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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
58,040 | ord_dataset-1590b34936164499aa4ed4fe0ef21255 | null | 1979-01-01T00:08:00 | true | [C:1]([NH:9][NH2:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=[CH:12][C:13]([Cl:16])([Cl:15])[Cl:14]>C1C=CC=CC=1>[C:1]([NH:9][N:10]=[CH:12][C:13]([Cl:16])([Cl:15])[Cl:14])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1 | O=CC(Cl)(Cl)Cl | NNC(=O)c1ccccc1 | null | null | null | 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 | 10 g (0.073 mol) of benzoylhydrazine were suspended in benzene, 200 ml, and 18.3 g (0.124 mol) of chloral were added dropwise to the suspension which was then refluxed under agitation for 3 hours. Upon cooling, the sedimented crystals were collected by filtration and washed well with benzene. In this way, white brown c... | O=C(NN=CC(Cl)(Cl)Cl)c1ccccc1 | null | null | null |
1,147,356 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | Cl[CH2:2][C:3]1[NH:15][C:14](=[O:16])[CH:13]2[CH:5]([C:6]3[CH2:7][CH2:8][C:9]4[CH:20]=[CH:19][CH:18]=[CH:17][C:10]=4[C:11]=3[S:12]2)[N:4]=1.C(N(C(C)C)CC)(C)C.[NH2:30][C:31]1[CH:32]=[C:33]([OH:37])[CH:34]=[CH:35][CH:36]=1>CN(C)C=O>[OH:37][C:33]1[CH:32]=[C:31]([NH:30][CH2:2][C:3]2[NH:15][C:14](=[O:16])[CH:13]3[CH:5]([C:6... | O=C1NC(CCl)=NC2C3=C(SC12)c1ccccc1CC3 | Nc1cccc(O)c1 | 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 | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | A solution of EXAMPLE 12E (18 mg), diisopropylethylamine and 3-aminophenol (10 mg) in N,N-dimethylformamide (0.5 mL) were heated at 70° C. for 2 hours. The mixture was cooled and purified by HPLC on a C18 column using 0-70% acetonitrile/0.1% trifluoroacetic acid in water to provide 7 mg of the title compound as the tri... | O=C1NC(CNc2cccc(O)c2)=NC2C3=C(SC12)c1ccccc1CC3 | null | 31.4 | null |
410,228 | ord_dataset-fbdd058349aa456f812e3546c84baab5 | null | 1998-01-01T00:09:00 | true | [Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([NH:9][C:10](=[O:19])[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14](C)[CH:13]=2)=[C:4]([N+:20]([O-:22])=O)[CH:3]=1.ClC1C=C2C(=CC=1Cl)NC(=[O:35])C(C1C=CC(OC)=CC=1)=[N+]2[O-].[K+].[Br-]>CCO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][C:7]=1[Cl:8])[NH:9][C:10](=[O:19])[C:11]([C:12]1[CH:17]=[... | Cc1cccc(CC(=O)Nc2cc(Cl)c(Cl)cc2[N+](=O)[O-])c1 | COc1ccc(-c2c(=O)[nH]c3cc(Cl)c(Cl)cc3[n+]2[O-])cc1 | null | [Br-] | [K+] | 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 | The title compound was prepared according to the general procedure of Example 15, except that nitrone 133 is substituted for nitrone 128. Yield: 30%; mp 266°-268° C. (from EtOH); IR (KBr) 3440, 3218, 3102, 2929, 1674, 1619, 1470, 1348, 1143 and 1112 cm-1 ; 1H NMR (in DMSO-d6) δ6.86 (m, 2H), 7.25 (m, 2H), 7.53 (s, 1H), ... | O=c1[nH]c2cc(Cl)c(Cl)cc2[n+]([O-])c1-c1ccccc1O | null | 30 | null |
408,682 | ord_dataset-324fb6fdc2414cb79e436bf5d04d4bd2 | null | 1998-01-01T00:08:00 | true | Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:5][CH:4]=1.[C:14]1([CH:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)[N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C>O1CCOCC1>[C:14]1([CH:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)... | c1ccc(C(c2ccccn2)N2CCNCC2)cc1 | COC(=O)Cc1ccc(CBr)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | Using 2.8 g of methyl 4-bromomethylphenylacetate, 2.9 g of 1-[phenyl-(2-pyridyl)methyl]piperazine, 2 ml of triethylamine, and 100 ml of dioxane, the reaction procedure of Example 1 was otherwise repeated and recrystallized from benzene-hexane to provide 2.47 g of methyl 4-[[4-[phenyl-(2-pyridyl)methyl]-1-piperazinyl]me... | COC(=O)Cc1ccc(CN2CCN(C(c3ccccc3)c3ccccn3)CC2)cc1 | null | 51.9 | null |
980,192 | ord_dataset-35b56288528641309a040cc2b6710b61 | null | 2010-01-01T00:08:00 | true | [F:1][C:2]1[CH:3]=[CH:4][C:5]([C:25]([F:28])([F:27])[F:26])=[C:6]([CH:24]=1)[C:7]([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:23]=[CH:22][C:18]([C:19](O)=O)=[CH:17][N:16]=2)[CH2:11][CH2:10]1)=[O:8].[NH2:29][CH2:30][CH:31]([NH2:35])[CH2:32][CH2:33][CH3:34]>O=P(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:25]([F:28])([F:27])[F... | CCCC(N)CN | O=C(O)c1ccc(N2CCN(C(=O)c3cc(F)ccc3C(F)(F)F)CC2)nc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=P(Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 25 | null | To a stirred solution of 6-[4-(5-fluoro-2-trifluoromethylbenzoyl)piperazin-1-yl]nicotinic acid (0.509 g, 1.281 mmol) in POCl3(10 mL) was added dropwise 1,2-diaminopentane (3.50 g, 34.0 mmol). The resulting mixture was stirred at reflux for 16 h and then allowed to cool to ambient temperature and concentrated. The resid... | CCCC1CN=C(c2ccc(N3CCN(C(=O)c4cc(F)ccc4C(F)(F)F)CC3)nc2)N1 | null | 9 | null |
1,378,880 | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | null | 2013-01-01T00:12:00 | true | Cl[C:2]1[N:6]([CH2:7][CH:8]([F:10])[F:9])[N:5]=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[NH:14]1[CH2:20][CH2:19][CH2:18][CH:17]([OH:21])[CH2:16][CH2:15]1.CCN(C(C)C)C(C)C>CCO>[F:9][CH:8]([F:10])[CH2:7][N:6]1[C:2]([N:14]2[CH2:20][CH2:19][CH2:18][CH:17]([OH:21])[CH2:16][CH2:15]2)=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=[N:5]1 | OC1CCCNCC1 | O=[N+]([O-])c1cnn(CC(F)F)c1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | null | null | A solution of 5-chloro-1-(2,2-difluoroethyl)-4-nitro-1H-pyrazole (470 mg, 2.22 mmol), azepan-4-ol (281 mg, 2.44 mmol) and DIPEA (1 mL) in EtOH (3 mL) was heated at 155° C. in the microwave for 5 hr. The solvent was removed under reduced pressure and the residue purified by silica gel column chromatography (0-100% EtOAc... | O=[N+]([O-])c1cnn(CC(F)F)c1N1CCCC(O)CC1 | null | 62.1 | null |
1,504,669 | ord_dataset-1a1aa5d1c3224edca0aec6e3398da985 | null | 2014-01-01T00:11:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH:15]=O)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[CH3:17][NH2:18]>>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:15][NH:18][CH3:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8] | CN | O=CC1(c2ccc(F)c(Cl)c2)CCCCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was synthesized from 1-(3-chloro-4-fluorophenyl)-cyclohexanecarbaldehyde and methyl amine using General Procedure H1 and was obtained in 55% yield. LCMS Rt=7.73 min, m/z=256 (M+1). 1H NMR (CDCl3, δ): 7.37 (dd, J=2.4, 7.1 Hz, 1H), 7.22 (ddd, J=2.4, 4.6, 8.7 Hz, 1H), 7.09 (t, J=8.7 Hz, 1H), 2.58 (s, 2H... | CNCC1(c2ccc(F)c(Cl)c2)CCCCC1 | null | 55 | null |
819,230 | ord_dataset-50f99930fc41474db226bc80774b38df | null | 2008-01-01T00:04:00 | true | C([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][C:14]2[CH:26]=[CH:25][C:24]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:17](=[O:27])[C:16]=3[CH:15]=2)[CH2:9]1)(OC(C)(C)C)=O.O.[C:29]1([CH3:39])[CH:34]=[CH:33][C:32]([S:35]([OH:38])(=[O:37])=[O:36])=[CH:31][CH:30]=1>CCOC(C)=O>[C:29]1([CH3:39])[CH:30]=[CH:31][C:32]([S:35]([O... | CC(C)(C)OC(=O)N1CC[C@H](Oc2ccc3c(c2)C(=O)c2ccccc2-3)C1 | null | null | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | O | null | null | null | null | null | null | null | null | null | 25 | 18 | A solution of 2-[(S)-N-Boc-pyrrolidin-3-yloxy]-fluoren-9-one (315 mg, 0.863 mmol; Example 4A) and p-toluenesulfonic acid monohydrate (165 mg, 0.868 mmol; Aldrich) in EtOAc (15 mL) was heated to reflux. A precipitate began to form after about 30 min of heating. After 18 h, the mixture was cooled to room temperature and ... | O=C1c2ccccc2-c2ccc(O[C@H]3CCNC3)cc21 | null | 88.4 | null |
588,103 | ord_dataset-7a74d48eeefd45aba53e7258f3ae067a | null | 2003-01-01T00:04:00 | true | C([O:3][C:4]([CH:6]1[CH2:11][C:10]([OH:18])([C:12]#[C:13][Si](C)(C)C)[CH2:9][CH2:8][O:7]1)=O)C.[NH3:19]>CO>[C:12]([C:10]1([OH:18])[CH2:9][CH2:8][O:7][CH:6]([C:4]([NH2:19])=[O:3])[CH2:11]1)#[CH:13] | N | CCOC(=O)C1CC(O)(C#C[Si](C)(C)C)CCO1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | 0.17 | 4-Hydroxy-4-trimethylsilanylethynyl-tetrahydro-pyran-2-carboxylic acid ethyl ester (2.50 g, 9.25 mmol) was dissolved in MeOH (20 mL) in a pressure reaction tube and NH3 gas was passed through the solution for 10 minutes with stirring. The tube was tightly capped and the reaction was stirred for 3 days. After solvent re... | C#CC1(O)CCOC(C(N)=O)C1 | null | 97 | null |
472,081 | ord_dataset-cd531114850e4f239b2a3661044ae672 | null | 2000-01-01T00:08:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][NH2:17])[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]=[C:26]=[S:27])=[CH:21][CH:20]=1>O1CCCC1>[CH3:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]([NH:17][CH2:16][CH2:15][N:12]2[CH2:13][CH2:14][N:9]([C:4]3[CH... | Cc1ccc(N=C=S)cc1 | NCCN1CCN(c2ccc(Cl)c(Cl)c2)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 1 | A mixture of 4-(3,4-dichlorophenyl)-1-piperazineethanamine (0.01 mol) and 4-methyl-1-isothiocyanatobenzene (0.01 mol) in tetrahydrofuran (300 ml) was stirred at room temperature for 1 hour. The solvent was evaporated. The residue was recrystallized from DIPE. The precipitate was filtered off and dried. The product was ... | Cc1ccc(NC(=S)NCCN2CCN(c3ccc(Cl)c(Cl)c3)CC2)cc1 | null | 99.2 | null |
1,450,014 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([OH:9])[CH:3]=1.[CH3:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=1[CH3:20])[C:14](O)=O>>[Br:1][C:2]1[CH:8]=[CH:7][C:5]2[N:6]=[C:14]([C:13]3[CH:17]=[CH:18][C:19]([CH3:20])=[C:11]([CH3:10])[CH:12]=3)[O:9][C:4]=2[CH:3]=1 | Cc1ccc(C(=O)O)cc1C | Nc1ccc(Br)cc1O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Preparation is carried out analogously to 4.1.a from 4-bromo-2-hydroxy-aniline and 3,4-dimethyl-benzoic acid. | Cc1ccc(-c2nc3ccc(Br)cc3o2)cc1C | null | null | null |
183,352 | ord_dataset-8537fa92abf34c849134600c0c2bbcc7 | null | 1989-01-01T00:02:00 | true | Cl.[NH2:2][OH:3].[CH:4]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:14](=O)[C:8]=2[CH:7]=[CH:6][N:5]=1>C(N(CC)CC)C>[OH:3][N:2]=[C:14]1[C:8]2[CH:7]=[CH:6][N:5]=[CH:4][C:9]=2[CH:10]=[CH:11][CH:12]=[CH:13]1 | NO | O=c1ccccc2cnccc12 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | 25 | 8 | Hydroxylamine hydrochloride (2.20 g, 0.317 mole) was added to a stirred mixture of cyclohepta[1,2-c]pyridin5-one and triethylamine (15.00 ml) and the resulting yellow solution was stirred overnight at its reflux temperature. The pale yellow solution was cooled to room temperature, then concentrated by solvent evaporati... | ON=c1ccccc2cnccc12 | null | 53 | null |
1,700,875 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | [C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][C@@H:13]([C:15]([F:18])([F:17])[F:16])[CH2:12][N:11]([C:19]2[CH:24]=[CH:23][N:22]=[CH:21][C:20]=2[NH:25][C:26]([C:28]2[C:37]([NH:38]C(=O)OCC3C=CC=CC=3)=[CH:36][C:35]3[C:30](=[CH:31][C:32]([C:49]4[CH2:50][CH2:51][N:52]([CH3:55])[CH2:53][CH:54]=4)=[CH:33][CH:34]=3)[N:29]=2)=[O:27])... | [H][H] | CN1CC=C(c2ccc3cc(NC(=O)OCc4ccccc4)c(C(=O)Nc4cnccc4N4C[C@@H](NC(=O)OC(C)(C)C)C[C@@H](C(F)(F)F)C4)nc3c2)CC1 | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of benzyl [2-[({4-[(3S,5R)-3-[(tert-butoxycarbonyl)amino]-5-(trifluoromethyl)piperidin-1-yl]pyridin-3-yl}amino)carbonyl]-7-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)quinolin-3-yl]carbamate (0.010 g, 0.013 mmol) in 1.5 mL of MeOH was hydrogenated in the presence of 10% Pd on carbon (3.5 mg) under a balloon of h... | CN1CCC(c2ccc3cc(N)c(C(=O)Nc4cnccc4N4C[C@@H](NC(=O)OC(C)(C)C)C[C@@H](C(F)(F)F)C4)nc3c2)CC1 | null | 79.7 | null |
