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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
1,322,151 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | Br[C:2]1[C:3]([CH3:17])=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH:14]([CH3:16])[CH3:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.[C:18]([NH:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1)(=[O:20])[CH3:19]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P... | Cc1cc(N2CCN(C(C)C)CC2)ncc1Br | CC(=O)Nc1cccc(B(O)O)c1 | 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 | C1COCCO1 | O | null | null | null | null | null | null | null | null | null | 100 | null | To a solution of 1-(5-bromo-4-methyl-pyridin-2-yl)-4-isopropyl-piperazine (0.59 g, 2 mmol) in 1,4-dioxane (12 mL) and water (3 mL) was added 3-acetylamino-phenylboronic acid (430 mg, 2.4 mmol), Pd(PPh3)4 (231 mg, 0.2 mmol) and TEA (404 mg, 4 mmol). The resulting mixture was degassed and heated at 100° C. for 4 h under ... | CC(=O)Nc1cccc(-c2cnc(N3CCN(C(C)C)CC3)cc2C)c1 | null | null | null |
836,419 | ord_dataset-ec576c604a9d47258c87c732a043ec71 | null | 2008-01-01T00:08:00 | true | [NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[CH:10]=O.[CH3:12][N:13]1[CH2:17][CH2:16][CH2:15][CH:14]1[CH2:18][CH2:19][NH2:20].[Na]>ClCCl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[CH2:10][NH:20][CH2:19][CH2:18][CH:14]1[CH2:15][CH2:16][CH2:17][N:13]1[CH3:12] | CN1CCCC1CCN | O=Cc1cc2ccccc2[nH]1 | null | [Na] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | null | Experimental condition analogous to Example 5, from 1H-indole-2-carbaldehyde 0.14 g (2 mmol), 2-(1-methyl-pyrrolidin-2-yl)-ethylamine 0.3 g (2.4 mmol), and sodium triacethoxyborohydride 0.87 g (1.87 mmol), in 20 mL Dichloromethane. The compound was purified using silica gel chromatography elution, ethyl-acetate-methano... | CN1CCCC1CCNCc1cc2ccccc2[nH]1 | null | 58.3 | null |
1,575,631 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | [NH:1]1[CH:5]=[C:4]([C:6]2[N:11]3[N:12]=[C:13]([NH:15][C:16]4[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][N:25]5[CH2:29][CH2:28][CH2:27][CH2:26]5)=[CH:18][CH:17]=4)[N:14]=[C:10]3[CH:9]=[CH:8][CH:7]=2)[CH:3]=[N:2]1.C(N(CC)CC)C.[CH3:37][S:38](Cl)(=[O:40])=[O:39]>ClCCl>[CH3:37][S:38]([N:2]1[CH:3]=[C:4]([C:6]2[N:11]3[N:12]... | CS(=O)(=O)Cl | c1cc(-c2cn[nH]c2)n2nc(Nc3ccc(OCCN4CCCC4)cc3)nc2c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 18 | To a stirred solution of [5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine (0.05 g, 0.128 mmol) in dichloromethane (1 ml) was added triethylamine (23 μl, 0.166 mmol) followed by methanesulfonyl chloride (12 μl, 0.154 mmol). The mixture was stirred for 18 hours at room ... | CS(=O)(=O)n1cc(-c2cccc3nc(Nc4ccc(OCCN5CCCC5)cc4)nn23)cn1 | null | null | null |
1,723,770 | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | null | 2016-01-01T00:05:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:17][CH:16]([OH:18])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.O>[C:1]([O:5][C:6]([N:8]1[CH2:17][C:16](=[O:18])[C:15]2[C:10](=[CH:11... | CC(C)(C)OC(=O)N1Cc2ccc(OCc3ccccc3)cc2C(O)C1 | null | null | CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)c2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O | null | null | null | null | null | null | null | null | null | 25 | null | To 500 mg (1.41 mmol) 6-benzyloxy-4-hydroxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (example XL) in 8 mL DCM are added 618 mg (1.41 mmol) Dess-Martin periodinane and stirred at r.t. over night. After that time, the reaction mixture is diluted with water and extracted with DCM. The organic layer i... | CC(C)(C)OC(=O)N1CC(=O)c2cc(OCc3ccccc3)ccc2C1 | null | null | null |
254,594 | ord_dataset-cf82113c6dd341d4a014b4667994f01c | null | 1992-01-01T00:09:00 | true | [C:1]([CH2:3][C@H:4]1[O:13][C:8]2([CH2:12][CH2:11][CH2:10][CH2:9]2)[O:7][C@@H:6]([CH2:14][C:15]([OH:17])=[O:16])[CH2:5]1)#[N:2].N.O.[H][H]>CO>[NH2:2][CH2:1][CH2:3][C@H:4]1[O:13][C:8]2([CH2:12][CH2:11][CH2:10][CH2:9]2)[O:7][C@@H:6]([CH2:14][C:15]([OH:17])=[O:16])[CH2:5]1 | [H][H] | N#CC[C@@H]1C[C@H](CC(=O)O)OC2(CCCC2)O1 | null | N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CO | null | null | null | null | null | null | null | null | null | 45 | null | A solution of 1.17 g (4.88 mmol) of (±)-cis-9-(cyanomethyl)-6,10-dioxaspiro[4.5]decane-7-acetic acid in 100 mL of methanol saturated with anhydrous ammonia is added to a Parr shaker bottle containing 0.53 g of water wet Raney nickel #30. The solution is heated at 45° C. and 50 pounds per square inch gage (psig) hydroge... | NCC[C@@H]1C[C@H](CC(=O)O)OC2(CCCC2)O1 | null | 47.2 | null |
401,533 | ord_dataset-7fed188163cf4ccca934ec71504c7f8a | null | 1998-01-01T00:05:00 | true | [NH2:1][CH2:2][CH2:3][CH2:4][OH:5].[Cl:6][C:7]1[CH:22]=[CH:21][C:10]([C:11]([C:13]2[CH:20]=[CH:19][C:16]([CH2:17]Br)=[CH:15][CH:14]=2)=[O:12])=[CH:9][CH:8]=1>C(O)C>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([C:11]([C:13]2[CH:20]=[CH:19][C:16]([CH2:17][NH:1][CH2:2][CH2:3][CH2:4][OH:5])=[CH:15][CH:14]=2)=[O:12])=[CH:21][CH:22]=1 | NCCCO | O=C(c1ccc(Cl)cc1)c1ccc(CBr)cc1 | 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 | 25 | null | To a solution of 3-amino-l-propanol (3.00 g) in ethanol (40 ml) was added 4-(4-chlorobenzoyl)benzyl bromide (3.10 g) and the mixture was refluxed for 4.5 hours. After cooling to room temperature, the solvent was distilled off under reduced pressure and the residue was extracted with ethyl acetate. The extract was dried... | O=C(c1ccc(Cl)cc1)c1ccc(CNCCCO)cc1 | null | 44.7 | null |
374,690 | ord_dataset-ee5599340390470d8e5b5ac1feddf9d6 | null | 1997-01-01T00:08:00 | true | Cl.[NH2:2][CH:3]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=1)[CH2:4][C:5]([O:7][CH3:8])=[O:6].[C:19]([O-:22])(=O)[CH3:20].[Na+]>C(O)(=O)C>[C:5]1(=[O:6])[N:2]([CH:3]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=2)[CH2:4][C:5]([O:7][CH3:8])=[O:6])[C:19](=[O:22]... | COC(=O)CC(N)c1ccc(OC)c(OC)c1 | CC(=O)[O-] | null | Cl | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | 0.5 | A stirred mixture of 1,2,5,6-hexahydrophthalic anhydride (0.77 grams, 5.0 mmol), methyl 3-amino-3-(3,4-dimethoxyphenyl)propionate hydrochloride (1.38 grams, 5.0 mmol), and sodium acetate (0.40 grams, 4.9 mmol) in 20 mL of acetic acid under N2 was heated to reflux for 20 hours. The cooled reaction mixture was concentrat... | COC(=O)CC(c1ccc(OC)c(OC)c1)N1C(=O)[C@H]2CCCC[C@H]2C1=O | null | 76.7 | null |
633,175 | ord_dataset-de283386b8034acd99fba96d3c7d3227 | null | 2004-01-01T00:04:00 | true | [NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C@@H:11]([NH:16][S:17]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]#[C:29][CH3:30])=[CH:22][CH:21]=2)(=[O:19])=[O:18])[C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=1.[C:31](OC(=O)C)(=[O:33])[CH3:32]>N1C=CC=CC=1>[C:31]([NH:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][... | CC#CCOc1ccc(S(=O)(=O)N[C@@H](C(=O)OC)c2ccc(OCCN)cc2)cc1 | CC(=O)OC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 0.219 g (0.507 mmol) of methyl(2R)-[4-(2-aminoethoxy)phenyl]({[4-(2-butynyloxy)phenyl]sulfonyl}amino)ethanoate in 2.5 mL of acetic anhydride and 0.25 mL of pyridine was stirred at room temperature for 15 h and then concentrated in vacuo. The residue was chromatographed on silica gel eluting with ethyl ace... | CC#CCOc1ccc(S(=O)(=O)N[C@@H](C(=O)OC)c2ccc(OCCNC(C)=O)cc2)cc1 | null | null | null |
1,213,830 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | [CH3:1][C:2]1([CH3:20])[CH2:6][C:5]2[C:7]([CH3:19])=[C:8]([N:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[C:9]([CH3:12])=[C:10]([CH3:11])[C:4]=2[O:3]1.Br[C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([O:29][CH3:30])[CH:23]=1>>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([N:16]2[CH2:15][CH2:14][N:13]([C:8]3[C:9]([CH3:12])=[C:10](... | Cc1c(C)c(N2CCNCC2)c(C)c2c1OC(C)(C)C2 | COc1cc(Br)ccc1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | By using 1-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazine (274 mg, 1.00 mmol) synthesized in Reference example 61 and 4-bromo-1-chloro-2-methoxybenzene (332 mg, 1.50 mmol), the reaction was carried out in the same manner as Example 23 to obtain the title compound 100 mg (yield 24%). Melting point was 1... | COc1cc(N2CCN(c3c(C)c(C)c4c(c3C)CC(C)(C)O4)CC2)ccc1Cl | null | 24.1 | null |
1,341,024 | ord_dataset-08852243bba44cb28769a5833f1515fe | null | 2013-01-01T00:09:00 | true | [O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([CH2:11][CH2:12][OH:13])[CH2:7][CH2:6]2)OCC1.C1COCC1.Cl.C([O-])(O)=O.[Na+]>CC(C)=O>[OH:13][CH2:12][CH2:11][CH:8]1[CH2:9][CH2:10][C:5](=[O:1])[CH2:6][CH2:7]1 | OCCC1CCC2(CC1)OCCO2 | null | null | Cl | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 16 | 2-(1,4-Dioxaspiro[4.5]dec-8-yl)ethanol (2.70 g, 0.0145 mol) was dissolved in acetone (10.00 mL) and THF (10.00 mL) and 6.00 M HCl (6.00 mL) was added. The reaction was stirred at 25° C. for 16 hours, neutralized with NaHCO3 solution and was then extracted with ethyl acetate. The organic extracts were washed with water,... | O=C1CCC(CCO)CC1 | null | null | null |
1,199,835 | ord_dataset-fb72428f30234761b4216139dc228d0c | null | 2012-01-01T00:09:00 | true | [CH:1]1([NH:8][C:9]2[N:14]3[N:15]=[C:16]([NH2:18])[N:17]=[C:13]3[CH:12]=[CH:11][CH:10]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[O:19]1[CH2:24][CH2:23][CH:22]([C:25](Cl)=[O:26])[CH2:21][CH2:20]1>>[CH:1]1([NH:8][C:9]2[N:14]3[N:15]=[C:16]([NH:18][C:25]([CH:22]4[CH2:23][CH2:24][O:19][CH2:20][CH2:21]4)=[O:26])[N:17]=[... | Nc1nc2cccc(NC3CCCCCC3)n2n1 | O=C(Cl)C1CCOCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared following procedure described for intermediate B1, but starting from N5-cycloheptyl[1,2,4]triazolo[1,5-a]pyridine-2,5-diamine ((A10), 50 mg; 0.20 mmol; 1.0 eq.) and tetrahydro-2H-pyran-4-carbonyl chloride (45 mg; 0.30 mmol; 1.5 eq.) as a white solid (33 mg, 46%). HPLC, Rt: 3.02 min. (pur... | O=C(Nc1nc2cccc(NC3CCCCCC3)n2n1)C1CCOCC1 | null | null | null |
48,521 | ord_dataset-b43eb0158fd54801957aaa07bbdf3057 | null | 1978-01-01T00:11:00 | true | [CH3:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:3]=1[NH:4][CH2:5][C:6]([OH:8])=[O:7].[OH-].[Na+].[Cl:16][CH2:17][C:18](Cl)=[O:19]>C(Cl)Cl>[Cl:16][CH2:17][C:18]([N:4]([CH2:5][C:6]([OH:8])=[O:7])[C:3]1[C:9]([CH3:13])=[CH:10][CH:11]=[CH:12][C:2]=1[CH3:1])=[O:19] | O=C(Cl)CCl | Cc1cccc(C)c1NCC(=O)O | null | [Na+] | [OH-] | 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 | 0.5 | 36 g (0.2 mole) of 2,6-dimethylanilinoacetic acid, 400 ml of methylene chloride and 200 ml of 1N NaOH (0.2 mole) are placed into a flask with stirrer, and 17.5 ml (0.22 mole) of chloroacetic acid chloride is slowly added dropwise with stirring, the temperature being maintained at 20°-25° by cooling with ice-water. Duri... | Cc1cccc(C)c1N(CC(=O)O)C(=O)CCl | null | null | null |
