original_index int64 2 1.77M | agent_000 stringlengths 1 540 ⌀ | agent_001 stringlengths 1 852 ⌀ | agent_002 stringlengths 1 247 ⌀ | date_of_experiment timestamp[ns]date | extracted_from_file stringclasses 489 values | grant_date timestamp[ns]date 1976-01-01 00:01:00 2016-01-01 00:09:00 | is_mapped bool 1 class | procedure_details stringlengths 8 24.5k | product_000 stringlengths 1 484 | product_001 stringlengths 1 208 ⌀ | reactant_000 stringlengths 1 902 | reactant_001 stringlengths 1 902 ⌀ | reactant_002 stringlengths 1 285 ⌀ | rxn_str stringlengths 87 6.12k | rxn_time float64 0 2.16k ⌀ | solvent_000 stringclasses 446 values | solvent_001 stringclasses 405 values | solvent_002 stringclasses 330 values | temperature float64 -230 30.1k ⌀ | yield_000 float64 0 90,205,156,600B ⌀ | yield_001 float64 0 100M ⌀ | 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_003 null | solvent_004 null | solvent_005 null | solvent_006 null | solvent_007 null | solvent_008 null | solvent_009 null | solvent_010 null |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
212,457 | null | null | null | null | ord_dataset-e6e5ffd5405c481d8061087049155f9f | 1990-01-01T00:07:00 | true | Ethyl 2-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)-2-hydroxypropylthio]benzimidazole-5-carboxylate was prepared in a similar manner to Example 2 with 3-(4-acetyl-3-hydroxy-2-propylphenoxy)-1,2-epoxypropane (1.91 g) and ethyl 2-mercaptobenzimidazole-5-carboxylate (1.70 g). 2.10 g (58.1%) of the esters was obtained as a yellow oil. This ester (2.10 g) was converted to the title compound (870 mg. 44.1%) as pale brown crystals in the same manner as Example 2, mp 133-135° C. | CCCc1c(OCC(O)CSc2nc3ccc(C(=O)OCC)cc3[nH]2)ccc(C(C)=O)c1O | null | CCOC(=O)c1ccc2nc(S)[nH]c2c1 | CCCc1c(OCC2CO2)ccc(C(C)=O)c1O | null | [C:1]([C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][CH:10]2[O:12][CH2:11]2)=[C:6]([CH2:15][CH2:16][CH3:17])[C:5]=1[OH:18])(=[O:3])[CH3:2].[SH:19][C:20]1[NH:21][C:22]2[CH:28]=[C:27]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:26]=[CH:25][C:23]=2[N:24]=1>>[C:1]([C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][CH:10]([OH:12])[CH2:11][S:19][C:20]2[NH:21][C:22]3[CH:28]=[C:27]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:26]=[CH:25][C:23]=3[N:24]=2)=[C:6]([CH2:15][CH2:16][CH3:17])[C:5]=1[OH:18])(=[O:3])[CH3:2] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
479,344 | null | null | null | null | ord_dataset-21c1b1c06c7e4e09a38b5b1c71a32e52 | 2000-01-01T00:10:00 | true | Following the procedure of Example 97, the reaction of 1,2,4-triazole with 2-chloro-6-ethyl-4-(3,4-ethylendioxybenzylamino)-thieno-[2,3-d]-pyrimidine gives 2-(1,2,4-triazol-1-yl)-6-ethyl-4-(3,4-ethylendioxybenzylamino)-thieno-[2,3-d]-pyrimidine. | CCc1cc2c(NCc3ccc4c(c3)OCCO4)nc(-n3cncn3)nc2s1 | null | CCc1cc2c(NCc3ccc4c(c3)OCCO4)nc(Cl)nc2s1 | c1nc[nH]n1 | null | [NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.Cl[C:7]1[N:8]=[C:9]([NH:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]3[O:26][CH2:27][CH2:28][O:29][C:22]=3[CH:21]=2)[C:10]2[CH:15]=[C:14]([CH2:16][CH3:17])[S:13][C:11]=2[N:12]=1>>[N:1]1([C:7]2[N:8]=[C:9]([NH:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]4[O:26][CH2:27][CH2:28][O:29][C:22]=4[CH:21]=3)[C:10]3[CH:15]=[C:14]([CH2:16][CH3:17])[S:13][C:11]=3[N:12]=2)[CH:5]=[N:4][CH:3]=[N:2]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 |
1,582,282 | CC(C)[N-]C(C)C | [Li+] | null | null | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | 2015-01-01T00:05:00 | true | To a solution of 2,4-difluoro-1-methoxybenzene (156 mg) in tetrahydrofuran (5 mL) at −78° C. is added a 2M solution of lithium diisopropylamide in THF (540 μL). After stirring for 45 min a solution of 1-(2-trimethylsilylethoxymethyl)-1H-benzimidazole-2-carbaldehyde (which can be prepared according to US2003/220341 or U.S. Pat. No. 6,476,041 for example) (300 mg) in tetrahydrofuran (5 mL) is added at −78° C. and the reaction mixture allowed to warm to room temperature. After hydrolysis with aqueous saturated ammonium chloride and extraction with ethyl acetate, the organic phase is dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by chromatography over silica gel (gradient dichloromethane/methanol from 100/0 to 95/5) to afford (2,6-difluoro-3-methoxyphenyl)[1-(2-trimethylsilylethoxymethyl)-1H-benzimidazol-2-yl]methanol. | COc1ccc(F)c(C(O)c2nc3ccccc3n2COCC[Si](C)(C)C)c1F | null | COc1ccc(F)cc1F | C[Si](C)(C)CCOCn1c(C=O)nc2ccccc21 | null | [F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[O:9][CH3:10].C([N-]C(C)C)(C)C.[Li+].[CH3:19][Si:20]([CH3:37])([CH3:36])[CH2:21][CH2:22][O:23][CH2:24][N:25]1[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[N:27]=[C:26]1[CH:34]=[O:35]>O1CCCC1>[F:1][C:2]1[C:3]([O:9][CH3:10])=[CH:4][CH:5]=[C:6]([F:8])[C:7]=1[CH:34]([C:26]1[N:25]([CH2:24][O:23][CH2:22][CH2:21][Si:20]([CH3:36])([CH3:37])[CH3:19])[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[N:27]=1)[OH:35] | null | C1CCOC1 | null | null | 25 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
832,525 | C[Si](C)(C)Cl | null | null | null | ord_dataset-47bd90bf5ec74fcd99ce250a56e18c8f | 2008-01-01T00:07:00 | true | Combine 2-nitro-meta-xylene (5 mL, 0.037 mol), N,N-dimethylformamide dimethylacetal (5.4 mL, 1.1 eq) and N,N-dimethylformamide (60 mL) in a flask and reflux under nitrogen for 2 days. Let cool to room temperature then concentrate to approximately one-half volume. Add methanol (40 mL) and trimethylsilylchloride (6.6 mL, 1.4 eq). Reflux overnight. Dilute with ethyl acetate after cooling to room temperature then extract with saturated sodium bicarbonate followed by brine. Dry over magnesium sulfate, filter and concentrate. Purification by column chromatography (9:1 Hexanes:ethyl acetate) gives 1.15 g (14%) product as a light yellow oil. 1H NMR (400 MHz, DMSO-d6) δ 2.23 (s, 3H), 2.80 (d, J=5.36 Hz, 2H), 3.19 (s, 6H), 4.45 (m, 1H), 7.32 (m, 2H), 7.42 (m, 1H). | COC(Cc1cccc(C)c1[N+](=O)[O-])OC | null | Cc1cccc(C)c1[N+](=O)[O-] | COC(OC)N(C)C | null | [N+:1]([C:4]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:5]=1[CH3:11])([O-:3])=[O:2].[CH3:12][O:13][CH:14]([O:18][CH3:19])N(C)C.CN(C)C=O.C[Si](Cl)(C)C>C(OCC)(=O)C.CO>[CH3:12][O:13][CH:14]([O:18][CH3:19])[CH2:11][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]([CH3:10])[C:4]=1[N+:1]([O-:3])=[O:2] | null | CN(C)C=O | CO | CCOC(C)=O | 25 | null | 14 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,297,256 | O=[Pt]=O | null | null | null | ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c | 2013-01-01T00:05:00 | true | 3-[2-[5-[[1-(tert-Butoxycarbonyl)-2(S)-azetidinyl]methoxy]-3-pyridyl]ethyl]phenylmethyl azide is dissolved in ethanol, and a catalytic amount of PtO2 is added. The reaction flask is attached to a H2 balloon by way of a three-way stopcock, and the atmosphere is exchanged. The mixture is stirred at room temperature. The reaction is followed by TLC and terminated by replacing the atmosphere with N2 when the starting material has disappeared. The catalyst is removed by centrifugation or filtration over a filter membrane. The solution is evaporated and the residue used directly in the following step. If desired, the product can be purified by CC on silica gel eluting with CH2Cl2/methanol/Et3N or CH2Cl2/methanol/conc. aqueous NH3, or on deactivated basic alumina with CH2Cl2/methanol. | CC(C)(C)OC(=O)N1CC[C@H]1COc1cncc(CCc2cccc(CN)c2)c1 | null | CC(C)(C)OC(=O)N1CC[C@H]1COc1cncc(CCc2cccc(CN=[N+]=[N-])c2)c1 | null | null | [C:1]([O:5][C:6]([N:8]1[CH2:11][CH2:10][C@H:9]1[CH2:12][O:13][C:14]1[CH:15]=[C:16]([CH2:20][CH2:21][C:22]2[CH:23]=[C:24]([CH2:28][N:29]=[N+]=[N-])[CH:25]=[CH:26][CH:27]=2)[CH:17]=[N:18][CH:19]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.O=[Pt]=O>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH2:10][C@H:9]1[CH2:12][O:13][C:14]1[CH:15]=[C:16]([CH2:20][CH2:21][C:22]2[CH:23]=[C:24]([CH2:28][NH2:29])[CH:25]=[CH:26][CH:27]=2)[CH:17]=[N:18][CH:19]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3] | null | CCO | null | null | 25 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,695,671 | null | null | null | null | ord_dataset-54347fcace774f89850681d6dec8009f | 2016-01-01T00:03:00 | true | Reaction of 3-[6-amino-5-(pyridin-4-ylcarbamoyl)-pyridin-3-yl]-benzoic acid with ammonia gives “A99”; method 2: HPLC/MS: 1.64 min, [M+H]=334. | NC(=O)c1cccc(-c2cnc(N)c(C(=O)Nc3ccncc3)c2)c1 | null | Nc1ncc(-c2cccc(C(=O)O)c2)cc1C(=O)Nc1ccncc1 | N | null | [NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=2)[C:11]([OH:13])=O)=[CH:4][C:3]=1[C:17](=[O:25])[NH:18][C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1.[NH3:26]>>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:16]=[CH:15][CH:14]=[C:10]([C:11](=[O:13])[NH2:26])[CH:9]=2)=[CH:4][C:3]=1[C:17]([NH:18][C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1)=[O:25] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
116,373 | null | null | null | null | ord_dataset-19041548671f410397ce7f00536a9be3 | 1984-01-01T00:04:00 | true | To a solution of the above 1-methyl-3-methylthiomethyl-4-quinolone (4.86 g.) in dichloromethane (220 ml.) at -20° was added a solution of 3-chloroperbenzoic acid (85%, 4.86 g.) in dichloromethane (220 ml.) during 1 hour. The solution was allowed to warm to room temperature and extracted with saturated aqueous sodium bicarbonate until free of per-acid. The organic phase was dried over anhydrous magnesium sulphate and evaporated to give a solid product. The product was crystallised from acetone to give the novel 1-methyl-3-methylsulphinylmethyl-4-quinolone, m.p. 93°-95°. | Cn1cc(CS(C)=O)c(=O)c2ccccc21 | null | O=C(OO)c1cccc(Cl)c1 | CSCc1cn(C)c2ccccc2c1=O | null | [CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[C:4]([CH2:13][S:14][CH3:15])=[CH:3]1.ClC1C=CC=C(C(OO)=[O:24])C=1>ClCCl>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[C:4]([CH2:13][S:14]([CH3:15])=[O:24])=[CH:3]1 | null | ClCCl | null | null | 25 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
46,990 | O=C([O-])[O-] | [K+] | null | null | ord_dataset-6d529f04a1724b5d85dcc290cf4c38bb | 1978-01-01T00:10:00 | true | 1.07 g of potassium carbonate and 1.3 g of ethyl bromoacetate were added to a solution of 1.6 g of the product of Step A in 50 ml of methyl ethyl ketone and the mixture was refluxed for an hour and was cooled to 30° C. The mixture was filtered and the filtrate was evaporated to dryness. The residue was taken up in ethyl acetate and the solution was washed with water, dried and evaporated to dryness to obtain 2.3 g of ethyl (2-ethoxycarbonyl-5-chloro-3-thienyl)-oxyacetate. | CCOC(=O)COc1cc(Cl)sc1C(=O)OCC | null | CCOC(=O)c1sc(Cl)cc1O | CCOC(=O)CBr | null | C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].[CH2:14]([O:16][C:17]([C:19]1[S:20][C:21]([Cl:25])=[CH:22][C:23]=1[OH:24])=[O:18])[CH3:15]>C(C(C)=O)C>[CH2:14]([O:16][C:17]([C:19]1[S:20][C:21]([Cl:25])=[CH:22][C:23]=1[O:24][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:18])[CH3:15] | null | CCC(C)=O | null | null | 30 | null | 101.5 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,381,749 | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | 2013-01-01T00:12:00 | true | A solution 3-(2-hydroxyethyl)-2-(triethylsilyl)-1H-indole-5-carbonitrile (0.873 g; 2.91 mmol) in THF (6 mL) was added to a solution of triphenylphosphine (1.52 g; 5.81 mmol) and perbromomethane (1.93 g; 5.81 mmol) in THF (30 mL) pre-stirred for 30 minutes. The resulting mixture was stirred at room temperature overnight, filtered and concentrated under reduced pressure. The crude mixture was purified by flash chromatography on silica (eluent 2 to 40% ethyl acetate in heptane) to yield 0.906 g (86%) of the title compound as a white solid. | CC[Si](CC)(CC)c1[nH]c2ccc(C#N)cc2c1CCBr | null | CC[Si](CC)(CC)c1[nH]c2ccc(C#N)cc2c1CCO | BrC(Br)(Br)Br | null | O[CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]#[N:14])[CH:11]=2)[NH:6][C:5]=1[Si:15]([CH2:20][CH3:21])([CH2:18][CH3:19])[CH2:16][CH3:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:41]C(Br)(Br)Br>C1COCC1>[Br:41][CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]#[N:14])[CH:11]=2)[NH:6][C:5]=1[Si:15]([CH2:20][CH3:21])([CH2:18][CH3:19])[CH2:16][CH3:17] | 0.5 | C1CCOC1 | null | null | null | 85.7 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
731,742 | CC(=O)[O-] | [Na+] | null | null | ord_dataset-eb4226b4f7644a01a737e7547b70014a | 2006-01-01T00:09:00 | true | 0.35 mol (32 mL) of POCl3 was added at 0° C. to a 1.0 mol (77 mL) of DMF (excess of DMF used as solvent). At the end of the addition, the mixture was allowed to warm to room temperature and stirred for 1 h. Then it was cooled again to 0° C. and treated with 3-methyl-2-phenylthiophene (60 g, 0.35 mol). The resulting reaction mixture was allowed to reach room temperature and after 12 h stirring at the same temperature was heated at 80° C. for 2 days. Then it was poured into a mixture of ice and water, added of sodium acetate and extracted with CHCl3 (3×150 mL). The organic phase was separated, washed with water until neutral pH, dried over MgSO4 and evaporated off to dryness. The residue was crystallized. Yield 60.2 g (85%). | Cc1cc(C=O)sc1-c1ccccc1 | null | Cc1ccsc1-c1ccccc1 | CN(C)C=O | null | O=P(Cl)(Cl)Cl.CN([CH:9]=[O:10])C.[CH3:11][C:12]1[CH:16]=[CH:15][S:14][C:13]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([O-])(=O)C.[Na+]>O>[CH:9]([C:15]1[S:14][C:13]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[C:12]([CH3:11])[CH:16]=1)=[O:10] | 1 | O=P(Cl)(Cl)Cl | O | null | 25 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
608,534 | O=C([O-])[O-] | [K+] | null | null | ord_dataset-73916d628db147c89020b3baac642d48 | 2003-01-01T00:09:00 | true | 4-hydroxy-8-methoxynaphthalene-1-carbaldehyde (1 g, 5 mmol) was dissolved in DMF (15 mL). To this mixture potassium carbonate (3.4 g, 25 mmol) and 1,2-dibromoethane (4 mL, 50 mmol) were added and the resulting mixture was stirred at room temperature for 16 hours. Water. (150 mL) was added and the resulting mixture was extracted with ethyl acetate (3×90 mL). The combined organic extracts were washed with saturated sodium chloride (100 mL), dried (MgSO4) and evaporated in vacuo to afford 1.13 g (74%) of 4-(2-bromoethoxy)-8-methoxynaphthalene-1-carbaldehyde. | COc1cccc2c(OCCBr)ccc(C=O)c12 | null | BrCCBr | COc1cccc2c(O)ccc(C=O)c12 | null | [OH:1][C:2]1[C:11]2[C:6](=[C:7]([O:12][CH3:13])[CH:8]=[CH:9][CH:10]=2)[C:5]([CH:14]=[O:15])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Br:22][CH2:23][CH2:24]Br.O>CN(C=O)C>[Br:22][CH2:23][CH2:24][O:1][C:2]1[C:11]2[C:6](=[C:7]([O:12][CH3:13])[CH:8]=[CH:9][CH:10]=2)[C:5]([CH:14]=[O:15])=[CH:4][CH:3]=1 | 16 | CN(C)C=O | O | null | 25 | 73.1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
763,891 | null | null | null | null | ord_dataset-7a8649d55889427e85b208ae89475895 | 2007-01-01T00:04:00 | true | Example 51 was prepared from 2,2-diphenylpropanoic acid and N-{5-[1-(3-aminopropyl)-4-piperidinyl]-2-fluorophenyl}-2-methylpropanamide according to the procedures described in Scheme 9: 1H NMR (400 MHz, CDCl3) δ 8.27–8.13 (m, 1H), 8.04 (s, 1H), 7.62 (s, 1H), 7.50–7.39 (m, 1H), 7.39–7.16 (m, 7H), 7.12–6.90 (m, 2H), 6.79–6.60 (br, 1H), 4.94–4.61 (br, 1H), 3.60–3.22 (m, 4H), 2.89–2.76 (m, 2H), 2.76–2.55 (m, 4H), 2.55–2.34 (m, 3H), 2.14–1.82 (m, 3H), 2.00 (s, 3H), 1.26 (d, 6H, J=6.4 Hz); ESMS m/e: 530.4 (M+H)+; Anal. Calc. for (HCl salt) C33H41ClFN3O2.0.24CHCl3.0.96H2O: C, 65.23; H, 7.11; N, 6.86. Found: C, 64.96; H, 7.36; N, 6.87. | CC(C)C(=O)Nc1cc(C2CCN(CCCNC(=O)C(C)(c3ccccc3)c3ccccc3)CC2)ccc1F | null | CC(C(=O)O)(c1ccccc1)c1ccccc1 | CC(C)C(=O)Nc1cc(C2CCN(CCCN)CC2)ccc1F | null | [C:1]1([C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([CH3:11])[C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:18][CH2:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][CH:25]([C:28]2[CH:29]=[CH:30][C:31]([F:40])=[C:32]([NH:34][C:35](=[O:39])[CH:36]([CH3:38])[CH3:37])[CH:33]=2)[CH2:24][CH2:23]1>>[F:40][C:31]1[CH:30]=[CH:29][C:28]([CH:25]2[CH2:24][CH2:23][N:22]([CH2:21][CH2:20][CH2:19][NH:18][C:8](=[O:10])[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH3:11])[CH2:27][CH2:26]2)=[CH:33][C:32]=1[NH:34][C:35](=[O:39])[CH:36]([CH3:37])[CH3:38] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,259,091 | O=S(=O)(O)O | null | null | null | ord_dataset-266f60b4555945d6afb2d2bdf5fa04e0 | 2013-01-01T00:02:00 | true | (±)-{8-Fluoro-2-[4-(3-methoxyphenyl)piperazin-1-yl]-3-(2-methoxy-5-trifluoromethylphenyl)-3,4-dihydroquinazolin-4-yl}acetic acid (54 g) is dissolved in methanol (540 g), then concentrated sulphuric acid (7.85 ml) is added. The mixture is stirred under reflux for 26 h, then cooled and concentrated in vacuo to ca. one third of the original volume. Water (150 ml) and dichloromethane (150 ml) are added, then the phases are separated. The organic phase is extracted with saturated sodium hydrogencarbonate solution (two times 140 ml), dried over sodium sulphate and concentrated to give a foamy residue. This is dissolved twice in succession in ethanol (150 ml each) and concentrated, and subsequently dried for 18 h in vacuo using entraining nitrogen. A total of 41.6 g of methyl {8-fluoro-2-[4-(3-methoxyphenyl)piperazin-1-yl]-3-[2-methoxy-5-(trifluoromethyl)phenyl]-3,4-dihydroquinazolin-4-yl}acetate are thus obtained as an amorphous solid, corresponding to 75.2% of theory. | COC(=O)CC1c2cccc(F)c2N=C(N2CCN(c3cccc(OC)c3)CC2)N1c1cc(C(F)(F)F)ccc1OC | null | COc1cccc(N2CCN(C3=Nc4c(F)cccc4C(CC(=O)O)N3c3cc(C(F)(F)F)ccc3OC)CC2)c1 | CO | null | [F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([N:12]1[CH2:17][CH2:16][N:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=3)[CH2:14][CH2:13]1)[N:8]([C:26]1[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[CH:28][C:27]=1[O:36][CH3:37])[CH:7]2[CH2:38][C:39]([OH:41])=[O:40].S(=O)(=O)(O)O.[CH3:47]O>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([N:12]1[CH2:13][CH2:14][N:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=3)[CH2:16][CH2:17]1)[N:8]([C:26]1[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[CH:28][C:27]=1[O:36][CH3:37])[CH:7]2[CH2:38][C:39]([O:41][CH3:47])=[O:40] | null | CCO | null | null | null | 75.2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
