)C>[NH:8]1[CH:12]=[C:11]([CH2:13][CH2:14][CH2:15][O:16][CH2:53][CH2:54][CH2:55][CH:56]2[CH2:... | ClCCCC1CCCCC1 | [O-]CCCc1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cn1 | null | C1COCCOCCOCCOCCO1 | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | CCOCC | null | null | null | null | null | null | null | null | null | 75 | 24 | 5 mmol of sodium 3-[1-(triphenylmethyl)imidazol-4-yl]propoxide in 10 ml of toluene containing 0.5 mmol of 15-Crown-5 and 5 mmol of (3-chloropropyl)cyclohexane are mixed and the mixture is stirred for 24 h at 75° C. The suspension is concentrated under vacuum, the product obtained is dissolved in diethyl ether, the solu... | c1nc(CCCOCCCC2CCCCC2)c[nH]1 | null | null | null |
1,103,316 | ord_dataset-375a420ee9b042918ddca20f02df37d3 | null | 2011-01-01T00:11:00 | true | Br[C:2]1[N:6]([S:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:5]=[C:4]([CH2:16][N:17]([CH3:25])[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[C:3]=1[CH:26]([CH3:28])[CH3:27].[C:29]1(B(O)O)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=... | OB(O)c1ccccc1 | CC(C)c1c(CN(C)C(=O)OC(C)(C)C)cn(S(=O)(=O)c2ccccc2)c1Br | 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 | null | null | null | null | null | null | null | null | null | null | null | null | null | Using tert-butyl {[5-bromo-4-isopropyl-1-(phenylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (596 mg), phenylboronic acid (307 mg), tetrakis(triphenylphosphine)palladium (218 mg) and sodium carbonate (401 mg), a procedure as in Reference Example 56 was performed to give the title compound as a pale-red oil (yield 21... | CC(C)c1c(CN(C)C(=O)OC(C)(C)C)cn(S(=O)(=O)c2ccccc2)c1-c1ccccc1 | null | 36.8 | null |
557,191 | ord_dataset-f483e698250b4da0a84f425c7bfa965a | null | 2002-01-01T00:08:00 | true | F[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH2:6][CH2:5]2.[NH2:13][NH2:14]>O1CCOCC1>[NH:13]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH2:6][CH2:5]2)[NH2:14] | O=C1NCCc2cc(F)ccc21 | NN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 6-fluoro-3,4-dihydro-2H-isoquinolin-1-one (3.6 g, 0.022 mole) and hydrazine (17.3 mL, 0.55 mole) was stirred at reflux in dioxane (150 mL) under nitrogen for 48 hours. The reaction mixture was concentrated under vacuo, water added (150 mL), and the product isolated by filtration. The product was thoroughl... | NNc1ccc2c(c1)CCNC2=O | null | null | null |
464,957 | ord_dataset-6c36eb0f817d4144988b8963c5d58879 | null | 2000-01-01T00:05:00 | true | [CH2:1]([N:5]1[C:9]2=[C:10](Cl)[N:11]=[N:12][CH:13]=[C:8]2[C:7]([CH3:15])=[C:6]1[CH3:16])[CH:2]=[CH:3][CH3:4].[F:17][C:18]1[CH:19]=[C:20]([CH:23]=[C:24]([F:26])[CH:25]=1)[CH2:21][OH:22]>>[CH2:1]([N:5]1[C:9]2=[C:10]([O:22][CH2:21][C:20]3[CH:19]=[C:18]([F:17])[CH:25]=[C:24]([F:26])[CH:23]=3)[N:11]=[N:12][CH:13]=[C:8]2[C:... | OCc1cc(F)cc(F)c1 | CC=CCn1c(C)c(C)c2cnnc(Cl)c21 | null | null | null | null | null | null | null | 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 (cis/trans=29/71) was prepared as a white powder in 41.6% yield in a similar procedure to that described in Example 1 by using 1-(2-butenyl)-7-chloro-2,3-dimethylpyrrolo[2,3-d]pyridazine (cis/trans=24/76) and 3,5-difluorobenzyl alcohol. | CC=CCn1c(C)c(C)c2cnnc(OCc3cc(F)cc(F)c3)c21 | null | 41.6 | null |
166,833 | ord_dataset-5c25f386f4664070a72d578feacedf86 | null | 1987-01-01T00:12:00 | true | [CH3:1][C:2]1([CH3:10])[CH2:6][CH2:5][C:4]([CH3:8])([CH3:7])[CH:3]1[OH:9].N1C=CC=CC=1.[CH3:17][S:18](Cl)(=[O:20])=[O:19].C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH3:17][S:18]([O:9][CH:3]1[C:4]([CH3:8])([CH3:7])[CH2:5][CH2:6][C:2]1([CH3:10])[CH3:1])(=[O:20])=[O:19] | CC1(C)CCC(C)(C)C1O | CS(=O)(=O)Cl | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | c1ccncc1 | null | null | null | null | null | null | null | null | null | 25 | 12 | 2.84 g of 2,2,5,5-tetramethylcyclopentanol and 3.2 ml of pyridine were dissolved in 20 ml of methylene chloride, and 4.5 g of methanesulfonyl chloride was added thereto. The mixture was stirred at room temperature for 12 hours, and then 50 ml of aqueous saturated sodium hydrogen carbonate solution was added thereto. Th... | CC1(C)CCC(C)(C)C1OS(C)(=O)=O | null | 28.6 | null |
1,472,071 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | [CH:1]1([N:7]2[C:12]([OH:13])=[C:11]([C:14]([NH:16][CH2:17][C:18]([O:20]CC)=[O:19])=[O:15])[C:10](=[O:23])[NH:9][C:8]2=[O:24])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[Br:31][C:32]1[CH:39]=[CH:38][CH:37]=[CH:36][C:33]=1[CH2:34]Br.Cl>CC(N(C)C)=O>[Br:31][C:32]1[CH:39]=[CH:38][CH:37]=[CH:36][C:33]=1[... | CCOC(=O)CNC(=O)c1c(O)n(C2CCCCC2)c(=O)[nH]c1=O | BrCc1ccccc1Br | null | Cl | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)N(C)C | null | null | null | null | null | null | null | null | null | null | null | 8 | A mixture of ethyl N-[(1-cyclohexyl-6-hydroxy-2,4-dioxo-1,2,3,4-tetrahydro-5-pyrimidinyl)carbonyl]glycinate (340 mg, 1.0 mmoles), pulv. potassium carbonate (750 mg, 5.35 mmoles) and 2-bromobenzyl bromide (480 mg, 1.92 mmoles) in dimethylacetamide (6 mL) was vigorously stirred at 100° C. for 3 hours. The mixture was pou... | O=C(O)CNC(=O)c1c(O)n(C2CCCCC2)c(=O)n(Cc2ccccc2Br)c1=O | null | 31.2 | null |