737,638 | ord_dataset-76dd1b78ee414d2da0ed30700ef026f7 | null | 2006-01-01T00:10:00 | true | Cl.Cl[CH2:3][C:4]1[C:9]([CH3:10])=[C:8]([O:11][CH3:12])[C:7]([CH3:13])=[CH:6][N:5]=1.[NH3:14].CO>>[NH2:14][CH2:3][C:4]1[C:9]([CH3:10])=[C:8]([O:11][CH3:12])[C:7]([CH3:13])=[CH:6][N:5]=1 | COc1c(C)cnc(CCl)c1C | N | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 2-chloromethyl-4-methoxy-3,5-dimethyl-pyridine HCl (Aldrich 3.7 g, 16.6 mmole) in 7N NH3/MeOH (Aldrich, 200 mLs) was refluxed in a steel bomb for 15 hours. Removed the solvent under reduced pressure, the residue was taken into 5% MeOH/CH2Cl2 and filtering it through a thin layer of silica gel afforded the... | COc1c(C)cnc(CN)c1C | null | 76 | null |
75,343 | ord_dataset-b9d8ddf9c2884d40859b6b5f24815a7d | null | 1980-01-01T00:12:00 | true | [OH:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[N:3]1.C(N(CC)CC)C.[CH3:18][C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH3:26])[C:20]=1[S:27](Cl)(=[O:29])=[O:28]>ClCCl>[CH3:18][C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH3:26])[C:20]=1[S:27]([O:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[N:3... | On1nnc2ccccc21 | Cc1cc(C)c(S(=O)(=O)Cl)c(C)c1 | 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 | 1 | In dichloromethane (70 ml) are added 1-hydroxy-1,2,3-benzotriazole (3.4 g) and further triethylamine (3.7 ml). To the solution is added dropwise a solution of 2,4,6-trimethylbenzenesulfonyl chloride (4.5 g) is dichloromethane (20 ml) at room temperature, and the mixture is stirred for 1 hour. The reaction mixture is wa... | Cc1cc(C)c(S(=O)(=O)On2nnc3ccccc32)c(C)c1 | null | 84.2 | null |
722,341 | ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | null | 2006-01-01T00:08:00 | true | C[O:2][C:3]1[CH:15]=[C:14]2[C:6]([C:7]3[CH:12]([CH:13]2[CH2:16][CH2:17][CH3:18])[CH2:11][CH2:10][C:9](=[O:19])[C:8]=3[CH3:20])=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:15]=[C:14]2[C:6]([C:7]3[CH:12]([CH:13]2[CH2:16][CH2:17][CH3:18])[CH2:11][CH2:10][C:9](=[O:19])[C:8]=3[CH3:20])=[CH:5][CH:4]=1 | CCCC1c2cc(OC)ccc2C2=C(C)C(=O)CCC21 | null | null | BrB(Br)Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 2.6 | A solution of (9SR,9aSR)-7-methoxy-4-methyl-9-propyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (38.3 mg, 0.142 mmol) in anhydrous CH2Cl2 (1.1 mL) was placed under a nitrogen atmosphere, cooled in a dry ice-acetone bath, and stirred while 1M BBr3 in CH2Cl2 (0.354 mL, 0.345 mmol) was added by syringe. The cooling bath was rem... | CCCC1c2cc(O)ccc2C2=C(C)C(=O)CCC21 | null | null | null |
1,308,479 | ord_dataset-78c3f723155a4347a902b53bcee1524d | null | 2013-01-01T00:06:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]([CH3:34])[C@@H:11]2[CH2:16][CH2:15][N:14]([C:17]3[N:22]=[CH:21][C:20]([C:23]([OH:25])=O)=[CH:19][CH:18]=3)[CH2:13][C@H:12]2[C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=2)=[O:9])=[CH:4][CH:3]=1.[NH3:35]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]([CH3:34])[C@@... | N | CN(C(=O)c1ccc(Cl)cc1)[C@@H]1CCN(c2ccc(C(=O)O)cn2)C[C@H]1c1ccc(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 | Using the compound obtained in Example 500 and aqueous ammonia, and by the reaction and purification in the same manner as in Example 510, the title compound was obtained. | CN(C(=O)c1ccc(Cl)cc1)[C@@H]1CCN(c2ccc(C(N)=O)cn2)C[C@H]1c1ccc(Cl)c(Cl)c1 | null | null | null |
1,571,161 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | O.[OH-].[Li+].C[O:5][C:6](=[O:36])[CH2:7][C:8]1[C:17]([CH3:18])=[C:16]([C:19]2[CH:24]=[CH:23][C:22]([S:25]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=3)(=[O:27])=[O:26])=[CH:21][CH:20]=2)[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([Cl:35])[CH:14]=2)[CH:9]=1>C1COCC1.O>[Cl:35][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:1... | COC(=O)Cc1cc2ccc(Cl)cc2c(-c2ccc(S(=O)(=O)c3ccc(Cl)cc3)cc2)c1C | null | null | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 16 | Lithium hydroxide monohydrate (0.015 g, 0.35 mmol) was added to a stirred solution of {6-chloro-4-[4-(4-chloro-benzenesulfonyl)-phenyl]-3-methyl-naphthalen-2-yl}-acetic acid methyl ester (0.043 g, 0.086 mmol) in a 3:1 THF—H2O mixture (4 mL). The reaction mixture was stirred for 16 hours at room temperature. The THF was... | Cc1c(CC(=O)O)cc2ccc(Cl)cc2c1-c1ccc(S(=O)(=O)c2ccc(Cl)cc2)cc1 | null | 93.4 | null |
714,972 | ord_dataset-c8a367b56b4f406b878f51867b157d19 | null | 2006-01-01T00:06:00 | true | Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][N:13]=2)=[CH:7][CH:6]=1)=[O:3].Cl.[CH3:23][N:24]([CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1>>[F:19][C:18]([F:21])([F:20])[C:15]1[CH:16]=[CH... | CN(CCc1ccccc1)C1CCNCC1 | O=C(Cl)Oc1ccc(Oc2ccc(C(F)(F)F)cn2)cc1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from 4-(5-trifluoromethyl-pyridin-2-yloxy)-phenyl chloroformate and methyl-phenethyl-piperidin-4-yl-amine, hydrochloride, praeparative HPLC (Method C) (37%, colourless oil). HPLC-MS m/z=500.1 (M+1), Rt: 3.26 min. | CN(CCc1ccccc1)C1CCN(C(=O)Oc2ccc(Oc3ccc(C(F)(F)F)cn3)cc2)CC1 | null | null | null |
626,421 | ord_dataset-e44331dc51de453ca14b7032593c1958 | null | 2004-01-01T00:02:00 | true | [NH2:1][C:2]1[C:11]([NH2:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[N:13]1[C:17]2[CH:18]=[CH:19][C:20]([C:22](O)=O)=[CH:21][C:16]=2[NH:15][CH:14]=1>>[N:13]1[C:17]2[CH:18]=[CH:19][C:20]([C:22]3[NH:1][C:2]4[C:3]([C:4]([OH:6])=[O:5])=[CH:8][CH:9]=[CH:10][C:11]=4[N:12]=3)=[CH:21][C:16]=2[NH:15][CH:14]=1 | COC(=O)c1cccc(N)c1N | O=C(O)c1ccc2nc[nH]c2c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 200 | null | 2 g (12 mmol) of methyl 2,3-diaminobenzoate and 2 g (12 mmol) of benzimidazole-5-carboxylic acid were successively introduced into 70 ml of polyphosphoric acid preheated to 90° C. The mixture was then heated at 200° C. for 1 hour. The reaction mixture was subsequently cooled to 50 to 60° C. and poured cautiously into i... | O=C(O)c1cccc2nc(-c3ccc4nc[nH]c4c3)[nH]c12 | null | 80.9 | null |
732,981 | ord_dataset-76dd1b78ee414d2da0ed30700ef026f7 | null | 2006-01-01T00:10:00 | true | Cl.[C:2]([O:6][C:7]([C:9]1[C:17]2[CH:16]([N:18]=[C:19]=[O:20])[CH:15]([CH2:21][N:22]3C(=O)C4C(=CC=CC=4)C3=O)[NH:14][CH2:13][C:12]=2[S:11][C:10]=1[O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:8])([CH3:5])([CH3:4])[CH3:3].NN>C(O)C>[C:2]([O:6][C:7]([C:9]1[C:17]2[CH:16]([N:18]=[C:19]=[O:20])[CH:15]([CH2:... | CC(C)(C)OC(=O)c1c(OCc2ccccc2)sc2c1C(N=C=O)C(CN1C(=O)c3ccccc3C1=O)NC2 | null | null | Cl | NN | 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 | 80 | 16 | To a solution of the above 2-benzyloxy-carbonylamino-5-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester hydrochloride (42 mg, 0.072 mmol) in ethanol (0.5 ml) was added hydrazine (68 μl, 0.22 mmol). The solution was stirred at 80° C. for 5 h. and at ... | CC(C)(C)OC(=O)c1c(OCc2ccccc2)sc2c1C(N=C=O)C(CN)NC2 | null | 66.9 | null |
1,141,579 | ord_dataset-68715347640045adb1b09e6a04722b0e | null | 2012-01-01T00:03:00 | true | [CH3:1][O:2][C:3](=[O:16])[C:4](=O)[CH:5](Cl)[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=1.[C:17]([NH2:20])(=[S:19])[CH3:18]>>[CH3:1][O:2][C:3]([C:4]1[N:20]=[C:17]([CH3:18])[S:19][C:5]=1[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=1)=[O:16] | CC(N)=S | COC(=O)C(=O)C(Cl)c1cccc(OC)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | prepared by reaction of 3-chloro-3-(3-methoxy-phenyl)-2-oxo-propionic acid methyl ester with thioacetamide. LC-MS: tR=0.90 min; [M+H]+=263.9. | COC(=O)c1nc(C)sc1-c1cccc(OC)c1 | null | null | null |
516,554 | ord_dataset-a495451286334c5c9bbcbd48a00c1350 | null | 2001-01-01T00:09:00 | true | [C:1]([O:5][C:6]([NH:8][C@@H:9]([C:19]([OH:21])=O)[CH2:10][O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:22][C@@H:23]1[CH2:47][CH2:46][C@@:45]2([CH3:48])[CH:25]([CH2:26][CH2:27][C@@H:28]3[C@@H:44]2[CH2:43][CH2:42][C@@:41]2([CH3:49])[C@H:29]3[CH2:30][CH2:31][C@@H:32]2[... | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4C[C@H](N)CC[C@]4(C)[C@H]3CC[C@]12C | CC(C)(C)OC(=O)N[C@H](COCc1ccccc1)C(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | By using N-tert-butyloxycarbonyl-O-benzyl-D-serine (600 mg, 2.03 mmol) and 3α-aminocholestane (866 mg, 2.23 mmol), the title compound was obtained in the same manner as in Synthetic Example BB1 (1.13 g, yield; 83%). | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4C[C@H](NC(=O)[C@@H](COCc5ccccc5)NC(=O)OC(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C | null | 83 | null |
572,648 | ord_dataset-f4512fe8cd804ac79da66cbc0c2b9d42 | null | 2002-01-01T00:12:00 | true | [NH:1]1[CH2:5][CH2:4][CH:3]([CH2:6][C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:16]#[N:17])[CH:14]=3)[NH:9][CH:8]=2)[CH2:2]1.[Cl:18][CH2:19][CH2:20][N:21]1[C:30](=[O:31])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[NH:23][C:22]1=[O:32].C(=O)([O-])O.[Na+].Cl>CN(C)C=O.C(O)C>[ClH:18].[O:32]=[C:22]1[N:21]([CH2:20][CH2:... | O=c1[nH]c2ccccc2c(=O)n1CCCl | N#Cc1ccc2[nH]cc(CC3CCNC3)c2c1 | null | Cl | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCO | null | null | null | null | null | null | null | null | null | null | 6 | Under an inert atmosphere and at ambient temperature, 47.3 mmol (10 g) of 3-[3-pyrrolidinylmethyl]-1H-indole-5-carbonitrile, 47.3 mmol (9.97 g) of 3-(2-chloroethyl)-2,4-(1H,3H)-quinazolinedione and 47.3 mmol (3.73 g) of sodium hydrogen carbonate are dissolved in 100 ml of dimethylformamide, and stirring is carried out ... | N#Cc1ccc2[nH]cc(CC3CCN(CCn4c(=O)[nH]c5ccccc5c4=O)C3)c2c1 | null | null | null |
603,915 | ord_dataset-273fda773e864aaf9b71a30a2d9f2162 | null | 2003-01-01T00:08:00 | true | [Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([OH:9])=[C:4]([Cl:10])[CH:3]=1.CN(C=O)C.[Si:16](Cl)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]>O>[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])=[C:4]([Cl:10])[CH:3]=1 | CC(C)(C)[Si](C)(C)Cl | Oc1c(Cl)cc(Br)cc1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 1 | To a solution of 4-bromo-2,6-dichlorophenol (11.9 g, 49.2 mmol, H. Joyce et al., J. Amer. Chem. Soc., 39, 2644 (1917)) in DMF (100 mL) imidazole (5.0 g, 74 mmol) and tert-butyldimethylsilylchloride (8.9 g, 59 mmol) was added at room temperature and the mixture was stirred for 1 h. The mixture was poured into water (300... | CC(C)(C)[Si](C)(C)Oc1c(Cl)cc(Br)cc1Cl | null | null | null |
1,216,527 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | [F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[C:4]([C:11]2[N:12]=[C:13]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)[C:14]3[S:19][C:18]([CH2:20][N:21]4[CH2:26]CN5CCC[C@H]5[CH2:22]4)=[CH:17][C:15]=3[N:16]=2)[CH:3]=1.Cl.C(OC([N:44]1[CH2:52][CH2:51][C:47]2(CNC2)[CH2:46][CH2:45]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl... | CC(C)(C)OC(=O)N1CCC2(CC1)CNC2 | Fc1cc(-c2nc(N3CCOCC3)c3sc(CN4CCN5CCC[C@H]5C4)cc3n2)c2cc[nH]c2c1 | null | Cl | 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 | null | null | Prepared according to the method used in the preparation of 2-(6-fluoro-1H-indol-4-yl)-6-[(S)-1-(hexahydro-pyrrolo[1,2-a]pyrazin-2-yl)methyl]-4-morpholin-4-yl-thieno-[3,2-d]pyrimidine using 2,7-diaza-spiro[3.5]nonane-7-carboxylic acid tert-butyl ester hydrochloride in place of (S)-octahydro-pyrrolo[1,2-c]pyrazine, foll... | Fc1cc(-c2nc(N3CCOCC3)c3sc(CN4CC5(CCNCC5)C4)cc3n2)c2cc[nH]c2c1 | null | null | null |
