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 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
101,493 | O=C([O-])[O-] | [K+] | null | null | ord_dataset-d06b137b66b3478fb6a0d41a5efd32f8 | 1982-01-01T00:12:00 | true | 4-(Pentafluorophenyl)-1-carbethoxysemicarbazide, 2.13 g (0.0068 M), and potassium carbonate, 0.938 g (0.0068 M), are added to 75 ml of water. The mixture is heated at 70° C. under N2 about 12 hours. The solution is cooled in an ice bath and filtered to remove a trace of starting material. The pH of the solution is adjusted to pH 7 with concentrated HCl and extracted with ethyl acetate to remove a product which is less polar than the urazole in the TLC system, chloroform/ethyl acetate/acetic acid (5/5/1). The pH of the solution is reduced to 1 or 2 with concentrated HCl and then extracted with ethyl acetate. About 1/3 of a volume of toluene is added to the ethyl acetate and the solvents evaporated. The resulting crude solid weighs 0.569 g. The product is purified by two crystallizations from ethyl acetate/toluene (1/3 by vol). The yield of purified material is 0.476 g. It is recrystallized from H2O, mp 223°-226°. | O=c1[nH][nH]c(=O)n1-c1c(F)c(F)c(F)c(F)c1F | null | CCOC(=O)NNC(=O)Nc1c(F)c(F)c(F)c(F)c1F | null | null | [F:1][C:2]1[C:7]([NH:8][C:9](=[O:17])[NH:10][NH:11][C:12](OCC)=[O:13])=[C:6]([F:18])[C:5]([F:19])=[C:4]([F:20])[C:3]=1[F:21].C(=O)([O-])[O-].[K+].[K+]>O>[F:18][C:6]1[C:7]([N:8]2[C:9](=[O:17])[NH:10][NH:11][C:12]2=[O:13])=[C:2]([F:1])[C:3]([F:21])=[C:4]([F:20])[C:5]=1[F:19] | null | O | null | null | 70 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
513,304 | O=S(=O)(O)O | [NH4+] | [OH-] | null | ord_dataset-85c00026681b46f89ef8634d2b8618c3 | 2001-01-01T00:07:00 | true | Quinoline (Formula (1), 12.9 g, 0.10 mole) was added dropwise over 5 min. with good agitation to a solution of 50 mL of concentrated sulfuric acid in a 250 mL round bottom flask. No attempt was made to control the exotherm and on this scale the final temperature was 77° C. The mixture was heated to 100° C. and 71% nitric acid (13.3 g, d. 1.42, 9.4 mL, 0.15 mole) was added at such a rate to keep the temperature between 100° C. and 110° C. Stirring was continued for an additional 30 minutes or until an HPLC (Zorbax® SB-C18 HPLC column, from Mac-Mod Analytical, Inc. of Chadds Ford, Pa. U.S.A.; dimensions 4½ mm (inside diameter) by 25 cm (length); HPLC conditions: 40:60 acetonitrile:water-0.5% ammonium acetate, 220 nm, flow 0.5 mL/min.) sample showed the reaction was complete. The mixture was cooled slightly and poured onto a mixture of 200 mL methylene chloride and 300 mL (by volume) of ice. The two phase mixture was placed in an ice bath and the temperature was kept below 25° C. while the pH was increased to 10 with concentrated ammonium hydroxide. The mixture was vacuum filtered through paper and transferred to a separatory funnel. The lower organic phase was separated and the aqueous layer was extracted with an additional 100 mL of methylene chloride. The combined organic layers were dried over magnesium sulfate, filtered and evaporated affording 15.8 g (91% yield) of a clear light amber oil which crystallized on standing. HPLC Analysis was conducted for 5-nitroquinoline and 8-nitroquinoline only: 45% 8-nitroquinoline (Formula (3), rt 9.0 min.) and 55% 5-nitroquinoline (Formula (2), rt 12.8 min). | O=[N+]([O-])c1ccc2ccccc2n1 | null | O=[N+]([O-])O | c1ccc2ncccc2c1 | null | [N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[N+:16]([O-])([OH:18])=[O:17].[OH-].[NH4+]>C(Cl)Cl.O.C(#N)C>[N+:16]([C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]=1)([O-:18])=[O:17] | null | CC#N | ClCCl | O | 100 | null | 90.7 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,567,738 | CN(C)C(On1nnc2ccccc21)=[N+](C)C | Cl | F[P-](F)(F)(F)(F)F | null | ord_dataset-9741bb5fd93044078df2a45f45733054 | 2015-01-01T00:04:00 | true | To a mixture of 4-isobutoxy-6-(piperazin-1-yl)pyrimidine dihydrochloride (30 mg, 0.097 mmol), (R)-2-hydroxy-2-phenylacetic acid (15 mg, 0.097 mmol), and triethylamine (0.07 mL, 0.49 mmol) in DMF was added HBTU (48 mg, 0.13 mmol), and the mixture was stirred at rt for 1 h. Then the mixture was poured onto water (3 mL), and the aqueous layer was extracted with dichloromethane (three times). The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was purified by preparative LC-MS to give 7.2 mg (15% yields) of the title compound. | CC(C)COc1cc(N2CCN(C(=O)[C@H](O)c3ccccc3)CC2)ncn1 | null | O=C(O)[C@H](O)c1ccccc1 | CC(C)COc1cc(N2CCNCC2)ncn1 | null | Cl.Cl.[CH2:3]([O:7][C:8]1[CH:13]=[C:12]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[N:11]=[CH:10][N:9]=1)[CH:4]([CH3:6])[CH3:5].[OH:20][C@H:21]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:22](O)=[O:23].C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[OH:20][C@H:21]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:22]([N:17]1[CH2:18][CH2:19][N:14]([C:12]2[CH:13]=[C:8]([O:7][CH2:3][CH:4]([CH3:6])[CH3:5])[N:9]=[CH:10][N:11]=2)[CH2:15][CH2:16]1)=[O:23] | 1 | CN(C)C=O | CCN(CC)CC | 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 |
1,413,565 | null | null | null | null | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | 2014-01-01T00:04:00 | true | A solution of 2-(3-Amino-phenyl)-ethanol (2.0 g) in 48% aq HBr (20 ml) was heated at 90° C. for 18 h. The mixture was cooled to room temperature, and the precipitate formed was collected by filtration. The solid was dried in vacuo yielding Building block M, 1.8 g (61% yield). LCMS purity 90%, m/z 200/202 [M+H]+. | Nc1cccc(CCBr)c1 | null | Br | Nc1cccc(CCO)c1 | null | [NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9]O)[CH:5]=[CH:6][CH:7]=1.[BrH:11]>>[Br:11][CH2:9][CH2:8][C:4]1[CH:3]=[C:2]([NH2:1])[CH:7]=[CH:6][CH:5]=1 | null | null | null | null | 25 | 61 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,759,593 | c1ccc([P]([Pd][P](c2ccccc2)(c2ccccc2)c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [Cs+] | null | ord_dataset-97eb2ab57fec4160922caae33b54d956 | 2016-01-01T00:08:00 | true | A 50-mL round bottomed flask fitted with a nitrogen inlet and magnetic stir bar was charged with (S)-isopropyl 7-bromo-4-(cyclopropanecarbonyl)-3-methyl-3,4-dihydroquinoxaline-1(2H)-carboxylate (0.801 g, 2.1 mmol), dioxane (11 mL), and water (4.6 mL). Cesium carbonate (2.053 g, 6.30 mmol) and tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-carboxylate (0.927 g, 3.15 mmol) were then added. The reaction was purged with nitrogen and bis(triphenylphosphine)palladium (II) dichloride (0.177 g, 0.252 mmol) was added. The mixture was heated at 90° C. with vigorous stirring for 5 h and then cooled to ambient temperature. Water (25 mL) was added, and the mixture was extracted with ethyl acetate (3×25 mL). The combined organic extracts were concentrated to afford a viscous oil and purified via column chromatography (gradient elution with 75-100% ethyl acetate-hexanes). The resulting material was triturated with diethyl ether (2×10 mL) to afford (S)-isopropyl 4-(cyclopropanecarbonyl)-3-methyl-7-(1H-pyrazol-4-yl)-3,4-dihydroquinoxaline-1(2H)-carboxylate (0.55 g, 71% yield) as a solid. MS (ESI, pos. ion) m/z 369 [M+1]+. | CC(C)OC(=O)N1C[C@H](C)N(C(=O)C2CC2)c2ccc(-c3cn[nH]c3)cc21 | null | CC(C)OC(=O)N1C[C@H](C)N(C(=O)C2CC2)c2ccc(Br)cc21 | CC(C)(C)OC(=O)n1cc(B2OC(C)(C)C(C)(C)O2)cn1 | null | Br[C:2]1[CH:11]=[C:10]2[C:5]([N:6]([C:19]([CH:21]3[CH2:23][CH2:22]3)=[O:20])[C@@H:7]([CH3:18])[CH2:8][N:9]2[C:12]([O:14][CH:15]([CH3:17])[CH3:16])=[O:13])=[CH:4][CH:3]=1.O1CCOCC1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C(C)(C)OB([C:44]2[CH:45]=[N:46][N:47](C(OC(C)(C)C)=O)[CH:48]=2)O1>C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[CH:21]1([C:19]([N:6]2[C:5]3[C:10](=[CH:11][C:2]([C:44]4[CH:45]=[N:46][NH:47][CH:48]=4)=[CH:3][CH:4]=3)[N:9]([C:12]([O:14][CH:15]([CH3:17])[CH3:16])=[O:13])[CH2:8][C@@H:7]2[CH3:18])=[O:20])[CH2:23][CH2:22]1 | 5 | C1COCCO1 | O | null | 90 | 71.1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,703,177 | CCN=C=NCCCN(C)C | CN(C)c1ccncc1 | Cl | null | ord_dataset-54347fcace774f89850681d6dec8009f | 2016-01-01T00:03:00 | true | Into a 10-mL round bottom flask, was placed a solution of 3-(((2-(diethylamino)ethyl)(methyl)amino)methyl)benzoic acid (118.8 mg, 0.45 mmol, 1.50 equiv) in dichloromethane (24 mL), EDC.HCl (171.6 mg, 0.90 mmol, 3.00 equiv), 4-dimethylaminopyridine (182.4 mg, 1.49 mmol, 5.00 equiv), and 2-amino-N-(5-(3,4-dimethylphenyl)pyrimidin-2-yl)-5-(piperidin-1-yl)benzamide (120 mg, 0.29 mmol, 1.00 equiv). The resulting solution was stirred for 8 h at 25° C. in an oil bath. The resulting mixture was concentrated under vacuum. The crude product (200 mg) was purified by reverse phase HPLC eluting with a water/CH3CN gradient containing 0.05% TFA. The product was obtained as 139.2 mg (62%) of a yellow solid. 1H-NMR (300 MHz, DMSO, ppm): δ 11.37 (s, 1H), 11.30 (s, 1H), 8.75 (d, J=6 Hz, 2H), 8.22 (d, J=9 Hz, 1H), 8.054 (s, 1H), 7.93 (d, J=6.3 Hz, 1H), 7.68˜7.60 (m, 2H), 7.53 (s, 1H), 7.31˜7.20 (m, 3H), 7.15 (d, J=7.2 Hz, 1H), 3.40˜3.12 (m, 13H), 2.59 (s, 2H), 2.32˜2.27 (m, 4H), 2.16 (s, 3H), 1.68 (m, 4H), 1.58˜1.57 (m, 2H), 1.21˜1.16 (m, 6H). MS (ES, m/z): 648 [M−H]+. | CCN(CC)CCN(C)Cc1cccc(C(=O)Nc2ccc(N3CCCCC3)cc2C(=O)Nc2ncc(-c3ccc(C)c(C)c3)cn2)c1 | null | Cc1ccc(-c2cnc(NC(=O)c3cc(N4CCCCC4)ccc3N)nc2)cc1C | CCN(CC)CCN(C)Cc1cccc(C(=O)O)c1 | null | [CH2:1]([N:3]([CH2:18][CH3:19])[CH2:4][CH2:5][N:6]([CH2:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([OH:14])=O)[CH3:7])[CH3:2].CCN=C=NCCCN(C)C.Cl.[NH2:32][C:33]1[CH:55]=[CH:54][C:53]([N:56]2[CH2:61][CH2:60][CH2:59][CH2:58][CH2:57]2)=[CH:52][C:34]=1[C:35]([NH:37][C:38]1[N:43]=[CH:42][C:41]([C:44]2[CH:49]=[CH:48][C:47]([CH3:50])=[C:46]([CH3:51])[CH:45]=2)=[CH:40][N:39]=1)=[O:36]>ClCCl.CN(C)C1C=CN=CC=1>[CH2:18]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][N:6]([CH2:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([NH:32][C:33]1[CH:55]=[CH:54][C:53]([N:56]2[CH2:61][CH2:60][CH2:59][CH2:58][CH2:57]2)=[CH:52][C:34]=1[C:35]([NH:37][C:38]1[N:43]=[CH:42][C:41]([C:44]2[CH:49]=[CH:48][C:47]([CH3:50])=[C:46]([CH3:51])[CH:45]=2)=[CH:40][N:39]=1)=[O:36])=[O:14])[CH3:7])[CH3:19] | 8 | ClCCl | null | null | 25 | 74.1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
607,296 | [Na+] | [OH-] | null | null | ord_dataset-273fda773e864aaf9b71a30a2d9f2162 | 2003-01-01T00:08:00 | true | To a well-stirred reaction vessel equipped with a thermometer and a pH electrode were added 39 g of water and 0.20 g of Arquad CB50 at 5° C. After the addition of 0.05 mole of 3-chlorobenzoic acid the pH was adjusted to 6 using a 10 wt % aqueous NaOH solution. Then, 0.05 mole of sec-butyl chloroformate was dosed within 5 min at 5° C. During this time and a post-reaction time of 165 min at 5° C. the pH was kept at a value between 6 and 9. The reaction mixture was allowed to separate, giving 12.5 g of 3-chlorobenzoyl 1-methyl-1-propyl carbonate having a content of 98% in a yield of 95%. | CCC(C)OC(=O)OC(=O)c1cccc(Cl)c1 | null | O=C(O)c1cccc(Cl)c1 | CCC(C)OC(=O)Cl | null | [Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[OH-].[Na+].Cl[C:14]([O:16][CH:17]([CH2:19][CH3:20])[CH3:18])=[O:15]>O>[C:14](=[O:15])([O:16][CH:17]([CH3:18])[CH2:19][CH3:20])[O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][CH:10]=[C:2]([Cl:1])[CH:3]=1 | null | O | null | null | null | 97.4 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,648,404 | [Na+] | [OH-] | null | null | ord_dataset-bcc0b01d4f58457a8733b10a099f43ba | 2015-01-01T00:10:00 | true | To a solution of 1-(dodecylamino)-4-(methylsulfinyl)-1-oxobutan-2-yl acetate (25 g, 62.6 mmol) in methanol (350 mL) was added 2.5 N NaOH (40 mL, 100 mmol) and the resulting solution was stirred at room temperature for 5 hrs. The reaction was quenched with concentrated HCL (12.5 mL) and then evaporated to a small volume. The resulting mixture was treated with EtOAc (200 mL) and then washed with 1N HCl (150 mL), saturated sodium bicarbonate (50 mL), dried over magnesium sulfate, filtered and evaporated to give a solid. The solid was dissolved in dichloromethane and purified by silica gel chromatography with 0-10% methanol/dichloromethane. The desired fractions were collected and evaporated to give a white solid (16.7 g, 80%). 1H NMR (500 MHz, DMSO-d6) δ ppm 0.85 (t, J=6.83 Hz, 3 H) 1.15-1.33 (m, 18 H) 1.33-1.46 (m, 2 H) 1.72-1.87 (m, 1 H) 1.92-2.09 (m, 1 H) 2.51 (d, J=1.27 Hz, 3 H) 2.56-2.87 (m, 2 H) 3.00-3.12 (m, 2 H) 3.90-4.00 (m, 1 H) 5.69 (d, J=5.40 Hz, 1 H) 7.71-7.82 (m, 1 H). m/z 334 (MH+). | CCCCCCCCCCCCNC(=O)C(O)CCS(C)=O | null | CCCCCCCCCCCCNC(=O)C(CCS(C)=O)OC(C)=O | null | null | C([O:4][CH:5]([CH2:21][CH2:22][S:23]([CH3:25])=[O:24])[C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[O:7])(=O)C.[OH-].[Na+]>CO.ClCCl>[CH2:9]([NH:8][C:6](=[O:7])[CH:5]([OH:4])[CH2:21][CH2:22][S:23]([CH3:25])=[O:24])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20] | 5 | CO | ClCCl | null | 25 | null | 80 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,541,277 | null | null | null | null | ord_dataset-cac8df8aff894288876df4e093c9877f | 2015-01-01T00:02:00 | true | A mixture of 1-benzyl-1,2,3,4-tetrahydroquinolin-7-ol (500 mg, 2.09 mM) and triethylamine in dry tetrahydrofuran (THF, 5 ml) was stirred for half an hour under nitrogen atmosphere at room temperature (35° C.). To the stirred reaction mixture, 2-methoxyphenyl isocyanate (417 mg/ml, 3.14 mM) was added at once and then the reaction mixture was further stirred for 72 hours under N2 atmosphere at RT. The reaction mixture was concentrated under vacuum and then was added distilled water (15 mL) followed by the extraction with ether (3×15 mL). The ether layer was dried over sodium sulphate and concentrated under vacuum to afford the crude product, which was finally chromatographed using chloroform-hexane (1:9) to give 8i as solid. Yield: 0.623 g, 76.85%. | COc1ccccc1NC(=O)Oc1ccc2c(c1)N(Cc1ccccc1)CCC2 | null | COc1ccccc1N=C=O | Oc1ccc2c(c1)N(Cc1ccccc1)CCC2 | null | [CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([OH:18])[CH:16]=2)[CH2:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:26][O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[N:34]=[C:35]=[O:36]>O1CCCC1>[CH3:26][O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[NH:34][C:35](=[O:36])[O:18][C:15]1[CH:16]=[C:17]2[C:12]([CH2:11][CH2:10][CH2:9][N:8]2[CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:13][CH:14]=1 | null | CCN(CC)CC | C1CCOC1 | null | 35 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