1,126,118 | ord_dataset-285df12e34cd46e993e3c8ebc3a8962a | null | 2012-01-01T00:01:00 | true | P(Br)(Br)[Br:2].[CH2:5]([O:12][C:13](=[O:24])[NH:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21]O)=[CH:17][C:16]=1[F:23])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CCOCC>[CH2:5]([O:12][C:13](=[O:24])[NH:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][Br:2])=[CH:17][C:16]=1[F:23])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1 | BrP(Br)Br | O=C(Nc1ccc(CO)cc1F)OCc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | null | null | null | null | null | null | null | null | null | null | 25 | 0.75 | Phosphorous tribromide (20.9 mL, 218 mmol) was added to diethylether (700 mL) at 0° C. To the PBr3 solution was added dropwise (2-fluoro-4-hydroxymethyl-phenyl)-carbamic acid benzyl ester (36.5 g, 133 mmol) in Et2O (400 mL) at 0° C. over 1 h. The reaction mixture was stirred at room temperature for 45 min and was caref... | O=C(Nc1ccc(CBr)cc1F)OCc1ccccc1 | null | null | null |
170,142 | ord_dataset-37d3220f708c49ad839bab296b722248 | null | 1988-01-01T00:03:00 | true | [C:1]([OH:22])(=[O:21])[CH2:2][CH2:3][CH2:4][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]CC>C(Cl)(Cl)Cl>[C:1]([OH:22])(=[O:21])[CH2:2][CH2:3][CH2:4][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][CH3:18] | CCCCCCCCCCCCCCCCCCCC(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | Subsequently, a solution (0.5 ml) of arachidic acid (1×10-3 mol/l) in chloroform was spread on the aforesaid aqueous phase. After removal of chloroform from the surface of the aqueous phase by evaporation, the surface pressure of the aqueous phase was adjusted to 30 dyne/cm, and a film of stearic acid was formed thereo... | CCCCCCCCCCCCCCCCCC(=O)O | null | null | null |
1,177,768 | ord_dataset-0f9d2dbe929a45c3892ae75e81e99443 | null | 2012-01-01T00:06:00 | true | F[C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([C:14]([CH2:17][O:18][C:19]4[C:28]5[C:23](=[CH:24][C:25]([O:29][CH3:30])=[CH:26][CH:27]=5)[N:22]=[CH:21][CH:20]=4)=[N:15][N:16]=3)[N:13]=2)=[CH:4][CH:3]=1.[NH2:31][CH:32]1[CH2:36][CH2:35][N:34]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:33]1.C... | CC(C)(C)OC(=O)N1CCC(N)C1 | COc1ccc2c(OCc3nnc4ccc(-c5ccc(F)nc5)nn34)ccnc2c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CS(C)=O | null | null | null | null | null | null | null | null | null | null | 1 | A 0.5-2 mL microwave vial was charged with 4-((6-(6-fluoropyridin-3-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methoxy)-7-methoxyquinoline (0.100 g, 0.249 mmol), tert-butyl 3-aminopyrrolidine-1-carboxylate (0.116 g, 0.622 mmol), and DMSO (4.00 ml, 56.4 mmol), sealed and placed in a Personal Chemistry microwave for 1 hour... | COc1ccc2c(OCc3nnc4ccc(-c5ccc(NC6CCN(C(=O)OC(C)(C)C)C6)nc5)nn34)ccnc2c1 | null | null | null |
909,173 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | Br[CH:2]1[CH:6]([Br:7])[C:5]2[CH:8]=[C:9]([CH:12]=[O:13])[CH:10]=[CH:11][C:4]=2[O:3]1.[OH-].[K+]>C(O)C.O>[Br:7][C:6]1[C:5]2[CH:8]=[C:9]([CH:12]=[O:13])[CH:10]=[CH:11][C:4]=2[O:3][CH:2]=1 | O=Cc1ccc2c(c1)C(Br)C(Br)O2 | null | null | [K+] | [OH-] | 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 | 70 | null | To a solution of 2,3-dibromo-2,3-dihydro-1-benzofuran-5-carbaldehyde (10 g) in dry ethanol (25 mL) was added a solution of KOH in dry ethanol (14 mL) and refluxed at 70° C. for 2 h. The reaction mixture was cooled, diluted with water and extracted with EtOAc (3×50 mL). The organic layer was washed with water, brine and... | O=Cc1ccc2occ(Br)c2c1 | null | 44.9 | null |
82,587 | ord_dataset-b1023e5ccd7142de9d250aa2e3e124db | null | 1981-01-01T00:06:00 | true | C([NH:8][C@H:9]([C:17]([C:19]1([NH2:33])[CH:26]2[CH2:27][CH:22]3[CH2:23][CH:24]([CH2:28][C:20]1([C:29]([O:31][CH3:32])=[O:30])[CH2:21]3)[CH2:25]2)=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(OC(C)(C)C)=O.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:8][C@H:9]([C:17]([C:19]1([NH2:33])[CH:26]2[CH2:25][CH:24]3[CH2:23][CH... | COC(=O)C12CC3CC(CC(C3)C1(N)C(=O)[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C)C2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | null | null | To a solution of 1.862 g of methyl Boc-L-phenylalanyl-2-amino-1-adamantanecarboxylate (Isomer A) in 10 ml of methylene chloride is added 5 ml of trifluoracetic acid. After 15 minutes at room temperature the reaction mixture is concentrated to a small volume and 5 ml of cold potassium carbonate is added. The mixture is ... | COC(=O)C12CC3CC(CC(C3)C1(N)C(=O)[C@@H](N)Cc1ccccc1)C2 | null | null | null |