786,064 | ord_dataset-4ad5db8537994579bef51f16dd8bf0bd | null | 2007-01-01T00:08:00 | true | [CH3:1][O:2][C:3](=[O:16])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][C:7]=1[CH3:15].[H][H]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:16])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][C:7]=1[CH3:15] | COC(=O)C=Cc1ccc([N+](=O)[O-])cc1C | [H][H] | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 3-(2-Methyl-4-nitro-phenyl)-acrylic acid methyl ester (1.47 g, 6.64 mmol) and 5% Pd/C (0.29 g) in MeOH (100 mL) is exposed to a hydrogen atmosphere (60 psi) for 12 h. The mixture is filtered through Celite and purified by flash chromatography to yield the title compound (0.99 g, 77%). | COC(=O)CCc1ccc(N)cc1C | null | 77.2 | null |
1,333,631 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1B(O)O.[I:12][C:13]1[N:14]=[CH:15][NH:16][CH:17]=1>[Cu]Cl.CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[N:16]1[CH:17]=[C:13]([I:12])[N:14]=[CH:15]1 | Ic1c[nH]cn1 | OB(O)c1cc(F)ccc1F | null | Cl[Cu] | 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 | Following a procedure similar to that outlined in Chem. Comm. 2004, 188-189: A solution of 2,5-difluorophenylboronic acid (47 mg, 0.30 mmol), 4-iodo-1H-imidazole (46 mg, 0.24 mmol), copper(I) chloride (1.8 mg, 0.018 mmol), and 1 mL of methanol was stirred under air at 60° C. for 3 h, then concentrated. Column chromatog... | Fc1ccc(F)c(-n2cnc(I)c2)c1 | null | 19.7 | null |
729,352 | ord_dataset-eb4226b4f7644a01a737e7547b70014a | null | 2006-01-01T00:09:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8](C(O)=O)[CH:7]=[CH:6]2.[N-:16]=[N+]=[N-].[Na+]>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([NH2:16])[CH:7]=[CH:6]2 | [N-]=[N+]=[N-] | COc1ccc2cc(C(=O)O)ccc2c1 | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | 40 | 12 | To a 50 ml two-necked flask, 1.0 g (3.5 mmol) of 6-methoxynaphthalene-2-carboxylic acid (Compound 1), 2.28 g (35.0 mmol) of sodium azide and 15.0 g of polyphosphoric acid (PPA) were added, and the mixture was stirred at 40° C. for 12 hours. To the resulting mixture, 100 g of ethyl acetate was added and the obtained mix... | COc1ccc2cc(N)ccc2c1 | null | null | null |
1,280,691 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [F:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[F:27])[CH2:5][C@H:6]1[CH2:11][C@@H:10]([C:12](=[O:19])[CH2:13][C:14](OCC)=[O:15])[CH2:9][CH2:8][N:7]1[C:20]([O:22][CH3:23])=[O:21].[OH-].[Na+].[NH2:30]O.Cl>CO.O>[F:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[F:27])[CH2:5][C@H:6]1[CH2:11][C@@H:10]([C:12]2[O:19][NH:30][C:1... | NO | CCOC(=O)CC(=O)[C@H]1CCN(C(=O)OC)[C@@H](Cc2ccc(F)c(F)c2)C1 | null | Cl | [Na+] | [OH-] | 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 | -40 | 0.33 | Cis-methyl 2-(3,4-difluorobenzyl)-4-(3-ethoxy-3-oxopropanoyl)piperidine-1-carboxylate (2.233 g, 5.82 mmol) was dissolved in MeOH (20 mL) and cooled to −40° C. under nitrogen. Sodium hydroxide (0.233 g, 5.82 mmol) dissolved in water (2.000 mL) was added during 10 min and the yellow solution continued to stir at −40° C. ... | COC(=O)N1CC[C@H](c2cc(=O)[nH]o2)C[C@@H]1Cc1ccc(F)c(F)c1 | null | 66.4 | null |
955,229 | ord_dataset-3feb2a95f66e4706a4a50c977ccd9bf8 | null | 2010-01-01T00:04:00 | true | [OH:1][CH2:2][C:3]#[C:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[CH2:9][CH2:8]2>CO.[Pd]>[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[CH2:9][CH2:8]2 | O=C1CCc2cc(C#CCO)ccc21 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | 12 | To a solution of 5-(hydroxyprop-1-yn-1-yl)-2,3-dihydro-1H-indene-1-one (1.06 g, 5.71 mmol) in MeOH was added 10% Pd/C and hydrogenated by means of Pair shaker. After 12 h, the reaction mixture was filtered on Celite and concentrated in vacuo to give 5-(3-hydroxypropyl)-2,3-dihydro-1H-inden-1-one (1.03 g, 94% yield): MS... | O=C1CCc2cc(CCCO)ccc21 | null | 94.8 | null |
391,346 | ord_dataset-4bc8addcf9cf4845817557760d62d5b5 | null | 1998-01-01T00:02:00 | true | [F:1][C:2]([F:43])([F:42])[C:3]([C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[C:27]([C:32]([OH:41])([C:37]([F:40])([F:39])[F:38])[C:33]([F:36])([F:35])[F:34])[CH:26]=1)([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([C:15]([C:21]([F:24])([F:23])[F:22])([OH:20])[C:16]([F:19])([F:18])[F:17])[CH:9]=1)[C:4]([F:7])([F:6])[F:5].C(N(... | CS(=O)(=O)Cl | Cc1ccc(C(c2ccc(C)c(C(O)(C(F)(F)F)C(F)(F)F)c2)(C(F)(F)F)C(F)(F)F)cc1C(O)(C(F)(F)F)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 25 | 24 | 10.1 g (15.2 mmol) of 1,1,1,3,3,3-hexafluoro-2,2-bis-[4-methyl-3-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-phenyl]-propane were dissolved in 50 ml of methylene chloride, and 3.4 g (33 mmol) of triethylamine were added at 0° C. 4.0 g (34.7 mmol) of methanesulfonyl chloride in 20 ml of methylene chloride were a... | Cc1ccc(C(c2ccc(C)c(C(OS(C)(=O)=O)(C(F)(F)F)C(F)(F)F)c2)(C(F)(F)F)C(F)(F)F)cc1C(OS(C)(=O)=O)(C(F)(F)F)C(F)(F)F | null | 73.8 | null |
1,679,324 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | [CH3:1][O:2][Si:3](OC)([CH3:5])[CH3:4].C(OCC)C.[CH2:13]([Si:16]([CH2:25][CH:26]=[CH2:27])([CH2:22][CH:23]=[CH2:24])[CH2:17][CH2:18][CH2:19][Mg]Br)[CH:14]=[CH2:15].Cl>O>[CH2:13]([Si:16]([CH2:25][CH:26]=[CH2:27])([CH2:22][CH:23]=[CH2:24])[CH2:17][CH2:18][CH2:19][Si:3]([O:2][CH3:1])([CH3:5])[CH3:4])[CH:14]=[CH2:15] | CO[Si](C)(C)OC | C=CC[Si](CC=C)(CC=C)CCC[Mg]Br | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCOCC | null | null | null | null | null | null | null | null | null | 0 | 5 | Under a nitrogen atmosphere, dimethoxydimethylsilane (31) (1.0 ml, 7.0 mmol) was added to a reaction container, cooled down to 0° C., diethyl ether solution of 0.72M 3-(triallylsilyl)propylmagnesium bromide (24) (19.44 mL, 14 mmol) was added dropwise. After the dropwise adding, stirring was continued at room temperatur... | C=CC[Si](CC=C)(CC=C)CCC[Si](C)(C)OC | null | 72 | null |
988,892 | ord_dataset-35b56288528641309a040cc2b6710b61 | null | 2010-01-01T00:08:00 | true | [F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](I)[C:3]=1[OH:9].[OH-:10].[K+].Cl>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:10])[C:3]=1[OH:9] | [OH-] | Oc1c(F)cccc1I | null | Cl | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 8 | To a 500 ml flask were added 119 g (0.5 mol) of 2-fluoro-6-iodophenol and 200 ml of a 30% aqueous potassium hydroxide solution and they were reacted under vigorous stirring under a reflux temperature for 8 hours. After the termination of the reaction, the mixture was cooled to ordinary temperature and neutralized with ... | Oc1cccc(F)c1O | null | 78 | null |
573,044 | ord_dataset-f4512fe8cd804ac79da66cbc0c2b9d42 | null | 2002-01-01T00:12:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[Cl:9][C:10]1[C:11](F)=[CH:12][C:13]2[O:18][CH:17]([C:19]([F:22])([F:21])[F:20])[C:16]([C:23]([O:25]CC)=[O:24])=[CH:15][C:14]=2[CH:28]=1>>[Cl:9][C:10]1[C:11]([S:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[CH:12][C:13]2[O:18][CH:17]([C:19]([F:21])([F:20])[F:2... | Sc1ccc(Cl)cc1 | CCOC(=O)C1=Cc2cc(Cl)c(F)cc2OC1C(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 4-chlorobenzenethiol and ethyl 6-chloro-7-fluoro-2-(trifluoromethyl)-2H-1-benzopyran-3-carboxylate (Example 183, Step 2) via a procedure similar to that described in Example 183, Steps 3 and 4: mp 251.7-253.3° C. 1H NMR (acetone-d6/300 MHz) 7.86 (s, 1H), 7.62 (m, 5H), 6.39 (s, 1H), ... | O=C(O)C1=Cc2cc(Cl)c(Sc3ccc(Cl)cc3)cc2OC1C(F)(F)F | null | null | null |
1,173,045 | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | null | 2012-01-01T00:05:00 | true | I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-])=O.[C:11]([NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)(=O)[CH3:12]>>[CH3:12][C:11]1[N:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N:8]=1 | CC(=O)Nc1ccccn1 | O=[N+]([O-])c1ccccc1I | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Method A applied to 1-iodo-2-nitrobenzene (125 mg, 0.5 mmol) and 2-acetamido-pyridine (82 mg, 0.6 mmol) yielded the title compound as brown solid (40 mg, 38%). mp 121-123° C. 1H NMR (DMSO) δ 2.69 (s, 3H), 7.36-7.46 (m, 2H), 7.53 (d, J=7.4 Hz, 1H), 7.68 (dd, J=7.6, 4.7Hz, 1H), 7.77 (d, J=7.6Hz, 1H), 7.81 (d, J=7.9Hz, 1H... | Cc1nc2ccccc2n1-c1ccccn1 | null | 38.2 | null |
1,628,064 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | [NH:1]1[CH2:5][CH2:4][CH2:3][C@@H:2]1[C:6]([NH:8][C@H:9]([C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1)[CH3:10])=[O:7].[CH3:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH2:25]Br.C([O-])([O-])=O.[Na+].[Na+]>>[CH3:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH2:25][N:1]1[CH2:5... | Cc1cccc(CBr)c1 | COC(=O)c1ccc([C@H](C)NC(=O)[C@H]2CCCN2)cc1 | null | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound (D33) (30 mg) was prepared according to the general procedure for substituted benzyl amines preparation starting from methyl 4-((S)-1-((R)-pyrrolidine-2-carboxamido)ethyl)benzoate (D14) (50 mg, 0.18 mmol) and 3-methylbenzyl bromide (0.05 ml, 0.36 mmol). (Na2CO3: 2.5 eq; reaction time: 5 hrs; 70° C.) | COC(=O)c1ccc([C@H](C)NC(=O)[C@H]2CCCN2Cc2cccc(C)c2)cc1 | null | 43.8 | null |
1,335,781 | ord_dataset-08852243bba44cb28769a5833f1515fe | null | 2013-01-01T00:09:00 | true | C(OC([N:8]([CH2:34][C:35]1[CH:44]=[CH:43][C:38]2[O:39][CH2:40][CH2:41][O:42][C:37]=2[CH:36]=1)[CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][N:17]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([O:27][CH3:28])[CH:25]=3)[C:20]([C:29]([O:31][CH3:32])=[O:30])=[CH:19][C:18]2=[O:33])[CH2:11][CH2:10]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)(C... | COC(=O)c1cc(=O)n(CCN2CCC(N(Cc3ccc4c(c3)OCCO4)C(=O)OC(C)(C)C)CC2)c2cc(OC)ccc12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 16 | To 2 mL of a chloroform solution containing 0.25 g of methyl 1-(2-(4-((tert-butoxycarbonyl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-2-oxo-1,2-dihydroquinoline-4-carboxylate, 2 mL of trifluoroacetic acid was added and stirred for 16 hours. The solvent was removed under reduced pressu... | COC(=O)c1cc(=O)n(CCN2CCC(NCc3ccc4c(c3)OCCO4)CC2)c2cc(OC)ccc12 | null | 57.5 | null |
256,916 | ord_dataset-30ad5cf6083a45a387b45bebad1a4d65 | null | 1992-01-01T00:10:00 | true | [CH2:1]([O:8][C:9](=[O:20])[CH2:10][CH2:11][C:12]([N:14]([CH2:16][C:17]([OH:19])=O)[CH3:15])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:21]1[CH2:27][CH2:26][CH2:25][C@H:22]1[CH2:23][OH:24].C(N(CC)CC)C>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:20])[CH2:10][CH2:11][C:12]([N:14]([CH2:16][C:17]([N:21]1[CH2:27][CH2:26][CH2:25... | OC[C@@H]1CCCN1 | CN(CC(=O)O)C(=O)CCC(=O)OCc1ccccc1 | 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 | 3 | N-(benzyloxysuccinyl)sarcosine (139.5 g, 0.5 mol), L-prolinol (50.5 g, 0.5 mol) and triethylamine (200 ml) are dissolved in methylene chloride (2 l), and a solution of DMC (127 g, 0.75 mol) in methylene chloride (500 ml) is added dropwise thereto under water-cooling over a period of thirty minutes. The mixture is stirr... | CN(CC(=O)N1CCC[C@H]1CO)C(=O)CCC(=O)OCc1ccccc1 | null | 48.8 | null |