790,444 | ord_dataset-530502f8e61e455784f93c5faa45c94b | null | 2007-01-01T00:09:00 | true | Cl[C:2]1[C:3]2[C:10]([C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=3)=[O:12])=[CH:9][N:8]([CH:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[C:4]=2[N:5]=[CH:6][N:7]=1.[NH4+:27].[OH-]>O1CCOCC1>[NH2:27][C:2]1[C:3]2[C:10]([C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=3)=... | [NH4+] | O=C(c1cccc([N+](=O)[O-])c1)c1cn(C2CCCC2)c2ncnc(Cl)c12 | null | [OH-] | 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 (4-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(3-nitro-phenyl)-methanone (11.3 g, 30.5 mmol) and NH4OH (200 mL) in 1,4-Dioxane (300 mL) was heated to 50° C. in a pressure reactor. After 2 h the reaction was concentrated under reduced pressure. The residue was dissolved in CH2Cl2 and washed with... | Nc1ncnc2c1c(C(=O)c1cccc([N+](=O)[O-])c1)cn2C1CCCC1 | null | 97 | null |
1,253,151 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | [Br:1][C:2]1[CH:3]=[CH:4][C:5](I)=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH2:11]([O:13][C:14](=[O:33])[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18](B2OC(C)(C)C(C)(C)O2)[CH:17]=1)[CH3:12]>>[CH2:11]([O:13][C:14](=[O:33])[CH2:15][C:16]1[CH:17]=[C:18]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:9][C:6]=2[CH:7]=[O:8])[C:19]([O... | CCOC(=O)Cc1ccc(OC)c(B2OC(C)(C)C(C)(C)O2)c1 | O=Cc1cc(Br)ccc1I | null | null | null | null | null | null | null | 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 according to the procedure described in Example 1, Step 4, using the following starting materials: 5-bromo-2-iodo-benzaldehyde and [4-methoxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetic acid ethyl ester. | CCOC(=O)Cc1ccc(OC)c(-c2ccc(Br)cc2C=O)c1 | null | null | null |
1,592,153 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [C:1]1([C@@H:7]2[CH2:9][C@H:8]2[C:10]([OH:12])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.C(N(CC)CC)C.[CH:44]([O:47][C:48]1[N:53]=[CH:52][C:51]([C@@H:54]([NH2:56])[CH3:55])=[CH:50][CH:49]=1)([CH3:46])[CH3:45]>CN(C=O)C>[CH:44]([O:47][C:48]1[N:53]=[CH:52][C:51]([C@@H:54]([... | CC(C)Oc1ccc([C@H](C)N)cn1 | O=C(O)[C@@H]1C[C@H]1c1ccccc1 | null | CN(C)C(On1nnc2cccnc21)=[N+](C)C | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 0.25 | Trans-2-phenyl-1-cyclopropanecarboxylic acid IM46 (0.590 g, 3.64 mmol) was dissolved in DMF (15.0 mL). N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (1.38 g, 3.63 mmol) was added. Triethylamine (1.10 mL, 7.89 mmol) was then added and the mixture was stirred for 15 minutes at room temperatu... | CC(C)Oc1ccc([C@H](C)NC(=O)[C@H]2C[C@@H]2c2ccccc2)cn1 | null | null | null |
1,363,719 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | Cl.Cl.Cl.[O:4]1[C:12]2[CH:11]=[CH:10][N:9]=[C:8]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][C@H:21]4[CH2:26][CH2:25][C@H:24]([NH2:27])[CH2:23][CH2:22]4)[CH2:15][CH2:14]3)[C:7]=2[CH2:6][CH2:5]1.[O:28]1[C:32]2[CH:33]=[CH:34][C:35]([C:37](O)=[O:38])=[CH:36][C:31]=2[O:30][CH2:29]1>>[O:4]1[C:12]2[CH:11]=[CH:10][N:9]=[C:... | N[C@H]1CC[C@H](CCN2CCN(c3nccc4c3CCO4)CC2)CC1 | O=C(O)c1ccc2c(c1)OCO2 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound, white solid (107 mg, 89%), MS (ISP) m/z=479.3 [(M+H)+], mp 243.5° C., was prepared in accordance with the general method of example 32 from trans-4-{2-[4-(2,3-dihydrofuro[3,2-c]pyridin-4-yl)-piperazin-1-yl]-ethyl}-cyclohexanamine trihydrochloride (intermediate C) (110 mg, 0.25 mmol) and benzo[1,3]di... | O=C(N[C@H]1CC[C@H](CCN2CCN(c3nccc4c3CCO4)CC2)CC1)c1ccc2c(c1)OCO2 | null | null | null |
824,899 | ord_dataset-0ca5627a13c049a99463095023b09fe5 | null | 2008-01-01T00:06:00 | true | F[C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[NH2:13][C:14]1[S:15][CH:16]=[CH:17][C:18]=1[C:19]#[N:20].[H-].[Na+]>C1COCC1>[F:9][C:5]1[C:6]([F:8])=[CH:7][C:2]([NH:13][C:14]2[S:15][CH:16]=[CH:17][C:18]=2[C:19]#[N:20])=[C:3]([N+:10]([O-:12])=[O:11])[CH:4]=1 | N#Cc1ccsc1N | O=[N+]([O-])c1cc(F)c(F)cc1F | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 24 | Combine 2,4,5-trifluoro-nitrobenzene (5.00 g, 24.24 mmol), 2-aminothiophene-3-carbonitrile (3.51 g, 28.24 mmol), and anhydrous THF (30.0 ml). Cool the mixture to 10° and then slowly add NaH (2.26 g, 56.47 mmol, 60% dispersion in mineral oil) while keeping the temperature less than 10°. Warm the mixture to ambient tempe... | N#Cc1ccsc1Nc1cc(F)c(F)cc1[N+](=O)[O-] | null | 59.6 | null |
764,349 | ord_dataset-7a8649d55889427e85b208ae89475895 | null | 2007-01-01T00:04:00 | true | [CH3:1][O:2][CH2:3][CH2:4][N:5]([CH2:22][C:23]1[CH:35]=[CH:34][C:26]([O:27][CH2:28][C:29]([O:31]CC)=[O:30])=[C:25]([CH3:36])[CH:24]=1)[C:6]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[CH:9]=[CH:8][N:7]=1.[OH-].[Na+]>CO.O1CCCC1>[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH2:22][C:23]... | CCOC(=O)COc1ccc(CN(CCOC)c2nccc(-c3ccc(C(F)(F)F)cc3)n2)cc1C | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CO | null | null | null | null | null | null | null | null | null | 25 | 1 | To a solution of ethyl {4-[((2-methoxyethyl){4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl}amino)methyl]-2-methylphenoxy}acetate (80 mg, 0.16 mmol) in methanol (1.5 mL) and tetrahydrofuran (1.5 mL) was added 2M sodium hydroxide (1.5 mL). The resulting mixture was stirred at room temperature for 1 h. The solvents were rem... | COCCN(Cc1ccc(OCC(=O)O)c(C)c1)c1nccc(-c2ccc(C(F)(F)F)cc2)n1 | null | 94.6 | null |
1,180,780 | ord_dataset-0f9d2dbe929a45c3892ae75e81e99443 | null | 2012-01-01T00:06:00 | true | C(OC(=O)[NH:7][CH2:8][C@@H:9]([NH:17][C:18]([C:20]1[C:32]2[CH2:31][CH2:30][C:29]3[CH:28]=[N:27][CH:26]=[CH:25][C:24]=3[C:23]=2[N:22]([CH2:33][C:34]([F:37])([F:36])[F:35])[CH:21]=1)=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(C)(C)C.Cl.C(OCC)C>O1CCOCC1>[NH2:7][CH2:8][C@@H:9]([NH:17][C:18]([C:20]1[C:32... | CC(C)(C)OC(=O)NC[C@H](Cc1ccccc1)NC(=O)c1cn(CC(F)(F)F)c2c1CCc1cnccc1-2 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | CCOCC | null | null | null | null | null | null | null | null | null | 25 | 8 | To a solution of tert-butyl[(2S)-3-phenyl-2-({[1-(2,2,2-trifluoroethyl)-4,5-dihydro-1H-pyrrolo[2,3-f]isoquinolin-3-yl]carbonyl}amino)propyl]carbamate L8 (0.38 mmol) in dry dioxane (20 mL), 4M HCl in dioxane (5 mL) was added. The reaction mixture was stirred at rt overnight. The solvent was removed and the residue disso... | NC[C@H](Cc1ccccc1)NC(=O)c1cn(CC(F)(F)F)c2c1CCc1cnccc1-2 | null | 75 | null |
240,279 | ord_dataset-685186618e9f4e7aaa72ac40c16ef354 | null | 1992-01-01T00:01:00 | true | [CH3:1][C:2]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:5]([C:12]([O:14]CC)=[O:13])[O:4][N:3]=1.[OH-].[K+]>C(O)C.O>[CH3:1][C:2]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:5]([C:12]([OH:14])=[O:13])[O:4][N:3]=1 | CCOC(=O)c1onc(C)c1C(=O)OCC | 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 | null | 16 | 65 g of diethyl 3-methylisoxazole-4,5-dicarboxylate, dissolved in 100 ml of ethanol, are added dropwise to 18.9 g of potassium hydroxide in 100 ml of water at room temperature. After 16 hours, the mixture is poured onto 300 ml of water and extracted with ether, and the aqueous phase is acidified with concentration hydr... | CCOC(=O)c1c(C)noc1C(=O)O | null | null | null |
407,228 | ord_dataset-d5bb2294ac964841b8ffc9e0a34e93af | null | 1998-01-01T00:07:00 | true | [CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C@@H:15]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:16][C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[I:29]I.CCOC(C)=O>C(Cl)(Cl)Cl.[O-]S(C(F)(F)F)(=O)=O.[Ag+]>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C@@H:15]([C:23]3[C... | II | COc1ccc([C@H](Cc2ccncc2)c2ccccc2)cc1OC1CCCC1 | null | [Ag+] | O=S(=O)([O-])C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | From (R)-(+)-4-[2-(3-cyclopentyloxy-4-methoxyphenyl)-2-phenylethyl] pyridine (made as described in International Patent Specification No. WO 94/14742) (1.82 g, 4.88 mmol) in CHCl3 (50 ml)m, silver triflate (1.26 g, 4.88 mmol) and iodine (1.24 g, 4.88 mmol). Chromatography (SiO2 ;EtOAc) afforded the title compound (2.2 ... | COc1cc(I)c([C@H](Cc2ccncc2)c2ccccc2)cc1OC1CCCC1 | null | 90.3 | null |
696,100 | ord_dataset-a7baa616c65d42559e25ca0ba61e0744 | null | 2006-01-01T00:01:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH:11]=[C:12]([Cl:26])[C:13]=1[O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21]C)=[C:17]([CH:23]([CH3:25])[CH3:24])[CH:16]=1)[CH2:5][C:6]1[NH:10][N:9]=[N:8][N:7]=1.B(F)(F)F.S(C)C>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:11]=[C:12]([Cl:26])[C:13]=1[O:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([CH:23](... | COc1ccc(Oc2c(Cl)cc(Cc3nnn[nH]3)cc2Cl)cc1C(C)C | null | null | FB(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CSC | null | null | null | null | null | null | null | null | null | null | null | A reaction mixture of 3,5-dichloro-4-(4-methoxy-3-isopropylphenoxy)-benzyltetrazole (60 mg), BF3.Me2S (0.5 ml) and CH2Cl2 (6 ml) was stirred at room temperature over night. The yield after purification was quantitative. | CC(C)c1cc(Oc2c(Cl)cc(Cc3nnn[nH]3)cc2Cl)ccc1O | null | null | null |
790,443 | ord_dataset-530502f8e61e455784f93c5faa45c94b | null | 2007-01-01T00:09:00 | true | [Li]CCCC.Br[C:7]1[C:15]2[C:14]([Cl:16])=[N:13][CH:12]=[N:11][C:10]=2[N:9]([CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:8]=1.[N+:22]([C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=1)[C:28](Cl)=[O:29])([O-:24])=[O:23]>C1COCC1>[Cl:16][C:14]1[C:15]2[C:7]([C:28]([C:27]3[CH:31]=[CH:32][CH:33]=[C:25]([N+:22]([O-:24])=[O:23])[C... | O=C(Cl)c1cccc([N+](=O)[O-])c1 | Clc1ncnc2c1c(Br)cn2C1CCCC1 | 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 | null | n-BuLi (22 mL, 2.5 M in Hexane, 55.0 mmol) was added dropwise to a solution of 5-Bromo-4-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine (15.0 g, 50.0 mmol) in THF (200 mL) at −78° C. After 1 h the resulting solution was added via cannula to a solution of 3-Nitrobenzoyl Chloride in THF (100 mL) at −78° C. After 30 min... | O=C(c1cccc([N+](=O)[O-])c1)c1cn(C2CCCC2)c2ncnc(Cl)c12 | null | 65 | null |
1,757,707 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=3)=[CH:9][N:10]=2)[N:7]=1.[CH:18]1([NH2:25])[CH2:23][CH2:22][CH2:21][CH:20]([NH2:24])[CH2:19]1.C([O-])(O)=O.[Na+]>CN1C(=O)CCC1>[Cl:17][C:13]1[CH:12]=[C:11]([C:8]2[N:6]3[N:7]=[C:2]([NH:24][CH:20]4[CH2:21][CH2:22][CH2:23][CH:18]([... | Clc1cccc(-c2cnc3ccc(Cl)nn23)c1 | NC1CCCC(N)C1 | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN1CCCC1=O | null | null | null | null | null | null | null | null | null | null | 180 | 1 | To a solution of 6-chloro-3-(3-chlorophenyl)imidazo[1,2-b]pyridazine (100 mg, 0.38 mmol) and cyclohexane-1,3-diamine (43 mg, 0.38 mmol) in NMP (1.0 mL) was added NaHCO3 (32 mg, 0.38 mmol), the mixture was stirred at 180° C. for 60 mins under microwave irridation. The mixture was purified by flash chromatograph to give ... | NC1CCCC(Nc2ccc3ncc(-c4cccc(Cl)c4)n3n2)C1 | null | 23.2 | null |
