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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
861,373 | ord_dataset-93908aaae836460ebd48d733eccad483 | null | 2009-01-01T00:01:00 | true | [NH2:1][C@H:2]1[CH2:6][CH2:5][N:4]([C@H:7]2[CH2:12][CH2:11][C@@H:10]([N:13]([CH:15]([CH3:17])[CH3:16])[CH3:14])[CH2:9][C@H:8]2[C:18]([O:20][CH3:21])=[O:19])[C:3]1=[O:22].[F:23][C:24]([F:35])([F:34])[C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=1)[C:28](O)=[O:29].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC>C(Cl)Cl>[CH... | O=C(O)c1cccc(C(F)(F)F)c1 | COC(=O)[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1CC[C@H](N)C1=O | null | CCN=C=NCCCN(C)C | On1nnc2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | ClCCl | null | null | null | null | null | null | null | null | null | null | null | A solution of (1R,2S,5R)-methyl 2-((S)-3-amino-2-oxopyrrolidin-1-yl)-5-(isopropyl(methyl)amino)-cyclohexanecarboxylate (50 mg, 0.16 mmol), 3-(trifluoromethyl)benzoic acid (38 mg, 0.20 mol), EDCI (38 mg, 0.20 mmol), HOBT (27 mg, 0.20 mmol), and Et3N (20 mg 0.20 mmol) in CH2Cl2 was stirred overnight at room temperature. ... | COC(=O)[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1CC[C@H](NC(=O)c2cccc(C(F)(F)F)c2)C1=O | null | 38.8 | null |
440,220 | ord_dataset-3e8f24b5bc8e4d8bb9b6e7e89a956e12 | null | 1999-01-01T00:09:00 | true | [C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@:11]3(O)[CH2:12][CH2:13][C@@H:14]2[CH3:24])[CH2:6]1)(=[O:3])[CH3:2].S(Cl)(Cl)=O>N1C=CC=CC=1.Cl>[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H... | CC(=O)O[C@H]1CC[C@@]2(C)[C@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H](C)CC[C@]32O)C1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=S(Cl)Cl | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | 2.5 | To a solution of 5.0 g of 3β-acetoxy-14β-hydroxy-17β-methyl-5β-androstane (VIII-a) in pyridine (100 mL), 3.5 g of thionyl chloride were added at 0° C. The solution was stirred at the same temperature for 2.5 hrs and then poured in 100 mL of 1N HCl and crushed ice: the mixture was extracted with ethyl ether: the organic... | CC(=O)O[C@H]1CC[C@@]2(C)[C@H](CC[C@H]3C4=CC[C@H](C)[C@@]4(C)CC[C@@H]32)C1 | null | 94.9 | null |
1,555,371 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | [C:1]([N:4]([C:8]1[C:13]([Cl:14])=[C:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]([C:25]3[C:26](=[O:38])[N:27]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[N:28]([CH3:31])[C:29]=3[CH3:30])=[O:24])=[CH:18][C:17]=2[F:39])[CH:11]=[CH:10][N:9]=1)C(=O)C)(=[O:3])[CH3:2].C([O-])([O-])=O.[Na+].[Na+]>CO.O>[C:1]([NH:4... | CC(=O)N(C(C)=O)c1nccc(Oc2ccc(NC(=O)c3c(C)n(C)n(-c4ccccc4)c3=O)cc2F)c1Cl | null | null | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CO | null | null | null | null | null | null | null | null | null | 25 | 0.25 | To a solution of N-(4-((2-(N-acetylacetamido)-3-chloropyridin-4-yl)oxy)-3-fluorophenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide (259 mg, 0.47 mmol) in CH3OH (20 mL) was added a solution of Na2CO3 (59.8 mg, 0.56 mmol) in H2O (1 mL). After stirring at rt for 15 minutes, the mixture was concentra... | CC(=O)Nc1nccc(Oc2ccc(NC(=O)c3c(C)n(C)n(-c4ccccc4)c3=O)cc2F)c1Cl | null | 66.8 | null |
822,179 | ord_dataset-ec58fad8331a42c5a67ad75aac6713b4 | null | 2008-01-01T00:05:00 | true | Cl.[CH3:2][CH:3]([CH3:23])[C@H:4]([NH:8][C:9]([NH:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=[C:14]([CH3:22])[CH:13]=1)=[O:10])[C:5]([OH:7])=O.[CH2:24]([CH:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[CH2:24]([CH... | c1ccc(CC2CCNCC2)cc1 | Cc1cc(NC(=O)N[C@H](C(=O)O)C(C)C)c2ccccc2n1 | null | Cl | On1nnc2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | ClCCCl | null | null | null | null | null | null | null | null | null | 25 | 15 | To a solution of (S)-3-methyl-2-[3-(2-methyl-quinolin-4-yl)-ureido]-butyric acid hydrochloride (337.8 mg, 1 mmol), 4-benzylpiperidine (175.3 mg, 1 mmol), HOBt (183 mg, 1.2 mmol) and TEA (0.35 mL, 2.5 mmol) in DMF (10 mL) is added EDC (230.0 mg, 1.2 mmol). The mixture is stirred for 15 h at room temperature and then que... | Cc1cc(NC(=O)N[C@H](C(=O)N2CCC(Cc3ccccc3)CC2)C(C)C)c2ccccc2n1 | null | null | null |
648,588 | ord_dataset-5d77a731aa10488794c824ad12021f57 | null | 2004-01-01T00:09:00 | true | [CH:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][C:14]3[C:19]([CH3:20])=[CH:18][C:17]([NH:21][C:22](=[O:28])[CH2:23][C:24]([O:26]C)=[O:25])=[CH:16][C:15]=3[CH3:29])[CH:11]=2)[NH:6][CH:5]=1)([CH3:3])[CH3:2].[OH-].[Na+]>C(O)C>[CH:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][C:14]3[C:19]([CH3:20])=[CH:18][C:17](... | COC(=O)CC(=O)Nc1cc(C)c(Oc2ccc3[nH]cc(C(C)C)c3c2)c(C)c1 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | 50 mg of methyl 3-({4-[(3-isopropyl-1H-indol-5-yl)oxy]-3,5-dimethyl-phenyl}-amino)-3-oxo-propanoate (Example 1) are stirred in 2 ml of ethanol with 30 mg of sodium hydroxide for 30 minutes. The solvent is removed in vacuo. The mixture is taken up in ether/water, the organic phase is dried and the solvent is removed in ... | Cc1cc(NC(=O)CC(=O)O)cc(C)c1Oc1ccc2[nH]cc(C(C)C)c2c1 | null | 47.7 | null |
1,047,301 | ord_dataset-dd320ded4b3f4764af39de99491533f7 | null | 2011-01-01T00:04:00 | true | CO[C:3]([C:5]1[N:6]=[C:7]([C:25]#[N:26])[C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[CH:10][C:9]=2[O:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)=[O:4].[NH2:27][CH2:28][C:29]([OH:31])=[O:30]>>[C:25]([C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][C:9]=2[O:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])... | NCC(=O)O | COC(=O)c1nc(C#N)c2c(Oc3ccc(OC)cc3)cccc2c1O | null | null | null | null | null | null | null | 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-cyano-4-hydroxy-8-(4-methoxy-phenoxy)-isoquinoline-3-carboxylic acid methyl ester and glycine in analogy to example 1b; MS-(−)-ion: M−1=392.4. | COc1ccc(Oc2cccc3c(O)c(C(=O)NCC(=O)O)nc(C#N)c23)cc1 | null | null | null |
293,964 | ord_dataset-bb4579c57ddc48c6a01fad97dacb6293 | null | 1994-01-01T00:08:00 | true | Cl.[Cl:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([OH:10])=[C:5]([N+]([O-])=O)[CH:4]=1>O>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([OH:10])=[CH:7][C:8]=1[CH3:9] | Cc1cc(O)c([N+](=O)[O-])cc1Cl | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | null | null | To 160 ml of methanol, there were added 37.9 g of the 4'-chloro-5'-methyl-2'-nitrophenyl methanesulfonate as obtained in the above (ii) and 80 ml of a 7N aqueous solution of sodium hydroxide, followed by heating under reflux for 20 minutes. After cooling, the reaction mixture was poured into 500 ml of water and neutral... | Cc1cc(O)ccc1Cl | null | null | null |
402,215 | ord_dataset-7fed188163cf4ccca934ec71504c7f8a | null | 1998-01-01T00:05:00 | true | [ClH:1].Cl.[N:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][NH:13][CH2:12][CH2:11][N:10]2[CH2:15][CH2:16][CH2:17][C:18]([O:20]CC)=[O:19])=[CH:5][CH:4]=1>Cl>[ClH:1].[ClH:1].[N:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH2:14][NH:13][CH2:12][CH2:11][N:10]2[CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[CH:7][CH:8]=1 | CCOC(=O)CCCN1CCNCC1c1ccncc1 | null | 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 | 100 | null | A mixture of the product of step (i) (5 g) and conc. HCl (50 ml) was heated at 100° C. for 45 min. The resultant solution was evaporated to dryness and the residue dissolved again in conc. HCl and heated to 100° C. for a further 45 min. The reaction mixture was evaporated to dryness, and the residue was twice triturate... | O=C(O)CCCN1CCNCC1c1ccncc1 | null | 150 | null |
796,814 | ord_dataset-a2d74266062e4398bc26c4f876903ab8 | null | 2007-01-01T00:11:00 | true | [C:1]([NH:8][C@@H:9]([C:11]([OH:13])=[O:12])[CH3:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:14](O)[CH3:15].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.CN(C1C=CC=CN=1)C>[CH2:14]([O:12][C:11](=[O:13])[C@@H:9]([CH3:10])[NH:8][C:1]([O:3][C:4]([CH3:7])([CH3:5])[CH3:6])=[O:2])[CH3:15] | C[C@@H](NC(=O)OC(C)(C)C)C(=O)O | CCO | null | C(=NC1CCCCC1)=NC1CCCCC1 | CN(C)c1ccccn1 | 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 | 8 | Boc-D-alanine (5.0 g, 26.4 mmol), dimethylaminopyridine (161 mg, 1.3 mMol), and ethanol (1.34 g, 29.1 mMol) were dissolved in methylene chloride (300 ml), and the solution was cooled to 0° C. To this solution was added 1,3-dicyclohexylcarbodiimide (6.0 g, 29.1 mMol). The mixture was allowed to slowly come to room tempe... | CCOC(=O)[C@@H](C)NC(=O)OC(C)(C)C | null | 85.4 | null |
481,057 | ord_dataset-21c1b1c06c7e4e09a38b5b1c71a32e52 | null | 2000-01-01T00:10:00 | true | [Cl:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][N:16]=3)=[CH:10][C:9]=2[CH3:22])=[O:7])=[CH:4][CH:3]=1.[CH3:25][N:26]=[C:27]=[S:28]>C1COCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH2:14][C:15]3[CH:20]=[CH:... | Cc1cc(Cc2ccc(N)cn2)n(C)c1C(=O)c1ccc(Cl)cc1 | CN=C=S | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | C1CCOC1 | null | null | null | null | null | null | null | null | null | 60 | 8 | N-{2-[5-(4-Chlorobenzoyl)-1,4-dimethyl-1H-pyrrol-2-ylmethyl]pyridin-5-yl}amine (0.3 g, 0.88 mmol) and methylisothiocyanate (0.3 ml, 4.4 mmol) were dissolved in THF and the reaction mixture was stirred at 60° C. overnight. The mixture was diluted with ethyl acetate and washed with 1N HCl, 10% sodium bicarbonate, water, ... | CNC(=S)Nc1ccc(Cc2cc(C)c(C(=O)c3ccc(Cl)cc3)n2C)nc1 | null | 72.9 | null |
886,746 | ord_dataset-d728a2f811c0424cbcdb5a84d02b93ae | null | 2009-01-01T00:06:00 | true | [CH2:1]([N:8]1[CH:14]2[CH2:15][CH2:16][CH:9]1[CH:10]1[N:17](C)[CH:13]2[CH2:12][CH2:11]1)C1C=CC=CC=1.[H][H]>CCO.[Pd]>[CH3:1][N:8]1[CH:14]2[CH2:15][CH2:16][CH:9]1[CH:10]1[NH:17][CH:13]2[CH2:12][CH2:11]1 | CN1C2CCC1C1CCC2N1Cc1ccccc1 | [H][H] | 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 | To a cold (0° C.) solution of 9-benzyl-9,10-diazatricyclo[4.2.1.12,5]decane (J. Med. Chem. 2000, 43, 2115-2123) and TEA in an DMF (1-2 ml) was added MeI. The mixture was allowed to warm to rt and stirred for 2-3 h. The rxn mixture was evaporated to dryness and partitioned between ether and satd. NaHCO3 and ether layer ... | CN1C2CCC1C1CCC2N1 | null | null | null |
1,226,497 | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | null | 2012-01-01T00:11:00 | true | [Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([NH2:17])([CH3:16])[CH3:15])=[CH:10][CH:9]=2)[CH:5]=[N:6][CH:7]=1.Cl[CH2:19][CH2:20][O:21][CH2:22][CH2:23]Cl>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([N:17]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)([CH3:15])[CH3:16])=[CH:10][CH:9]=2... | CC(C)(N)c1ccc(-c2cncc(Br)c2)cc1 | ClCCOCCCl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 1-[4-(5-bromo-pyridin-3-yl)-phenyl]-1-methyl-ethylamine (Intermediate 229) (1 eq, 1.72 mmol, 500 mg), TEA (3.5 eq, 6.01 mmol, 608 mg), and 2-chloroethyl ether (Sigma-Aldrich, St. Louis, USA) (4 eq, 6.87 mmol, 0.8 ml) in DMF (10 ml) is heated using microwave radiation at 150° C. for 1 h. The mixture is conc... | CC(C)(c1ccc(-c2cncc(Br)c2)cc1)N1CCOCC1 | null | null | null |