187,595 | ord_dataset-3ec273742a0345ea916ad5fd071167f2 | null | 1989-01-01T00:04:00 | true | [CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:18]=[CH:17][C:13]([C:14](O)=[O:15])=[CH:12][CH:11]=1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].C([N:21](CC)CC)C.C(Cl)(=O)OCC>C1COCC1>[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([NH2:21])=[O:15])=[CH:12][CH:11]=1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2] | CCN(CC)CC | CCOP(=O)(Cc1ccc(C(=O)O)cc1)OCC | null | CCOC(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | To a solution of 1.36 g of 4-diethoxyphosphinylmethylbenzoic acid and 0.56 g of triethylamine in 15 ml of dry THF was slowly added a solution of 0.60 g of ethyl chlorocarbonate in 2 ml of dry THF under ice-cooling with stirring. After stirring for 30 minutes under ice-cooling, ammonia gas was slowly bubbled into the mi... | CCOP(=O)(Cc1ccc(C(N)=O)cc1)OCC | null | null | null |
869,846 | ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | null | 2009-01-01T00:03:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[C:14]([CH2:16][C:17]#[N:18])[CH:13]=[CH:12][N:11]3[C:19]=2[C:20]2[CH:25]=[CH:24][N:23]=[C:22]([S:26]([CH3:29])(=[O:28])=[O:27])[N:21]=2)=[CH:4][CH:3]=1.C(O)C.[H][H]>O=[Pt]=O.C(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[C:14]([CH2:16][CH2... | CS(=O)(=O)c1nccc(-c2c(-c3ccc(F)cc3)nc3cc(CC#N)ccn23)n1 | [H][H] | null | O=[Pt]=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | 25 | 12 | A 300 mL pressure bottle containing nitrile 22 (980 mg, 2.41 mmol) was charged with ethanol (18 mL), chloroform (2 mL), and then PtO2 (200 mg, 0.881 mmol). The pressure bottle was then sealed, then charged with 50 psi hydrogen, and the reaction mixture was allowed to stir at room temperature for 12 hours, after which a... | CS(=O)(=O)c1nccc(-c2c(-c3ccc(F)cc3)nc3cc(CCN)ccn23)n1 | null | null | null |
1,399,759 | ord_dataset-12dc3bd21bcf44d09e5b4249afe15161 | null | 2014-01-01T00:02:00 | true | [CH3:1][C@H:2]1[O:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[C:18]([CH2:19][OH:20])=[CH:17][C:12]3[C:13]([CH3:16])=[N:14][S:15][C:11]=3[C:10]=2[F:21])[CH2:3]1.C[N+]1([O-])CCOCC1>C(Cl)Cl.CC#N.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[CH3:1][C@H:2]1[O:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[C:18]([CH:19]=[O:20])=[CH:17][C:12]3... | Cc1nsc2c(F)c(N3C[C@@H](C)O[C@@H](C)C3)c(CO)cc12 | null | null | O=[Ru](=O)(=O)[O-] | CCC[N+](CCC)(CCC)CCC | C[N+]1([O-])CCOCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 2 | To an ice-cooled solution of {6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-7-fluoro-3-methyl-1,2-benzothiazol-5-yl}methanol (Intermediate 157, 0.18 g, 0.6 mmol) in DCM/CH3CN mixture (3 mL, 1:1 v/v) was added NMO (0.12 g, 0.7 mmol) followed TPAP (0.04, 0.2 mmol) and mixture stirred for 2 h at room temperature. The reaction mi... | Cc1nsc2c(F)c(N3C[C@@H](C)O[C@@H](C)C3)c(C=O)cc12 | null | null | null |
922,571 | ord_dataset-8e59bd24817446f7b1c68e805b8e5f1d | null | 2009-01-01T00:11:00 | true | [C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]([F:13])([F:12])[F:11])=[N:8][CH:9]=1)([CH3:3])=[CH2:2].CN1C=CN=C1.[N+](=[CH:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[N-]>C1(C)C=CC=CC=1>[CH3:3][C:1]1([C:4]2[CH:9]=[N:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][CH:5]=2)[CH2:2][CH:22]1[C:23]([O:25][CH2:26][CH3:27])=[O:24] | C=C(C)c1ccc(C(F)(F)F)nc1 | CCOC(=O)C=[N+]=[N-] | null | Cn1ccnc1 | 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 | A toluene (2 ml) solution of 5-isopropenyl-2-(trifluoromethyl)pyridine (219 mg, 1.17 mmol), Co(TPP) (26 mg, 0.039 mmol) and 1-methyl-1H-imidazole (320 mg, 3.9 mmol), ethyl diazoacetate (208 mg, 1.8 mmol) were treated in the same procedure as described in Example 2H. The crude residue (201 mg, 63% yield of the title com... | CCOC(=O)C1CC1(C)c1ccc(C(F)(F)F)nc1 | null | 62.9 | null |
1,169,488 | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | null | 2012-01-01T00:05:00 | true | C(OC([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([CH2:34][C:35]([O:37][CH3:38])=[O:36])[CH:13]=[CH:14][C:15]=1[O:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:33])[C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=2)=[CH:19][CH:18]=1)=O)(C)(C)C.Cl>>[NH2:8][CH2:9][C:10]1[CH:11]=[C:12]([CH2:34][C:35]([O:37][CH3:38])... | COC(=O)Cc1ccc(Oc2ccc(NC(=O)c3ccc(Cl)c(Cl)c3)cc2)c(CNC(=O)OC(C)(C)C)c1 | 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 | null | 3 | Methyl 2-(3-((tert-butoxycarbonyl)aminomethyl)-4-(4-(3,4-dichlorobenzamido)phenoxy)phenyl)acetate (130 mg, 0.232 mmol) was treated with HCl (0.581 mL, 2.32 mmol), After stirring for 3 hours, the material was concentrated to yield 100 mg of methyl 2-(3-(aminomethyl)-4-(4-(3,4-dichlorobenzamido)phenoxy)phenyl)acetate. | COC(=O)Cc1ccc(Oc2ccc(NC(=O)c3ccc(Cl)c(Cl)c3)cc2)c(CN)c1 | null | 93.8 | null |
166,192 | ord_dataset-5c25f386f4664070a72d578feacedf86 | null | 1987-01-01T00:12:00 | true | [NH2:1][C:2]1[O:3][C:4]([C:7](=O)[C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=2)=[CH:5][N:6]=1.[CH3:17][NH:18][CH3:19]>C(O)(C)(C)C>[Cl:15][C:10]1[CH:9]=[C:8]([C:7]2[C:4]([OH:3])=[CH:5][N:6]=[C:2]([N:18]([CH3:19])[CH3:17])[N:1]=2)[CH:13]=[CH:12][C:11]=1[Cl:14] | Nc1ncc(C(=O)c2ccc(Cl)c(Cl)c2)o1 | CNC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)(C)O | null | null | null | null | null | null | null | null | null | null | 25 | 4 | 2-Amino-5-(3', 4'-dichlorobenzoyl)oxazole (2 g, 7.8 mmol) was combined with aqueous dimethylamine (100 ml) in t-butyl alcohol and stirred at room temperature for 4 hours. The solvents were removed in vacuum and the residue was chromatographed on silica gel with hexane and ethylacetate (3:1) as the eluent to yield 1.5 g... | CN(C)c1ncc(O)c(-c2ccc(Cl)c(Cl)c2)n1 | null | null | null |
248,968 | ord_dataset-4f3b2ca6df1d41ef8b5008f1f39da0e2 | null | 1992-01-01T00:06:00 | true | [C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[CH2:9][CH:8]([C:14]3[N:19]=[CH:18][C:17]([C:20]([O:22][CH3:23])=[O:21])=[CH:16][CH:15]=3)[C:7]=2[CH:24]=1)#[N:2].ClC1C=CC=C(C(OO)=[O:33])C=1>ClCCl>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[CH2:9][CH:8]([C:14]3[CH:15]=[CH:16][C:17]([C:... | COC(=O)c1ccc(C2CC(C)(C)Oc3ccc(C#N)cc32)nc1 | O=C(OO)c1cccc(Cl)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 8 | 237 mg of methyl 6-(6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)-3-pyridinecarboxylate were dissolved in 30 ml of dichloromethane and 180 mg of m-chloroperbenzoic acid were added. The mixture was stirred at room temperature overnight and then washed in succession with sodium bisulphite solution, sodium bicarb... | COC(=O)c1ccc(C2CC(C)(C)Oc3ccc(C#N)cc32)[n+]([O-])c1 | null | 24.1 | null |
486,293 | ord_dataset-7b02d32cc502407f94aea8e5caf405a2 | null | 2000-01-01T00:12:00 | true | [OH:1][C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1.N1C=CN=C1.[Si:21](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]>CN(C=O)C.CN(C1C=CN=CC=1)C>[O:1]([C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1)[Si:21... | Oc1ccc2c(c1)Cc1ccccc1O2 | CC(C)(C)[Si](C)(C)Cl | null | CN(C)c1ccncc1 | c1c[nH]cn1 | 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 | 16 | A solution of 2-hydroxy-9H-xanthene 3 (2.63 g, 13.28 mmole) in DMF (15 ml) was added imidazole (1.36 g, 19.9 mmole), t-butyldimethylsilyl chloride (2.4 g, 15.92 mmole) and DMAP (15 mg) successively at room temperature. The mixture was allowed to stir overnight (16 hrs) and quenched with saturated NaHCO3 solution. The a... | CC(C)(C)[Si](C)(C)Oc1ccc2c(c1)Cc1ccccc1O2 | null | 79.5 | null |
1,367,682 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | [C:1]([CH:4]1[C:9](=[O:10])[CH2:8][CH:7]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)[CH2:6][C:5]1=O)(=O)[CH3:2].[NH2:17][C:18]1[N:27]=C(C)C2C(=O)CC(C3C=CC(F)=CC=3)CC=2[N:19]=1>>[NH2:27][C:18]1[N:19]=[C:1]([CH3:2])[C:4]2[C:9](=[O:10])[CH2:8][CH:7]([C:11]3[S:12][CH:13]=[CH:14][CH:15]=3)[CH2:6][C:5]=2[N:17]=1 | Cc1nc(N)nc2c1C(=O)CC(c1ccc(F)cc1)C2 | CC(=O)C1C(=O)CC(c2cccs2)CC1=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from 2-acetyl-5-thien-2-yl-cyclohexane-1,3-dione (430 mg, 1.82 mmol), from stage 1, following the procedure describing the synthesis of 2-amino-7-(4-fluoro-phenyl)-4-methyl-7,8-dihydro-6H-quinazolin-5-one. | Cc1nc(N)nc2c1C(=O)CC(c1cccs1)C2 | null | null | null |
1,180,371 | ord_dataset-0f9d2dbe929a45c3892ae75e81e99443 | null | 2012-01-01T00:06:00 | true | [Br:1][C:2]1[CH:3]=[C:4]([C:11](=O)[CH3:12])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[C:14]([S@:18]([NH2:20])=[O:19])([CH3:17])([CH3:16])[CH3:15]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4](/[C:11](=[N:20]/[S:18]([C:14]([CH3:17])([CH3:16])[CH3:15])=[O:19])/[CH3:12])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1 | CC(=O)c1cc(Br)cc([N+](=O)[O-])c1 | CC(C)(C)[S@](N)=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | 1-(3-Bromo-5-nitro-phenyl)-ethanone (11.6 g, 47.5 mmol), (R)-(+)-tert-butanesulfinamide (6.34 g, 52.3 mmol) and Ti(OEt)4 (24.64 ml, 119 mmol) were mixed in 62 ml THF and refluxed for 2.5 hrs. The reaction was cooled and carefully quenched by addition of ice and water. The white precipitate was filtered off and the aque... | C/C(=N\S(=O)C(C)(C)C)c1cc(Br)cc([N+](=O)[O-])c1 | null | null | null |
1,483,504 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | C(OC([NH:8][C@H:9]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:10]([OH:12])=[O:11])=O)(C)(C)C.S(Cl)(Cl)=O.[CH3:21]O>>[CH3:21][O:12][C:10](=[O:11])[C@H:9]([NH2:8])[CH2:13][CH:14]([CH3:16])[CH3:15] | CC(C)C[C@@H](NC(=O)OC(C)(C)C)C(=O)O | CO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=S(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 25 | null | To a solution of (R)-2-tert-butoxycarbonylamino-4-methyl-pentanoic acid (2 g, 8.7 mmol) in methanol (20 mL) is added thionyl chloride (2.59 g, 21.7 mmol). The reaction mixture is refluxed for 2 h. The reaction mixture is cooled to room temperature and concentrated in vacuo. The crude product is carried on without any f... | COC(=O)[C@H](N)CC(C)C | null | null | null |
525,647 | ord_dataset-293186f5c9b441cab57f03cd3a18ac26 | null | 2001-01-01T00:11:00 | true | F[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19][CH3:20])=[CH:15][CH:14]=3)=[CH:11][C:10]([NH2:21])=[N:9]2)=[CH:4][C:3]=1[CH3:22].Cl[C:24]1C=CC(N2C(C3C=CC(SC)=CC=3)=CC(N)=N2)=C[C:25]=1C>>[CH:3]([C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:14]=[CH:15][C:16]([S:19][CH3:20])=[CH:17][CH:18]=3)... | CSc1ccc(-c2cc(N)nn2-c2ccc(F)c(C)c2)cc1 | CSc1ccc(-c2cc(N)nn2-c2ccc(Cl)c(C)c2)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 following compounds described in (1) to (2) were obtained according to a similar manner to that of Preparation 3. | CSc1ccc(-c2cc(N)nn2-c2ccc(C(C)C)cc2)cc1 | null | null | null |
348,650 | ord_dataset-66f304805e5d47fc8d3c722b1bd8dfa2 | null | 1996-01-01T00:12:00 | true | [C:1]1([S:7]([NH2:10])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:11]1([O:16][C:17]([NH:19][C:20]2[CH:21]=[CH:22][C:23]3[O:28][CH2:27][CH2:26][N:25]([CH2:29][C:30]4[CH:38]=[CH:37][C:33]([C:34](O)=[O:35])=[CH:32][C:31]=4[O:39][CH3:40])[C:24]=3[CH:41]=2)=[O:18])[CH2:15][CH2:14][CH2:13][CH2:12]1.Cl.CN(C)CCCN=C=N... | COc1cc(C(=O)O)ccc1CN1CCOc2ccc(NC(=O)OC3CCCC3)cc21 | NS(=O)(=O)c1ccccc1 | null | CCN=C=NCCCN(C)C | CN(C)c1ccncc1 | 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 | 21 | Benzenesulphonamide (0.037 g.) was added to a stirred solution of 4-[6-(cyclopentyloxycarbonyl)amino-2,3-dihydrobenz-1,4-oxazin-4-ylmethyl]-3-methoxybenzoic acid (0.1 g.), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.046 g.) and 4-(dimethylamino)pyridine (0.029 g.) in dichloromethane (5 ml.), under an... | COc1cc(C(=O)NS(=O)(=O)c2ccccc2)ccc1CN1CCOc2ccc(NC(=O)OC3CCCC3)cc21 | null | 53.5 | null |