427,386 | null | null | null | null | ord_dataset-8cce6f317d644b348a7978a2dce3ea01 | 1999-01-01T00:03:00 | true | Following a procedure and using relative proportions of starting materials similar to those described in Example 4, but using tert-butyl (4-methyl-1-methylthiocarbazol-2-yl)acetate and 4-fluorobenzyl bromide as starting materials, the title compound was obtained in a yield of 91% as an oil. | CSc1c(CC(=O)OC(C)(C)C)cc(C)c2c3ccccc3n(Cc3ccc(F)cc3)c12 | null | CSc1c(CC(=O)OC(C)(C)C)cc(C)c2c1[nH]c1ccccc12 | Fc1ccc(CBr)cc1 | null | [CH3:1][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[C:5]([S:15][CH3:16])=[C:4]([CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:3]=1.[F:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30]Br)=[CH:28][CH:27]=1>>[F:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30][N:7]2[C:6]3[C:5]([S:15][CH3:16])=[C:4]([CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:3]=[C:2]([CH3:1])[C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)=[CH:28][CH:27]=1 | null | null | null | null | null | 91 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,717,329 | [Na+] | [OH-] | null | null | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | 2016-01-01T00:04:00 | true | [5-(4-Bromo-phenyl)-3-methyl-3H-[1,2,3]triazol-4-yl]-carbamic acid (R)-1-phenyl-ethyl ester (from Example 1, 566 mg, 1.41 mmol), methyl 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclopropanecarboxylate (511 mg, 1.69 mmol), X-Phos (134 mg, 0.28 mmol), palladium acetate (31.7 mg, 0.14 mmol) and potassium phosphate (898 mg, 4.23 mmol) were combined in toluene (12 mL) and degassed water (3 mL) was added. The mixture was degassed and sealed. The mixture was stirred at 95° C. for 3 hrs and cooled to room temperature. The mixture was extracted with ethyl acetate and water. The organic layer was washed with brine and dried. Solvents were evaporated and the residue was purified by flash column chromatography (40 g silica gel, ethyl acetate in hexanes 10% to 70% in 15 minutes) to give 1-{4′-[1-methyl-5-((R)-1-phenyl-ethoxycarbonylamino)-1H-[1,2,3]triazol-4-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid methyl ester as a pale yellow solid (370 mg, 52.8% yield). LC/MS calcd for C29H28N4O4 (m/e) 496.0, obsd 497.0 (M+H); 1H-NMR (400 MHz, CDCl3) δ ppm 1.25 (m, 3H), 1.66 (m, 4H), 3.67 (s, 3H), 3.93 (s, 3H), 5.91 (m, 1H), 6.44 (br, 1H), 7.29-7.40 (m, 5H), 7.44 (d, J=8.1 Hz, 2H), 7.57 (d, J=8.3 Hz, 2H), 7.61 (d, J=8.3 Hz, 2H), 7.78 (br d, J=6.6 Hz, 2H). 1-{4′-[1-Methyl-5-((R)-1-phenyl-ethoxycarbonylamino)-1H-[1,2,3]triazol-4-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid methyl ester (50 mg) was dissolved in 1 mL of THF and 1 mL of ethanol. To this mixture was added 1N sodium hydroxide solution (1 mL). The clear solution was stirred at room temperature for 12 hrs. Solvents were evaporated and the residue was treated with 2N hydrochloric acid (1.4 mL). The solid was filtered and rinsed with water, dried in the air, to give 1-{4′-[1-methyl-5-((R)-1-phenyl-ethoxycarbonylamino)-1H-[1,2,3]triazol-4-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid (47.5 mg, 97.8% yield). LC/MS calcd for C28H26N4O4 (m/e) 482.0, obsd 483.0 (M+H); 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.14-1.24 (m, 3H), 1.49 (m, 2H), 1.59 (m, 2H), 3.86 (s, 3H), 5.80 (m, 1H), 7.28-7.50 (m, 7H), 7.63 (d, J=8.1 Hz, 2H), 7.71 (m, 2H), 7.80 (d, J=7.6 Hz, 2H), 9.95 and 9.62 (br s, 1H), 12.35 (s, 1H). | C[C@@H](OC(=O)Nc1c(-c2ccc(-c3ccc(C4(C(=O)O)CC4)cc3)cc2)nnn1C)c1ccccc1 | null | COC(=O)C1(c2ccc(-c3ccc(-c4nnn(C)c4NC(=O)O[C@H](C)c4ccccc4)cc3)cc2)CC1 | null | null | C[O:2][C:3]([C:5]1([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][C:17]([C:20]4[N:21]=[N:22][N:23]([CH3:37])[C:24]=4[NH:25][C:26]([O:28][C@@H:29]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[CH3:30])=[O:27])=[CH:16][CH:15]=3)=[CH:10][CH:9]=2)[CH2:7][CH2:6]1)=[O:4].[OH-].[Na+]>C1COCC1.C(O)C>[CH3:37][N:23]1[C:24]([NH:25][C:26]([O:28][C@@H:29]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH3:30])=[O:27])=[C:20]([C:17]2[CH:18]=[CH:19][C:14]([C:11]3[CH:10]=[CH:9][C:8]([C:5]4([C:3]([OH:4])=[O:2])[CH2:7][CH2:6]4)=[CH:13][CH:12]=3)=[CH:15][CH:16]=2)[N:21]=[N:22]1 | 12 | C1CCOC1 | CCO | null | 25 | null | 97.8 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,171,928 | [K+] | [OH-] | null | null | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | 2012-01-01T00:05:00 | true | Potassium hydroxide (108 mg, 1.93 mmol) was added in one portion to (S)-methyl 2-(2-(4′-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)-2-chlorobiphenyl-4-yl)acetamido)-3-methylbutanoate (Intermediate 17-1; 327.4 mg, 0.64 mmol) in t-BuOH (4150 μL) at RT. The resulting solution was stirred at 45° C. for 5 hours a precipitate formed. The reaction mixture was quenched with 2M HCl (5 mL), The reaction mixture was evaporated to dryness and redissolved in water (10 mL), and filtered through nylon, washed with water and dried under vacuum. The crude product was purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5μ silica, 50 mm diameter, 150 mm length), using decreasingly polar mixtures of water (containing 0.1% formic acid) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford (S)-2-(2-(4′-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)-2-chlorobiphenyl-4-yl)acetamido)-3-methylbutanoic acid (93 mg, 29.1%) as a white solid. | Cc1nc(C)c(-c2ccc(-c3ccc(CC(=O)N[C@H](C(=O)O)C(C)C)cc3Cl)cc2)nc1C(N)=O | null | COC(=O)[C@@H](NC(=O)Cc1ccc(-c2ccc(-c3nc(C(N)=O)c(C)nc3C)cc2)c(Cl)c1)C(C)C | null | null | [OH-].[K+].[C:3]([C:6]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][C:25]([NH:27][C@@H:28]([CH:33]([CH3:35])[CH3:34])[C:29]([O:31]C)=[O:30])=[O:26])=[CH:20][C:19]=3[Cl:36])=[CH:14][CH:13]=2)[C:9]([CH3:37])=[N:8][C:7]=1[CH3:38])(=[O:5])[NH2:4]>CC(O)(C)C>[C:3]([C:6]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][C:25]([NH:27][C@@H:28]([CH:33]([CH3:34])[CH3:35])[C:29]([OH:31])=[O:30])=[O:26])=[CH:20][C:19]=3[Cl:36])=[CH:14][CH:13]=2)[C:9]([CH3:37])=[N:8][C:7]=1[CH3:38])(=[O:5])[NH2:4] | 5 | CC(C)(C)O | null | null | 45 | null | 29.4 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,472,442 | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [K+] | null | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | 2014-01-01T00:08:00 | true | A mixture of the compound obtained from step f above (1.0 g) (4-chlorophenyl)boronic acid (0.76 g), tetrakis(triphenylphosphine)palladium (0) (0.14 g), and potassium carbonate (1.0 g) in dry dimethylformamide (10 mL) was heated at 110° C. for 4 hours. Ethyl acetate and water were added to the reaction mixture. The organic layer was separated, washed with water and brine solution, and dried over anhydrous sodium sulphate. The solvent was evaporated under reduced pressure to obtain a residue which was purified by column chromatography over silica gel using 12% ethyl acetate in hexane as eluant to afford the title compound (0.9 g). | CCOC(=O)C[C@H]1[C@H]2OC(C)(C)O[C@H]2O[C@@H]1/C=C/c1ccc(-c2ccc(Cl)cc2)cc1 | null | OB(O)c1ccc(Cl)cc1 | CCOC(=O)C[C@H]1[C@H]2OC(C)(C)O[C@H]2O[C@@H]1/C=C/c1ccc(Br)cc1 | null | Br[C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C@H:10]2[O:19][C@@H:13]3[O:14][C:15]([CH3:18])([CH3:17])[O:16][C@@H:12]3[C@@H:11]2[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:4][CH:3]=1.[Cl:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([C:2]2[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C@H:10]3[O:19][C@@H:13]4[O:14][C:15]([CH3:18])([CH3:17])[O:16][C@@H:12]4[C@@H:11]3[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:4][CH:3]=2)=[CH:29][CH:28]=1 | null | O | CCOC(C)=O | CN(C)C=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 |
773,500 | Cl | null | null | null | ord_dataset-8214eb8444a44dc2900ccb42dbeff15e | 2007-01-01T00:05:00 | true | 1-(4-Chloro-phenyl)-5-trifluoromethyl-1H-pyrazole-4-carbonyl chloride (0.250 g, 0.808 mmol) was added to a solution of 3-methylsulfonylaniline hydrochloride (0.184 g, 0.889 mmol) and triethylamine (0.563 mL, 4.04 mmol) in acetonitrile (20 mL). The reaction mixture heated at 60° C. for 12 h, concentrated and crude product purified by column chromatography on silica gel to give 1-(4-chloro-phenyl)-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid (3-methane sulfonyl-phenyl)-amide. 1H-NMR (CD3OD, 300 MHz) δ 8.37 (s, 1H), 8.17 (s, 1H), 7.97 (d, 1H, J=8.5 Hz), 7.73 (d, 1H, J=8.0 Hz), 7.59–7.66 (m, 3H), 7.51 (d, 2H, J=8.8 Hz), 3.15 (s, 3H); LCMS m/z=443.9 (M+H)+. | CS(=O)(=O)c1cccc(NC(=O)c2cnn(-c3ccc(Cl)cc3)c2C(F)(F)F)c1 | null | CS(=O)(=O)c1cccc(N)c1 | O=C(Cl)c1cnn(-c2ccc(Cl)cc2)c1C(F)(F)F | null | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]([F:16])([F:15])[F:14])=[C:11]([C:17](Cl)=[O:18])[CH:10]=[N:9]2)=[CH:4][CH:3]=1.Cl.[CH3:21][S:22]([C:25]1[CH:26]=[C:27]([CH:29]=[CH:30][CH:31]=1)[NH2:28])(=[O:24])=[O:23].C(N(CC)CC)C>C(#N)C>[CH3:21][S:22]([C:25]1[CH:26]=[C:27]([NH:28][C:17]([C:11]2[CH:10]=[N:9][N:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[C:12]=2[C:13]([F:16])([F:15])[F:14])=[O:18])[CH:29]=[CH:30][CH:31]=1)(=[O:23])=[O:24] | null | CC#N | CCN(CC)CC | null | 60 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,142,141 | null | null | null | null | ord_dataset-68715347640045adb1b09e6a04722b0e | 2012-01-01T00:03:00 | true | Method A using 3-Iodo-pyridine-2,6-diamine (Preparation 44), 1.6 equivalents of lutidine and 1.5 equivalents of acid chloride prepared from 2-isopropyl-2H-pyrazole-3-carboxylic acid. Purified by trituration with methanol:ethylacetate 1:2 to afford the title compound as a colourless oil (608 mg, 38%). | CC(C)n1nccc1C(=O)Nc1ccc(I)c(N)n1 | null | CC(C)n1nccc1C(=O)O | Nc1ccc(I)c(N)n1 | null | [I:1][C:2]1[C:3]([NH2:9])=[N:4][C:5]([NH2:8])=[CH:6][CH:7]=1.N1C(C)=CC=CC=1C.[CH:18]([N:21]1[C:25]([C:26](O)=[O:27])=[CH:24][CH:23]=[N:22]1)([CH3:20])[CH3:19]>>[NH2:9][C:3]1[N:4]=[C:5]([NH:8][C:26]([C:25]2[N:21]([CH:18]([CH3:20])[CH3:19])[N:22]=[CH:23][CH:24]=2)=[O:27])[CH:6]=[CH:7][C:2]=1[I:1] | null | Cc1cccc(C)n1 | null | null | null | null | 38 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,061,171 | O=C([O-])[O-] | [K+] | null | null | ord_dataset-ffbef48837674f39816de887b5dc8bae | 2011-01-01T00:06:00 | true | Potassium carbonate (4.42 g, 31.96 mmol) was suspended in dry MeOH (20 mL) and thioacetic acid (2.28 g, 29.96 mmol) was added. The mixture was stirred vigorously for 10 mins, concentrated and diluted in dry DMF (30 mL). tert-Butyl 3-[(methylsulfonyl)oxy]pyrrolidine-1-carboxylate (2.65 g, 9.99 mmol) dissolved in dry DMF (20 mL) was added and the reaction mixture was heated to 60° C. for 3.5 h. The reaction mixture was diluted with water (350 mL) and extracted with EtOAc (2×150 mL) The organic phases were dried with MgSO4, filtered and evaporated. The crude product was purified using Biotage Horizon HPFC system (25+M column, isocratic run heptane/EtOAc (60:40)) affording the title compound (0.592 g, 24.2%) (the product is a mixture of cis and trans isomers). 1H NMR (500 MHz, CDCl3): δ 1.41 (d, 18H), 1.66 (d, 1H), 1.74-1.86 (m, 2H), 2.20-2.26 (m, 2H), 2.29 (s, 3H), 3.10-3.26 (m, 2H), 3.30-3.43 (m, 4H), 3.46-3.54 (m, 1H), 3.66-3.74 (m, 2H); 13C NMR (125 MHz, CDCl3): δ 28.68, 30.82, 31.25, 32.34, 36.16, 41.09, 44.88, 51.60, 55.37, 79.67, 154.43; Mass Spectrum: M+H+ 241. | CC(=O)SC1CCN(C(=O)OC(C)(C)C)C1 | null | CC(O)=S | CC(C)(C)OC(=O)N1CCC(OS(C)(=O)=O)C1 | null | C(=O)([O-])[O-].[K+].[K+].[C:7]([OH:10])(=[S:9])[CH3:8].CS(O[CH:16]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17]1)(=O)=O>CO.CN(C=O)C.O>[C:7]([S:9][CH:20]1[CH2:16][CH2:17][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:19]1)(=[O:10])[CH3:8] | 0.17 | O | CO | CN(C)C=O | 60 | null | 24.2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