1,741,118 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | Cl.[NH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([NH:9][C:10]([C:12]2[C:16]3[N:17]=[CH:18][N:19]=[C:20]([C:21]4[CH:26]=[C:25]([CH:27]([F:29])[F:28])[CH:24]=[CH:23][C:22]=4[O:30][CH2:31][CH:32]4[CH2:34][CH2:33]4)[C:15]=3[NH:14][C:13]=2[CH3:35])=[O:11])[CH2:5][C@@H:4]1[CH3:36].[C:37](Cl)(=[O:40])[CH2:38][CH3:39]>>[CH:32]1([CH2:31... | Cc1[nH]c2c(-c3cc(C(F)F)ccc3OCC3CC3)ncnc2c1C(=O)N[C@H]1CC[C@H](N)[C@@H](C)C1 | CCC(=O)Cl | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Starting from N-[(1S*,3S*,4S*)-4-amino-3-methylcyclohexyl]-4-[2-(cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide hydrochloride (example D.f65) and commercially available propionyl chloride the title compound is obtained as colorless solid. | CCC(=O)N[C@H]1CC[C@H](NC(=O)c2c(C)[nH]c3c(-c4cc(C(F)F)ccc4OCC4CC4)ncnc23)C[C@@H]1C | null | null | null |
994,144 | ord_dataset-b6d8835b0c934476a36e6149e7597487 | null | 2010-01-01T00:09:00 | true | [C:1]([CH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9]2[S:13][C:12]([NH:14][C:15](=[O:17])[CH3:16])=[N:11][C:10]=2[CH3:18])[N:8]=1)#[N:2].Cl.[NH2:20][OH:21].C(N(CC)CC)C>O1CCOCC1>[NH2:2]/[C:1](=[N:20]/[OH:21])/[CH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9]2[S:13][C:12]([NH:14][C:15](=[O:17])[CH3:16])=[N:11][C:10]=2[CH3:18])[N:8]=1 | NO | CC(=O)Nc1nc(C)c(-c2csc(CC#N)n2)s1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | C1COCCO1 | null | null | null | null | null | null | null | null | null | 80 | null | N-[2-(cyanomethyl)-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl]acetamide, Compound (3) (50 mg; 0.18 mmol; 1 eq.), is dissolved in dioxane (10 ml). Hydroxylamine hydrochloride (15 mg; 0.22 mmol; 1.20 eq.) and N,N-diethylethanamine (0.03 ml; 0.22 mmol; 1.20 eq.) are added and reaction mixture is heated at 80° C. overnight. React... | CC(=O)Nc1nc(C)c(-c2csc(C/C(N)=N\O)n2)s1 | null | 95 | null |
177,588 | ord_dataset-3ef78abb9a384506b240a419b70e6ceb | null | 1988-01-01T00:09:00 | true | [N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].[C:12]([O:18][CH:19]([CH3:22])[CH2:20][Cl:21])(=[O:17])[CH2:13][C:14]([CH3:16])=[O:15].Cl>C1(C)C=CC=CC=1>[C:14]([C:13](=[CH:7][C:6]1[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[C:12]([O:18][CH:19]([CH3:22])[CH2:20][Cl:21])=[O:17])(=... | CC(=O)CC(=O)OC(C)CCl | O=Cc1cccc([N+](=O)[O-])c1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | 48 | A solution containing 12.2 g of 3-nitrobenzaldehyde and 14.3 g of 1-methyl-2-chloroethyl acetoacetate in 80 ml of toluene, maintained at 0°-5° C., was saturated with hydrogen chloride gas. After two days at 20°-25° C., the residual hydrogen chloride was removed by bubbling nitrogen through the solution. The toluene was... | CC(=O)C(=Cc1cccc([N+](=O)[O-])c1)C(=O)OC(C)CCl | null | 82.9 | null |
1,698,643 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | ClCCCl.[CH3:5][C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)[O:8][N:7]=1.[I:20]N1C(=O)CCC1=O.OS(O)(=O)=O>O>[I:20][C:10]1[C:6]([CH3:5])=[N:7][O:8][C:9]=1[C:11]1[CH:12]=[CH:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=1 | O=C1CCC(=O)N1I | Cc1cc(-c2ccc([N+](=O)[O-])cc2)on1 | null | O=S(=O)(O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | ClCCCl | null | null | null | null | null | null | null | null | null | 25 | 4 | To a 100 mL RB flask fitted with magnetic stirrer was charged with 10 mL of 1,2-dichloroethane. To the stirring solution were added 3-methyl-5-(4-nitrophenyl)-1,2-oxazole (0.27 g, 1.30 mmol), N-iodosuccinimide (0.28 g, 1.24 mmol), followed by concentrated H2SO4 (0.2 mL) at 0° C. and stirred at room temperature for 4 h.... | Cc1noc(-c2ccc([N+](=O)[O-])cc2)c1I | null | 97.7 | null |
1,329,375 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | [C:1]([C:5]1[N:10]=[CH:9][C:8]([C:11]2[N:12]([C:32](Cl)=[O:33])[C@@:13]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)([CH3:24])[C@@:14]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)([CH3:16])[N:15]=2)=[C:7]([O:35][CH2:36][CH3:37])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:38][C:39]([CH3:49])([CH3:48])[... | CCOc1cc(C(C)(C)C)ncc1C1=N[C@@](C)(c2ccc(Cl)cc2)[C@@](C)(c2ccc(Cl)cc2)N1C(=O)Cl | CC(C)(C)C(=O)N1CCNCC1 | null | null | null | null | null | null | null | 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 a manner analogous to the method described in examples 8, (4S,5R)-2-(6-tert-butyl-4-ethoxy-pyridin-3-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride (example 51) was coupled with 2,2-dimethyl-1-piperazin-1-yl-propan-1-one (Oakwood) to give the title compound. HR-MS (ES, m/z) calc... | CCOc1cc(C(C)(C)C)ncc1C1=N[C@@](C)(c2ccc(Cl)cc2)[C@@](C)(c2ccc(Cl)cc2)N1C(=O)N1CCN(C(=O)C(C)(C)C)CC1 | null | null | null |
1,407,694 | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | null | 2014-01-01T00:03:00 | true | Br[C:2]1[S:3][CH:4]=[C:5]([CH3:7])[N:6]=1.[CH2:8]([N:12]1[N:16]=[C:15]2[CH:17]=[CH:18][CH:19]=[CH:20][C:14]2=[N:13]1)[CH2:9][C:10]#[CH:11]>>[CH3:7][C:5]1[N:6]=[C:2]([C:11]#[C:10][CH2:9][CH2:8][N:12]2[N:13]=[C:14]3[CH:20]=[CH:19][CH:18]=[CH:17][C:15]3=[N:16]2)[S:3][CH:4]=1 | Cc1csc(Br)n1 | C#CCCn1nc2ccccc2n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared in accordance with the general method of Example 1, from 2-bromo-4-methylthiazole (100 mg, 0.56 mmol) and 2-(but-3-ynyl)-2H-benzo[d][1,2,3]triazole (96 mg, 0.56 mmol, Example 109(D)). The crude residue was purified by flash chromatography (cyclohexane/AcOEt 4:1) to yield 40 mg (0.15 mmol... | Cc1csc(C#CCCn2nc3ccccc3n2)n1 | null | 26.8 | null |
974,952 | ord_dataset-f886e51ba1484c76a94bce1482f1eab9 | null | 2010-01-01T00:07:00 | true | [F:1][C:2]([F:34])([F:33])[C:3]1[CH:4]=[C:5]([CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=1)[CH2:6][N:7]([CH:11]1[CH2:17][CH2:16][CH2:15][NH:14][C:13]2[CH:18]=[CH:19][C:20]([C:22]([F:25])([F:24])[F:23])=[CH:21][C:12]1=2)[C:8](=[O:10])[CH3:9].[Br:35]Br>CC(O)=O>[F:30][C:29]([F:31])([F:32])[C:27]1[CH:26]=[C:5]([CH:... | CC(=O)N(Cc1cc(C(F)(F)F)cc(C(F)(F)F)c1)C1CCCNc2ccc(C(F)(F)F)cc21 | BrBr | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | 25 | 8 | To a solution of crude N-(3,5-Bis-trifluoromethyl-benzyl)-N-(7-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-acetamide (0.0980 mg, 0.197 mmol) in HOAc (2.00 ml), was added bromine (0.0106 ml, 0.207 mmol) dropwise. The reaction mixture was stirred at room temperature overnight. Remove the solvent on a rotar... | CC(=O)N(Cc1cc(C(F)(F)F)cc(C(F)(F)F)c1)C1CCCNc2c(Br)cc(C(F)(F)F)cc21 | null | 0.1 | null |
978,621 | ord_dataset-f886e51ba1484c76a94bce1482f1eab9 | null | 2010-01-01T00:07:00 | true | Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[CH:13]=[C:14]([CH:21]=[CH:22][C:23]=3[CH3:24])[C:15]([NH:17][CH:18]3[CH2:20][CH2:19]3)=[O:16])=[CH:9][CH:10]=2)[CH:5]=[N:4][N:3]=1.[C:25]1([CH3:34])[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>COCCOC.CCO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=... | Cc1ccccc1B(O)O | Cc1ccc(C(=O)NC2CC2)cc1-c1ccc2c(Cl)nncc2c1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COCCOC | CCO | null | null | null | null | null | null | null | null | null | 90 | 2 | A mixture of 3-(1-chlorophthalazin-6-yl)-N-cyclopropyl-4-methylbenzamide (100 mg, 296 μmol), o-tolylboronic acid (40 mg, 296 μmol) and tetrakis(triphenylphosphine)palladium (17 mg, 15 μmol) in 5 mL DME/EtOH (4:1) was treated with 2M potassium carbonate (444 μl, 888 μmol). The mixture was stirred at 90° C. for 2 h. The ... | Cc1ccc(C(=O)NC2CC2)cc1-c1ccc2c(-c3ccccc3C)nncc2c1 | null | null | null |
1,710,341 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | [CH:1]1([CH2:4][O:5][C:6]2[N:11]=[C:10]([C:12]([OH:14])=O)[CH:9]=[CH:8][C:7]=2[N:15]2[CH2:18][C:17]([F:20])([F:19])[CH2:16]2)[CH2:3][CH2:2]1.Cl.[C@H:22]12[CH2:28][C@H:25]([NH:26][CH2:27]1)[CH2:24][S:23]2.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>>[CH:1]1([CH2:4][O:5][C:6]2[N:11]=[C:10]([C:12]([... | C1S[C@@H]2CN[C@H]1C2 | O=C(O)c1ccc(N2CC(F)(F)C2)c(OCC2CC2)n1 | null | CN(C)C(On1nnc2ccccc21)=[N+](C)C | Cl | F[B-](F)(F)F | 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 | null | null | In analogy to the procedure described in Example 47 b), 6-cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid (Example 1 b)) was reacted with (1S,4S)-2-thia-5-azabicyclo[2.2.1]heptane hydrochloride (125136-43-8) in the presence of TBTU and DIEA to obtain the title compound as colorless oil; MS ... | O=C(c1ccc(N2CC(F)(F)C2)c(OCC2CC2)n1)N1C[C@@H]2C[C@H]1CS2 | null | null | null |
1,711,818 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | [C:1]([O:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][N:21]2[C:25]3[CH:26]=[CH:27][C:28]([C:30](O)=[O:31])=[CH:29][C:24]=3[N:23]=[CH:22]2)=[CH:16][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:33][CH:34]([CH3:39])[CH2:35][CH:36]([NH2:38])[CH3:37].CN(C(ON1N=NC2C=CC=NC1=2)=[N+... | CC(C)CC(C)N | CC(C)(C)OC(=O)c1ccccc1-c1ccc(Cn2cnc3cc(C(=O)O)ccc32)cc1 | null | CN(C)C(On1nnc2cccnc21)=[N+](C)C | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | null | null | The mixture of 1-((2′-(tert-butoxycarbonyl)biphenyl-4-yl)methyl)-1H-benzo[d]imidazole-5-carboxylic acid (45 mg, 0.105 mmol), 4-methylpentan-2-amine (12.7 mg, 0.126 mmol), HATU (78 mg, 0.315 mmol) and DIPEA (27 mg, 0.315 mmol) in 10 mL of DCM was stirred at RTovernight. Then the solvent was removed under the reduced pre... | CC(C)CC(C)NC(=O)c1ccc2c(c1)ncn2Cc1ccc(-c2ccccc2C(=O)OC(C)(C)C)cc1 | null | null | null |
598,507 | ord_dataset-843ef38b45484f72826f5f39d8a29c4d | null | 2003-01-01T00:06:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][N:16]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=3[F:35])[C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[C:18]=3[CH3:26])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[OH:36].[C:37]([O:41][CH2:42][CH3:43])(=[O:40])[CH2:38]O>>[Cl:1]... | CCOC(=O)CO | Cc1c(N(Cc2ccc(Oc3ccc(Cl)c(O)c3)cc2)Cc2ccc(F)cc2F)cccc1[N+](=O)[O-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The product from Example 91F and ethyl glycolate were processed as described in Example 62A to provide the title compound. MS (ESI+) m/z 597 (M+H)+. | CCOC(=O)COc1cc(Oc2ccc(CN(Cc3ccc(F)cc3F)c3cccc([N+](=O)[O-])c3C)cc2)ccc1Cl | null | null | null |
1,680,673 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | [OH:1][CH2:2][C:3]([CH3:25])([CH3:24])[CH2:4][CH2:5][CH2:6][N:7]1[CH2:22][CH:10]2[CH2:11][N:12](C(OC(C)(C)C)=O)[CH2:13][CH2:14][N:9]2[C:8]1=[O:23].C(O)(C(F)(F)F)=O>C(Cl)Cl>[OH:1][CH2:2][C:3]([CH3:25])([CH3:24])[CH2:4][CH2:5][CH2:6][N:7]1[CH2:22][CH:10]2[CH2:11][NH:12][CH2:13][CH2:14][N:9]2[C:8]1=[O:23] | CC(C)(CO)CCCN1CC2CN(C(=O)OC(C)(C)C)CCN2C1=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | 25 | 1 | tert-Butyl 2-(5-hydroxy-4,4-dimethyl-pentyl)-3-oxo-5,6,8,8a-tetrahydro-1H-imidazo[1,5-a]pyrazine-7-carboxylate (Compound 69-B) (1 mmol) was dissolved in CH2Cl2 (3 mL) followed by the slow addition of TFA (1 mL) at 0° C. The reaction mixture was stirred at rt for 1 hour and then the solvent was removed under vacuum to g... | CC(C)(CO)CCCN1CC2CNCCN2C1=O | null | null | null |