439,798 | ord_dataset-3e8f24b5bc8e4d8bb9b6e7e89a956e12 | null | 1999-01-01T00:09:00 | true | [C:1]([C:6](=[CH:12][NH:13][C:14]1[C:15]([O:20][CH3:21])=[N:16][CH:17]=[CH:18][CH:19]=1)[C:7]([O:9]CC)=O)(=[O:5])[CH2:2][CH2:3][CH3:4]>C1(OC2C=CC=CC=2)C=CC=CC=1>[C:1]([C:6]1[C:7](=[O:9])[C:19]2[C:14](=[C:15]([O:20][CH3:21])[N:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)(=[O:5])[CH2:2][CH2:3][CH3:4] | CCCC(=O)C(=CNc1cccnc1OC)C(=O)OCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccc(Oc2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | 50 | null | 11.23 g of ethyl 2-butyryl-3-(2-methoxypyridine-3-yl)aminoacrylate prepared in the above (A) was dissolved in 60 ml so diphenyl ether, and the resulting solution was heated to reflux for 2 hours and cooled to about 50° C. Petroleum ether (200 ml) was added to give precipitates, which were filtered to give 6.3 g (76%) o... | CCCC(=O)c1c[nH]c2c(OC)nccc2c1=O | null | 66.6 | null |
960,865 | ord_dataset-ed65749688da45af8a8432967b017729 | null | 2010-01-01T00:05:00 | true | [CH3:1][O:2][C:3](=[O:23])[C:4]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)=[CH:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[C:8]([O:14][CH3:15])[CH:7]=1.[H-].[Na+].F[C:27]1[CH:34]=[CH:33][C:30]([CH:31]=[O:32])=[CH:29][CH:28]=1>CN(C=O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:23])[C:4]([C:16]1[CH:17]=[CH:18][C:1... | O=Cc1ccc(F)cc1 | COC(=O)C(=Cc1cc(OC)cc(OC)c1)c1ccc(O)cc1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 80 | 8 | Under argon, 8 (433.0 g, 1.37 mol) was dissolved in dry DMF (1.6 L) and to this sodium hydride (60.4 g, 1.51 mol) was added. To the resulting orange solution 4-fluorobenzaldehyde (185.0 mL, 1.71 mol) was added and heated at 80° C. for 18 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate... | COC(=O)C(=Cc1cc(OC)cc(OC)c1)c1ccc(Oc2ccc(C=O)cc2)cc1 | null | 77.6 | null |
1,367,895 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | [Cl:1][C:2]1[C:9]([Cl:10])=[C:8](F)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH3:12][C@H:13]1[C@@H:17]([OH:18])[CH2:16][CH2:15][NH:14]1>CS(C)=O.C(=O)([O-])[O-].[Li+].[Li+]>[Cl:1][C:2]1[C:9]([Cl:10])=[C:8]([N:14]2[CH2:15][CH2:16][C@H:17]([OH:18])[C@@H:13]2[CH3:12])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5] | N#Cc1ccc(F)c(Cl)c1Cl | C[C@@H]1NCC[C@@H]1O | null | O=C([O-])[O-] | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | Using 2,3-dichloro-4-fluorobenzonitrile (400.5 mg), 0.9 mol/L solution (2.35 mL) of (2S,3S)-2-methylpyrrolidin-3-ol in dimethyl sulfoxide and lithium carbonate (78 mg), the title compound was obtained as yellow crystals (yield: 417 mg) by an operation similar to that in Example 3. | C[C@H]1[C@@H](O)CCN1c1ccc(C#N)c(Cl)c1Cl | null | null | null |
1,509,718 | ord_dataset-1a1aa5d1c3224edca0aec6e3398da985 | null | 2014-01-01T00:11:00 | true | ClC(Cl)(Cl)[C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:23])=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH3:22])=[CH:16][CH:15]=3)[CH:12]=2)[NH:7][CH:6]=1)=[O:4].[OH-:26].[K+]>COCCOC>[Cl:23][C:10]1[CH:9]=[C:8]2[C:13]([C:5]([C:3]([OH:26])=[O:4])=[CH:6][NH:7]2)=[CH:12][C:11]=1[C:14]1[CH:15]=[CH:16][C:17]([O:20][CH2... | [OH-] | CCOc1ccc(-c2cc3c(C(=O)C(Cl)(Cl)Cl)c[nH]c3cc2Cl)cc1 | null | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COCCOC | null | null | null | null | null | null | null | null | null | null | 25 | 12 | To a solution of 2,2,2-trichloro-1-(6-chloro-5-(4-ethoxyphenyl)-1H-indol-3-yl)ethanone (70.0 mg, 0.17 mmol) in DME (1 mL) was added 1N KOH (0.71 mmol, 0.71 mL). The reaction mixture was stirred at room temperature for 12 hours, and concentrated in vacuo. The crude material was diluted with water (5 mL), and acidified t... | CCOc1ccc(-c2cc3c(C(=O)O)c[nH]c3cc2Cl)cc1 | null | 68.9 | null |
1,066,725 | ord_dataset-ffbef48837674f39816de887b5dc8bae | null | 2011-01-01T00:06:00 | true | C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]2[CH:16]=[C:17]3[C:21](=[C:22]([Cl:24])[CH:23]=2)[C:20](=[O:25])[N:19]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][C:34]([F:37])([F:36])[F:35])=[CH:29][CH:28]=2)[CH2:18]3)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:24][C:22]1[CH:23]=[C:15]([CH2:14][CH:11]2[CH2:1... | CC(C)(C)OC(=O)N1CCC(Cc2cc(Cl)c3c(c2)CN(Cc2ccc(OC(F)(F)F)cc2)C3=O)CC1 | 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 | null | null | 4-[7-Chloro-1-oxo-2-(4-trifluoromethoxybenzyl)-2,3-dihydro-1H-isoindol-5-ylmethyl]-piperidine-1-carboxylic acid tert-butyl ester (54.90 mg, 0.102 mmol) was stirred in dichloromethane (2 mL) and trifluoroacetic acid (2 mL) overnight. The reaction mixture was quenched with sodium carbonate to pH=8-9 and the free base was... | O=C1c2c(Cl)cc(CC3CCNCC3)cc2CN1Cc1ccc(OC(F)(F)F)cc1 | null | 109.2 | null |
1,328,755 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | [N:1]([C:4]1[CH:5]=[CH:6][C:7]([CH3:10])=[N:8][CH:9]=1)=[C:2]=[O:3].C([O-])(O)=O.[Na+].[NH2:16][C:17]1[CH:18]=[C:19]([CH:35]=[CH:36][CH:37]=1)[CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]1>CCOC(C)=O>[CH3:10][C:7]1[N:8]=[CH:9][C:4]([NH:1][C:2](=[O:... | CC(C)(C)OC(=O)N1CCN(CCc2cccc(N)c2)CC1 | Cc1ccc(N=C=O)cn1 | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | 2 | To a solution of tert-butyl 4-(3-aminophenethyl)piperazine-1-carboxylate (7D, 1.0 eq) in THF (about 0.3 M 7D in THF) was added 5-isocyanato-2-methylpyridine (1.0 eq) dropwise. The resulting reaction mixture was stirred for 2 h. To the reaction mixture was added saturated aq. NaHCO3. The mixture was diluted with EtOAc, ... | Cc1ccc(NC(=O)Nc2cccc(CCN3CCN(C(=O)OC(C)(C)C)CC3)c2)cn1 | null | 63 | null |
1,484,898 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [N+:1]([C:4]1[CH:34]=[CH:33][C:7]([O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][O:28]2)=[CH:6][CH:5]=1)([O-])=O>[Pd]>[O:28]1[CH2:29][CH2:30][CH2:31][CH2:32][CH:27]1[O:26][CH2:25][CH2:24][O:... | O=[N+]([O-])c1ccc(OCCOCCOCCOCCOCCOCCOC2CCCCO2)cc1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 16 | To a stirred solution of 35 (6.30 g, 12.9 mmol) in 1:1 THF/TEA (26 mL) in a Parr apparatus was added a catalytic amount of 20% Pd/C (0.05 g). The reaction vessel was purged with hydrogen then pressurized to 70 psi. After stirring for 16 h the reaction mixture was filtered through a 4 cm pad of celite and concentrated u... | Nc1ccc(OCCOCCOCCOCCOCCOCCOC2CCCCO2)cc1 | null | 98.3 | null |
1,704,940 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | [CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[CH:9][C:10]([C:25]([O:27]C)=O)=[C:11]3[C:16]=2[O:15][CH2:14][CH:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:12]3[N:23]=O)=[C:5]([CH3:29])[O:4][N:3]=1.[Cl-].[NH4+]>C(OCC)(=O)C.CO.[Zn]>[CH3:1][C:2]1[C:6]([C:7]2[C:16]3[O:15][CH2:14][CH:13]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH... | COC(=O)c1ccc(-c2c(C)noc2C)c2c1N(N=O)C(c1ccccc1)CO2 | null | null | [Cl-] | [NH4+] | [Zn] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CO | null | null | null | null | null | null | null | null | null | null | 2 | A suspension of methyl 8-(3,5-dimethylisoxazol-4-yl)-4-nitroso-3-phenyl-3,4-dihydro-2H-1,4-benzoxazine-5-carboxylate (0.228 g, 0.580 mmol) in ethyl acetate (4.04 mL) and methanol (4.04 mL) at 0° C. was treated with saturated aqueous ammonium chloride solution (2.02 mL, 30.2 mmol) and then zinc (0.303 g, 4.64 mmol) was ... | Cc1noc(C)c1-c1ccc2c(=O)[nH]n3c2c1OCC3c1ccccc1 | null | 69.5 | null |
946,077 | ord_dataset-ed680843f6d14f5c9901869b2a06b4a4 | null | 2010-01-01T00:03:00 | true | [OH-].[Na+].[CH3:3][C:4]1([CH3:35])[C:13]2[N:12]=[C:11]([CH2:14][O:15][C:16]3[CH:21]=[CH:20][C:19]([C@@H:22]([C:29]4[N:30]([CH3:34])[CH:31]=[CH:32][N:33]=4)[CH2:23][C:24]([O:26]CC)=[O:25])=[CH:18][CH:17]=3)[CH:10]=[CH:9][C:8]=2[CH2:7][CH2:6][CH2:5]1.Cl>CCO>[CH3:3][C:4]1([CH3:35])[C:13]2[N:12]=[C:11]([CH2:14][O:15][C:16... | CCOC(=O)C[C@@H](c1ccc(OCc2ccc3c(n2)C(C)(C)CCC3)cc1)c1nccn1C | null | null | Cl | [Na+] | [OH-] | 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 | 4 | 10% NaOH (aq) (1 mL) is added to a solution of compound 54.1 (45 mg, 0.1 mmol) in EtOH (2 mL). The reaction mixture is stirred at room temperature for 4 hours. 1N HCl is added to neutralize the mixture to pH 6-7. The mixture is extracted with EtOAc (2×20 mL), washed with water and brine, dried over Na2SO4, filtered and... | Cn1ccnc1[C@@H](CC(=O)O)c1ccc(OCc2ccc3c(n2)C(C)(C)CCC3)cc1 | null | null | null |
1,211,712 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | [C:1]1(=[O:8])[O:7][C:5](=[O:6])[CH2:4][C:2]1=[CH2:3].[CH2:9]([OH:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1(C)C=CC=CC=1>[CH2:9]([O:16][C:5]([CH2:4][C:2](=[CH2:3])[C:1]([OH:8])=[O:7])=[O:6])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1 | OCc1ccccc1 | C=C1CC(=O)OC1=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | 25 | 8 | To a solution of itaconic anhydride (33.6 g, 0.3 mol) in 100 ml of toluene is added benzyl alcohol (32.4 g, 0.3 mol). The resulting solution is heated to reflux for 3 hours. After cooling down to room temperature, hexanes (100 mL) are added to the above mixture and are continued to stir for 8 hours. A white solid is co... | C=C(CC(=O)OCc1ccccc1)C(=O)O | null | 83.2 | null |
1,057,870 | ord_dataset-373415d3e0e54004837cf4831e67666f | null | 2011-01-01T00:05:00 | true | [O:1]=[C:2]([C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)[C:3](O)=[O:4].C(Cl)(=O)C([Cl:14])=O.CN(C=O)C>C(Cl)Cl>[O:1]=[C:2]([C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)[C:3]([Cl:14])=[O:4] | O=C(Cl)C(=O)Cl | O=C(O)C(=O)c1cccs1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CN(C)C=O | null | null | null | null | null | null | null | null | null | 5 | 18 | To a solution of oxo-thiophen-2-yl-acetic acid (8 g, 51.2 mmol), suspended in DCM (80 ml) and cooled to 5° C., is added oxalylchloride (5.3 ml, 61.5 mmol), followed by DMF (0.1 ml). Stirring is continued for 1 hour at 5° C. and 18 hours at room temperature. The reaction mixture is evaporated to dryness, toluene is then... | O=C(Cl)C(=O)c1cccs1 | null | null | null |
705,602 | ord_dataset-c408dfed796e4354b61e312e67f7143f | null | 2006-01-01T00:04:00 | true | [NH2:1][C:2]1[NH:6][N:5]=[C:4]([CH:7]2[CH2:10][CH2:9]C2)[CH:3]=1.ClC(Cl)(Cl)[C:13]([C:15]1[NH:16][CH:17]=[CH:18][CH:19]=1)=[O:14].C(N(CC)CC)C>C(#N)C>[CH:7]1([C:4]2[CH:3]=[C:2]([NH:1][C:13]([C:15]3[NH:16][CH:17]=[CH:18][CH:19]=3)=[O:14])[NH:6][N:5]=2)[CH2:10][CH2:9]1 | Nc1cc(C2CCC2)n[nH]1 | O=C(c1ccc[nH]1)C(Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | null | To 260 mg (1.9 mmol) of 5-amino-3-cyclobutylpyrazole in 7 mL of acetonitrile was added 407 mg (1.9 mmol) of 2-trichloroacetylpyrrole and 220 μL of triethylamine. The mixture was stirred and heated at reflux, under nitrogen, for 12 hours. TLC analysis showed some starting material still remained. The mixture was concent... | O=C(Nc1cc(C2CC2)n[nH]1)c1ccc[nH]1 | null | 45.8 | null |