1,379,048 | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | null | 2013-01-01T00:12:00 | true | [CH3:1][C:2]1([NH:18][C:19](=[O:21])[CH3:20])[CH2:8][CH2:7][CH2:6][N:5]([C:9]2[N:13]([CH3:14])[N:12]=[CH:11][C:10]=2[N+:15]([O-])=O)[CH2:4][CH2:3]1.[Cl-].[NH4+]>CCO.O.[Fe]>[NH2:15][C:10]1[CH:11]=[N:12][N:13]([CH3:14])[C:9]=1[N:5]1[CH2:6][CH2:7][CH2:8][C:2]([NH:18][C:19](=[O:21])[CH3:20])([CH3:1])[CH2:3][CH2:4]1 | CC(=O)NC1(C)CCCN(c2c([N+](=O)[O-])cnn2C)CC1 | null | null | [Fe] | [Cl-] | [NH4+] | 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 | 100 | null | To a stirred solution of N-(4-methyl-1-(1-methyl-4-nitro-1H-pyrazol-5-yl)azepan-4-yl)acetamide (330 mg, 1.11 mmol) in a mixture of EtOH (25 mL) and water (2.5 mL) was added ammonium chloride (300 mg, 5.55 mmol) and iron powder (250 mg, 4.44 mmol). The reaction mixture was heated at 100° C. for 2 hr before being cooled,... | CC(=O)NC1(C)CCCN(c2c(N)cnn2C)CC1 | null | null | null |
1,748,941 | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | null | 2016-01-01T00:07:00 | true | [CH2:1]([O:8][C@@H:9]1[C@@H:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@:14]2([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([CH2:32][C:33]4[CH:38]=[CH:37][C:36]([O:39][CH2:40][CH3:41])=[CH:35][CH:34]=4)[CH:26]=3)[O:24][C@@:11]([CH2:42][OH:43])([CH2:12][O:13]2)[C:10]1=[O:44])[C:2]1[CH:7]=[CH:6][CH... | CCOc1ccc(Cc2cc([C@]34OC[C@](CO)(O3)C(=O)[C@H](OCc3ccccc3)[C@H]4OCc3ccccc3)ccc2Cl)cc1 | CC(=O)OC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 25 | 2 | To a solution of (1S,3R,4R,5S)-3,4-dibenzyloxy-5-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octan-2-one 28g (13.4 g, 21.8 mmol) in dichloromethane (40 mL) were added acetic anhydride (3.0 mL, 32.7 mmol) and triethylamine (6.0 mL, 43.6 mmol) at room temperature. The mixture was ... | CCOc1ccc(Cc2cc([C@]34OC[C@](COC(C)=O)(O3)C(=O)[C@H](OCc3ccccc3)[C@H]4OCc3ccccc3)ccc2Cl)cc1 | null | 84.5 | null |
1,364,050 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | [C:1]([O:5][C:6](=[O:20])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([N:16]=[C:17]=S)[C:10]=1[Cl:19])([CH3:4])([CH3:3])[CH3:2].[NH2:21][C:22]1[C:23]([NH2:46])=[N:24][C:25]([O:41][CH2:42][CH:43]([F:45])[F:44])=[C:26]([CH:40]=1)[C:27]([NH:29][C@H:30]1[CH2:35][CH2:34][C@H:33]([C:36]([F:39])([F:38])[F:37])[CH2... | Nc1cc(C(=O)N[C@H]2CC[C@H](C(F)(F)F)CC2)c(OCC(F)F)nc1N | CC(C)(C)OC(=O)NCc1ccc(Cl)c(N=C=S)c1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | ClCCCl | null | null | null | null | null | null | null | null | null | null | null | The title compound is prepared from (2,4-dichloro-3-isothiocyanato-benzyl)-carbamic acid tert-butyl ester (3.15 g, 9.45 mmol), 5,6-diamino-2-(2,2-difluoro-ethoxy)-N-(trans-4-trifluoromethyl-cyclohexyl)-nicotinamide (3.60 g, 9.42 mmol), EDC (2.0 g, 10.4 mmol) in MeCN (40 ml) in analogy to example 5c. | CC(C)(C)OC(=O)NCc1ccc(Cl)c(Nc2nc3cc(C(=O)N[C@H]4CC[C@H](C(F)(F)F)CC4)c(OCC(F)F)nc3[nH]2)c1Cl | null | null | null |
1,452,676 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([C:11]([OH:13])=O)[CH:9]=[CH:10][C:2]1=2.C1C=CC2N(O)N=[N:20]C=2C=1.N.CCN=C=NCCCN(C)C.Cl.O>CN(C=O)C>[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([C:11]([NH2:20])=[O:13])[CH:9]=[CH:10][C:2]1=2 | On1nnc2ccccc21 | O=C(O)c1ccc2c(c1)OCCO2 | null | CCN=C=NCCCN(C)C | Cl | N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | O | null | null | null | null | null | null | null | null | null | 25 | 72 | To a solution of 2,3-dihydrobenzo[b][1,4]dioxine-6-carboxylic acid (3.54 g) in DMF (80 mL) were added HOBt-NH3 (4.48 g) and EDCI HCl (5.65 g) at room temperature. The reaction mixture was stirred at room temperature for 3 days, water was added, and the mixture was extracted with ethyl acetate. The extract was washed wi... | NC(=O)c1ccc2c(c1)OCCO2 | null | 31.2 | null |
234,831 | ord_dataset-45d20d09e4d64f45bdd419044025b4d3 | null | 1991-01-01T00:09:00 | true | [C:1]([CH2:3][CH2:4][P:5]([CH2:11][CH3:12])(=[O:10])[O:6][CH:7]([CH3:9])[CH3:8])#[N:2].N.[H][H]>C(O)(C)C.[Ni]>[NH2:2][CH2:1][CH2:3][CH2:4][P:5]([CH2:11][CH3:12])(=[O:10])[O:6][CH:7]([CH3:9])[CH3:8] | [H][H] | CCP(=O)(CCC#N)OC(C)C | null | [Ni] | N | 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 | null | null | To 34.1 g of isopropyl 2-cyanoethyl(ethyl)phosphinate in 500 ml of isopropanol are added 60 ml of liquid ammonia and 6.8 g of Raney-Nickel. The mixture is heated to 80° and treated with hydrogen at 100 bar. After 11/2 hours hydrogen-uptake stops. The reaction mixture is filtered and the filtrate distilled to give isopr... | CCP(=O)(CCCN)OC(C)C | null | null | null |
156,999 | ord_dataset-36f7bef430f14c2e8db5e3f7c3640d9b | null | 1987-01-01T00:04:00 | true | Cl.N[CH2:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([S:11]([CH3:14])(=[O:13])=[O:12])[C:5]=1[OH:15].C1N2CN3CN(C2)CN1C3.FC(F)(F)C(O)=[O:29]>>[CH:3]([C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([S:11]([CH3:14])(=[O:13])=[O:12])[C:5]=1[OH:15])=[O:29] | CS(=O)(=O)c1cc(Cl)cc(CN)c1O | O=C(O)C(F)(F)F | null | C1N2CN3CN1CN(C2)C3 | 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 | 2.4 g (0.009 mol) of 2-aminomethyl-4-chloro-6methylsulfonylphenol hydrochloride are reacted with 1.6 g of urotropine in 18 ml of trifluoroacetic acid to give 2-formyl-4-chloro-6-methylsulfonylphenol in analogy to Example 1. | CS(=O)(=O)c1cc(Cl)cc(C=O)c1O | null | null | null |
102,571 | ord_dataset-bdb961f26fac426eaa2de8f54a284acf | null | 1983-01-01T00:02:00 | true | [OH:1][CH2:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].[Cl:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH:17]=O>>[Cl:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH:17]=[C:2]([OH:1])[C@@H:3]([OH:4])[C@@H:5]([OH:6])[C@H:7]([OH:8])[C@@H:9]([OH:10])[C:11](=[CH... | OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)CO | O=Cc1ccc(Cl)c(Cl)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Bis(3,4-dichlorobenzylidene)sorbitol was prepared from aqueous sorbitol and 3,4-dichlorobenzaldehyde according to the method of Example 1. The melting point of the product was 270° C. | OC(=Cc1ccc(Cl)c(Cl)c1)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=Cc1ccc(Cl)c(Cl)c1 | null | null | null |
995,135 | ord_dataset-b6d8835b0c934476a36e6149e7597487 | null | 2010-01-01T00:09:00 | true | [Br:1][C:2]1[CH:3]=[C:4]([CH:10]=O)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[C:12]1([CH3:26])[CH:17]=[CH:16][C:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=2)=[CH:14][CH:13]=1.[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][NH:25][C:22]2[CH:21]=[CH:20][C:19]([O:18][C:15]3[CH:16]=[CH:17][C:12]([CH3:26])=[C... | Cc1ccc(Oc2ccc(N)cc2)cc1 | COc1ncc(Br)cc1C=O | null | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 0 | 8 | A solution of 5-bromo-2-methoxy-pyridine-3-carbaldehyde (0.87 g, 4.03 mmol) in dry MeOH (15 mL) was treated with 4-p-tolyloxy-phenylamine (0.88 g, 4.43 mmol) and reflux for 2.5 h. The solution was cooled to 0° C. and treated slowly with NaBH4 (0.38 g, 10.1 mmol). The reaction stirred at room temperature overnight. Addi... | COc1ncc(Br)cc1CNc1ccc(Oc2ccc(C)cc2)cc1 | null | null | null |
982,771 | ord_dataset-35b56288528641309a040cc2b6710b61 | null | 2010-01-01T00:08:00 | true | [F:1][C:2]([F:18])([F:17])[CH2:3][CH2:4][S:5]([N:8]([C@@H:10]([CH2:14][CH:15]=[CH2:16])[C:11]([OH:13])=O)[CH3:9])(=[O:7])=[O:6].[CH2:19]([O:22][C@H:23]1[C:31]2[C:26](=[CH:27][C:28]([O:32][CH3:33])=[CH:29][CH:30]=2)[C@@H:25]([NH:34][CH2:35][C@@H:36]([OH:48])[C@@H:37]([NH2:47])[CH2:38][C:39]2[CH:44]=[C:43]([Cl:45])[CH:42... | C=CCO[C@@H]1C[C@H](NC[C@@H](O)[C@@H](N)Cc2cc(Cl)cc(Cl)c2)c2cc(OC)ccc21 | C=CC[C@@H](C(=O)O)N(C)S(=O)(=O)CCC(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 | Step DM (1): (S)-2-(3,3,3-Trifluoro-N-methyl-propylsulfonamido)pent-4-enoic acid (33 mg, 0.11 mmol, from Preparation J) was coupled with (2R,3S)-1-((1S,3R)-3-(allyloxy)-6-methoxy-2,3-dihydro-1H-inden-1-ylamino)-3-amino-4-(3,5-dichloro-phenyl)butan-2-ol (50 mg, from Preparation BG) by a procedure analogous to Step DL (1... | C=CCO[C@@H]1C[C@H](NC[C@@H](O)[C@H](Cc2cc(Cl)cc(Cl)c2)NC(=O)[C@H](CC=C)N(C)S(=O)(=O)CCC(F)(F)F)c2cc(OC)ccc21 | null | 24 | null |
162,037 | ord_dataset-c34472859da14a81bfe0f74e60f15c43 | null | 1987-01-01T00:08:00 | true | Cl[C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH3:8])[C:3]=1[C:9](=[O:18])[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=1[Cl:17].[SH2:19].[Na]>C(O)C>[CH3:7][N:6]1[C:2]([SH:19])=[C:3]([C:9](=[O:18])[C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])[C:4]([CH3:8])=[N:5]1 | S | Cc1nn(C)c(Cl)c1C(=O)c1ccc(Cl)cc1Cl | null | [Na] | 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 0.3 g. of 5-chloro-4-(2,4-dichlorobenzoyl)-1,3-dimethylpyrazole, 2.1 g. of sodium hydrogen sulfide 2 hydrate and 6 ml. of ethanol is heated under reflux on a water bath for 3 hours. After completion of the reaction, the ethanol is distilled off under reduced pressure from the reaction mixture and 15 ml. of... | Cc1nn(C)c(S)c1C(=O)c1ccc(Cl)cc1Cl | null | 33.3 | null |
935,614 | ord_dataset-90b0aa1f83334a02919b2be3a1c04542 | null | 2010-01-01T00:02:00 | true | [N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][CH:2]=1.[OH-].[K+].Br[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20]Br)[CH:15]=1>CC(C)=O>[N:1]1([CH2:13][C:14]2[CH:15]=[C:16]([CH:17]=[CH:18][CH:19]=2)[CH2:20][N:1]2[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=[CH:2]2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]... | BrCc1cccc(CBr)c1 | c1ccc2[nH]cnc2c1 | null | [K+] | [OH-] | 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 | null | null | To a 1 L round bottom flask equipped with a stirbar was added 26.8 g benzimidazole (227 mmol) and 12.7 g (227 mmol) finely pulverized potassium hydroxide. These were stirred in 500 mL acetone for 20 minutes at reflux. 20.0 g (78.5 mmol) α,α′-dibromo-m-xylene was then added, and the solution was stirred at reflux for 6 ... | c1cc(Cn2cnc3ccccc32)cc(Cn2cnc3ccccc32)c1 | null | 18.8 | null |
235,619 | ord_dataset-1acb071a357f438ea5993287375971cf | null | 1991-01-01T00:10:00 | true | [C:1]1([CH2:7][CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]2=[CH:14][C:15]([OH:17])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:18][CH2:19][CH2:20][SH:21]>CN(C)C=O.C(OCC)(=O)C>[C:1]1([CH2:7][CH:8]2[C:9]3([CH2:14][C:15](=[O:17])[NH:18][CH2:19][CH2:20][S:21]3)[CH2:10][CH2:11][CH2:12][CH2:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6... | O=C(O)C=C1CCCCC1Cc1ccccc1 | NCCS | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 0 | null | A mixture of 2-phenylmethyl-1-carboxymethylenecyclohexane (10 g) and 2-aminoethanethiol (10 g) in N,N-dimethylformamide (10 ml) was refluxed for 20 hours under nitrogen atmosphere. The mixture was cooled to 0° C. and diluted with ethyl acetate (100 ml), and the mixture was washed with 1N hydrochloric acid (100 ml), wat... | O=C1CC2(CCCCC2Cc2ccccc2)SCCN1 | null | 52.5 | null |
1,190,627 | ord_dataset-4e81c470cc3b429faf5e1caa50f70a98 | null | 2012-01-01T00:08:00 | true | [N:1]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[NH:4][CH2:3][CH2:2]2.Cl[C:11]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=[CH:13][N:12]=1.O1CCOCC1>O>[N+:17]([C:16]1[CH:15]=[CH:14][C:13]([N:4]2[CH:5]3[CH2:8][CH2:9][N:1]([CH2:7][CH2:6]3)[CH2:2][CH2:3]2)=[N:12][CH:11]=1)([O-:19])=[O:18] | O=[N+]([O-])c1cccnc1Cl | C1CN2CCC(CC2)N1 | null | null | null | 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 | 1,4-diazabicyclo[3.2.2]nonane (6.3 g, 50 mmol) was added to a mixture of 2-chloro-nitropyridine (11.9, 75 mmol), and dioxane (250 ml) at 0° C. The reaction mixture was allowed to reach room-temperature. Water (100 ml) was added. The mixture was extracted with dichloromethane (3×50 ml). Chromatography on silica gel with... | O=[N+]([O-])c1ccc(N2CCN3CCC2CC3)nc1 | null | null | null |