206,585 | O=C([O-])O | O=S(=O)(O)O | [Na+] | null | ord_dataset-dd1de64954674e17b4b690cac09dc67b | 1990-01-01T00:04:00 | true | A solution of (S)-2-(4-chlorophenyl)-α-methyl-3H-imidazo[4,5-b]pyridine-3-acetic acid (3.0 g, 0.00995 mole) and concentrated sulfuric acid (4 drops) in ethylene glycol (50 ml) was refluxed under nitrogen for three hours, and then poured into a saturated sodium bicarbonate solution (200 ml). Water (50 ml) was added and the product was extracted into two portions of ethyl acetate. The combined organic layers were washed twice with water and once with a saturated sodium chloride solution, dried over magnesium sulfate, treated with charcoal and filtered. Evaporation of the solvents under reduced pressure gave 1.9 g (56% yield) of solid which was dissolved in hot isopropyl ether (with a little isopropyl alcohol added). The solution was stirred and cooled to room temperature to precipitate a solid. The mixture was cooled in the freezer, the solid was collected by filtration, rinsed with isopropyl ether and dried under high vacuum at room temperature overnight to give 1.44 g of title compound, mp 112°-113.5° C. | C[C@@H](C(=O)OCCO)n1c(-c2ccc(Cl)cc2)nc2cccnc21 | null | C[C@@H](C(=O)O)n1c(-c2ccc(Cl)cc2)nc2cccnc21 | OCCO | null | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([C@@H:17]([CH3:21])[C:18]([OH:20])=[O:19])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].O.[CH2:28](O)[CH2:29][OH:30]>S(=O)(=O)(O)O>[OH:30][CH2:29][CH2:28][O:19][C:18](=[O:20])[C@H:17]([CH3:21])[N:16]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:10]2[N:9]=[C:8]1[C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1 | null | O | null | null | null | null | 56 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,232,545 | Cc1cc(NC(=O)c2ccc(Cl)nc2)ccc1I | null | null | null | ord_dataset-e96f5a2842f14e5380461c234100f05a | 2012-01-01T00:12:00 | true | N-(4-tert-Butyl-pyrimidin-2-yl)-6-chloro-nicotinamide was prepared from 4-tert-butyl-pyrimidin-2-ylamine (prepared as described in J. Org. Chem. 1977, 221) and 6-chloronicotinoyl chloride following a procedure similar to the one described in the synthesis of 6-chloro-N-(4-iodo-3-methyl-phenyl)-nicotinamide, above. The product was isolated after silica gel purification with 20-40% EtOAc in hexanes gradient followed by suspension in hexanes and filtration. HRMS m/z calcd for C14H15N4OCl [M+H]+: 291.1007. Found: 291.1007. | CC(C)(C)c1ccnc(NC(=O)c2ccc(Cl)nc2)n1 | null | O=C(Cl)c1ccc(Cl)nc1 | CC(C)(C)c1ccnc(N)n1 | null | [C:1]([C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH2:11])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][N:14]=1.ClC1C=CC(C(NC2C=CC(I)=C(C)C=2)=O)=CN=1>>[C:1]([C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH:11][C:17](=[O:18])[C:16]2[CH:20]=[CH:21][C:13]([Cl:12])=[N:14][CH:15]=2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,075,554 | null | null | null | null | ord_dataset-afd812677c134591a99f46ce28de2524 | 2011-01-01T00:08:00 | true | In analogy to the procedure described for the preparation of the Building Block AU, the reaction of the 3-bromo-N-methoxy-N-methyl-5-(2,2,2-trifluoro-ethoxy)-benzamide and 4-bromo-1-methoxy-2-methyl-benzene, beforehand transformed to the Grignard reagent, yielded the title compound as a white solid (yield: 75% of theory). Mass (calculated) C17H14BrF3O3 [402]; (found) [M]+=403, 405. | COc1ccc(C(=O)c2cc(Br)cc(OCC(F)(F)F)c2)cc1C | null | CON(C)C(=O)c1cc(Br)cc(OCC(F)(F)F)c1 | COc1ccc(Br)cc1C | null | [Br:1][C:2]1[CH:3]=[C:4]([CH:11]=[C:12]([O:14][CH2:15][C:16]([F:19])([F:18])[F:17])[CH:13]=1)[C:5](N(OC)C)=[O:6].Br[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([CH3:29])[CH:22]=1>>[Br:1][C:2]1[CH:3]=[C:4]([C:5]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([CH3:29])[CH:22]=2)=[O:6])[CH:11]=[C:12]([O:14][CH2:15][C:16]([F:17])([F:18])[F:19])[CH:13]=1 | null | null | null | null | null | 75 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,681,720 | O=[Ru](=O)(=O)[O-] | CCC[N+](CCC)(CCC)CCC | C[N+]1([O-])CCOCC1 | null | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | 2016-01-01T00:01:00 | true | To a solution of N-(1-(4-(hydroxymethyl)phenyl)piperidin-4-yl)benzamide (1.1 g, 3.5 mmol) in CH2Cl2 (250 mL) was added TPAP (0.123 g, 0.35 mmol) and NMO (0.623 g, 5.3 mmol). After 1 hour, the mixture was filtered through Celite, concentrated, and purified by silica gel chromatography, eluting with 30% ethyl acetate/hexanes to 100% ethyl acetate, to afford N-(1-(4-formylphenyl)piperidin-4-yl)benzamide as a white solid (0.350 g, 32%). | O=Cc1ccc(N2CCC(NC(=O)c3ccccc3)CC2)cc1 | null | O=C(NC1CCN(c2ccc(CO)cc2)CC1)c1ccccc1 | null | null | [OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([NH:15][C:16](=[O:23])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.C[N+]1([O-])CCOCC1>C(Cl)Cl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[CH:2]([C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:10][CH2:11][CH:12]([NH:15][C:16](=[O:23])[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:13][CH2:14]2)=[CH:7][CH:8]=1)=[O:1] | 1 | ClCCl | null | null | null | 32.4 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
880,371 | Cl | [Li+] | [OH-] | null | ord_dataset-3592bd645cd143ee8274cd0d834ae581 | 2009-01-01T00:05:00 | true | 0.57 g (13.6 mmol) of lithium hydroxide monohydrate and 70 cm3 of water are added at a temperature in the region of 20° C. to 1.45 g (4.53 mmol) of 6-fluoro-3-methoxycarbonyl-1-(quinol-4-yl)-1H-indole dissolved in 70 cm3 of tetrahydrofuran. After stirring at the reflux point of the solvent for 16 hours, the reaction mixture is concentrated under reduced pressure (2.7 kPa) to give a residue which is taken up with 13.6 cm3 of N hydrochloric acid. After filtering off and drying the solid residue at atmospheric pressure at 60° C., 1.35 g of 3-carboxy-6-fluoro-1-(quinol-4-yl)-1H-indole are obtained in the form of a yellow solid melting at 190° C. | O=C(O)c1cn(-c2ccnc3ccccc23)c2cc(F)ccc12 | null | COC(=O)c1cn(-c2ccnc3ccccc23)c2cc(F)ccc12 | null | null | O.[OH-].[Li+].O.[F:5][C:6]1[CH:14]=[C:13]2[C:9]([C:10]([C:25]([O:27]C)=[O:26])=[CH:11][N:12]2[C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=[CH:17][CH:16]=2)=[CH:8][CH:7]=1.Cl>O1CCCC1>[C:25]([C:10]1[C:9]2[C:13](=[CH:14][C:6]([F:5])=[CH:7][CH:8]=2)[N:12]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=[CH:17][CH:16]=2)[CH:11]=1)([OH:27])=[O:26] | 16 | C1CCOC1 | O | null | null | 97.3 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,406,053 | O=C([O-])[O-] | [K+] | null | null | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | 2014-01-01T00:03:00 | true | 528 mg of 2,6-dichloroisonicotinaldehyde (this compound was prepared by the method described in J. Chem. Soc., Chem. Commun., 1998, 1567-1568) was dissolved in 10 ml of methanol, and 586 mg of p-toluenesulfonyl methyl isocyanide and 415 mg of potassium carbonate ware added, and the mixture was stirred at 50° C. for 30 minutes. The reaction solution was concentrated, and then diluted with ethyl acetate, and the organic layer was washed with a saturated aqueous solution of sodium bicarbonate and brine, and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 630 mg of the objective compound as white powder. | Clc1cc(-c2cnco2)cc(Cl)n1 | null | O=Cc1cc(Cl)nc(Cl)c1 | [C-]#[N+]CS(=O)(=O)c1ccc(C)cc1 | null | [Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:10])[N:9]=1)[CH:5]=[O:6].C1(C)C=CC(S([CH2:20][N+:21]#[C-:22])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[O:6][CH:22]=[N:21][CH:20]=2)[CH:7]=[C:8]([Cl:10])[N:9]=1 | 0.5 | CO | null | null | 50 | 97.7 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,456,533 | [Na+] | [OH-] | null | null | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | 2014-01-01T00:07:00 | true | To a solution of ethyl 6-chloro-7-(4-(6-(2-chloro-4-(trifluoromethyl)phenyl)pyridazin-3-ylcarbamoyl)phenoxy)chroman-4-carboxylate (0.034 g, 0.054 mmol) in 3:1 THF/EtOH (1 ml) was added 1M sodium hydroxide (0.22 ml, 0.22 mmol), and the reaction was stirred at ambient temperature for 16 hours. The reaction was concentrated to dryness, taken up in water, and acidified with 1M hydrochloric acid. The reaction was extracted twice with EtOAc, and the combined organic layers were washed with saturated sodium chloride, dried over anhydrous sodium sulfate, filtered, and concentrated to yield the desired compound (0.030 g, 0.050 mmol, 92% yield). | O=C(Nc1ccc(-c2ccc(C(F)(F)F)cc2Cl)nn1)c1ccc(Oc2cc3c(cc2Cl)C(C(=O)O)CCO3)cc1 | null | CCOC(=O)C1CCOc2cc(Oc3ccc(C(=O)Nc4ccc(-c5ccc(C(F)(F)F)cc5Cl)nn4)cc3)c(Cl)cc21 | null | null | [Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:38])[NH:20][C:21]3[N:22]=[N:23][C:24]([C:27]4[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][C:28]=4[Cl:37])=[CH:25][CH:26]=3)=[CH:15][CH:14]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:39]([O:41]CC)=[O:40].[OH-].[Na+]>C1COCC1.CCO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:38])[NH:20][C:21]3[N:22]=[N:23][C:24]([C:27]4[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:34])[F:35])=[CH:29][C:28]=4[Cl:37])=[CH:25][CH:26]=3)=[CH:15][CH:14]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:39]([OH:41])=[O:40] | 16 | CCO | C1CCOC1 | null | 25 | 92.6 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
992,735 | [Na+] | [OH-] | null | null | ord_dataset-b6d8835b0c934476a36e6149e7597487 | 2010-01-01T00:09:00 | true | Water (1 mL) was added in one portion to a stirred solution of benzyl [2-chloro-4-(1,4-dioxaspiro[4.5]dec-8-yl)phenyl]carbamate (2.60 g, 6.47 mmol) in TFA (20 mL) and the reaction mixture was stirred at room temperature for 2 h. The mixture was cooled to 10° C. and a 2N aqueous solution of sodium hydroxide was added until the pH of the mixture was 10. Ethyl acetate (50 mL) was added and the layers were separated and the aqueous layer was extracted with ethyl acetate (50 mL). The combined organic layers were washed with H2O and brine, dried (MgSO4) and concentrated in vacuo to leave the title compound (2.3 g, 99%) as a solid; 1H NMR δ 1.82-1.99 (2H, m), 2.17-2.28 (2H, m), 2.45-2.57 (4H, m), 2.94-3.07 (1H, m), 5.24 (2H, s), 7.17 (1H, dd), 7.25 (1H, d), 7.32-7.5 (5H, m), 8.13 (1H, d); MS m/e (M−H)− 356. | O=C1CCC(c2ccc(NC(=O)OCc3ccccc3)c(Cl)c2)CC1 | null | O=C(Nc1ccc(C2CCC3(CC2)OCCO3)cc1Cl)OCc1ccccc1 | null | null | O.[Cl:2][C:3]1[CH:8]=[C:7]([CH:9]2[CH2:18][CH2:17][C:12]3(OCC[O:13]3)[CH2:11][CH2:10]2)[CH:6]=[CH:5][C:4]=1[NH:19][C:20](=[O:29])[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[OH-].[Na+].C(OCC)(=O)C>C(O)(C(F)(F)F)=O>[Cl:2][C:3]1[CH:8]=[C:7]([CH:9]2[CH2:18][CH2:17][C:12](=[O:13])[CH2:11][CH2:10]2)[CH:6]=[CH:5][C:4]=1[NH:19][C:20](=[O:29])[O:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1 | 2 | CCOC(C)=O | O=C(O)C(F)(F)F | O | 25 | 99.3 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,514,297 | OBO | null | null | null | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | 2014-01-01T00:12:00 | true | 2-(thiophen-3-yl)nicotinaldehyde was prepared using the general boronic acid coupling procedure for 2-bromonicotinaldehyde and thiophen-3-ylboronic acid (60 mg, 101.8 mg theoretical, 58.9%). LC-MS m/z 190.2 (M+1). | O=Cc1cccnc1-c1ccsc1 | null | O=Cc1cccnc1Br | OB(O)c1ccsc1 | null | B(O)O.Br[C:5]1[N:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH:7]=[O:8].[S:13]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14]1>>[S:13]1[CH:17]=[CH:16][C:15]([C:5]2[N:12]=[CH:11][CH:10]=[CH:9][C:6]=2[CH:7]=[O:8])=[CH:14]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 |
422,604 | O=C([O-])[O-] | [K+] | null | null | ord_dataset-1a231de00bfe4443b547e1f03885ed41 | 1999-01-01T00:01:00 | true | A solution of 2-hydroxydibenzofuran (2.0 grams) was treated with allyl bromide (1.2 mL) and potassium carbonate (1.5 grams). The mixture was stirred over night at 60°. The reaction was partitioned between methylene chloride and water. The organic was washed once with water and dried over sodium sulfate. The organic layer was filtered and concentrated to an oil which was chromatographed over silica gel to afford the title compound. | CC=COc1ccc2oc3ccccc3c2c1 | null | Oc1ccc2oc3ccccc3c2c1 | C=CCBr | null | [OH:1][C:2]1[CH:14]=[CH:13][C:5]2[O:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:4]=2[CH:3]=1.[CH2:15](Br)[CH:16]=[CH2:17].C(=O)([O-])[O-].[K+].[K+]>>[CH:15]([O:1][C:2]1[CH:14]=[CH:13][C:5]2[O:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:4]=2[CH:3]=1)=[CH:16][CH3:17] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,045,551 | [Li+] | [OH-] | null | null | ord_dataset-dd320ded4b3f4764af39de99491533f7 | 2011-01-01T00:04:00 | true | To ethyl 2-oxo-2,3-dihydrobenzo[d]oxazole-6-carboxylate in THF (20 mL) was added LiOH (2 g in 10 mL water). The mixture was stirred at room temperature for 20 hours. The solvent was evaporated. The residue was taken up in water and acidified with 5 N HCl to pH=5. The solid was recovered by filtration, washing with water, to provide the pure product as a tan solid (1.44 g, 80%). LCMS (API-ES) m/z: 180 (M+H+). | O=C(O)c1ccc2[nH]c(=O)oc2c1 | null | CCOC(=O)c1ccc2[nH]c(=O)oc2c1 | null | null | [O:1]=[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]([O:13]CC)=[O:12])=[CH:10][C:4]=2[O:3]1.[Li+].[OH-]>C1COCC1>[O:1]=[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]([OH:13])=[O:12])=[CH:10][C:4]=2[O:3]1 | 20 | C1CCOC1 | null | null | 25 | null | 80 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
753,184 | null | null | null | null | ord_dataset-844a22e1fcab44a5b59c5e2922b2855a | 2007-01-01T00:01:00 | true | Utilising the procedure described in example 1b but employing 3-[(aminoiminomethyl)amino]-benzoic acid ethyl ester mononitrate in lieu of 3-[(aminoiminomethyl)amino]-4-methyl-benzoic acid ethyl ester mononitrate, afforded the title compound as a crystalline solid, m.p. 197–199° C. | CCOC(=O)c1cccc(Nc2nccc(-c3cccnc3)n2)c1 | null | O=[N+]([O-])O | CCOC(=O)c1ccc(C)c(NC=NN)c1 | CCOC(=O)c1cccc(NC=NN)c1 | [N+]([O-])(O)=O.[CH2:5]([O:7][C:8](=[O:19])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][CH:16]=[N:17]N)[CH:10]=1)[CH3:6].[N+:20]([O-])(O)=O.C(OC(=O)[C:28]1[CH:33]=[CH:32][C:31]([CH3:34])=[C:30]([NH:35][CH:36]=NN)[CH:29]=1)C>>[CH2:5]([O:7][C:8](=[O:19])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][C:16]2[N:20]=[C:32]([C:33]3[CH:36]=[N:35][CH:30]=[CH:29][CH:28]=3)[CH:31]=[CH:34][N:17]=2)[CH:10]=1)[CH3:6] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,589,517 | null | null | null | null | ord_dataset-e8c6a25568b64529b960953990e6921f | 2015-01-01T00:06:00 | true | To a solution of (S)—N-(1-hydroxypropan-2-yl)-2-nitrobenzenesulfonamide (6.20 kg, 23.8 mol) in methylene chloride (32 L) was added 4-methylmorpholine (3.13 kg, 30.9 mol) at an internal temperature of 10° C. or below. The resulting reaction mixture was cooled to 0° C., and added a solution of methanesulfonyl chloride (3.27 kg, 28.5 mol) in methylene chloride (2 L) at an internal temperature of −5° C. to 0° C. Subsequently, the reaction mixture was stirred at room temperature for 20 hours. After confirming the disappearance of the starting materials by TLC, purified water was added to the reaction mixture. The resulting organic layer was partitioned, washed with saturated brine, dried over magnesium sulfate, and filtered. The filtrate was then concentrated under reduced pressure to give the target product as a yellow solid (7.30 kg, yield 90.70). | C[C@@H](COS(C)(=O)=O)NS(=O)(=O)c1ccccc1[N+](=O)[O-] | null | CS(=O)(=O)Cl | C[C@@H](CO)NS(=O)(=O)c1ccccc1[N+](=O)[O-] | null | [OH:1][CH2:2][C@@H:3]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7])[CH3:4].CN1CCOCC1.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>C(Cl)Cl>[CH3:25][S:26]([O:1][CH2:2][C@@H:3]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:7])=[O:8])[CH3:4])(=[O:28])=[O:27] | 20 | ClCCl | CN1CCOCC1 | null | 0 | 90.7 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