104,355 | ord_dataset-b2a00a09c8494aaf9348c3a3af29d26e | null | 1983-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH:6]=[CH:7][C:8](=[O:13])[C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:4][CH:3]=1.[C:16]1([SH:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(N(CC)CC)C.C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]([S:22][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:7][C:8](=[O:13])[C:9]([CH3:10])([CH3:11]... | Sc1ccccc1 | CC(C)(C)C(=O)C=Cc1ccc(Cl)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | 4 | To a mixture of 4-chlorobenzalpinacolone (22.3 g), triethylamine (5 drops) and ethanol (250 ml) was added thiophenol (12 g) and the mixture was kept to 70° C. for 4 hours. After ice-cooling, the resulted precipitates were collected by filtration, washed with cold ethanol and dried to give white crystals of the captione... | CC(C)(C)C(=O)CC(Sc1ccccc1)c1ccc(Cl)cc1 | null | null | null |
891,585 | ord_dataset-11068b1e475b4c5b82e56726ab0dddb7 | null | 2009-01-01T00:07:00 | true | [F:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:14]([C:15]([OH:17])=O)=[C:13]([CH3:18])[NH:12][C:11](=[O:19])[NH:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1.[F:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28]2[C:36]3[C:31](=[CH:32][CH:33]=[C:34]([NH2:37])[CH:35]=3)[NH:30][N:29]=2)=[CH:23][CH:22]=1.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(... | CC1=C(C(=O)O)C(c2cc(F)cc(F)c2)NC(=O)N1 | Nc1ccc2[nH]nc(Nc3ccc(F)cc3)c2c1 | null | Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1 | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | ClCCl | null | null | null | null | null | null | null | null | null | null | null | The titled compound was prepared following the procedure of Example 175 using 4-(3,5-Difluoro-phenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid, N3-(4-fluoro-phenyl)-1H-indazole-3,5-diamine, PyBroP and diisopropylethylamine in methylene chloride. MS (ESI) m/z=493 [M+H]+. | CC1=C(C(=O)Nc2ccc3[nH]nc(Nc4ccc(F)cc4)c3c2)C(c2cc(F)cc(F)c2)NC(=O)N1 | null | null | null |
685,896 | ord_dataset-359b8fc87f4244be89d6f02bc5036eac | null | 2005-01-01T00:09:00 | true | C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][C:9]=1[NH:18][C:19](=[O:39])[CH2:20][C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C:29]2[CH:30]=[N:31][C:32]([CH:36]3[CH2:38][CH2:37]3)=[CH:33][C:34]=2[CH3:35])[CH:24]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:36]1([C:32]2[N:31]=[CH:30][C:29... | Cc1cc(C2CC2)ncc1-c1cccc(C(=O)CC(=O)Nc2cc(C(F)(F)F)ccc2NC(=O)OC(C)(C)C)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from (2-{3-[3-(6-cyclopropyl-4-methyl-pyridin-3-yl)-phenyl]-3-oxo-propionylamino}-4-trifluoromethyl-phenyl)-carbamic acid tert-butyl ester (Example M264) (260 mg, 0.47 mmol) by treatment with TFA in CH2Cl2 according to the general procedure N. Obtained as an off-white solid (67 mg, 33%). | Cc1cc(C2CC2)ncc1-c1cccc(C2=Nc3ccc(C(F)(F)F)cc3NC(=O)C2)c1 | null | null | null |
1,462,889 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | [F:1][C:2]([F:26])([F:25])[C:3]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:4]=1[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([CH:15]=O)=[CH:12][CH:13]=2)[CH:8]=[N:7]1.[O:27]=[C:28]1[N:32]([C@@H:33]2[CH2:38][CH2:37][N:36](C(OC(C)(C)C)=O)[CH2:35][C@H:34]2[F:46])[C:31](=[O:47])[CH2:30][S:29]1>>[F:26][C:2]([F... | CC(C)(C)OC(=O)N1CC[C@@H](N2C(=O)CSC2=O)[C@H](F)C1 | O=Cc1ccc2c(cnn2Cc2ccc(C(F)(F)F)cc2C(F)(F)F)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | (5Z)-5-({1-[2,4-Bis(trifluoromethyl)benzyl]-1H-indazol-5-yl}methylidene)-3-[trans-3-fluoropiperidin-4-yl]-1,3-thiazolidine-2,4-dione was prepared from [2,4-bis(trifluoromethyl)benzyl]-1H-indazol-5-carbaldehyde (from Example 6) and 1,1-dimethylethyl trans-4-(2,4-dioxo-1,3-thiazolidin-3-yl)-3-fluoropiperidine-1-carboxyla... | O=C1S/C(=C\c2ccc3c(cnn3Cc3ccc(C(F)(F)F)cc3C(F)(F)F)c2)C(=O)N1[C@@H]1CCNC[C@H]1F | null | null | null |
1,142,401 | ord_dataset-68715347640045adb1b09e6a04722b0e | null | 2012-01-01T00:03:00 | true | [Br:1][C:2]1[C:3]([F:11])=[C:4]([C:7]([OH:10])=[CH:8][CH:9]=1)[CH:5]=[O:6].[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22]([O:10][C:7]2[CH:8]=[CH:9][C:... | Cc1ccc(S(=O)(=O)OC2CCN(C(=O)OC(C)(C)C)CC2)cc1 | O=Cc1c(O)ccc(Br)c1F | 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 | null | null | In a manner similar to the method described in example 4a, 3-bromo-2-fluoro-6-hydroxy-benzaldehyde (3.69 g, 16.8 mmol) reacted with 4-(toluene-4-sulfonyloxy)-piperidine-1-carboxylic acid tert-butyl ester (4 g, 11.2 mmol, ASTATECH) and K2CO3 in N,N-dimethylformamide to give 4-(4-bromo-3-fluoro-2-formyl-phenoxy)-piperidi... | CC(C)(C)OC(=O)N1CCC(Oc2ccc(Br)c(F)c2C=O)CC1 | null | 93.9 | null |
753,935 | ord_dataset-1b0cd79134f0450eaac8396a4f956c30 | null | 2007-01-01T00:02:00 | true | [C:1]([NH:8][C@H:9]([C:14]([OH:16])=O)[CH2:10][CH2:11][S:12][CH3:13])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[NH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1>>[C:1]([NH:8][C@H:9]([C:14]([N:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:16])[CH2:10][CH2:11][S:12][CH3:13])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2] | CSCC[C@H](NC(=O)OC(C)(C)C)C(=O)O | C1CCNC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 2.50 g (10 mmol) BOC-methionine was coupled to 1.72 ml (20.6 mmol) pyrrolidine according to procedure B. Yield of crude product 3.38 g. The product was purified with a silica column using ethyl acetate as eluent. Yield 2.81 g (9.3 mmol, 93%). | CSCC[C@H](NC(=O)OC(C)(C)C)C(=O)N1CCCC1 | null | null | null |
200,625 | ord_dataset-31f00a039ca0424788e5e1970d25a8fd | null | 1989-01-01T00:12:00 | true | [C:1]([O:14][CH2:15][C:16]([CH3:20])([CH3:19])[CH:17]=[O:18])(=[O:13])/[CH:2]=[CH:3]\[C:4]([O:6][CH2:7][C:8]([CH3:12])([CH3:11])[CH:9]=[O:10])=[O:5].N1CCOCC1>C1(C)C=CC=CC=1>[C:1]([O:14][CH2:15][C:16]([CH3:20])([CH3:19])[CH:17]=[O:18])(=[O:13])/[CH:2]=[CH:3]/[C:4]([O:6][CH2:7][C:8]([CH3:11])([CH3:12])[CH:9]=[O:10])=[O:5... | CC(C)(C=O)COC(=O)/C=C\C(=O)OCC(C)(C)C=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | C1COCCN1 | null | null | null | null | null | null | null | null | null | 25 | null | Crude bis (2,2-dimethyl-3-oxopropyl) maleate was treated with a catalytic amount of morpholine (10 wt. %) in refluxing toluene for 4 hrs. The resulting solution was cooled to room temperature, washed with diluted hydrochloric acid and brine, then dried over magnesium sulfate. Evaporation of volatiles in vacuo gave crud... | CC(C)(C=O)COC(=O)/C=C/C(=O)OCC(C)(C)C=O | null | null | null |
1,749,249 | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | null | 2016-01-01T00:07:00 | true | [CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9].Cl[C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[C:14]([C:21]3[NH:29][C:28]4[CH2:27][CH2:26][NH:25][C:24](=[O:30])[C:23]=4[CH:22]=3)[CH:15]=[CH:16][CH:17]=2)[N:12]=1>>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[O:9][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[C:14... | O=C1NCCc2[nH]c(-c3cccc4ccc(Cl)nc34)cc21 | Cc1cccc(C)c1O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 70 | null | Prepared according to Example 103 using 2,6-dimethylphenol (158 mg, 1.293 mmol) and 2-(2-chloroquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 1; 50.0 mg, 0.168 mmol), heating at 70° C. for 17 h. Chromatographic purification (silica gel, 0-10% MeOH/DCM) furnished 2-(2-(2,6-dimethylphenoxy)quinoli... | Cc1cccc(C)c1Oc1ccc2cccc(-c3cc4c([nH]3)CCNC4=O)c2n1 | null | 79.8 | null |
1,487,506 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [C:1]([O:5][C:6](=[O:22])[NH:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][CH2:20][NH2:21])=[CH:13][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].I.[NH2:24][C:25]1[C:26]([C:33]([NH:35][C:36](=[NH:39])SC)=[O:34])=[N:27][C:28]([Cl:32])=[C:29]([NH2:31])[N:30]=1.C(N(CC)CC)C>C1COCC1>[C:1]([O:5][C:6](=[O:2... | CC(C)(C)OC(=O)NCCOc1ccc(CCCCN)cc1 | CSC(=N)NC(=O)c1nc(Cl)c(N)nc1N | null | I | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | {2-[4-(4-Aminobutyl)phenoxy]ethyl}carbamic acid tert-butyl ester 2 (1.7 g, 5.5 mmol), 1-(3,5-diamino-6-chloropyrazine-2-carbonyl)-2-methylisothiourea hydriodide (2.6 g, 6.6 mmol), and triethylamine (3.1 mL) were combined in THF (18 mL). The reaction was stirred at reflux under argon for 1.5 h. The product mixture was a... | CC(C)(C)OC(=O)NCCOc1ccc(CCCCNC(N)=NC(=O)c2nc(Cl)c(N)nc2N)cc1 | null | 92.5 | null |
1,289,796 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [C:1]1([S:7]([CH2:10][C@@H:11]2[N:16]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([OH:32])([C:28]([F:31])([F:30])[F:29])[C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O.[Cl:47][C:48]1[N:53]=[CH:52][C:51]([S:54](Cl)(... | O=S(=O)(Cl)c1ccc(Cl)nc1 | CC(C)(C)OC(=O)N1CCN(c2ccc(C(O)(C(F)(F)F)C(F)(F)F)cc2)[C@@H](CS(=O)(=O)c2ccccc2)C1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 0.17 | A 20 mL vial was charged with tert-butyl (3R)-3-((phenylsulfonyl)methyl)-4-(4-(2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl)phenyl)-1-piperazinecarboxylate (0.038 g, 0.065 mmol), TFA (0.50 mL, 6.5 mmol, Sigma-Aldrich, St. Louis, Mo.) and DCM (1 mL). The mixture was stirred at rt for 10 min. The volatile was remov... | O=S(=O)(C[C@H]1CN(S(=O)(=O)c2ccc(Cl)nc2)CCN1c1ccc(C(O)(C(F)(F)F)C(F)(F)F)cc1)c1ccccc1 | null | 60.8 | null |
1,569,459 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:15][CH3:16])=[C:6]([C:8]2[N:9]=[C:10]([CH3:14])[S:11][C:12]=2[NH2:13])[CH:7]=1.[N:17]1[N:21]2[CH:22]=[CH:23][CH:24]=[N:25][C:20]2=[C:19]([C:26](Cl)=[O:27])[CH:18]=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:15][CH3:16])=[C:6]([C:8]2[N:9]=[C:10]([CH3:14])[S:11][C:12]=2[NH:13][C:26]([C:19]2[CH:... | O=C(Cl)c1cnn2cccnc12 | COc1ccc(Cl)cc1-c1nc(C)sc1N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Using 4-(5-chloro-2-methoxyphenyl)-2-methylthiazol-5-amine and pyrazolo[1,5-a]pyrimidine-3-carbonyl chloride the title compound was synthesized following the synthetic procedures described for N-(2-(2-(tert-butyldimethylsilyloxy)-2-methylpropyl)-4-(5-chloro-2-methoxyphenyl)thiazol-5-yl)pyrazolo[1,5-a]pyrimidine-3-carbo... | COc1ccc(Cl)cc1-c1nc(C)sc1NC(=O)c1cnn2cccnc12 | null | null | null |
771,576 | ord_dataset-8214eb8444a44dc2900ccb42dbeff15e | null | 2007-01-01T00:05:00 | true | [CH:1]([O:4][C:5]1[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][C:6]=1[C:7]([OH:9])=O)([CH3:3])[CH3:2].[F:18][C:19]([F:32])([F:31])[C:20]1[N:21]=[C:22]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[S:23][CH:24]=1>>[CH:1]([O:4][C:5]1[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][C:6... | FC(F)(F)c1csc(N2CCNCC2)n1 | CC(C)Oc1ccc(S(C)(=O)=O)cc1C(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared in analogy to example 1 (b) from 2-isopropoxy-5-methanesulfonyl-benzoic acid (Example A1) and 1-(4-trifluoromethyl-thiazol-2-yl)-piperazine. The crude material was purified by chromatography (SiO2, ethyl acetate/heptane) followed by trituration in pentane to yield the title compound as a crystalline white soli... | CC(C)Oc1ccc(S(C)(=O)=O)cc1C(=O)N1CCN(c2nc(C(F)(F)F)cs2)CC1 | null | 55 | null |