576,685 | ord_dataset-f4512fe8cd804ac79da66cbc0c2b9d42 | null | 2002-01-01T00:12:00 | true | [CH3:1][S:2][CH2:3][CH2:4][CH2:5][NH:6][S:7]([C:10]1[C:15]([Cl:16])=[CH:14][CH:13]=[C:12]([N+:17]([O-:19])=[O:18])[C:11]=1Cl)(=[O:9])=[O:8].[H-].[Na+].[OH2:23]>>[CH3:1][S:2][CH2:3][CH2:4][CH2:5][NH:6][S:7]([C:10]1[C:15]([Cl:16])=[CH:14][CH:13]=[C:12]([N+:17]([O-:19])=[O:18])[C:11]=1[OH:23])(=[O:9])=[O:8] | O | CSCCCNS(=O)(=O)c1c(Cl)ccc([N+](=O)[O-])c1Cl | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Following the general hydrolysis procedure outlined in example 15, N-(3-methylthiopropyl)-2,6-dichloro-3-nitrobenzenesulfonamide (1.0 g, 2.78 mmol), 60% NaH (330 mg, 8.13 mmol) and water (59 μL, 3.25 mmol) were reacted to form the desired product (650 mg, 69%). EI-MS (m/z) 339.86, 341.84 (M−). | CSCCCNS(=O)(=O)c1c(Cl)ccc([N+](=O)[O-])c1O | null | 68.6 | null |
859,755 | ord_dataset-93908aaae836460ebd48d733eccad483 | null | 2009-01-01T00:01:00 | true | [CH2:1]([O:8][C:9]1[C:10]([C:18]([O:20][CH3:21])=[O:19])=[N:11][NH:12][C:13]=1[C:14]([O:16][CH3:17])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:24]#[N:25].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH2:1]([O:8][C:9]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[N:12]... | N#CC(Br)c1ccccc1 | COC(=O)c1n[nH]c(C(=O)OC)c1OCc1ccccc1 | null | O=C([O-])[O-] | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 25 | 72 | A solution of dimethyl 4-benzyloxy-1H-pyrazole-3,5-dicarboxylate (1.0 g, 3.45 mmol) and bromo(phenyl)acetonitrile (810 mg, 4.13 mmol) in anhydrous DMF was treated with Cs2CO3 (1.46 g, 4.48 mmol) and stirred at room temperature for 3 days. The solvent was removed in vacuo and the residue was partitioned between EtOAc an... | COC(=O)c1nn(C(C#N)c2ccccc2)c(C(=O)OC)c1OCc1ccccc1 | null | null | null |
163,641 | ord_dataset-f5dc3e448c204058b116bf1970695bef | null | 1987-01-01T00:09:00 | true | [O:1]1CCN=[CH:2]1.[F:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([OH:12])=[O:11].[Li]C(CC)C.CN(C=O)C>C1COCC1>[F:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:9]2[C:8]=1[CH:2]([OH:1])[O:11][C:10]2=[O:12] | C1=NCCO1 | O=C(O)c1cccc(F)c1 | null | [Li]C(C)CC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CN(C)C=O | null | null | null | null | null | null | null | null | null | -78 | 0.5 | To a -78° C. solution of the oxazoline derivative (7.8 g, 40.4 mmol), prepared from 3-fluorobenzoic acid in tne usual manner, in THF (50 mL) was added over 15 min sec-BuLi (29 mL of 1.4 M solution). After 30 min, DMF (6.3 mL) was added, and the reaction mixture was stirred at -78° C. for 2 hr. Tne reaction was then que... | O=C1OC(O)c2c(F)cccc21 | null | null | null |
1,434,142 | ord_dataset-5e6956e6e8c24a168866a253f4a66c6c | null | 2014-01-01T00:05:00 | true | Cl[C:2]1[CH:16]=[CH:15][C:5]2[C:6](=[O:14])[NH:7][C:8]3[C:13]([C:4]=2[CH:3]=1)=[CH:12][CH:11]=[CH:10][N:9]=3.[O:17]1[C:21]2[CH:22]=[CH:23][C:24]([CH2:26][NH2:27])=[CH:25][C:20]=2[O:19][CH2:18]1>>[O:17]1[C:21]2[CH:22]=[CH:23][C:24]([CH2:26][NH:27][C:2]3[CH:16]=[CH:15][C:5]4[C:6](=[O:14])[NH:7][C:8]5[C:13]([C:4]=4[CH:3]=... | O=c1[nH]c2ncccc2c2cc(Cl)ccc12 | NCc1ccc2c(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 | The title compound was synthesized according to the procedure described for the preparation of Example 456 using 6 (266 mg, 1.15 mmol) and benzo[d]-[1,3]dioxol-5-ylmethanamine (697 mg, 4.61 mmol) to provide 476 (67 mg, 17% yield) as a white powder. LC-MS (M+H=346, obsd.=346). 1H NMR (400 MHz, DMSO-D6) δ 11.49 (s, 1H), ... | O=c1[nH]c2ncccc2c2cc(NCc3ccc4c(c3)OCO4)ccc12 | null | 16.9 | null |
11,488 | ord_dataset-7c810806c4564bada4a9550135bbb06f | null | 1976-01-01T00:08:00 | true | [C:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=O)([OH:3])=[O:2].Br[CH:13](C(OCC)=O)[C:14]([O:16]CC)=[O:15].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[C:1]1([C:4]2[C:5](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[C:13]([C:14]([OH:16])=[O:15])[O:3]1)=[O:2] | O=Cc1ccccc1C(=O)O | CCOC(=O)C(Br)C(=O)OCC | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCC(C)=O | null | null | null | null | null | null | null | null | null | null | null | 5 | A mixture of 2-carboxybenzaldehyde (20.0g), diethyl bromomalonate (20.0g) and anhydrous potassium carbonate (20.0g) in ethyl methylketone (200ml.) was heated under reflux, with stirring, for 5 hours. The cooled mixture was evaporated to dryness and water (300ml.) added to the residue. After extraction with a mixture of... | O=C(O)c1cc2ccccc2c(=O)o1 | null | null | null |
1,362,279 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | [NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[C:11]([C:13](=[O:18])[NH:14][CH:15]3[CH2:17][CH2:16]3)[CH:10]=[CH:9][C:8]=2[CH3:19])[N:5]=[CH:4][C:3]=1[C:20]([OH:22])=O.[CH3:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH:25]1[NH2:30].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O>[CH3:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH:... | CC1CCCCC1N | Cc1ccc(C(=O)NC2CC2)cc1-n1ncc(C(=O)O)c1N | null | CCN=C=NCCCN(C)C | On1nnc2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | A solution of 5-amino-1-(5-cyclopropylcarbamoyl-2-methylphenyl)-1H-pyrazole-4-carboxylic acid (21 mg), 2-methylcyclohexylamine (10 mg), EDCI (28 mg) and HOBt (12 mg) in DMF (0.75 ml) was reacted at room temperature for 24 h. Water (4 ml) was added and the solution was extracted with ethyl acetate (3 mL×2). The organic ... | Cc1ccc(C(=O)NC2CC2)cc1-n1ncc(C(=O)NC2CCCCC2C)c1N | null | 68.7 | null |
1,322,173 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | Cl[C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)=[CH:6][CH:7]=1.[N:14]1([CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>>[N:11]1[CH:12]=[CH:13][C:8]([C:5]2[N:4]=[N:3][C:2]([N:23]3[CH2:24][CH2:25][CH:20]([N:14]4[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]4)[CH2... | Clc1ccc(-c2ccncc2)nn1 | C1CCN(C2CCNCC2)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 | The title compound was prepared by a similar procedure to that described in Example 1, starting from 3-chloro-6-pyridin-4-yl-pyridazine and 4-piperidinopiperidine. 1H NMR (400 MHz, DMSO-d6) δ 8.67 (dd, 2H), 8.04 (m, 3H), 7.40 (d, 1H), 4.53 (d, 2H), 2.95 (t, 2H), 2.56 (m, 1H), 2.45 (m, 4H), 1.82 (d, 2H), 1.48 (m, 6H) 1.... | c1cc(-c2ccc(N3CCC(N4CCCCC4)CC3)nn2)ccn1 | null | null | null |
1,060,224 | ord_dataset-ffbef48837674f39816de887b5dc8bae | null | 2011-01-01T00:06:00 | true | [Cl:1][C:2]1[C:20]([CH3:21])=[C:19]([Cl:22])[CH:18]=[CH:17][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([CH2:11][C@H:12]([OH:16])[CH2:13][NH:14][CH3:15])[CH2:7][CH2:6]1.[O:23]=[C:24]1[NH:28][C:27]([C:29]([F:32])([F:31])[F:30])=[C:26]([C:33]([OH:35])=O)[S:25]1>>[Cl:1][C:2]1[C:20]([CH3:21])=[C:19]([Cl:22])[CH:18]=[CH:17][C:3]... | CNC[C@@H](O)CN1CCC(Oc2ccc(Cl)c(C)c2Cl)CC1 | O=C(O)c1sc(=O)[nH]c1C(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 | Prepared as Example 1 using (2R)-1-[4-(2,4-dichloro-3-methylphenoxy)piperidin-1-yl]-3-(methylamino)propan-2-ol (0.156 g) and 2-oxo-4-(trifluoromethyl)-2,3-dihydro-1,3-thiazole-5-carboxylic acid (0.096 g) to yield the title compound as a colourless solid (0.091 g). | Cc1c(Cl)ccc(OC2CCN(C[C@H](O)CN(C)C(=O)c3sc(=O)[nH]c3C(F)(F)F)CC2)c1Cl | null | 37.3 | null |
18,340 | ord_dataset-8ca24382d55b4303bc34393399f4110e | null | 1977-01-01T00:01:00 | true | Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][Cl:14])=[CH:7][CH:6]=1)=[O:4].[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].CC(C)=O>O>[Cl:14][CH2:13][CH2:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([C:3](=[O:4])[CH2:2][O:23][C:20]2[CH:21]=[CH:22][C:17]([O:16][CH3:... | O=C(CBr)c1ccc(OCCCl)cc1 | COc1ccc(O)cc1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | O | null | null | null | null | null | null | null | null | null | null | 16 | A mixture of 27.7 g. (0.1 mol.) of α-bromo-p-(2-chloroethoxy)acetophenone, 12.4 g. (0.1 mol.) of p-methoxyphenol and 13.8 g. (0.1 mol.) of potassium carbonate in 75 ml. of dry acetone is refluxed with stirring for 16 hours. After cooling, the reaction mixture is poured into 500 ml. of water. The product is collected an... | COc1ccc(OCC(=O)c2ccc(OCCCl)cc2)cc1 | null | null | null |
1,354,614 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | [NH2:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][OH:7].[CH3:8][Si:9]([CH3:24])([CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[CH2:10][CH2:11][CH2:12][O:13][CH2:14][CH:15]1[CH2:17][O:16]1>C(O)C>[CH3:24][Si:9]([CH3:8])([CH2:18][CH2:19][Si:20]([CH3:21])([CH3:23])[CH3:22])[CH2:10][CH2:11][CH2:12][O:13][CH2:14][CH:15]([OH:16]... | C[Si](C)(C)CC[Si](C)(C)CCCOCC1CO1 | NCCOCCO | 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 | 70 | null | 2-(2-amino-ethoxy)-ethanol (3.83 g; 36.4 mMol) and 40 mL of ethanol were charged to a 100 mL RB flask equipped with a magnetic stirrer. The mixture was stirred and heated to 70° C. 2-{3-[Dimethyl-(2-trimethylsilanyl-ethyl)-silanyl]-propoxymethyl}-oxirane 8 (2 g; 7.28 mMol) mixed with 10 g ethanol was placed in an addit... | C[Si](C)(C)CC[Si](C)(C)CCCOCC(O)CNCCOCCO | null | null | null |
240,295 | ord_dataset-685186618e9f4e7aaa72ac40c16ef354 | null | 1992-01-01T00:01:00 | true | [NH2:1][C:2]1[C:7]2[C:8](=[O:18])[C:9]3[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=3[NH:11][C:12](=[O:13])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:19](O)(=[O:21])[CH3:20].O>O1CCOCC1>[C:19]([NH:1][C:2]1[C:7]2[C:8](=[O:18])[C:9]3[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=3[NH:11][C:12](=[O:13])[C:6]=2[CH:5]=[CH:4][CH:3]=1)(=[O:21])[CH3:20] | Nc1cccc2c(=O)[nH]c3ccccc3c(=O)c12 | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | To 2.5 g 10-amino-5,6-dihydro-11H-dibenzo(b,e)azepine-6,11-dione in 50 ml dioxane are added 2 ml anhydrous acetic acid. This mixture is kept at reflux for 2 hours then brought almost to dryness under reduced pressure, and then poured into water, filtered and dried. Yield 2 g (ethanol): melting point 270°-2° C. | CC(=O)Nc1cccc2c(=O)[nH]c3ccccc3c(=O)c12 | null | null | null |
91,640 | ord_dataset-90c12c4a89ae46d88aea27f4e37ba124 | null | 1982-01-01T00:02:00 | true | [CH3:1][N:2]([CH3:17])[CH:3]=[C:4]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1[N+:14]([O-:16])=[O:15])[CH:5]=O.[N+:18]([CH2:21][C:22]([O:24][CH3:25])=[O:23])([O-:20])=[O:19]>C(OC(=O)C)(=O)C>[CH3:25][O:24][C:22](=[O:23])[C:21]([N+:18]([O-:20])=[O:19])=[CH:5][C:4]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1... | CN(C)C=C(C=O)c1ccc(Cl)cc1[N+](=O)[O-] | COC(=O)C[N+](=O)[O-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)OC(C)=O | null | null | null | null | null | null | null | null | null | null | 25 | null | A mixture of 73.1 g (0.29 mol) of the compound of Example 13, 34.0 g (0.29 mol) of methyl nitroacetate and 600 ml of acetic anhydride was stirred and heated at 90°-95° for 45 minutes. The reaction mixture was allowed to cool to room temperature and the crystalline product was collected by filtration. the filtrate was c... | COC(=O)C(=CC(=CN(C)C)c1ccc(Cl)cc1[N+](=O)[O-])[N+](=O)[O-] | null | 88.2 | null |