822,345 | [Pd] | null | null | null | ord_dataset-ec58fad8331a42c5a67ad75aac6713b4 | 2008-01-01T00:05:00 | true | To a solution of benzyl 1-[2-[4-(5-methylpiridin-2-yl-amino)piperidin-1-yl]ethyl]cyclohexanecarboxylate (160 mg, 0.37 mmol) in ethanol (16 mL) was added 10% palladium carbon (80 mg) at room temperature. The mixture was stirred at room temperature under hydrogen atmosphere for 24 hours. Acetic acid was added to the mixture, and it was filtered with Celite and concentrated under reduced pressure. Methanol and diethyl ether were added to the residue, and the solution was stirred under ice cooling for 1 hour. The crystals were recovered by filtration to give the title compound (100 mg). | Cc1ccc(NC2CCN(CCC3(C(=O)O)CCCCC3)CC2)nc1 | null | Cc1ccc(NC2CCN(CCC3(C(=O)OCc4ccccc4)CCCCC3)CC2)nc1 | null | null | [CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][C:17]3([C:23]([O:25]CC4C=CC=CC=4)=[O:24])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[CH2:11][CH2:10]2)=[N:6][CH:7]=1.C(O)(=O)C>C(O)C.[C].[Pd]>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][C:17]3([C:23]([OH:25])=[O:24])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[CH2:11][CH2:10]2)=[N:6][CH:7]=1 | 24 | CC(=O)O | CCO | null | 25 | 78.2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
292,536 | [Na+] | [OH-] | null | null | ord_dataset-6c3ec086c8c9475e8d31a44641b49e02 | 1994-01-01T00:06:00 | true | A solution of 0.56 g (1.11 mol) of N-(2-methoxy-2-oxoethyl)-N-[3-(octadecyloxy)phenyl]glycine methyl ester and 4.4 ml (4.4 mmol) of 1N NaOH in 50 ml of methanol was stirred at reflux under argon atmosphere for 75 minutes. After standing at room temperature for 17 hours the precipitate was removed by filtration. The solid was suspended in 100 ml of 1N HCl and extracted with ethyl acetate. The dried extract was concentrated at reduced pressure and the resultant solid was recrystallized from methanol-water to give 0.31 g (60% yield, mp 135°-138°) of N-(carboxymethyl)-N-[3-(octadecyloxy)phenyl]glycine. | CCCCCCCCCCCCCCCCCCOc1cccc(N(CC(=O)O)CC(=O)O)c1 | null | CCCCCCCCCCCCCCCCCCOc1cccc(N(CC(=O)OC)CC(=O)OC)c1 | null | null | C[O:2][C:3](=[O:36])[CH2:4][N:5]([CH2:31][C:32]([O:34]C)=[O:33])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:7]=1.[OH-].[Na+]>CO>[C:3]([CH2:4][N:5]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:7]=1)[CH2:31][C:32]([OH:34])=[O:33])([OH:36])=[O:2] | 17 | CO | null | null | null | 0.1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,512,598 | [Zn] | null | null | null | ord_dataset-1a1aa5d1c3224edca0aec6e3398da985 | 2014-01-01T00:11:00 | true | Zinc dust (9.3 g, 142 mmol) was added to a stirred solution of N-[5-(4-fluoro-phenyl)-3-nitro-pyridin-2-yl]-benzene-1,3-diamine (2.3 g, 7.1 mmol) in AcOH (35 ml) at RT. After the exotherm had subsided the reaction was stirred and heated at 60° C. for 3 hours. The mixture was allowed to cool to RT then filtered through Celite—washing with AcOH (˜150 ml). The filtrate was evaporated and the residue was azeotroped with toluene (×2). The residue was taken up in trimethylorthoformate (50 ml) and then stirred and heated at reflux under N2 for 1 hour. After cooling to RT, the volatiles were removed in vacuo. The residue was taken up in EtOH (100 ml). c. HCl (4 ml) was added and the mixture was heated at reflux for 2 hours. After cooling, the mixture was concentrated to ˜4 ml and basified with saturated aqueous NaHCO3. The aqueous mixture was extracted with CH2Cl2 (×3). The combined extracts were dried (MgSO4), filtered and evaporated. The residue was purified by chromatography on silica (40→100% EtOAc/petrol) to give the title compound (0.86 g). | Nc1cccc(-n2cnc3cc(-c4ccc(F)cc4)cnc32)c1 | null | CC(=O)O | Nc1cccc(Nc2ncc(-c3ccc(F)cc3)cc2[N+](=O)[O-])c1 | null | [F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([N+:22]([O-])=O)[C:11]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([NH2:21])[CH:16]=3)=[N:12][CH:13]=2)=[CH:4][CH:3]=1.[CH3:25]C(O)=O>[Zn]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[N:22]=[CH:25][N:14]([C:15]4[CH:16]=[C:17]([NH2:21])[CH:18]=[CH:19][CH:20]=4)[C:11]3=[N:12][CH:13]=2)=[CH:4][CH:3]=1 | null | null | null | null | 60 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
395,596 | [Na+] | [OH-] | null | null | ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | 1998-01-01T00:03:00 | true | To a stirred solution of sodium hydroxide (0.35 g, 8.8 mM) in methanol (31 mL) was added 5-iodo-2H-3,1-benzoxazine-2,4(1H)-dione (18.5 g, 64.0 mM). The mixture was heated at 60° C. for 1.5 hr. An additional quantitiy of sodium hydroxide (0.10 g, 2.5 mM) was added to the reaction mixture and stirring at 60° C. was continued for an additonal 1 hr. After cooling to room temperature, the reaction mixture was concentrated and the residue was taken up in ethyl acetate. The ethyl acetate was washed successively with water, brine, dilute aqueous sodium hydroxide, and water. After drying over MgSO4, the ethyl acetate was filtered and concentrated to leave (13.9 g, 78.4%) of the title ester as a brown oil; MS(CI): 278 (M+H). | COC(=O)c1c(N)cccc1I | null | O=c1[nH]c2cccc(I)c2c(=O)o1 | null | null | [OH-].[Na+].[I:3][C:4]1[C:9]2[C:10](=[O:15])[O:11][C:12](=O)[NH:13][C:8]=2[CH:7]=[CH:6][CH:5]=1>CO.[OH-].[Na+]>[NH2:13][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]([I:3])[C:9]=1[C:10]([O:11][CH3:12])=[O:15] | 1 | CO | null | null | 60 | 78.4 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
504,176 | Cl | null | null | null | ord_dataset-d673d02cdac14dba9ff59f12845a4f37 | 2001-01-01T00:05:00 | true | A solution of 0.51 g of (E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2′-isobutyl-4-methyl-2′-(2-ureidoacetyl)valerohydrazide dissolved in 5 ml of 4M hydrogen chloride in dioxan was stirred for 2 hours at room temperature and diluted with diethyl ether. The solid was filtered off, washed with diethyl ether and dried to give 0.36 g of (E)-2(R)-[1(S)-(hydroxycarbamoyl)-4-phenyl-3-butenyl]-2′-isobutyl-4-methyl-2′-(2-ureidoacetyl)valerohydrazide in the form of a white solid. | CC(C)C[C@@H](C(=O)NN(CC(C)C)C(=O)CNC(N)=O)[C@H](C/C=C/c1ccccc1)C(=O)NO | null | CC(C)C[C@@H](C(=O)NN(CC(C)C)C(=O)CNC(N)=O)[C@H](C/C=C/c1ccccc1)C(=O)NOC1CCCCO1 | null | null | O1CCCCC1[O:7][NH:8][C:9]([C@H:11]([C@@H:21]([CH2:37][CH:38]([CH3:40])[CH3:39])[C:22]([NH:24][N:25]([CH2:33][CH:34]([CH3:36])[CH3:35])[C:26](=[O:32])[CH2:27][NH:28][C:29]([NH2:31])=[O:30])=[O:23])[CH2:12]/[CH:13]=[CH:14]/[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:10]>Cl.O1CCOCC1.C(OCC)C>[OH:7][NH:8][C:9]([C@H:11]([C@@H:21]([CH2:37][CH:38]([CH3:40])[CH3:39])[C:22]([NH:24][N:25]([CH2:33][CH:34]([CH3:35])[CH3:36])[C:26](=[O:32])[CH2:27][NH:28][C:29]([NH2:31])=[O:30])=[O:23])[CH2:12]/[CH:13]=[CH:14]/[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:10] | 2 | CCOCC | C1COCCO1 | null | 25 | null | 83.1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
149,725 | N | [Cl-] | [NH4+] | null | ord_dataset-f222e615b1f74f0fabef9cd9b98516b7 | 1986-01-01T00:10:00 | true | A mixture of liquid NH3 (400 mL) and catalytic Fe(NO3)3 was stirred under N2 at -50° C. A small portion of Na metal (from a total amount of 20 g., 0.87 mole) was added. Air was bubbled through the reaction mixture briefly until a black precipitate appeared. The remaining Na was added portionwise. 3-(6-bromo-2,3-dimethoxyphenyl)-propionitrile (31.1 g, 0.115 mole) was added over 70 minutes as the reaction mixture was stirred at slow reflux. When the addition was complete, the reaction mixture was stirred at reflux for 1/2 hr, then was cooled to -55° C. as NH4Cl (35.2 g, 0.66 mole) was added slowly. NH3 was allowed to evaporate overnight. Water was added cautiously with stirring. The solid was filtered, washed with water, dried (in-vacuo) to yield 21.0 g gray powder, (97%); M+ 189. | COc1ccc2c(c1OC)CC2C#N | null | COc1ccc(Br)c(CCC#N)c1OC | null | null | Br[C:2]1[C:7]([CH2:8][CH2:9][C:10]#[N:11])=[C:6]([O:12][CH3:13])[C:5]([O:14][CH3:15])=[CH:4][CH:3]=1.[NH4+].[Cl-]>N>[CH3:13][O:12][C:6]1[C:7]2[CH2:8][CH:9]([C:10]#[N:11])[C:2]=2[CH:3]=[CH:4][C:5]=1[O:14][CH3:15] | null | null | null | null | -50 | null | 96.5 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
374,844 | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | null | null | null | ord_dataset-ee5599340390470d8e5b5ac1feddf9d6 | 1997-01-01T00:08:00 | true | 4.6 g of ethyl 5-bromo-1-(2,4-difluorophenyl)-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate, 4.5 g of tributylvinylstannane and 0.46 g of tetrakis(triphenylphosphine)palladium(0) are refluxed for 10 hours in 40 ml of absolute toluene under a nitrogen atmosphere. The product is filtered off with suction at room temperature, washed with water and dried. 2.7 g of the title compound are obtained (66% of theory). | C=Cc1c(F)c(F)c(F)c2c1c(=O)c(C(=O)OCC)cn2-c1ccc(F)cc1F | null | CCCCC([SnH3])=C(CCCC)CCCC | CCOC(=O)c1cn(-c2ccc(F)cc2F)c2c(F)c(F)c(F)c(Br)c2c1=O | null | Br[C:2]1[C:11]([F:12])=[C:10]([F:13])[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:28])[C:5]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:6][N:7]2[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=1[F:22].[CH2:29](C([SnH3])=C(CCCC)CCCC)[CH2:30]CC>C1(C)C=CC=CC=1.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>[F:22][C:16]1[CH:17]=[C:18]([F:21])[CH:19]=[CH:20][C:15]=1[N:7]1[C:8]2[C:3](=[C:2]([CH:29]=[CH2:30])[C:11]([F:12])=[C:10]([F:13])[C:9]=2[F:14])[C:4](=[O:28])[C:5]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:6]1 | null | Cc1ccccc1 | null | null | null | null | 66.3 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,110,303 | [BH3-]C#N | [Na+] | null | null | ord_dataset-375a420ee9b042918ddca20f02df37d3 | 2011-01-01T00:11:00 | true | To a 25° C. solution of 4-(5-aminomethyl-naphthalene-1-sulfonylamino)-piperidine-1-carboxylic acid ethyl ester 55 (62 mg, 0.159 mmol) in MeOH (4 mL) was added 4-chloro-benzaldehyde (45 mg, 0.318 mmol) and sodium cyanoborohydride (50 mg, 0.795 mmol). After stirring for 2 h at 25° C., the solution was concentrated in vacuo and the resultant crude material was purified by reverse phase HPLC to provide the title compound (H-45) as its formate salt. 1H NMR (300 MHz, MeOD) δ 8.78 (d, 1H), 8.38 (s, 1H), 8.33 (m, 2H), 7.70 (m, 3H), 7.45 (m, 4H), 4.57 (s, 2H), 4.20 (s, 2H), 4.05 (q, 2H), 3.75 (d, 2H), 3.20 (m, 1H), 2.75 (m, 2H), 1.50 (m, 2H), 1.25 (m, 2H), 1.17 (t, 3H); LC/MS m/z 516 (M+H)+. | CCOC(=O)N1CCC(NS(=O)(=O)c2cccc3c(CNCc4ccc(Cl)cc4)cccc23)CC1 | O=C[O-] | O=Cc1ccc(Cl)cc1 | CCOC(=O)N1CCC(NS(=O)(=O)c2cccc3c(CN)cccc23)CC1 | null | [CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([NH:12][S:13]([C:16]2[C:25]3[C:20](=[C:21]([CH2:26][NH2:27])[CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH2:8][CH2:7]1)=[O:5])[CH3:2].[Cl:28][C:29]1[CH:36]=[CH:35][C:32]([CH:33]=O)=[CH:31][CH:30]=1.C([BH3-])#N.[Na+]>CO>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([NH:12][S:13]([C:16]2[C:25]3[C:20](=[C:21]([CH2:26][NH:27][CH2:33][C:32]4[CH:35]=[CH:36][C:29]([Cl:28])=[CH:30][CH:31]=4)[CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)(=[O:14])=[O:15])[CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH:4]([O-:5])=[O:3] | 2 | CO | 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 |
227,554 | O=C(n1ccnc1)n1ccnc1 | null | null | null | ord_dataset-d98d003e9abb4b579746c5a361466e14 | 1991-01-01T00:05:00 | true | A solution of 6-oxo-6-(2-phenylethylamino)hexanoic acid (2.49 g) and carbonyldiimidazole (1.62 g) in dry dichloromethane (100 ml) was stirred under a nitrogen atmosphere for 2 hours at room temperature. A solution of 1,2,3,4-tetrahydro-5,6-dimethoxy-2- aminonaphthalene (2.07 g) in dichloromethane (20 ml) was added and the solution stirred at room temperature for 18 hours. The solution was washed with dilute hydrochloric acid, dilute sodium carbonate solution and water. The organic phase was separated, dried over magnesium sulfate, filtered and evaporated to leave the sub-title compound which crystallised from isopropanol as colorless flakes (3.8 g), m.p. 191°-193°. | COc1ccc2c(c1OC)CCC(NC(=O)CCCCC(=O)NCCc1ccccc1)C2 | null | O=C(O)CCCCC(=O)NCCc1ccccc1 | COc1ccc2c(c1OC)CCC(N)C2 | null | [O:1]=[C:2]([NH:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:3][CH2:4][CH2:5][CH2:6][C:7](O)=[O:8].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:31][O:32][C:33]1[C:42]([O:43][CH3:44])=[CH:41][CH:40]=[C:39]2[C:34]=1[CH2:35][CH2:36][CH:37]([NH2:45])[CH2:38]2>ClCCl>[CH3:31][O:32][C:33]1[C:42]([O:43][CH3:44])=[CH:41][CH:40]=[C:39]2[C:34]=1[CH2:35][CH2:36][CH:37]([NH:45][C:7](=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][C:2]([NH:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:1])[CH2:38]2 | 18 | 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 |