1,206,621 | ord_dataset-fb72428f30234761b4216139dc228d0c | null | 2012-01-01T00:09:00 | true | [C:1]([N:8]([CH3:42])[CH:9]1[CH2:14][CH2:13][CH:12]([N:15]([CH2:30][C:31]2[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][C:36]=2[O:37][CH3:38])[C:16]([C:18]2[S:22][C:21]3[C:23]([F:28])=[CH:24][CH:25]=[C:26]([F:27])[C:20]=3[C:19]=2[Cl:29])=[O:17])[CH2:11][CH2:10]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Br[C:44]1[CH:49]=[CH:4... | Brc1ccccn1 | COc1ccc(B(O)O)cc1CN(C(=O)c1sc2c(F)ccc(F)c2c1Cl)C1CCC(N(C)C(=O)OC(C)(C)C)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 | Boronic acid 9 (500 mg, 0.80 mmol) is coupled to 2-bromopyridine (77 μL, 0.80 mmol) using Method B to give the title compound. | COc1ccc(-c2ccccn2)cc1CN(C(=O)c1sc2c(F)ccc(F)c2c1Cl)C1CCC(N(C)C(=O)OC(C)(C)C)CC1 | null | null | null |
306,987 | ord_dataset-a6643d22de674f30a85ba57198b82644 | null | 1995-01-01T00:03:00 | true | [Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[C:3]=1[Cl:14].[O-:15]O>>[Cl:1][C:2]1[C:3]([Cl:14])=[C:4]([N+:11]([O-:13])=[O:12])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[C:7]=1[OH:15] | [O-]O | O=[N+]([O-])c1cc(Cl)c(Cl)c([N+](=O)[O-])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 | contacting 1,2-dichloro-3,5-dinitrobenzene with a hydroperoxide in the presence of anhydrous base to form 2,3-dichloro-4,6-dinitrophenol; | O=[N+]([O-])c1cc([N+](=O)[O-])c(Cl)c(Cl)c1O | null | null | null |
1,181,427 | ord_dataset-0f9d2dbe929a45c3892ae75e81e99443 | null | 2012-01-01T00:06:00 | true | [F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[O:11][C:12]1[CH:29]=[CH:28][C:15]2[CH2:16][CH2:17][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:19][CH2:20][C:14]=2[CH:13]=1>C(O)C.[Pd]>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([O:11][C:12]2[CH:29]=[CH:28][C:15]3[CH2:16][CH2:17][N:18]([C:21]([O:23... | CC(C)(C)OC(=O)N1CCc2ccc(Oc3ccc([N+](=O)[O-])cc3F)cc2CC1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 25 | 3 | To a solution of 1,1-dimethylethyl 7-[(2-fluoro-4-nitrophenyl)oxy]-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (E274, Step 1) (1.37 g, 3.40 mmol) in ethanol (25 ml) was added palladium on charcoal (10 wt % palladium) (300 mg) and the reaction was stirred at room temperature under hydrogen (1 atmosphere) for 3 hou... | CC(C)(C)OC(=O)N1CCc2ccc(Oc3ccc(N)cc3F)cc2CC1 | null | null | null |
292,080 | ord_dataset-6c3ec086c8c9475e8d31a44641b49e02 | null | 1994-01-01T00:06:00 | true | [I-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH2:22]([Li])[CH2:23][CH2:24][CH3:25].[CH:27]([C:29]1[CH:30]=[C:31](C=CC=1)[C:32]([O:34][CH3:35])=[O:33])=O>O1CCCC1.CCCCCC>[CH:24]([C:23]1[CH:22]=[C:31]([CH:30]=[CH:29][CH:27]=1)[C:32]([O:34][CH3:35])=[O:33])=[CH2:25] | [Li]CCCC | COC(=O)c1cccc(C=O)c1 | null | C[P+](c1ccccc1)(c1ccccc1)c1ccccc1 | [I-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCCCCC | null | null | null | null | null | null | null | null | null | -50 | 8 | To a stirred suspension of 590 mg of methyl triphenylphosphonium iodide in 50 ml of dry tetrahydrofuran cooled to -50° C. was added dropwise 5.3 ml of 2.5M n-butyl lithium in hexane. The resulting mixture was allowed to warm to 0° C. over a period of one hour. The mixture was then cooled to -70° C. and 2.0 g of methyl ... | C=Cc1cccc(C(=O)OC)c1 | null | null | null |
1,274,580 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | [NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH2:10][C:11]([O:13][CH3:14])=[O:12])=[N:2]1.[CH2:15]1[CH2:20][O:19][CH:18]=[CH:17][CH2:16]1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C(#N)C>[O:19]1[CH2:20][CH2:15][CH2:16][CH2:17][CH:18]1[N:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH2:10][C:11]([O:13][CH3:14])=[O:12... | C1=COCCC1 | COC(=O)Cc1n[nH]c2ncccc12 | null | N#CC1=C(C#N)C(=O)C(Cl)=C(Cl)C1=O | 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 | 75 | null | To a solution of methyl 1H-pyrazolo[3,4-b]pyridin-3-ylacetate (84 mg, 0.439 mmol) in acetonitrile (3 mL) was added DHP (37 mg, 0.439 mmol) and DDQ (10 mg, 0.044 mmol). This mixture was heated to 75° C. for 20 minutes. After this time, additional DHP (37 μL, 0.44 mmol) was added and the reaction mixture heated to 85° C.... | COC(=O)Cc1nn(C2CCCCO2)c2ncccc12 | null | null | null |
1,320,110 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | [OH-].[Na+:2].[C:3]1([C:9]2[CH:10]=[C:11]([C:15]([NH:17][C:18]3[CH:26]=[C:25]([C:27]4[S:28][CH:29]=[CH:30][CH:31]=4)[CH:24]=[CH:23][C:19]=3[C:20]([OH:22])=[O:21])=[O:16])[CH:12]=[N:13][CH:14]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C(O)C>[C:3]1([C:9]2[CH:10]=[C:11]([C:15]([NH:17][C:18]3[CH:26]=[C:25]([C:27]4[S:28][CH:29]=... | O=C(Nc1cc(-c2cccs2)ccc1C(=O)O)c1cncc(-c2ccccc2)c1 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | 0.5 | A 1 mol/L aqueous solution of sodium hydroxide (0.13 mL) was added to an ethanol (4.0 mL) suspension of the obtained 2-(5-phenylpyridine-3-carboxamido)-4-(thiophen-2-yl)benzoic acid (54 mg) at room temperature, followed by stirring at the same temperature for 2 hours and 30 minutes. The solvent was evaporated under red... | O=C(Nc1cc(-c2cccs2)ccc1C(=O)[O-])c1cncc(-c2ccccc2)c1 | null | null | null |