389,882 | ord_dataset-44d518e567bd4c039d77233023f78bb2 | null | 1998-01-01T00:01:00 | true | S(=O)(=O)(O)O.[CH2:6]([CH:8]([CH2:11][CH2:12][CH2:13][CH3:14])[CH2:9][OH:10])[CH3:7].[C:15](O)(=[O:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21]>C1(C)C=CC=CC=1>[CH2:6]([CH:8]([CH2:11][CH2:12][CH2:13][CH3:14])[CH2:9][O:10][C:15](=[O:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])[CH3:7] | CCCCC(CC)CO | CC(C)CCCCC(=O)O | null | O=S(=O)(O)O | 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 | null | 2 g concentrated sulfuric acid were added to a solution of 130 g (1 mol) 2-ethylhexanol and 144 g (1 mol) "isooctanoic acid" (isomeric mixture from Ruhrchemie A. G., Oberhausen) in 300 ml toluene and heated to boiling with water separation until the equimolar amount of water separates (about 2 hours). After cooling it ... | CCCCC(CC)COC(=O)CCCCC(C)C | null | null | null |
1,125,185 | ord_dataset-285df12e34cd46e993e3c8ebc3a8962a | null | 2012-01-01T00:01:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[C:4]([CH2:11][CH:12]=[CH2:13])[CH:3]=1>CO.[OH-].[OH-].[Pd+2]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([CH2:11][CH2:12][CH3:13])[CH:3]=1 | C=CCc1cc(F)ccc1[N+](=O)[O-] | null | null | [Pd+2] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | 8 | To 4-fluoro-1-nitro-2-(2-propen-1-yl)benzene (9.0 g, 50 mmol) in MeOH (100 mL) was added palladium hydroxide on carbon (2 g). The reaction mixture was stirred under H2 (50 psi) at rt overnight. The solution was filtered and concentrated to provide the title compound of step C (7.4 g, 48.3 mmol, 97%). 1H NMR (400 MHz, C... | CCCc1cc(F)ccc1N | null | 96.6 | null |
1,442,879 | ord_dataset-275a3da8f45f4536ad29727f0ef9ba66 | null | 2014-01-01T00:06:00 | true | [NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:12]3[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13]3)[N:9]=[C:10](I)[C:3]=12.[O:25]([C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.C1... | CC(C)(C)OC(=O)N1CCCC(n2nc(I)c3c(N)ncnc32)C1 | OB(O)c1ccc(Oc2ccccc2)cc1 | 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 | O | null | null | null | null | null | null | null | null | null | 90 | 24 | A mixture of tert-butyl 3-[4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylate (1 g, 2.25 mmol, 1.00 equiv), (4-phenoxyphenyl)boronic acid (530 mg, 2.48 mmol, 1.10 equiv), sodium carbonate (480 mg, 4.53 mmol, 2.01 equiv) and tetrakis(triphenylphosphine)palladium (78 mg, 0.07 mmol, 0.03 equiv) in 1,... | CC(C)(C)OC(=O)N1CCCC(n2nc(-c3ccc(Oc4ccccc4)cc3)c3c(N)ncnc32)C1 | null | 63.9 | null |
1,519,647 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | [C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C@@H:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C@H:17]([O:24][C:25]3[CH:26]=[CH:27][C:28]4[N:29]([C:31]([N:34]5[C@H:39]([CH3:40])[CH2:38][CH2:37][CH2:36][C@@H:35]5[CH3:41])=[N:32][N:33]=4)[CH:30]=3)[CH2:16][CH2:15]2)=[O:12])[N:7]([CH2:42][CH2:43]OS(C)(=O)=O)[N:6]... | C1COCCN1 | C[C@@H]1CCC[C@H](C)N1c1nnc2ccc(O[C@@H]3CC[C@H](NC(=O)Nc4cc(C(C)(C)C)nn4CCOS(C)(=O)=O)c4ccccc43)cn12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | 50 | 24 | To a solution of Intermediate 121a (0.07 mmol) in THF (2 mL) was added DIPEA (50 μL, 0.29 mmol) and morpholine (25 μL, 0.29 mmol) and the reaction stirred at 50° C. for 24 h. The crude reaction mixture was cooled and partitioned between EtOAc and water. The aqueous phase was extracted with EtOAc (×3) and the combined o... | C[C@@H]1CCC[C@H](C)N1c1nnc2ccc(O[C@@H]3CC[C@H](NC(=O)Nc4cc(C(C)(C)C)nn4CCN4CCOCC4)c4ccccc43)cn12 | null | 40.5 | null |
1,544,669 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | [CH2:1]([O:3][C:4](=[O:23])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[C:17]([NH2:18])=[CH:16][CH:15]=[C:14]([S:19]([CH3:22])(=[O:21])=[O:20])[N:13]=2)[CH2:8][CH2:7]1)[CH3:2].C(N(CC)C(C)C)(C)C.[Cl:33][C:34]1[CH:35]=[C:36]([CH:40]=[CH:41][CH:42]=1)[C:37](Cl)=[O:38]>C(#N)C>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][CH:6]1[CH2:11... | O=C(Cl)c1cccc(Cl)c1 | CCOC(=O)CC1CCN(c2nc(S(C)(=O)=O)ccc2N)CC1 | 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 | CC#N | null | null | null | null | null | null | null | null | null | 80 | 0.17 | To a mixture of 0.080 g (0.23 mmol) of (3′-amino-6′-methanesulfonyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-acetic acid ethyl ester in acetonitrile (5 mL) is added 0.12 mL (0.70 mmol) of N,N-diisopropylethylamine followed by 0.032 mL (0.28 mmol) of 3-chlorobenzoyl chloride. The mixture is heated at 80° C. for 1 h... | CCOC(=O)CC1CCN(c2nc(S(C)(=O)=O)ccc2NC(=O)c2cccc(Cl)c2)CC1 | null | 49.8 | null |
1,550,472 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | [C:1]([C:4]1[C:5]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)=[N:6][N:7]([CH:9]2[CH2:14][CH2:13][CH:12]([C:15]([O:17]C(C)(C)C)=[O:16])[CH2:11][CH:10]2[C:22]#[N:23])[CH:8]=1)(=[O:3])[NH2:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]([C:4]1[C:5]([NH:24][C:25]2[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=2)=[N:6][... | CC(C)(C)OC(=O)C1CCC(n2cc(C(N)=O)c(Nc3ccc(Cl)cc3)n2)C(C#N)C1 | 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 | 16 | To a solution of (1S,3S,4S and 1R,3R,4R)-t-butyl 4-[4-carbamoyl-3-[(4-chlorophenyl)amino]-1H-pyrazol-1-yl]-3-cyanocyclohexane-1-carboxylate (500 mg, 1.1 mmol) in DCM (4 mL) was added TFA (2 mL) at 0° C. The resulting solution was stirred at ambient temperature for 16 hours and then concentrated in vacuo to afford the t... | N#CC1CC(C(=O)O)CCC1n1cc(C(N)=O)c(Nc2ccc(Cl)cc2)n1 | null | null | null |
1,620,135 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=O)[CH:5]=[CH:6][C:7]=1[F:8].[CH3:13]N1C=CN=C1>C(OC(=O)C)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10](=[O:12])[CH3:13])[CH:5]=[CH:6][C:7]=1[F:8] | Cn1ccnc1 | O=C(O)Cc1ccc(F)c(Cl)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)OC(C)=O | null | null | null | null | null | null | null | null | null | null | 25 | 8 | To a solution of 2-(3-chloro-4-fluorophenyl)acetic acid (18.46 g, 97.89 mmol) in acetic anhydride (463 mL) was added N-methylimidazole (3.9 mL) and the reaction mixture was stirred overnight at room temperature. The reaction mixture was partitioned between ethyl acetate and saturated sodium bicarbonate solution and org... | CC(=O)Cc1ccc(F)c(Cl)c1 | null | 79 | null |
1,632,113 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | Cl[C:2]1[C:7]([NH:8][C:9](=[O:22])[C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH:18]3[CH2:20][CH2:19]3)=[C:12]([F:21])[CH:11]=2)=[CH:6][N:5]=[C:4]([O:23][CH2:24][C@@H:25]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH3:26])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.[Cu]I>[CH:18]1([CH2:17][O:16][C... | C[C@@H](COc1cc(Cl)c(NC(=O)c2ccc(OCC3CC3)c(F)c2)cn1)NC(=O)OC(C)(C)C | null | null | [Cu]I | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 160 | 5 | A suspension of tert-butyl ((2S)-1-((4-chloro-5-((4-(cyclopropylmethoxy)-3-fluorobenzoyl)amino)pyridin-2-yl)oxy)propan-2-yl)carbamate (990 mg), potassium carbonate (554 mg) and copper(I) iodide (38.2 mg) in DMF (10 mL) was stirred at 160° C. for 5 hr under microwave irradiation. To the reaction mixture was added water,... | C[C@@H](COc1cc2oc(-c3ccc(OCC4CC4)c(F)c3)nc2cn1)NC(=O)OC(C)(C)C | null | 42.9 | null |
1,721,483 | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | null | 2016-01-01T00:05:00 | true | [C:1]([N:9]=[C:10]=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:12][C:13]1[CH:14]=[N:15][C:16]([N:19]2[CH2:26][CH:25]3[C:21]([C:27]4[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=4)([NH:22][O:23][CH2:24]3)[CH2:20]2)=[N:17][CH:18]=1>O1CCCC1>[F:12][C:13]1[CH:18]=[N:17][C:16]([N:19]2[CH2:26][CH:25]3[C:21]([C:27]4[CH:2... | O=C(N=C=S)c1ccccc1 | Fc1cnc(N2CC3CONC3(c3cccnc3)C2)nc1 | 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 | 0 | 1 | Benzoyl isothiocyanate (511 μL 3.79 mmol) is added drop wise to a stirred solution of 5-(5-fluoropyrimidin-2-yl)-6a-(3-pyridyl)-3,3a,4,6-tetrahydro-1H-pyrrolo[3,4-c]isoxazole (640 mg, 2.23 mmol) in tetrahydrofuran (20 mL) at 0° C. The resulting mixture is stirred at 0° C. for 1 hour and is warmed to room temperature ov... | O=C(NC(=S)N1OCC2CN(c3ncc(F)cn3)CC21c1cccnc1)c1ccccc1 | null | 109.5 | null |
1,338,253 | ord_dataset-08852243bba44cb28769a5833f1515fe | null | 2013-01-01T00:09:00 | true | [NH:1]1[CH2:6][CH2:5][O:4][CH:3]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:2]1.CCN(C(C)C)C(C)C.[C:26](OC(=O)C)(=[O:28])[CH3:27]>ClCCl>[C:26]([N:1]1[CH2:6][CH2:5][O:4][CH:3]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:2]1)(=[O:28])[CH3:27] | CC(=O)OC(C)=O | O=C(OCc1ccccc1)C1CNCCO1 | 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 | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 18 | Phenylmethyl 2-morpholinecarboxylate (450 mg, 2.034 mmol) was dissolved in dichloromethane (30 ml). DIPEA (0.71 ml, 4.07 mmol) and acetic anhydride (0.23 ml, 2.441 mmol) were added and the mixture was stirred under nitrogen at room temperature for 18 hr. The solvent was removed in vacuo, the residue was portioned betwe... | CC(=O)N1CCOC(C(=O)OCc2ccccc2)C1 | null | 58.5 | null |
1,557,018 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@H:9]2[CH2:11][C@@H:10]2[CH2:12][O:13][C:14]2[C:23]([CH:24]3[CH2:29][CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25]3)=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][N:20]=3)[N:15]=2)=[N:7][CH:8]=1.C(O)(C(F)(F)F)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@H:9... | COc1ccc([C@H]2C[C@@H]2COc2nc3cccnc3cc2C2CCCN(C(=O)OC(C)(C)C)C2)nc1 | null | null | O=C([O-])O | [Na+] | 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 | null | 0.08 | To a solution of tert-butyl 3-(2-{[(1S,2S)-2-(5-methoxypyridin-2-yl)cyclopropyl]methoxy}-1,5-naphthyridin-3-yl)piperidine-1-carboxylate (RR2) (38 mg, 0.08 mmol) in DCM (3 mL) was added concentrated TFA (0.5 mL, 6.5 mmol). After five minutes, saturated sodium bicarbonate (3 mL) was added and the mixture was extracted wi... | COc1ccc([C@H]2C[C@@H]2COc2nc3cccnc3cc2C2CCCNC2)nc1 | null | null | null |
1,744,404 | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | null | 2016-01-01T00:07:00 | true | C([O:4][CH2:5][CH2:6][N:7]([C@H:12]1[C:20]2[C:15](=[C:16]([C:21]3[N:25]=[C:24]([C:26]4[CH:31]=[CH:30][C:29]([O:32][CH:33]([CH3:35])[CH3:34])=[C:28]([C:36]#[N:37])[CH:27]=4)[O:23][N:22]=3)[CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13]1)[S:8]([CH3:11])(=[O:10])=[O:9])(=O)C.C([O-])([O-])=O.[K+].[K+]>CO.O>[C:36]([C:28]1[CH:27]=... | CC(=O)OCCN([C@@H]1CCc2c(-c3noc(-c4ccc(OC(C)C)c(C#N)c4)n3)cccc21)S(C)(=O)=O | null | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | O | null | null | null | null | null | null | null | null | null | 25 | 2 | To a solution of (R)-2-(N-(4-(5-(3-cyano-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-yl)methylsulfonamido)ethyl acetate (12 mg, 0.22 mmol) in a 1:1 mixture of MeOH/H2O was added K2CO3 (9.48 mg, 0.06 mmol). The reaction mixture was stirred at room temperature for 2 h and concentrated to dryness. The... | CC(C)Oc1ccc(-c2nc(-c3cccc4c3CC[C@H]4N(CCO)S(C)(=O)=O)no2)cc1C#N | null | null | null |
1,174,520 | ord_dataset-0f9d2dbe929a45c3892ae75e81e99443 | null | 2012-01-01T00:06:00 | true | C([N:8](C(OC(C)(C)C)=O)[C@H:9]1[CH2:13][C@@H:12]([N:14]2[CH:22]=[N:21][C:20]3[C:15]2=[N:16][C:17]([Cl:24])=[N:18][C:19]=3[Cl:23])[C@H:11]([OH:25])[C@@H:10]1[OH:26])(OC(C)(C)C)=O.ClC1N=C2C(N=CN2[C@@H]2C[C@H](N3[N:53]=[C:52]([CH2:54][CH3:55])[CH:51]=[N:50]3)C=C2)=C(Cl)N=1>>[Cl:24][C:17]1[N:16]=[C:15]2[C:20]([N:21]=[CH:22... | CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)[C@H]1C[C@@H](n2cnc3c(Cl)nc(Cl)nc32)[C@H](O)[C@@H]1O | CCc1cnn([C@@H]2C=C[C@H](n3cnc4c(Cl)nc(Cl)nc43)C2)n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The titled compound is prepared analogously to (1S,2R,3S,5R)-3-(di-Boc-amino)-5-(2,6-dichloro-purin-9-yl)-cyclopentane-1,2-diol (AA4) by replacing di-Boc-[(1S,4R)-4-(2,6-dichloro-purin-9-yl)-cyclopent-2-enyl]-amine with 2,6-dichloro-9-[(1R,4S)-4-(4-ethyl-[1,2,3]triazol-2-yl)-cyclopent-2-enyl]-9H-purine (Step 1). | CCc1cnn([C@H]2C[C@@H](n3cnc4c(Cl)nc(Cl)nc43)[C@H](O)[C@@H]2O)n1 | null | null | null |