1,054,125 | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | ord_dataset-373415d3e0e54004837cf4831e67666f | 2011-01-01T00:05:00 | true | 4-[(4-Amino-3-nitrophenyl)oxy]-3-chlorobenzaldehyde (1.16 g, 5.3 mmol), ethylene glycol (5 ml) and p-toluenesulfonic acid (50 mg) in 150 mL of toluene was heated at 120 degrees centigrade with a Dean-Stark trap for 24 hours. The reaction mixture was diluted with ethyl acetate and washed twice with 1N NaOH. The organic layer was dried over MgSO4 and concentrated to give 4-{[2-chloro-4-(1,3-dioxolan-2-yl)phenyl]oxy}-2-nitroaniline. (M+1) 336.9, 2.60 min (LC/MS method B) | Nc1ccc(Oc2ccc(C3OCCO3)cc2Cl)cc1[N+](=O)[O-] | null | OCCO | Nc1ccc(Oc2ccc(C=O)cc2Cl)cc1[N+](=O)[O-] | null | [NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][C:10]=2[Cl:17])=[CH:4][C:3]=1[N+:18]([O-:20])=[O:19].[CH2:21](O)[CH2:22][OH:23].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:17][C:10]1[CH:11]=[C:12]([CH:13]2[O:23][CH2:22][CH2:21][O:14]2)[CH:15]=[CH:16][C:9]=1[O:8][C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[C:3]([N+:18]([O-:20])=[O:19])[CH:4]=1 | null | CCOC(C)=O | 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 |
1,530,909 | null | null | null | null | ord_dataset-8d5c200bca27407ab9febe7598e16458 | 2015-01-01T00:01:00 | true | In a glass flask provided with a condenser, thermometer, mechanical stirrer and nitrogen inlet, —under nitrogen flow—15.0 g of 3-chloro-4-[(2-fluorobenzyl)oxy]aniline of formula (IV), 17.49 g of 4-chloro-6-iodoquinazoline of formula (VIII) (available in the market), 300 mL of Isopropanol were introduced. The reaction mixture was stirred at 70° C. for 2 hrs. Upon completing the reaction cooling was carried out at ambient temperature. The formed yellow solid was filtered washing the solid with 20 mL of cold Isopropanol. 31.9 g of product equivalent to a 98.7% molar yield were obtained. 1H-NMR spectrum according to FIG. 5. | Cl | Fc1ccccc1COc1ccc(Nc2ncnc3ccc(I)cc23)cc1Cl | Nc1ccc(OCc2ccccc2F)c(Cl)c1 | Clc1ncnc2ccc(I)cc12 | null | [Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[F:17])[NH2:5].Cl[C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([I:29])[CH:27]=2)[N:22]=[CH:21][N:20]=1>C(O)(C)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([I:29])[CH:27]=3)[N:22]=[CH:21][N:20]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[F:17] | 2 | CC(C)O | null | null | 70 | 197.4 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,129,812 | [K+] | null | null | null | ord_dataset-285df12e34cd46e993e3c8ebc3a8962a | 2012-01-01T00:01:00 | true | To a solution of 3-chloro-N-(3,4-difluoro-2-(2-fluoro-4-iodophenylamino)phenyl)-propane-1-sulfonamide (69.4 mg, 0.138 mmol) in a mixture of 8 ml 1,4-dioxane and 2 ml H2O was added KOH powder (0.674 g, 12.0 mmol) and the mixture was heated to the reflux temperature for 3 days. It was extracted using EtOAc/brine, the organic fraction was dried with Na2SO4 and the volatiles were removed. The residue was purified using flash-column chromatography (Si, DCM/MeOH 5:1, Rf=0.3). Yield: 41 mg (62%). 1H-NMR (500 MHz, MeOH [d4]): δ=7.38-7.21 (d, 1H), 7.23-7.21 (d, 1H), 7.06-7.00 (q, 1H), 6.52-6.50 (m, 1H), 6.17-6.13 (t, 1H), 3.30-3.27 (t, 2H), 2.86-2.83 (t, 2H), 2.05-2.00 (m, 2H); m/z=485 [M−1]−. | O=S(=O)(CCCO)Nc1ccc(F)c(F)c1Nc1ccc(I)cc1F | null | O=S(=O)(CCCCl)Nc1ccc(F)c(F)c1Nc1ccc(I)cc1F | [OH-] | null | Cl[CH2:2][CH2:3][CH2:4][S:5]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[C:11]([F:16])[C:10]=1[NH:17][C:18]1[CH:23]=[CH:22][C:21]([I:24])=[CH:20][C:19]=1[F:25])(=[O:7])=[O:6].[OH-:26].[K+]>O1CCOCC1.O>[F:16][C:11]1[C:10]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([I:24])=[CH:20][C:19]=2[F:25])=[C:9]([NH:8][S:5]([CH2:4][CH2:3][CH2:2][OH:26])(=[O:7])=[O:6])[CH:14]=[CH:13][C:12]=1[F:15] | null | O | 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 |
858,497 | [N-]=[N+]=NC[C@H]1CN(c2cc(F)c(N3CCS(=O)(=O)CC3)c(F)c2)C(=O)O1 | null | null | null | ord_dataset-93908aaae836460ebd48d733eccad483 | 2009-01-01T00:01:00 | true | A suspension of (5R) 3-[3,5-difluoro-4-(1,1-dioxo-4-thiomorpholinyl)phenyl]-5-(azidomethyl)-oxazolidin-2-one (Intermediate 10) (0.82 g, 2.11 mmol) and polystyrene triphenylphosphine (5.6 g, 8.5 mmol) was reacted as described for Example 9 to give the intermediate amine, (5R)-3-[4-(1,1-Dioxo-4-thiomorpholinyl)-3,5-difluorophenyl]-5-(aminomethyl)-oxazolidin-2-one (0.65 g), which was used directly for the next step. This amine (0.63 g, 1.75 mmol) was reacted with diisopropylethylamine (0.9 ml, 5.2 mmol) and α,α-dichloroacetone tosylhydrazone (0.77 g, 2.62 mmol) as described for Example 3. Chromatography on silica gel eluting with 5% methanol in dichloromethane gave the title compound (350 mg). | NC[C@@H]1CN(c2cc(F)c(N3CCS(=O)(=O)CC3)c(F)c2)C(=O)O1 | null | [N-]=[N+]=NCC1CN(c2cc(F)c(N3CCS(=O)(=O)CC3)c(F)c2)C(=O)O1 | null | null | [F:1][C:2]1[CH:3]=[C:4]([N:17]2[CH2:21][CH:20]([CH2:22][N:23]=[N+]=[N-])[O:19][C:18]2=[O:26])[CH:5]=[C:6]([F:16])[C:7]=1[N:8]1[CH2:13][CH2:12][S:11](=[O:15])(=[O:14])[CH2:10][CH2:9]1.N(C[C@@H]1OC(=O)N(C2C=C(F)C(N3CCS(=O)(=O)CC3)=C(F)C=2)C1)=[N+]=[N-]>>[O:15]=[S:11]1(=[O:14])[CH2:10][CH2:9][N:8]([C:7]2[C:6]([F:16])=[CH:5][C:4]([N:17]3[CH2:21][C@@H:20]([CH2:22][NH2:23])[O:19][C:18]3=[O:26])=[CH:3][C:2]=2[F:1])[CH2:13][CH2:12]1 | null | null | null | null | null | 85.2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
133,159 | null | null | null | null | ord_dataset-34cf5f1378de4e34844aea93a2f9a9d3 | 1985-01-01T00:08:00 | true | 2.98 g of ethyl 3-(4-chlorobenzoylamino)-3-acetylpropionate, 15 ml of dimethylformamide and 1.8 g of phosphorus oxychloride are treated in the same manner as described in Example 1. 1.98 g of ethyl 2-[2-(4-chlorophenyl)-5-methyl-4-oxazolyl]acetate are thereby obtained. Yield: 70.9%. | CCOC(=O)Cc1nc(-c2ccc(Cl)cc2)oc1C | null | CCOC(=O)CC(NC(=O)c1ccc(Cl)cc1)C(C)=O | null | null | [Cl:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([NH:8][CH:9]([C:16](=[O:18])[CH3:17])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=O)=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O>CN(C)C=O>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]2[O:18][C:16]([CH3:17])=[C:9]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:8]=2)=[CH:4][CH:3]=1 | null | CN(C)C=O | O=P(Cl)(Cl)Cl | null | null | null | 70.7 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
671,066 | null | null | null | null | ord_dataset-e90cd41afe844e49875435eb99903799 | 2005-01-01T00:05:00 | true | A mixture of N-(6-chloro-pyrazin-2-yl)-acetamide I-5a (58.6 mg, 0.34 mmol) and piperazine-1-carboxylic acid tert-butyl ester (636 mg, 3.42 mmol) in ethanol (2 mL) was stirred at reflux for 24 h. The reaction mixture was diluted with ethyl acetate (40 mL) and washed with 0.1M HCl (3×35 mL), brine, dried (Na2SO4), filtered, and evaporated to dryness. The crude residue was purified by preparative TLC using ethyl acetate as the eluant to afford the title compound I-5b (36.9 mg). | CC(=O)Nc1cncc(N2CCN(C(=O)OC(C)(C)C)CC2)n1 | null | CC(C)(C)OC(=O)N1CCNCC1 | CC(=O)Nc1cncc(Cl)n1 | null | Cl[C:2]1[N:7]=[C:6]([NH:8][C:9](=[O:11])[CH3:10])[CH:5]=[N:4][CH:3]=1.[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13]>C(O)C.C(OCC)(=O)C>[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][N:22]([C:2]2[CH:3]=[N:4][CH:5]=[C:6]([NH:8][C:9](=[O:11])[CH3:10])[N:7]=2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14] | null | CCOC(C)=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 |
394,099 | Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1 | [Cl-] | [Na+] | null | ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | 1998-01-01T00:03:00 | true | To a solution of 4-ethynylbenzonitrile (0.5 g), 2-bromo-5-nitrothiophene (0.9 g) and bis(triphenylphosphine)palladium dichloride (83 mg) in anhydrous dimethylformamide (4 ml) was added triethylamine (2.2 ml). The reaction mixture was stirred at room temperature for 3 days then ethyl acetate (200 ml) and saturated sodium chloride (200 ml) were added. The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated to dryness. The crude solid was triturated with 1:1 dichloromethane/hexane followed by diethyl ether to give 4-[(5-nitro-2-thienyl)ethynyl]benzonitrile as a yellow solid. | N#Cc1ccc(C#Cc2ccc([N+](=O)[O-])s2)cc1 | null | O=[N+]([O-])c1ccc(Br)s1 | C#Cc1ccc(C#N)cc1 | null | [C:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1)#[CH:2].Br[C:12]1[S:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=1.C(N(CC)CC)C.[Cl-].[Na+]>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.C(OCC)(=O)C>[N+:17]([C:14]1[S:13][C:12]([C:2]#[C:1][C:3]2[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=2)=[CH:16][CH:15]=1)([O-:19])=[O:18] | 72 | CCOC(C)=O | CCN(CC)CC | CN(C)C=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 |
700,440 | [Li+] | [OH-] | null | null | ord_dataset-bbd7e53f000345838ad4920a07a169ff | 2006-01-01T00:03:00 | true | To an ice cold solution of methyl N-(4-bromo-3-methylisothiazol-5-yl)-L-leucinate (11.7 g, 36.4 mmol) in methanol (300 mL) was slowly added over 10 min a 2.0 M aqueous lithium hydroxide solution (75 mL, 150 mmol). The resulting cloudy solution was stirred at room temperature for 3 hours. Most of the methanol was removed under reduced pressure and the resulting aqueous suspension was partitioned between EtOAc and water+90 ml of 10% HCl. The organic layer was washed once with water, dried over Na2SO4 and concentrated in vacuo to give N-(4-bromo-3-methylisothiazol-5-yl)-L-leucine as a white solid. | Cc1nsc(N[C@@H](CC(C)C)C(=O)O)c1Br | null | COC(=O)[C@H](CC(C)C)Nc1snc(C)c1Br | null | null | [Br:1][C:2]1[C:3]([CH3:17])=[N:4][S:5][C:6]=1[NH:7][C@H:8]([C:13]([O:15]C)=[O:14])[CH2:9][CH:10]([CH3:12])[CH3:11].[OH-].[Li+]>CO>[Br:1][C:2]1[C:3]([CH3:17])=[N:4][S:5][C:6]=1[NH:7][C@H:8]([C:13]([OH:15])=[O:14])[CH2:9][CH:10]([CH3:12])[CH3:11] | 3 | CO | 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 |
1,690,539 | [Li]O | null | null | null | ord_dataset-c1e70ad912eb438f8d34b1dc681f809a | 2016-01-01T00:02:00 | true | A mixture of 113a (80 mg, 0.115 mmol) and LiOH.H2O (24 mg, 0.573 mmol) in THF/i-PrOH/water (3.0 mL/1.0 mL/1.0 mL) was stirred at rt for 6 h. The mixture was extracted with EA. The combined organic layers were dried over Na2SO4, filtered and concentrated. The residue was purified by prep-TLC (EA/MeOH=25/1) to give 113 (50 mg, 67%) as white solid. 1H NMR (300 MHz, DMSO-d6, 80° C.): δ 8.42 (s, 2H), 8.35 (s, 1H), 7.52 (t, J=8.1 Hz, 1H), 7.43 (d, J=2.4 Hz, 1H), 7.33-7.30 (m, 2H), 6.81 (d, J=8.1 Hz, 1H), 6.68-6.59 (m, 1H), 6.19 (d, J=8.1 Hz, 1H), 6.05-5.99 (m, 1H), 5.56 (m, 1H), 4.37-4.32 (m, 2H), 3.68 (t, J=5.4 Hz, 2H), 3.62 (s, 3H), 3.07 (s, 3H), 2.95-2.86 (m, 6H), 1.91-1.89 (m, 4H). ESI-LCMS: m/z=657.3 [C34H33FN6O5S+H]+ | C=CC(=O)N(C)CCOc1cccc(Nc2cc(-c3cc(F)cc(-n4ncc5c6c(sc5c4=O)CCCC6)c3CO)cn(C)c2=O)n1 | null | C=CC(=O)N(C)CCOc1cccc(Nc2cc(-c3cc(F)cc(-n4ncc5c6c(sc5c4=O)CCCC6)c3COC(C)=O)cn(C)c2=O)n1 | null | null | [F:1][C:2]1[CH:3]=[C:4]([N:37]2[C:42](=[O:43])[C:41]3[S:44][C:45]4[CH2:50][CH2:49][CH2:48][CH2:47][C:46]=4[C:40]=3[CH:39]=[N:38]2)[C:5]([CH2:32][O:33]C(=O)C)=[C:6]([C:8]2[CH:9]=[C:10]([NH:16][C:17]3[N:22]=[C:21]([O:23][CH2:24][CH2:25][N:26]([CH3:31])[C:27](=[O:30])[CH:28]=[CH2:29])[CH:20]=[CH:19][CH:18]=3)[C:11](=[O:15])[N:12]([CH3:14])[CH:13]=2)[CH:7]=1.O[Li].O>C1COCC1.CC(O)C.O>[F:1][C:2]1[CH:3]=[C:4]([N:37]2[C:42](=[O:43])[C:41]3[S:44][C:45]4[CH2:50][CH2:49][CH2:48][CH2:47][C:46]=4[C:40]=3[CH:39]=[N:38]2)[C:5]([CH2:32][OH:33])=[C:6]([C:8]2[CH:9]=[C:10]([NH:16][C:17]3[N:22]=[C:21]([O:23][CH2:24][CH2:25][N:26]([CH3:31])[C:27](=[O:30])[CH:28]=[CH2:29])[CH:20]=[CH:19][CH:18]=3)[C:11](=[O:15])[N:12]([CH3:14])[CH:13]=2)[CH:7]=1 | 6 | C1CCOC1 | CC(C)O | O | 25 | null | 66.2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,629,447 | CC(C)(C)OC(=O)N1CCC(O)CC1 | O=C([O-])[O-] | [Na+] | null | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | 2015-01-01T00:09:00 | true | To a solution consisting of 2-phenyl-5-(2H-tetrazol-5-yl)pyrimidine (25 mg, 0.111 mmol) in DMF (2.0 mL) was added tert-butyl 4-(tosyloxy)piperidine-1-carboxylate (40 mg, 0.111 mmol), synthesized from tert-butyl 4-hydroxypiperidine-1-carboxylate (PCT International Application No. WO 2007/060026), and sodium carbonate (85 mg, 0.45 mmol). The suspension was vigorously stirred for 24 hours and an additional molar equivalent of tert-butyl 4-(tosyloxy)piperidine-1-carboxylate was added and the reaction was heated for another 24 hours at 70° C. After cooling to room temperature, the crude reaction mixture was diluted with ethyl acetate, washed sequentially with 1 M sodium carbonate, 5% citric acid, and brine. After solvent evaporation, the remaining crude solid was dissolved in a minimal amount of dichloromethane and purified by flash silica column chromatography. Elution through a 40-g Analogix® flash silica cartridge with 100% dichloromethane to 2% methanol in dichloromethane provided the title compound as an off-white solid. The solid was further purified by triturating with methanol to afford the title compound as a white solid (15 mg, 33% yield); Rf 0.37 with 95:2 v/v dichloromethane-methanol; melting point 178-180° C.; 1H-NMR (400 MHz; CDCl3) δ 9.47 (s, 2H), 8.52-8.49 (m, 2H), 7.52-7.50 (m, 3H), 4.96-4.95 (m, 2H), 4.23 (bs, 2H), 3.10-2.97 (m, 2H), 2.30-2.21 (m, 4H), 1.48 (s, 9H); MS (ESI+) m/z 408.2 (M+1). | CC(C)(C)OC(=O)N1CCC(n2nnc(-c3cnc(-c4ccccc4)nc3)n2)CC1 | null | Cc1ccc(S(=O)(=O)OC2CCN(C(=O)OC(C)(C)C)CC2)cc1 | c1ccc(-c2ncc(-c3nn[nH]n3)cn2)cc1 | null | [C:1]1([C:7]2[N:12]=[CH:11][C:10]([C:13]3[N:14]=[N:15][NH:16][N:17]=3)=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(O[CH:29]1[CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31][CH2:30]1)(C1C=CC(C)=CC=1)(=O)=O.OC1CCN(C(OC(C)(C)C)=O)CC1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.C(OCC)(=O)C>[C:1]1([C:7]2[N:12]=[CH:11][C:10]([C:13]3[N:14]=[N:15][N:16]([CH:29]4[CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31][CH2:30]4)[N:17]=3)=[CH:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1 | 24 | CN(C)C=O | CCOC(C)=O | null | 70 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