1,569,391 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | [N+:1]([C:4]1[CH:5]=[N:6][N:7]([CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[CH:8]=1)([O-:3])=[O:2].C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[Cl:27]C(Cl)(Cl)C(Cl)(Cl)Cl>C1COCC1>[Cl:27][C:8]1[N:7]([CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[N:6]=[CH:5][C:4]=1[N+:1]([O-:3])=[O:2] | ClC(Cl)(Cl)C(Cl)(Cl)Cl | C[Si](C)(C)CCOCn1cc([N+](=O)[O-])cn1 | null | C[Si](C)(C)[N-][Si](C)(C)C | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | -78 | 0.5 | In an oven-dried flask, 4-nitro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole (412.4 mg, 1.695 mmol) was dissolved in 5 mL THF and cooled at −78° C. To this solution was slowly added 1.0M Lithium hexamethyldisilazide in tetrahydrofuran (2.0 mL, 2.0 mmol). After stirring for 30 minutes at −78° C., a solution of hexac... | C[Si](C)(C)CCOCn1ncc([N+](=O)[O-])c1Cl | null | 97.5 | null |
842,778 | ord_dataset-e2b35e721c2741999b0005d12691f9fe | null | 2008-01-01T00:10:00 | true | [O:1]1[CH2:6][CH2:5][CH:4]([NH:7][NH:8]C(OC(C)(C)C)=O)[CH2:3][CH2:2]1.FC(F)(F)C(O)=O.F[C:24]1[C:29]([C:30](=O)[CH2:31][CH3:32])=[CH:28][CH:27]=[C:26]([F:34])[N:25]=1>ClCCl>[CH2:31]([C:30]1[C:29]2[C:24](=[N:25][C:26]([F:34])=[CH:27][CH:28]=2)[N:7]([CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)[N:8]=1)[CH3:32] | CCC(=O)c1ccc(F)nc1F | CC(C)(C)OC(=O)NNC1CCOCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | 75 | 72 | A mixture of tert-butyl 2-(tetrahydro-2H-pyran-4-yl)hydrazinecarboxylate (3.8 g, 0.018 mol) and trifluoroacetic acid (20 mL, 0.3 mol) were stirred in dichloromethane (20 mL) for 90 minutes. The mixture was concentrated, and the residue was taken up in acetonitrile (30 mL). 1-(2,6-difluoropyridin-3-yl)propan-1-one (2.34... | CCc1nn(C2CCOCC2)c2nc(F)ccc12 | null | 83.7 | null |
719,060 | ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | null | 2006-01-01T00:07:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][C@H:15]1[CH2:17][O:16]1)[N:9]=[CH:8][N:7]=[C:6]2[O:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][CH:23]=[C:22]2[CH3:28].[NH:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1>CN(C=O)C>[OH:16][C@H:15]([CH2:17][N:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1)[CH... | C1CCNC1 | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H]1CO1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 60 | 24 | A mixture of (2R)-6-methoxy-4-(3-methylindol-5-yloxy)-7-(oxiran-2-ylmethoxy)quinazoline (300 mg, 0.65 mmol), (prepared as described in Example 278), and pyrrolidine (0.17 ml, 2.04 mmol) in DMF (5 ml) was stirred at 60° C. for 24 hours and allowed to cool to ambient temperature. The solvents were removed in vacuo and th... | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H](O)CN1CCCC1 | null | 88.2 | null |
846,513 | ord_dataset-e2b35e721c2741999b0005d12691f9fe | null | 2008-01-01T00:10:00 | true | [Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][NH:9]2)=[CH:4][CH:3]=1.[CH:12]([O:15][C:16]1[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][C:17]=1[C:18](O)=[O:19])([CH3:14])[CH3:13]>>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][N:9]2[C:18]([C:17]2[CH:21]=[C:22]([S:25]([CH3:28])(=[O:27]... | CC(C)Oc1ccc(S(C)(=O)=O)cc1C(=O)O | Clc1ccc2c(c1)NCCC2 | null | null | null | null | null | null | null | 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 in analogy to example 1.1 from 7-chloro-1,2,3,4-tetrahydro-quinoline (CA [90562-35-9]) and 2-isopropoxy-5-methanesulfonyl-benzoic acid (Example 2.1). | CC(C)Oc1ccc(S(C)(=O)=O)cc1C(=O)N1CCCc2ccc(Cl)cc21 | null | null | null |
1,697,753 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | [Cl:1][C:2]1[C:3]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([P:33]([CH3:36])([CH3:35])=[O:34])=[CH:29][C:28]=2[S:37]([CH:40]([CH3:42])[CH3:41])(=[O:39])=[O:38])=[N:4][C:5]([NH:8][C:9]2SC(N3CCN(C4C=CC=CN=4)CC3)=NN=2)=[N:6][CH:7]=1.C(N)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>>[CH2:9]([NH:8][C:5]1[N:4]=[C:3]([NH:26][C:27... | CC(C)S(=O)(=O)c1cc(P(C)(C)=O)ccc1Nc1nc(Nc2nnc(N3CCN(c4ccccn4)CC3)s2)ncc1Cl | NCc1ccccc1 | null | null | null | null | null | null | null | 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 can be prepared as in Example 32 by reacting 2,5-dichloro-N-[4-(dimethylphosphoryl)-2-(propan-2-ylsulfonyl)phenyl]pyrimidin-4-amine (as described in Example 53) with benzylamine. | CC(C)S(=O)(=O)c1cc(P(C)(C)=O)ccc1Nc1nc(NCc2ccccc2)ncc1Cl | null | null | null |