220,251 | ord_dataset-6cb04513a4a244c0b612b566096f4b3d | null | 1990-01-01T00:12:00 | true | [CH3:1][C:2]1([CH3:11])[O:7][CH2:6][CH:5]([N+:8]([O-])=O)[CH2:4][O:3]1.C([O-])=O.[NH4+]>CO.[Pd]>[CH3:1][C:2]1([CH3:11])[O:7][CH2:6][CH:5]([NH2:8])[CH2:4][O:3]1 | CC1(C)OCC([N+](=O)[O-])CO1 | null | null | [Pd] | O=C[O-] | [NH4+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | 220 mg 5% Pd/C was added to a solution of 500 mg 2,2-dimethyl-5-nitro-1,3-dioxane (3.1 mmoles) in 30 ml methanol. Ammonium formate (985 mg, 15.6 mmoles) was then added, and the mixture was refluxed for three hours. The reaction solution was then filtered, and the filtrate concentrated in vacuo to yield 286 mg 2,2-dimet... | CC1(C)OCC(N)CO1 | null | 70.3 | null |
1,703,337 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | [F-:1].[Cs+].[C:3]1([S:9][CH2:10]Cl)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C(#N)C>[C:3]1([S:9][CH2:10][F:1])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1 | [F-] | ClCSc1ccccc1 | null | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | null | null | Cesium fluoride (191.50 g, 2 eq) was added to a mixture of PEG400 (100 mL) and acetonitrile (600 mL). The mixture was stirred for a few minutes under an argon atmosphere and then acetonitrile (100 mL) was removed by distillation. Chloromethyl phenyl sulfide (100 g, 630.32 mmol) was added and the resulting mixture was s... | FCSc1ccccc1 | null | 58.5 | null |
7,786 | ord_dataset-653be8036d754ce7b8a1c4cd419eaf55 | null | 1976-01-01T00:05:00 | true | [CH3:1][N:2]1[CH2:7][CH2:6][C:5]2([C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[O:8]2)[CH2:4][CH2:3]1.O1CCC[CH2:23]1.C([Li])CCC.COS(OC)(=O)=O>CCCCCC>[CH3:1][N:2]1[CH2:7][CH2:6][C:5]2([C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([CH3:23])([C:16]3[CH:21]=[CH... | CN1CCC2(CC1)OC(c1ccccc1)c1ccccc12 | C1CCOC1 | null | [Li]CCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COS(=O)(=O)OC | CCCCCC | null | null | null | null | null | null | null | null | null | null | 0.5 | A solution of 1.4 g. of 1,3-dihydro-1'-methyl-3-phenylspiro[isobenzofuran-1,4'-piperidine], (Example 2), in 20 ml. of tetrahydrofuran is cooled to -50° and treated dropwise with 4 ml. of butyllithium in hexane. Stirring is continued for 30 minutes under nitrogen. To the solution is slowly added 900 mg. of dimethylsulfa... | CN1CCC2(CC1)OC(C)(c1ccccc1)c1ccccc12 | null | null | null |
926,629 | ord_dataset-cc0899cd744f4f7f8e7f2463560faad1 | null | 2009-01-01T00:12:00 | true | [CH3:1][C:2]([S:5]([NH2:7])=[O:6])([CH3:4])[CH3:3].[C:8]([O:12][C:13]([N:15]([CH2:32][CH:33]=O)[CH:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[CH2:18][CH2:17]1)=[O:14])([CH3:11])([CH3:10])[CH3:9]>ClC(Cl)C>[C:8]([O:12][C:13]([N:15]([CH2:32]/[CH:33]=[N:7]/[S:5](... | CC(C)(C)OC(=O)N(CC=O)C1CCN(C(=O)OCc2ccccc2)CC1 | CC(C)(C)S(N)=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 50 | 18 | 2-Methyl-2-propanesulfinamide (212 mg, 1.753 mmol) and cupric sulfate monohydrate (849 mg, 4.78 mmol) were added to a solution of benzyl 4-[(tert-butoxycarbonyl)(2-oxoethyl)amino]piperidine-1-carboxylate (600 mg, 1.59 mmol) in dichloroethane (15 mL) and was heated at 50° C. After 18 h, the reaction was filtered, concen... | CC(C)(C)OC(=O)N(C/C=N/S(=O)C(C)(C)C)C1CCN(C(=O)OCc2ccccc2)CC1 | null | null | null |
860,855 | ord_dataset-93908aaae836460ebd48d733eccad483 | null | 2009-01-01T00:01:00 | 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)=[N:2]1.OC1C2N=NNC=2C=CC=1.C(N=C=NC(C)C)(C)C.[S:32]([NH2:42])(=[O:41])([C:34]1[CH:39]=[CH:38][C:37]([NH2:40])=[CH:36][CH:35]=1)=[O:33]>CN(C=O)C>[S:32]([C:34]1[CH:35]=[CH:36][C:37]([NH:40][C:10]([C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][... | Nc1ccc(S(N)(=O)=O)cc1 | O=C(O)c1n[nH]c2ccccc12 | null | CC(C)N=C=NC(C)C | Oc1cccc2[nH]nnc12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 25 | 0.5 | A mixture of indazole-3-carboxylic acid (324 mg, 2 mmol), hydroxybenzotriazole (297 mg, 2.2 mmol) and diisopropylcarbodiimide (344 μl, 2.2 mmol) in DMF (10 ml) is stirred for 30 min at room temperature. Sulphanilamide (380 mg, 2.2 mmol) is added. The reaction mixture is stirred overnight at room temperature and then fi... | NS(=O)(=O)c1ccc(NC(=O)c2n[nH]c3ccccc23)cc1 | null | 101.2 | null |
1,576,240 | 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]([N:15](CC3C=CC(OC)=CC=3OC)[C:16]3[S:17][CH:18]=[CH:19][N:20]=3)(=[O:14])=[O:13])=[CH:9][CH:10]=2)[C:5]([C:32]#[N:33])=[CH:4][N:3]=1.[Cl:34][C:35]1[CH:40]=[CH:39][C:38](B(O)O)=[C:37]([O:44][CH3:45])[CH:36]=1>>[Cl:34][C:35]1[CH:40]=[CH:39][C:38]([C:2]2[C:11]3[C:6](=[CH:7][C:8]([S:... | COc1cc(Cl)ccc1B(O)O | COc1ccc(CN(c2nccs2)S(=O)(=O)c2ccc3c(Cl)ncc(C#N)c3c2)c(OC)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 | Example 241 was synthesized in a similar manner to Example 228, except that 1-chloro-4-cyano-N-(2,4-dimethoxybenzyl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamide and (4-chloro-2-methoxyphenyl)boronic acid were used as the coupling partners. The final compound was purified via column chromatography (12 g silica gel column... | COc1cc(Cl)ccc1-c1ncc(C#N)c2cc(S(=O)(=O)Nc3nccs3)ccc12 | null | null | null |
309,427 | ord_dataset-081613ef79bd4110aacc146b4465f086 | null | 1995-01-01T00:05:00 | true | [CH2:1]([C:5]1[N:6]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[S:36](=[O:39])(=[O:38])[NH2:37])=[CH:26][C:25]=2[F:40])[C:7](=[O:22])[N:8]([C:10]2[CH:15]=[C:14]([NH:16][C:17](=[O:20])[CH2:18][CH3:19])[CH:13]=[CH:12][C:11]=2[Cl:21])[N:9]=1)[CH2:2][CH2:3][CH3:4].[Cl:41][C:42]1[CH:50... | O=C(O)c1ccccc1Cl | CCCCc1nn(-c2cc(NC(=O)CC)ccc2Cl)c(=O)n1Cc1ccc(-c2ccccc2S(N)(=O)=O)cc1F | null | O=C(n1ccnc1)n1ccnc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCC2=NCCCN2CC1 | null | null | null | null | null | null | null | null | null | null | null | null | Following the procedure of Example 51, 5-n-butyl-2-[2-chloro-5-(propionylamino)phenyl]-2,4-dihydro-4-[(3-fluoro-2'-sulfamoylbiphenyl-4-yl)methyl]-3H-1,2,4-triazol-3-one (from Step E) was reacted with 2-chlorobenzoic acid (2 equivalents), CDI (2 equiv), and DBU (2 equiv). Purification of the crude product by flash chrom... | CCCCc1nn(-c2cc(NC(=O)CC)ccc2Cl)c(=O)n1Cc1ccc(-c2ccccc2S(=O)(=O)NC(=O)c2ccccc2Cl)cc1F | null | 65 | null |
1,216,014 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | C(O[CH:4]=[CH:5][C:6](=O)[C:7]([F:10])([F:9])[F:8])C.[CH3:12][S:13][CH2:14][CH:15]=[CH:16][N:17]1CCCC1.C([O-])(=O)C.[NH4+]>C(#N)C>[CH3:12][S:13][CH2:14][C:15]1[CH:4]=[CH:5][C:6]([C:7]([F:8])([F:9])[F:10])=[N:17][CH:16]=1 | CCOC=CC(=O)C(F)(F)F | CSCC=CN1CCCC1 | null | CC(=O)[O-] | [NH4+] | 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 | 0 | 2 | To a dry 1 L round bottom flask equipped with a magnetic stir bar, liquid addition funnel, thermometer, and nitrogen inlet were added 4-ethoxy-1,1,1-trifluorobut-3-en-2-one (M) (67.4 g, 401 mmol) and 133 mL of anhydrous acetonitrile, and the resulting solution was cooled to 0° C. in an ice bath. To this solution was ad... | CSCc1ccc(C(F)(F)F)nc1 | null | 85.2 | null |
571,253 | ord_dataset-5e1b2445a3d94ea592ddf2c284118a1e | null | 2002-01-01T00:11:00 | true | [CH2:1]([O:3][P:4]([C:9]1[CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[CH:16]=2)[CH:12]=[CH:13][CH:14]=1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].C1C(=O)N([Br:29])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:29][CH2:21][C:17]1[CH:16]=[C:15]([C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([P:4]([O:3][... | O=C1CCC(=O)N1Br | CCOP(=O)(OCC)c1cccc(-c2cccc(C)c2)c1 | 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 | 25 | null | To the compound of Step 2 (0.122 g, 0.400 mmol) in CCl4 (5 mL) were added NBS (0.050 g, 0.480 mle) and a catalytic amount of benzoyl peroxide. The reaction mixture was refluxed under light for 2 h. The reaction was cooled to room temperature, filtered and evaporated. The title compound was obtained after purification b... | CCOP(=O)(OCC)c1cccc(-c2cccc(CBr)c2)c1 | null | null | null |
868,533 | ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | null | 2009-01-01T00:03:00 | true | Cl[C:2]1[CH:17]=[C:6]2[C:7]3[C:12]([CH2:13][CH2:14][N:5]2[C:4](=[O:18])[N:3]=1)=[CH:11][C:10]([O:15][CH3:16])=[CH:9][CH:8]=3.[Cl:19][C:20]1[CH:26]=[C:25]([CH3:27])[C:23]([NH2:24])=[C:22]([CH3:28])[CH:21]=1>>[Cl:19][C:20]1[CH:26]=[C:25]([CH3:27])[C:23]([NH:24][C:2]2[CH:17]=[C:6]3[C:7]4[C:12]([CH2:13][CH2:14][N:5]3[C:4](... | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O | Cc1cc(Cl)cc(C)c1N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from 2-chloro-9-methoxy-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one (4) and 4-Chloro-2,6-dimethyl-aniline as in Example 1 d. 1H-NMR (400 MHz, d6-DMSO) δ 8.73 (br, 1H), 7.72 (br, 1H), 7.19 (s, 2H), 7.03-6.95 (2H), 6.36 (br, 1H), 3.95 (t, 2H), 3.85 (s, 3H), 2.96 (t, 2H) and 2.18 (s, 6H); ... | COc1ccc2c(c1)CCn1c-2cc(Nc2c(C)cc(Cl)cc2C)nc1=O | null | null | null |
19,736 | ord_dataset-2a1960001e7d4e89987253631df1362a | null | 1977-01-01T00:02:00 | true | [OH-].[Na+].[Cl:3][C:4]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:5]=1[CH2:6][OH:7].O[C:14]1[CH:22]=[CH:21][C:17]([CH2:18][CH2:19][OH:20])=[CH:16][CH:15]=1.S(=O)(=O)(O)O>C(O)C.O>[Cl:3][C:4]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:5]=1[CH2:6][O:7][C:14]1[CH:22]=[CH:21][C:17]([CH2:18][CH2:19][OH:20])=[CH:16][CH:15]=1 | OCCc1ccc(O)cc1 | OCc1ccc(Cl)cc1Cl | null | O=S(=O)(O)O | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | O | null | null | null | null | null | null | null | null | null | null | null | 2.8 g. of sodium hydroxide in 10 ml. of water and 13.6 g. of 2,4-dichlorobenzyl alcohol are added to 8 g. of 4-hydroxyphenethyl alcohol in 80 ml. of ethanol. After refluxing the solution for 1.5 hours, the mixture is acidified with dilute sulfuric acid and extracted with methylene chloride. Drying and evaporation of th... | OCCc1ccc(OCc2ccc(Cl)cc2Cl)cc1 | null | null | null |
524,373 | ord_dataset-293186f5c9b441cab57f03cd3a18ac26 | null | 2001-01-01T00:11:00 | true | [CH2:1]([O:3][CH:4]([O:12][CH2:13][CH3:14])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1Br)[CH3:2].C([Li])CCC.CN(C)[CH:22]=[O:23].O>C(OCC)C>[CH2:1]([O:3][CH:4]([O:12][CH2:13][CH3:14])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH:22]=[O:23])[CH3:2] | CN(C)C=O | CCOC(OCC)c1ccccc1Br | null | [Li]CCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | O | null | null | null | null | null | null | null | null | null | 25 | 0.5 | To a solution of 10.4 g of 2-bromobenzaldehyde diethyl acetal in 200 ml of dry diethyl ether at −65° C. was added 27.5 ml of a 1.6 M solution of butyllithium in hexanes. The solution was stirred at this temperature for 30 min. then slowly warmed to −40° C. when 3.4 ml of dimethylformamide was added dropwise. The reacti... | CCOC(OCC)c1ccccc1C=O | null | null | null |
911,725 | ord_dataset-c663259b80f947e2a8923796fb0e9a6b | null | 2009-01-01T00:10:00 | true | Br[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[C:7]([NH2:12])[C:6]3[N:13]=[C:14]([CH2:20][O:21][CH2:22][CH3:23])[N:15]([CH2:16][CH2:17][CH2:18][CH3:19])[C:5]=3[C:4]=2[CH:3]=1.[C:24]1(B(O)O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[CH2:16]([N:15]1[C:5]2[C:4]3[CH:3]=[C:2]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH:11]=[CH:1... | CCCCn1c(COCC)nc2c(N)nc3ccc(Br)cc3c21 | OB(O)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 8-Bromo-1-butyl-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-4-amine and benzeneboronic acid were coupled according to the general procedure described in Part J of Example 1. Chromatography on silica gel (10% methanol in CH2Cl2) followed by recrystallization from isopropanol afforded 1-butyl-2-ethoxymethyl-8-phenyl-1H-imid... | CCCCn1c(COCC)nc2c(N)nc3ccc(-c4ccccc4)cc3c21 | null | null | null |