213,280 | O=C([O-])[O-] | [K+] | null | null | ord_dataset-b67d30cd146f49dcbf24faee022f1a09 | 1990-01-01T00:08:00 | true | A suspension of 10.2 g of 7-chloro-2,3-dihydro-1,2-benzisothiazole-1,1-dioxide, 8.3 g of potassium carbonate and 7.7 ml of 1-iodopentane was refluxed in 50 ml of ethanol for 28 hours, cooled, concentrated and added to 200 ml of water. The mixture was extracted with n-BuCl, the extract washed with water and brine, dried over MgSO4 and concentrated to give 13.3 g of an amber oil which was triturated with hexane to give 11.4 g of the title compound as a tan powder, m.p. 46°-48° C. | CCCCCN1Cc2cccc(Cl)c2S1(=O)=O | null | O=S1(=O)NCc2cccc(Cl)c21 | CCCCCI | null | [Cl:1][C:2]1[C:10]2[S:9](=[O:12])(=[O:11])[NH:8][CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>C(O)C>[CH2:20]([N:8]1[CH2:7][C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([Cl:1])[C:10]=2[S:9]1(=[O:12])=[O:11])[CH2:21][CH2:22][CH2:23][CH3:24] | null | 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 | null |
135,432 | O=C1CCCN1 | null | null | null | ord_dataset-3007013966624a1096d71142f31cb5a3 | 1985-01-01T00:10:00 | true | Reaction of 9(R)-acetyl-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydronaphthacene-5,12-dione ([α]D20 =-87° (c=0.1, CHCl3)) (11.5 g) with pyrrolidone hydrotribromide (18.19 g) was effected in tetrahydrofuran (1380 mg) at room temperature for 40 hours. After removing insoluble matters by filtration, the solvent was distilled off under reduced pressure to give 9(R)-bromoacetyl-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydronaphthacene-5,12-dione, which was used in the next step without purification. | O=C1c2ccccc2C(=O)c2c(O)c3c(c(O)c21)CC[C@](O)(C(=O)CBr)C3 | null | CC(=O)[C@@]1(O)CCc2c(O)c3c(c(O)c2C1)C(=O)c1ccccc1C3=O | null | null | [C:1]([C@:4]1([OH:26])[CH2:21][C:20]2[C:19]([OH:22])=[C:18]3[C:9]([C:10](=[O:24])[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=4[C:17]3=[O:23])=[C:8]([OH:25])[C:7]=2[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C1CNC(=O)C1.[Br:33][Br-]Br>O1CCCC1>[Br:33][CH2:2][C:1]([C@:4]1([OH:26])[CH2:21][C:20]2[C:19]([OH:22])=[C:18]3[C:9]([C:10](=[O:24])[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=4[C:17]3=[O:23])=[C:8]([OH:25])[C:7]=2[CH2:6][CH2:5]1)=[O:3] | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,008,162 | O=C([O-])[O-] | [K+] | null | null | ord_dataset-7448b89163bf426c9d9777809ce24cec | 2010-01-01T00:11:00 | true | To a solution of 3-(3-chloro-4-isopropoxyphenyl)-5-(1,2,3,4-tetrahydroisoquinolin-5-yl)-1,2,4-oxadiazole (0.0726 g, 0.196 mmol) in DMF (1.963 ml) was added K2CO3 (0.054 g, 0.393 mmol) followed by tert-butyl bromoacetate (0.030 ml, 0.206 mmol). After about 48 h the reaction mixture was filtered, concentrated in vacuo and purified by chromatography to provide tert-butyl 2-(5-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)-3,4-dihydroisoquinolin-2(1H)-yl)acetate as a colorless oil that solidified on standing. LCMS (Table 1, Method c) Rt=3.41 min, m/z 486 (M+H)+. | CC(C)Oc1ccc(-c2noc(-c3cccc4c3CCN(CC(=O)OC(C)(C)C)C4)n2)cc1Cl | null | CC(C)(C)OC(=O)CBr | CC(C)Oc1ccc(-c2noc(-c3cccc4c3CCNC4)n2)cc1Cl | null | [Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[N:16]=[C:15]([C:17]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:18]=3[CH2:19][CH2:20][NH:21][CH2:22]4)[O:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].C([O-])([O-])=O.[K+].[K+].Br[CH2:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[N:16]=[C:15]([C:17]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:18]=3[CH2:19][CH2:20][N:21]([CH2:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:22]4)[O:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10] | null | CN(C)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 |
1,713,743 | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | null | null | null | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | 2016-01-01T00:04:00 | true | A mixture of 1-benzyl-2-bromo-5-chloro-1H-pyrrolo[3,2-b]pyridine (0.15 g, 0.47 mmol, from Example 62, Step 2) and 4-(tributylstannyl)-1-trityl-1H-imidazole (0.28 g, 0.47 mmol, Synthonix) in toluene (9.0 mL) was degassed. Tetrakis(triphenylphosphine)palladium(0) (54 mg, 0.047 mmol) was added and the reaction was stirred at 110° C. for 17 h. Solvent was removed in vacuo and the product was purified by flash chromatography, eluting with a gradient from 0-35% EtOAc in hexanes to afford product as a white solid (0.17 g, 66%). | Clc1ccc2c(cc(-c3cn(C(c4ccccc4)(c4ccccc4)c4ccccc4)cn3)n2Cc2ccccc2)n1 | null | Clc1ccc2c(cc(Br)n2Cc2ccccc2)n1 | CCCC[Sn](CCCC)(CCCC)c1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cn1 | null | [CH2:1]([N:8]1[C:16]2[C:11](=[N:12][C:13]([Cl:17])=[CH:14][CH:15]=2)[CH:10]=[C:9]1Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:24]1[N:25]=[CH:26][N:27]([C:29]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:28]=1)CCC>C1(C)C=CC=CC=1.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>[CH2:1]([N:8]1[C:16]2[C:11](=[N:12][C:13]([Cl:17])=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:24]1[N:25]=[CH:26][N:27]([C:29]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:28]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1 | 17 | Cc1ccccc1 | null | null | 110 | null | 65.6 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,297,436 | CCN=C=NCCCN(C)C | Cl | null | null | ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c | 2013-01-01T00:05:00 | true | A solution of 4.40 g (8.64 mmol) of (S)-4-benzyloxy-2-{2-[benzyloxycarbonyl-(2-carboxy-ethyl)-amino]-ethylamino}-butyric acid methyl ester; hydrochloride in 85 ml dichloromethane was treated with 1.20 (8.64 mmol) of triethylamine and at 0° C. with 1.99 g (10.37 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride. The cooling bath was allowed to come to room temperature and after 15 h the reaction was extracted with 10% aq. potassium hydrogensulfate solution/diethyl ether (3×). The organic phases were washed with 10% aq. potassium hydrogensulfate solution, 10% sodium chloride solution and dried over Na2SO4 to yield after evaporation of the solvent 3.74 g (95%) of the titled compound as light yellow oil. MS: 455.2 (MH+). | COC(=O)[C@H](CCOCc1ccccc1)N1CCN(C(=O)OCc2ccccc2)CCC1=O | null | COC(=O)[C@H](CCOCc1ccccc1)NCCN(CCC(=O)O)C(=O)OCc1ccccc1 | null | null | [CH3:1][O:2][C:3](=[O:34])[C@@H:4]([NH:15][CH2:16][CH2:17][N:18]([C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])[CH2:19][CH2:20][C:21](O)=[O:22])[CH2:5][CH2:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl.C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC>ClCCl>[CH2:27]([O:26][C:24]([N:18]1[CH2:19][CH2:20][C:21](=[O:22])[N:15]([C@H:4]([C:3]([O:2][CH3:1])=[O:34])[CH2:5][CH2:6][O:7][CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:16][CH2:17]1)=[O:25])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1 | 15 | ClCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
244,117 | null | null | null | null | ord_dataset-fa3b512e2d924b9b965301ebcba6853d | 1992-01-01T00:03:00 | true | To a stirred mixture of 5-bromo-2,4-dichloroquinazoline (2.3 g, 8.2 mmol) and triethylamine (1.5 ml, 11 mmol) in dichloromethane (100 ml) was added ethanolamine (0.64 ml, 11 mmol), and the mixture was stirred for 30 min. The solvent was evaporated and the residue treated with a mixture of water (30 ml) and ether (20 ml) giving the title compound as a crystalline precipitate which was collected by filtration and dried, m.p. 165°-67° C. | OCCNc1nc(Cl)nc2cccc(Br)c12 | null | Clc1nc(Cl)c2c(Br)cccc2n1 | NCCO | null | [Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](Cl)=[N:5][C:6]([Cl:12])=[N:7]2.C(N(CC)CC)C.[CH2:21]([CH2:23][NH2:24])[OH:22]>ClCCl>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([NH:24][CH2:23][CH2:21][OH:22])=[N:5][C:6]([Cl:12])=[N:7]2 | 0.5 | ClCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
581,706 | Cl | null | null | null | ord_dataset-60f3171f0342452f8814e7f294e2be8b | 2003-01-01T00:02:00 | true | By the reaction in the same manner as in Example 4-(iii) using 3′-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propyl][1,1′-biphenyl]-4-carbonitrile (590 mg) and pyridine hydrochloride (111 mg), the title compound (261 mg) was obtained as colorless needle crystals. | CC(C)C(O)(c1cccc(-c2ccc(C#N)cc2)c1)c1c[nH]cn1 | null | CC(C)C(O)(c1cccc(-c2ccc(C#N)cc2)c1)c1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cn1 | null | null | [OH:1][C:2]([C:30]1[CH:31]=[C:32]([C:36]2[CH:41]=[CH:40][C:39]([C:42]#[N:43])=[CH:38][CH:37]=2)[CH:33]=[CH:34][CH:35]=1)([C:6]1[N:7]=[CH:8][N:9](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:10]=1)[CH:3]([CH3:5])[CH3:4].Cl.N1C=CC=CC=1>>[OH:1][C:2]([C:30]1[CH:31]=[C:32]([C:36]2[CH:37]=[CH:38][C:39]([C:42]#[N:43])=[CH:40][CH:41]=2)[CH:33]=[CH:34][CH:35]=1)([C:6]1[N:7]=[CH:8][NH:9][CH:10]=1)[CH:3]([CH3:4])[CH3:5] | null | c1ccncc1 | null | null | null | null | 78 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
581,305 | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | ord_dataset-60f3171f0342452f8814e7f294e2be8b | 2003-01-01T00:02:00 | true | The process is performed according to the operating conditions described in 1.8, starting with 300 mg (0.62 mmol) of 3-[hydroxy[2-phenyl-1-[[(phenylmethoxy)carbonyl]amino]ethyl]phosphinyl]-2-(phenylmethyl)propanoic acid synthesized in 1.7., and 219 mg (0.62 mmol) of phenylmethyl alaninate in the form of the p-toluenesulphonic acid salt. 288 mg of product are recovered (yield=71.9%). | C[C@H](NC(=O)C(Cc1ccccc1)CP(=O)(O)C(Cc1ccccc1)NC(=O)OCc1ccccc1)C(=O)OCc1ccccc1 | null | C[C@H](N)C(=O)OCc1ccccc1 | O=C(NC(Cc1ccccc1)P(=O)(O)CC(Cc1ccccc1)C(=O)O)OCc1ccccc1 | null | [OH:1][P:2]([CH:16]([NH:24][C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH2:4][CH:5]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:6](O)=[O:7])=[O:3].[NH2:35][C@H:36]([C:38]([O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:39])[CH3:37].C1(C)C=CC(S(O)(=O)=O)=CC=1>>[OH:3][P:2]([CH2:4][CH:5]([CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:6]([NH:35][C@H:36]([C:38]([O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:39])[CH3:37])=[O:7])([CH:16]([NH:24][C:25]([O:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)=[O:26])[CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:1] | null | null | null | null | null | 71.9 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
181,184 | null | null | null | null | ord_dataset-ed5a3d1f8dc744759e7fa1c320a44e59 | 1988-01-01T00:11:00 | true | As described in Example 99, (E)-3-(4-methoxyphenyl)-2-butenal (8 g) was treated with (carbomethoxymethylene)triphenylphosphorane (17 g) in carbon tetrachloride (70 mL) and dichloromethane (15 mL) overnight at room temperature. The ester was isolated in the normal fashion and crystallized from hexane to afford 7.2 g of (E,E)-5-(4-methoxyphenyl)-2,4hexadienoic acid methyl ester, mp 84°-86° C. | COC(=O)/C=C/C=C(\C)c1ccc(OC)cc1 | null | COc1ccc(/C(C)=C/C=O)cc1 | COC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1 | null | [CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[C:9](/[CH3:13])=[CH:10]/[CH:11]=O)=[CH:5][CH:4]=1.[C:14]([CH:18]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:16][CH3:17])=[O:15]>C(Cl)(Cl)(Cl)Cl.ClCCl>[CH3:17][O:16][C:14](=[O:15])/[CH:18]=[CH:11]/[CH:10]=[C:9](/[C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)\[CH3:13] | null | ClCCl | ClC(Cl)(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 |
186,416 | Cl | [Na+] | null | null | ord_dataset-754e10d30fb249229e130865010ab25b | 1989-01-01T00:03:00 | true | A thick suspension of the product of stage (b) (3.68 g) in conc. hydrochloric acid (50 ml) was stirred at -5° whilst a solution of sodium nitrite (0.9 g) in water (10 ml) was added dropwise so that temperature did not exceed 0°. Stirring was continued for 30 min. The resulting suspension was filtered to remove starting material and the filtrate added in a few portions to a solution of stannous chloride dihydrate (13.5 g) in hydrochloric acid (15 ml) at -20° and warmed to ambient temperature. The solid that separated was filtered off and recrystallised from hot methanol (100 ml) to give the title compound as white plates (0.39 g) m.p. 192°-193°. The mother liquors afforded a second crop (0.52 g). | NNc1ccc(CS(=O)(=O)NCc2ccccc2)cc1 | null | Nc1ccc(CS(=O)(=O)NCc2ccccc2)cc1 | O=N[O-] | null | [NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][S:9]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:11])=[O:10])=[CH:4][CH:3]=1.[N:20]([O-])=O.[Na+].[ClH:24]>O>[ClH:24].[NH:1]([C:2]1[CH:7]=[CH:6][C:5]([CH2:8][S:9]([NH:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)(=[O:11])=[O:10])=[CH:4][CH:3]=1)[NH2:20] | 0.5 | O | 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 |