5,281 | CCOC(=O)N1C2CCC1CN(C)C2 | Cl | null | null | ord_dataset-a5669edbeffe43bf8514c1bfede8f882 | 1976-01-01T00:04:00 | true | 3-Methyl-3,8-diazabicyclo[3.2.1]octane dihydrochloride (3.0 g, 0.0151 mole), prepared as described in Example 5, was reacted with 1.21 ml (0.0151 mole) ethyl isocyanate in a procedure as described for 8-carbethoxy-3-methyl-3,8-diazabicyclo[3.2.1]octane in Example 6. The crude desired product, as the free base, was purified by chromatography on alumina with chloroform elution. An hydrochloride salt was made by treatment of a solution of the free base in diethyl ether with ethanolic hydrogen chloride and filtering to collect 1.0 g (28% yield) white solid exhibiting a dual melting point of 100°-140° C and 191°-202° C until dried 2 hours at 126° C in vacuo after which the desired product hydrochloride salt melted at 205°-215° C. | CCNC(=O)N1C2CCC1CN(C)C2 | null | CCN=C=O | CN1CC2CCC(C1)N2 | null | Cl.Cl.[CH3:3][N:4]1[CH2:10][CH:9]2[NH:11][CH:6]([CH2:7][CH2:8]2)[CH2:5]1.[CH2:12]([N:14]=[C:15]=[O:16])[CH3:13].C(N1C2CCC1CN(C)C2)(OCC)=O>>[CH2:12]([NH:14][C:15]([N:11]1[CH:9]2[CH2:8][CH2:7][CH:6]1[CH2:5][N:4]([CH3:3])[CH2:10]2)=[O:16])[CH3:13] | null | null | null | null | null | null | 33.6 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
764,540 | O=C([O-])[O-] | [K+] | null | null | ord_dataset-7a8649d55889427e85b208ae89475895 | 2007-01-01T00:04:00 | true | Potassium carbonate (122 mg, 0.883 mmol) and then n-propyl bromide (40 μl, 0.440 mmol) were added to a solution of the N-(8-azabicyclo[3.2.1]oct-3-yl)-4-methyl-1H-indazol-5-amine (74 mg, 0.289 mmol) obtained in Example 501 in N,N-dimethylformamide (2 ml), and the resulting mixture was stirred at room temperature for 15 hours. After the solid was removed by filtration, the solvent was distilled off under reduced pressure as an azeotrope with toluene. The residue was purified by a silica gel column chromatography (chloroform/methanol/triethylamine=100/1/5) and then a preparative thin-layer chromatography (200×200×0.5 mm, 2 plates, eluent: chloroform/methanol/triethylamine=100/5/5) to obtain N-(8-propyl-8-azabicyclo[3.2.1]oct-3-yl)-4-methyl-1H-indazol-5-amine (36 mg, 42%). | CCCN1C2CCC1CC(Nc1ccc3[nH]ncc3c1C)C2 | null | CCCBr | Cc1c(NC2CC3CCC(C2)N3)ccc2[nH]ncc12 | null | C(=O)([O-])[O-].[K+].[K+].[CH3:7][CH2:8][CH2:9]Br.[CH:11]12[NH:18][CH:15]([CH2:16][CH2:17]1)[CH2:14][CH:13]([NH:19][C:20]1[C:21]([CH3:29])=[C:22]3[C:26](=[CH:27][CH:28]=1)[NH:25][N:24]=[CH:23]3)[CH2:12]2>CN(C)C=O>[CH2:9]([N:18]1[CH:15]2[CH2:16][CH2:17][CH:11]1[CH2:12][CH:13]([NH:19][C:20]1[C:21]([CH3:29])=[C:22]3[C:26](=[CH:27][CH:28]=1)[NH:25][N:24]=[CH:23]3)[CH2:14]2)[CH2:8][CH3:7] | 15 | CN(C)C=O | null | null | 25 | 41.7 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,749,596 | null | null | null | null | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | 2016-01-01T00:07:00 | true | A slurry of 8-bromo-2-chloro-3-(pyridin-3-yl)quinazolin-4(3H)-one (403b, 0.20 g, 0.594 mmol) and isopropylamine (2.04 mL, 23.77 mmol) was sealed and heated in an 80° C. oil bath for 1 h. The reaction was partitioned between sat'd aq. NaHCO3 and DCM. The aqueous layer was extracted with DCM 2 times, and the combined organics were dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give 8-bromo-2-(isopropylamino)-3-(pyridin-3-yl)quinazolin-4(3H)-one (0.22 g, 0.612 mmol, 103% yield) as a light yellow foam. 1H NMR (400 MHz, CDCl3) δ ppm 8.83 (1H, d, J=3.5 Hz), 8.60 (1H, br. s.), 8.08 (1H, dd, J=7.8, 1.6 Hz), 7.94 (1H, dd, J=7.7, 1.5 Hz), 7.66-7.75 (1H, m), 7.60 (1H, dd, J=8.0, 4.9 Hz), 7.04 (1H, t, J=7.8 Hz), 4.32-4.49 (1H, m), 3.80 (1H, d, J=6.3 Hz), 1.23 (6H, m). m/z (ESI, +ve) 359.0/361.0 (M+H)+. | CC(C)Nc1nc2c(Br)cccc2c(=O)n1-c1cccnc1 | null | O=c1c2cccc(Br)c2nc(Cl)n1-c1cccnc1 | CC(C)N | null | [Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9](Cl)[N:8]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[C:7]2=[O:19].[CH:20]([NH2:23])([CH3:22])[CH3:21]>>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([NH:23][CH:20]([CH3:22])[CH3:21])[N:8]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[C:7]2=[O:19] | null | null | null | null | 80 | null | 103 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,481,372 | Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1 | [Cu]I | null | null | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | 2014-01-01T00:09:00 | true | Into a round bottom flask was added 3-ethynyl-2-fluoropyridine (0.3 g, 0.002 mol), 4-fluoro-1-iodo-2-nitrobenzene (0.675 g, 0.00253 mol), bis(triphenylphosphine)palladium(II) chloride (0.09 g, 0.1 mmol), copper(I) iodide (0.04 g, 0.2 mmol), and triethylamine (0.52 mL, 3.7 mmol) in N,N-dimethylformamide (4 mL). The reaction was stirred at room temperature for 2 hours. The reaction was extracted with ethyl acetate, and the combined organic extracts were washed with brine (3×), dried over MgSO4, and purified by column chromatography on silica gel (10% ethyl acetate 90% hexanes), to give 0.443 g of product. 1H NMR (400 MHz, CDCl3): δ 8.44-8.50 (m, 1H), 7.99-8.02 (m, 1H), 7.79-7.90 (m, 1H), 7.78-7.82 (m, 1H), 7.37-7.42 (m, 1H), 7.23-7.29 (m, 1H). MS [M+H]=261.0. | O=[N+]([O-])c1cc(F)ccc1C#Cc1cccnc1F | null | C#Cc1cccnc1F | O=[N+]([O-])c1cc(F)ccc1I | null | [C:1]([C:3]1[C:4]([F:9])=[N:5][CH:6]=[CH:7][CH:8]=1)#[CH:2].[F:10][C:11]1[CH:16]=[CH:15][C:14](I)=[C:13]([N+:18]([O-:20])=[O:19])[CH:12]=1.C(N(CC)CC)C>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[F:9][C:4]1[C:3]([C:1]#[C:2][C:14]2[CH:15]=[CH:16][C:11]([F:10])=[CH:12][C:13]=2[N+:18]([O-:20])=[O:19])=[CH:8][CH:7]=[CH:6][N:5]=1 | 2 | CN(C)C=O | CCN(CC)CC | null | 25 | null | 85.1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
64,415 | [Na+] | null | null | null | ord_dataset-d986d6c6630b41ee8d401fd85be47701 | 1980-01-01T00:04:00 | true | To a warm mixture of 7 g. (18.3 m moles) sodium 4-(hexadecylamino)benzoate in 100 ml. ethanol is added 4.7 g. (18.3 m moles) ethyl α-tosyloxypropionate. After 17 hours at reflux, the cooled solution is diluted with an equal volume of water and the resultant precipitate is filtered. After washing with cold ethanol and drying, the product is crystallized from acetonitrile to yield the product as colorless crystals. | CCCCCCCCCCCCCCCCNc1ccc(C(=O)OC(C)C(=O)OCC)cc1 | null | CCCCCCCCCCCCCCCCNc1ccc(C(=O)[O-])cc1 | CCOC(=O)C(C)OS(=O)(=O)c1ccc(C)cc1 | null | [CH2:1]([NH:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([O-:24])=[O:23])=[CH:20][CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[Na+].C(O)C.S(O[CH:42]([CH3:48])[C:43]([O:45][CH2:46][CH3:47])=[O:44])(C1C=CC(C)=CC=1)(=O)=O>O>[CH2:1]([NH:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([O:24][CH:42]([C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH3:48])=[O:23])=[CH:25][CH:26]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16] | null | O | CCO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
644,272 | COC(=N)c1ccc(O)cc1 | Cl | null | null | ord_dataset-c975a50a7600448fabd558f4a94a3e29 | 2004-01-01T00:08:00 | true | Ethyl 3-amino-4-cyclohexylaminobenzoate (130 g) obtained in Example 1, Step 3, and methyl 4-hydroxybenzimidate hydrochloride (139 g) were added to methyl alcohol (1500 ml), and the mixture was refluxed under heating for 4 hr. The reaction mixture was allowed to cool and the precipitated crystals were collected by filtration to give the title compound (131 g, yield 72%). | CCOC(=O)c1ccc2c(c1)nc(-c1ccc(O)cc1)n2C1CCCCC1 | null | CCOC(=O)c1ccc2c(c1)nc(-c1ccc(Oc3cccc(Br)c3)cc1)n2C1CCCCC1 | null | null | BrC1C=C(C=CC=1)[O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:16]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[C:15]3[CH:23]=[CH:24][C:25]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:26][C:14]=3[N:13]=2)=[CH:8][CH:7]=1.Cl.OC1C=CC(C(=N)OC)=CC=1>CO>[CH:17]1([N:16]2[C:15]3[CH:23]=[CH:24][C:25]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:26][C:14]=3[N:13]=[C:12]2[C:9]2[CH:10]=[CH:11][C:6]([OH:5])=[CH:7][CH:8]=2)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1 | null | CO | null | null | null | 143.6 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
898,550 | CC[SiH](CC)CC | O=C([O-])[O-] | [Na+] | null | ord_dataset-de6bce51790e4004a27e1a8f2bcc7ded | 2009-01-01T00:08:00 | true | rac-6-Chloro-3-hydroxy-3-pyridin-3-yl-1,3-dihydro-indol-2-one (0.27 g, 1.0 mmol) (from Example 39a supra) was suspended in a mixture of triethylsilane (0.49 mL, 3.0 mmol) (Aldrich) and trifluoroacetic acid (1.77 g, 15.0 mmol) (Aldrich) and heated in an 78° C. oil bath for overweekend. After cooling to room temperature, the mixture was diluted with ethyl acetate and treated with solid sodium carbonate (1.0 g). After stirring for 30 minutes, mixture was extracted with water and brine. Aqueous layers were back washed with ethyl acetate. Organic layers were combined, dried (Na2SO4), filtered and concentrated to obtain rac-6-chloro-3-pyridin-3-yl-1,3-dihydro-indol-2-one (Yield 0.1 g, 40%) as yellow oil and carried out for the next step without further purification. | O=C1Nc2cc(Cl)ccc2C1c1cccnc1 | null | O=C1Nc2cc(Cl)ccc2C1(O)c1cccnc1 | null | null | [Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](O)([C:12]3[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]([C:12]3[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1 | 0.5 | CCOC(C)=O | O=C(O)C(F)(F)F | null | 78 | null | 40.9 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,189,048 | O=C([O-])[O-] | [Na+] | null | null | ord_dataset-9cd817a75dfc4fe7ad19d4232772d5ff | 2012-01-01T00:07:00 | true | 3.48 g (11.2 mmol) of 3-methyl-1-oxy-5-(3-trifluoromethyl-phenyl)-pyridine-2-carboxylic acid methyl ester [prepared from 3-methyl-5-(3-trifluoromethyl-phenyl)-pyridine-2-carboxylic acid methyl ester (intermediate 1A) by reaction with 3-chloro-perbenzoic acid in analogy to the procedure described for the preparation of intermediate 1C] was added at RT while stirring to 20.4 ml=34.25 g (223.3 mmol) of phosphorus oxychloride and the reaction mixture was warmed up to 50° C. After 2 hours, it was cooled down to RT and poured into crashed ice. This solution was carefully neutralized with solid sodium carbonate and extracted twice with EtOAc; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (heptane/CH2Cl2 1:1 to 0:1) to give 2.52 g (68%) 6-chloro-3-methyl-5-(3-trifluoromethyl-phenyl)-pyridine-2-carboxylic acid methyl ester as light yellow oil; [MS: 330.0 (MH+, 1Cl)] and 1.10 g (30%) 4-chloro-3-methyl-5-(3-trifluoromethyl-phenyl)-pyridine-2-carboxylic acid methyl ester as colorless solid. MS: 330.0 (MH+, 1Cl). | COC(=O)c1nc(Cl)c(-c2cccc(C(F)(F)F)c2)cc1C | null | O=C(OO)c1cccc(Cl)c1 | COC(=O)c1ncc(-c2cccc(C(F)(F)F)c2)cc1C | null | [CH3:1][O:2][C:3]([C:5]1[C:10]([CH3:11])=[CH:9][C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)=[CH:7][N:6]=1)=[O:4].[Cl:22]C1C=CC=C(C(OO)=O)C=1.P(Cl)(Cl)(Cl)=O.C(=O)([O-])[O-].[Na+].[Na+]>>[CH3:1][O:2][C:3]([C:5]1[C:10]([CH3:11])=[CH:9][C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)=[C:7]([Cl:22])[N:6]=1)=[O:4] | 2 | O=P(Cl)(Cl)Cl | null | null | 50 | null | 68 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
493,057 | null | null | null | null | ord_dataset-3f9174c7efcb4f31becbd3516cde9572 | 2001-01-01T00:02:00 | true | (Step 2) In 85 ml of dry tetrahydrofuran was dissolved 17 g of 2,4-dichloro-6-phenyl-1,3,5-triazine. To this solution on an ice-water bath was added 135 ml of 1M methylmagnesium bromide-tetrahydrofuran dropwise over about 30 minutes. After completion of dropwise addition, the mixture was stirred at room temperature for 2 hours. This reaction mixture was poured into iced water and extracted with ethyl acetate. The extract was washed with water, dried over MgSO4, and concentrated. The residue was purified with silica gel column chromatography to provide 3.6 g of the title compound as white crystals. | Cc1nc(Cl)nc(-c2ccccc2)n1 | null | Clc1nc(Cl)nc(-c2ccccc2)n1 | C[Mg]Br | null | [Cl:1][C:2]1[N:7]=[C:6](Cl)[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1.[CH3:15][Mg]Br.O1CCCC1.O>O1CCCC1>[Cl:1][C:2]1[N:7]=[C:6]([CH3:15])[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1 | 2 | C1CCOC1 | O | null | 25 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,584,052 | CN(C)C(On1nnc2ccccc21)=[N+](C)C | Cl | F[B-](F)(F)F | null | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | 2015-01-01T00:05:00 | true | The mixture of step D product, 2-20-e, (2.5 g, 7.7 mmol), ethyl 2-aminoacetate hydrochloride (1.29 g, 9.3 mmol), TBTU (2.98 g, 9.3 mmol), DIPEA (2.0 g, 15.5 mmol) in DMSO (20 mL) and stirred at the ambient temperature overnight. Then the reaction mixture was added ice-water (40 mL), extracted with DCM (30 mL×2). The organic phase was concentrated to give a residue, which was purified by column chromatography with DCM:MeOH=150:1 to obtain 2-20 (330 mg, 11%). 1H NMR (300 MHz, DMSO-d6): δ 1.18-1.22 (t, J=6 Hz, 3H), 4.0-4.02 (d, J=6 Hz, 2H), 4.11-4.14 (q, J=6.0 Hz, 2H), 5.0-5.02 (d, J=6.0 Hz, 1H), 7.48-7.57 (m, 4H), 7.87 (m, 3H), 8.55 (br s, 1H), 9.48 (m, 1H), 9.87 (br s, 1H), 13.54 (br s, 1H). LC-MS: (M+H)+ 409. | CCOC(=O)CNC(=O)c1ncc(C(=O)NCc2cccc3ccccc23)c(O)n1 | null | CCOC(=O)CN | O=C(O)c1ncc(C(=O)NCc2cccc3ccccc23)c(O)n1 | null | [OH:1][C:2]1[C:7]([C:8](=[O:21])[NH:9][CH2:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13][CH:12]=2)=[CH:6][N:5]=[C:4]([C:22]([OH:24])=O)[N:3]=1.Cl.[NH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CS(C)=O>[CH2:31]([O:30][C:28](=[O:29])[CH2:27][NH:26][C:22]([C:4]1[N:3]=[C:2]([OH:1])[C:7]([C:8](=[O:21])[NH:9][CH2:10][C:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:18]=[CH:19][CH:20]=2)=[CH:6][N:5]=1)=[O:24])[CH3:32] | null | CCN(C(C)C)C(C)C | CS(C)=O | null | 0 | null | 10.5 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
509,389 | [Pd] | null | null | null | ord_dataset-85c00026681b46f89ef8634d2b8618c3 | 2001-01-01T00:07:00 | true | To a suspension of 10% palladium on carbon (1.5 g) in ethyl acetate (200 mL) at room temperature under argon was added a solutioin of 2-(1,4-Dioxaspiro[4.5]dec-7-en-8-yl)benzonitrile (8.9 g, 36.7 mmol) in ethyl acetate (50 mL). Hydrogen gas was then bubbled into the reaction mixture until all the starting material was consumed. The reaction was filtered through celite to remove the catalyst and the solution concentrated to give the product as a colorless oil. | N#Cc1ccccc1C1CCC2(CC1)OCCO2 | null | N#Cc1ccccc1C1=CCC2(CC1)OCCO2 | null | null | [O:1]1[C:5]2([CH2:10][CH2:9][C:8]([C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[C:13]#[N:14])=[CH:7][CH2:6]2)[O:4][CH2:3][CH2:2]1>[Pd].C(OCC)(=O)C>[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[C:13]#[N:14])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1 | null | CCOC(C)=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 |