89,213 | ord_dataset-aeb5378e6e67443e8a4f5c7a5ec3de51 | null | 1981-01-01T00:12:00 | true | [Br:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][CH2:8][OH:9])=[CH:4][CH:3]=1.[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>O.C(Cl)Cl>[O:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[O:9][CH2:8][CH2:7][O:6][C:5]1[CH:10]=[CH:11][C:2]([Br:1])=[CH:3][CH:4]=1 | C1=COCCC1 | OCCOc1ccc(Br)cc1 | null | Cc1ccc(S(=O)(=O)O)cc1 | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 72 | To a mixture of 12.0 g (55.4 mmol) 2-(4-bromophenoxy)ethanol, 100 ml dry methylene chloride and 5.1 g (60.9 mmol) dihyropyran is added, at RT, 0.42 g (2.2 mmol) p-toluenesulfonic acid.water. The mixture is stirred for 3 days at RT, after which 50 ml methylene chloride, 50 ml water and 10 ml aqueous 15% potassium carbon... | Brc1ccc(OCCOC2CCCCO2)cc1 | null | null | null |
791,008 | ord_dataset-530502f8e61e455784f93c5faa45c94b | null | 2007-01-01T00:09:00 | true | [CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:13]=[C:14]3[C:19](=[C:20]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24](C#N)[CH:23]=4)[N:21]=2)[N:18]=[CH:17][CH:16]=[CH:15]3)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[F:30][C:31]([F:58])([F:57])[O:32]C1C=C(C2N=C(OS(C(F)(F)F)(=O)=O)C=C3C=2N=CC=C3)C=CC=1>>[CH2:1]([O:3][C:4]([CH:6... | O=S(=O)(Oc1cc2cccnc2c(-c2cccc(OC(F)(F)F)c2)n1)C(F)(F)F | CCOC(=O)C1CCC(c2cc3cccnc3c(-c3cccc(C#N)c3)n2)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 | This compound is prepared in an analogous way to compound 4-[8-(3-cyano-phenyl)-[1,7]naphthyridin-6-yl]-cyclohexanecarboxylic acid ethyl ester from trifluoromethanesulfonic acid 8-(3-trifluromethoxyphenyl)-[1,7]naphthyridin-6-yl ester. Purification is by chromatography followed by trituration with ether to yield a whit... | CCOC(=O)C1CCC(c2cc3cccnc3c(-c3cccc(OC(F)(F)F)c3)n2)CC1 | null | null | null |
773,647 | ord_dataset-8214eb8444a44dc2900ccb42dbeff15e | null | 2007-01-01T00:05:00 | true | [F:1][C:2]([F:14])([F:13])[C:3]1[CH:12]=[CH:11][C:6]([C:7]([NH:9][NH2:10])=[O:8])=[CH:5][CH:4]=1.[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.S(=O)(=O)(O)O>CO>[CH:15](=[N:10][NH:9][C:7](=[O:8])[C:6]1[CH:11]=[CH:12][C:3]([C:2]([F:13])([F:14])[F:1])=[CH:4][CH:5]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]... | O=Cc1ccccc1 | NNC(=O)c1ccc(C(F)(F)F)cc1 | null | O=S(=O)(O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | 1 | To a solution (50 ml) of 4-trifluoromethylbenzohydrazide (3.06 g) and benzaldehyde (1.52 ml) in methanol was added dropwise conc. sulfuric acid (0.5 ml), and this mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated, and the residue was washed with hexane-ethanol (1:1, volume ratio) a... | O=C(NN=Cc1ccccc1)c1ccc(C(F)(F)F)cc1 | null | 74 | null |
1,534,843 | ord_dataset-8d5c200bca27407ab9febe7598e16458 | null | 2015-01-01T00:01:00 | true | [F:1][C:2]1[CH:3]=[C:4]([C@H:9]2[CH2:13][CH2:12][CH2:11][N:10]2[C:14]2[CH:19]=[CH:18][N:17]3[N:20]=[CH:21][C:22]([C:23]([O:25][CH2:26][CH2:27]Cl)=[O:24])=[C:16]3[N:15]=2)[C:5](=[O:8])[NH:6][CH:7]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:5](=[N:6][CH:7]=1)[O:8][CH2:27][CH2:26][O:25][C:23](=[O:24... | O=C(OCCCl)c1cnn2ccc(N3CCC[C@@H]3c3cc(F)c[nH]c3=O)nc12 | null | null | O=C([O-])[O-] | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 90 | null | A mixture of (R)-2-chloroethyl 5-(2-(5-fluoro-2-oxo-1,2-dihydropyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate (54 mg, 0.133 mmol) and Cs2CO3 (217 mg, 0.665 mmol) in DMF (6 mL) was heated at 90° C. overnight. The reaction was filtered (GF/F paper) and directly purified by reverse phase column chrom... | O=C1OCCOc2ncc(F)cc2[C@H]2CCCN2c2ccn3ncc1c3n2 | null | null | null |
1,437,392 | ord_dataset-275a3da8f45f4536ad29727f0ef9ba66 | null | 2014-01-01T00:06:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:28]=[CH:29][C:30]=1[O:31][CH3:32])[CH2:6][N:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([OH:18])[CH:14]=2)[N:9]([CH:19]2[CH2:24][CH2:23][N:22]([CH:25]=[O:26])[CH2:21][CH2:20]2)[C:8]1=[O:27].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:40][C:41]#[N:42]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4... | COc1ccc(Cn2c(=O)c3cc(O)ccc3n(C3CCN(C=O)CC3)c2=O)cc1OC | N#CCBr | null | O=C([O-])[O-] | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | null | 0.17 g of 4-[3-(3,4-dimethoxybenzyl)-6-hydroxy-2,4-dioxo-3,4-dihydroquinazolin-1(2H)-yl]piperidine-1-carbaldehyde obtained in stage 1.8 and 0.25 g of Cs2CO3 in 3 ml of DMF are stirred for 15 min at AT. 0.056 g of bromoacetonitrile is added and the reaction mixture is subsequently irradiated under a microwave field at 1... | COc1ccc(Cn2c(=O)c3cc(OCC#N)ccc3n(C3CCN(C=O)CC3)c2=O)cc1OC | null | 60.5 | null |
1,598,965 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [F:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1B1OC(C)(C)C(C)(C)O1)[O:5][C:6]1[CH:11]=[C:10]([CH3:12])[N:9]=[C:8]([CH3:13])[CH:7]=1.C([O-])(O)=O.[Na+].Br[C:32]1[CH:37]=[CH:36][N:35]([CH2:38][CH:39]2[CH2:41][CH2:40]2)[C:34](=[O:42])[C:33]=1[C:43]#[N:44]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(... | N#Cc1c(Br)ccn(CC2CC2)c1=O | Cc1cc(Oc2ccc(B3OC(C)(C)C(C)(C)O3)c(F)c2)cc(C)n1 | 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 | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | null | To a solution of intermediate 18 (1.05 mmol) in 1,4-dioxane (4.5 ml) and a saturated solution of NaHCO3 (4.5 ml) was added intermediate 5 (0.22 g, 0.892 mmol). The resulting solution was degassed using a stream of nitrogen and to this was added Pd(PPh3)4 (0.13 mg, 0.114 mmol). The reaction was then microwaved in a seal... | Cc1cc(Oc2ccc(-c3ccn(CC4CC4)c(=O)c3C#N)c(F)c2)cc(C)n1 | null | null | null |
934,892 | ord_dataset-d8a5dc784dde4465894ec7c69d2e3ba6 | null | 2010-01-01T00:01:00 | true | [CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[N:10]([CH:21]([CH:33]([CH3:35])[CH3:34])[C:22]([NH:24][O:25]CC2C=CC=CC=2)=[O:23])[C:9]1=[O:36])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd].[O-]S([O-])(=O)=O.[Ba+2].CO>[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][C:16]... | COc1ccc(C2CN(Cc3ccccc3)C(=O)N2C(C(=O)NOCc2ccccc2)C(C)C)cc1 | null | null | [Pd] | O=S(=O)([O-])[O-] | [Ba+2] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | 4 | 2-(3-Benzyl-5-(4-methoxyphenyl)-2-oxoimidazolidin-1-yl)-N-benzyloxy-3-methylbutyramide (120 mg; 0.24 mmol) was introduced into methanol (10 ml), and Pd/BaSO4 (50 mg) was added. The mixture was hydrogenated with H2 (1 atm) at RT for 4 h. The reaction mixture was then filtered through kieselguhr, the residue was washed w... | COc1ccc(C2CN(Cc3ccccc3)C(=O)N2C(C(=O)NO)C(C)C)cc1 | null | 62.5 | null |
511,270 | ord_dataset-85c00026681b46f89ef8634d2b8618c3 | null | 2001-01-01T00:07:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[N:13]=[C:12]([C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)[N:11]([CH3:19])[N:10]=1.[Br:20]Br.C(=O)(O)[O-].[Na+]>C(O)(=O)C>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[C:9]1[N:13]=[C:12]([C:14]2[S:15][C:16]([Br:20])=[CH:17][CH:18]=2)[N:11]([CH3:19])[N:10]=1 | Cn1nc(-c2c(Cl)cccc2Cl)nc1-c1cccs1 | BrBr | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | 25 | 8 | 3-(2,6-dichlorophenyl)-5-(thien-2-yl)-1-methyl-[1,2,4]triazole (75 mg, 0.242 mmol) and bromine (39 mg, 0.242 mmol) were combined in glacial acetic acid (3mL) and the mixture was stirred overnight at room temperature, then heated to 95° C. for five hours. The reaction mixture was poured into a saturated sodium bicarbona... | Cn1nc(-c2c(Cl)cccc2Cl)nc1-c1ccc(Br)s1 | null | null | null |
1,172,862 | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | null | 2012-01-01T00:05:00 | true | Br[CH2:2][CH2:3][CH2:4][CH2:5]Br.[Mg].[O:8]1[CH2:11][CH2:10][C:9]1=[O:12]>C1COCC1.II>[OH:8][CH2:11][CH2:10][C:9]1([OH:12])[CH2:5][CH2:4][CH2:3][CH2:2]1 | BrCCCCBr | O=C1CCO1 | null | II | [Mg] | 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 | 12 | A solution of 1,4-dibromobutane (10 g, 46 mmol) in THF (100 mL) was treated with magnesium (2.81 g, 116 mmol) and I2 (100 mg). The mixture was stirred at room temperature for 3 hours a solution of oxetan-2-one (3.34 g, 46.3 mmol) in THF (25 mL) was added dropwise. The reaction mixture was stirred at room temperature fo... | OCCC1(O)CCCC1 | null | 18.4 | null |
1,524,990 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | Br.Br[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.BrCC1CCCCO1.[NH:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]2([C:38]3[CH:37]=[C:36]4[C:31]([N:32]=[CH:33][CH:34]=[N:35]4)=[CH:30][C:29]=3[O:28][CH2:27]2)[C:19]1=[O:39]>>[N:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH2:3][N:35]1[C:36]2[C:31](=[CH:30][C:29]3[O:2... | BrCc1ccccn1 | O=C1Nc2ccccc2C12COc1cc3nccnc3cc12 | null | Br | BrCC1CCCCO1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Following the procedure as described in EXAMPLE 4 and making non-critical variations using 2-(bromomethyl)pyridine hydrobromide to replace 2-(bromomethyl)tetrahydro-2H-pyran, and 7H-spiro[furo[2,3-g]quinoxaline-8,3′-indolin]-2′-one to replace 5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2″(1′H)-one, 1-(pyrid... | O=C1Nc2ccccc2C12COc1cc3c(cc12)N(Cc1ccccn1)CC=N3 | null | null | null |
513,901 | ord_dataset-41760195182e4bb4bc779bd722456071 | null | 2001-01-01T00:08:00 | true | [NH2:1][C:2]1[S:6][C:5]2[CH:7]=[CH:8][C:9]([CH3:11])=[CH:10][C:4]=2[C:3]=1[C:12]([O:14][CH3:15])=[O:13].F[C:17]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=1[N+:24]([O-:26])=[O:25]>CS(C)=O>[F:23][C:21]1[CH:20]=[CH:19][C:18]([N+:24]([O-:26])=[O:25])=[C:17]([CH:22]=1)[NH:1][C:2]1[S:6][C:5]2[CH:7]=[CH:8][C:9]([CH3:11])=[C... | O=[N+]([O-])c1ccc(F)cc1F | COC(=O)c1c(N)sc2ccc(C)cc12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | In the same manner as in Starting Material Synthesis Example 4 and using methyl 2-amino-5-methylbenzo[b]thiophene-3-carboxylate (3.11 g), 2,4-difluoronitrobenzene (1.54 ml) and dimethyl sulfoxide (30 ml), methyl 2-(5-fluoro-2-nitroanilino)-5-methylbenzo[b]thiophene-3-carboxylate was obtained. | COC(=O)c1c(Nc2cc(F)ccc2[N+](=O)[O-])sc2ccc(C)cc12 | null | null | null |
1,593,517 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [F:1][C:2]1[CH:3]=[C:4]([CH2:19][OH:20])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:10]=[N:11][CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=1.Cl[C:22]1[CH:23]=[C:24]2[N:31]([CH3:32])[C@@H:30]([CH3:33])[CH2:29][N:25]2[C:26](=[O:28])[N:27]=1>>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:10]=[N:11][CH:12]=[C:13... | OCc1ccc(Oc2cncc(C(F)(F)F)c2)c(F)c1 | C[C@H]1Cn2c(cc(Cl)nc2=O)N1C | null | null | null | null | null | null | null | 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 by a procedure similar to that described for E9 starting from (3-fluoro-4-((5-(trifluoromethyl)pyridin-3-yl)oxy)phenyl)methanol and (S)-7-chlo-ro-1,2-dimethyl-2,3-dihydroimidazo[1,2-c]pyrimidin-5(1H)-one. | C[C@H]1Cn2c(cc(OCc3ccc(Oc4cncc(C(F)(F)F)c4)c(F)c3)nc2=O)N1C | null | null | null |