1,028,895 | [Pd] | null | null | null | ord_dataset-83acb82dc5ba4f7aba439b9875aaac43 | 2011-01-01T00:02:00 | true | (Method J15F) 6-[3-(1H-Indol-3-yl)-2-(4-1H-indol-3-yl-butyrylamino)-propionylamino]-hexanoic acid benzyloxy-amide (19/97) (1.654 g, 0.274 mmol) was dissolved in ethanol (20 ml), 10% Pd/C (50 mg) was added and the reaction mixture was hydrogenated at room temperature for 4 hours. The catalyst was filtered off, the solvent was evaporated and the residue was chromatographed on silica gel with acetonitrile-acetic acid (60:1) and acetonitrile-acetic acid-water (30:1:1) as eluent to give the title product (0.582 g, 41%) as white powder. M.p. 94-96° C. 1H NMR (DMSO-d6, HMDSO), δ: 1.06-1.55 (m, 6H); 1.68-1.97 (m, 4H); 2.04-2.27 (m, 2H); 2.42-2.67 (m, 2H overlapped with DMSO) 2.80-3.15 (m, 4H); 4.44-4.57 (m, 1H); 6.87-7.17 (m, 6H); 7.31 (d, 2H, J=7.6 Hz); 7.44 (d, 1H, J=7.6 Hz); 7.58 (d, 1H, J=7.6 Hz); 7.80-8.03 (m, 2H); 8.67 (s, 1H); 10.33 (s, 1H); 10.72 (s, 1H); 10.76 ppm (s, 1H). HPLC analysis on Symmetry C8 column: impurities 2.5% (column size 3.9×150 mm; mobile phase acetonitrile −0.1 M phosphate buffer (pH 2.5), 35:65; detector UV 220 nm; sample concentration 0.5 mg/ml, flow rate 1.0 ml/min). Anal. Calcd for C29H35N5O4: C, 67.29; H, 6.82; N, 13.53. Found: C, 67.06; H, 6.86; N, 13.66. | O=C(CCCCCNC(=O)[C@H](Cc1c[nH]c2ccccc12)NC(=O)CCCc1c[nH]c2ccccc12)NO | null | O=C(CCCCCNC(=O)[C@H](Cc1c[nH]c2ccccc12)NC(=O)CCCc1c[nH]c2ccccc12)NOCc1ccccc1 | null | null | C([O:8][NH:9][C:10](=[O:45])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17](=[O:44])[C@@H:18]([NH:29][C:30](=[O:43])[CH2:31][CH2:32][CH2:33][C:34]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[NH:36][CH:35]=1)[CH2:19][C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[NH:22][CH:21]=1)C1C=CC=CC=1>C(O)C.[Pd]>[OH:8][NH:9][C:10](=[O:45])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17](=[O:44])[C@@H:18]([NH:29][C:30](=[O:43])[CH2:31][CH2:32][CH2:33][C:34]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[NH:36][CH:35]=1)[CH2:19][C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[NH:22][CH:21]=1 | 4 | CCO | null | null | null | 410.4 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
553,201 | null | null | null | null | ord_dataset-ec9decb576c4424c9685993f6262bd9c | 2002-01-01T00:07:00 | true | Using a procedure similar to Example 33A and 33B except starting from 2-hydroxyaniline, p-anisoyl chloride and 3-cyanobenzyl bromide, the title compound was obtained as a solid (700 mg, 48%); MS(FD): 358.1. | COc1ccc(C(=O)Nc2ccccc2OCc2cccc(C#N)c2)cc1 | null | Nc1ccccc1O | N#Cc1cccc(CBr)c1 | COc1ccc(C(=O)Cl)cc1 | [OH:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[C:9](Cl)(=[O:18])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1.[C:20]([C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH2:25]Br)#[N:21]>>[C:20]([C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH2:25][O:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][C:9](=[O:18])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)#[N:21] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
696,436 | null | null | null | null | ord_dataset-a7baa616c65d42559e25ca0ba61e0744 | 2006-01-01T00:01:00 | true | Following the procedure for the preparation of (1R,2S)-1-[(3,6-diethylpyrazin-2-yl)amino]-2,3-dihydro-1H-inden-2-ol but substituting 6-methoxy-1,2,3,4-tetrahydronaphthalen-1-amine and making non-critical variations provided the title compound as a oil: HRMS (FAB) calcd for C19H25N3O+H 312.2076, found 312.2075; Anal. Calcd for C19H25N3O: C, 73.28; H, 8.09; N, 13.49. Found C, 73.38; H, 8.11; N, 13.32. | CCc1cnc(CC)c(NC2CCCc3cc(OC)ccc32)n1 | null | COc1ccc2c(c1)CCCC2N | CCc1cnc(CC)c(N[C@@H]2c3ccccc3C[C@@H]2O)n1 | null | [CH2:1]([C:3]1[C:4](N[C@@H]2C3C(=CC=CC=3)C[C@@H]2O)=[N:5][C:6]([CH2:9][CH3:10])=[CH:7][N:8]=1)[CH3:2].[CH3:22][O:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[CH:30]([NH2:34])[CH2:29][CH2:28][CH2:27]2>>[CH2:1]([C:3]1[C:4]([NH:34][CH:30]2[C:31]3[C:26](=[CH:25][C:24]([O:23][CH3:22])=[CH:33][CH:32]=3)[CH2:27][CH2:28][CH2:29]2)=[N:5][C:6]([CH2:9][CH3:10])=[CH:7][N:8]=1)[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 |
42,082 | [Na+] | [OH-] | null | null | ord_dataset-48929f64ce614f1181a555eafd7c97a6 | 1978-01-01T00:06:00 | true | 30 g (0.15 mol) of 4-chloromethyl-hydrocinnamic acid (J. Org, Chem. 26, 148 (1961) in 200 ml of water were neutralized with a 10% sodium hydroxide solution against phenol phthaline. 10% of NaOH (on the whole about 60 ml) were added dropwise, while stirring at reflux temperature, to the solution obtained in the same measure as it was consumed. When the reaction was finished, the mixture was saturated with sodium chloride, acidified with concentrated hydrochloric acid, the product precipitated was suction-filtered and washed with water. Melting point: 124°-126° C. | O=C(O)CCc1ccc(CO)cc1 | null | O=C(O)c1ccccc1C(c1ccc(O)cc1)c1ccc(O)cc1 | O=C(O)CCc1ccc(CCl)cc1 | null | Cl[CH2:2][C:3]1[CH:13]=[CH:12][C:6]([CH2:7][CH2:8][C:9]([OH:11])=[O:10])=[CH:5][CH:4]=1.[OH-].[Na+].C1C=C(C(C2C=CC(O)=CC=2)C2C=CC([OH:29])=CC=2)C(C(O)=O)=CC=1>O>[OH:29][CH2:2][C:3]1[CH:13]=[CH:12][C:6]([CH2:7][CH2:8][C:9]([OH:11])=[O:10])=[CH:5][CH:4]=1 | null | 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 |
1,615,363 | Cl | null | null | null | ord_dataset-35c51552812941cda45194a013d34bb9 | 2015-01-01T00:08:00 | true | To a solution of (S)-tert-butyl ((3-bromopyridin-2-yl)(4-(trifluoromethyl)-phenyl)methyl)carbamate (2.0 g, 4.64 mmol) in MeOH (10 mL) was added hydrogen chloride (3.48 mL, 13.91 mmol) (4.0 M in 1,4-dioxane). The reaction was stirred for 27 h at rt under N2. The reaction was concentrated in vacuo to give the amine which was used without further purification in subsequent steps. MS (ESI pos. ion) m/z: 331.0, 332.9 (M+H). | N[C@@H](c1ccc(C(F)(F)F)cc1)c1ncccc1Br | null | CC(C)(C)OC(=O)N[C@@H](c1ccc(C(F)(F)F)cc1)c1ncccc1Br | null | null | [Br:1][C:2]1[C:3]([C@@H:8]([NH:19]C(=O)OC(C)(C)C)[C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[ClH:27]>CO>[ClH:27].[Br:1][C:2]1[C:3]([C@H:8]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:17])([F:18])[F:16])=[CH:11][CH:10]=2)[NH2:19])=[N:4][CH:5]=[CH:6][CH:7]=1 | 27 | CO | 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 |
128,457 | [Li]CCCC | null | null | null | ord_dataset-d6b60b593b1c4668bc6843cd65a5d232 | 1985-01-01T00:04:00 | true | A solution of 10.0 g (32.8 mmol) of (1,1'-biphenyl-4-yl)(chloromethyl)methyl(2-propoxy)silane and 3.6 ml (32.8 mmol) of 4-bromofluorobenzene in 30 ml of dry tetrahydrofuran was cooled to -60° under nitrogen and stirred while 20.5 ml (32.8 mmol) of 1.6 molar n-butyllithium in hexane was added at a rate that held the mixture below 50°. After stirring at -70° for another 30 minutes, the solution was allowed to warm to room temperature and was worked up as in Example 8. The resulting crude product was subjected to distillation at 130°-150° (0.2 mm) to remove unreacted starting material, leaving the title compound as an oil: nD23 1.5128; nmr (CDCl3): 0.7 (3H, s), 3.1 (2H, s), 7.1 (2H, t), 7.2-7.8 (11H, m). | Fc1ccc(C[SiH](CCl)c2ccc(-c3ccccc3)cc2)cc1 | null | CC(C)O[Si](C)(CCl)c1ccc(-c2ccccc2)cc1 | Fc1ccc(Br)cc1 | null | [C:1]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=[CH:5][C:4]([Si:7]([CH2:13][Cl:14])([CH3:12])OC(C)C)=[CH:3][CH:2]=1.Br[C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1.C([Li])CCC>O1CCCC1.CCCCCC>[C:1]1([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:2]=[CH:3][C:4]([SiH:7]([CH2:13][Cl:14])[CH2:12][C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)=[CH:5][CH:6]=1 | 0.5 | C1CCOC1 | CCCCCC | 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 |
1,324,704 | null | null | null | null | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | 2013-01-01T00:08:00 | true | 3-Bromo-2-methoxybenzoic acid (2 g, 8.65 mmol, 1.0 eq) was dissolved in dry DCM and stirred for 10 minutes, cooled to 0° C. and slowly treated with oxalyl chloride (3.3 g, 25.9 mmol, 3 eq). Methanol in pyridine was added dropwise and the reaction mixture was stirred at ambient temperature. The solvents were evaporated under reduced pressure and the reaction mass was diluted with water. The aqueous mixture was extracted with ethyl acetate. The organic layer was dried with anhydrous Na2SO4 and concentrated under vacuum to afford the desired product (1.9 g, 90%). 1H NMR (400 MHz, CDCl3) δ 3.93 (s, 6H), 7.02-6.06 (t, 1H), 7.72-7.76 (m, 2H). MS (ESI): 247.0 (M+H)+. | COC(=O)c1cccc(Br)c1OC | null | COc1c(Br)cccc1C(=O)O | O=C(Cl)C(=O)Cl | null | [Br:1][C:2]1[C:3]([O:11][CH3:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[C:13](Cl)(=O)C(Cl)=O.CO>C(Cl)Cl.N1C=CC=CC=1>[Br:1][C:2]1[C:3]([O:11][CH3:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH3:13])=[O:6] | 0.17 | c1ccncc1 | ClCCl | CO | 0 | 89.6 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
505,816 | [Cl-] | [Li]CCCC | [NH4+] | null | ord_dataset-631d58dab387485c8eb0db4c20a232b7 | 2001-01-01T00:06:00 | true | To a solution of diisopropylamine (1.33 ml) in tetrahydrofuran (20 ml) is added gradually and dropwise a 1.6 N solution of n-butyl lithium in hexane (5.91 ml) at 0° C., and the mixture is stirred at the same temperature for 30 minutes. The solution is cooled to −78° C., and thereto is added gradually and dropwise a solution of (Z)-4-(3-chloro-4,5-dimethoxyphenyl)-4-methyl-3-methoxycarbonyl-3-butenoic acid methoxymethyl ester (2.94 g) in tetrahydrofuran (20 ml), and the mixture is further stirred at the same temperature for 30 minutes. The reaction mixture is cooled to −90° C., and thereto is added gradually and dropwise a solution of isonictinaldehyde (1.01 g) in tetrahydrofuran (10 ml), and the mixture is stirred at −90° C. for 20 minutes. To the reaction mixture is added a saturated aqueous ammonium chloride solution, and the mixture is extracted with ethyl acetate. The organic layer is washed, dried, and concentrated under reduced pressure to remove the solvent to give (Z)-4-(3-chloro-4,5-dimethoxyphenyl)-4-methyl-3-methoxycarbonyl-2-(4-pyridylhydroxymethyl)-3-butenoic acid methoxymethyl ester. | COCOC(=O)C(/C(C(=O)OC)=C(\C)c1cc(Cl)c(OC)c(OC)c1)C(O)c1ccncc1 | null | COCOC(=O)C/C(C(=O)OC)=C(\C)c1cc(Cl)c(OC)c(OC)c1 | C1CCOC1 | CC(C)NC(C)C | [CH:1]([NH:4][CH:5]([CH3:7])C)([CH3:3])C.C([Li])CCC.[CH3:13][O:14][CH2:15][O:16][C:17](=[O:37])[CH2:18]/[C:19](/[C:33]([O:35][CH3:36])=[O:34])=[C:20](/[C:22]1[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[C:24]([Cl:32])[CH:23]=1)\[CH3:21].[Cl-].[NH4+].[O:40]1CC[CH2:42][CH2:41]1>CCCCCC>[CH3:13][O:14][CH2:15][O:16][C:17](=[O:37])[CH:18]([CH:41]([C:42]1[CH:3]=[CH:1][N:4]=[CH:5][CH:7]=1)[OH:40])/[C:19](/[C:33]([O:35][CH3:36])=[O:34])=[C:20](/[C:22]1[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[C:24]([Cl:32])[CH:23]=1)\[CH3:21] | null | CCCCCC | null | null | -78 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,406,545 | C=O | null | null | null | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | 2014-01-01T00:03:00 | true | A mixture of (−)-3-(3,4-difluorophenyl)-3-methoxypyrrolidine (0.013 g, 0.061 mmol) in formic acid (1 ml) and formaldehyde (37% solution in water, 1 ml) was heated at 85° C. for 5 h. The solution was allowed to reach room temperature. The crude mixture was purified on a Biotage Isolute SCX-3 SPE column (washed with methanol and eluted with methanol/triethylamine, 4:1). The solvent was evaporated. The crude product analyzed by GCMS. Analysis showed 87% conversion. MS m/z (relative intensity, 70 eV) 227 (M+, 5), 212 (26), 197 (30), 141 (47), 57 (bp). | COC1(c2ccc(F)c(F)c2)CCN(C)C1 | null | O=CO | COC1(c2ccc(F)c(F)c2)CCNC1 | null | [F:1][C:2]1[CH:3]=[C:4]([C:9]2([O:14][CH3:15])[CH2:13][CH2:12][NH:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[CH:16](O)=O>C=O>[F:1][C:2]1[CH:3]=[C:4]([C:9]2([O:14][CH3:15])[CH2:13][CH2:12][N:11]([CH3:16])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8] | null | null | null | null | 85 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,436,112 | Cl | [Na+] | [OH-] | null | ord_dataset-275a3da8f45f4536ad29727f0ef9ba66 | 2014-01-01T00:06:00 | true | To methyl 8-(4-(2-butoxyethoxy)phenyl)-1-(2-methyl-2-propen-1-yl)-1,2,3,4-tetrahydro-1-benzoazocine-5-carboxylate (1.65 g) were added tetrahydrofuran (45 ml) and methanol (45 ml), followed by adding an aqueous 1N sodium hydroxide solution (15 ml), and the mixture was stirred at 60° C. overnight. After cooling down to 0° C., water was added and the mixture was neutralized with 1N hydrochloric acid. After extracting with ethyl acetate, the organic layer was washed with saturated water and dried with magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was recrystallized from hexane-ethyl acetate to give 8-(4-(2-butoxyethoxy)phenyl)-1-(2-methyl-2-propen-1-yl)-1,2,3,4-tetrahydro-1-benzoazocine-5-carboxylic acid (0.97 g) as yellow crystals. | C=C(C)CN1CCCC(C(=O)O)=Cc2cc(-c3ccc(OCCOCCCC)cc3)ccc21 | null | C=C(C)CN1CCCC(C(=O)OC)=Cc2cc(-c3ccc(OCCOCCCC)cc3)ccc21 | null | null | [CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:25]([CH2:26][C:27]([CH3:29])=[CH2:28])[CH2:24][CH2:23][CH2:22][C:21]([C:30]([O:32]C)=[O:31])=[CH:20][C:19]=3[CH:34]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4].O1CCCC1.[OH-].[Na+].Cl>O.CO>[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:25]([CH2:26][C:27]([CH3:29])=[CH2:28])[CH2:24][CH2:23][CH2:22][C:21]([C:30]([OH:32])=[O:31])=[CH:20][C:19]=3[CH:34]=2)=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH3:4] | 8 | O | C1CCOC1 | CO | 60 | null | 60.6 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