348,242 | [Co] | null | null | null | ord_dataset-66f304805e5d47fc8d3c722b1bd8dfa2 | 1996-01-01T00:12:00 | true | 30 g of 91.7% pure 2-chloro-5-cyanopyridine were hydrogenated in 100 ml of methylformate using 7 g of Raney cobalt analogously to Example 2. 2-Chloro-5-(formylaminomethyl)pyridine was obtained in a yield of 92.6% of theory, in addition to 2.9% of theory of 2-chloro-5-(aminomethyl)pyridine. | NCc1ccc(Cl)nc1 | O=CNCc1ccc(Cl)nc1 | N#Cc1ccc(Cl)nc1 | COC=O | null | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][N:3]=1.[CH3:10][O:11]C=O>[Co]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][CH:10]=[O:11])=[CH:4][N:3]=1.[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH2:9])=[CH:4][N:3]=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 |
1,280,084 | null | null | null | null | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | 2013-01-01T00:04:00 | true | As described for example 29e, 5-[3-(4-fluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-pyridine-2-carboxylic acid ethyl ester (75 mg, 0.2 mmol) was converted, using 4-aminotetrahydropyran instead of isopropylamine, to the title compound (9 mg, 10%), which was obtained as a colourless gum. MS: m/e=428.3 [M+H]+. | O=C(NC1CCOCC1)c1ccc(OCc2c(-c3ccc(F)cc3)noc2CO)cn1 | null | CCOC(=O)c1ccc(OCc2c(-c3ccc(F)cc3)noc2CO)cn1 | NC1CCOCC1 | null | C(O[C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[C:15]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)=[N:16][O:17][C:18]=2[CH2:19][OH:20])=[CH:8][N:7]=1)=[O:5])C.[NH2:28][CH:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1>>[O:32]1[CH2:33][CH2:34][CH:29]([NH:28][C:4]([C:6]2[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]3[C:15]([C:21]4[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=4)=[N:16][O:17][C:18]=3[CH2:19][OH:20])=[CH:8][N:7]=2)=[O:5])[CH2:30][CH2:31]1 | null | null | null | null | null | null | 10 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,059,202 | CCCC[N+](CCCC)(CCCC)CCCC | null | null | null | ord_dataset-373415d3e0e54004837cf4831e67666f | 2011-01-01T00:05:00 | true | Tetrabutyl-ammonium 2-[(3aR,4R,6R,6aR)-6-(6-chloro-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-ethanesulfonate (250.0 mg, 0.0003481 mol) was dissolved in methylene chloride (5.00 mL, 0.0780 mol) and N,N-dimethylformamide (100.0 μL, 0.001292 mol). Thionyl chloride (228 μL, 0.00313 mol) was added and the reaction was stirred at 0° C. for 45 minutes, concentrated in vacuo to dryness and followed by azeotroping with toluene. The residue was purified by flash chromatography (10% THF in DCM) to yield product (115 mg, 78%). | CC1(C)O[C@@H]2[C@H](O1)[C@@H](CCS(=O)(=O)Cl)O[C@H]2n1cnc2c(Cl)ncnc21 | null | ClCCl | CC1(C)O[C@@H]2[C@H](O1)[C@@H](CCS(=O)(=O)[O-])O[C@H]2n1cnc2c(Cl)ncnc21 | null | [Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@H:11]1[C@@H:15]2[O:16][C:17]([CH3:20])([CH3:19])[O:18][C@@H:14]2[C@@H:13]([CH2:21][CH2:22][S:23]([O-:26])(=O)=[O:24])[O:12]1.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)[Cl:45].CN(C)C=O.S(Cl)(Cl)=O>>[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@H:11]1[C@@H:15]2[O:16][C:17]([CH3:20])([CH3:19])[O:18][C@@H:14]2[C@@H:13]([CH2:21][CH2:22][S:23]([Cl:45])(=[O:26])=[O:24])[O:12]1 | 0.75 | CN(C)C=O | O=S(Cl)Cl | null | 0 | 78.1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
988,202 | CC(C)N=C=NC(C)C | null | null | null | ord_dataset-35b56288528641309a040cc2b6710b61 | 2010-01-01T00:08:00 | true | 0.16 mmol of 2-phenoxymethyl-1-(4-trifluoromethoxy-benzyl)-1H-benzoimidazole-5-carboxylic acid were dissolved in 1 ml THF with 1 eq. DIC. After 15 min 1.5 eq of butylamine was added and the reaction stirred at room temperature for 16 h. The crude material was purified via reversed phase preparative HPLC. MS(ISP) 498.3 (M+H)+. | CCCCNC(=O)c1ccc2c(c1)nc(COc1ccccc1)n2Cc1ccc(OC(F)(F)F)cc1 | null | CCCCN | O=C(O)c1ccc2c(c1)nc(COc1ccccc1)n2Cc1ccc(OC(F)(F)F)cc1 | null | [O:1]([CH2:8][C:9]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=2)[C:12]2[CH:26]=[CH:27][C:28]([C:30]([OH:32])=O)=[CH:29][C:11]=2[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)N=C=NC(C)C.[CH2:42]([NH2:46])[CH2:43][CH2:44][CH3:45]>C1COCC1>[CH2:42]([NH:46][C:30]([C:28]1[CH:27]=[CH:26][C:12]2[N:13]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]([F:23])([F:25])[F:24])=[CH:17][CH:16]=3)[C:9]([CH2:8][O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[N:10][C:11]=2[CH:29]=1)=[O:32])[CH2:43][CH2:44][CH3:45] | 16 | C1CCOC1 | null | null | 25 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,258,943 | CC(=O)O[BH-](OC(C)=O)OC(C)=O | [Na+] | null | null | ord_dataset-266f60b4555945d6afb2d2bdf5fa04e0 | 2013-01-01T00:02:00 | true | 65 mg (53%) of target compound was obtained by using a method same as in Example 1 by using 3-(5-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-3-yl)propanal (75 mg, 0.245 mmol), 1-(2-fluorophenyl)piperazine (44 mg, 0.245 mmol), DIPEA (0.064 mL, 0.368 mmol) and NaBH(OAc)3 (156 mg, 0.735 mmol). | COc1ccc(-c2cc(CCCN3CCN(c4ccccc4F)CC3)nn2-c2ccccc2)cc1 | null | Fc1ccccc1N1CCNCC1 | COc1ccc(-c2cc(CCC=O)nn2-c2ccccc2)cc1 | null | [CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:12]=[C:11]([CH2:20][CH2:21][CH:22]=O)[CH:10]=2)=[CH:5][CH:4]=1.[F:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1.CCN(C(C)C)C(C)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[F:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[N:31]1[CH2:36][CH2:35][N:34]([CH2:22][CH2:21][CH2:20][C:11]2[CH:10]=[C:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[N:13]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:12]=2)[CH2:33][CH2:32]1 | null | CCN(C(C)C)C(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 |
1,115,050 | C[Si](C)(C)I | null | null | null | ord_dataset-4226e9b4f9f845db967ed997270dcafc | 2011-01-01T00:12:00 | true | A mixture of 1 mmol of 7-methoxy-2,3,6′,7′-tetrahydro-5′H-spiro[chromene-4,8′-imidazo[1,5-a]pyridine] and 5 ml of trimethylsilyl iodide in 20 ml of acetonitrile is heated at reflux for 24 hours. 5 ml of methanol are added cautiously and the mixture is heated at reflux for a further 30 minutes. The reaction mixture is evaporated. From the residue the title compound is identified by means of flash chromatography (SiO2 60F) on the basis of the Rf value. | Oc1ccc2c(c1)OCCC21CCCn2cncc21 | null | COc1ccc2c(c1)OCCC21CCCn2cncc21 | null | null | C[O:2][C:3]1[CH:8]=[C:7]2[O:9][CH2:10][CH2:11][C:12]3([CH2:17][CH2:16][CH2:15][N:14]4[CH:18]=[N:19][CH:20]=[C:13]34)[C:6]2=[CH:5][CH:4]=1.C[Si](I)(C)C.CO>C(#N)C>[CH:20]1[N:19]=[CH:18][N:14]2[CH2:15][CH2:16][CH2:17][C:12]3([C:6]4[C:7](=[CH:8][C:3]([OH:2])=[CH:4][CH:5]=4)[O:9][CH2:10][CH2:11]3)[C:13]=12 | null | CC#N | CO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,225,998 | null | null | null | null | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | 2012-01-01T00:11:00 | true | Ethyl N-(6-chloro-2-methoxyquinoxalin-3-yl)carbamate and 1-(4-fluorophenyl)piperazine were reacted by the same way with the example 22 to obtain the titled compound (yield, 77%). 1H NMR (300 MHz, CDCl3): δ 3.13-3.20 (m, 4H), 3.77 (s, 3H), 4.14 (s, 4H), 6.88-7.02 (m, 4H), 7.20-7.24 (m, 1H), 7.36-7.44 (m, 1H), 7.50-7.67 (m, 1H), 7.80 (s, 1H). | COc1nc2ccc(Cl)cc2nc1NC(=O)N1CCN(c2ccc(F)cc2)CC1 | null | CCOC(=O)Nc1nc2cc(Cl)ccc2nc1OC | Fc1ccc(N2CCNCC2)cc1 | null | [Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([O:12][CH3:13])[C:6]([NH:14][C:15](=[O:19])OCC)=[N:5]2.[F:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[CH:23][CH:22]=1>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([O:12][CH3:13])[C:6]([NH:14][C:15]([N:30]1[CH2:29][CH2:28][N:27]([C:24]3[CH:23]=[CH:22][C:21]([F:20])=[CH:26][CH:25]=3)[CH2:32][CH2:31]1)=[O:19])=[N:5]2 | null | null | null | null | null | 77 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,765,739 | Cl | O=C([O-])[O-] | [K+] | null | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | 2016-01-01T00:09:00 | true | The title compound was prepared according to the procedure described in Intermediate-19 by using 3-fluoro-5-(trifluoromethyl)benzonitrile (2.00 g, 10.0 mmol), hydroxyl amine HCl (1.09 g, 15 mmol) and potassium carbonate (2.2 g, 15 mmol), ethanol (20 mL) to afford 0.900 g of the desired product. 1H NMR (300 MHz, DMSO d6): δ 6.10 (s, 2H), 7.69 (d, J=7.8 Hz, 1H), 7.79 (d, J=10.2 Hz, 1H), 10.03 (s, 1H); MS (m/z): 223.17 (M+H)+. | NC(=NO)c1cc(F)cc(C(F)(F)F)c1 | null | N#Cc1cc(F)cc(C(F)(F)F)c1 | NO | null | [F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)[C:5]#[N:6].Cl.[OH:15][NH2:16].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:9]=1)[C:5](=[N:16][OH:15])[NH2:6] | null | CCO | null | null | null | 40.5 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,281,243 | Cl | [K+] | null | null | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | 2013-01-01T00:04:00 | true | To a suspension of ethyl 5-methoxy-4-methyl-1H-indole-2-carboxylate (712 mg, 3.05 mmol) in toluene (10 mL) was added a 1 M solution of KOtBu in THF (3.97 mL, 3.97 mmol). The reaction mixture was stirred at room temperature for 5 min, methyl acrylate (825 μL, 9.15 mmol) was added. The reaction was stirred at reflux overnight and neutralized with 1 N HCl aqueous solution. The solid was collected and divided into three microwave vial. Each was added AcOH (8 mL) and H2O (1 mL), and heated at 180° C. for 15 min under microwave irradiation. The solvent was evaporated and the residue was purified by silica gel column chromatography to give the title compound as a yellow solid (500 mg). LCMS m/z=216.2 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 2.45 (s, 3H), 3.21 (t, J=6.5 Hz, 2H), 3.68 (s, 3H), 4.40 (t, J=6.2 Hz, 2H), 6.98 (s, 1H), 7.13 (d, J=9.0 Hz, 1H), 7.23 (d, J=9.0 Hz, 1H). | COc1ccc2c(cc3n2CCC3=O)c1C | null | CCOC(=O)c1cc2c(C)c(OC)ccc2[nH]1 | CC(C)(C)[O-] | null | [CH3:1][O:2][C:3]1[C:4]([CH3:17])=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([O:14]CC)=O)=[CH:6]2.[CH3:18][C:19]([O-])(C)C.[K+].C1COCC1.C(OC)(=O)C=C.Cl>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]2[N:8]3[CH2:18][CH2:19][C:12](=[O:14])[C:7]3=[CH:6][C:5]=2[C:4]=1[CH3:17] | 0.08 | C1CCOC1 | Cc1ccccc1 | C=CC(=O)OC | 25 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,116,339 | [Ni] | null | null | null | ord_dataset-4226e9b4f9f845db967ed997270dcafc | 2011-01-01T00:12:00 | true | 7-(Azidomethyl)quinoline (1.1 g, 5.7 mmol) was hydrogenated (1 atm) in the presence of Raney nickel (1.5 g, 26 mmol) in methanol (30 mL) until completion of the reaction. Catalyst was filtered off and the filtrate was concentrated under reduced pressure to a yellow oil which was dissolved in EtOAc (32 mL) and extracted with 1N hydrochloric acid (3×32 mL). The combined acidic aqueous phases were adjust to pH˜10 with 1N sodium hydroxide solution, and extracted with EtOAc (3×35 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure to afford a white solid (0.89 g, 94%). | NCc1ccc2cccnc2c1 | null | [N-]=[N+]=NCc1ccc2cccnc2c1 | null | null | [N:1]([CH2:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[CH:10][CH:11]=[N:12]2)=[CH:7][CH:6]=1)=[N+]=[N-]>[Ni].CO>[N:12]1[C:13]2[C:8](=[CH:7][CH:6]=[C:5]([CH2:4][NH2:1])[CH:14]=2)[CH:9]=[CH:10][CH:11]=1 | null | CO | null | null | null | null | 98.7 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
54,123 | [H-] | [Na+] | null | null | ord_dataset-053897d9b1744303b2fdfe3e796ca27b | 1979-01-01T00:04:00 | true | A solution of 4 g (14.7 mmoles) of 4a-(m-methoxyphenyl)-1,3-diketo-trans-decahydroisoquinoline in 50 ml of anhydrous dimethylformamide was added dropwise to 700 mg of a 55% suspension of sodium hydride in mineral oil in 50 ml of dimethylformamide at 70°. The reaction mixture was heated for 1 hour after the addition was complete and then cooled to 25°. 3,3-Dimethylallyl bromide (2.37 g, 15.8 mmoles) in 10 ml of dimethylformamide was added dropwise and the solution stirred overnight at 25°. After heating at 80° for 1 hour it was poured into water and extracted with ether to yield 4.74 g of N-(3,3-dimethylallyl)-4a-(m-methoxyphenyl)-1,3-diketo-cis-decahydroisoquinoline (oil), which was evaporatively distilled, bp 225° (0.005 mm). | COc1cccc([C@@]23CCCC[C@@H]2C(=O)N(CC=C(C)C)C(=O)C3)c1 | null | COc1cccc([C@@]23CCCC[C@H]2C(=O)NC(=O)C3)c1 | CC(C)=CCBr | null | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@@:9]23[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]2[C:13](=[O:19])[NH:12][C:11](=[O:20])[CH2:10]3)[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].[CH3:23][C:24]([CH3:28])=[CH:25][CH2:26]Br.O>CN(C)C=O>[CH3:23][C:24]([CH3:28])=[CH:25][CH2:26][N:12]1[C:11](=[O:20])[CH2:10][C@@:9]2([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)[C@H:14]([CH2:15][CH2:16][CH2:17][CH2:18]2)[C:13]1=[O:19] | 8 | O | CN(C)C=O | null | null | 94.4 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,513,447 | Cl[Pd]Cl | [Fe+2] | c1ccc(P(c2ccccc2)[c-]2cccc2)cc1 | null | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | 2014-01-01T00:12:00 | true | To (6-chloro-pyridin-3-yl)-{6-fluoro-5-[hydroxy-(4-methoxy-7-triisopropylsilanyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methyl]-pyridin-2-yl}-carbamic acid tert-butyl ester (72, 105 mg, 0.160 mmol) in 3.8 mL of toluene, [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) 1:1 complex with dichloromethane (13.0 mg, 0.016 mmol) is added under an atmosphere of nitrogen. The reaction is stirred for 5 minutes, then cyclopropylmagnesium bromide (17, 1.60 mL, 1.0 M in tetrahydrofuran, 1.60 mmol) is added slowly. The reaction is heated at 65° C. for 5 hours, then poured into water and extracted with ethyl acetate. The organic layer is dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material is purified by silica gel column chromatography, eluting with 20-100% ethyl acetate in hexane. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound (73, 70 mg). MS (ESI) [M+H+]+=563.6. | COc1ncnc2c1c(C(O)c1ccc(Nc3ccc(C4CC4)nc3)nc1F)cn2[Si](C(C)C)(C(C)C)C(C)C | null | COc1ncnc2c1c(C(O)c1ccc(N(C(=O)OC(C)(C)C)c3ccc(Cl)nc3)nc1F)cn2[Si](C(C)C)(C(C)C)C(C)C | Br[Mg]C1CC1 | null | C(OC(=O)[N:7]([C:38]1[CH:39]=[N:40][C:41](Cl)=[CH:42][CH:43]=1)[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([OH:36])[C:15]2[C:23]3[C:22]([O:24][CH3:25])=[N:21][CH:20]=[N:19][C:18]=3[N:17]([Si:26]([CH:33]([CH3:35])[CH3:34])([CH:30]([CH3:32])[CH3:31])[CH:27]([CH3:29])[CH3:28])[CH:16]=2)=[C:10]([F:37])[N:9]=1)(C)(C)C.ClCCl.[CH:49]1([Mg]Br)[CH2:51][CH2:50]1.O>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:49]1([C:41]2[N:40]=[CH:39][C:38]([NH:7][C:8]3[N:9]=[C:10]([F:37])[C:11]([CH:14]([C:15]4[C:23]5[C:22]([O:24][CH3:25])=[N:21][CH:20]=[N:19][C:18]=5[N:17]([Si:26]([CH:33]([CH3:35])[CH3:34])([CH:27]([CH3:29])[CH3:28])[CH:30]([CH3:32])[CH3:31])[CH:16]=4)[OH:36])=[CH:12][CH:13]=3)=[CH:43][CH:42]=2)[CH2:51][CH2:50]1 | 0.08 | O | Cc1ccccc1 | ClCCl | 65 | null | 77.7 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,011,092 | [Li+] | [OH-] | null | null | ord_dataset-7448b89163bf426c9d9777809ce24cec | 2010-01-01T00:11:00 | true | A solution of lithium hydroxide monohydrate (2.32 g, 55.1 mmol) in water (100 mL) was added to a solution of methyl 3-{[2-fluoro-1-(fluoromethyl)ethyl]oxy}-5-[(phenylmethyl)oxy]benzoate (7.41 g, 22.0 mmol) in THF (200 mL) and the mixture allowed to stir at RT overnight. The THF was removed in vacuo and the resulting solution partitioned between water (100 mL) and ethyl acetate (250 mL). The ethyl acetate layer was separated, washed with brine and dried (MgSO4). The aqueous layer was then adjusted to pH 7 by addition of 1M hydrochloric acid and extracted with ethyl acetate (75 mL). The ethyl acetate layer was separated, washed with brine and dried (MgSO4). The ethyl acetate layers were combined and evaporated to give the required product (6.404 g). | O=C(O)c1cc(OCc2ccccc2)cc(OC(CF)CF)c1 | null | COC(=O)c1cc(OCc2ccccc2)cc(OC(CF)CF)c1 | null | null | O.[OH-].[Li+].[F:4][CH2:5][CH:6]([O:9][C:10]1[CH:11]=[C:12]([CH:17]=[C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:19]=1)[C:13]([O:15]C)=[O:14])[CH2:7][F:8]>O.C1COCC1>[F:4][CH2:5][CH:6]([O:9][C:10]1[CH:11]=[C:12]([CH:17]=[C:18]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:19]=1)[C:13]([OH:15])=[O:14])[CH2:7][F:8] | 8 | O | C1CCOC1 | null | 25 | 90.3 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
2,354 | ClP(Cl)(Cl)(Cl)Cl | null | null | null | ord_dataset-a0bc986c3cf848c2a1ea93b297d1ad89 | 1976-01-01T00:02:00 | true | A solution of N-methyl-p-carbmethoxybenzamide in chloroform was treated with phosphorus pentachloride to give E. Then E was reacted with p-carbmethoxybenzoyl hydrazine to yield dimethyl-4,4'-(4-methyl-1,2,4-triazol-3,5-diyl)dibenzoate, (F). Then IV was obtained by reacting F in a similar manner as in Example 1. | COC(=O)c1ccc(-c2nnc(-c3ccc(C(=O)OC)cc3)n2C)cc1 | null | COC(=O)c1ccc(C(=O)NN)cc1 | CNC(=O)c1ccc(C(=O)OC)cc1 | null | [CH3:1][NH:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:5]=1.P(Cl)(Cl)(Cl)(Cl)Cl.[C:21]([C:25]1[CH:34]=[CH:33][C:28]([C:29]([NH:31][NH2:32])=O)=[CH:27][CH:26]=1)([O:23][CH3:24])=[O:22]>C(Cl)(Cl)Cl>[CH3:13][O:12][C:10](=[O:11])[C:7]1[CH:8]=[CH:9][C:4]([C:3]2[N:2]([CH3:1])[C:29]([C:28]3[CH:33]=[CH:34][C:25]([C:21]([O:23][CH3:24])=[O:22])=[CH:26][CH:27]=3)=[N:31][N:32]=2)=[CH:5][CH:6]=1 | null | ClC(Cl)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 |