1,214,934 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | N#N.[Br:3][C:4]1[N:9]=[C:8]([C:10](=[O:12])[CH3:11])[CH:7]=[CH:6][CH:5]=1.[CH2:13](O)[CH2:14][OH:15].COC(OC)OC.C([O-])([O-])=O.[Na+].[Na+]>>[Br:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([C:10]2([CH3:11])[O:15][CH2:14][CH2:13][O:12]2)[N:9]=1 | CC(=O)c1cccc(Br)n1 | OCCO | null | N#N | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COC(OC)OC | null | null | null | null | null | null | null | null | null | null | 95 | null | In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 1-(6-bromo-pyridin-2-yl)-ethanone (1880 mg, 9.40 mmol) in ethylene glycol (10.00 mL, 179.32 mmol) was treated with trimethylorthoformate (2.10 mL, 19.16 mmol) followed by LiBF4 (180 mg, 1.88 mmol). The... | CC1(c2cccc(Br)n2)OCCO1 | null | null | null |
860,699 | ord_dataset-93908aaae836460ebd48d733eccad483 | null | 2009-01-01T00:01:00 | true | [C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[CH3:6][C:7]1[CH:12]2[C:13]([CH3:15])([CH3:14])[CH:10]([CH2:11]2)[CH2:9][CH:8]=1>C(Cl)CCl.[Cl-].[Zn+2].[Cl-]>[C:13]([C:10]12[CH2:11][CH:12]([C:7]([CH3:6])=[CH:8][CH2:9]1)[C:1](=[O:4])[CH2:2][CH2:3]2)([CH3:15])=[CH2:14] | CC1=CCC2CC1C2(C)C | C=CC(=O)Cl | null | [Cl-] | [Zn+2] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCCl | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 20.0 g acryloyl chloride (0.22 mol) and 3.01 g zinc chloride (0.02 ml, 0.1 eq.) in 150 ml ethylene chloride was treated with a soln. of 350 ml α-pinene ((1S-(−)/(1R)-(+) 90:10, 2.20 mol, 10 eq.) in 250 ml ethylene chloride and the resulting mixture was stirred 1 h at 25° C. and 4 h at 50° C. After cooling,... | C=C(C)C12CC=C(C)C(C1)C(=O)CC2 | null | 0.8 | null |
632,958 | ord_dataset-de283386b8034acd99fba96d3c7d3227 | null | 2004-01-01T00:04:00 | true | [CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][CH:13]2[O:26][C:17]3=[C:18]4[C:23](=[CH:24][CH:25]=[C:16]3[CH:15]=[CH:14]2)[N:22]=[CH:21][CH:20]=[CH:19]4)(=[O:10])=[O:9])=[CH:4][CH:3]=1>[Pd].C(O)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][CH:13]2[O:26][C:17]3=[C:18]4[C:23](=[CH:24][CH:25]=[C:16]3[CH2:15... | Cc1ccc(S(=O)(=O)OCC2C=Cc3ccc4ncccc4c3O2)cc1 | 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 | Treatment of 2H-pyrano[2,3-f]quinolin-2-yl-methyl 4-methylbenzene-sulfonate with palladium on carbon (10 wt. %) in ethanol following the procedure described for Example 1c affords 3,4-dihydro-2H-pyrano[2,3-f]quinolin-2-ylmethyl 4-methylbenzenesulfonate. | Cc1ccc(S(=O)(=O)OCC2CCc3ccc4ncccc4c3O2)cc1 | null | null | null |
422,564 | ord_dataset-1a231de00bfe4443b547e1f03885ed41 | null | 1999-01-01T00:01:00 | true | [I-:1].[Na+].[C:3]1([CH2:9][CH2:10][CH2:11][CH2:12]Cl)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CC(C)=O>[C:3]1([CH2:9][CH2:10][CH2:11][CH2:12][I:1])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1 | [I-] | ClCCCCc1ccccc1 | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | null | null | null | null | null | null | null | null | null | null | 70 | null | Sodium iodide (8.9 g, 59.2 mol) and 4-phenyl-1-chlorobutane (5.0 g, 29.6 mol) were added to acetone (29.6 mL) at rt. The mixture was heated to 70° C. for 12 h. The resulting solution was gravity filtered to remove salts. The solvent was removed under reduced pressure and excess salts were dissolved in water (100 mL). H... | ICCCCc1ccccc1 | null | 0.1 | null |
1,687,402 | ord_dataset-c1e70ad912eb438f8d34b1dc681f809a | null | 2016-01-01T00:02:00 | true | Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][C@@H:10]2[CH3:15])[N:3]=1.[CH2:16]([NH:18][C:19](=[O:36])[NH:20][C:21]1[CH:26]=[CH:25][C:24](B2OC(C)(C)C(C)(C)O2)=[CH:23][CH:22]=1)[CH3:17].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O>[Cl:8][C:6]1[N:5]=[C:4]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][C@@... | CCNC(=O)Nc1ccc(B2OC(C)(C)C(C)(C)O2)cc1 | C[C@H]1COCCN1c1nc(Cl)cc(Cl)n1 | null | O=C([O-])[O-] | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | O | null | null | null | null | null | null | null | null | null | null | null | (S)-4-(4,6-dichloropyrimidin-2-yl)-3-methylmorpholine (Intermediate 1B) (992 mg, 4.0 mmol), 4-(3-ethylureido)phenyl boronic acid pinacol ester (1.05 g, 3.6 mmol), cesium carbonate (3.9 g, 12.0 mmol) and bis(diphenylphosphino)-ferrocenedichloropalladium(II)-DCM-complex (163 mg, 0.2 mmol) in dioxane/water (1:3, 2.4 mL) w... | CCNC(=O)Nc1ccc(-c2cc(Cl)nc(N3CCOC[C@@H]3C)n2)cc1 | null | null | null |
810,732 | ord_dataset-da49b0378abf41bf92ab8ecdd3feb28b | null | 2008-01-01T00:02:00 | true | [C:1]([O:5][C:6]([N:8]([CH3:22])[CH:9]1[CH2:14][CH2:13][C:12](=[CH:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[O-].[Na+]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]([CH3:22])[C@H:9]1[CH2:10][CH2:11][C@H:12]([CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH2:13][CH2... | CN(C(=O)OC(C)(C)C)C1CCC(=CCCCC(=O)O)CC1 | null | null | [Pd] | C[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | 5.0 g (16.1 mmol) 5-[4-(tert-Butoxycarbonyl-methyl-amino)-cyclohexylidene]-pentanoic acid in 50 ml methanol were hydrogenated with 0.5 g 10% Pd/C in the presence of 0.94 ml (16.9 mmol, 1.05 eq) sodium methanolate for 1 h at RT. After filtration and evaporation of the solvent, the residue was dissolved in ether and acid... | CN(C(=O)OC(C)(C)C)[C@H]1CC[C@H](CCCCC(=O)O)CC1 | null | null | null |
1,542,683 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | [F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].[CH:12]#[C:13][CH2:14]Br.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH2:14]([O:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:2]([F:10])([F:11])[F:1])[C:13]#[CH:12] | C#CCBr | Oc1ccccc1C(F)(F)F | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | 25 | 8 | To a stirred solution of 2-(trifluoromethyl)phenol (50.0 g, 0.31 mol) and progargyl bromide (44.0 g, 0.37 mol) in ACN (500 mL) was added K2CO3 (51.0 g, 0.37 mol) and the mixture was stirred overnight at rt, concentrated, diluted with water and extracted with Et2O. The combined organic layers were dried over Na2SO4, fil... | C#CCOc1ccccc1C(F)(F)F | null | null | null |
1,238,587 | ord_dataset-e96f5a2842f14e5380461c234100f05a | null | 2012-01-01T00:12:00 | true | [O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]([C:11]2[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=2)[CH:14]=[O:15])[N:9]=[C:8]([C:19]([F:22])([F:21])[F:20])[CH:7]=1.[CH2:23](O)[CH2:24][CH2:25][OH:26].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[O:15]1[CH2:23][CH2:24][CH2:25][O:26][CH:14]1[C:13]1[CH:12]=[C:11]([N:10]2[C:6]([C:2... | O=Cc1cccc(-n2nc(C(F)(F)F)cc2-c2ccco2)c1 | OCCCO | null | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | To a stirred solution of 122 (3.25 g, 10.62 mmol) in PhMe (53 ml) was added 1,3-propanediol (1.616 g, 21.24 mmol) followed by p-toluenesulfonic acid monohydrate (0.202 g, 1.062 mmol) and the resulting solution was allowed to stir at reflux with a Dean-Stark trap for 16 h. The solution was evaporated to dryness, and sat... | FC(F)(F)c1cc(-c2ccco2)n(-c2cccc(C3OCCCO3)c2)n1 | null | 78.5 | null |
956,863 | ord_dataset-ed65749688da45af8a8432967b017729 | null | 2010-01-01T00:05:00 | true | F[C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[C:4]([OH:9])[CH:3]=1>S(=O)(=O)(O)O>[OH:9][C:4]1[CH:5]=[C:6]2[C:7]([CH:4]=[CH:5][C:6](=[O:8])[O:8]2)=[CH:2][CH:3]=1 | Oc1cc(O)cc(F)c1 | null | null | O=S(=O)(O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 0 | 24 | 1-Fluoro-3,5-dihydroxybenzene (1.0 g, 7.8 mmol) and ethyl 2-benzyl acetoacetate 1.72 g, 7.8 mmol) are suspended in 20 mL of 70% sulfuric acid at room temperature. The reaction mixture is stirred for 24 hours and poured into ice water. The solid is filtered and washed with water. The yellowish crude product is re-crysta... | O=c1ccc2ccc(O)cc2o1 | null | 146.9 | null |
1,388,938 | ord_dataset-31641fb65b34430fa7435229b949b604 | null | 2014-01-01T00:01:00 | true | ClC1C=C(C=CC=1)C(OO)=[O:6].[CH3:12][C:13]([CH3:45])([CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:34]=[C:33]3[C:28]([C:29]([C:36](=[O:44])[NH:37][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)=[CH:30][C:31]([CH3:35])=[N:32]3)=[CH:27][CH:26]=2)=[CH:21][N:20]=1)[C:14]([OH:16])=[O:15]>C(Cl)Cl>[C:14]([C:13]([CH3:45... | O=C(OO)c1cccc(Cl)c1 | Cc1cc(C(=O)Nc2ccccc2)c2ccc(-c3ccc(OCC(C)(C)C(=O)O)nc3)cc2n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 8 | m-Chloroperoxybenzoic acid (30.0 mg, 0.20 mmol) was added at room temperature to a solution of 2,2-dimethyl-3-(5-(2-methyl-4-(phenylcarbamoyl)quinolin-7-yl)pyridin-2-yloxy)propanoic acid B-17 (45.5 mg, 0.10 mmol) in methylene chloride (7 mL). The reaction mixture was stirred at room temperature overnight, then concentr... | Cc1cc(C(=O)Nc2ccccc2)c2ccc(-c3ccc(OCC(C)(C)C(=O)O)nc3)cc2[n+]1[O-] | null | 40 | null |
1,626,744 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | [CH:1]1([C:4]([C:6]2[CH:7]=[N:8][C:9]3[C:14]([C:15]=2[NH:16][C:17]2[CH:18]=[N:19][C:20]([N:23]4[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24]4)=[N:21][CH:22]=2)=[CH:13][C:12]([C:36]2[CH:41]=[C:40]([Cl:42])[C:39]([OH:43])=[C:38]([Cl:44])[CH:37]=2)=[CH:11][CH:10]=3)=[O:5])[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>>[CH:1]1... | CC(C)(C)OC(=O)N1CCN(c2ncc(Nc3c(C(=O)C4CC4)cnc4ccc(-c5cc(Cl)c(O)c(Cl)c5)cc34)cn2)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | Following general procedure A-2, tert-butyl 4-(5-((3-(cyclopropanecarbonyl)-6-(3,5-dichloro-4-hydroxyphenyl)quinolin-4-yl)amino)pyrimidin-2-yl)piperazine-1-carboxylate (0.10 mmol) was reacted with TFA (2 mL) to afford the desired product (7.4 mg, 14% over two steps) as a yellow solid. 1H NMR (500 MHz, MeOD) δ 9.24 (s, ... | O=C(c1cnc2ccc(-c3cc(Cl)c(O)c(Cl)c3)cc2c1Nc1cnc(N2CCNCC2)nc1)C1CC1 | null | 13.8 | null |
1,275,106 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | P(Br)(Br)[Br:2].[Cl:5][C:6]1[C:7]([CH3:14])=[C:8]([CH2:12]O)[CH:9]=[CH:10][CH:11]=1>C1(C)C=CC=CC=1>[Br:2][CH2:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([Cl:5])[C:7]=1[CH3:14] | BrP(Br)Br | Cc1c(Cl)cccc1CO | 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 | 25 | 8 | To a solution of phosphorus tribromide (0.422 mL, 4.47 mmol) in Toluene (30 mL) was added (3-chloro-2-methylphenyl)methanol (2 g, 12.77 mmol). The reaction was stirred at RT overnight. The solvent was removed and the residue was partitioned between EtOAc and brine. The organic layer was concentrated and the residue was... | Cc1c(Cl)cccc1CBr | null | 203.8 | null |
1,731,159 | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | null | 2016-01-01T00:05:00 | true | [CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[OH:10]>C(Cl)Cl.O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([C:5]2[C:4]([OH:10])=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([CH3:9])[CH:6]=2)[C:4]=1[OH:10] | COc1cc(C)ccc1O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O | null | null | null | null | null | null | null | null | null | 0 | 1 | Bu3MeNMnO4 (10.9 g, 34.1 mmol) was dissolved in CH2Cl2 (250 mL) placed in an ice bath and allowed to cool. Then 2-methoxy-4-methylphenol (9.95 g, 72.0 mmol) was added dropwise to the CH2Cl2 solution and allowed to react with stirring for 1 h at 0° C. under N2. The reaction mixture was diluted with H2O (˜200 mL) and the... | COc1cc(C)cc(-c2cc(C)cc(OC)c2O)c1O | null | 60.5 | null |