416,473 | ord_dataset-1cb9d78632144c5f8acfc3e9ff388678 | null | 1998-01-01T00:11:00 | true | [CH2:1]([N:8]1[C:13](=[O:14])[C:12]([CH:15]([CH3:17])[CH3:16])=[C:11]([Cl:18])[NH:10][C:9]1=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:27][CH2:28][CH2:29][Cl:30]>CN(C)C=O>[CH2:1]([N:8]1[C:13](=[O:14])[C:12]([CH:15]([CH3:16])[CH3:17])=[C:11]([Cl:18])[N:10]([CH2:27][CH2:28][CH2:29][C... | ClCCCBr | CC(C)c1c(Cl)[nH]c(=O)n(Cc2ccccc2)c1=O | 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 | 90 | 2 | To a suspension of 20.91 g (75 mmol) of 3-benzyl-6-chloro-5-isopropylpyrimidine-2,4(1H,3H)-dione and 16.58 g (120 mmol) of potassium carbonate in 120 ml of N,N-dimethylformamide, 14.8 ml (150 mmol) of 1-bromo-3-chloropropane was added at room temperature. This mixture was stirred at 90° C. for 2 hours. After cooling, t... | CC(C)c1c(Cl)n(CCCCl)c(=O)n(Cc2ccccc2)c1=O | null | null | null |
878,837 | ord_dataset-3592bd645cd143ee8274cd0d834ae581 | null | 2009-01-01T00:05:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][N:10]([C:19]([NH:21][S:22]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)(=[O:24])=[O:23])=O)[N:9]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)(Cl)Cl.[NH2:38][N:39]1[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1>ClC1C=CC=CC=1>[C... | O=C(NS(=O)(=O)c1ccc(Cl)cc1)N1CC(c2ccccc2)C(c2ccc(Cl)cc2)=N1 | NN1CCCCC1 | null | ClP(Cl)(Cl)(Cl)Cl | 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 | 25 | 16 | Part B: A mixture of 3-(4-chlorophenyl)-N-((4-chlorophenyl)sulfonyl)-4-phenyl-4,5-dihydro-1H-pyrazole-1-carboxamide (1.42 gram, 3.00 mmol) and phosphorus pentachloride (PCl5) (0.63 gram, 3.03 mmol) in chlorobenzene (15 mL) is heated at reflux temperature for 1 hour. After thorough concentration in vacuo, the formed 3-(... | O=S(=O)(N=C(NN1CCCCC1)N1CC(c2ccccc2)C(c2ccc(Cl)cc2)=N1)c1ccc(Cl)cc1 | null | 34.1 | null |
377,217 | ord_dataset-846d411edee44814931e062174d7ef12 | null | 1997-01-01T00:09:00 | true | [CH2:1]([N:4]([CH2:9][CH:10]=[CH2:11])[CH2:5][C:6]([OH:8])=O)[CH:2]=[CH2:3].C(N1C=CN=C1)(N1C=CN=C1)=O.[F:24][C:25]1[CH:26]=[CH:27][C:28]2[N:34]3[CH:35]=[N:36][C:37]([C:38](=[N:40]O)[NH2:39])=[C:33]3[C@@H:32]3[CH2:42][CH2:43][N:31]3[C:30](=[O:44])[C:29]=2[CH:45]=1>CN(C)C=O>[CH2:9]([N:4]([CH2:5][C:6]1[O:8][N:40]=[C:38]([... | C=CCN(CC=C)CC(=O)O | NC(=NO)c1ncn2c1[C@@H]1CCN1C(=O)c1cc(F)ccc1-2 | null | O=C(n1ccnc1)n1ccnc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | 2 | 2.32 g (15 mmol) of diallylglycine were dissolved in 15 ml of N,N-dimethylformamide and treated with 2.75 g (17 mmol) of 1,1'-carbonyldiimidazole. After stirring at 50° C. for 20 minutes 3.01 (10 mmol) of (S)-7-fluoro-12,12a-dihydro-9-oxo-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxamidoxime were added... | C=CCN(CC=C)Cc1nc(-c2ncn3c2[C@@H]2CCN2C(=O)c2cc(F)ccc2-3)no1 | null | 37 | null |
14,888 | ord_dataset-b971427c0b944c56b63bb2356fa8ca69 | null | 1976-01-01T00:11:00 | true | C(C=C([NH:9][C@@H:10]1[C:35](=[O:36])[N:12]2[C@@H:13]([C:19]([O:21][CH:22]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])[C@@:14]([Cl:18])([CH3:17])[CH2:15][S:16][C@H:11]12)C)(OCC)=O.Cl>C(Cl)(Cl)Cl.CC(C)=O>[NH2:9][C@@H:10]1[C:35](=[O:36])[N:12]2[C@@H:13]([C:19]([O... | CCOC(=O)C=C(C)N[C@@H]1C(=O)N2[C@@H]1SC[C@@](C)(Cl)[C@@H]2C(=O)OC(c1ccccc1)c1ccccc1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | 25 | 1 | A solution of benzhydryl 7β-(1-carbethoxy-1-propen-2-ylamino)-3β-chloro-3α-methylcepham-4α-carboxylate (107 mg) and 1N hydrochloric acid (0.1 ml) in a mixture of chloroform and acetone (1:1; 2 ml) is stirred at room temperature for 1 hour. The reaction mixture is washed with water, dried, and evaporated to remove the s... | C[C@@]1(Cl)CS[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)OC(c1ccccc1)c1ccccc1 | null | 71.2 | null |
469,839 | ord_dataset-f1b9e9741a6a4cc68e7070df811f86bb | null | 2000-01-01T00:07:00 | true | [H-].[Na+].[CH2:3]([C:5]1[C:9]2[CH:10]=[CH:11][C:12]([OH:17])=[C:13]([CH2:14][CH2:15][CH3:16])[C:8]=2[O:7][N:6]=1)[CH3:4].CS(O[CH2:23][CH2:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][C:34]([O:36][CH3:37])=[O:35])=[CH:29][CH:28]=1)(=O)=O>CN(C=O)C.C(OCC)(=O)C>[CH2:3]([C:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:17][... | CCCc1c(O)ccc2c(CC)noc12 | COC(=O)Cc1ccc(CCCCOS(C)(=O)=O)cc1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 0.17 | A suspension of sodium hydride (15 mg, 0.36 mmole) in DMF (1.5 mL) was treated with 3-ethyl-6-hydroxy-7-propylbenz-[4,5]-isoxazole (68 mg, 0.33 mmole) and the mixture stirred at room temperature for 10 minutes under a nitrogen atmosphere. A solution of methyl 4-(4-methansulfonyloxybutyl)phenylacetate (100 mg, 0.33 mmol... | CCCc1c(OC(C)CCc2ccc(CC(=O)OC)cc2)ccc2c(CC)noc12 | null | 59.2 | null |
191,374 | ord_dataset-d1bd8c96676b4d21aad27b173c6b4eff | null | 1989-01-01T00:06:00 | true | [CH3:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[CH2:5][NH:6][C:7]1[C:8]2[C:13]([N:14]=[C:15]3[C:20]=1[C:19](=[O:21])[CH2:18][CH2:17][CH2:16]3)=[CH:12][CH:11]=[CH:10][CH:9]=2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[CH2:5][NH:6][C:7]1[C:8]2[C:13]([N:14]=[C:15]3[C:2... | Cc1cccc(CNc2c3c(nc4ccccc24)CCCC3=O)c1 | null | null | [Al+3] | [H-] | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 0 | 0.5 | 3,4-Dihydro-9-(3-methylbenzylamino)acridin-1(2H)-one (3.70 g) was dissolved in 100 ml of dry THF and chilled in ice-water. 1M lithium aluminum hydride in THF (7.0 ml) was added and the reaction stirred 30 minutes in the cold. The reaction mixture was quenched by the sequential addition of 0.5 ml of water, 0.5 ml of 15%... | Cc1cccc(CNc2c3c(nc4ccccc24)CCCC3O)c1 | null | null | null |