759,219 | ord_dataset-2e58cb8db2bf482bbea23283b7e04488 | null | 2007-01-01T00:03:00 | true | [Cl:1][C:2]1[C:7]([C:8]([C:10]2[NH:14][CH:13]=[C:12]([S:15](Cl)(=[O:17])=[O:16])[CH:11]=2)=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(CC)CC)C>C(Cl)Cl>[CH2:19]([NH:26][S:15]([C:12]1[CH:11]=[C:10]([C:8]([C:7]2[C:2]([Cl:1])=[N:3][CH:4]=[CH:5][CH:6]=2)=[O:9])[NH:1... | O=C(c1cc(S(=O)(=O)Cl)c[nH]1)c1cccnc1Cl | NCc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 25 | 4 | A mixture of 5-(2-chloro-pyridine-3-carbonyl)-1H-pyrrole-3-sulfonyl chloride (500 mg, 1.64 mmol) (from Example 17), benzylamine (351.5 mg, 3.28 mmol) and triethylamine (1 mL) in DCM (5 mL) was stirred at room temperature for 4 hours. The reaction was diluted with DCM, washed with water, dried and concentrated. The resi... | O=C(c1cc(S(=O)(=O)NCc2ccccc2)c[nH]1)c1cccnc1Cl | null | null | null |
373,367 | ord_dataset-ee5599340390470d8e5b5ac1feddf9d6 | null | 1997-01-01T00:08:00 | true | [NH2:1][CH:2]([CH3:34])[CH2:3][CH2:4][N:5](CC1C=CC=CC=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][N:14]([CH2:22][CH2:23][CH:24]([NH2:26])[CH3:25])CC1C=CC=CC=1>[OH-].[OH-].[Pd+2].C(O)C>[NH2:26][CH:24]([CH3:25])[CH2:23][CH2:22][NH:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][NH:5][CH... | CC(N)CCN(CCCCCCCCN(CCC(C)N)Cc1ccccc1)Cc1ccccc1 | null | null | [Pd+2] | [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 | Combine 5.0 g (0.01 mol) of the product of Step D, 0.5 g of 20% Pd(OH)2 on carbon (Pearlman's Catalyst), and 50 ml of ethanol and treat the mixture with H2 at 45 lb/in2 in a shaker flask until no more gas is taken up. Remove the catalyst by filtration and remove the solvent at reduced pressure. Subject the residue to s... | CC(N)CCNCCCCCCCCNCCC(C)N | null | 55.5 | null |
1,220,957 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:8]=1)(=O)=O.[CH3:19][N:20](C=O)C>CCOCC.[C-]#N.[Zn+2].[C-]#N>[C:13]([C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=1)[C:19]#[N:20])([CH3:16])([CH3:15])[CH3:14] | CC(C)(C)c1cccc(OS(=O)(=O)C(F)(F)F)c1 | CN(C)C=O | null | [C-]#N | [Zn+2] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | null | null | null | null | null | null | null | null | null | null | 120 | null | To a solution of 3-tert-butylphenyl trifluoromethanesulfonate (1.5 g, 6.70 mmol) in DMF (10 mL), zinc cyanide (1.57 g, 13.40 mmol) was added. The reaction mixture was heated to 120° C. for 4 h. Then reaction mixture was cooled, diluted with ether (2500 mL) and washed twice with 2N ammonium hydroxide (50 mL). The ether ... | CC(C)(C)c1cccc(C#N)c1 | null | 75 | null |
573,441 | ord_dataset-f4512fe8cd804ac79da66cbc0c2b9d42 | null | 2002-01-01T00:12:00 | true | [CH2:1]([C:3]1([CH2:19][CH3:20])[C:7](=[O:8])[CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:11][CH:10]=2)[O:4]1)[CH3:2].C(O)(=O)C.[Br:25]Br>C(Cl)(Cl)Cl>[Br:25][C:6]1[C:7](=[O:8])[C:3]([CH2:1][CH3:2])([CH2:19][CH3:20])[O:4][C:5]=1[C:9]1[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16... | CCC1(CC)OC(c2ccc(S(C)(=O)=O)cc2)=CC1=O | BrBr | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | 25 | 4 | To a stirred solution of 2,2-diethyl-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone (4.5 g) in 200 ml chloroform with 3 ml acetic acid, was added dropwise 1.5 ml bromine at 0° C. The solution was then allowed to warm to room temperature and was stirred for another 4 hours. The reaction was quenched by adding saturated aqu... | CCC1(CC)OC(c2ccc(S(C)(=O)=O)cc2)=C(Br)C1=O | null | null | null |
1,539,606 | ord_dataset-8d5c200bca27407ab9febe7598e16458 | null | 2015-01-01T00:01:00 | true | [F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[C:4]([NH:20][C:21]1[CH:22]=[N:23][CH:24]=[C:25]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)[CH:26]=1)=[C:5]([CH3:19])[C:6]([N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)=[N:7]2.[O:33]1[CH:37]=[C:36]([C:38](O)=[O:39])[N:35]=[CH:34]1>>[F:1][C:2]1[CH:11]=[C:10]([... | O=C(O)c1cocn1 | Cc1c(N2CCNCC2)nc2cc(F)cc(F)c2c1Nc1cncc(N2CCOCC2)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 | Prepared according to Procedure Q using 5,7-difluoro-3-methyl-N-(5-morpholinopyridin-3-yl)-2-(piperazin-1-yl)quinolin-4-amine (40.0 mg, 0.09 mmol) and oxazole-4-carboxylic acid to give (4-(5,7-difluoro-3-methyl-4-(5-morpholinopyridin-3-ylamino)quinolin-2-yl)piperazin-1-yl)(oxazol-4-yl)methanone. 1H NMR (DMSO-d6) δ ppm ... | Cc1c(N2CCN(C(=O)c3cocn3)CC2)nc2cc(F)cc(F)c2c1Nc1cncc(N2CCOCC2)c1 | null | null | null |
180,208 | ord_dataset-ed5a3d1f8dc744759e7fa1c320a44e59 | null | 1988-01-01T00:11:00 | true | [C:1]([CH2:3][NH:4][C:5]([C:7]1[C:8]([CH3:13])=[CH:9][CH:10]=[CH:11][CH:12]=1)=[O:6])#[N:2].[Cl:14][C:15]([Cl:19])([Cl:18])[S:16]Cl.C(N(CC)CC)C>C(Cl)Cl>[C:1]([CH2:3][N:4]([S:16][C:15]([Cl:19])([Cl:18])[Cl:14])[C:5]([C:7]1[C:8]([CH3:13])=[CH:9][CH:10]=[CH:11][CH:12]=1)=[O:6])#[N:2] | Cc1ccccc1C(=O)NCC#N | ClSC(Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | ClCCl | null | null | null | null | null | null | null | null | null | null | 0.5 | To a stirred mixture of 5.0 g (0.029 mole) N-cyanomethyl-o-toluamide (the product of Example 10) and 5.8 g (0.031 mole) trichloromethylsulfenyl chloride in 125 ml methylene chloride, 3.6 g (0.036 mole) triethylamine in 25 ml methylene chloride were added dropwise over 40 minutes. The reaction mixture was stirred 30 min... | Cc1ccccc1C(=O)N(CC#N)SC(Cl)(Cl)Cl | null | 59.7 | null |
638,043 | ord_dataset-a192df1b44174b5886ef2005f759d553 | null | 2004-01-01T00:05:00 | true | C(Cl)(=O)C(Cl)=O.[Cl:7][C:8]1[CH:9]=[C:10]([C:14]2[C:23]3[C:18](=[N:19][C:20]([CH3:24])=[CH:21][CH:22]=3)[N:17]([CH2:25][CH3:26])[C:16](=[O:27])[C:15]=2[CH2:28][CH2:29][C:30]([OH:32])=O)[CH:11]=[CH:12][CH:13]=1.[NH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1.Cl>CN(C=O)C.C1COCC1>[Cl:7][C:8]1[CH:9]=[C:10]([C:14]2[C:23]3[... | C1COCCN1 | CCn1c(=O)c(CCC(=O)O)c(-c2cccc(Cl)c2)c2ccc(C)nc21 | null | Cl | O=C(Cl)C(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 0.5 | A 0.3 ml portion of oxalyl chloride and one drop of DMF were added to a 20 ml THF solution containing 1.00 g of 3-[4-(3-chlorophenyl)-l-ethyl-7-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]propanoic acid, followed by stirring at room temperature for further 30 minutes. The reaction mixture was added dropwise to an ic... | CCn1c(=O)c(CCC(=O)N2CCOCC2)c(-c2cccc(Cl)c2)c2ccc(C)nc21 | null | null | null |
980,049 | ord_dataset-35b56288528641309a040cc2b6710b61 | null | 2010-01-01T00:08:00 | true | [N:1]1([C:7]2[N:12]=[C:11]([NH:13][C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)[CH:10]=[C:9]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([O:26]CC4C=CC=CC=4)[CH:21]=3)[N:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(#N)C.[ClH:37]>C(O)C>[N:1]1([C:7]2[N:8]=[C:9]([C:20]3[CH:21]=[C:22]([OH:26])[CH:23]=[CH:24][CH:25]=3)[CH:10]=[C:11](... | c1ccc(COc2cccc(-c3cc(Nc4cccnc4)nc(N4CCOCC4)n3)c2)cc1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | CCO | null | null | null | null | null | null | null | null | null | null | 20 | {2-Morpholin-4-yl-6-[3-(phenylmethoxy)phenyl]pyrimidin-4-yl}-3-pyridylamine (1 eq) is suspended in ethanol in a round bottom flask, purged with N2. 10% Pd/C (20% wt) was added. The flask was evacuated and filled up with H2 (contained in a balloon) for five times, then the reaction mixture was stirred under H2 for 20 h.... | Oc1cccc(-c2cc(Nc3cccnc3)nc(N3CCOCC3)n2)c1 | null | null | null |
913,314 | ord_dataset-c663259b80f947e2a8923796fb0e9a6b | null | 2009-01-01T00:10:00 | true | [C:1]([OH:11])(=[O:10])[C:2]1[NH:9][C:7](=[O:8])[NH:6][C:4](=[O:5])[CH:3]=1.[OH-].[Na+:13].CCO>O>[C:1]([O-:11])(=[O:10])[C:2]1[NH:9][C:7](=[O:8])[NH:6][C:4](=[O:5])[CH:3]=1.[Na+:13] | O=C(O)c1cc(=O)[nH]c(=O)[nH]1 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | O | null | null | null | null | null | null | null | null | null | null | 1 | FIG. 2 illustrates the synthesis of Sodium Methotrexate Orotate. Orotic acid (1.74 g) was treated with sodium hydroxide (0.45 g) in water (100 mL). The mixture was warmed, stirred for 1 h and stored in the refrigerator overnight. Etanol (30 mL) was added to the solution and the precipitate was collected by filtration t... | O=C([O-])c1cc(=O)[nH]c(=O)[nH]1 | null | null | null |
763,913 | ord_dataset-7a8649d55889427e85b208ae89475895 | null | 2007-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]([OH:14])=O)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[NH2:15][CH2:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][CH:22]([C:25]2[CH:26]=[C:27]([NH:31][C:32](=[O:34])[CH3:33])[CH:28]=[CH:29][CH:30]=2)[CH2:21][CH2:20]1>>[C:32]([NH:31][C:27]1[CH:26]=[C:25]([CH:22]2[CH2:23][CH2:24][N:... | CC(=O)Nc1cccc(C2CCN(CCCN)CC2)c1 | O=C(O)C1(c2ccc(Cl)cc2)CCC1 | null | null | null | null | null | null | null | 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 74 was prepared from 1-(4-chlorophenyl)cyclo butanecarboxylic acid and N-{3-[1-(3-aminopropyl)-4-piperidinyl]phenyl}acetamide according to the procedures described in Scheme 10: 1H NMR (400 MHz, CDCl3) δ 7.55 (s, 1H), 7.36–7.26 (m, 7H), 6.97 (d, 1H, J=7.2 Hz), 6.50 (brs, 1H), 3.30 (dd, 2H, J=6.0, 12.0 Hz), 2.98... | CC(=O)Nc1cccc(C2CCN(CCCNC(=O)C3(c4ccc(Cl)cc4)CCC3)CC2)c1 | null | null | null |
543,989 | ord_dataset-49124ff635234889bd8dcfe87f4f9013 | null | 2002-01-01T00:04:00 | true | [CH2:1]([O:3][C:4]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]#[C:14][Si](CC)(CC)CC)=[CH:9][C:8]=2[C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:6][CH2:5]1)[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CO>[CH2:1]([O:3][C:4]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]#[CH:14])=[CH:9][C:8]=2[C:22]([CH3:23])([CH3:25])[CH3:24])[CH2:6][CH2:5]1)[CH3:2] | CCOC1(c2ccc(C#C[Si](CC)(CC)CC)cc2C(C)(C)C)CC1 | null | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | 8 | Using General Procedure E; [4-(1-ethoxycyclopropyl)-3-tert-butyl-phenylethynyl]-triethylsilane (Intermediate 111, 215.0 mg, 0.69 mmol) in methanol (10 mL) was treated with potassium carbonate (80.0 mg, 0.58 mmol) and stirred overnight at ambient temperature. The crude alkyne, 169 mg, was used directly in the next react... | C#Cc1ccc(C2(OCC)CC2)c(C(C)(C)C)c1 | null | null | null |
596,695 | ord_dataset-843ef38b45484f72826f5f39d8a29c4d | null | 2003-01-01T00:06:00 | true | [I:1]N1C(=O)CCC1=O.[CH3:9][C:10]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][CH:13]=[CH:12][C:11]=1[C:19]([F:22])([F:21])[F:20]>OS(O)(=O)=O>[I:1][C:13]1[CH:14]=[C:15]([N+:16]([O-:18])=[O:17])[C:10]([CH3:9])=[C:11]([C:19]([F:20])([F:21])[F:22])[CH:12]=1 | Cc1c([N+](=O)[O-])cccc1C(F)(F)F | O=C1CCC(=O)N1I | 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 | 2.5 | 0.67 | To H2SO4 (110 mL, 96%) stirring under a nitrogen atmosphere at 0-5° C. was added N-iodosuccinimide (41.13 g, 1.5 eq). The resulting black/dark red mixture was stirred at 0-5° C. for 40 minutes. To this was added dropwise commercially available 2-methyl-3-nitrobenzotrifluoride (25.0 g, 121.9 mmol) in H2SO4 (75 mL). Once... | Cc1c([N+](=O)[O-])cc(I)cc1C(F)(F)F | null | null | null |