107,428 | ord_dataset-29d79fca4cec4a43b773d0ba25b27651 | null | 1983-01-01T00:08:00 | true | [C:1]([C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8](Cl)=[C:7]([N+:15]([O-:17])=[O:16])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[O:18]1[CH2:22][CH2:21][O:20][CH:19]1[CH2:23][NH:24][CH2:25][CH3:26].C1(C)C=CC=CC=1>C(OCC)C>[CH2:25]([N:24]([CH2:23][CH:19]1[O:20][CH2:21][CH2:22][O:18]1)[C:8]1[C:9]([N+:11]([O-:13])=[O:12])=[CH:... | CC(C)(C)c1cc([N+](=O)[O-])c(Cl)c([N+](=O)[O-])c1 | CCNCC1OCCO1 | null | null | null | 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 | 90 | 72 | 4-t-Butyl-2,6-dinitrochlorobenzene (1.8 grams; 0.007 mole), N-(1,3-dioxolan-2-yl)methyl ethylamine (1.83 grams; 0.014 mole) and toluene (50 ml) were placed in a glass reaction vessel equipped with a stirrer, heating mantle, reflux condenser and thermometer. The reaction mixture was heated to 90° C. and maintained at th... | CCN(CC1OCCO1)c1c([N+](=O)[O-])cc(C(C)(C)C)cc1[N+](=O)[O-] | null | 68.7 | null |
1,745,862 | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | null | 2016-01-01T00:07:00 | true | Br[C:2]1[C:10]2[C:9]([NH:11][C@H:12]([C:14]3[N:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:18](=[O:26])[C:17]4=[C:27]([CH3:30])[CH:28]=[CH:29][N:16]4[N:15]=3)[CH3:13])=[N:8][CH:7]=[N:6][C:5]=2[N:4](COCC[Si](C)(C)C)[CH:3]=1.[OH:39][C:40]1[CH:41]=[C:42]([NH:55][S:56]([C:59]2[CH:64]=[CH:63][C:62]([O:65][CH3:66])... | Cc1ccn2nc([C@H](C)Nc3ncnc4c3c(Br)cn4COCC[Si](C)(C)C)n(-c3ccccc3)c(=O)c12 | COc1ccc(S(=O)(=O)Nc2cc(O)cc(B3OC(C)(C)C(C)(C)O3)c2)cc1 | null | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COCCOC | O | null | null | null | null | null | null | null | null | null | null | null | (S)-2-(1-((5-Bromo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (70 mg, 0.12 mmol) was treated with N-(3-hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4-methoxybenzenesulfonamide (229 mg, 0.57 mmol), sodium car... | COc1ccc(S(=O)(=O)Nc2cc(O)cc(-c3c[nH]c4ncnc(N[C@@H](C)c5nn6ccc(C)c6c(=O)n5-c5ccccc5)c34)c2)cc1 | null | 33 | null |
972,090 | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | null | 2010-01-01T00:06:00 | true | Cl.[C:2](=[NH:9])([NH2:8])[CH2:3][CH2:4][CH2:5][CH:6]=[CH2:7].[C:10]1([C:16]#[C:17][CH:18]=O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[CH2:3]([C:2]1[N:8]=[C:16]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:17]=[CH:18][N:9]=1)[CH2:4][CH2:5][CH:6]=[CH2:7] | C=CCCCC(=N)N | O=CC#Cc1ccccc1 | null | Cl | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 5-hexenimidamide hydrochloride (P4, 500 mg), 3-phenyl-2-propynal (398 mg), and sodium carbonate (786 mg) in acetonitrile (15 mL) was irradiated in a microwave synthesizer at 120° C. for 40 min and then allowed to cool. The solution was filtered and evaporated in vacuo. The residue was dissolved in dichloro... | C=CCCCc1nccc(-c2ccccc2)n1 | null | 20.7 | null |
1,243,138 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[OH:11][C:12]1[CH:13]=[C:14]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH:15]=[CH:16][C:17]=1[CH3:18].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:18][C:17]1[CH:16]=[CH:15][C:14]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:25])[CH3:2... | Cc1ccc(NC(=O)OC(C)(C)C)cc1O | O=[N+]([O-])c1ccc(Cl)nc1 | 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 | 70 | 18 | To a solution of 2-chloro-5-nitropyridine (15.0 g, 94.5 mmol) and tert-butyl (3-hydroxy-4-methylphenyl)carbamate (20.0 g, 90.0 mmol) in N,N-dimethylformamide (200 mL) was added potassium carbonate (18.6 g, 135 mmol), and the mixture was stirred at 70° C. for 18 hr. The reaction mixture was cooled to room temperature, t... | Cc1ccc(NC(=O)OC(C)(C)C)cc1Oc1ccc([N+](=O)[O-])cn1 | null | 92 | null |
813,248 | ord_dataset-892acf7477db4d3a8a8559f004a7c0a2 | null | 2008-01-01T00:03:00 | true | [CH2:1]([O:3][C:4](=[O:18])/[C:5](/[OH:17])=[CH:6]/[C:7]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][N:10]=[C:9](Cl)[CH:8]=1)[CH3:2].[CH:19]1([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH2:23][CH2:22][CH2:21][CH2:20]1>CN(C=O)C.C([O-])(O)=O.[Na+]>[CH2:1]([O:3][C:4](=[O:18])/[C:5](/[OH:17])=[CH:6]/[C:7]1[C:12]([N+:13](... | C1CCC(N2CCNCC2)C1 | CCOC(=O)/C(O)=C/c1cc(Cl)ncc1[N+](=O)[O-] | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 110 | null | A mixture of 3.16 g (Z)-3-(2-chloro-5-nitro-pyridin-4-yl)-2-hydroxy-acrylic acid ethyl ester in 40 mL DMF was treated with 2.96 g (192 mmol) 1-cyclopentyl-piperazine and heated to 110° C. for 1.5 h. The mixture was diluted with 1N NaHCO3 aq. and extracted with DCM. The combined organic layers were dried with MgSO4 and ... | CCOC(=O)/C(O)=C/c1cc(N2CCN(C3CCCC3)CC2)ncc1[N+](=O)[O-] | null | null | null |
739,230 | ord_dataset-437aa6654d5044ddaef3346dc4c6e08a | null | 2006-01-01T00:11:00 | true | [CH2:1]([C:5]1[N:9]=[C:8]([CH2:10][CH2:11][CH2:12][CH3:13])[N:7]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[C:22]([C:27]([O:29]C)=[O:28])=[CH:23][CH:24]=[CH:25][CH:26]=3)=[CH:17][CH:16]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+]>C(O)C>[CH2:1]([C:5]1[N:9]=[C:8]([CH2:10][CH2:11][CH2:12][CH3:13])[N:7]([CH2:14][C:15]2[C... | CCCCc1nc(CCCC)n(Cc2ccc(-c3ccccc3C(=O)OC)cc2)n1 | 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 | null | A 2.0 g (4.9 mmol) sample of the methyl ester product compound from Example 1 was dissolved in 80 ml of ethanol and treated with 80 ml of 10% NaOH at ambient temperature for 3 days. The ethanol was removed in vacuo and the aqueous phase acidified to pH 1 with hydrochloric acid which caused the product to precipitate; f... | CCCCc1nc(CCCC)n(Cc2ccc(-c3ccccc3C(=O)O)cc2)n1 | null | 86 | null |
1,008,507 | ord_dataset-7448b89163bf426c9d9777809ce24cec | null | 2010-01-01T00:11:00 | true | [N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2([OH:19])[CH2:16][CH:15]3[CH2:17][CH2:18][CH:8]2[CH2:9][C:10]23OCC[O:11]2)[CH:2]=1.Cl>C1COCC1.C([O-])(O)=O.[Na+].O>[OH:19][C:7]1([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[CH2:16][CH:15]2[CH2:17][CH2:18][CH:8]1[CH2:9][C:10]2=[O:11] | OC1(c2cccnc2)CC2CCC1CC21OCCO1 | null | null | Cl | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 4 | Alcohol of step A (higher Rf isomer, 0.290 g, 1.11 mmol) was dissolved in THF (10 mL) under nitrogen. Hydrochloric acid (2.0 mL, 4.0 M aqueous solution, 8.0 mmol) was added and the mixture stirred for 4 hours at room temperature. The mixture was then diluted with NaHCO3/H2O and extracted twice with ethyl acetate. The e... | O=C1CC2CCC1CC2(O)c1cccnc1 | null | null | null |
1,061,391 | ord_dataset-ffbef48837674f39816de887b5dc8bae | null | 2011-01-01T00:06:00 | true | [F:1][C:2]1[C:3]([C@@H:8]([S:10][C:11]2[N:12]=[C:13]([NH:22][C@H:23]([CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:24][OH:25])[C:14]3[S:19][C:18]([O:20]C)=[N:17][C:15]=3[N:16]=2)[CH3:9])=[N:4][CH:5]=[CH:6][CH:7]=1>[Cl-].[Na+].O>[F:1][C:2]1[C:3]([C@@H:8]([S:10][C:11]2[N:12]=[C:13]([NH:22][C@@H:23]([CH2:24][OH:25])[CH2:26][CH:2... | COc1nc2nc(S[C@@H](C)c3ncccc3F)nc(N[C@@H](CO)CC(C)C)c2s1 | null | null | [Cl-] | [Na+] | 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 | 50 | null | The title compound was prepared from (2R)-2-[(5-{[(1S)-1-(3-fluoropyridin-2-yl)ethyl]thio}-2-methoxy[1,3]thiazolo[4,5-d]pyrimidin-7-yl)amino]-4-methylpentan-1-ol using General method D, except that the reaction mixture was heated to 50° C. for 1.5 h. After complete reaction the reaction mixture was diluted with brine a... | CC(C)C[C@H](CO)Nc1nc(S[C@@H](C)c2ncccc2F)nc2[nH]c(=O)sc12 | null | null | null |
1,065,500 | ord_dataset-ffbef48837674f39816de887b5dc8bae | null | 2011-01-01T00:06:00 | true | [Cl-].[Al+3].[Cl-].[Cl-].[S:5]1[CH:9]=[CH:8][C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6]1.[Br:15]Br>ClCCl>[Br:15][C:9]1[S:5][CH:6]=[C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:8]=1 | BrBr | CCOC(=O)c1ccsc1 | null | [Al+3] | [Cl-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 0 | null | 20 g (147 mmol) of aluminum chloride are added portionwise to a solution of 10 g (67 mmol) of ethyl thiophene-3-carboxylate in 160 ml of dichloromethane, cooled beforehand to 0° C. The reaction medium is warmed to room temperature and a solution of 4 ml (73 mmol) of bromine in 10 ml of dichloromethane is then added. Af... | CCOC(=O)c1csc(Br)c1 | null | 57.1 | null |
1,170,266 | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | null | 2012-01-01T00:05:00 | true | Br[C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[C:16]([O:24][CH2:25][C:26]([F:29])([F:28])[F:27])[CH:15]=3)[CH:11]=[C:10]([C:30]([F:33])([F:32])[F:31])[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[C:34]([NH:38][S:39]([C:42]1[CH:43]=[C:44](B(O)O)[CH:45]=[CH:46][CH:47]=1)(=[O:41])=[O... | CC(C)(C)NS(=O)(=O)c1cccc(B(O)O)c1 | FC(F)(F)COc1cc(-c2cc(C(F)(F)F)nc(-c3cccc(Br)c3)n2)ccc1C(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 | 3′-{4-[3-(2,2,2-Trifluoro-ethoxy)-4-trifluoromethyl-phenyl]-6-trifluoromethyl-pyrimidin-2-yl}-biphenyl-3-sulfonic acid tert-butylamide was prepared from 2-(3-bromo-phenyl)-4-[3-(2,2,2-trifluoro-ethoxy)-4-trifluoromethyl-phenyl]-6-trifluoromethyl-pyrimidine (example E.55) (0.38 g, 0.69 mmol) and commercially available 3... | CC(C)(C)NS(=O)(=O)c1cccc(-c2cccc(-c3nc(-c4ccc(C(F)(F)F)c(OCC(F)(F)F)c4)cc(C(F)(F)F)n3)c2)c1 | null | null | null |
1,134,221 | ord_dataset-aaeaab5f3720492494c1cbbdd0ed2820 | null | 2012-01-01T00:02:00 | true | [CH3:1][C:2]1[CH:6]=[C:5]([C:7]([F:10])([F:9])[F:8])[N:4]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)[N:3]=1.Cl.Cl[CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>>[CH3:1][C:2]1[CH:6]=[C:5]([C:7]([F:8])([F:10])[F:9])[N:4]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:20][CH2:21][N:22]3[CH2:27][CH2... | Cc1cc(C(F)(F)F)n(-c2ccc(O)cc2)n1 | ClCCN1CCCCC1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from 4-(3-Methyl-5-trifluoromethyl-pyrazol-1-yl)-phenol (0.1 g, 0.42 mmol) and 1-(2-chloroethyl)piperidine hydrochloride (0.16 g, 0.88 mmol) using the general procedure C with a yield of 55% (80 mg); 1H NMR (400 MHz, CDCl3) 7.33 (d, J=9.2 Hz, 2H), 6.98 (d, J=9.2 Hz, 2H), 6.43 (s, 1H), 4.... | Cc1cc(C(F)(F)F)n(-c2ccc(OCCN3CCCCC3)cc2)n1 | null | 55 | null |
698,151 | ord_dataset-4e9c2fa02a7544fd839206719263345f | null | 2006-01-01T00:02:00 | true | I[C:2]1[C:3]([CH3:17])=[N:4][N:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][OH:16])=[CH:10][CH:9]=2)[C:6]=1[CH3:7].[C:18]([C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=1)#[N:19]>>[OH:16][CH2:15][CH2:14][C:11]1[CH:12]=[CH:13][C:8]([N:5]2[C:6]([CH3:7])=[C:2]([C:24]3[CH:25]=[C:20]([CH:21]=[CH:22][CH:23]=3)[C:18]#[... | Cc1nn(-c2ccc(CCO)cc2)c(C)c1I | N#Cc1cccc(B(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 | The title compound was prepared according to the procedure described in step 1 of Example 12 from 2-[4-(4-iodo-3,5-dimethyl-1H-pyrazol-1-yl)phenyl]ethanol (step 2 of Example 11) and 3-cyanobenzeneboronic acid: MS (EI) m/z 317 [M]+, 1H-NMR (CDCl3) δ 7.63-7.34 (8H, m), 3.92 (2H, t, J=6.6 Hz), 2.94 (2H, t, J=6.6 Hz), 2.32... | Cc1nn(-c2ccc(CCO)cc2)c(C)c1-c1cccc(C#N)c1 | null | null | null |