1,534,276 | ord_dataset-8d5c200bca27407ab9febe7598e16458 | null | 2015-01-01T00:01:00 | true | [CH:1]([C:3]1[N:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[N:6]=[C:5]([O:13][CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)[CH:4]=1)=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][C:3]1[N:8]=[C:7]([C:9]([F:11])([F:10])[F:12])[N:6]=[C:5]([O:13][CH:14]2[CH2:19][CH2:18][N:17]([C:2... | CC(C)(C)OC(=O)N1CCC(Oc2cc(C=O)nc(C(F)(F)F)n2)CC1 | null | null | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | 4 | To a solution of tert-butyl 4-{[6-formyl-2-(trifluoromethyl)pyrimidin-4-yl]oxy}piperidine-1-carboxylate (202 mg, 0.538 mmol) in methanol (2.0 mL) was added sodium tetrahydroborate (20.4 mg, 0.538 mmol). The reaction solution was stirred at room temperature for 4 hours. The reaction was quenched with water and extracted... | CC(C)(C)OC(=O)N1CCC(Oc2cc(CO)nc(C(F)(F)F)n2)CC1 | null | null | null |
1,440,227 | ord_dataset-275a3da8f45f4536ad29727f0ef9ba66 | null | 2014-01-01T00:06:00 | true | [F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][CH2:27][C:28]1[CH:29]=[C:30]([N:34]2[CH2:38][CH2:37][CH2:36][CH2:35]2)[CH:31]=[CH:32][CH:33]=1)(C(C)(C)C)(C)C>C1COCC1>[N:34]1([C:30]2[CH:29]=[C:28]([CH2:27][OH:26])[CH:33]=[CH:32][CH:31]=2)[CH2:38][CH2:37][CH2:36][CH2:35]1 | CC(C)(C)[Si](C)(C)OCc1cccc(N2CCCC2)c1 | null | null | CCCC[N+](CCCC)(CCCC)CCCC | [F-] | 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 | 3.5 | Tetrabutylammonium fluoride (1.0 M solution in THF, 3.8 ml) was added to a solution of 1-[3-(tert-butyldimethylsilyloxymethyl)phenyl]pyrrolidine in THF (20 ml) and the mixture was stirred at room temperature for 3.5 hours. The reaction mixture was concentrated under reduced pressure and the residue was purified by sili... | OCc1cccc(N2CCCC2)c1 | null | null | null |
117,240 | ord_dataset-3708161f4ba04e959b9a7a8d59fd86e1 | null | 1984-01-01T00:05:00 | true | [ClH:1].C(OC([N:12]([CH2:25][CH:26]1[C:35]2[C:30](=[CH:31][C:32]([OH:37])=[C:33]([OH:36])[CH:34]=2)[CH2:29][CH2:28][NH:27]1)[C:13]1[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[C:15]([O:23][CH3:24])[CH:14]=1)=O)C1C=CC=CC=1.Cl>C(O)(=O)C>[ClH:1].[CH3:24][O:23][C:15]1[CH:14]=[C:13]([CH:18]=[C:17]([O:19][CH3:20])[C... | COc1cc(N(CC2NCCc3cc(O)c(O)cc32)C(=O)OCc2ccccc2)cc(OC)c1OC | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 1-(N-benzyloxycarbonyl-3,4,5-trimethoxyanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (4.4 g), conc. hydrochloric acid (45 ml) and acetic acid (45 ml) was refluxed for 1.5 hours in a stream of nitrogen. The reaction mixture was concentrated to dryness and the residue was washed w... | COc1cc(NCC2NCCc3cc(O)c(O)cc32)cc(OC)c1OC | null | 69.9 | null |
1,613,986 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | C(OC(N1CC[CH:14]([CH:17]([O:20][C:21]2[CH:43]=[CH:42][C:24]3[C:25]4[N:29]([CH2:30][CH2:31][O:32][C:23]=3[CH:22]=2)[CH:28]=[C:27]([C:33]2[N:34]([CH:39]([CH3:41])[CH3:40])[N:35]=[C:36]([CH3:38])[N:37]=2)[N:26]=4)[CH2:18]C)CC1)=O)C1C=CC=CC=1.[CH3:44][C:45]1[S:46][C:47](C(O)C)=[C:48](C)[N:49]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2... | CCC(Oc1ccc2c(c1)OCCn1cc(-c3nc(C)nn3C(C)C)nc1-2)C1CCN(C(=O)OCc2ccccc2)CC1 | Cc1nc(C)c(C(C)O)s1 | null | CCOC(=O)/N=N/C(=O)OCC | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | 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 | 18 | To a suspension of 2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-8-ol from Example 4 (345 mg, 1.06 mmol), 1-(2,4-dimethylthiazol-5-yl)ethanol (250 mg, 1.59 mmol) and triphenylphosphine (0.84 g, 3.18 mmol) in dioxane (15 mL) was added dropwise DEAD (0.63 mL, 3.18 mmol) and th... | Cc1nc(-c2cn3c(n2)-c2ccc(OC(C)c4sc(C)nc4C)cc2OCC3)n(C(C)C)n1 | null | null | null |
1,680,633 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | [Si:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:14](#[N:17])[CH:15]=[CH2:16]>>[Si:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:16][CH2:15][C:14]#[N:17])[CH2:10][CH2:9]1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2] | CC(C)(C)[Si](C)(C)N1CCNCC1 | C=CC#N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 70 | 4 | A flask equipped with a stirrer, reflux condenser, dropping funnel and thermometer was charged with 160.3 g (0.8 mol) of 1-t-butyldimethylsilylpiperazine (Synthesis Example 1) and heated at 70° C. Once the internal temperature became steady, 46.7 g (0.88 mol) of acrylonitrile was added dropwise over 2 hours. Stirring w... | CC(C)(C)[Si](C)(C)N1CCN(CCC#N)CC1 | null | null | null |