1,336,578 | Cl | N | [Na+] | null | ord_dataset-08852243bba44cb28769a5833f1515fe | 2013-01-01T00:09:00 | true | 20 mL ACN are added to 0.50 g (1.11 mmol) 3-(4-chlorophenyl)-6-chloropyridazine and 3.33 g (22.2 mmol) NaI before 189 μl fuming conc. HCl are added and the mixture is stirred at 80° C. for 4 h. The mixture is alkalised with aq. ammonia solution (32%) diluted with water and extracted with EtOAc. The org. phases are combined, dried with Na2SO4 and the solvent is removed in vacuo. The resulting crude product is triturated with TBME. | Clc1ccc(-c2ccc(I)nn2)cc1 | null | Clc1ccc(-c2ccc(Cl)nn2)cc1 | [I-] | null | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[N:10][C:11](Cl)=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.[Na+].[I-:16].Cl.N>O.C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[N:10][C:11]([I:16])=[CH:12][CH:13]=2)=[CH:4][CH:3]=1 | 4 | CC#N | O | null | 80 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,263,325 | C(=NC1CCCCC1)=NC1CCCCC1 | CN(C)c1ccccn1 | null | null | ord_dataset-266f60b4555945d6afb2d2bdf5fa04e0 | 2013-01-01T00:02:00 | true | A suspension of 1-(tert-butoxycarbonyl)-4-phenylpiperidine-4-carboxylic acid (3.8 g, 10.3 mmol) in a dichloromethane (5 mL) and toluene (30 mL) mixture was treated with 1,3-dicyclohexylcarbodiimide (2.96 g, 14.4 mmol) and stirred for 30 min. The suspension was cooled to 0° C. and treated with (R)-1-(3-bromo-5-(trifluoromethyl)phenyl)ethanol (2.79 g, 10.3 mmol) and dimethylaminopyridine (1.26 g, 10.3 mmol). The ice bath was removed and the suspension stirred at room temperature for 60 h. The reaction mixture was poured into pentane, filtered, and the solids washed several times with pentane. The filtrate was washed with 1 N hydrochloric acid (1×), water (2×), then 1 N sodium hydroxide, then brine (2×), dried over sodium sulfate, and concentrated. Flash chromatography on silica gel (12% ethyl acetate/hexanes) gave 4.8 g (84%) as a light yellow oil. 1H NMR (500 MHz, CDCl3) δ ppm 7.58 (s, 1H), 7.23-7.33 (m, 6H), 7.19 (s, 1H), 5.80 (q, J=6.6 Hz, 1H), 3.82-3.97 (m, 2H), 2.97-3.09 (m, 2H), 2.44-2.53 (m, 2H), 1.76-2.01 (m, 2H), 1.42 (s, 9H), 1.40 (m, 3H). Mass spec.: 558.06 (MH)+. | C[C@@H](OC(=O)C1(c2ccccc2)CCN(C(=O)OC(C)(C)C)CC1)c1cc(Br)cc(C(F)(F)F)c1 | null | CC(C)(C)OC(=O)N1CCC(C(=O)O)(c2ccccc2)CC1 | C[C@@H](O)c1cc(Br)cc(C(F)(F)F)c1 | null | [C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:14]([OH:16])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(N=C=NC2CCCCC2)CCCCC1.[Br:38][C:39]1[CH:40]=[C:41]([C@H:49](O)[CH3:50])[CH:42]=[C:43]([C:45]([F:48])([F:47])[F:46])[CH:44]=1.CN(C1C=CC=CN=1)C>C1(C)C=CC=CC=1.ClCCl>[C:17]1([C:11]2([C:14]([O:16][C@@H:49]([C:41]3[CH:42]=[C:43]([C:45]([F:46])([F:47])[F:48])[CH:44]=[C:39]([Br:38])[CH:40]=3)[CH3:50])=[O:15])[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1 | 0.5 | ClCCl | Cc1ccccc1 | null | 0 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,320,419 | Cl | null | null | null | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | 2013-01-01T00:07:00 | true | The title compound was prepared according to Method B and the experimentals described for compound 92 from 3-(chloromethyl)-2-(4-chlorophenyl)imidazo[1,2-a]pyridine hydrochloride and 2H-benzo[b][1,4]oxazin-3(4H)-one. M/e+ 390 for C22H17ClN3O2 (M+H)+; 1H-NMR (400 MHz, CDCl3) δ 8.32 (d, J=6.9 Hz, 1H), 7.61 (d, J=8.4 Hz, 2H), 7.53 (m, 3H), 7.19 (ddd, J=9.1, 6.9, 1,1 Hz, 1H), 6.82 (m, 3H), 6.48 (m, 1H), 6.26 (d, J=7.7 Hz, 1H), 5.68 (s, 2H), 4.60 (s, 2H) ppm. | O=C1COc2ccccc2N1Cc1c(-c2ccc(Cl)cc2)nc2ccccn12 | null | O=C1COc2ccccc2N1 | ClCc1c(-c2ccc(Cl)cc2)nc2ccccn12 | null | Cl.Cl[CH2:3][C:4]1[N:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]2=[N:6][C:5]=1[C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1.[O:20]1[CH2:25][C:24](=[O:26])[NH:23][C:22]2[CH:27]=[CH:28][CH:29]=[CH:30][C:21]1=2>>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([C:5]2[N:6]=[C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][N:8]3[C:4]=2[CH2:3][N:23]2[C:24](=[O:26])[CH2:25][O:20][C:21]3[CH:30]=[CH:29][CH:28]=[CH:27][C:22]2=3)=[CH:14][CH:15]=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 |
220,040 | Cl | [Na+] | null | null | ord_dataset-6cb04513a4a244c0b612b566096f4b3d | 1990-01-01T00:12:00 | true | A solution of 0.06 mol of N-(2-allylphenyl)phenylglycine, prepared as described by A. Padwa, H. L. Gingrich, and R. Lim in J. Org. Chem.,1982, 47, 2447-2456, and 0.066 mol of HCl in 100 mL of CH3OH is stirred at reflux for 8 hours. The solution is then cooled and treated with 0.066 mol of sodium bicarbonate. The solvent is removed by rotary evaporator, and the residue is dissolved in diethyl ether, filtered, dried over MgSO4, and filtered. The solvent is removed by rotary evaporator to give N-(2-allylphenyl)phenylglycine methyl ester. | C=CCc1ccccc1N(CC(=O)OC)c1ccccc1 | null | C=CCc1ccccc1N(CC(=O)O)c1ccccc1 | O=C([O-])O | null | [CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:11][C:12]([OH:14])=[O:13])[CH:2]=[CH2:3].Cl.[C:22](=O)(O)[O-].[Na+]>CO>[CH3:22][O:13][C:12](=[O:14])[CH2:11][N:10]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH2:1][CH:2]=[CH2:3] | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
49,342 | ClCCN1CCOCC1 | null | null | null | ord_dataset-0bb2e99daa66408fb8dbd6a0781d241c | 1978-01-01T00:12:00 | true | By substituting 3-piperazinopropyl chloride for the 1-chloro-2-morpholinoethane in the procedure of Example 5 and utilizing the 2-methyl-4H-pyrazolo[1,5-a]pyrazolo-[4',3':5,6]pyrido[3,4-e]pyrimidin-5(8H)-one product of Example 8, 2-methyl-4-(3-piperazino)propyl-4H-pyrazolo[1,5-a]-pyrazolo[4',3':5,6]pyrido[3,4-e]pyrimidin-5(8H)-one is obtained. | Cc1cc2n(CCCN3CCNCC3)c(=O)c3cnc4[nH]ncc4c3n2n1 | null | ClCCCN1CCNCC1 | Cc1cc2[nH]c(=O)c3cnc4[nH]ncc4c3n2n1 | null | [N:1]1([CH2:7][CH2:8][CH2:9]Cl)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.ClCCN1CCOCC1.[CH3:20][C:21]1[CH:37]=[C:24]2[NH:25][C:26](=[O:36])[C:27]3[CH:32]=[N:31][C:30]4[NH:33][N:34]=[CH:35][C:29]=4[C:28]=3[N:23]2[N:22]=1>>[CH3:20][C:21]1[CH:37]=[C:24]2[N:25]([CH2:9][CH2:8][CH2:7][N:1]3[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]3)[C:26](=[O:36])[C:27]3[CH:32]=[N:31][C:30]4[NH:33][N:34]=[CH:35][C:29]=4[C:28]=3[N:23]2[N:22]=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 |
951,032 | C[O-] | [Na+] | null | null | ord_dataset-3feb2a95f66e4706a4a50c977ccd9bf8 | 2010-01-01T00:04:00 | true | Prepared in analogy to that of Example 1(e) from 2,3-dichloro-7-cyano-1-(2-fluoro-benzyl)-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester, glycine and NaOMe/HOMe. The title compound, ESI MS (m/z): 437 (M+H)+. | N#Cc1nc(C(=O)NCC(=O)O)c(O)c2c(Cl)c(Cl)n(Cc3ccccc3F)c12 | null | CCOC(=O)c1nc(C#N)c2c(c1O)c(Cl)c(Cl)n2Cc1ccccc1F | NCC(=O)O | null | C(O[C:4]([C:6]1[C:7]([OH:27])=[C:8]2[C:16]([Cl:17])=[C:15]([Cl:18])[N:14]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[F:26])[C:9]2=[C:10]([C:12]#[N:13])[N:11]=1)=[O:5])C.[NH2:28][CH2:29][C:30]([OH:32])=[O:31].C[O-].[Na+].CO>>[Cl:18][C:15]1[N:14]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[F:26])[C:9]2=[C:10]([C:12]#[N:13])[N:11]=[C:6]([C:4]([NH:28][CH2:29][C:30]([OH:32])=[O:31])=[O:5])[C:7]([OH:27])=[C:8]2[C:16]=1[Cl:17] | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,284,438 | CCCC[N+](CCCC)(CCCC)CCCC | [F-] | null | null | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | 2013-01-01T00:04:00 | true | To a solution of rac-2-chloro-4-[(4R,5S)-4-(tert-butyldimethylsilyloxy)-3,3,5-trimethyl-2-oxopyrrolidin-1-yl]benzonitrile (121 mg) in THF (5.5 mL) was added tetrabutylammonium fluoride-THF solution (0.5 mL, 1 mol/L), and the mixture was stirred at room temperature for 7 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=10/1→1/2) to give the title compound as a colorless solid (yield: 47.2 mg, 55%). | C[C@H]1[C@H](O)C(C)(C)C(=O)N1c1ccc(C#N)c(Cl)c1 | null | C[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C(C)(C)C(=O)N1c1ccc(C#N)c(Cl)c1 | null | null | [Cl:1][C:2]1[CH:9]=[C:8]([N:10]2[C@@H:14]([CH3:15])[C@H:13]([O:16][Si](C(C)(C)C)(C)C)[C:12]([CH3:25])([CH3:24])[C:11]2=[O:26])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.O>C1COCC1>[Cl:1][C:2]1[CH:9]=[C:8]([N:10]2[C@@H:14]([CH3:15])[C@H:13]([OH:16])[C:12]([CH3:25])([CH3:24])[C:11]2=[O:26])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5] | 7 | O | C1CCOC1 | null | 25 | 55 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
641,110 | C[Si](C)(C)C=[N+]=[N-] | null | null | null | ord_dataset-1c0bae7388cf460091d56129e95b3145 | 2004-01-01T00:06:00 | true | To a stirred solution of 4-hydroxy-3-nitrobenzoic acid (3.00 g, 0.0164 mol) in MeOH-benzene (1:4, v/v) was added dropwise 2.0 M-n-hexane solution of TMSCHN2 (8.2 mL, 0.0164 mol) at room temp. After the resulting solution was stirred for 4 hr at room temp, the mixture was evaporated off in vacuo. The oily residue was chromatographed on silica-gel with CHCl3 as eluent to afford 4.23 g (79%) methyl 4-hydroxy-3-nitrobenzoate as a pale yellow crystalline material. | COC(=O)c1ccc(O)c([N+](=O)[O-])c1 | null | O=C(O)c1ccc(O)c([N+](=O)[O-])c1 | CCCCCC | null | [OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[CH3:14]CCCCC.[Si](C=[N+]=[N-])(C)(C)C>CO.C1C=CC=CC=1>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:14])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12] | 4 | CO | c1ccccc1 | null | 25 | 79 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
537,075 | [Li+] | [OH-] | null | null | ord_dataset-1884c7bf3d544afdb8d17b5d41b90a27 | 2002-01-01T00:03:00 | true | To a suspension of 0.30 g (0.87 mmol) of ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl)ethynyl]benzoate (Compound 1) in 4 ml of THF and 2 ml of ethanol was added 2 ml (2 mmol) of LiOH (1N aqueous solution). The reaction mixture was stirred at room temperature for 4 hours, concentrated in vacuo to near dryness, partitioned between EtOAc and 1 ml of water and acidified to pH 4 with 10% HCl. The aqueous layer was extracted with EtOAc and then the organic layer was dried over Na2SO4 and concentrated in vacuo to give the title compound as a light yellow solid. | CC1(C)CCC(=O)c2ccc(C#Cc3ccc(C(=O)O)cc3)cc21 | null | CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3=O)cc1 | null | null | [CH3:1][C:2]1([CH3:26])[C:11]2[CH:10]=[C:9]([C:12]#[C:13][C:14]3[CH:24]=[CH:23][C:17]([C:18]([O:20]CC)=[O:19])=[CH:16][CH:15]=3)[CH:8]=[CH:7][C:6]=2[C:5](=[O:25])[CH2:4][CH2:3]1.[Li+].[OH-]>C1COCC1.C(O)C>[CH3:1][C:2]1([CH3:26])[C:11]2[CH:10]=[C:9]([C:12]#[C:13][C:14]3[CH:15]=[CH:16][C:17]([C:18]([OH:20])=[O:19])=[CH:23][CH:24]=3)[CH:8]=[CH:7][C:6]=2[C:5](=[O:25])[CH2:4][CH2:3]1 | 4 | C1CCOC1 | CCO | null | 25 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
484,777 | CCCC[N+](CCCC)(CCCC)CCCC | [F-] | null | null | ord_dataset-cb5c1a9eddff4790b1bd650617c32d34 | 2000-01-01T00:11:00 | true | Under argon atmosphere, tetrahydrofuran solution of tetrabutylammonium fluoride (1.0M, 2.27 ml, 2.27 mmol) was added dropwise to tetrahydrofuran solution (35 ml) of (3RS,4RS)-4-(4-t-butyldimethylsilyloxyphenyl)-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methylthiochroman (856 mg, 1.51 mmol) at 0° C. and the resulting mixture was stirred for 2 hours. After adding water, the reaction solution was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate and then distilled under reduced pressure to remove the solvent. The crude product thus obtained was purified with silica gel column chromatography (ethyl acetate:hexane=1:2) to obtain 682 mg (yield: 100%) of the title compound. | COCOc1ccc(C2(C)CSc3cc(OCOC)ccc3C2c2ccc(O)cc2)cc1 | null | COCOc1ccc(C2(C)CSc3cc(OCOC)ccc3C2c2ccc(O[Si](C)(C)C(C)(C)C)cc2)cc1 | null | null | O1CCCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:31][C:32]1[CH:37]=[CH:36][C:35]([CH:38]2[C:47]3[C:42](=[CH:43][C:44]([O:48][CH2:49][O:50][CH3:51])=[CH:45][CH:46]=3)[S:41][CH2:40][C:39]2([C:53]2[CH:58]=[CH:57][C:56]([O:59][CH2:60][O:61][CH3:62])=[CH:55][CH:54]=2)[CH3:52])=[CH:34][CH:33]=1)(C(C)(C)C)(C)C>O>[OH:31][C:32]1[CH:37]=[CH:36][C:35]([CH:38]2[C:47]3[C:42](=[CH:43][C:44]([O:48][CH2:49][O:50][CH3:51])=[CH:45][CH:46]=3)[S:41][CH2:40][C:39]2([C:53]2[CH:54]=[CH:55][C:56]([O:59][CH2:60][O:61][CH3:62])=[CH:57][CH:58]=2)[CH3:52])=[CH:34][CH:33]=1 | 2 | C1CCOC1 | O | null | null | null | 99.8 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
797,280 | CC(C)[N-]C(C)C | [Li+] | null | null | ord_dataset-a2d74266062e4398bc26c4f876903ab8 | 2007-01-01T00:11:00 | true | A solution of lithium diisopropylamide (2M in heptane, 16.9 ml) was added dropwise over 15 min to a stirred solution of 4-benzyl-morpholin-3-one (5.0 g, 26 mmol) and 3-fluorobenzaldehyde (3.55 g, 28.6 mmol) in dried tetrahydrofuran (60 ml) cooled to −70° C. under nitrogen atmosphere. After 1 h at −70° C., the reaction mixture was quenched with aqueous ammonium chloride (100 ml) and extracted with ethyl acetate (100 ml). The extracts were washed with 2M aqueous hydrochloric acid (2×50 ml), brine solution (100 ml) and dried over sodium sulphate. After filtration, the solution was evaporated and the residual oil purified by chromatography on silica eluting with ethyl acetate:hexane 70:30 then ethyl acetate to give diastereomer 1 (2R)-2-[(S)-(3-fluorophenyl)(hydroxy)methyl]-4-benzylmorpholin-3-one and (2S)-2-[(R)-(3-fluorophenyl)(hydroxy)methyl]-4-benzylmorpholin-3-one as a solid (3.8 g) followed by diastereomer 2 (2R)-2-[(R)-(3-fluorophenyl)(hydroxy)methyl]-4-benzylmorpholin-3-one and (2S)-2-[(S)-(3-fluorophenyl)(hydroxy)methyl]-4-benzylmorpholin-3-one as an oil (2.13 g). Diastereomer 1 was recrystallised from ethyl acetate (25 ml) n-hexane (100 ml) to give white needles (2.62 g, 32%). | O=C1[C@@H]([C@@H](O)c2cccc(F)c2)OCCN1Cc1ccccc1 | O=C1[C@H]([C@H](O)c2cccc(F)c2)OCCN1Cc1ccccc1 | O=Cc1cccc(F)c1 | O=C1COCCN1Cc1ccccc1 | null | C([N-]C(C)C)(C)C.[Li+].[CH2:9]([N:16]1[CH2:21][CH2:20][O:19][CH2:18][C:17]1=[O:22])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[F:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH:27]=[O:28]>O1CCCC1>[F:23][C:24]1[CH:25]=[C:26]([C@H:27]([OH:28])[C@H:18]2[O:19][CH2:20][CH2:21][N:16]([CH2:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:17]2=[O:22])[CH:29]=[CH:30][CH:31]=1.[F:23][C:24]1[CH:25]=[C:26]([C@@H:27]([OH:28])[C@@H:18]2[O:19][CH2:20][CH2:21][N:16]([CH2:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:17]2=[O:22])[CH:29]=[CH:30][CH:31]=1 | 1 | C1CCOC1 | null | null | -70 | 92.7 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,513,861 | null | null | null | null | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | 2014-01-01T00:12:00 | true | 3-Aminopicolinic acid (B-1) (30 g, 217 mmol, 1.0 eq) is suspended in formamide (75 mL, 1.88 mol, 8.66 eq). The resulting mixture is stirred at 140° C. for 1 h and at 170° C. for 1 h and then at 180° C. for an additional 1 h. The mixture is cooled to RT and filtered. The filter cake is washed with water, and dried in vacuo to afford the product, pyrido[3,2-d]pyrimidin-4-ol (B-2). | Oc1ncnc2cccnc12 | null | NC=O | Nc1cccnc1C(=O)O | null | [NH2:1][C:2]1[C:3]([C:8]([OH:10])=O)=[N:4][CH:5]=[CH:6][CH:7]=1.[CH:11]([NH2:13])=O>>[N:1]1[C:2]2[CH:7]=[CH:6][CH:5]=[N:4][C:3]=2[C:8]([OH:10])=[N:13][CH:11]=1 | 1 | null | null | null | 170 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,496,744 | null | null | null | null | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | 2014-01-01T00:10:00 | true | A mixture of triethyl orthoformate (4 mL) and (2R,6R,11S)-3-(1H-benzoimidazole-5-carbonyl)-N-hydroxy-6,11-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocine-8-carboxamidine (0.25 g) is stirred at 100° C. for 6 h. After cooling to room temperature, the mixture is concentrated and the residue is purified by HPLC on reversed phase (water/MeCN/NH3) to give the title compound as a white solid. | C[C@@H]1[C@H]2Cc3ccc(-c4ncon4)cc3[C@]1(C)CCN2C(=O)c1ccc2[nH]cnc2c1 | null | CCOC(OCC)OCC | C[C@@H]1[C@H]2Cc3ccc(C(=N)NO)cc3[C@]1(C)CCN2C(=O)c1ccc2[nH]cnc2c1 | null | [CH:1](OCC)(OCC)OCC.[NH:11]1[C:15]2[CH:16]=[CH:17][C:18]([C:20]([N:22]3[CH2:29][CH2:28][C@:27]4([CH3:32])[C@H:30]([CH3:31])[C@H:23]3[CH2:24][C:25]3[CH:36]=[CH:35][C:34]([C:37]([NH:39][OH:40])=[NH:38])=[CH:33][C:26]=34)=[O:21])=[CH:19][C:14]=2[N:13]=[CH:12]1>>[NH:11]1[C:15]2[CH:16]=[CH:17][C:18]([C:20]([N:22]3[CH2:29][CH2:28][C@:27]4([CH3:32])[C@H:30]([CH3:31])[C@H:23]3[CH2:24][C:25]3[CH:36]=[CH:35][C:34]([C:37]5[N:38]=[CH:1][O:40][N:39]=5)=[CH:33][C:26]=34)=[O:21])=[CH:19][C:14]=2[N:13]=[CH:12]1 | 6 | null | null | null | 100 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,238,473 | O=C([O-])O | [Na+] | null | null | ord_dataset-e96f5a2842f14e5380461c234100f05a | 2012-01-01T00:12:00 | true | In a glass tube, 250 mg of 1-(benzofuran-3-yl)-2-bromoethanone, 181 mg of 5-bromopyridin-2-ylamine and 105 mg of sodium hydrogencarbonate are dissolved in 15 ml of n-propanol. The tube is closed and heated at 80° C. for 20 h. After cooling, 20 ml of water are added and the reaction mixture is stirred for 1 hour at ambient temperature. A precipitate forms, and is recovered by filtration, washed with water and then with diisopropyl ether, and dried in a desiccator under reduced pressure. 250 mg of compound are obtained. | Brc1ccc2nc(-c3coc4ccccc34)cn2c1 | null | O=C(CBr)c1coc2ccccc12 | Nc1ccc(Br)cn1 | null | [Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.C(=O)([O-])O.[Na+].O.[O:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[C:17]([C:24](=O)[CH2:25]Br)=[CH:16]1>C(O)CC>[O:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[C:17]([C:24]2[N:8]=[C:5]3[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]3[CH:25]=2)=[CH:16]1 | 1 | O | CCCO | null | 80 | null | 76.3 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