827,484 | ord_dataset-47bd90bf5ec74fcd99ce250a56e18c8f | null | 2008-01-01T00:07:00 | true | [CH2:1]([NH:8][C:9]([C:11]1[C:19]2[C:18]3[CH:20]=[C:21]([NH2:24])[CH:22]=[CH:23][C:17]=3[O:16][C:15]=2[C:14]([O:25][CH3:26])=[CH:13][CH:12]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27](Cl)(=[O:29])[CH3:28].N1C=CC=CC=1>C1COCC1>[CH2:1]([NH:8][C:9]([C:11]1[C:19]2[C:18]3[CH:20]=[C:21]([NH:24][C:27](=[O:29])[CH... | CC(=O)Cl | COc1ccc(C(=O)NCc2ccccc2)c2c1oc1ccc(N)cc12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 2 | N-1-benzyl-4-methoxy-8-amino-dibenzo[b,d]furan-1-carboxamide (80 mg, 0.23 mmol) (step 2) was treated with acetyl chloride (1.1 eq.) in THF (10 ml) containing pyridine (1.0 eq) at 0° C. and allowed to warm to room temperature. The reaction was stirred at room temperature for 2 h. The reaction mixture was filterd and the... | COc1ccc(C(=O)NCc2ccccc2)c2c1oc1ccc(NC(C)=O)cc12 | null | null | null |
986,069 | ord_dataset-35b56288528641309a040cc2b6710b61 | null | 2010-01-01T00:08:00 | true | [CH3:1][C:2]([N:11]1[CH:15]=[C:14]([N+:16]([O-])=O)[N:13]=[CH:12]1)([CH3:10])[CH2:3][NH:4][CH2:5][C:6]([CH3:9])([CH3:8])[CH3:7].[F:19][C:20]1[CH:29]=[C:28]([F:30])[CH:27]=[C:26]2[C:21]=1[CH2:22][CH:23]([NH:31][C@@H:32]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:33](O)=[O:34])[CH2:24][CH2:25]2>>[F:30][C:28]1[CH:2... | O=C(O)[C@@H](NC1CCc2cc(F)cc(F)c2C1)c1ccccc1 | CC(C)(C)CNCC(C)(C)n1cnc([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 | 2-methyl-N-neopentyl-2-(4-nitro-1H-imidazol-1-yl)propan-1-amine (U.S. Ser. No. 11/078,898 filed Mar. 11, 2005) was reduced and coupled with (S)-2-(5,7-difluoro-1,2,3,4-tetrahydronaphthalen-3-ylamino)-2-phenylacetic acid to afford the title compound: MS 524 m/z (M+1). | CC(C)(C)CNCC(C)(C)n1cnc(NC(=O)[C@@H](NC2CCc3cc(F)cc(F)c3C2)c2ccccc2)c1 | null | null | null |
978,668 | ord_dataset-f886e51ba1484c76a94bce1482f1eab9 | null | 2010-01-01T00:07:00 | true | [Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](Cl)=[N:7][N:6]=[CH:5]2.[CH3:13][S:14]([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)(=[O:16])=[O:15]>ClCCl.CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([N:20]1[CH2:21][CH2:22][N:17]([S:14]([CH3:13])(=[O:16])=[O:15])[CH2:18][CH2:19]1)=[N:7][N:6]=[CH:5... | CS(=O)(=O)N1CCNCC1 | Clc1nncc2cc(Br)ccc12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | ClCCl | null | null | null | null | null | null | null | null | null | 120 | null | 6-Bromo-1-chlorophthalazine (18 mg, 74 umol) and 1-(methylsulfonyl)piperazine (91 mg, 554 μmol) were dissolved in dichloromethane/methanol when the reaction mixture was concentrated by evaporation under a nitrogen line. The concentrate was heated to 120° C. for 6 h to give the title compound. MS (ES+): 373 (M+H)+. | CS(=O)(=O)N1CCN(c2nncc3cc(Br)ccc23)CC1 | null | null | null |
745,728 | ord_dataset-4b705442211b4a3988e26d5f65098160 | null | 2006-01-01T00:12:00 | true | [NH2:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][C:7]2[NH:15][C:14]3[C:13](=[O:16])[N:12]([CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[F:24])[C:11](=[O:25])[N:10]([CH2:26][CH2:27][CH2:28][CH3:29])[C:9]=3[N:8]=2)=[CH:4][CH:3]=1.[I:32][C:33]1[CH:38]=[CH:37][C:36]([S:39](Cl)(=[O:41])=[O:40])=[CH:35][CH:34]=1>>[CH2:26]([... | CCCCn1c(=O)n(Cc2ccccc2F)c(=O)c2[nH]c(Cc3ccc(N)cc3)nc21 | O=S(=O)(Cl)c1ccc(I)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared from 8-(4-amino-benzyl)-3-butyl-1-(2-fluoro-benzyl)-3,7-dihydro-purine-2,6-dione and 4-iodo-benzenesulfonyl chloride. Purity (ELSD, based on MW=687.5)=100%. | CCCCn1c(=O)n(Cc2ccccc2F)c(=O)c2[nH]c(Cc3ccc(NS(=O)(=O)c4ccc(I)cc4)cc3)nc21 | null | null | null |
1,592,902 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([CH3:13])[N:10]([CH:14]3[C:18](=[O:19])/[C:17](=[CH:20]\[C:21]4[CH:26]=[CH:25][C:24]([F:27])=[CH:23][N:22]=4)/[CH2:16][C:15]3=[O:28])[N:9]=2)=[CH:4][CH:3]=1.[H][H]>CO.[Pd]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([CH3:13])[N:10]([CH:14]3[C:18](=[O:19])[CH:1... | [H][H] | Cc1cc(-c2ccc(Cl)cc2)nn1C1C(=O)C/C(=C/c2ccc(F)cn2)C1=O | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | To a solution of 2-[3-(4-chloro-phenyl)-5-methyl-pyrazol-1-yl]-4-[1-(5-fluoro-pyridin-2-yl)-meth-(Z)-ylidene]-cyclopentane-1,3-dione (17 mg, 0.04 mmol) in methanol (0.4 ml) was added 5% palladium on activated charcoal (2 mg) and the reaction stirred for 6 hours under 1.5 bar of hydrogen. The solution was then filtered ... | Cc1cc(-c2ccc(Cl)cc2)nn1C1C(=O)CC(Cc2ccc(F)cn2)C1=O | null | 98.7 | null |
903,645 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | [K].[CH:2]([CH:4]([CH2:7][C:8]#[N:9])[C:5]#[N:6])=O.[NH2:10][CH:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12]1.C(O)(=O)C.C(=O)([O-])[O-].[K+].[K+]>O>[NH2:9][C:8]1[N:10]([CH:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][CH2:12]2)[CH:2]=[C:4]([C:5]#[N:6])[CH:7]=1 | NC1CCc2ccccc21 | N#CCC(C#N)C=O | null | O=C([O-])[O-] | [K+] | [K] | 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 | 100 | 0.5 | Formyl succinonitrile potassium salt (36.5 g) and 1-aminoindane (36.6 g) were dissolved in water (100 ml), and acetic acid (100 ml) was added thereto. After agitating the mixture at 100° C. for 30 minutes, the reaction solution was poured into water (1200 ml). The reaction mixture was made basic by adding potassium car... | N#Cc1cc(N)n(C2CCc3ccccc32)c1 | null | 36.8 | null |
1,098,871 | ord_dataset-af85e6f81c2d49f08086afd6d9e6959c | null | 2011-01-01T00:10:00 | true | [Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[F:22][C:23]1[C:28]([F:29])=[CH:27][CH:26]=[CH:25][C:24]=1[C@H:30]1[CH2:36][NH:35][C:34](=[N:37][CH2:38][CH:39](O)[CH2:40][C:41]([F:44])([F:43])[F:42])[C@H:33]([NH:46][C:47](=[O:53])[O:48][C:49]([CH3:52])([CH3:51])[CH3:50])[CH2:32][CH2:31]1>C(#N)C>[F:2... | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](c2cccc(F)c2F)CNC1=NCC(O)CC(F)(F)F | null | null | O=[Cr](=O)([O-])O[Cr](=O)(=O)[O-] | c1cc[nH+]cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | null | 70 | Pyridinium dichromate (7.92 g, 21.0 mmol) was added to a solution of crude tert-butyl {(3R,6S)-6-(2,3-difluorophenyl)-2-[(4,4,4-trifluoro-2-hydroxybutyl)imino]azepan-3-yl}carbamate (3.27 g, 7.01 mmol) in acetonitrile (70 mL). After 70 h, the mixture was filtered and concentrated. Saturated aqueous sodium bicarbonate wa... | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](c2cccc(F)c2F)Cn2c(CC(F)(F)F)cnc21 | null | 75.3 | null |
91,856 | ord_dataset-dba7c8cf38834984ba5e6376158f46fe | null | 1982-01-01T00:03:00 | true | [N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[O:11][CH2:12][CH2:13][CH2:14][NH2:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:19][S:20][C:21](SC)=[CH:22][N+:23]([O-:25])=[O:24].[C:28]([OH:33])(=[O:32])[C:29]([OH:31])=[O:30]>O1CCCC1>[C:28]([OH:33])(=[O:32])[C:29]([OH:31])=[O:30].[N+:23]([CH:22]=[C:21]([S:2... | CSC(=C[N+](=O)[O-])SC | NCCCOc1cccc(CN2CCCCC2)c1 | null | O=C(O)C(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 3-[3-[(1-piperidinyl)methyl]phenoxy]propanamine (4.97 g.) and 1,1-bis-(methylthio)-2-nitroethene (6.61 g.) in tetrahydrofuran (100 ml.) was heated under reflux for 19 hours. A solution of oxalic acid (6.25%) in tetrahydrofuran (4 ml.) was added, the suspension filtered and to the filtrate was added a solut... | CSC(=C[N+](=O)[O-])NCCCOc1cccc(CN2CCCCC2)c1 | null | null | null |
83,178 | ord_dataset-7bed824f566d4af0b51d74d386b14bd6 | null | 1981-01-01T00:07:00 | true | [CH3:1][C:2]([CH3:19])([CH2:6][CH:7]=[CH:8][CH2:9][CH2:10][CH:11]=[CH:12][CH2:13][CH:14]([CH:16]([CH3:18])[CH3:17])[NH2:15])[CH:3]=[N:4]O.N.[H][H].O>CO.[Ni]>[CH:16]([CH:14]([NH2:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:2]([CH3:1])([CH3:19])[CH2:3][NH2:4])([CH3:18])[CH3:17] | CC(C)C(N)CC=CCCC=CCC(C)(C)C=NO | [H][H] | null | [Ni] | N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | O | null | null | null | null | null | null | null | null | null | 100 | 5 | 490 g (1.84 moles) of the 2,2-dimethyl-11-isopropyl-11-amino-undeca-4,8-dienal oxime obtained according to Example 5 are dissolved in 2.4 liters of methanol and this solution is filled, together with about 200 g of liquid ammonia, with the addition of 150 g of Raney nickel, into a 6.3 liter steel autoclave. Hydrogen is... | CC(C)C(N)CCCCCCCCC(C)(C)CN | null | 92.7 | null |
176,375 | ord_dataset-07db50a3ce6941919df30a9e2898988f | null | 1988-01-01T00:08:00 | true | Br[CH2:2][C:3]([C:5]1[O:9][N:8]=[C:7]([Br:10])[CH:6]=1)=O.[NH2:11][C:12]([NH2:14])=[S:13]>C(O)C>[NH2:14][C:12]1[S:13][CH:2]=[C:3]([C:5]2[O:9][N:8]=[C:7]([Br:10])[CH:6]=2)[N:11]=1 | O=C(CBr)c1cc(Br)no1 | NC(N)=S | 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 | null | null | A mixture of 32.4 g (120.4 mol) of 5-bromoacetyl-3-bromoisoxazole and 18.4 g (240 mmol) of thiourea in 400 ml of anhydrous ethanol was refluxed for 90 minutes. | Nc1nc(-c2cc(Br)no2)cs1 | null | null | null |
940,356 | ord_dataset-90b0aa1f83334a02919b2be3a1c04542 | null | 2010-01-01T00:02:00 | true | [C:1]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][N:8]1[C:16]2[CH:15]=[CH:14][N:13]=[C:12]([OH:17])[C:11]=2[CH:10]=[C:9]1[CH3:18].[N+](=[CH:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[N-]>ClCCCl.ClC(Cl)C>[CH2:31]([O:30][C:28](=[O:29])[CH2:27][O:17][C:12]1[C:11]2[CH:10]=[C:9](... | CCOC(=O)C=[N+]=[N-] | Cc1cc2c(O)nccc2n1Cc1ccccc1-c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(Cl)Cl | ClCCCl | null | null | null | null | null | null | null | null | null | null | null | To a solution of intermediate (5) (0.557 g, 1.77 mmole) in 1,2-dichloroethane (250 mL) rhodium(II) trifluoroacetate dimmer (0.058 g, 0.0885 mmole) was added, the reaction was heated to reflux. Then the solution of ethyl diazoacetate (90%, 0.2 mL, 1.77 mmole) in dichloroethane (35 mL) was added via a syringe pump to the... | CCOC(=O)COc1nccc2c1cc(C)n2Cc1ccccc1-c1ccccc1 | null | null | null |
438,859 | ord_dataset-3e8f24b5bc8e4d8bb9b6e7e89a956e12 | null | 1999-01-01T00:09:00 | true | [CH2:1]1[O:12][C:11]2[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][NH2:8])=[CH:4][C:3]=2[O:2]1.[Cl:13][C:14]1[N:15]=[C:16](Cl)[C:17]2[CH:22]=[C:21]([Cl:23])[S:20][C:18]=2[N:19]=1>>[Cl:13][C:14]1[N:15]=[C:16]([NH:8][CH2:7][CH2:6][C:5]2[CH:9]=[CH:10][C:11]3[O:12][CH2:1][O:2][C:3]=3[CH:4]=2)[C:17]2[CH:22]=[C:21]([Cl:23])[S:20][C:18]... | Clc1nc(Cl)c2cc(Cl)sc2n1 | NCCc1ccc2c(c1)OCO2 | null | null | null | null | null | null | null | 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 1, the reaction of 3,4-methylenedioxyphenethylamine with 2,4,6-trichloro-thieno-[2,3-d]-pyrimidine yields 2,6-dichloro-4-(3,4-methylenedioxyphenethylamino)-thieno-[2,3-d]-pyrimidine. | Clc1nc(NCCc2ccc3c(c2)OCO3)c2cc(Cl)sc2n1 | null | null | null |
769,445 | ord_dataset-8214eb8444a44dc2900ccb42dbeff15e | null | 2007-01-01T00:05:00 | true | [NH2:1]/[C:2](=[N:20]\[O:21][C:22]([C@H:24]([CH2:33][CH2:34][CH2:35][CH:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1)[CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=O)/[CH:3]1[CH2:6][N:5]([CH:7]([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)[CH2:4]1>C1(C)C... | CC(C)(C)OC(=O)C[C@@H](CCCC1CCCCC1)C(=O)O/N=C(\N)C1CN(C(c2ccccc2)c2ccccc2)C1 | null | 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 | 25 | null | A solution of tert-butyl(3R)-3-[({[(Z)-amino(1-benzhydryl-3-azetidinyl)methylidene]amino}oxy)carbonyl]-6-cyclohexylhexanoate (preparation 35) (2.85 g, 5.07 mmol) in toluene (90 ml) was heated at 140° C. under Dean and Stark conditions for 18 hours. The reaction mixture was allowed to cool to room temperature. The solve... | CC(C)(C)OC(=O)C[C@@H](CCCC1CCCCC1)c1nc(C2CN(C(c3ccccc3)c3ccccc3)C2)no1 | null | 72.5 | null |
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