902,944 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | [C:1]([CH:4]([C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=1)[CH2:5][CH:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1)([OH:3])=O.[S:22]1[CH:26]=[CH:25][N:24]=[C:23]1[NH2:27]>>[O:9]1[CH2:10][CH2:11][CH:6]([CH2:5][CH:4]([C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=2)[C... | COC(=O)c1ccc(C(CC2CCOCC2)C(=O)O)cc1 | Nc1nccs1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Methyl 4-tert-butoxycarbonylmethylbenzoate (1.71 g, 6.84 mmol) was alkylated with 4-iodomethyltetrahydropyran (1.86 g, 8.21 mmol), employing the method described in Preparation 41, to afford methyl 4-[1-tert-butoxycarbonyl-2-(tetrahydropyran-4-yl)ethyl]benzoate: RTA=3.86 min. A solution of this compound (1.37 g, 3.94 m... | COC(=O)c1ccc(C(CC2CCOCC2)C(=O)Nc2nccs2)cc1 | null | null | null |
339,293 | ord_dataset-4706e7a7f3cd421bb42b7f877cff8af9 | null | 1996-01-01T00:09:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[OH:17])[CH:6]=[CH:7][CH:8]=1.[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][CH2:28][CH:27](O)[CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>>[C:18]([O:22][C:23]([N:25]1[C... | COc1cccc(CCc2ccccc2O)c1 | CC(C)(C)OC(=O)N1CCCC(O)C1 | null | CCOC(=O)N=NC(=O)OCC | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Following a procedure similar to that described in Example 36(a), 1.50 g of 2-[2-(3-methoxyphenyl)ethyl]phenol (prepared as described in Preparation 20), 2.64 g of 1-t-butoxycarbonyl-3-hydroxypiperidine, 3.44 g of triphenylphosphine and 2.29 g of diethyl azodicarboxylate were reacted. The mixture was then worked up as ... | COc1cccc(CCc2ccccc2OC2CCCN(C(=O)OC(C)(C)C)C2)c1 | null | 62.1 | null |
1,766,700 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C[O:12][C:13]([C:15]1[C:23]2[C:18](=[N:19][CH:20]=[C:21]([F:24])[CH:22]=2)[N:17]([S:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)(=[O:27])=[O:26])[C:16]=1[CH2:34][N:35]([CH2:46][C:47]#[N:48])S(C1C=CC(C)=CC=1)(=O)=O)=O>C1COCC1>[C:28]1([S:25]([N:17]2[C:16]3[CH:34]=[N:35][C:46]([C:47... | COC(=O)c1c(CN(CC#N)S(=O)(=O)c2ccc(C)cc2)n(S(=O)(=O)c2ccccc2)c2ncc(F)cc12 | null | null | C[Si](C)(C)[N-][Si](C)(C)C | [Li+] | 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 | -10 | null | Lithium bis(trimethylsilyl)amide (100 mL of a 1N solution in THF, 100 mmol) was added dropwise to a cooled (−78° C.) suspension of 1-benzenesulfonyl-5-fluoro-2-{[cyanomethyl-(toluene-4-sulfonyl)amino]methyl}-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid methyl ester (16.5 g, 29.6 mmol) in dry THF (150 mL). The reaction m... | N#Cc1ncc2c(c1O)c1cc(F)cnc1n2S(=O)(=O)c1ccccc1 | null | 75.2 | null |
813,016 | ord_dataset-892acf7477db4d3a8a8559f004a7c0a2 | null | 2008-01-01T00:03:00 | true | [NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=[O:11])=[CH:2]1.[H-].[Na+].[CH3:15]I.O>CN(C)C=O>[CH3:15][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=[O:11])=[CH:2]1 | O=C(O)c1c[nH]c2ccccc12 | CI | 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 | 0 | 1 | 1H-Indole-3-carboxylic acid (960 mg) was dissolved in N,N-dimethylformamide (15 ml) and cooled to 0° C. Sodiumhydride (720 mg) was added in two divided portions thereto, and the mixture was warmed to room temperature and stirred for 1 hour. The mixture was cooled again to 0° C., and a solution of methyl iodide (0.67 ml... | Cn1cc(C(=O)O)c2ccccc21 | null | 87 | null |
302,659 | ord_dataset-bfcf5a01f1a04ec585ba3f28cb93c8c9 | null | 1995-01-01T00:01:00 | true | [NH2:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([NH2:9])[N:3]=1.[C:10]12([N:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[CH2:19][CH:14]3[CH2:15][CH:16]([CH2:18][CH:12]([CH2:13]3)[CH2:11]1)[CH2:17]2>C(O)C>[C:10]12([N:20]3[CH2:25][CH2:24][N:23]([C:6]4[CH:5]=[C:4]([NH2:9])[N:3]=[C:2]([NH2:1])[N:7]=4)[CH2:22][CH2:21]3)[CH2:17][C... | Nc1cc(Cl)nc(N)n1 | C1CN(C23CC4CC(CC(C4)C2)C3)CCN1 | 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 | 170 | null | A mixture of 2,6-diamino-4-chloropyrimidine (0.43 g, 3.0 mmol) and 1-(1-adamantyl)-piperazine (0.66 g, 3.0 mmol) in ethanol (30 ml) was heated in a sealed tube at 170° C. for 3 hours. After cooling the solvent was removed, the solid residue was dissolved in water (45 ml) and acidified to pH=3 with conc. HCl. The obtain... | Nc1cc(N2CCN(C34CC5CC(CC(C5)C3)C4)CC2)nc(N)n1 | null | 80.2 | null |
90,366 | ord_dataset-6ba93916f2ad4247804469d8c2600b26 | null | 1982-01-01T00:01:00 | true | [OH:1][CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[CH:6]=1)[CH2:3][NH2:4].[C:12](/[CH:16]=[CH:17]/[C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25](=O)[CH2:26][CH3:27])=[CH:20][CH:19]=1)([O:14][CH3:15])=[O:13]>>[C:12](/[CH:16]=[CH:17]/[C:18]1[CH:19]=[CH:20][C:21]([CH2:24][CH2:25][CH:26]([NH:4][CH2:3][CH:2]([OH:1])[C:5]2[... | CCC(=O)Cc1ccc(/C=C/C(=O)OC)cc1 | NCC(O)c1cccc(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 | This was prepared in an identical manner to the compound described in Example 1 using 2-hydroxy-2-(3-chlorophenyl) ethanamine (1.71 g) and 4-{(E)-2-carbomethoxyethenyl}phenylbutan-2-one (2.32 g). Elution with 1% methanolchloroform on Kieselgel 60 gave the title compound (0.86 g), m.p. 87°-89° C. (hexane) as a 50:50 mix... | COC(=O)/C=C/c1ccc(CCC(C)NCC(O)c2cccc(Cl)c2)cc1 | null | 22.3 | null |