293,466 | Cl | Cl[Sn]Cl | null | null | ord_dataset-b90b48a6c23149a1aa2d91b92b1a31e4 | 1994-01-01T00:07:00 | true | A solution of the above nitro mustard (XII; R=H) (2.51 g, 11 mmol) in 12 N HCl (25 mL) was treated portionwise at 25 ° C. with SnCl2.2H2O (9.9 g, 44 mmol), heated on a steam bath at 90° C. for 1 h, then evaporated to dryness under reduced pressure. The residue as shaken vigorously With a mixture of CH2Cl2, 2 N NH4OH and ice, and filtered through a celite pad. Workup of the organic layer gave essentially pure 3-[N-(2-chloroethyl) -N-ethylamino]aniline (XIII; R=H) (1.92 g, 88%) as an oil, which was used immediately. | CCN(CCCl)c1cccc(N)c1 | null | CCN(CCCl)c1cccc([N+](=O)[O-])c1 | null | null | [Cl:1][CH2:2][CH2:3][N:4]([CH2:14][CH3:15])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-])=O)[CH:6]=1.O.O.Cl[Sn]Cl>Cl>[Cl:1][CH2:2][CH2:3][N:4]([C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][CH:10]=1)[NH2:11])[CH2:14][CH3:15] | null | O | null | null | 90 | null | 88 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
361,339 | O=C([O-])[O-] | [K+] | null | null | ord_dataset-0b24d1f58a024ed7bc2bda95b2430c72 | 1997-01-01T00:04:00 | true | A mixture of methyl-17β-[3-(4-carboxyphenyl)propionyl]-estra-1,3,5(10)-triene-3-carboxylate (0.053 g, 0.11 mmoles), K2CO3 (50 mg, 0.36 mmoles), MeOH (9 ml) and H2O (1 ml) was refluxed under argon. Methanol was evaporated and the residue was acidified with dilute HCl. Extracted with EtOAc. The organic layer was washed with H2O, brine, dried and concentrated. The residue was chromatographed (silica gel) eluting with 1% MeOH in CH2Cl2 containing 1% HOAC to give the title compound as a white solid (40 mg, 80%), mp 285°-290° C. | C[C@]12CC[C@@H]3c4ccc(C(=O)O)cc4CC[C@H]3[C@@H]1CC[C@@H]2C(=O)CCc1ccc(C(=O)O)cc1 | null | COC(=O)c1ccc2c(c1)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](C(=O)CCc3ccc(C(=O)O)cc3)CC[C@@H]12 | null | null | C[O:2][C:3]([C:5]1[CH:22]=[CH:21][C:20]2[C@@H:19]3[C@H:10]([C@H:11]4[C@@:15]([CH2:17][CH2:18]3)([CH3:16])[C@@H:14]([C:23](=[O:35])[CH2:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]([C:32]([OH:34])=[O:33])=[CH:28][CH:27]=3)[CH2:13][CH2:12]4)[CH2:9][CH2:8][C:7]=2[CH:6]=1)=[O:4].C([O-])([O-])=O.[K+].[K+].CO>O>[C:32]([C:29]1[CH:28]=[CH:27][C:26]([CH2:25][CH2:24][C:23]([C@H:14]2[CH2:13][CH2:12][C@H:11]3[C@H:10]4[C@H:19]([CH2:18][CH2:17][C@:15]23[CH3:16])[C:20]2[CH:21]=[CH:22][C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]=2[CH2:8][CH2:9]4)=[O:35])=[CH:31][CH:30]=1)([OH:34])=[O:33] | null | O | CO | null | null | 79 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,690,398 | C[O-] | [Na+] | null | null | ord_dataset-c1e70ad912eb438f8d34b1dc681f809a | 2016-01-01T00:02:00 | true | 356 mg of sodium methanolate (6.60 mmol, 4.0 eq.) were dissolved in 10 mL of methanol. 403 mg of 5-(dimethylamino)-1-(2-fluorobenzyl)-1H-pyrazole-3-carbonitrile 1-11-1 (1.65 mmol, 1.0 eq.) were dissolved in 20 mL of methanol and added dropwise. The mixture was stirred for one hour at rt. 111.2 mg of ammonium chloride (2.08 mmol, 1.26 eq.) and 377 μL of 100% acetic acid (6.60 mmol, 4.0 eq.) were added and stirred under reflux for 24 hours. 111 mg of ammonium chloride (2.08 mmol, 1.26 eq.) and 377 μL of 100% acetic acid (6.60 mmol, 4.0 eq.) were added and stirred under reflux for 24 hours again. The mixture was concentrated under vacuo. The residue was suspended in acetonitrile and filtered off two times. The filter cakes were dissolved in DCM/methanol 1:1 and filtered over a silica column to provide 313 mg (1.19 mmol, 72.6%) of analytically pure target compound. | CN(C)c1cc(C(=N)N)nn1Cc1ccccc1F | Cl | [NH4+] | [Cl-] | CN(C)c1cc(C#N)nn1Cc1ccccc1F | C[O-].[Na+].[CH3:4][N:5]([CH3:21])[C:6]1[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])[N:9]=[C:8]([C:19]#[N:20])[CH:7]=1.[Cl-:22].[NH4+:23].C(O)(=O)C>CO>[ClH:22].[CH3:4][N:5]([CH3:21])[C:6]1[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])[N:9]=[C:8]([C:19](=[NH:23])[NH2:20])[CH:7]=1 | 1 | CO | CC(=O)O | null | 25 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
839,323 | CC(C)(C)OC(=O)N[C@@H]1Cc2ccccc2NC1=O | null | null | null | ord_dataset-074f86301ec5441ab3b52d902ac06949 | 2008-01-01T00:09:00 | true | The title compound was prepared from (S)-3-t-butyloxycarbonylamino-3,4-dihydrocarbostyril (prepared in Example 5) by the procedures described for the preparation of (R)-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril (Example 5) from (R)-3-t-butyloxycarbonylamino-3,4-dihydrocarbostyril. HPLC/MS [M+H]+, 340; [M+Na]+, 362. | O=C(N[C@H]1Cc2ccccc2NC1=O)c1cc2cc(Cl)ccc2[nH]1 | null | O=C(N[C@@H]1Cc2ccccc2NC1=O)c1cc2cc(Cl)ccc2[nH]1 | null | null | [Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([NH:13][C@@H:14]1[CH2:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][C:15]1=[O:24])=[O:12])=[CH:5]2.C(OC(N[C@@H]1CC2C(=CC=CC=2)NC1=O)=O)(C)(C)C>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([NH:13][C@H:14]1[CH2:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][C:15]1=[O:24])=[O:12])=[CH:5]2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
267,072 | null | null | null | null | ord_dataset-134cf2fa32ab464880d75db06c38f35a | 1993-01-01T00:05:00 | true | According to the procedure of Example 22C, 1-(4'-hydroxy-3',5'-dimethoxyphenyl)-1-hexene-3,5-dione is reacted with t-butylchlorodimethyl silane to afford 1-(4'-t-butyldimethylsilyloxy-3',5'-dimethoxyphenyl)-1-hexene-3,5-dione suitably pure for further use. | COc1cc(C=CC(=O)CC(C)=O)cc(OC)c1O[Si](C)(C)C(C)(C)C | null | COc1cc(C=CC(=O)CC(C)=O)cc(OC)c1O | CC(C)(C)[Si](C)(C)Cl | null | [OH:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([CH:10]=[CH:11][C:12](=[O:17])[CH2:13][C:14](=[O:16])[CH3:15])=[CH:4][C:3]=1[O:18][CH3:19].[C:20]([Si:24](Cl)([CH3:26])[CH3:25])([CH3:23])([CH3:22])[CH3:21]>>[Si:24]([O:1][C:2]1[C:3]([O:18][CH3:19])=[CH:4][C:5]([CH:10]=[CH:11][C:12](=[O:17])[CH2:13][C:14](=[O:16])[CH3:15])=[CH:6][C:7]=1[O:8][CH3:9])([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:26])[CH3:25] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
367,832 | null | null | null | null | ord_dataset-b18df02d6e9345faa0f2dae281a0870a | 1997-01-01T00:06:00 | true | Phthalic acid anhydride (15.1 g, 102 mmol) and 4-amino phenyl acetic acid (15.2 g, 102 mmol) were dissolved in acetic acid and heated at reflux for 1 hour. Upon cooling on an ice bath, the product crystallized. The solid was filtered off, washed with water, and dried under vacuum overnight. The yield of the title compound was 24.1 g (86%) as an off white solid. | O=C(O)Cc1ccc(N2C(=O)c3ccccc3C2=O)cc1 | null | Nc1ccc(CC(=O)O)cc1 | O=C1OC(=O)c2ccccc21 | null | [C:1]1(=[O:11])[O:6][C:4](=O)[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([OH:22])=[O:21])=[CH:15][CH:14]=1>C(O)(=O)C>[O:11]=[C:1]1[C:2]2[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:6])[N:12]1[C:13]1[CH:14]=[CH:15][C:16]([CH2:19][C:20]([OH:22])=[O:21])=[CH:17][CH:18]=1 | null | CC(=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 |
76,479 | null | null | null | null | ord_dataset-8868acadaee548d5802e504148fc3b63 | 1981-01-01T00:01:00 | true | To a stirred mixture of dry pyridine (15 ml) and dry methylene chloride (225 ml), chromic anhydride (9.0 g) is added in one portion, and the mixture is stirred for 15 minutes. A solution of 3-methylamino-4-phenoxy-5-sulfamylbenzyl alcohol (4.6 g; prepared as described in Example 5) in acetone (25 ml) is then added in one portion and the mixture is stirred for a further 15 minutes. The resulting inorganic precipitate is removed by filtration and the filtrate is evaporated in vacuo. The residue is extracted with diethyl ether (300 ml) and filtered to remove a small amount of insoluble material. The diethyl ether is removed in vacuo to yield crude 3-methylamino-4-phenoxy-5-sulfamylbenzaldehyde. After recrystallization from ethanol it is obtained with a melting point of 166°-167° C. | CNc1cc(C=O)cc(S(N)(=O)=O)c1Oc1ccccc1 | null | CNc1cc(CO)cc(S(N)(=O)=O)c1Oc1ccccc1 | null | null | N1C=CC=CC=1.C(Cl)Cl.[CH3:10][NH:11][C:12]1[CH:13]=[C:14]([CH:17]=[C:18]([S:27](=[O:30])(=[O:29])[NH2:28])[C:19]=1[O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:15][OH:16]>CC(C)=O>[CH3:10][NH:11][C:12]1[CH:13]=[C:14]([CH:17]=[C:18]([S:27](=[O:30])(=[O:29])[NH2:28])[C:19]=1[O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH:15]=[O:16] | 0.25 | ClCCl | CC(C)=O | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,600,305 | Cl[Ru](Cl)Cl | [Na+] | null | null | ord_dataset-e8c6a25568b64529b960953990e6921f | 2015-01-01T00:06:00 | true | A solution of (3aS,7S,7aS)-rel-6-(2,4-dimethoxy-benzyl)-7-(2-fluoro-phenyl)-7-methyl-hexahydro-2,4-dioxa-5-thia-6-aza-indene 5-oxide (7.24 g, 17.2 mmol) and sodium periodate (4.04 g, 18.9 mmol) in a mixture of ethyl acetate (60 ml), acetonitrile (60 ml) and cold water (99.6 ml) was treated with ruthenium(III) chloride (35.6 mg, 172 μmol). The reaction mixture was stirred at 23° C. for 30 minutes. For the workup, the reaction mixture was extracted with a saturated solution of sodium hydrogencarbonate, the aqueous layer re-extracted with ethyl acetate, and the combined organic layers were dried over sodium sulphate and evaporated. The residue was purified by flash chromatography on silica gel using a gradient of heptane and ethyl acetate=100:0 to 0:100 as the eluent. The (3aS,7S,7aS)-rel-6-(2,4-dimethoxy-benzyl)-7-(2-fluoro-phenyl)-7-methyl-hexahydro-2,4-dioxa-5-thia-6-aza-indene 5,5-dioxide (4.1 g, 55% yield) was obtained as a light yellow solid. MS (ISP): m/z=460.2 [M+Na]+. | COc1ccc(CN2[C@](C)(c3ccccc3F)[C@H]3COC[C@H]3OS2(=O)=O)c(OC)c1 | null | COc1ccc(CN2S(=O)O[C@@H]3COC[C@@H]3[C@@]2(C)c2ccccc2F)c(OC)c1 | [O-][I+3]([O-])([O-])[O-] | null | [CH3:1][O:2][C:3]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:4]=1[CH2:5][N:6]1[C@@:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])([CH3:15])[C@@H:13]2[C@@H:9]([CH2:10][O:11][CH2:12]2)[O:8][S:7]1=[O:23].I([O-])(=O)(=O)=[O:31].[Na+].C(#N)C.O>C(OCC)(=O)C.[Ru](Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:4]=1[CH2:5][N:6]1[C@@:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])([CH3:15])[C@@H:13]2[C@@H:9]([CH2:10][O:11][CH2:12]2)[O:8][S:7]1(=[O:31])=[O:23] | 0.5 | CCOC(C)=O | CC#N | O | 23 | 54.5 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
242,810 | [Pd] | null | null | null | ord_dataset-fa3b512e2d924b9b965301ebcba6853d | 1992-01-01T00:03:00 | true | To a solution of (2R,4R)-1-p-nitrobenzyloxycarbonyl-2-(2-methylaminocarbonylethyl)-4-hydroxypyrrolidine (1.52 g) in tetrahydrofuran (15 ml) and ethanol (15 ml), 10 palladium-carbon (228 mg) was added. The mixture was stirred at room temperature for 3.5 hours under an atmospheric pressure of hydrogen. The reaction mixture was filtered to remove the catalyst. The filtrate was concentrated, and the residue was combined with water, washed with dichloromethane and lyophilized to give (2R,4R)-2-(2-methylaminocarbonylethyl)-4-hydroxypyrrolidine. | CNC(=O)CC[C@@H]1C[C@@H](O)CN1 | null | CNC(=O)CC[C@@H]1C[C@@H](O)CN1C(=O)OCc1ccc([N+](=O)[O-])cc1 | [H][H] | null | [N+](C1C=CC(COC([N:12]2[CH2:16][C@H:15]([OH:17])[CH2:14][C@H:13]2[CH2:18][CH2:19][C:20]([NH:22][CH3:23])=[O:21])=O)=CC=1)([O-])=O.[H][H]>O1CCCC1.C(O)C.[C].[Pd]>[CH3:23][NH:22][C:20]([CH2:19][CH2:18][C@@H:13]1[CH2:14][C@@H:15]([OH:17])[CH2:16][NH:12]1)=[O:21] | null | C1CCOC1 | CCO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
440,713 | NN | null | null | null | ord_dataset-3e8f24b5bc8e4d8bb9b6e7e89a956e12 | 1999-01-01T00:09:00 | true | The compound was prepared in a manner analogous to the preparation of the compound of Example 48 from the compound of Example 50 (830 mg, 1 .54 mmol) and hydrazine monohydrate (0.23 ml, 4.62 mmol) to give the title compound (63 mg) as a white solid m.p. 161-162°. MS m/z 411 (M+H)+. | COc1cc(Nc2nccc(-c3ccc(OCCCN)cc3)n2)cc(OC)c1OC | null | COc1cc(Nc2nccc(-c3ccc(OCCCN4C(=O)c5ccccc5C4=O)cc3)n2)cc(OC)c1OC | null | null | C1(=O)[N:5]([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][N:19]=[C:18]([NH:22][C:23]4[CH:28]=[C:27]([O:29][CH3:30])[C:26]([O:31][CH3:32])=[C:25]([O:33][CH3:34])[CH:24]=4)[N:17]=3)=[CH:12][CH:11]=2)C(=O)C2=CC=CC=C12.O.NN>>[NH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][N:19]=[C:18]([NH:22][C:23]3[CH:28]=[C:27]([O:29][CH3:30])[C:26]([O:31][CH3:32])=[C:25]([O:33][CH3:34])[CH:24]=3)[N:17]=2)=[CH:12][CH:11]=1 | null | O | null | null | null | 28.4 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
735,607 | O=C([O-])[O-] | [K+] | null | null | ord_dataset-76dd1b78ee414d2da0ed30700ef026f7 | 2006-01-01T00:10:00 | true | N-{(1R,2R)-1-[(2-Acetoxyacetyl)amino]-2,3-dihydro-1H-inden-2-yl}-2,3-dichloro-4H-thieno[3,2-b]pyrrole-5-carboxamide (Example 6; 632 mg, 1.36 mmol) was dissolved in THF (10 mL), MeOH (10 mL) and K2CO3 (100 mg) were then added and the suspension stirred at ambient temperature for 16 hours. Water (50 mL) was added and the aqueous phase was extracted with EtOAc (3×30 mL). The combined organic phases were washed with water (2×50 mL), brine (50 mL) and dried (MgSO4). The solvent was removed by evaporation under reduced pressure, the crude product was triturated (EtOAc:isohexane, 1:10), filtered, washed with isohexane (5 mL) and dried to give the title compound (428 mg, 74%) as a white solid. | O=C(CO)N[C@@H]1c2ccccc2C[C@H]1NC(=O)c1cc2sc(Cl)c(Cl)c2[nH]1 | null | CC(=O)OCC(=O)N[C@@H]1c2ccccc2C[C@H]1NC(=O)c1cc2sc(Cl)c(Cl)c2[nH]1 | null | null | C([O:4][CH2:5][C:6]([NH:8][C@@H:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][C@H:10]1[NH:18][C:19]([C:21]1[NH:25][C:24]2[C:26]([Cl:30])=[C:27]([Cl:29])[S:28][C:23]=2[CH:22]=1)=[O:20])=[O:7])(=O)C.CO.C([O-])([O-])=O.[K+].[K+].O>C1COCC1>[Cl:29][C:27]1[S:28][C:23]2[CH:22]=[C:21]([C:19]([NH:18][C@@H:10]3[CH2:11][C:12]4[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=4)[C@H:9]3[NH:8][C:6](=[O:7])[CH2:5][OH:4])=[O:20])[NH:25][C:24]=2[C:26]=1[Cl:30] | 16 | O | CO | C1CCOC1 | 25 | 74.2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,475,036 | null | null | null | null | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | 2014-01-01T00:09:00 | true | The title compound is prepared from N-(1-cyano-piperidin-4-yl)-N-cyclopropyl-4-oxazol-5-yl-benzamide and N-hydroxy-tetrahydro-pyran-4-carboxamidine following a procedure analogous to that described in Example 1. LC (method 1): tR=1.10 min; Mass spectrum (ESI+): m/z=464 [M+H]+. | O=C(c1ccc(-c2cnco2)cc1)N(C1CC1)C1CCN(c2nc(C3CCOCC3)no2)CC1 | null | N#CN1CCC(N(C(=O)c2ccc(-c3cnco3)cc2)C2CC2)CC1 | N=C(NO)C1CCOCC1 | null | [C:1]([N:3]1[CH2:8][CH2:7][CH:6]([N:9]([CH:23]2[CH2:25][CH2:24]2)[C:10](=[O:22])[C:11]2[CH:16]=[CH:15][C:14]([C:17]3[O:21][CH:20]=[N:19][CH:18]=3)=[CH:13][CH:12]=2)[CH2:5][CH2:4]1)#[N:2].[OH:26][NH:27][C:28]([CH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1)=N>>[CH:23]1([N:9]([CH:6]2[CH2:5][CH2:4][N:3]([C:1]3[O:26][N:27]=[C:28]([CH:30]4[CH2:35][CH2:34][O:33][CH2:32][CH2:31]4)[N:2]=3)[CH2:8][CH2:7]2)[C:10](=[O:22])[C:11]2[CH:12]=[CH:13][C:14]([C:17]3[O:21][CH:20]=[N:19][CH:18]=3)=[CH:15][CH:16]=2)[CH2:25][CH2:24]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 |