1,268,588 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | [F:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([F:11])[C:7]=1[C:8]([OH:10])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[Cl:45][C:46]1[CH:51]=[C:50]([Cl:52])[CH:49]=[CH:48][C:47]=1[CH2:53][N:54]1[CH:58]=[CH:57][C:56]([NH2:59])=[N:55]1>CN(C)C=O>[Cl:45][C:46]1[CH:51]=[C:50]([Cl:52])[CH:49]=[CH:48][C:4... | Nc1ccn(Cc2ccc(Cl)cc2Cl)n1 | O=C(O)c1c(F)cncc1F | 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 | CN(C)C=O | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | null | 0.08 | To a solution of 3,5-difluoro-4-pyridinecarboxylic acid (15.9 mg, 0.1 mmol, Frontier Scientific) in dimethylformamide (0.1 ml) was added HATU (38 mg, 0.1 mmol) in dimethylformamide (0.2 mL), followed by N,N-diisopropylethylamine (0.050 ml, 0.286 mmol) and the resulting solution left for 5 min. Finally, a solution of 1-... | O=C(Nc1ccn(Cc2ccc(Cl)cc2Cl)n1)c1c(F)cncc1F | null | 114.8 | null |
743,848 | ord_dataset-437aa6654d5044ddaef3346dc4c6e08a | null | 2006-01-01T00:11:00 | true | [N+:1]([C:4]1[N:9]=[CH:8][C:7]([CH:10](C(OCC)=O)[C:11]([O:13][CH2:14][C:15]2C=CC=CC=2)=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2]>C(O)C.[Pd]>[N+:1]([C:4]1[N:9]=[CH:8][C:7]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2] | CCOC(=O)C(C(=O)OCc1ccccc1)c1ccc([N+](=O)[O-])nc1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 25 | 6 | To a solution of benzyl ethyl 2-(6-nitro-3-pyridinyl)malonate (5.26 g, 15.3 mmol,) in ethanol was added palladium on carbon (530 mg) and stirred for 6 h under hydrogen atmosphere at room temperature. The catalyst was filtered off through a pad of celite and the filtrate was concentrated to give a title compound as yell... | CCOC(=O)Cc1ccc([N+](=O)[O-])nc1 | null | null | null |
906,795 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | [CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:44]=[CH:43][C:16]([CH2:17][N:18]([C:30]3[CH:42]=[CH:41][C:33]4[O:34]C(C)(C)[O:36][C:37](=[O:38])[C:32]=4[CH:31]=3)[C:19]([C:21]3[S:22][C:23]4[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=4[CH:25]=3)=[O:20])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na... | CCCCc1ccc(C#Cc2ccc(CN(C(=O)c3cc4ccccc4s3)c3ccc4c(c3)C(=O)OC(C)(C)O4)cc2)cc1 | 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 | The titled compound was prepared following the procedure C using N-{4-[(4-butylphenyl)ethynyl]benzyl}-N-(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-6-yl)-1-benzothiophene-2-carboxamide and NaOH 5M aq. in the presence of EtOH as a beige powder (37%). 1H NMR (CDCl3/MeOD 35:1, 300 MHz) δ 7.67 (m, 3H), 7.45-7.24 (m, 9H) 7.11 (m... | CCCCc1ccc(C#Cc2ccc(CN(C(=O)c3cc4ccccc4s3)c3ccc(O)c(C(=O)O)c3)cc2)cc1 | null | null | null |
1,043,379 | ord_dataset-3af92aec23dc4810b92eb0d8c60023ee | null | 2011-01-01T00:03:00 | true | Cl.CN.[CH2:4]([N:6](CC)CC)C.[F:11][C:12]1[CH:20]=[CH:19][C:18]([I:21])=[CH:17][C:13]=1[C:14](Cl)=[O:15]>ClCCl>[F:11][C:12]1[CH:20]=[CH:19][C:18]([I:21])=[CH:17][C:13]=1[C:14]([NH:6][CH3:4])=[O:15] | CCN(CC)CC | O=C(Cl)c1cc(I)ccc1F | null | CN | 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 | 25 | 20 | Add methylamine hydrochloride (0.57 g, 8.4 mmol) and triethylamine (2.17 mL, 15.5 mmol) to a solution of 2-fluoro-5-iodobenzoyl chloride (2.0 g, 7.0 mmol) in dichloromethane (100 mL) at 0° C. Warm to room temperature and stir 20 h. Concentrate and purify by silica gel chromatography, eluting with a gradient of 75:25 to... | CNC(=O)c1cc(I)ccc1F | null | 87 | null |
1,641,699 | ord_dataset-bcc0b01d4f58457a8733b10a099f43ba | null | 2015-01-01T00:10:00 | true | C([O:3][C:4](=[O:20])[CH2:5][CH:6]([N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[NH:12][C:11]1=[O:19])[CH2:7][CH2:8][CH3:9])C.C(=O)([O-])[O-].[K+].[K+].Br[CH2:28][C:29]1[CH:34]=[C:33]([CH3:35])[CH:32]=[CH:31][C:30]=1[CH3:36]>CN(C=O)C>[CH3:36][C:30]1[CH:31]=[CH:32][C:33]([CH3:35])=[CH:34][C:29]=1[CH2:28][N:12]1[C... | Cc1ccc(C)c(CBr)c1 | CCCC(CC(=O)OCC)n1c(=O)[nH]c2ccccc21 | 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 | 80 | 8 | 3-(2-Oxo-2,3-dihydro-benzoimidazol-1-yl)-hexanoic acid ethyl ester (40 mg, 0.145 mmol), prepared as described above, was dissolved in DMF (1 mL), and potassium carbonate (69 mg, 0.50 mmol) was added followed by 2-bromomethyl-1,4-dimethyl-benzene (56.3 mg, 0.28 mmol). The resulting mixture was heated at 80° C. for 4 h, ... | CCCC(CC(=O)O)n1c(=O)n(Cc2cc(C)ccc2C)c2ccccc21 | null | 47 | null |
571,974 | ord_dataset-f4512fe8cd804ac79da66cbc0c2b9d42 | null | 2002-01-01T00:12:00 | true | [NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:10]([N:12]2[CH2:16][CH:15]([C:17]([F:20])([F:19])[F:18])[CH:14]([CH2:21][N:22]3[CH2:27][CH2:26][CH:25]([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)[CH2:24][CH2:23]3)[CH2:13]2)=[O:11])[CH:3]=[CH:2]1.[CH2:35]1OCCOCCOCCOCCOCCOC1.CC([O-])(C)C.[K+].CI>CCOCC>[CH3:35]... | O=C(c1cccc2cc[nH]c12)N1CC(CN2CCC(c3ccc(F)cc3)CC2)C(C(F)(F)F)C1 | C1COCCOCCOCCOCCOCCO1 | null | CC(C)(C)[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CI | CCOCC | null | null | null | null | null | null | null | null | null | null | 0.08 | To a solution of 0.033 g (0.07 mmol) of 1-(7-indolecarbonyl)-3-(RS)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(SR)-(trifluoromethyl)pyrrolidine and 0.022 g (0.084 mmol) of 18-Crown-6 ether in 2 mL of ether at rt was added 0.084 mL of KOt-Bu (1M in t-BuOH). After stirring for 5 min, 0.006 mL (0.098 mmol) of MeI was added ... | Cn1ccc2cccc(C(=O)N3CC(CN4CCC(c5ccc(F)cc5)CC4)C(C(F)(F)F)C3)c21 | null | null | null |
754,479 | ord_dataset-1b0cd79134f0450eaac8396a4f956c30 | null | 2007-01-01T00:02:00 | true | [NH2:1][C:2]([C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[N:23]([CH3:27])[C:22](=[O:28])[CH:21]=[C:20]2[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[CH:30]=1)([C:11]1[N:15]([CH3:16])[CH:14]=[N:13][CH:12]=1)[C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1>[Ni].CO.N>[NH2:1][C:2]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N... | Cn1cncc1C(N)(c1ccc(C#N)cc1)c1ccc2c(c1)c(-c1cccc(Cl)c1)cc(=O)n2C | null | null | [Ni] | N | 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 | 8 | Raney nickel (0.55 g) was added to a mixture of 4-[amino[4-(3-chlorophenyl)-1,2-dihydro-1-methyl-2-oxo-6-quinolinyl](1-methyl-1H-imidazol-5-yl)methyl]-benzonitrile, (0.0011 mol) in CH3OH/NH3 7N (12 ml) under N2 flow. The mixture was hydrogenated overnight under a 5 bar pressure, then filtered over celite. The filtrate ... | Cn1cncc1C(N)(c1ccc(CN)cc1)c1ccc2c(c1)c(-c1cccc(Cl)c1)cc(=O)n2C | null | null | null |
506,671 | ord_dataset-631d58dab387485c8eb0db4c20a232b7 | null | 2001-01-01T00:06:00 | true | [CH:1]([C@@H:3]1[C@@H:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)[CH2:6][N:5]([C@H:15]([CH2:26][CH:27]2[CH2:30][CH2:29][CH2:28]2)[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH2:4]1)=O.[NH:31]1[CH2:36][CH2:35][CH:34]([N:37]2[C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=3[N:39]=... | O=C[C@H]1CN([C@H](CC2CCC2)C(=O)OCc2ccccc2)C[C@@H]1c1cccc(F)c1 | c1ccc2c(c1)ncn2C1CCNCC1 | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from 22 mg of α-(R)-(3-(R)-formyl-4-(S)-(3-fluorophenyl)pyrrolidin-1-yl)-3-cyclobutylpropionic acid, benzyl ester (prepared above as Aldehyde 2), 27 mg of 1-piperidin-4-yl-1-H-benzoimidazole (from Example 95, Step C) and 40 mg of sodium triacetoxyborohydride in 4 mL of THF and 1 mL of DM... | O=C(OCc1ccccc1)[C@@H](CC1CCC1)N1C[C@H](CN2CCC(n3cnc4ccccc43)CC2)[C@@H](c2cccc(F)c2)C1 | null | 72 | null |
299,779 | ord_dataset-fb70ed83140e4f53a907d87192ad748c | null | 1994-01-01T00:11:00 | true | [C:1]([NH:4][CH2:5][C:6]1[N:11]=[C:10]([C:12]2[N:13]=[C:14]([N:17]=[C:18]([NH2:20])[NH2:19])[S:15][CH:16]=2)[CH:9]=[C:8](Cl)[CH:7]=1)(=[O:3])[CH3:2].[H][H]>[Pd].CO>[C:1]([NH:4][CH2:5][C:6]1[N:11]=[C:10]([C:12]2[N:13]=[C:14]([N:17]=[C:18]([NH2:19])[NH2:20])[S:15][CH:16]=2)[CH:9]=[CH:8][CH:7]=1)(=[O:3])[CH3:2] | [H][H] | CC(=O)NCc1cc(Cl)cc(-c2csc(N=C(N)N)n2)n1 | 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 | 4-(6-Acetylaminomethyl-4-chloropyridin-2-yl)-2-(diaminomethyleneamino)thiazole (160 mg) was hydrogenated over 10% palladium on carbon (50% wt) (50 mg) in methanol (5 ml) at atmospheric pressure of hydrogen for 8 hours at ambient temperature. After the catalyst was removed by filtration, the solvent was evaporated in va... | CC(=O)NCc1cccc(-c2csc(N=C(N)N)n2)n1 | null | 90.9 | null |
309,305 | ord_dataset-081613ef79bd4110aacc146b4465f086 | null | 1995-01-01T00:05:00 | true | [N-:1]=[C:2]=[S:3].[C:4]([O:8][CH2:9][CH3:10])(=[O:7])[NH:5][NH2:6]>>[C:4]([NH:5][NH:6][C:2]([NH2:1])=[S:3])([O:8][CH2:9][CH3:10])=[O:7] | [N-]=C=S | CCOC(=O)NN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | For the synthesis of compounds of formula (I) wherein E=--S--, Reaction Schemes 13 and 14 may be utilized. In Reaction Scheme 13, the isothiocyanate 22 is reacted with ethyl carbazate (8) to give the 1-(carbethoxy)thiosemicarbazide 48. By standard conditions, 48 is S-alkylated to yield 49, which can be cyclized to the ... | CCOC(=O)NNC(N)=S | null | null | null |
1,160,002 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | C[O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([S:10]([CH2:13][CH:14]2[CH2:16][CH2:15]2)(=[O:12])=[O:11])[CH2:7][N:6]1[C:17]1[N:18]([C:23]2[CH:28]=[CH:27][N:26]=[C:25]([Cl:29])[CH:24]=2)[N:19]=[C:20]([CH3:22])[CH:21]=1)=[O:4].[OH-].[Li+]>>[Cl:29][C:25]1[CH:24]=[C:23]([N:18]2[C:17]([N:6]3[CH2:7][C@H:8]([S:10]([CH2:13][CH:14]4[CH2... | COC(=O)[C@@H]1C[C@@H](S(=O)(=O)CC2CC2)CN1c1cc(C)nn1-c1ccnc(Cl)c1 | null | null | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | In analogy to the procedure described in example 253e, (2S,4R)-1-[2-(2-chloro-pyridin-4-yl)-5-methyl-2H-pyrazol-3-yl]-4-cyclopropylmethanesulfonyl-pyrrolidine-2-carboxylic acid methyl ester was saponified in the presence of lithium hydroxide to give the title compound as off-white solid which was used in the next step ... | Cc1cc(N2C[C@H](S(=O)(=O)CC3CC3)C[C@H]2C(=O)O)n(-c2ccnc(Cl)c2)n1 | null | null | null |
715,407 | ord_dataset-c8a367b56b4f406b878f51867b157d19 | null | 2006-01-01T00:06:00 | true | C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:35])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH2:25][CH2:26][C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:28]=3[Cl:34])[CH:17]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C1(C)C=CC=CC=1>Cl.C(O)C>[Cl:34][C:28]1[CH:29]=[C:30]([Cl:33])[CH:31]=[CH:32][C:27]=1[CH2:2... | COc1ccc(C(=O)NC2CCN(C(=O)OC(C)(C)C)CC2)cc1OCCc1ccc(Cl)cc1Cl | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | 1.4 g 4-{3-[2-(2,4-Dichloro-phenyl)-ethoxy]-4-methoxy-benzoylamino}-piperidine-1-carboxylic acid tert-butyl ester was suspended in 20 ml HCl in ethanol at RT. After 2 h a clear solution was obtained. Addition of 50 ml toluene followed by evaporation of the solvent and repeatedly coevaporation of the residue with toluen... | COc1ccc(C(=O)NC2CCNCC2)cc1OCCc1ccc(Cl)cc1Cl | null | null | null |