174,631 | ord_dataset-4937da99a6a247eb90fa70f0d2eac3db | null | 1988-01-01T00:07:00 | true | [CH3:1][C:2]1[NH:3][C:4]([CH3:41])=[C:5]([C:21]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][N:30]2C(=O)C3=CC=CC=C3C2=O)=[O:22])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N+:18]([O-:20])=[O:19])[C:7]=1[C:8]([O:10][CH3:11])=[O:9].O.NN>>[CH3:1][C:2]1[NH:3][C:4]([CH3:41])=[C:5]([C:21]([O:23][CH2:24][CH... | COC(=O)C1=C(C)NC(C)=C(C(=O)OCCCCCCN2C(=O)c3ccccc3C2=O)C1c1ccccc1[N+](=O)[O-] | null | null | NN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | null | null | Prepared by a method analogous to that of Example 1(b) from 9.1 g (16 mmol) of 1,4-dihydro-2,6-dimethyl-3-methoxycarbonyl-4-(2-nitrophenyl)-5-(6-phthalimidohexyloxy)carbonyl-pyridine and 2.4 ml (49 mmol) of hydrazine hydrate. 6.2 g (89%) of an orange coloured oil. | COC(=O)C1=C(C)NC(C)=C(C(=O)OCCCCCCN)C1c1ccccc1[N+](=O)[O-] | null | null | null |
600,995 | ord_dataset-82e842e611ef4a05b6e7f9ea0a46d52d | null | 2003-01-01T00:07:00 | true | [N+:1]([C:4]([N+:8]([O-:10])=[O:9])([CH3:7])[CH2:5][OH:6])([O-:3])=[O:2].[CH2:11]1OCO[CH2:13][O:12]1.S(=O)(=O)(O)O>C(Cl)Cl>[CH3:5][C:4]([N+:8]([O-:10])=[O:9])([N+:1]([O-:3])=[O:2])[CH2:11][O:12][CH2:13][O:6][CH2:5][C:4]([N+:8]([O-:10])=[O:9])([N+:1]([O-:3])=[O:2])[CH3:7] | CC(CO)([N+](=O)[O-])[N+](=O)[O-] | C1OCOCO1 | null | O=S(=O)(O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | 2 | To a stirred solution of 15 g (0.1 mole) of 2,2-dinitropropanol and 1.5 g (0.05 mole) of s-trioxane in 13 mL of methylene chloride at 0° C., 15 g (98%) of a concentrated sulfuric acid solution was injected with syringe pump over 2 hours. During the reaction, temperature was controlled not to exceed 5° C. After addition... | CC(COCOCC(C)([N+](=O)[O-])[N+](=O)[O-])([N+](=O)[O-])[N+](=O)[O-] | null | 82 | null |
245,697 | ord_dataset-5eb2900a93c842ee98f26c305e657b61 | null | 1992-01-01T00:04:00 | true | Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C([Li])CCC.[C:13]([O:17][C:18]([NH:20][C@H:21]([CH:26]=[O:27])[CH2:22][CH:23]([CH3:25])[CH3:24])=[O:19])([CH3:16])([CH3:15])[CH3:14]>O1CCCC1>[C:13]([O:17][C:18]([NH:20][CH:21]([CH2:22][CH:23]([CH3:25])[CH3:24])[C@H:26]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1)[OH:27])=[O:19])([C... | CC(C)C[C@@H](C=O)NC(=O)OC(C)(C)C | Brc1ccccn1 | null | [Li]CCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 0.08 | To 2-bromopyridine (3.16 g) in 20 ml of dry tetrahydrofuran cooled to -78° C. under argon was added slowly 11.2 ml of n-butyl lithium in tetrahydrofuran (2M). The solution was stirred for 5 minutes and then 2.1 g of N-t-butoxycarbonyl-L-leucinal in 10 ml of tetrahydrofuran was added. The mixture was stirred for 35 minu... | CC(C)CC(NC(=O)OC(C)(C)C)[C@@H](O)c1ccccn1 | null | 21.6 | null |
751,510 | ord_dataset-844a22e1fcab44a5b59c5e2922b2855a | null | 2007-01-01T00:01:00 | true | [C:1](=[N:4][N:5]1[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:7]=[C:6]1[CH2:18][CH2:19][CH3:20])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[CH:1]([NH:4][N:5]1[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:7]=[C:6]1[CH2:18][CH2:19][CH3:20])([CH3:3])[CH3:2] | CCCc1nc2cnc3ccccc3c2n1N=C(C)C | null | null | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | null | A solution of N-isopropylidene-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)amine (4.30 g, 16.1 mmol) in 100 mL of methanol was cooled in an ice water bath. The solution was treated with sodium borohydride (3.05 g, 80.7 mmol) over 5 min. The reaction mixture was allowed to warm to ambient temperature. After 2.5, the reacti... | CCCc1nc2cnc3ccccc3c2n1NC(C)C | null | 57.4 | null |
1,206,697 | ord_dataset-fb72428f30234761b4216139dc228d0c | null | 2012-01-01T00:09:00 | true | [NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=2[Cl:15])[NH:5][C:4](=[S:16])[N:3]=1.I[CH2:18][CH3:19].C(=O)(O)[O-].[Na+].O>CS(C)=O>[Cl:15][C:9]1[CH:10]=[C:11]([Cl:14])[CH:12]=[CH:13][C:8]=1[C:6]1[N:5]=[C:4]([S:16][CH2:18][CH3:19])[N:3]=[C:2]([NH2:1])[CH:7]=1 | CCI | Nc1cc(-c2ccc(Cl)cc2Cl)[nH]c(=S)n1 | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CS(C)=O | null | null | null | null | null | null | null | null | null | 25 | 5 | 67.5 g (248 mmol) of 4-amino-6-(2,4-dichlorophenyl)pyrimidine-2(1H)-thione and 77.37 g (496.04 mmol) of iodoethane are dissolved in 560 ml of dry DMSO and, at RT, 270 ml of a saturated aqueous sodium bicarbonate solution are slowly added. The mixture is stirred at RT for 5 h and then 440 ml of water are added. The prec... | CCSc1nc(N)cc(-c2ccc(Cl)cc2Cl)n1 | null | null | null |
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