1,548,235 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | C[O:2][C:3]([C:5]1[NH:9][C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=2[N:6]=1)=[O:4].Cl>[OH-].[Na+].CO>[NH:6]1[C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=[C:5]1[C:3]([OH:4])=[O:2] | COC(=O)c1nc2ccccc2[nH]1 | null | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | 18 | A mixture of 1H-benzoimidazole-2-carboxylic acid methyl ester (18) (0.89 g, 5.1 mmol) in 2 N aq. NaOH (10 mL) and MeOH (10 mL) was stirred at RT for 18 h. The mixture was acidified to pH=4 with 1 N aqueous HCl. The mixture was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and evaporat... | O=C(O)c1nc2ccccc2[nH]1 | null | 81 | null |
1,157,498 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | [N:1]1([CH2:7][C@@H:8]2[CH2:10][C@H:9]2[C:11]([OH:13])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[F:14][CH:15]([F:29])[O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]1[CH:24]=[C:25]([NH2:28])[NH:26][N:27]=1>>[F:29][CH:15]([F:14])[O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]1[CH:24]=[C:25]([NH:28][C:11... | O=C(O)[C@@H]1C[C@H]1CN1CCCCC1 | Nc1cc(-c2ccccc2OC(F)F)n[nH]1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The product was prepared according to the general synthetic method for the synthesis of ω-amino-alkanoic acid (1H-pyrazol-3-yl-5-aryl)-amides via the amino acid route, starting from trans (±)-2-piperidin-1-ylmethyl-cyclopropanecarboxylic acid (99.1 mg, 0.6 mmol, 1.3 eq) and 5-(2-difluoromethoxy-phenyl)-2H-pyrazol-3-yla... | O=C(Nc1cc(-c2ccccc2OC(F)F)n[nH]1)[C@@H]1C[C@H]1CN1CCCCC1 | null | 25.5 | null |
917,414 | ord_dataset-8e59bd24817446f7b1c68e805b8e5f1d | null | 2009-01-01T00:11:00 | true | [F:1][C:2]([F:21])([F:20])[S:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[C:14]([NH2:19])[CH:13]=1)(=[O:5])=[O:4].Cl.C(O[C:26](=N)[CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][CH:30]=1)C>CCO>[F:21][C:2]([F:20])([F:1])[S:3]([C:6]1[CH:11]=[CH:10][C... | CCOC(=N)COc1ccc(C(F)(F)F)cc1 | Nc1ccc(-c2ccccc2S(=O)(=O)C(F)(F)F)cc1N | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 25 | 12 | A mixture of 2′-trifluoromethanesulfonyl-biphenyl-3,4-diamine (0.042 g, 0.133 mmol) and 2-(4-trifluoromethyl-phenoxy)-acetimidic acid ethyl ester hydrochloride (0.045 g, 0.159 mmol, Example 1.1) in EtOH (4 mL) was stirred at room temperature for 12 hours. The reaction was concentrated to give a residue, which was purif... | O=S(=O)(c1ccccc1-c1ccc2[nH]c(COc3ccc(C(F)(F)F)cc3)nc2c1)C(F)(F)F | null | 97.7 | null |
615,969 | ord_dataset-31fc6d0085ca4d8dbbcd3a5fa9dcedfb | null | 2003-01-01T00:11:00 | true | C[O:2][C:3](=[O:39])[C@H:4]([NH:11][C:12]([C:14]12[CH2:21][C:18]([C:22]3[NH:30][C:29]4[C:28](=[O:31])[N:27]([CH2:32][CH2:33][CH3:34])[C:26](=[O:35])[N:25]([CH2:36][CH2:37][CH3:38])[C:24]=4[N:23]=3)([CH2:19][CH2:20]1)[CH2:17][CH2:16][CH2:15]2)=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Li+].[OH-]>C1COCC1>[O:35]=[... | CCCn1c(=O)c2[nH]c(C34CCCC(C(=O)N[C@@H](C(=O)OC)c5ccccc5)(CC3)C4)nc2n(CCC)c1=O | null | null | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | A solution of (1RS,2R,5SR)-{[5-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo-[3.2.1]octane-1-carbonyl]-amino}-phenyl-acetic acid methyl ester (0.022 mmol, 0.012 g) in THF (2 ml) was treated with 1N LiOH (0.22 ml) for 3d. The THF was removed on the rotovap, the aqueous residue acidified (pH 2) with 1... | CCCn1c(=O)c2[nH]c(C34CCCC(C(=O)N[C@@H](C(=O)O)c5ccccc5)(CC3)C4)nc2n(CCC)c1=O | null | 47.9 | null |
1,186,933 | ord_dataset-9cd817a75dfc4fe7ad19d4232772d5ff | null | 2012-01-01T00:07:00 | true | [Br:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13].CO.[CH2:17]1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:17][O:8][C:7](=[O:9])[C:6]1[CH:10]=[CH:11][C:3]([CH2:2][Br:1])=[C:4]([N+:12]([O-:14])=[O:13])[CH:5]=1 | O=C(O)c1ccc(CBr)c([N+](=O)[O-])c1 | C(=NC1CCCCC1)=NC1CCCCC1 | null | CN(C)c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CO | null | null | null | null | null | null | null | null | null | 25 | 2 | To a solution of 4-bromomethyl-3-nitrobenzoic acid (2.6 g, 10 mmol), MeOH (320 mg, 10 mmol) and DMAP (122 mg, 1 mmol) in methylene chloride (40 mL) was added DCC (2.06 g, 10 mmol) and the resulting mixture was stirred at ambient temperature for 2 h. The resulting precipitate was filtered and the filtrate evaporated und... | COC(=O)c1ccc(CBr)c([N+](=O)[O-])c1 | null | null | null |
802,439 | ord_dataset-ed846b4b229e4bb09ad9dba95ad7ebeb | null | 2008-01-01T00:01:00 | true | [NH:1]1[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1.C[Al](C)C.[F:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:13]=1[N:19]1[C:24]2[N:25]=[C:26]([NH:37][CH2:38][C:39](OC)=[O:40])[N:27]=[C:28]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][C:30]=3[CH3:36])[C:23]=2[CH:22]=[CH:21][C:20]1=[O:43]>>[F:11][C:12]1[CH:17]=[CH:16][CH:15]... | COC(=O)CNc1nc(-c2ccc(F)cc2C)c2ccc(=O)n(-c3c(F)cccc3F)c2n1 | C1CSCCN1 | null | C[Al](C)C | null | null | null | null | null | 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 procedure outlined in Example 193, thiomorpholine (0.22 mL, 2.2 mmol), trimethylaluminum (1.1 mL, 2.2 mmol) and the product of Example 190 (200 mg, 0.44 mmol) were reacted to give the desired product 200 mg (86%). LC-MS: 526.0 (MH+, m/z), 2.07 (Rt, min). | Cc1cc(F)ccc1-c1nc(NCC(=O)N2CCSCC2)nc2c1ccc(=O)n2-c1c(F)cccc1F | null | 86.5 | null |
1,536,124 | ord_dataset-8d5c200bca27407ab9febe7598e16458 | null | 2015-01-01T00:01:00 | true | [NH2:1][C:2]1[CH:3]=[C:4]([C:8]([NH:10][C@@:11]2([C:16]([O:18]CCCC)=[O:17])[CH2:15][CH2:14][O:13][CH2:12]2)=[O:9])[CH:5]=[N:6][CH:7]=1.[OH-].[Na+]>>[NH2:1][C:2]1[CH:3]=[C:4]([C:8]([NH:10][C@@:11]2([C:16]([OH:18])=[O:17])[CH2:15][CH2:14][O:13][CH2:12]2)=[O:9])[CH:5]=[N:6][CH:7]=1 | CCCCOC(=O)[C@]1(NC(=O)c2cncc(N)c2)CCOC1 | null | null | [Na+] | [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 | Analogously to Example 1d), n-butyl(S)-3-[(5-amino-pyridine-3-carbonyl)-amino]-tetrahydrofuran-3-carboxylate (69.9 mmol) was saponified with sodium hydroxide solution. | Nc1cncc(C(=O)N[C@@]2(C(=O)O)CCOC2)c1 | null | null | null |
499,594 | ord_dataset-18e9ed24dbd44e98b33bdc22aa7580a8 | null | 2001-01-01T00:04:00 | true | [C:1]1([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH:6]=[CH:5][C:4]([OH:7])=[CH:3][CH:2]=1>C1(C)C=CC=CC=1.[Pd]>[CH:8]1([CH:1]2[CH2:2][CH2:3][C:4](=[O:7])[CH2:5][CH2:6]2)[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1 | Oc1ccc(-c2ccc(O)cc2)cc1 | null | null | [Pd] | 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 | 50 | 1 | A suspension of 50 g of 4,4′-biphenyldiol in 500 ml of toluene is hydrogenated at 5 bar and 125° C. in the presence of palladium on activated carbon. The reaction mixture is filtered and freed from water by azeotropic distillation. It is then treated with 29 g of pyridine sulfone and stirred at 50° C. for 1 hour. After... | O=C1CCC(C2CCC(=O)CC2)CC1 | null | 65.9 | null |
105,288 | ord_dataset-4ac1b977dc504cb5a6a8e85d7d777c45 | null | 1983-01-01T00:05:00 | true | [CH3:1][CH:2]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:3][N:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.C(Cl)Cl.S(=O)(=O)(O)O.[C:25](O)([CH3:28])([CH3:27])[CH3:26]>[Cl-].[Na+].O>[C:25]([C:14]1[CH:15]=[CH:16][C:11]([CH2:10][CH:2]([CH3:1])[CH2:3][N:4]2[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]2)=[CH:12][CH:13]=1)... | CC(C)(C)O | CC(Cc1ccccc1)CN1CCCCC1 | null | O=S(=O)(O)O | [Cl-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | ClCCl | null | null | null | null | null | null | null | null | null | 20 | null | 100 g of 1-(2-methyl-3-phenyl-propyl)-piperidine are added to 375 ml of methylene chloride. 255 g of 95-96% sulfuric acid are then added dropwise over a 1.5 hour period with rapid stirring while cooling with brine to an internal temperature of 10° C. The mixture is warmed to 20° C. and 42.5 g of tert.-butanol are added... | CC(Cc1ccc(C(C)(C)C)cc1)CN1CCCCC1 | null | null | null |
1,020,688 | ord_dataset-136cfada6ce247b4919085a57363459e | null | 2011-01-01T00:01:00 | true | [CH2:1]([N:3]([CH3:16])[C:4]1[O:5][C:6]2[C:7](=[C:9]([C:13]([O-:15])=O)[CH:10]=[CH:11][CH:12]=2)[N:8]=1)[CH3:2].[Li+].Cl.Cl.[NH2:20][C@H:21]1[CH:26]2[CH2:27][CH2:28][N:23]([CH2:24][CH2:25]2)[CH2:22]1>>[N:23]12[CH2:22][C@@H:21]([NH:20][C:13]([C:9]3[CH:10]=[CH:11][CH:12]=[C:6]4[O:5][C:4]([N:3]([CH2:1][CH3:2])[CH3:16])=[N... | CCN(C)c1nc2c(C(=O)[O-])cccc2o1 | N[C@@H]1CN2CCC1CC2 | null | Cl | [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 | Following general procedure GP-C1, a mixture of lithium 2-(ethyl(methyl)amino)benzoxazole-4-carboxylate and (S)-(−)-3-aminoquinuclidine dihydrochloride were coupled and to afford (S)—N-(quinuclidine-8-yl)-2-(ethyl(methyl)amino)benzoxazole-4-carboxamide, which was converted to the hydrochloride salt following general pr... | CCN(C)c1nc2c(C(=O)N[C@@H]3CN4CCC3CC4)cccc2o1 | null | null | null |
1,187,844 | ord_dataset-9cd817a75dfc4fe7ad19d4232772d5ff | null | 2012-01-01T00:07:00 | true | [C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:18]=[C:13]3[CH:12]=[C:11]2[C:27](OS(C2C=CC(C)=CC=2)(=O)=O)=[CH:28][CH:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:45][S:46]([C:49]1[CH:54]=[CH:53][C:52](B(... | CS(=O)(=O)c1ccc(B(O)O)cc1 | Cc1ccc(S(=O)(=O)OC(=CC2CCCC2)c2cc3cc(NC(=O)OC(C)(C)C)cnc3n2S(=O)(=O)c2ccccc2)cc1 | null | Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1 | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | To a mixture of toluene-4-sulfonic acid 1-(1-benzenesulfonyl-5-tert-butoxycarbonylamino-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-vinyl ester (0.5 g, 0.78 mmol), 4-methylsulfonyl phenylboronic acid (468 mg, 2.34 mmol), dichlorobis(triphenylphosphine)palladium (II) (55 mg, 0.08 mmol) in dioxane (5 mL) was added an aq... | CC(C)(C)OC(=O)Nc1cnc2c(c1)cc(C(=CC1CCCC1)c1ccc(S(C)(=O)=O)cc1)n2S(=O)(=O)c1ccccc1 | null | 67.2 | null |
11,643 | ord_dataset-7c810806c4564bada4a9550135bbb06f | null | 1976-01-01T00:08:00 | true | [Na].[OH:2][N:3]=[C:4]([C:8]#[N:9])[C:5]([NH2:7])=[O:6].Cl[C:11]([O:13][CH2:14][CH3:15])=[O:12].C(=O)([O-])O.[Na+]>CC(C)=O.O>[CH2:14]([O:13][C:11]([O:2][N:3]=[C:4]([C:8]#[N:9])[C:5]([NH2:7])=[O:6])=[O:12])[CH3:15] | N#CC(=NO)C(N)=O | CCOC(=O)Cl | null | O=C([O-])O | [Na+] | [Na] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC(C)=O | null | null | null | null | null | null | null | null | null | 0 | 1 | To a mixture of water (100 ml) and acetone (15 ml), sodium salt of 2-hydroxyimino-2-cyanoacetic acid amide (19.6 g) is added, and the obtained solution in which a part of the sodium salt is present in a suspended state is cooled at 0°C. Ethyl chloroformate (15 g) is dropwise added thereto, and the resulting mixture is,... | CCOC(=O)ON=C(C#N)C(N)=O | null | 87.9 | null |
380,167 | ord_dataset-993feac5ecf54388aa6326a220e46db3 | null | 1997-01-01T00:10:00 | true | [C:1]1([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][C:14]([NH:16][C@H:17]([C:21]([OH:23])=O)[CH:18]([CH3:20])[CH3:19])=[O:15])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.[NH2:49][C:50]1[S:54][C:53](=[S:55])[NH:52][N:51]=1>>[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][C:14]([NH:1... | Nc1n[nH]c(=S)s1 | CC(C)[C@H](NC(=O)Cc1ccc(-c2ccccc2)cc1)C(=O)O | null | C(=NC1CCCCC1)=NC1CCCCC1 | On1nnc2ccccc21 | null | null | null | null | 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-Phenyl)phenylacetyl)-valine (0.98 grams), 1-hydroxybenzotriazole (0.6 grams), dicyclohexylcarbodiimide (0.64 grams) and 5-amino-1,3,4-thiadiazole-2-thione (1.2 grams) were reacted according to the procedure described in Example 1. The resulting product was recrystallized from ethanol/pentane to give a white solid. ... | CC(C)[C@H](NC(=O)Cc1ccc(-c2ccccc2)cc1)C(=O)Nc1n[nH]c(=S)s1 | null | null | null |