1,460,552 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [C:1]1([C:7]2[C:12]([C:13]([F:16])([F:15])[F:14])=[N:11][NH:10][C:9](=O)[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)([Cl:20])=O.C(=O)([O-])O.[Na+].ClCCl>C(#N)C>[Cl:20][C:9]1[N:10]=[N:11][C:12]([C:13]([F:16])([F:15])[F:14])=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:8]=1 | O=P(Cl)(Cl)Cl | O=c1cc(-c2ccccc2)c(C(F)(F)F)n[nH]1 | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | ClCCl | null | null | null | null | null | null | null | null | null | null | null | To a stirred solution of 5-phenyl-6-trifluoromethyl-2H-pyridazine-3-one (D2) (20.66 g, 0.086 mol) in acetonitrile (150 ml) was added phosphorous oxychloride (20 ml, 0.215 mmol) and the reaction heated at reflux for 1 h. After this period, the reaction mixture was poured into a saturated solution of sodium hydrogen carb... | FC(F)(F)c1nnc(Cl)cc1-c1ccccc1 | null | 12,768.7 | null |
1,552,802 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[OH:12].[N:13]1[CH:18]=[CH:17][N:16]=[C:15]([N:19]2[CH2:23][CH2:22][CH:21](O)[CH2:20]2)[N:14]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:10])([F:11])[F:9])=[CH:4][C:3]=1[O:12][CH:21]1[CH2:22][CH2:23][N:19](... | OC1CCN(c2nccnn2)C1 | Oc1cc(C(F)(F)F)ccc1Cl | null | CC(C)OC(=O)/N=N/C(=O)OC(C)C | 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 | null | Compound 42 is prepared from 2-chloro-5-trifluoromethylphenol and intermediate 5d according to synthesis method 3 in toluene in the presence of DIAD, under the operating conditions described for example 8 (86% yield). | FC(F)(F)c1ccc(Cl)c(OC2CCN(c3nccnn3)C2)c1 | null | null | null |
1,715,204 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | [N:1]([C@@H:4]([C@@H:8]([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)[CH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)[C:5]([OH:7])=O)=[N+]=[N-].[NH2:22][C:23]1[CH:24]=[N:25][CH:26]=[C:27]([F:54])[C:28]=1[CH2:29][CH2:30][C@H:31]1[O:36][CH2:35][C@H:34]([CH2:37][O:38][C:39]([NH:41][CH2:42][C:43]([F:46])([F:45])[F:... | [N-]=[N+]=N[C@H](C(=O)O)[C@@H](c1ccc(F)cc1)C1CCOCC1 | CC(C)(C)OC(=O)N1C[C@@H](CCc2c(N)cncc2F)OC[C@@H]1COC(=O)NCC(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 | The title compound was prepared from the product of step 1 and the product of step 4 of Example 89 using the procedures given in steps 2-4 of Example 93. MS (ES) m/z=630 (M+H)+. | N[C@H](C(=O)Nc1cncc(F)c1CC[C@@H]1CN[C@H](COC(=O)NCC(F)(F)F)CO1)[C@@H](c1ccc(F)cc1)C1CCOCC1 | null | null | null |
610,402 | ord_dataset-73916d628db147c89020b3baac642d48 | null | 2003-01-01T00:09:00 | true | [S:1]1[C:5]2[C:6]3[CH:11]=[CH:10][S:9][C:7]=3[S:8][C:4]=2[CH:3]=[C:2]1[C:12]([OH:14])=O.[Al+3].[Cl-].[Cl-].[Cl-].[C:19](Cl)(=O)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]C.Cl>ClCCl>[C:12]([C:2]1[S:1][C:5]2[C:6]3[CH:11]=[CH:10][S:9][C:7]=3[S:8][C:4]=2[CH:3]=1)(=[O:14])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24... | O=C(O)c1cc2sc3sccc3c2s1 | CCCCCCCC(=O)Cl | null | Cl | [Al+3] | [Cl-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | null | Dithienothiophene 2 (R1═R2═R3═R4═H) (765 mg, 3.90 mmol) was dissolved in dry dichloromethane (35 cm3) and the solution was ice-cooled before AlCl3 (790 mg, 5.92 mmol) was added in one portion yielding a dark mixture. A solution of octanoyl chloride (1.00 g, 6.02 mmol) in dichloromethane (20 cm3) was added dropwise over... | CCCCCCCC(=O)c1cc2sc3sccc3c2s1 | null | 62.8 | null |
1,269,735 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | [CH3:1][O:2][C:3]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][C:8]=2[CH:9]=1)=[O:4].C([O-])([O-])=O.[Cs+].[Cs+].Cl[C:22]1[S:23][C:24]2[C:25]([N:30]=1)=[N:26][CH:27]=[CH:28][CH:29]=2.O>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][C:11]([O:14][C:22]3[S:23][C:24]4[C:25]([N:30]=3)=[N:26][CH:27]=[... | Clc1nc2ncccc2s1 | COC(=O)c1cc2cc(O)ccc2o1 | 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 | O | null | null | null | null | null | null | null | null | null | 50 | null | To a solution of 5-hydroxy-benzofuran-2-carboxylic acid methyl ester (1.5 g, 7.8 mmol) in DMF (78 mL) was added Cs2CO3 (7.6 g, 26 mmol) and 2-chloro-thiazolo[4,5-b]pyridine (1.6 g, 7.8 mmol). The reaction mixture was heated (50° C., 10 h), cooled (rt) and water was added (50 mL). The resulting solid was filtered to pro... | COC(=O)c1cc2cc(Oc3nc4ncccc4s3)ccc2o1 | null | 102.1 | null |
1,006,227 | ord_dataset-7448b89163bf426c9d9777809ce24cec | null | 2010-01-01T00:11:00 | true | Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([CH:10]([CH3:12])[CH3:11])[C:3]=1[CH3:13].[Li]CCCC.[CH3:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=[O:26])=[C:23]([CH3:29])[CH:22]=1>C1COCC1>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([CH:25]([C:24]2[CH:27]=[CH:28][C:21]([O:20][CH3:19])=[CH:22][C:23]=2[CH3:29])[OH:26])=[C:3](... | COc1ccc(Br)c(C)c1C(C)C | COc1ccc(C=O)c(C)c1 | null | [Li]CCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | -78 | 1 | To a stirring solution of 1-bromo-3-iso-propyl-4-methoxy-2-methyl-benzene (compound 7-16, step c; 0.7 g, 2.88 mmol) in THF (20 mL) at −78° C. was added n-BuLi (1.6 mL, 2.5 M in hexanes). The mixture was stirred at −78° C. for 1 hr and 4-methoxy-2-methyl-benzaldehyde (0.37 mL, 2.74 mmol) was added. The reaction mixture ... | COc1ccc(C(O)c2ccc(OC)c(C(C)C)c2C)c(C)c1 | null | 116.1 | null |
46,475 | ord_dataset-becaf7dc22c44672b22e4b94335cbf08 | null | 1978-01-01T00:09:00 | true | [N+:1]([C:4]1[CH:17]=[CH:16][C:7]2[CH2:8][CH2:9][CH:10]([CH2:14][NH2:15])[CH2:11][CH:12](O)[C:6]=2[CH:5]=1)([O-:3])=[O:2].S(=O)(=O)(O)O>O1CCOCC1>[N+:1]([C:4]1[CH:17]=[CH:16][C:7]2[CH2:8][CH2:9][CH:10]([CH2:14][NH2:15])[CH:11]=[CH:12][C:6]=2[CH:5]=1)([O-:3])=[O:2] | NCC1CCc2ccc([N+](=O)[O-])cc2C(O)C1 | null | null | O=S(=O)(O)O | 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 | 0.05 | A mixture of 10 g of the product of Step D in 100 ml of dioxane under nitrogen was heated to reflux and 20 ml of concentrated sulfuric acid were added thereto dropwise over 3 minutes. The mixture was stirred at reflux for 20 minutes and was then concentrated to 50 ml under reduced pressure. 300 ml of water were added a... | NCC1C=Cc2cc([N+](=O)[O-])ccc2CC1 | null | 108.3 | null |
1,417,224 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:25])=[C:14]([C:20](OCC)=[O:21])[C:15](=[O:19])[NH:16]3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[CH3:26][C@@H:27]([OH:30])[CH2:28][NH2:29]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:25])=[C:14]([C:20]([NH:29][CH2:28][C... | C[C@@H](O)CN | CCOC(=O)c1c(O)c2ncc(Cc3ccc(F)cc3)cc2[nH]c1=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 | This compound was prepared from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and R-(−)-1-amino-2-propanol employing methods similar to those described in Example 2 and was obtained as a white solid: 1H NMR (d6-DMSO) tautomers are observed δ 11.81 (1H, t, J=5.7), 10.81 (1H... | C[C@@H](O)CNC(=O)c1c(O)c2ncc(Cc3ccc(F)cc3)cc2[nH]c1=O | null | null | null |
1,236,466 | ord_dataset-e96f5a2842f14e5380461c234100f05a | null | 2012-01-01T00:12:00 | true | I[C:2]1[N:3]=[C:4]([CH3:16])[N:5]([C:8]2[CH:13]=[N:12][N:11]([CH3:14])[C:10](=[O:15])[CH:9]=2)[C:6]=1[CH3:7].[C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[CH:20]=1)#[CH:18]>>[CH3:16][C:4]1[N:5]([C:8]2[CH:13]=[N:12][N:11]([CH3:14])[C:10](=[O:15])[CH:9]=2)[C:6]([CH3:7])=[C:2]([C:18]#[C:17][C:19]2[CH:20]=[C:21]([C... | C#Cc1cccc(C)c1 | Cc1nc(I)c(C)n1-c1cnn(C)c(=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, light yellow cristalline solid, MS: m/e=319.1 (M+H+), was prepared in accordance with the general method of example 1c from 5-(4-iodo-2,5-dimethyl-imidazol-1-yl)-2-methyl-2H-pyridazin-3-one and 1-ethynyl-3-methyl-benzene. | Cc1cccc(C#Cc2nc(C)n(-c3cnn(C)c(=O)c3)c2C)c1 | null | null | null |
1,557,126 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | [Br:1]N1C(=O)CCC1=O.[C:9]([C:13]1[S:17][C:16]([C:18]([O:20][CH3:21])=[O:19])=[C:15]([CH3:22])[CH:14]=1)([CH3:12])([CH3:11])[CH3:10].CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:1][CH2:22][C:15]1[CH:14]=[C:13]([C:9]([CH3:12])([CH3:11])[CH3:10])[S:17][C:16]=1[C:18]([O:20][CH3:21])=[O:19] | COC(=O)c1sc(C(C)(C)C)cc1C | O=C1CCC(=O)N1Br | null | CC(C)(C#N)N=NC(C)(C)C#N | 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 | N-bromosuccinimide (18.5 g, 0.103 mol) was added to a solution of methyl 5-tert-butyl-3-methylthiophene-2-carboxylate (109b) (20 g, 0.09 mol) and AIBN (0.774 g, 0.0047 mol) in CCl4 (200 mL). The mixture was refluxed for 2 h, cooled to room temperature and filtered. The filtrate was concentrated under vacuum and the obt... | COC(=O)c1sc(C(C)(C)C)cc1CBr | null | 42 | null |
1,619,453 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | [N+:1]([O-:4])(O)=[O:2].S(=O)(=O)(O)O.[Cl:10][C:11]1[C:20]2[C:15](=[CH:16][C:17]([Cl:21])=[CH:18][CH:19]=2)[N:14]=[CH:13][CH:12]=1>>[Cl:10][C:11]1[C:20]2[C:15](=[C:16]([N+:1]([O-:4])=[O:2])[C:17]([Cl:21])=[CH:18][CH:19]=2)[N:14]=[CH:13][CH:12]=1 | Clc1ccc2c(Cl)ccnc2c1 | O=[N+]([O-])O | 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 | 25 | 18 | Fuming nitric acid (8 ml) and concentrated sulfuric acid (16 ml) were combined cautiously at −10° C. 4,7-dichloroquinoline (5 g, 25 mmol) was added portionwise at −10° C. and after complete addition the mixture was allowed to warm to room temperature and stirring continued for 18 h. The reaction mixture was poured onto... | O=[N+]([O-])c1c(Cl)ccc2c(Cl)ccnc12 | null | 94 | null |
1,686,357 | ord_dataset-c1e70ad912eb438f8d34b1dc681f809a | null | 2016-01-01T00:02:00 | true | Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[C:5]([F:11])[CH:4]=1.[CH3:12][O:13][C:14]1[CH:34]=[CH:33][C:17]([CH2:18][NH:19][S:20]([C:23]2[CH:32]=[CH:31][C:26]([C:27]([O:29]C)=[O:28])=[CH:25][CH:24]=2)(=[O:22])=[O:21])=[CH:16][CH:15]=1>>[F:11][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][C:6]=1[O:9][CH3:10])[CH2:2][N:19]([CH2:... | COC(=O)c1ccc(S(=O)(=O)NCc2ccc(OC)cc2)cc1 | COc1ccc(CBr)cc1F | null | null | null | null | null | null | null | 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 as in example 5-10 from 4-(bromomethyl)-2-fluoro-1-methoxybenzene and methyl 4-(N-(4-methoxybenzyl)sulfamoyl)benzoate (example 5-10b). MS (M−H, 458.10); NMR (400 MHz, CD3OD): δ, ppm: 3.73 (s, 3H), 3.80 (s, 3H), 4.24 (s, 2H), 4.28 (s, 2H), 6.75 (m, 4H), 6.88 (m, 1H), 6.97 (d, 2H, J=8.6 Hz), 7.88 (d, 2H, J=8.3 H... | COc1ccc(CN(Cc2ccc(OC)c(F)c2)S(=O)(=O)c2ccc(C(=O)O)cc2)cc1 | null | null | null |
1,276,804 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH:11]([C:13]3[CH:14]=[C:15]4[C:19](=[CH:20][C:21]=3[F:22])[N:18]([CH3:23])[N:17]=[CH:16]4)[CH3:12])=[CH:9][N:10]=2)[N:7]=1.C([Sn](CCCC)(CCCC)[C:29]([O:31][CH2:32][CH3:33])=[CH2:30])CCC>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=... | CC(c1cc2cnn(C)c2cc1F)c1cnc2ccc(Cl)nn12 | C=C(OCC)[Sn](CCCC)(CCCC)CCCC | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 100 | 0.33 | To a solution of 6-chloro-3-(1-(6-fluoro-1-methyl-1H-indazol-5-yl)ethyl)imidazo[1,2-b]pyridazine (900 mg, 1.910 mmol) in DMF (8 mL) was added Pd(Ph3P)4 (221 mg, 0.191 mmol). The mixture was stirred for 20 min, and tributyl(1-ethoxyvinyl)stannane (784 mg, 2.102 mmol) was added. The resulting mixture was heated at 100° C... | C=C(OCC)c1ccc2ncc(C(C)c3cc4cnn(C)c4cc3F)n2n1 | null | 64.5 | null |
496,289 | ord_dataset-9df8b3ec9c8742b3802e0efaac6f6ef3 | null | 2001-01-01T00:03:00 | true | [CH2:1]([N:5]1[C:13]2[C:8](=[C:9]([F:14])[CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6]1)[CH:2]1[O:4][CH2:3]1.[NH:15]1[CH:20]=[CH:19][CH:18]([C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[NH:23][CH:22]=2)[CH2:17][CH2:16]1>>[F:14][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:8]=1[CH:7]=[CH:6][N:5]2[CH2:1][CH:2]([OH:4])[CH2:3][... | Fc1cccc2c1ccn2CC1CO1 | C1=CC(c2c[nH]c3ccccc23)CCN1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | A methanolic solution of 1-N-glycidyl-4-fluoroindole (0.52 g, 3.0 mmole) from example 3 and 3-(4-tetrahydropyridinyl)indole (0.59 g, 3.0 mmole) was refluxed under nitrogen for 15 hours. The reaction mixture was concentrated in vacuo and the product purified by flash silica gel chromatography (ethyl acetate) to afford t... | OC(CN1CC=C(c2c[nH]c3ccccc23)CC1)Cn1ccc2c(F)cccc21 | null | 52.2 | null |