271,909 | Cl | null | null | null | ord_dataset-347c0709d28a44dea43ca42052be4db3 | 1993-01-01T00:07:00 | true | To a solution of 4.9 g of cyclohexylamine and 5.4 g of triethylamine in 100 ml of methylenechloride, was added 5.8 g of 1,4-phenylenedipropionyl chloride under ice cooling with stirring. Stirring was continued for 3 hours at room temperature, and 500 ml of water was added to the reaction solution. Conc.-HCl was added to the mixture until aqueous layer became weak-acidic. The solid material precipitated was collected by filtration, washed with methylenechloride and water in that order, and dried, giving 7.4 g of N,N'-dicyclohexyl-1,4-phenylenedipropionamide. | O=C(CCc1ccc(CCC(=O)NC2CCCCC2)cc1)NC1CCCCC1 | null | NC1CCCCC1 | CCN(CC)CC | O=C(Cl)CCc1ccc(CCC(=O)Cl)cc1 | [CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([N:10]([CH2:13][CH3:14])CC)C.[C:15]1([CH2:26][CH2:27][C:28](Cl)=[O:29])[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23](Cl)=[O:24])=[CH:17][CH:16]=1.Cl>C(Cl)Cl.O>[CH:1]1([NH:7][C:28](=[O:29])[CH2:27][CH2:26][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]([NH:10][CH:13]3[CH2:14][CH2:3][CH2:2][CH2:1][CH2:6]3)=[O:24])=[CH:17][CH:16]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1 | 3 | O | ClCCl | null | null | null | 86 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,053,493 | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=P([O-])([O-])[O-] | [K+] | null | ord_dataset-373415d3e0e54004837cf4831e67666f | 2011-01-01T00:05:00 | true | Degassed N,N-dimethylformamide (0.37 mL) was added to 3-ethyl-1-(4-{1-ethyl-1-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenyl)-pentan-3-ol (Example 29; 30.6 mg, 0.0621 mmol), (5-bromo-pyridin-3-yl)acetic acid methyl ester (Example 24-(2); 21.1 mg, 0.0917 mmol), tetrakis(triphenylphosphine)palladium (0) (9.0 mg, 0.0078 mmol) and potassium phosphate (29.4 mg, 0.138 mmol). After replacement with nitrogen, the mixture was heated while stirring at an external temperature of 85 to 94° C. for three hours. Water was added to the reaction mixture, followed by extraction with diethyl ether. The extract was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate=1/1) to give the title compound (29.5 mg, 92%). | CCC(O)(CC)CCc1ccc(C(CC)(CC)c2ccc(-c3cncc(CC(=O)OC)c3)c(C)c2)cc1C | null | CCC(O)(CC)CCc1ccc(C(CC)(CC)c2ccc(B3OC(C)(C)C(C)(C)O3)c(C)c2)cc1C | COC(=O)Cc1cncc(Br)c1 | null | [CH2:1]([C:3]([OH:36])([CH2:34][CH3:35])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([CH2:31][CH3:32])([C:15]2[CH:20]=[CH:19][C:18](B3OC(C)(C)C(C)(C)O3)=[C:17]([CH3:30])[CH:16]=2)[CH2:13][CH3:14])=[CH:8][C:7]=1[CH3:33])[CH3:2].[CH3:37][O:38][C:39](=[O:48])[CH2:40][C:41]1[CH:42]=[N:43][CH:44]=[C:45](Br)[CH:46]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH3:37][O:38][C:39](=[O:48])[CH2:40][C:41]1[CH:42]=[N:43][CH:44]=[C:45]([C:18]2[CH:19]=[CH:20][C:15]([C:12]([CH2:13][CH3:14])([C:9]3[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][C:3]([CH2:34][CH3:35])([OH:36])[CH2:1][CH3:2])=[C:7]([CH3:33])[CH:8]=3)[CH2:31][CH3:32])=[CH:16][C:17]=2[CH3:30])[CH:46]=1 | 3 | O | null | null | 89.5 | 92.1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
547,043 | null | null | null | null | ord_dataset-d31180f42ced44719fd9e72685c798bf | 2002-01-01T00:05:00 | true | A solution of 3.1 g (99 mmol) of 4-formylbenzonitrile (commercially available) and 40 g (120 mmol) of (triphenylphosphoranylidene)crotonaldehyde [prepared as described in Tetrahedron Lett., 493 (1971)] in 200 ml of dichloromethane was stirred at ambient temperature overnight. At the end of this time, the reaction mixture was concentrated to dryness in vacuo. The resulting residue was purified by chromatography on a silica gel (250 g) column using ethyl acetate as the eluant to give a mixture of the desired compound and a Geometrical isomer thereof. A solution of the mixture of the two isomers in 150 ml of toluene was heated at reflux under irradiation with a tungsten lamp (300 W) for 12 hours. The reaction mixture was then concentrated in vacuo. The resulting residue was purified by chromatography on a silica gel (1.2 kg) column using a 1:9 mixture of ethyl acetate and toluene as the eluant to afford 3.46 g (yield 19%) of the title compound as pale brown needle-like crystals which were collected by filtration. | N#Cc1ccc(/C=C/C=C/C=O)cc1 | null | O=C/C=C/C=P(c1ccccc1)(c1ccccc1)c1ccccc1 | N#Cc1ccc(C=O)cc1 | null | [CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1)=O.C1(P(=[CH:30]/[CH:31]=[CH:32]/[CH:33]=[O:34])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[O:34]=[CH:33]/[CH:32]=[CH:31]/[CH:30]=[CH:1]/[C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1 | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,743,677 | [H-] | [Na+] | null | null | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | 2016-01-01T00:07:00 | true | To a stirred solution of 2-methyl-N-(7H-purin-6-yl)propanamide (1.5 g, 24.36 mmol) in dimethylformamide (20 mL), sodium hydride (0.88 g, 36.55 mmol) was added portion wise in 10 minutes at 0° C. The above suspension was stirred for 10 minutes at 0° C. followed by addition of 2-(trimethylsilyl)ethoxymethyl chloride (4.87 g, 29.24 mmol) slowly at 0° C. under nitrogen atmosphere. The reaction was stirred at room temperature for 16 h. After completion of the reaction, the mixture was quenched with saturated aqueous solution of ammonium chloride and product was extracted with dichloromethane (2×50 mL). The organics were then separated, dried (magnesium sulfate) and concentrated to dryness under vacuum and the crude was purified by flash chromatography eluting with 2% methanol in dichloromethane. Concentration of the desired fractions afford 2-methyl-N-[7-(2-trimethylsilylethoxymethyl)purin-6-yl]propanamide (2) as white solid. Yield: 2 g, 24%. | CC(C)C(=O)Nc1ncnc2ncn(COCC[Si](C)(C)C)c12 | null | C[Si](C)(C)CCOCCl | CC(C)C(=O)Nc1ncnc2nc[nH]c12 | null | [CH3:1][CH:2]([CH3:15])[C:3]([NH:5][C:6]1[N:14]=[CH:13][N:12]=[C:11]2[C:7]=1[NH:8][CH:9]=[N:10]2)=[O:4].[H-].[Na+].[CH3:18][Si:19]([CH3:26])([CH3:25])[CH2:20][CH2:21][O:22][CH2:23]Cl>CN(C)C=O>[CH3:18][Si:19]([CH3:26])([CH3:25])[CH2:20][CH2:21][O:22][CH2:23][N:8]1[C:7]2[C:11](=[N:12][CH:13]=[N:14][C:6]=2[NH:5][C:3](=[O:4])[CH:2]([CH3:15])[CH3:1])[N:10]=[CH:9]1 | 0.17 | CN(C)C=O | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
221,547 | null | null | null | null | ord_dataset-42629b4cf1094978a5e5f29f22639ee7 | 1991-01-01T00:01:00 | true | A mixture of 2.9 g of 3-(2-chlorophenyl)-1,2,4-thiadiazole-5-sulfonamide in 11 ml of trimethyl orthoisobutyrate was warmed to about 85° with an oil bath. After 2.5 hours the solution was cooled to room temperature, whereupon a precipitate formed. Hexane (25 ml) was added to insure complete precipitation. The solid was filtered, washed with hexane and vacuum dried (P2O5) to give 3.08 g of solid, m.p. 75°-76°. | COC(=NS(=O)(=O)c1nc(-c2ccccc2Cl)ns1)C(C)C | null | NS(=O)(=O)c1nc(-c2ccccc2Cl)ns1 | COC(OC)(OC)C(C)C | null | [Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]=[C:11]([S:13]([NH2:16])(=[O:15])=[O:14])[S:10][N:9]=1.CCCCCC.[C:23](OC)(OC)([O:27][CH3:28])[CH:24]([CH3:26])[CH3:25]>>[CH3:28][O:27][C:23](=[N:16][S:13]([C:11]1[S:10][N:9]=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[N:12]=1)(=[O:14])=[O:15])[CH:24]([CH3:26])[CH3:25] | null | CCCCCC | null | null | 25 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
860,932 | F[N+]12CC[N+](CCl)(CC1)CC2 | null | null | null | ord_dataset-93908aaae836460ebd48d733eccad483 | 2009-01-01T00:01:00 | true | The product of Example 3 (0.1 g) was dissolved in methanol (10 ml), Selectfluor™ (0.12 g) added and stirred for 20 h. The mixture was evaporated and purified by silica gel chromatography (5% methanol/DCM) to yield the title product as a white solid. Yield 19 mg. | C[C@H](CO)Nc1nc(SCc2cccc(Cl)c2)nc(O)c1F | null | F[B-](F)(F)F | C[C@H](CO)Nc1cc(O)nc(SCc2cccc(Cl)c2)n1 | null | [Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][S:6][C:7]1[N:12]=[C:11]([OH:13])[CH:10]=[C:9]([NH:14][C@H:15]([CH3:18])[CH2:16][OH:17])[N:8]=1.[B-](F)(F)(F)[F:23].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][S:6][C:7]1[N:12]=[C:11]([OH:13])[C:10]([F:23])=[C:9]([NH:14][C@H:15]([CH3:18])[CH2:16][OH:17])[N:8]=1 | 20 | CO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,200,237 | [Na+] | [OH-] | null | null | ord_dataset-fb72428f30234761b4216139dc228d0c | 2012-01-01T00:09:00 | true | A solution of N-[4-(2-Methyl-2,3,4,9-tetrahydro-1H-β-carbolin-6-ylsulfamoyl)-phenyl]-acetamide (example 7) (80 mg, 0.2 mmol) in 1 mL of an aqueous 10% de NaOH solution was refluxed for 2 h. The resulting mixture was treated with H2O (25 mL) and EtOAc (25 mL) and neutralized by addition of AcOH glacial. The aqueous phase was washed again with EtOAc and the combined organic extracts dried to afford 50 mg of 4-amino-N-(2-methyl-2,3,4,9-tetrahydro-1H-β-carbolin-6-yl)-benzenesulfonamide as a cream colored amorphous solid, mp 236-237° C. 1H-NMR (300 MHz, DMSO-d6): (ppm) 2.36 (s, 3H); 2.55 (bb, 2H); 2.61 (bb, 2H); 3.45 (bb, 2H); 5.83 (bb, 2H); 6.44 (sys AB, 2H, J=8.7 Hz); 6.68 (dd, 1H, J=8.4, 1.8 Hz); 6.99 (bb, 1H); 7.05 (d, 1H, J=8.4 Hz); 7.25 (sys AB, 2H, J=8.7 Hz); 9.27 (s, 1H); 10.63 (s, 1H). | CN1CCc2c([nH]c3ccc(NS(=O)(=O)c4ccc(N)cc4)cc23)C1 | null | CC(=O)Nc1ccc(S(=O)(=O)Nc2ccc3[nH]c4c(c3c2)CCN(C)C4)cc1 | null | null | [CH3:1][N:2]1[CH2:14][CH2:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([NH:15][S:16]([C:19]4[CH:24]=[CH:23][C:22]([NH:25]C(=O)C)=[CH:21][CH:20]=4)(=[O:18])=[O:17])[CH:10]=3)[NH:5][C:4]=2[CH2:3]1.[OH-].[Na+].O.CCOC(C)=O>CC(O)=O>[NH2:25][C:22]1[CH:23]=[CH:24][C:19]([S:16]([NH:15][C:9]2[CH:10]=[C:11]3[C:6](=[CH:7][CH:8]=2)[NH:5][C:4]2[CH2:3][N:2]([CH3:1])[CH2:14][CH2:13][C:12]3=2)(=[O:18])=[O:17])=[CH:20][CH:21]=1 | null | O | CCOC(C)=O | CC(=O)O | null | 70.1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,724,592 | null | null | null | null | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | 2016-01-01T00:05:00 | true | (S)-4-benzyl-3-methyl-5-oxomorpholine-3-carboxylic acid (2.49 g, 10 mmol) was reacted with benzyl bromide (2.05 g, 12 mmol) according to the procedure as described in Example 34, Step A to give the title compound as colorless oil (2.38 g, 70%). The compound was characterized by the following spectroscopic data: | C[C@@]1(C(=O)OCc2ccccc2)COCC(=O)N1Cc1ccccc1 | null | C[C@@]1(C(=O)O)COCC(=O)N1Cc1ccccc1 | BrCc1ccccc1 | null | [CH2:1]([N:8]1[C:13](=[O:14])[CH2:12][O:11][CH2:10][C@@:9]1([CH3:18])[C:15]([OH:17])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[CH2:1]([N:8]1[C:13](=[O:14])[CH2:12][O:11][CH2:10][C@@:9]1([CH3:18])[C:15]([O:17][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1 | null | null | null | null | null | null | 70.1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
821,767 | null | null | null | null | ord_dataset-ec58fad8331a42c5a67ad75aac6713b4 | 2008-01-01T00:05:00 | true | The title compound, MS: m/e=480.2 (M+H+), was prepared in analogy to example 16 from 7-amino-5-methyl-5H,7H-dibenzo[b,d]azepin-6-one and N-(3,5-difluoro-benzyl)-2-methoxy-malonamic acid. | COC(C(=O)NCc1cc(F)cc(F)c1)C(=O)NC1C(=O)N(C)c2ccccc2-c2ccccc21 | null | CN1C(=O)C(N)c2ccccc2-c2ccccc21 | COC(C(=O)O)C(=O)NCc1cc(F)cc(F)c1 | null | [NH2:1][CH:2]1[C:8](=[O:9])[N:7]([CH3:10])[C:6]2[CH:11]=[CH:12][CH:13]=[CH:14][C:5]=2[C:4]2[CH:15]=[CH:16][CH:17]=[CH:18][C:3]1=2.[F:19][C:20]1[CH:21]=[C:22]([CH:33]=[C:34]([F:36])[CH:35]=1)[CH2:23][NH:24][C:25](=[O:32])[CH:26]([O:30][CH3:31])[C:27](O)=[O:28]>>[F:19][C:20]1[CH:21]=[C:22]([CH:33]=[C:34]([F:36])[CH:35]=1)[CH2:23][NH:24][C:25](=[O:32])[CH:26]([O:30][CH3:31])[C:27]([NH:1][CH:2]1[C:8](=[O:9])[N:7]([CH3:10])[C:6]2[CH:11]=[CH:12][CH:13]=[CH:14][C:5]=2[C:4]2[CH:15]=[CH:16][CH:17]=[CH:18][C:3]1=2)=[O:28] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,529,529 | null | null | null | null | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | 2014-01-01T00:12:00 | true | A mixture of ethyl 2-[(2′-cyanobiphenyl-4-yl)methyl]-3-oxohexanoate (4 g) and N-[4-(prop-2-en-1-yloxy)cyclohexyl]-4H-1,2,4-triazol-3-amine (1.3 g) was stirred at 250° C. for 20 min under microwave irradiation. The obtained reaction mixture was purified by silica gel column chromatography to give the title compound as a colorless solid (0.7 g, 24%). | C=CCOC1CCC(n2c(=O)c(Cc3ccc(-c4ccccc4C#N)cc3)c(CCC)n3ncnc23)CC1 | null | C=CCOC1CCC(Nc2nnc[nH]2)CC1 | CCCC(=O)C(Cc1ccc(-c2ccccc2C#N)cc1)C(=O)OCC | null | [C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([C:22](=O)[CH2:23][CH2:24][CH3:25])[C:17](OCC)=[O:18])=[CH:11][CH:10]=1)#[N:2].[CH2:27]([O:30][CH:31]1[CH2:36][CH2:35][CH:34]([NH:37][C:38]2[NH:42][CH:41]=[N:40][N:39]=2)[CH2:33][CH2:32]1)[CH:28]=[CH2:29]>>[O:18]=[C:17]1[C:16]([CH2:15][C:12]2[CH:13]=[CH:14][C:9]([C:4]3[C:3]([C:1]#[N:2])=[CH:8][CH:7]=[CH:6][CH:5]=3)=[CH:10][CH:11]=2)=[C:22]([CH2:23][CH2:24][CH3:25])[N:39]2[N:40]=[CH:41][N:42]=[C:38]2[N:37]1[CH:34]1[CH2:33][CH2:32][CH:31]([O:30][CH2:27][CH:28]=[CH2:29])[CH2:36][CH2:35]1 | 0.33 | null | null | null | 250 | null | 23.6 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
174,588 | null | null | null | null | ord_dataset-4937da99a6a247eb90fa70f0d2eac3db | 1988-01-01T00:07:00 | true | A mixture of 5.3 g (0.03 mole) of 1-(chloromethyl)naphthalene and 8.6556 g (0.033 mole) of triphenylphosphine in 150 mL of dimethylformamide was heated at reflux with stirring for 5 hours. A copious white precipitate formed. The precipitate was filtered and washed with 100 mL of dimethylformamide and 100 mL of ether. The product was dried in vacuo to yield 11.97 g (91%) of 1-naphthylmethyltriphenylphosphonium chloride as white crystals: mp 285°-288°; IR (KBr) 3050, 3010, 2880, 2790, 1665, 1590, 1510, 1485, 1440, 1385, 1335, 1275, 1155, 1110, 1095, 875, 810, 785, 730, and 690 cm-1 ; NMR (DMSO) δ5.67 (d, J=15 Hz, 2H), 7.60 (m, 15H) and 7.73 (m, 7H). | [Cl-] | c1ccc([P+](Cc2cccc3ccccc23)(c2ccccc2)c2ccccc2)cc1 | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | ClCc1cccc2ccccc12 | null | [Cl:1][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.[C:13]1([P:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C)C=O>[Cl-:1].[C:3]1([CH2:2][P+:19]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1 | 5 | CN(C)C=O | null | null | null | 90.9 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,466,879 | O=S(=O)(O)O | [K+] | null | null | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | 2014-01-01T00:08:00 | true | 1-(2-tert-butylphenyl)pyrrolidine (350 mg, 1.72 mmol) was added portionwise to conc. H2SO4 (1 mL) to generate a yellow homogeneous solution. The solution was then cooled to 0° C. and KNO3 (191 mg, 1.9 mmol) was added portionwise maintaining the internal temperature below 5° C. The reaction was stirred for 2 h and then poured on ice-water and extracted with DCM, dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel column chromatography to obtain 1-(2-tert-butyl-5-nitrophenyl)pyrrolidine (325 mg, 76%). LC/MS: m/z 248.9 (M+H)+ at 2.39 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)). | CC(C)(C)c1ccc([N+](=O)[O-])cc1N1CCCC1 | null | CC(C)(C)c1ccccc1N1CCCC1 | O=[N+]([O-])[O-] | null | [C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].OS(O)(=O)=O.[N+:21]([O-])([O-:23])=[O:22].[K+]>>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N+:21]([O-:23])=[O:22])=[CH:7][C:6]=1[N:11]1[CH2:12][CH2:13][CH2:14][CH2:15]1)([CH3:4])([CH3:2])[CH3:3] | 2 | null | null | null | 0 | 76.1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,391,068 | null | null | null | null | ord_dataset-31641fb65b34430fa7435229b949b604 | 2014-01-01T00:01:00 | true | The title compound was prepared in the same manner as described for intermediate 61 using ethyl 4-[4-(methylthio)phenyl]-2,4-dioxobutanoate (851 mg, 3.20 mmol), benzene (6 mL), 1-(1-methylethyl)-1H-pyrazol-5-amine (400 mg, 3.20 mmol), and acetic acid (3 mL). The crude product was purified by column chromatography (Silica gel, eluent; 0 to 100% EtOAc/hexanes) to give 870 mg (63%) of product. LCMS E-S (M+H)=433.2. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.47-1.57 (m, 3H), 1.66 (d, J=6.8 Hz, 6H), 2.58 (s, 3H), 4.56 (q, J=7.2 Hz, 2H), 5.38-5.55 (m, 1H), 7.36-7.46 (m, 2H), 8.12-8.19 (m, 2H), 8.22 (s, 1H), 8.40 (s, 1H). | CCOC(=O)c1cc(-c2ccc(SC)cc2)nc2c1cnn2C(C)C | null | CCOC(=O)C(=O)CC(=O)c1ccc(SC)cc1 | CC(C)n1nccc1N | null | [CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH2:10][C:11](=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:5][CH:4]=1.C1C=CC=CC=1.[CH3:25][CH:26]([N:28]1[C:32]([NH2:33])=[CH:31][CH:30]=[N:29]1)[CH3:27]>C(O)(=O)C>[CH3:25][CH:26]([N:28]1[C:32]2[N:33]=[C:9]([C:6]3[CH:7]=[CH:8][C:3]([S:2][CH3:1])=[CH:4][CH:5]=3)[CH:10]=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:31]=2[CH:30]=[N:29]1)[CH3:27] | null | c1ccccc1 | CC(=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 |