1,751,841 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | [N+:1]([CH2:4][C:5]1([CH2:15][C:16](OCC)=O)[CH2:14][CH2:13][C:8]2([O:12][CH2:11][CH2:10][O:9]2)[CH2:7][CH2:6]1)([O-])=O.CC[OH:23]>[Ni]>[O:12]1[C:8]2([CH2:13][CH2:14][C:5]3([CH2:15][CH2:16][NH:1][C:4]3=[O:23])[CH2:6][CH2:7]2)[O:9][CH2:10][CH2:11]1 | CCOC(=O)CC1(C[N+](=O)[O-])CCC2(CC1)OCCO2 | CCO | null | [Ni] | null | null | null | 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 | 72 | To a solution of ethyl 2-(8-(nitromethyl)-1,4-dioxaspiro[4.5]decan-8-yl)acetate (109 g, 379.38 mmol) in EtOH (600 mL) was added Raney Ni (10 g). The reaction mixture was stirred under H2 atmosphere at rt for 72 h and filtered. The filter cake was washed with a mixture of DCM and MeOH (1/1 (v/v), 500 mL). The filtrate w... | O=C1NCCC12CCC1(CC2)OCCO1 | null | 83.8 | null |
1,396,569 | ord_dataset-12dc3bd21bcf44d09e5b4249afe15161 | null | 2014-01-01T00:02:00 | true | [CH2:1]([O:8][C:9](=[O:17])[CH2:10][CH2:11][CH2:12][C:13](=O)[CH2:14]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]([NH:25][C:26]([NH2:28])=[NH:27])([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]>CN(C=O)C>[C:21]([O:20][C:18]([N:25]1[CH:14]=[C:13]([CH2:12][CH2:11][CH2:10][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]... | O=C(CBr)CCCC(=O)OCc1ccccc1 | CC(C)(C)OC(=O)NC(=N)N | 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 | 25 | null | 6-bromo-5-oxo-hexanoic acid benzyl ester (3.42 g, 11.99 mmol) and Boc-guanidine (5.73 g, 35.97 mmol) were dissolved in DMF (35 mL) and allowed to stir at room temperature. After 48 h the DMF was removed under reduced pressure and the residue was taken up in ethyl acetate (100 mL) and washed with water (3×50 mL) and bri... | CC(C)(C)OC(=O)n1cc(CCCC(=O)OCc2ccccc2)nc1N | null | 64.7 | null |
943,588 | ord_dataset-ed680843f6d14f5c9901869b2a06b4a4 | null | 2010-01-01T00:03:00 | true | [Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[OH:11].S(=O)(=O)(O)O.[C:17](=O)([O-])[O-].[Na+].[Na+]>CO>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:17])=[O:7])=[CH:4][C:3]=1[OH:11] | O=C(O)c1ccc(Br)c(O)c1 | O=C([O-])[O-] | null | O=S(=O)(O)O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 0 | null | To a solution of 4-bromo-3-hydroxybenzoic acid (30 mmol) in methanol (100 mL) was added concentrated sulfuric acid (2.6 mL). The solution was heated at reflux for 5 hours, cooled to 0° C., and brought to pH 7 by adding saturated. aqueous sodium carbonate. The solution was evaporated to one-third the original volume. Wa... | COC(=O)c1ccc(Br)c(O)c1 | null | 89 | null |
912,082 | ord_dataset-c663259b80f947e2a8923796fb0e9a6b | null | 2009-01-01T00:10:00 | true | C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][NH:18][C:19]3[CH:24]=[CH:23][C:22]([C:25](=[O:27])[CH3:26])=[C:21]([OH:28])[C:20]=3[CH3:29])=[CH:13][CH:12]=2)[CH:5]=1.O[Li].O>C1COCC1.O>[C:25]([C:22]1[CH:23]=[CH:24][C:19]([NH:18][CH2:17][C:14]2[CH:15]=[CH:16][C:11]([CH2:... | COC(=O)c1cccc(Cc2ccc(CNc3ccc(C(C)=O)c(O)c3C)cc2)c1 | null | null | [Li]O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 8 | To 3-{4-[(4-acetyl-3-hydroxy-2-methyl-phenylamino)-methyl]-benzyl}-benzoic acid methyl ester (356 mg, 0.88 mmol) in THF (14 mL) is added a solution of LiOH.H2O (185 mg, 4.4 mmol) in H2O (7 mL). The reaction mixture is stirred at RT overnight. The reaction mixture is acidified to pH=7 and concentrated. The residue is pu... | CC(=O)c1ccc(NCc2ccc(Cc3cccc(C(=O)O)c3)cc2)c(C)c1O | null | 46.1 | null |
1,340,079 | ord_dataset-08852243bba44cb28769a5833f1515fe | null | 2013-01-01T00:09:00 | true | C([O:8][C:9]1[CH:10]=[C:11]2[C:17]([C:18]([NH:20][CH3:21])=[O:19])=[C:16]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[O:15][C:12]2=[CH:13][N:14]=1)C1C=CC=CC=1>C1COCC1.[Pd]>[F:28][C:25]1[CH:24]=[CH:23][C:22]([C:16]2[O:15][C:12]3=[CH:13][N:14]=[C:9]([OH:8])[CH:10]=[C:11]3[C:17]=2[C:18]([NH:20][CH3:21])=[O:19])... | CNC(=O)c1c(-c2ccc(F)cc2)oc2cnc(OCc3ccccc3)cc12 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | 0.33 | Pd/C (178 mg, 0.084 mmol) (10%; 50% wet) was added to a stirring solution of 5-(benzyloxy)-2-(4-fluorophenyl)-N-methylfuro[2,3-c]pyridine-3-carboxamide (630 mg, 1.674 mmol) in THF (83 ml) at room temperature. It was placed under an atmosphere of H2 and allowed to stir for 20 minutes after which a precipitate had formed... | CNC(=O)c1c(-c2ccc(F)cc2)oc2cnc(O)cc12 | null | 91.4 | null |
607,435 | ord_dataset-273fda773e864aaf9b71a30a2d9f2162 | null | 2003-01-01T00:08:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[C@H:10]([NH:19]C(OCC2C=CC=CC=2)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[C@H:10]([NH2:19])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3] | CC(C)(C)OC(=O)N1C[C@@H](NC(=O)OCc2ccccc2)[C@H](c2ccccn2)C1 | 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 | 18 | To a solution of 1-tert-butyloxycarbonyl-trans-3-benzyloxycarbonylamino-4-(2-pyridyl)pyrrolidine from step 6 above (3.9 g, 9.8 mmol) in EtOH (25 mL) was added 10% Pd on carbon (1.5 g). The mixture was shaken under an atmosphere of hydrogen (40 psi) at ambient temperature for 18 h on a Parr apparatus. The catalyst was r... | CC(C)(C)OC(=O)N1C[C@@H](N)[C@H](c2ccccn2)C1 | null | null | null |
846,944 | ord_dataset-e2b35e721c2741999b0005d12691f9fe | null | 2008-01-01T00:10:00 | true | [N+:1]([C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]2[N:13]=[C:14]([NH:17][C:18](=[O:27])[O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[S:15][CH:16]=2)=[CH:6][CH:5]=1)([O-])=O>[Pd].CO>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]2[N:13]=[C:14]([NH:17][C:18](=[O:27])[O:19][CH2:20][C:21]3[CH:22... | O=C(Nc1nc(/C=C/c2ccc([N+](=O)[O-])cc2)cs1)OCc1ccccc1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | 8 | A mixture of benzyl 4-[(E)-2-(4-nitrophenyl)ethenyl]-1,3-thiazol-2-ylcarbamate (1.4 g), palladium on carbon (140 mg) and methanol (2 ml) was stirred under hydrogen atmosphere (4 atm) at ambient temperature for 8 hours. The catalyst was filtered off, and the filtrate was concentrated in vacuo to give benzyl 4-[2-(4-amin... | Nc1ccc(CCc2csc(NC(=O)OCc3ccccc3)n2)cc1 | null | 92.5 | null |
575,258 | ord_dataset-f4512fe8cd804ac79da66cbc0c2b9d42 | null | 2002-01-01T00:12:00 | true | Br[C:2]1[CH:3]=[CH:4][C:5]2[NH:10][CH:9]([C:11]([F:14])([F:13])[F:12])[O:8][C:7]([CH3:16])([CH3:15])[C:6]=2[CH:17]=1.[Cl:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=1>>[Cl:18][C:19]1[CH:24]=[C:23]([C:2]2[CH:3]=[CH:4][C:5]3[NH:10][CH:9]([C:11]([F:14])([F:13])[F:12])[O:8][C:7]([CH3:16])([CH3:15])[C:6]=3[CH:17]=... | CC1(C)OC(C(F)(F)F)Nc2ccc(Br)cc21 | OB(O)c1cccc(Cl)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared according to the coupling procedure for Example 17 from 6-bromo-4,4-dimethyl-2-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazine and 3-chlorophenyl boronic acid. A yellowish solid: mp 108-109° C.; 1H-NMR (DMSO-d6) δ 7.69 (t, 1H, J=1.7 Hz), 7.59 (d, 1H, J=7.8 Hz), 7.35-7.50 (m, 3H), 7.32 (dt, 1H, J=8.1, 1.1 Hz),... | CC1(C)OC(C(F)(F)F)Nc2ccc(-c3cccc(Cl)c3)cc21 | null | null | null |
1,012,877 | ord_dataset-7448b89163bf426c9d9777809ce24cec | null | 2010-01-01T00:11:00 | true | [F:1][C:2]1[CH:3]=[C:4]([CH2:26][CH2:27][NH2:28])[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:19][CH2:18]1)[N:11]=2.O.[C:30]([OH:34])(=[O:33])[CH:31]=O.Cl>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH2:26][CH2:27][NH:28][CH2:31][C:30]([OH... | NCCc1ccc(-c2nc3ccc(C4(c5ccccc5)CC4)nc3s2)c(F)c1 | O=CC(=O)O | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O | null | null | null | null | null | null | null | null | null | 25 | 5 | To 2-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)-ethanamine (83 mg, 0.213 mmol) was added glyoxylic acid monohydrate (39 mg, 0.426 mmol) and DCM (1 mL) before it was stirred for 5 h at ambient temperature. The reaction mixture was concentrated before adding concentrated hydrochloric acid (2.... | O=C(O)CNCCc1ccc(-c2nc3ccc(C4(c5ccccc5)CC4)nc3s2)c(F)c1 | null | null | null |
783,208 | ord_dataset-8034115bd2ec4d3e95bd3ff7cfde0bde | null | 2007-01-01T00:07:00 | true | [CH:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][C:7]([C:13]#[N:14])=[C:6]2[O:15][CH2:16][C:17]([F:20])([F:19])[F:18])=O.COC1C=CC(/C=[C:36]2/[C:37]([NH:39][C:40]([S:42]/2)=[NH:41])=[O:38])=CC=1OC1CCCC1.C([O-])(=O)C.[Na+]>C(O)(=O)C>[NH2:41][C:40]1[S:42]/[C:36](=[CH:1]\[C:3]2[CH:4]=[C:5]3[C:10](=[CH:11][CH... | N#Cc1cnc2ccc(C=O)cc2c1OCC(F)(F)F | COc1ccc(/C=C2\SC(=N)NC2=O)cc1OC1CCCC1 | null | CC(=O)[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | Similar procedure as described in example 38 was used, starting from 6-formyl-4-(2,2,2-trifluoro-ethoxy)-quinoline-3-carbonitrile (example 43b), pseudothiohydantoin, sodium acetate and acetic acid to give 6-[2-amino-4-oxo-4H-thiazol-(5Z)-ylidenemethyl]-4-(2,2,2-trifluoro-ethoxy)-quinoline-3-carbonitrile. LC-MS m/e 379 ... | N#Cc1cnc2ccc(/C=C3\SC(N)=NC3=O)cc2c1OCC(F)(F)F | null | null | null |
51,013 | ord_dataset-e5870fef54544989915ccced8dd8d849 | null | 1979-01-01T00:01:00 | true | [Br:1]Br.[C:3]([C:6]1[CH:7]=[C:8]([CH:18]=[CH:19][CH:20]=1)[NH:9][C:10]([C:12]1[CH:16]=[C:15]([CH3:17])[O:14][N:13]=1)=[O:11])(=[O:5])[CH3:4]>C(Cl)(Cl)Cl.C(OCC)C>[Br:1][CH2:4][C:3]([C:6]1[CH:7]=[C:8]([CH:18]=[CH:19][CH:20]=1)[NH:9][C:10]([C:12]1[CH:16]=[C:15]([CH3:17])[O:14][N:13]=1)=[O:11])=[O:5] | CC(=O)c1cccc(NC(=O)c2cc(C)on2)c1 | BrBr | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 0.5 | A solution of bromine (12.5 g) in chloroform (60 ml) was added to a slurry of 3'-acetyl-5-methyl-3-isoxazolecarboxanilide. 1/4 hydrate (19 g) in chloroform (190 ml). The mixture was stirred for 1/2 hour and diluted with diethyl ether. The product was filtered and dried. Yield 21.0 g = (84%,) m.p. 172°-174°. | Cc1cc(C(=O)Nc2cccc(C(=O)CBr)c2)no1 | null | null | null |
445,743 | ord_dataset-a4f0b79f6b9847168861270b79f84afa | null | 1999-01-01T00:11:00 | true | [Br:1][CH:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:3]([NH:5][C:6]([CH3:11])([CH3:10])[C:7]([OH:9])=O)=[O:4].Cl.CN(CCCN=C=NCC)C.[Cl:30][C:31]1[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][C:32]=1[NH2:33].O>ClCCl>[Cl:30][C:31]1[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][C:32]=1[NH:33][C:7](=[O:9])[C:6]([NH:5][C:3](=[O:4]... | CC(C)(NC(=O)C(Br)c1ccccc1)C(=O)O | Nc1cc(Cl)ccc1Cl | null | CCN=C=NCCCN(C)C | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O | null | null | null | null | null | null | null | null | null | null | 0.17 | A solution of 2-(α-bromophenylacetylamino)isobutyric acid (1.9 g) in dichloromethane (30 mL) was cooled to 0° C., to which dimethylaminopropylethylcarbodiimide hydrochloride (1.3 g) was added. The mixture was stirred for 10 minutes at 0° C. to room temperature. 2,5-Dichloroaniline (1.0 g) was added to the mixture, whic... | CC(C)(NC(=O)C(Br)c1ccccc1)C(=O)Nc1cc(Cl)ccc1Cl | null | 83.9 | null |
Subsets and Splits
No community queries yet
The top public SQL queries from the community will appear here once available.