809,160 | ord_dataset-da49b0378abf41bf92ab8ecdd3feb28b | null | 2008-01-01T00:02:00 | true | [CH2:1]([O:13][C:14]1[CH:15]=[C:16]([CH:21]=[C:22]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH:23]=1)[CH2:17][N:18]=[N+]=[N-])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].CO.[H][H]>CCOCC>[CH2:25]([O:24][C:22]1[CH:21]=[C:1... | [H][H] | CCCCCCCCCCCCOc1cc(CN=[N+]=[N-])cc(OCCCCCCCCCCCC)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | CCOCC | null | null | null | null | null | null | null | null | null | null | null | A thick walled bottle containing a stir bar was flushed out with nitrogen gas, and 5% Palladium on activated carbon (0.53 g, 10% by mass) was added along with a solution of 50% methanol and ether (approximately 10 mL). 3,5-didodecoxybenzyl azide (5.3 g, 12.6 mmol) was added using 50% methanol and ether (approximately 4... | CCCCCCCCCCCCOc1cc(CN)cc(OCCCCCCCCCCCC)c1 | null | 88 | null |
1,166,964 | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | null | 2012-01-01T00:05:00 | true | Cl.[Br:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][NH2:7].C([O-])([O-])=O.[Na+].[Na+].[CH:17]1[C:29]2[CH:28]([CH2:30][O:31][C:32](C3CC(=O)N(O)C3=O)=[O:33])[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]=2[CH:20]=[CH:19][CH:18]=1>O1CCOCC1.C(Cl)Cl>[CH:17]1[C:29]2[CH:28]([CH2:30][O:31][C:32](=[O:33])[NH:7][C... | NCc1cccc(Br)c1 | O=C(OCC1c2ccccc2-c2ccccc21)C1CC(=O)N(O)C1=O | null | Cl | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | ClCCl | null | null | null | null | null | null | null | null | null | null | 0.5 | To 3-bromobenzylamine hydrochloride (16.0 g, 71.9 mmol) was added aqueous 9% Na2CO3 (211 mL) followed by 9-fluorenylmethyloxycarbonyl-N-hydroxysuccinimide (25.5 g, 75.5 mmol) in dioxane (211 mL). This was stirred 30 minutes, then diluted with CH2Cl2 (200 mL). The layers were separated and the aqueous layer was extracte... | O=C(NCc1cccc(Br)c1)OCC1c2ccccc2-c2ccccc21 | null | 82.1 | null |
716,501 | ord_dataset-c8a367b56b4f406b878f51867b157d19 | null | 2006-01-01T00:06:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([C:8](=O)[CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][CH:16]([C:19]3[CH:20]=[C:21]([NH:25][C:26](=[O:30])[CH:27]([CH3:29])[CH3:28])[CH:22]=[CH:23][CH:24]=3)[CH2:15][CH2:14]2)[CH:5]=[CH:6][CH:7]=1.Cl.[CH3:33][C:34]1[CH:39]=[CH:38][C:37]([NH:40]N)=[CH:36][CH:35]=1>>[Cl:1][C:2]1[CH:3]=[C... | CC(C)C(=O)Nc1cccc(C2CCN(CCCCC(=O)c3cccc(Cl)c3)CC2)c1 | Cc1ccc(NN)cc1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared by Procedure E and Scheme M using N-(3-{1-[5-(3-chlorophenyl)-5-oxopentyl]-4-piperidinyl}phenyl)-2-methylpropanamide and 4-methylphenylhydrazine hydrochloride: ESMS m/e: 528.2 (M+H)+. | Cc1ccc2[nH]c(-c3cccc(Cl)c3)c(CCCN3CCC(c4cccc(NC(=O)C(C)C)c4)CC3)c2c1 | null | null | null |
977,035 | ord_dataset-f886e51ba1484c76a94bce1482f1eab9 | null | 2010-01-01T00:07:00 | true | [CH:1]1([NH:7][C:8]2[CH:13]=[CH:12][C:11]([S:14]([NH2:17])(=[O:16])=[O:15])=[CH:10][C:9]=2[N+:18]([O-:20])=[O:19])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:21]N1C(C)(C)C(=O)N(Br)C1=O.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>ClCCl>[Br:21][C:13]1[CH:12]=[C:11]([S:14]([NH2:17])(=[O:16])=[O:15])[CH:10]=[C:9]([N+:18]([O-:20])=[O:19... | NS(=O)(=O)c1ccc(NC2CCCCC2)c([N+](=O)[O-])c1 | CC1(C)C(=O)N(Br)C(=O)N1Br | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | null | 18 | A room temperature solution of Example 3A (1.81 g, 6.0 mmol) and 1,3-dibromo-5,5-dimethylhydantoin (950 mg, 3.3 mmol) in dichloromethane was treated with trifluoracetic acid (796 uL, 9.0 mmol), stirred in darkness for 18 hours, treated with saturated NaHCO3, and extracted with diethyl ether. The combined extracts were ... | NS(=O)(=O)c1cc(Br)c(NC2CCCCC2)c([N+](=O)[O-])c1 | null | null | null |
1,593,913 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | OO.F[C:4](F)(F)[C:5]([O:7][C:8](=O)[C:9](F)(F)F)=O.[CH2:16]([N:23]1CC=C(C)[CH2:25][CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[O-]S([O-])=O.[Na+].[Na+]>C(Cl)Cl>[CH2:16]([N:23]1[CH2:24][CH2:25][C:8]2([CH3:9])[CH:5]([O:7]2)[CH2:4]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1 | CC1=CCN(Cc2ccccc2)CC1 | O=C(OC(=O)C(F)(F)F)C(F)(F)F | null | O=S([O-])[O-] | OO | [Na+] | 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 | 12 | To a mixture of a 30% hydrogen peroxide solution (3.6 mL) and DCM (120 mL) were added trifluoroacetic anhydride (6.0 mL) at 0° C., and a solution of 1-benzyl-4-methyl-1,2,3,6-tetrahydropyridine (2.9 g) in DCM (10 mL) was further added thereto, followed by stirring at room temperature for 12 hours and then stirring at 5... | CC12CCN(Cc3ccccc3)CC1O2 | null | null | null |
1,178,934 | ord_dataset-0f9d2dbe929a45c3892ae75e81e99443 | null | 2012-01-01T00:06:00 | true | [N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C:11]([F:14])([F:13])[F:12])[C:5]=1[NH2:15])([O-])=O>CCO>[F:12][C:11]([F:13])([F:14])[O:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([NH2:1])[C:5]=1[NH2:15] | Nc1c(OC(F)(F)F)cccc1[N+](=O)[O-] | null | 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 | 5 | 3-Trifluoromethoxy-benzene-1,2-diamine was synthesized by dissolving 0.79 g of 2-nitro-6-trifluoromethoxy-phenylamine (J. Med. Chem. 1999, 42, 15, 2828-2843) in 20 mL EtOH, evacuating 3 times with N2 and adding 80 mg of 10 wt % Pd/C. The reaction mixture was stirred under a H2 atmosphere (balloon) for 5 h. Filtration o... | Nc1cccc(OC(F)(F)F)c1N | null | null | null |
219,629 | ord_dataset-6cb04513a4a244c0b612b566096f4b3d | null | 1990-01-01T00:12:00 | true | [CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[C:9](/[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:10]/[CH:11]=O)=[CH:5][CH:4]=1.[C:19]([CH:23]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:21][CH3:22])=[O:20]>C(Cl)(Cl)(Cl)Cl.ClCCl>[CH3:22][O:21][C:19](=[O:20])/[CH:23]=[CH:11]/[CH:10]=[C:9](/[C:6]1[CH:7]=[CH:8][C:3]([O:2][C... | COC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1 | COc1ccc(/C(=C/C=O)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)(Cl)Cl | ClCCl | null | null | null | null | null | null | null | null | null | null | null | As described in Example 99, (E)-3-(4-methoxyphenyl)-3-phenyl-2-propenal (8.7 g) was reacted with (carbomethoxymethylene)triphenylphosphorane (14.2 g) in carbon tetrachloride (50 mL) and dichloromethane (5 mL) overnight at room temperature. The crude ester was isolated in the usual manner and was purified by HPLC (ether... | COC(=O)/C=C/C=C(\c1ccccc1)c1ccc(OC)cc1 | null | 80 | null |
189,984 | ord_dataset-be83cbc722064f3696975001242f9f1a | null | 1989-01-01T00:05:00 | true | [Br-:1].[NH2:2][N+:3]1[CH:7]=[CH:6][N:5]([CH2:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[C:4]=1[CH2:15][CH3:16].[CH3:17][N:18]([CH3:27])[C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1>C(O)(=O)C>[Br-:1].[CH3:17][N:18]([CH3:27])[C:19]1[CH:26]=[CH:25][C:22]([CH:23]=[N:2][N+:3]2[CH:7]=[CH:6][N:5]([CH2:8][... | CCc1n(CC(=O)C(C)(C)C)cc[n+]1N | CN(C)c1ccc(C=O)cc1 | null | [Br-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | 25 | 48 | 2.38 g (8.2 mmol) of 1-amino-2-ethyl-3-(3,3-dimethyl-2-oxobutyl)imidazolium bromide are dissolved in 30 ml of glacial acetic acid, whereupon the solution is treated with 1.22 g (8.2 mmol) of p-dimethylaminobenzaldehyde. After stirring at room temperature 48 hours the product is recrystallized by the addition of ether, ... | CCc1n(CC(=O)C(C)(C)C)cc[n+]1N=Cc1ccc(N(C)C)cc1 | null | null | null |
1,587,197 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | [C:1]([C:4]1[C:5]([F:21])=[C:6]([F:20])[C:7]([N:12]2[CH2:17][C@H:16]([CH3:18])[O:15][C@H:14]([CH3:19])[CH2:13]2)=[C:8]([CH:11]=1)[CH:9]=O)(=[O:3])[CH3:2].[NH:22]1[C:29](=[O:30])[CH2:28][C:26](=[O:27])[NH:25][C:23]1=[O:24]>CC(O)C>[C:1]([C:4]1[CH:11]=[C:8]2[C:7](=[C:6]([F:20])[C:5]=1[F:21])[N:12]1[CH2:17][C@@H:16]([CH3:1... | CC(=O)c1cc(C=O)c(N2C[C@@H](C)O[C@@H](C)C2)c(F)c1F | O=C1CC(=O)NC(=O)N1 | null | null | 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 | 85 | null | To a solution of 5-acetyl-2-((2R,6S)-2,6-dimethyl-morpholin-4-yl)-3,4-difluoro-benzaldehyde (Intermediate 11, 3.0 g, 9.17 mmol) in IPA was added barbituric acid (1.4 g, 11.00 mmol), and the mixture was heated at 85° C. for 12 hours. Solvents were evaporated and the residue was purified over neutral alumina using a grad... | CC(=O)c1cc2c(c(F)c1F)N1C[C@@H](C)O[C@@H](C)[C@@H]1C1(C2)C(=O)NC(=O)NC1=O | null | null | null |
1,565,743 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | [CH:1]1([C:5]2[N:6]=[C:7]([C:10]([O-:12])=O)[S:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[Li+].C(C1N=C(C([Cl:24])=O)SC=1)(C)C>>[CH:1]1([C:5]2[N:6]=[C:7]([C:10]([Cl:24])=[O:12])[S:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1 | CC(C)c1csc(C(=O)Cl)n1 | O=C([O-])c1nc(C2CCC2)cs1 | null | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 4-Cyclobutylthiazole-2-carbonyl chloride 267b was synthesized from compound 266b (5 g, 1 eq.), following the procedure as described for compound 214. MS (ESI, EI+): m/z=198 (MH+). | O=C(Cl)c1nc(C2CCC2)cs1 | null | null | null |
1,758,764 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | Br[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:13]=[C:12]([CH:14]3[CH2:16][CH2:15]3)[NH:11][N:10]=2)[CH:5]=[CH:4][N:3]=1.[S:17]1[CH:21]=[CH:20][CH:19]=[C:18]1B(O)O.C([O-])([O-])=O.[Na+].[Na+].O1CCOCC1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2... | OB(O)c1cccs1 | Brc1nccc(Nc2cc(C3CC3)[nH]n2)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 | O | C1COCCO1 | null | null | null | null | null | null | null | null | null | 100 | 15 | A mixture of 2-bromo-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amine (170 mg, 0.64 mmol, 1.0 equiv.), thiophen-2-ylboronic acid (107 mg, 0.83 mmol, 1.3 equiv.), Pd(PPh3)4 (148 mg, 0.128 mmol, 0.2 equiv.), Na2CO3 (238 mg, 2 mmol, 3.5 equiv.), 1,4-dioxane (5 ml) and water (1 ml) was stirred at 100° C. under a nitrogen... | c1csc(-c2nccc(Nc3cc(C4CC4)[nH]n3)n2)c1 | null | 50.8 | null |
1,349,014 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | [NH2:1][C:2]1[C:21]([O:22][CH3:23])=[CH:20][C:5]2[CH2:6][CH2:7][N:8]([CH2:11][C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)=[O:13])[CH2:9][CH2:10][C:4]=2[CH:3]=1.[Cl:24][C:25]1[CH:26]=[CH:27][C:28]([NH:37][C:38]2[C:43]([Cl:44])=[CH:42][N:41]=[C:40](Cl)[N:39]=2)=[C:29]([S:31]([N:34]([CH3:36])[CH3:35])(=[O:33])=[... | CN(C)S(=O)(=O)c1cc(Cl)ccc1Nc1nc(Cl)ncc1Cl | COc1cc2c(cc1N)CCN(CC(=O)N1CCOCC1)CC2 | null | null | null | null | null | null | null | 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-(7-Amino-8-methoxy-1,2,4,5-tetrahydro-3-benzazepin-3-yl)-1-morpholin-4-yl-ethanone and 5-Chloro-2-(2,5-dichloro-pyrimidin-4-ylamino)-N,N-dimethyl-benzenesulfonamide in an analogous manner to Example 61e. Product isolated as a tan foam (0.034 g, 24%). MP: 100-115° C. 1HNMR (400 MHz... | COc1cc2c(cc1Nc1ncc(Cl)c(Nc3ccc(Cl)cc3S(=O)(=O)N(C)C)n1)CCN(CC(=O)N1CCOCC1)CC2 | null | null | null |
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