1,241,583 | Cl | null | null | null | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | 2013-01-01T00:01:00 | true | 3-Chloro-6-(1-isopropylpiperidin-4-yl)pyridazine, hydrochloride (0.5 g, 1.6 mmol) and 2-methylpyridin boronic acid (0.241 g, 1.76 mmol) were mixed with catalyst and reacted in the same manner as in example 18. The title compound was isolated as white crystals of the trihydrochloride. Yield: 164 mg (25%). | Cc1cc(-c2ccc(C3CCN(C(C)C)CC3)nn2)ccn1 | null | CC(C)N1CCC(c2ccc(Cl)nn2)CC1 | CC1(B(O)O)C=CC=CN1 | null | [ClH:1].[Cl:2][C:3]1[N:4]=[N:5][C:6]([CH:9]2[CH2:14][CH2:13][N:12]([CH:15]([CH3:17])[CH3:16])[CH2:11][CH2:10]2)=[CH:7][CH:8]=1.[CH3:18][C:19]1(B(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][NH:20]1>>[ClH:2].[ClH:1].[ClH:2].[CH:15]([N:12]1[CH2:13][CH2:14][CH:9]([C:6]2[N:5]=[N:4][C:3]([C:23]3[CH:22]=[CH:21][N:20]=[C:19]([CH3:18])[CH:24]=3)=[CH:8][CH:7]=2)[CH2:10][CH2:11]1)([CH3:17])[CH3:16] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,648,109 | null | null | null | null | ord_dataset-bcc0b01d4f58457a8733b10a099f43ba | 2015-01-01T00:10:00 | true | The title compound was synthesized from 1-methyl-7-hydroxy-β-carboline (1.504 g, 4.770 mmol) in presence of 1-bromo-3-methylbutane (1.440 g, 9.520 mmol) as described here above. | Cc1nccc2c3ccc(OCCC(C)C)cc3n(CCC(C)C)c12 | null | CC(C)CCBr | Cc1nccc2c1[nH]c1cc(O)ccc12 | null | [CH3:1][C:2]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[C:10]([OH:15])[CH:11]=3)[C:6]=2[CH:5]=[CH:4][N:3]=1.Br[CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20]>>[CH3:1][C:2]1[C:14]2[N:13]([CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])[C:12]3[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH2:4][CH2:5][CH:6]([CH3:7])[CH3:14])[CH:11]=3)[C:6]=2[CH:5]=[CH:4][N:3]=1 | null | null | null | null | null | null | 69 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,220,508 | [Pd] | null | null | null | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | 2012-01-01T00:10:00 | true | To a solution of spiro[5.5]undec-1-en-3-one (8.9 g) obtained in Step 1 in tetrahydrofuran (360 mL) was added 5% palladium carbon (0.89 g), followed by stirring the reaction mixture at room temperature in an atmosphere of hydrogen under normal pressure for 2 hours. Then, the reaction mixture was filtered through Celite and the filtrate was concentrated to obtain spiro[5.5]undecan-3-one (9.3 g). | O=C1CCC2(CCCCC2)CC1 | null | O=C1C=CC2(CCCCC2)CC1 | [H][H] | null | [CH:1]1[C:6]2([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]2)[CH2:5][CH2:4][C:3](=[O:12])[CH:2]=1.[H][H]>O1CCCC1.[C].[Pd]>[CH2:5]1[C:6]2([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]2)[CH2:1][CH2:2][C:3](=[O:12])[CH2:4]1 | null | C1CCOC1 | null | null | null | null | 103.2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,730,923 | [Pd] | null | null | null | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | 2016-01-01T00:05:00 | true | 10% Pd/C (1.19 g) was added to a solution of compound 30 (3.97 g, 5.91 mmol) in ethanol (100 mL). The resulting mixture was stirred under H2 (g) atmosphere at room temperature for 12 hours. The reaction mixture was filtered through a celite pad and washed with ethanol (2×20 mL). The combined filtrate was evaporated in vacuo to give an oily residue which was triturated with Et2O to provide an off-white solid 28 (2.67 g, 98% yield). | Nc1ccc(CC2CN3CCCN(CC(=O)O)CCN(CCCN(CC(=O)O)CC3)C2)cc1 | null | O=C(CN1CCCN2CCN(CC(=O)OCc3ccccc3)CCCN(CC1)CC(Cc1ccc([N+](=O)[O-])cc1)C2)OCc1ccccc1 | null | null | C([O:8][C:9]([CH2:11][N:12]1[CH2:25][CH2:24][CH2:23][N:22]2[CH2:26][CH:27]([CH2:29][C:30]3[CH:35]=[CH:34][C:33]([N+:36]([O-])=O)=[CH:32][CH:31]=3)[CH2:28][N:15]([CH2:16][CH2:17][CH2:18][N:19]([CH2:39][C:40]([O:42]CC3C=CC=CC=3)=[O:41])[CH2:20][CH2:21]2)[CH2:14][CH2:13]1)=[O:10])C1C=CC=CC=1>C(O)C.[Pd]>[C:9]([CH2:11][N:12]1[CH2:25][CH2:24][CH2:23][N:22]2[CH2:26][CH:27]([CH2:29][C:30]3[CH:31]=[CH:32][C:33]([NH2:36])=[CH:34][CH:35]=3)[CH2:28][N:15]([CH2:16][CH2:17][CH2:18][N:19]([CH2:39][C:40]([OH:42])=[O:41])[CH2:20][CH2:21]2)[CH2:14][CH2:13]1)([OH:10])=[O:8] | 12 | CCO | null | null | 25 | 97.9 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
117,411 | null | null | null | null | ord_dataset-3708161f4ba04e959b9a7a8d59fd86e1 | 1984-01-01T00:05:00 | true | Finely ground N-isopropyl valine (31 mmol) in 150 ml dioxane is heated to 38°-40° and excess carbonyl chloride is slowly passed in over 4-5 hours. Dry air is then passed through the reaction for 18 hours, after which the dioxane is removed at 40° (20 mm) to yield 3,4-diisopropyl-oxazolidine-2,5-dione. | CC(C)C1C(=O)OC(=O)N1C(C)C | null | O=C(Cl)Cl | CC(C)N[C@H](C(=O)O)C(C)C | null | [CH:1]([NH:4][C@H:5]([C:9]([OH:11])=[O:10])[CH:6]([CH3:8])[CH3:7])([CH3:3])[CH3:2].[C:12](Cl)(Cl)=[O:13]>O1CCOCC1>[CH:1]([N:4]1[CH:5]([CH:6]([CH3:7])[CH3:8])[C:9](=[O:11])[O:10][C:12]1=[O:13])([CH3:2])[CH3:3] | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
722,307 | Cl | null | null | null | ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | 2006-01-01T00:08:00 | true | A mixture of methyl (2E)-3-[4-(9a-butyl-7-methoxy-3-oxo-2,3,9,9a-tetrahydro-1H-fluoren-4-yl)phenyl]-2-propenoate (60 mg, 92% weight pure, 0.128 mmol) and pyridine hydrochloride (741 mg, 6.41 mmol) was placed under a nitrogen atmosphere, heated in an oil bath at 190° C., and stirred. The reaction flask was periodically dipped deeper into the heating bath in order to melt the pyridine hydrochloride that condensed on the sides of the flask. After 2 hours at 190° C., the reaction mixture was cooled to room temperature and partitioned between EtOAc (10 mL) and water (10 mL). The aqueous phase was extracted with more EtOAc (2×5 mL). The combined EtOAc extracts were washed with brine, dried over MgSO4, filtered, and evaporated under vacuum to a yellow solid (55 mg). The crude product was suspended in EtOAc (10 mL) and extracted with 5% NaHCO3 (5 mL). The NaHCO3 solution was acidified with 2N HCl (2.5 mL) and extracted with EtOAc (2×5 mL). The latter EtOAc extracts were combined, washed with brine, dried over MgSO4, filtered, and evaporated under vacuum to a yellow solid (39.4 mg). This material was triturated with diethyl ether and dried under vacuum to afford (2E)-3-[4-(9a-butyl-7-hydroxy-3-oxo-2,3,9,9a-tetrahydro-1H-fluoren-4-yl)phenyl]-2-propenoic acid as a pale yellow solid. | CCCCC12CCC(=O)C(c3ccc(/C=C/C(=O)O)cc3)=C1c1ccc(O)cc1C2 | null | CCCCC12CCC(=O)C(c3ccc(/C=C/C(=O)OC)cc3)=C1c1ccc(OC)cc1C2 | null | null | [CH2:1]([C:5]12[CH2:17][CH2:16][C:15](=[O:18])[C:14]([C:19]3[CH:24]=[CH:23][C:22](/[CH:25]=[CH:26]/[C:27]([O:29]C)=[O:28])=[CH:21][CH:20]=3)=[C:13]1[C:12]1[C:7](=[CH:8][C:9]([O:31]C)=[CH:10][CH:11]=1)[CH2:6]2)[CH2:2][CH2:3][CH3:4].Cl.N1C=CC=CC=1>>[CH2:1]([C:5]12[CH2:17][CH2:16][C:15](=[O:18])[C:14]([C:19]3[CH:20]=[CH:21][C:22](/[CH:25]=[CH:26]/[C:27]([OH:29])=[O:28])=[CH:23][CH:24]=3)=[C:13]1[C:12]1[C:7](=[CH:8][C:9]([OH:31])=[CH:10][CH:11]=1)[CH2:6]2)[CH2:2][CH2:3][CH3:4] | 2 | c1ccncc1 | null | null | 190 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,424,591 | [Cl-] | [Na+] | null | null | ord_dataset-5e6956e6e8c24a168866a253f4a66c6c | 2014-01-01T00:05:00 | true | A mixture of dimethyl 2-(2-chloro-5-methoxy-4-nitrophenyl)malonate (3.0 g, 9.44 mmol) and sodium chloride (0.99 g, 16.99 mmol) in DMSO (50 mL) and water (0.17 mL, 9.44 mmol) was heated for 5 hours at 120° C. The reaction mass was allowed to cool to room temperature and water (400 mL) and EtOAc (50 mL) were added and stirring continued for 15 minutes. The separated aqueous layer was extracted with EtOAc (50 mL), and then the combined organic layers were washed with brine (50 mL), dried (Na2SO4) and concentrated under reduced pressure. The crude residue was purified by column chromatography on neutral silica gel using 15-25% EtOAc in hexane to give the desired material (1.5 g, 61%) as a solid. | COC(=O)Cc1cc(OC)c([N+](=O)[O-])cc1Cl | null | COC(=O)C(C(=O)OC)c1cc(OC)c([N+](=O)[O-])cc1Cl | null | null | [Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[CH:13](C(OC)=O)[C:14]([O:16][CH3:17])=[O:15].[Cl-].[Na+].O.CCOC(C)=O>CS(C)=O>[CH3:17][O:16][C:14](=[O:15])[CH2:13][C:3]1[CH:4]=[C:5]([O:11][CH3:12])[C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[Cl:1] | 0.25 | CS(C)=O | CCOC(C)=O | O | 120 | 61.2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
198,787 | C[O-] | [Na+] | null | null | ord_dataset-f6fafbb8ce5f4ef099be3a772075ec97 | 1989-01-01T00:10:00 | true | 34.7 g (0.469 mole) of ethyl formate are added dropwise with stirring to 129.4 g (0.469 mole) of 3,3-dimethyl-4-(4-trifluoromethylthiophenyl)-butan-2-one and 25.3 g (0.469 mole) of sodium methylate in 1 liter of diethyl ether at room temperature, and the mixture is stirred at room temperature for 4 hours after the addition is complete. For work-up, the mixture is extracted with 1 liter of water, and the combined aqueous extracts are washed once with diethyl ether, acidified to pH 1-2 with dilute aqueous hydrochloric acid and extracted with dichloromethane. The dichloromethane phase is dried over sodium sulphate and concentrated in vacuo. 90.5 g of 4,4-dimethyl-5-(4-trifluoromethylthiophenyl)-penten-1-ol-3-one are obtained; these are dissolved in 200 ml of methanol and 17.0 g (0.315 mol) of sodium methylate are added. Concentrating the solution in vacuo gives 97.1 g (75% of theory) of the sodium salt of 4,4-dimethyl-5-(4-trifluoromethylthiophenyl)-1 -penten-1-ol-3-one as a resin, which is further reacted without purification. ##STR875## | CC(C)(Cc1ccc(SC(F)(F)F)cc1)C(=O)C=CO | null | CC(=O)C(C)(C)Cc1ccc(SC(F)(F)F)cc1 | CCOC=O | null | [CH:1](OCC)=[O:2].[CH3:6][C:7]([CH3:23])([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([S:18][C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=1)[C:8](=[O:10])[CH3:9].C[O-].[Na+]>C(OCC)C>[CH3:6][C:7]([CH3:23])([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([S:18][C:19]([F:21])([F:22])[F:20])=[CH:14][CH:13]=1)[C:8](=[O:10])[CH:9]=[CH:1][OH:2] | 4 | CCOCC | null | null | 25 | 63.4 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,641,976 | Cl | null | null | null | ord_dataset-bcc0b01d4f58457a8733b10a099f43ba | 2015-01-01T00:10:00 | true | To a solution of (1R,2S,3R,5R)-3-amino-5-(hydroxymethyl)cyclopentane-1,2-diol HCl (1.00 g, 5.44 mmol) and 2-amino-4,6-dichloropyrimidine (0.982 g, 5.99 mmol) in isopropyl alcohol (8 mL) was added Et3N (1.90 mL, 13.6 mmol). The reaction was heated to 90° C. for 1 h in an oil bath then cooled, filtered and concentrated in vacuo. The residue was dissolved in CH2Cl2 and purified by flash chromatography (20 to 50% MeOH/CH2Cl2) to afford the title compound as an off-white solid (2.025 g, >99%). LC/MS: Rt=0.81 min ES 260 (FA standard). | OC[C@H]1C[C@@H](Nc2cc(Cl)ncn2)[C@H](O)[C@@H]1O | null | Nc1nc(Cl)cc(Cl)n1 | N[C@@H]1C[C@H](CO)[C@@H](O)[C@H]1O | null | Cl.[NH2:2][C@@H:3]1[CH2:7][C@H:6]([CH2:8][OH:9])[C@@H:5]([OH:10])[C@H:4]1[OH:11].N[C:13]1[N:18]=[C:17](Cl)[CH:16]=[C:15]([Cl:20])[N:14]=1.CCN(CC)CC>C(O)(C)C>[Cl:20][C:15]1[N:14]=[CH:13][N:18]=[C:17]([NH:2][C@@H:3]2[CH2:7][C@H:6]([CH2:8][OH:9])[C@@H:5]([OH:10])[C@H:4]2[OH:11])[CH:16]=1 | null | CC(C)O | CCN(CC)CC | null | 90 | 143.3 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,406,579 | [H-] | [Na+] | null | null | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | 2014-01-01T00:03:00 | true | Preparation according to Preparation 14. 3-(3-Chloro-2-fluorophenyl)-3-methoxypyrrolidine (3.44 g, 15 mmol), dry dimethyl formamide (5 mL), sodium hydride (60% dispersion in mineral oil, 0.720 g, 18 mmol). Benzylbromide (1.78 mL, 15 mmol) in dry dimethyl formamide (5 mL). Work up according to Preparation 14. Purification by flash column chromatography on silica gel (ethyl acetate) gave the title compound (3.83 g, 80%). MS m/z (rel. intensity, 70 eV) 304 (14), 289 (16), 133 (65), 132 (35), 91 (bp). | COC1(c2cccc(Cl)c2F)CCN(Cc2ccccc2)C1 | null | BrCc1ccccc1 | COC1(c2cccc(Cl)c2F)CCNC1 | null | [Cl:1][C:2]1[C:3]([F:15])=[C:4]([C:8]2([O:13][CH3:14])[CH2:12][CH2:11][NH:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C=O>[CH2:18]([N:10]1[CH2:11][CH2:12][C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=2[F:15])([O:13][CH3:14])[CH2:9]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1 | null | CN(C)C=O | null | null | null | null | 79.8 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,090,050 | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | ord_dataset-52a37d876ddb453e86de0c15fa233d29 | 2011-01-01T00:09:00 | true | To 3-(3-(1,2,4-oxadiazol-3-yl)phenethoxy)-N-cyclohexyl-N-(2,2-dimethoxyethyl)propanamide [Example 11, Step ii)] (500 mg) in NMP (4 mL) was added p-toluenesulfonic acid (441 mg) and the mixture stirred for 8 h. After work-up the material was used in the next step directly. | O=CCN(C(=O)CCOCCc1cccc(-c2ncon2)c1)C1CCCCC1 | null | COC(CN(C(=O)CCOCCc1cccc(-c2ncon2)c1)C1CCCCC1)OC | null | null | [O:1]1[CH:5]=[N:4][C:3]([C:6]2[CH:7]=[C:8]([CH:29]=[CH:30][CH:31]=2)[CH2:9][CH2:10][O:11][CH2:12][CH2:13][C:14]([N:16]([CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[CH2:17][CH:18](OC)[O:19]C)=[O:15])=[N:2]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CN1C(=O)CCC1>[O:1]1[CH:5]=[N:4][C:3]([C:6]2[CH:7]=[C:8]([CH:29]=[CH:30][CH:31]=2)[CH2:9][CH2:10][O:11][CH2:12][CH2:13][C:14]([N:16]([CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[CH2:17][CH:18]=[O:19])=[O:15])=[N:2]1 | 8 | CN1CCCC1=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 |
1,658,249 | [Pd+2] | [OH-] | null | null | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | 2015-01-01T00:11:00 | true | A mixture of 6-benzyl-2-(4-((2,4-difluorophenyl)fluoromethyl)piperidin-1-yl)-N-isopropyl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-3-amine TFA salt (60 mg, 0.096 mmol) and Pd(OH)2 on carbon, (20 wt %, 6 mg, 8.54 μmol) in THF (960 μL) was stirred under an atmosphere of hydrogen gas (balloon) at rt. After 2 h, the mixture was purified by HPLC Method A to give the title compound as a TFA salt (47.6 mg, 93%) as a yellow foam. 1H NMR (400 MHz, methanol-d4) δ ppm 1.23 (dd, J=6.4, 2.4 Hz, 6H), 1.41-1.49 (m, 1H), 1.52-1.74 (m, 2H), 1.98-2.14 (m, 2H), 2.68 (qd, J=12.6, 2.5 Hz, 2H), 2.96 (t, J=6.3 Hz, 2H), 3.40-3.51 (m, 2H), 3.52 (t, J=6.3 Hz, 2H), 4.10-4.16 (m, 1H), 4.16 (s, 2H), 5.53 (dd, J=46.5, 7.6 Hz, 1H), 6.97-7.08 (m, 2H), 7.47-7.55 (m, 1H); ESI-MS m/z [M+H]+ 420.3. | CC(C)Nc1nc2c(nc1N1CCC(C(F)c3ccc(F)cc3F)CC1)CCNC2 | null | CC(C)Nc1nc2c(nc1N1CCC(C(F)c3ccc(F)cc3F)CC1)CCN(Cc1ccccc1)C2 | null | null | [OH:1][C:2]([C:4]([F:7])([F:6])[F:5])=[O:3].C([N:15]1[CH2:24][CH2:23][C:22]2[C:17](=[N:18][C:19]([NH:41][CH:42]([CH3:44])[CH3:43])=[C:20]([N:25]3[CH2:30][CH2:29][CH:28]([CH:31]([C:33]4[CH:38]=[CH:37][C:36]([F:39])=[CH:35][C:34]=4[F:40])[F:32])[CH2:27][CH2:26]3)[N:21]=2)[CH2:16]1)C1C=CC=CC=1>C1COCC1.[OH-].[OH-].[Pd+2]>[F:40][C:34]1[CH:35]=[C:36]([F:39])[CH:37]=[CH:38][C:33]=1[CH:31]([F:32])[CH:28]1[CH2:29][CH2:30][N:25]([C:20]2[N:21]=[C:22]3[CH2:23][CH2:24][NH:15][CH2:16][C:17]3=[N:18][C:19]=2[NH:41][CH:42]([CH3:44])[CH3:43])[CH2:26][CH2:27]1.[C:2]([OH:3])([C:4]([F:7])([F:6])[F:5])=[O:1] | 2 | O=C(O)C(F)(F)F | C1CCOC1 | null | 25 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
149,493 | null | null | null | null | ord_dataset-f222e615b1f74f0fabef9cd9b98516b7 | 1986-01-01T00:10:00 | true | 3-Hydroxytetrahydrofuran (0.04 mole), toluene (50 ml) and triethylamine (0.04 mole) are charged into a glass reaction vessel equipped with a mechanical stirrer and addition funnel. A solution of 2-chloro-5-(2-bromo-4-trifluoromethylphenoxy)benzoyl chloride (0.04 mole) in toluene (20 ml) is slowly added at room temperature with stirring. After the addition is completed, stirring is continued for a period of about eight hours. After this time, the reaction mixture is washed with water and dried over anhydrous magnesium sulfate. The dried solution is then stripped of solvent under reduced pressure leaving a residue. This residue is purified by silica gel chromatography using toluene and ethyl acetate/toluene mixture as the eluant to yield the desired product 3-tetrahydrofuryl 2-chloro-5-(2-bromo-4-trifluoromethylphenoxy)benzoate. | O=C(OC1CCOC1)c1cc(Oc2ccc(C(F)(F)F)cc2Br)ccc1Cl | null | O=C(Cl)c1cc(Oc2ccc(C(F)(F)F)cc2Br)ccc1Cl | OC1CCOC1 | null | [OH:1][CH:2]1[CH2:6][CH2:5][O:4][CH2:3]1.C(N(CC)CC)C.[Cl:14][C:15]1[CH:23]=[CH:22][C:21]([O:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][C:26]=2[Br:35])=[CH:20][C:16]=1[C:17](Cl)=[O:18]>C1(C)C=CC=CC=1>[Cl:14][C:15]1[CH:23]=[CH:22][C:21]([O:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:32])([F:33])[F:34])=[CH:27][C:26]=2[Br:35])=[CH:20][C:16]=1[C:17]([O:1][CH:2]1[CH2:6][CH2:5][O:4][CH2:3]1)=[O:18] | 8 | CCN(CC)CC | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,026,957 | O=C(Cl)C(=O)Cl | null | null | null | ord_dataset-83acb82dc5ba4f7aba439b9875aaac43 | 2011-01-01T00:02:00 | true | To a solution of oxalyl chloride (27 g, 214 mmol) in anhydrous DCM (300 ml) at −78° C. under nitrogen was added anhydrous DMSO (33.4 g, 428 mmol) and the mixture was stirred at −78° C. for 20 min. A solution of 2,2-dimethylhept-4-yn-1-ol (20 g, 142 mmol) in anydrous DCM (50 ml) was added slowly over a period of 25 min. The reaction mixture was stirred at −78° C. for 2 hours and quenched by the addition of TEA (165 ml, 1.14 mol) and diluted with water (700 ml). The organic layer was separated and washed with a 1.5M aqueous solution of HCl (200 ml), water and brine. The organic layer was dried (MgSO4) and the solvent was removed under reduced pressure to afford the titled compound as a pale brown liquid (16.5 g, 87%). TLC: Pet. ether/EtOAc (8/2): Rf=0.75. | CCC#CCC(C)(C)C=O | null | CCC#CCC(C)(C)CO | null | null | C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][C:12]([CH3:20])([CH2:15][C:16]#[C:17][CH2:18][CH3:19])[CH2:13][OH:14]>C(Cl)Cl.O>[CH3:11][C:12]([CH3:20])([CH2:15][C:16]#[C:17][CH2:18][CH3:19])[CH:13]=[O:14] | 0.33 | O | ClCCl | CS(C)=O | -78 | 84.1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,038,496 | [Na+] | [OH-] | null | null | ord_dataset-3af92aec23dc4810b92eb0d8c60023ee | 2011-01-01T00:03:00 | true | The title compound was synthesized from ethyl 6-(biphenyl-4-ylmethyl)-1,4-dihydrocyclopenta[b]pyrrole-2-carboxylate (0.0343 g, 0.1 mmol, 1 equiv) and sodium hydroxide (0.36 mL, 3.6 mmol, 10 M, 35 equiv), according to General Procedure 7. The resulting product was purified by preparative HPLC using the Chromeleon purification system. A 0.1% formic acid/1% acetonitrile mixture in water (aqueous phase) and methanol (no modifier added—organic phase) using a 50 mm Dynamax HPLC C-18 column at 28 mL/min (initial gradient of 70% methanol and increasing to 100% over 7 minutes) afforded the title compound (15.7 mg, 50%) with purity by HPLC of 93.3% (UV). LCMS m/e 316.2 (M−H). 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.08-2.20 (m, 1H) 2.41-2.50 (m, 2H) 2.75 (dd, J=13.62, 8.54 Hz, 1H) 3.06-3.12 (m, 1H) 6.55 (s, 1H) 7.24 (d, J=8.10 Hz, 2H) 7.28-7.33 (m, 1H) 7.41 (t, J=7.61 Hz, 2H) 7.53 (d, J=8.13 Hz, 2H) 7.60 (d, J=7.20 Hz, 2H) 8.50 (s, 1H). | O=C(O)c1cc2c([nH]1)C(Cc1ccc(-c3ccccc3)cc1)CC2 | null | CCOC(=O)c1cc2c([nH]1)C(Cc1ccc(-c3ccccc3)cc1)=CC2 | null | null | [C:1]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[CH:5][C:4]([CH2:7][C:8]2[C:12]3[NH:13][C:14]([C:16]([O:18]CC)=[O:17])=[CH:15][C:11]=3[CH2:10][CH:9]=2)=[CH:3][CH:2]=1.[OH-].[Na+]>>[C:1]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:2]=[CH:3][C:4]([CH2:7][CH:8]2[C:12]3[NH:13][C:14]([C:16]([OH:18])=[O:17])=[CH:15][C:11]=3[CH2:10][CH2:9]2)=[CH:5][CH:6]=1 | null | null | null | null | null | null | 49.5 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,081,001 | O=C([O-])[O-] | [Cs+] | null | null | ord_dataset-afd812677c134591a99f46ce28de2524 | 2011-01-01T00:08:00 | true | To a solution of 4′-{[2-ethyl-1-(4-hydroxyphenyl)-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl]methyl}biphenyl-2-carbonitrile (0.4 g) in N,N-dimethylacetamide (10 mL) were added 1-iodo-2,2-dimethylpropane (0.26 g) and cesium carbonate (0.44 g), and the mixture was stirred at 120° C. for 24 hr. The mixture was allowed to cool to room temperature and the insoluble material was filtered off. The filtrate was diluted with ethyl acetate, washed with 1 M hydrochloric acid, saturated sodium hydrogen carbonate and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography to give the title compound as a pale-yellow solid (0.40 g, 87%). | CCCc1nc(CC)n(-c2ccc(OCC(C)(C)C)cc2)c(=O)c1Cc1ccc(-c2ccccc2C#N)cc1 | null | CC(C)(C)CI | CCCc1nc(CC)n(-c2ccc(O)cc2)c(=O)c1Cc1ccc(-c2ccccc2C#N)cc1 | null | [CH2:1]([C:3]1[N:4]([C:28]2[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=2)[C:5](=[O:27])[C:6]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[C:20]([C:25]#[N:26])=[CH:21][CH:22]=[CH:23][CH:24]=3)=[CH:15][CH:14]=2)=[C:7]([CH2:9][CH2:10][CH3:11])[N:8]=1)[CH3:2].I[CH2:36][C:37]([CH3:40])([CH3:39])[CH3:38].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C(=O)C>[CH3:36][C:37]([CH3:40])([CH3:39])[CH2:38][O:34][C:31]1[CH:32]=[CH:33][C:28]([N:4]2[C:5](=[O:27])[C:6]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]4[C:20]([C:25]#[N:26])=[CH:21][CH:22]=[CH:23][CH:24]=4)=[CH:15][CH:14]=3)=[C:7]([CH2:9][CH2:10][CH3:11])[N:8]=[C:3]2[CH2:1][CH3:2])=[CH:29][CH:30]=1 | 24 | CC(=O)N(C)C | null | null | 120 | 86.5 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,573,686 | [BH4-] | [Na+] | null | null | ord_dataset-9741bb5fd93044078df2a45f45733054 | 2015-01-01T00:04:00 | true | To a solution of the product from Example 1A (1.0 g, 3.05 mmol) in anhydrous THF (30 ml) at 0° C. was added sodium borohydride (0.357 g, 9.44 mmol). The resulting mixture was stirred at 50° C. overnight. The cooled mixture was poured into water, extracted with ethyl acetate, dried over Na2SO4, filtered and concentrated in vacuo. The resulting solid was triturated with dichloromethane to give a tan solid that was collected by filtration and dried to give the title compound (0.82 gm, 81% yield). | O=[N+]([O-])c1ccc(C(O)CCC(O)c2ccc([N+](=O)[O-])cc2)cc1 | null | O=C(CCC(=O)c1ccc([N+](=O)[O-])cc1)c1ccc([N+](=O)[O-])cc1 | null | null | [N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:24])[CH2:11][CH2:12][C:13]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[O:14])=[CH:6][CH:5]=1)([O-:3])=[O:2].[BH4-].[Na+].O>C1COCC1>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:24])[CH2:11][CH2:12][CH:13]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)[OH:14])=[CH:6][CH:5]=1)([O-:3])=[O:2] | 8 | O | C1CCOC1 | null | 50 | null | 80.9 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
949,704 | N | [OH-] | [Zn] | null | ord_dataset-3feb2a95f66e4706a4a50c977ccd9bf8 | 2010-01-01T00:04:00 | true | To a solution of 2-morpholin-4-yl-8-(1-nitro-dibenzofuran-4-yl)-1-benzopyran-4-one (32, 2.5 mmol, 1.11 g) in acetic acid (50 ml) was added zinc dust (25 mmol, 1.64 g), portionwise over ten minutes. The mixture was then stirred at room temperature for 2 hrs, whereupon it was filtered through a Celite™ pad which was washed with methanol (20 ml) and CH2Cl2 (20 ml). Solvents were removed in vacuo to give a slurry which was then diluted with ammonia hydroxide (30 ml) and the resulting solid removed by filtration. The residue was purified by flash chromatography (SiO2) using MeOH; CH2Cl2-1:99 as eluent to give the desired product (75%) in analytically pure form. m/z 413.5 [M+H]+ (Rt=4.27 min). | Nc1ccc(-c2cccc3c(=O)cc(N4CCOCC4)oc23)c2oc3ccccc3c12 | null | O=c1cc(N2CCOCC2)oc2c(-c3ccc([N+](=O)[O-])c4c3oc3ccccc34)cccc12 | null | null | [N:1]1([C:7]2[O:8][C:9]3[C:17]([C:18]4[C:23]5[O:24][C:25]6[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=6[C:22]=5[C:21]([N+:31]([O-])=O)=[CH:20][CH:19]=4)=[CH:16][CH:15]=[CH:14][C:10]=3[C:11](=[O:13])[CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1>C(O)(=O)C.[OH-].N.[Zn]>[NH2:31][C:21]1[C:22]2[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[O:24][C:23]=2[C:18]([C:17]2[C:9]3[O:8][C:7]([N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)=[CH:12][C:11](=[O:13])[C:10]=3[CH:14]=[CH:15][CH:16]=2)=[CH:19][CH:20]=1 | 2 | CC(=O)O | null | null | 25 | 75 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
867,882 | null | null | null | null | ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | 2009-01-01T00:03:00 | true | A mixture of compound 59 (41 mg, 0.15 mmol), triethylamine (83 uL, 0.60 mmol), α-ethyl-benzyl isocyanate (29 mg, 0.18 mmol) in methylene chloride (1.2 mL) was stirred overnight. TLC analysis indicated the completion the reaction. Removal of solvents gave the crude material, which was purified by preparative TLC plate (15% EtOAc in hexanes), yielding 38.2 mg of compound 60 (59%): LC-MS purity: 98.1%; 1HNMR (300 MHz, CDCl3): 0.95 (t, 3H), 1.92 (m, 2H), 2.69 (m, 2H), 3.30 (m, 1H), 3.83 (s, 3H), 4.22 (d, 1H), 4.85 (q, 1H), 5.18 (m, 4H), 5.80 (m, 1H), 6.85 (br, d, 1H), 7.45 (m, 9H). Anal. C25H28N2O5, Mol. Wt.: 436.5. Found: ESI-MS: 437.1 (M+H)+. | C=CC[C@H]1C(=O)N(C(=O)NC(CC)c2ccccc2)[C@@H]1C(=O)OCc1ccc(OC)cc1 | null | C=CC[C@H]1C(=O)N[C@@H]1C(=O)OCc1ccc(OC)cc1 | CCC(N=C=O)c1ccccc1 | null | [CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][O:8][C:9]([C@@H:11]2[C@@H:14]([CH2:15][CH:16]=[CH2:17])[C:13](=[O:18])[NH:12]2)=[O:10])=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH2:28]([CH:30]([N:37]=[C:38]=[O:39])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH3:29]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]([C@@H:11]2[C@@H:14]([CH2:15][CH:16]=[CH2:17])[C:13](=[O:18])[N:12]2[C:38](=[O:39])[NH:37][CH:30]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:28][CH3:29])=[O:10])=[CH:19][CH:20]=1 | 8 | CCN(CC)CC | ClCCl | null | null | null | 58.3 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,546,236 | null | null | null | null | ord_dataset-cac8df8aff894288876df4e093c9877f | 2015-01-01T00:02:00 | true | A stirred mixture of 3-iodo-1-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)pyrazin-2(1H)-one (750 mg, 1.81 mmol), ammonia (7 M solution in MeOH, 2 mL, 14 mmol), and DMSO (1.5 mL), was heated in a Biotage Microwave Synthesizer at 150° C. for 15 min. The mixture was cooled to and partitioned between EtOAc and a 1:1 mixture of water and brine. The organic layer was separated, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with a gradient of 100% DCM to 2% MeOH in DCM to afford 3-amino-1-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)pyrazin-2(1H)-one (149 mg) as a yellow solid. 1H NMR (500 MHz, DMSO-d6) δ 7.96 (s, 1H), 7.82 (d, J=8.4 Hz, 1H), 7.43 (dd, J=1.5, 8.4 Hz, 1H), 6.92 (d, J=4.7 Hz, 1H), 6.65-6.67 (br m, 3H), 5.11 (s, 2H), 2.78 (s, 3H); LCMS (ESI) m/z 305 (M+H)+. | CSc1nc2ccc(Cn3ccnc(N)c3=O)cc2s1 | null | CSc1nc2ccc(Cn3ccnc(I)c3=O)cc2s1 | N | null | I[C:2]1[C:3](=[O:20])[N:4]([CH2:8][C:9]2[CH:19]=[CH:18][C:12]3[N:13]=[C:14]([S:16][CH3:17])[S:15][C:11]=3[CH:10]=2)[CH:5]=[CH:6][N:7]=1.[NH3:21]>CS(C)=O>[NH2:21][C:2]1[C:3](=[O:20])[N:4]([CH2:8][C:9]2[CH:19]=[CH:18][C:12]3[N:13]=[C:14]([S:16][CH3:17])[S:15][C:11]=3[CH:10]=2)[CH:5]=[CH:6][N:7]=1 | null | CS(C)=O | null | null | 150 | 27 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
951,456 | [H-] | [Na+] | null | null | ord_dataset-3feb2a95f66e4706a4a50c977ccd9bf8 | 2010-01-01T00:04:00 | true | To a mixture of 1-piperidinemethanol (1.3 g, 10 mmol) and tetrahydrofuran (30 ml) was added sodium hydride (60%, 418 mg, 10 mmol) at 0° C. (external temperature), followed by stirring at room temperature for 30 minutes. Then, to the reaction mixture was added dropwise a mixture of tributyl-iodomethyl-tin (3.0 g, 7.0 mmol), tetrahydrofuran (5 ml), and N,N-dimethylformamide (30 ml) at 0° C. Then, the reaction mixture was stirred at room temperature for 1 hour. To the reaction mixture were added water and ethyl acetate, and the organic layer was separated. The organic layer was sequentially washed with water and an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=20:1, NH silica gel) to obtain the title compound (2.1 g, 4.9 mmol, 70%). | CCCC[Sn](CCCC)(CCCC)COCCN1CCCCC1 | null | CCCC[Sn](CI)(CCCC)CCCC | OCN1CCCCC1 | C1CCOC1 | [N:1]1([CH2:7]O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[O:9]1CCC[CH2:10]1.[H-].[Na+].[CH2:16]([Sn:20]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:21]I)[CH2:17][CH2:18][CH3:19]>C(OCC)(=O)C.O.CN(C)C=O>[CH2:16]([Sn:20]([CH2:21][O:9][CH2:10][CH2:7][N:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:23][CH2:24][CH2:25][CH3:26])[CH2:17][CH2:18][CH3:19] | 0.5 | CCOC(C)=O | CN(C)C=O | O | 25 | 70 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
292,119 | [Na+] | [OH-] | null | null | ord_dataset-6c3ec086c8c9475e8d31a44641b49e02 | 1994-01-01T00:06:00 | true | Aqueous sodium hydroxide (15.4 g, 192 mL, 0.08 g/mL solution, 0.38 mol) was added to a solution of dipeptide 25 (187.1 g, ca. 0.38 mol), water (360 mL) and MeOH (ca. 6 L). The solution was stirred at room temperature until hydrolysis was complete (ca. 24 hours). The disappearance of the starting peptide was established by HPLC analysis. The solution was concentrated in vacuo to a residue which was dissolved in water (ca. 1 L). The aqueous layer (pH ca. 10) was then extracted with EtOAc (2×500 mL) in a separatory funnel. The resulting aqueous phase was adjusted to a pH of 5 with concentrated HCl at which point a crystalline precipitate formed. The solid was collected by vacuum filtration and dried in vacuo (148.4 g, 0.31 mol, 82%). The pH of the filtrate was adjusted to 4.5. A second crop of solid was again collected by vacuum filtration and dried in vacuo (20.2 g, 0.043 mol, 11%). 1H NMR showed both samples to contain dipeptide 26 in high purity. In two repetitions of this reaction, yields of 83% (ca. 0.06 mole scale) and 58% (ca. 0.3 mole scale) were obtained. | O=C(N[C@@H](Cc1c[nH]cn1)C(=O)N[C@H](Cc1c[nH]c2ccccc12)C(=O)O)OCc1ccccc1 | null | COC(=O)[C@@H](Cc1c[nH]c2ccccc12)NC(=O)[C@H](Cc1c[nH]cn1)NC(=O)OCc1ccccc1 | null | null | [OH-].[Na+].C[O:4][C:5](=[O:38])[C@@H:6]([CH2:28][C:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[NH:31][CH:30]=1)[NH:7][C:8](=[O:27])[C@H:9]([CH2:21][C:22]1[N:26]=[CH:25][NH:24][CH:23]=1)[NH:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12].O>CO>[CH2:14]([O:13][C:11]([NH:10][C@H:9]([C:8]([NH:7][C@@H:6]([C:5]([OH:38])=[O:4])[CH2:28][C:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[NH:31][CH:30]=1)=[O:27])[CH2:21][C:22]1[N:26]=[CH:25][NH:24][CH:23]=1)=[O:12])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1 | null | CO | O | null | 25 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,645,904 | Cl | null | null | null | ord_dataset-bcc0b01d4f58457a8733b10a099f43ba | 2015-01-01T00:10:00 | true | Title compound was prepared according to the method employed to prepare (S)-1-((S)-8-(5-(4-(6-(2-((S)-1-((R)-2-(methoxycarbonylamino)-2-phenylacetyl)pyrrolidin-2-yl)-1H-imidazol-5-yl)naphthalen-2-yl)phenyl)-1H-imidazol-2-yl)-1,4-dioxa-7-azaspiro[4.4]nonan-7-yl)-3-methyl-1-oxobutan-2-ylcarbamic acid methyl ester, except that methyl (S)-2-((S)-8-(6-(9,9-difluoro-7-(2-((S)-pyrrolidin-2-yl)-1H-imidazol-5-yl)-9H-fluoren-2-yl)-1H-benzo[d]imidazol-2-yl)-1,4-dioxa-7-azaspiro[4.4]nonan-7-yl)-2-oxo-1-(tetrahydro-2H-pyran-4-yl)ethylcarbamate 3× HCl salt was used instead of methyl (S)-3-methyl-1-oxo-1-((S)-8-(5-(4-(6-(2-((S)-pyrrolidin-2-yl)-1H-imidazol-5-yl)naphthalen-2-yl)phenyl)-1H-imidazol-2-yl)-1,4-dioxa-7-azaspiro[4.4]nonan-7-yl)butan-2-ylcarbamate 3HCl salt. MS (ESI) m/z 972.54 [M+H]+. (30 mg, 43%). | COC(=O)N[C@H](C(=O)N1CC2(C[C@H]1c1nc3ccc(-c4ccc5c(c4)C(F)(F)c4cc(-c6cnc([C@@H]7CCCN7C(=O)[C@H](NC(=O)OC)c7ccccc7)[nH]6)ccc4-5)cc3[nH]1)OCCO2)C1CCOCC1 | null | COC(=O)N[C@H](C(=O)N1CC2(C[C@H]1c1ncc(-c3ccc(-c4ccc5cc(-c6cnc([C@@H]7CCCN7C(=O)[C@H](NC(=O)OC)c7ccccc7)[nH]6)ccc5c4)cc3)[nH]1)OCCO2)C(C)C | COC(=O)N[C@H](C(=O)N1CC2(C[C@H]1c1nc3ccc(-c4ccc5c(c4)C(F)(F)c4cc(-c6cnc([C@@H]7CCCN7)[nH]6)ccc4-5)cc3[nH]1)OCCO2)C1CCOCC1 | null | COC(=O)N[C@@H](C(C)C)C(N1[C@H](C2NC(C3C=CC(C4C=CC5C(=CC=C(C6NC([C@@H]7CCCN7[C:48](=[O:61])[C@H:49]([NH:56][C:57]([O:59][CH3:60])=[O:58])[C:50]7[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=7)=NC=6)C=5)C=4)=CC=3)=CN=2)CC2(OCCO2)C1)=O.[F:66][C:67]1([F:122])[C:79]2[CH:78]=[C:77]([C:80]3[CH:81]=[CH:82][C:83]4[N:87]=[C:86]([C@@H:88]5[CH2:96][C:91]6([O:95][CH2:94][CH2:93][O:92]6)[CH2:90][N:89]5[C:97](=[O:110])[C@@H:98]([NH:105][C:106](=[O:109])[O:107][CH3:108])[CH:99]5[CH2:104][CH2:103][O:102][CH2:101][CH2:100]5)[NH:85][C:84]=4[CH:111]=3)[CH:76]=[CH:75][C:74]=2[C:73]2[C:68]1=[CH:69][C:70]([C:112]1[NH:116][C:115]([C@@H:117]3[CH2:121][CH2:120][CH2:119][NH:118]3)=[N:114][CH:113]=1)=[CH:71][CH:72]=2.Cl>>[CH3:108][O:107][C:106](=[O:109])[NH:105][C@@H:98]([CH:99]1[CH2:104][CH2:103][O:102][CH2:101][CH2:100]1)[C:97]([N:89]1[C@H:88]([C:86]2[NH:85][C:84]3[CH:111]=[C:80]([C:77]4[CH:76]=[CH:75][C:74]5[C:73]6[C:68](=[CH:69][C:70]([C:112]7[NH:116][C:115]([C@@H:117]8[CH2:121][CH2:120][CH2:119][N:118]8[C:48](=[O:61])[C@H:49]([NH:56][C:57]([O:59][CH3:60])=[O:58])[C:50]8[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=8)=[N:114][CH:113]=7)=[CH:71][CH:72]=6)[C:67]([F:66])([F:122])[C:79]=5[CH:78]=4)[CH:81]=[CH:82][C:83]=3[N:87]=2)[CH2:96][C:91]2([O:95][CH2:94][CH2:93][O:92]2)[CH2:90]1)=[O:110] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
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