314,704 | null | null | null | null | ord_dataset-bd998d3fe946475e835418aaf647c00d | 1995-01-01T00:08:00 | true | By the method described in Example 5, the title compound of Example 4 (0.5 g, 1.5 mmol) in 20 mL of CH2Cl2 was converted to its mixed anhydride with NMM (0.16 mL, 1.5 mmol) and IBCF (0.2 mL, 1.5 mmol). This intermediate was condensed with 4-aminopyridine (0.21 g, 2.25 mmol) to produce the title compound (94 mg). | O=C(CNC(=O)N1Cc2ccccc2Oc2ccc(Cl)cc21)Nc1ccncc1 | null | O=C(O)CNC(=O)N1Cc2ccccc2Oc2ccc(Cl)cc21 | Nc1ccncc1 | null | [Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[O:6][C:7]3[CH:21]=[CH:20][CH:19]=[CH:18][C:8]=3[CH2:9][N:10]([C:11]([NH:13][CH2:14][C:15]([OH:17])=O)=[O:12])[C:4]=2[CH:3]=1.CN1CCOCC1.[NH2:31][C:32]1[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=1>C(Cl)Cl>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[O:6][C:7]3[CH:21]=[CH:20][CH:19]=[CH:18][C:8]=3[CH2:9][N:10]([C:11]([NH:13][CH2:14][C:15]([NH:31][C:32]3[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=3)=[O:17])=[O:12])[C:4]=2[CH:3]=1 | null | CN1CCOCC1 | ClCCl | null | null | 15.3 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
602,589 | null | null | null | null | ord_dataset-82e842e611ef4a05b6e7f9ea0a46d52d | 2003-01-01T00:07:00 | true | To a stirred, cold (0° C.) solution of (2R,4R)-1-[3-(4-fluorophenoxy)-propane-1-sulfonyl]-piperidine-2,4-dicarboxylic acid 2-tert-butyl ester 4-methyl ester (1.15 g, 2.5 mmol) in 10 mL of methylene chloride was added 10 mL of trifluoracetic acid. The mixture was allowed warm to ambient temperature (22° C.) over 16 hours. The mixture was concentrated in vacuo to give 970 mg of crude (2R,4R)-1-[3-(4-fluorophenoxy)-propane-1-sulfonyl]-piperidine-2,4-dicarboxylic acid 4-methyl ester as a orange solid. | COC(=O)[C@@H]1CCN(S(=O)(=O)CCCOc2ccc(F)cc2)[C@@H](C(=O)O)C1 | null | COC(=O)[C@@H]1CCN(S(=O)(=O)CCCOc2ccc(F)cc2)[C@@H](C(=O)OC(C)(C)C)C1 | null | null | [CH3:1][O:2][C:3]([C@@H:5]1[CH2:10][CH2:9][N:8]([S:11]([CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)(=[O:13])=[O:12])[C@@H:7]([C:25]([O:27]C(C)(C)C)=[O:26])[CH2:6]1)=[O:4].FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:10][CH2:9][N:8]([S:11]([CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)(=[O:13])=[O:12])[C@@H:7]([C:25]([OH:27])=[O:26])[CH2:6]1)=[O:4] | null | ClCCl | O=C(O)C(F)(F)F | null | 22 | 96.2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,145,242 | CC(C)(C)[O-] | [K+] | null | null | ord_dataset-68715347640045adb1b09e6a04722b0e | 2012-01-01T00:03:00 | true | 4-[2-(2,4-Dichloro-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-1H-pyridin-2-one (Example 119, 100 mg) was dissolved in THF (10 mL), and treated with t-BuOK (34 mg). After 5 minutes stirring, bromo-acetic acid methyl ester (0.03 mL) was added and the reaction mixture was stirred at 55° C. for 17 h. The reaction mixture was then cooled down to r.t., poured into water (50 mL) and extracted twice with ethyl acetate. The combined organic phases were washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography (10 g silica gel, ethyl acetate/heptane 30:70) to give the title compound as colorless waxy solid (49 mg). MS (m/e)=438.1 (MH+). | COC(=O)Cn1ccc(C(O)(C(C)c2ccc(Cl)cc2Cl)C(F)(F)F)cc1=O | null | CC(c1ccc(Cl)cc1Cl)C(O)(c1cc[nH]c(=O)c1)C(F)(F)F | COC(=O)CBr | null | [Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH3:23])[C:10]([C:16]1[CH:21]=[CH:20][NH:19][C:18](=[O:22])[CH:17]=1)([OH:15])[C:11]([F:14])([F:13])[F:12].CC([O-])(C)C.[K+].[CH3:30][O:31][C:32](=[O:35])[CH2:33]Br.O>C1COCC1>[CH3:30][O:31][C:32](=[O:35])[CH2:33][N:19]1[CH:20]=[CH:21][C:16]([C:10]([OH:15])([C:11]([F:14])([F:13])[F:12])[CH:9]([C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[CH3:23])=[CH:17][C:18]1=[O:22] | 0.08 | 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 |
589,959 | null | null | null | null | ord_dataset-7a74d48eeefd45aba53e7258f3ae067a | 2003-01-01T00:04:00 | true | The title compound was prepared from {5-(methyl-propyl-amino)-2-[3-oxo-3-(3-[1,2,3]-triazol-1-yl-phenyl)-propionylamino]-4-trifluoromethyl-phenyl}-carbamic acid tert-butyl ester (Example M118) (0.33 g, 0.59 mmol) by treatment with TFA in CH2Cl2 according to the general procedure N. Obtained as a light yellow solid (115 mg, 44%). | CCCN(C)c1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-n3ccnn3)c1)=N2 | null | CCCN(C)c1cc(NC(=O)OC(C)(C)C)c(NC(=O)CC(=O)c2cccc(-n3ccnn3)c2)cc1C(F)(F)F | null | null | C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([N:14]([CH3:18])[CH2:15][CH2:16][CH3:17])[C:11]([C:19]([F:22])([F:21])[F:20])=[CH:10][C:9]=1[NH:23][C:24](=[O:39])[CH2:25][C:26](=O)[C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([N:33]2[CH:37]=[CH:36][N:35]=[N:34]2)[CH:28]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:18][N:14]([CH2:15][CH2:16][CH3:17])[C:12]1[C:11]([C:19]([F:20])([F:22])[F:21])=[CH:10][C:9]2[NH:23][C:24](=[O:39])[CH2:25][C:26]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([N:33]4[CH:37]=[CH:36][N:35]=[N:34]4)[CH:28]=3)=[N:7][C:8]=2[CH:13]=1 | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,620,166 | [BH4-] | [Na+] | null | null | ord_dataset-35c51552812941cda45194a013d34bb9 | 2015-01-01T00:08:00 | true | A solution of ethyl 2-tert-butoxy-2-(1-(4-chlorophenyl)-4-formyl-3-methylnaphthalen-2-yl)acetate (6.0 mg, 14 μmol), NaBH4 (1.5 mg, 40 μmol), THF (250 μL), and EtOH (absolute, 500 μL) was stirred at 23° C. for 1 h. H2O (500 μL) and LiOH monohydrate (50 mg, 1.18 mmol) were added. The reaction was sealed and heated to 100° C. After 2 h, the reaction cooled to 23° C., filtered through a 0.45 micron filter, and directly purified by reverse phase HPLC (Gemini, 5 to 100% ACN/H2O+0.1% TFA). The product-containing fractions were combined and lyophilized, giving the title compound (parent form) (2.6 mg, 43%). 1H NMR (400 MHz, DMSO-d6) δ 12.76 (s, 1H), 8.27 (d, J=8.6 Hz, 1H), 7.72-7.65 (m, 2H), 7.58-7.48 (m, 2H), 7.39-7.33 (m, 2H), 7.18 (d, J=8.6 Hz, 1H), 5.07 (s, 1H), 5.01 (d, broad, J=2.7 Hz, 2H), 2.62 (s, 3H), 0.94 (s, 9H). | Cc1c(C(OC(C)(C)C)C(=O)O)c(-c2ccc(Cl)cc2)c2ccccc2c1CO | null | CCOC(=O)C(OC(C)(C)C)c1c(C)c(C=O)c2ccccc2c1-c1ccc(Cl)cc1 | null | null | [C:1]([O:5][CH:6]([C:12]1[C:21]([CH3:22])=[C:20]([CH:23]=[O:24])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]=1[C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1)[C:7]([O:9]CC)=[O:8])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].C1COCC1.CCO>O>[C:1]([O:5][CH:6]([C:12]1[C:21]([CH3:22])=[C:20]([CH2:23][OH:24])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]=1[C:25]1[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3] | 2 | C1CCOC1 | CCO | O | 100 | 45 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
760,260 | null | null | null | null | ord_dataset-2e58cb8db2bf482bbea23283b7e04488 | 2007-01-01T00:03:00 | true | A thiourea such as N-[4-(isopropylformylamino)cyclohexyl]-methylthiourea (0.029 mmol, 1 equivalent), a bromoketone (0.044 mmol, 1.5 equivalent) and 2 equivalents of diisopropylethyl amine in 10 ml of EtOH were heated at reflux temperature for 2 days. The reaction mixture was concentrated in vacuo and the crude product chromatographed (silica) to obtain the desired product. This procedure was used to prepare examples 101–102. | CC(C)C(=O)NC1CCC(CNC(N)=S)CC1 | null | CC(C)C(=O)NC1CCC(N(C)C(N)=S)CC1 | NC(N)=S | O=C(Br)Br | [NH2:1][C:2]([NH2:4])=[S:3].[CH:5]([C:8]([NH:10][CH:11]1[CH2:16][CH2:15][CH:14](N(C)C(N)=S)[CH2:13][CH2:12]1)=[O:9])([CH3:7])[CH3:6].Br[C:23](Br)=O.C(N(C(C)C)CC)(C)C>CCO>[CH:5]([C:8]([NH:10][CH:11]1[CH2:16][CH2:15][CH:14]([CH2:23][NH:1][C:2]([NH2:4])=[S:3])[CH2:13][CH2:12]1)=[O:9])([CH3:7])[CH3:6] | null | CCN(C(C)C)C(C)C | 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 |
1,493,961 | CCOC(=O)/N=N/C(=O)OCC | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | 2014-01-01T00:10:00 | true | To a round-bottomed flask was added methyl 2-(5-hydroxypyridin-2-yl)thiazole-5-carboxylate (400 mg), (S)-3-hydroxy-pyrrolidin-2-one (188 mg), PPh3 (443 mg), and THF (10 mL). DEAD (299 mg) was added dropwise at 0° C. under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 12 hours. After being diluted with ethyl acetate (50 mL), the organic layer was washed with water (20 mL×2) and brine (10 mL) and dried over anhydrous Na2SO4. After filtration and evaporation of the solvent, the residue obtained was purified by silica gel column chromatography eluting with petroleum ether/ethyl acetate (4:1 to 1:3) to afford the subtitle compound. MS ESI+: m/z=320 [M-FH]+. | COC(=O)c1cnc(-c2ccc(O[C@@H]3CCNC3=O)cn2)s1 | null | O=C1NCC[C@@H]1O | COC(=O)c1cnc(-c2ccc(O)cn2)s1 | null | [OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][C:10]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][N:12]=2)=[N:6][CH:7]=1.O[C@H:18]1[CH2:22][CH2:21][NH:20][C:19]1=[O:23].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C(OCC)(=O)C.C1COCC1>[O:23]=[C:19]1[C@H:18]([O:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[S:9][C:10]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][N:12]=3)=[N:6][CH:7]=2)[CH2:22][CH2:21][NH:20]1 | 12 | C1CCOC1 | CCOC(C)=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 |
219,838 | N | [H-] | [Na+] | null | ord_dataset-6cb04513a4a244c0b612b566096f4b3d | 1990-01-01T00:12:00 | true | 5-[1-(dimethylamino)-ethylideneamino]-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-imidazole-4-carbonitrile is reacted with sodium hydride in dioxane as described in Example 10 and the crude product is reacted with methanolic ammonia at room temperature over 18 hours. The mixture is concentrated to dryness and purified by silica gel chromatography to afford 7-amino-3-β-D-ribofuranosyl-N,N-dimethyl-3H-imidazo[4,5-b]pyridine-5-amine. | CN(C)c1cc(N)c2ncn([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)c2n1 | null | CC(=O)OC[C@H]1O[C@@H](n2cnc(C#N)c2N=C(C)N(C)C)[C@H](OC(C)=O)[C@@H]1OC(C)=O | null | null | [CH3:1][N:2]([CH3:31])[C:3](=[N:5][C:6]1[N:10]([C@@H:11]2[O:23][C@H:22]([CH2:24][O:25]C(=O)C)[C@@H:17]([O:18]C(=O)C)[C@H:12]2[O:13]C(=O)C)[CH:9]=[N:8][C:7]=1[C:29]#[N:30])[CH3:4].[H-].[Na+].N>O1CCOCC1>[NH2:30][C:29]1[CH:4]=[C:3]([N:2]([CH3:31])[CH3:1])[N:5]=[C:6]2[N:10]([C@@H:11]3[O:23][C@H:22]([CH2:24][OH:25])[C@@H:17]([OH:18])[C@H:12]3[OH:13])[CH:9]=[N:8][C:7]=12 | 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 |
1,283,604 | null | null | null | null | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | 2013-01-01T00:04:00 | true | 4-Chloro-2-methylquinoline-8-sulfonic dimethylamide (80 mg, 0.281 mmole) and 3,4-dichlorobenzylamine (100 mg, 0.568 mmole) were stirred at 155° C. for 10 min in a microwave oven. Methanol was added and the mixture was concentrated, mixed with dichloromethane and then filtered. The residue was purified using silica gel chromatography, eluting with dichloromethane:methanol 95:5. Precipitation in ethyl acetate gave a pink solid (15 mg, 13%). | Cc1cc(NCc2ccc(Cl)c(Cl)c2)c2cccc(S(=O)(=O)N(C)C)c2n1 | null | NCc1ccc(Cl)c(Cl)c1 | Cc1cc(Cl)c2cccc(S(=O)(=O)N(C)C)c2n1 | null | [CH3:1][N:2]([CH3:18])[S:3]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[C:11]2Cl)(=[O:5])=[O:4].[Cl:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[Cl:28])[CH2:23][NH2:24]>CO>[CH3:1][N:2]([CH3:18])[S:3]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[C:11]2[NH:24][CH2:23][C:22]1[CH:25]=[CH:26][C:27]([Cl:28])=[C:20]([Cl:19])[CH:21]=1)(=[O:5])=[O:4] | null | CO | null | null | null | 12.6 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,607,224 | null | null | null | null | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | 2015-01-01T00:07:00 | true | The title compound was prepared in a manner similar to that described in Example 448 using 5-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-pyrazin-2-amine and racemic tert-butyl (1-((2-bromophenyl)sulfonyl)piperidin-3-yl)carbamate. MS (ESI): mass calcd. for C26H30FN5O4S, 527.20; m/z found, 528.3 [M+H]+. 1H NMR (400 MHz, CD3OD) δ 8.34 (d, J=9.1, 2H), 8.10-8.07 (m, 1H), 8.00 (m, 1H), 7.73-7.68 (m, 1H), 7.64-7.59 (m, 1H), 7.44-7.40 (m, 1H), 7.35-7.29 (m, 2H), 3.30-3.20 (m, 2H), 3.15-3.06 (m, 1H), 2.51-2.40 (m, 1H), 2.30-2.21 (m, 1H), 1.79-1.70 (m, 1H), 1.65-1.56 (m, 1H), 1.39-1.28 (m, 10H), 1.26-1.14 (m, 1H). | CC(C)(C)OC(=O)NC1CCCN(S(=O)(=O)c2ccccc2-c2ccc(-c3cnc(N)cn3)c(F)c2)C1 | null | CC(C)(C)OC(=O)NC1CCCN(S(=O)(=O)c2ccccc2Br)C1 | CC1(C)OB(c2ccc(-c3cnc(N)cn3)c(F)c2)OC1(C)C | null | [F:1][C:2]1[CH:7]=[C:6](B2OC(C)(C)C(C)(C)O2)[CH:5]=[CH:4][C:3]=1[C:17]1[N:18]=[CH:19][C:20]([NH2:23])=[N:21][CH:22]=1.Br[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[S:31]([N:34]1[CH2:39][CH2:38][CH2:37][CH:36]([NH:40][C:41](=[O:47])[O:42][C:43]([CH3:46])([CH3:45])[CH3:44])[CH2:35]1)(=[O:33])=[O:32]>>[NH2:23][C:20]1[N:21]=[CH:22][C:17]([C:3]2[CH:4]=[CH:5][C:6]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[S:31]([N:34]3[CH2:39][CH2:38][CH2:37][CH:36]([NH:40][C:41](=[O:47])[O:42][C:43]([CH3:45])([CH3:44])[CH3:46])[CH2:35]3)(=[O:32])=[O:33])=[CH:7][C:2]=2[F:1])=[N:18][CH:19]=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 |
435,581 | Cl | [Li+] | [OH-] | null | ord_dataset-386da077ab2340638cada986e2ef0770 | 1999-01-01T00:07:00 | true | A solution of 20 g of 4-[N'-methyl-N'-(3,5-bistrifluoromethyl-benzoyl)-amino]-5-(4-chlorophenyl)-pent-2-enoic acid ethyl ester and 15 g of lithium hydroxide monohydrate in 100 ml of THF/methanol/water 3:3:1 is stirred at room temperature for 4 hours, and then 200 ml of water and 1N hydrochloric acid are added (pH value approx. 2). The mixture is extracted twice with ethyl acetate. The combined organic phases are washed with water and saturated NaCl solution, dried (magnesium sulfate) and concentrated by evaporation. The title compound is obtained in the form of a colourless oil which can be used further without being further purified. | CN(C(=O)c1cc(C(F)(F)F)cc(C(F)(F)F)c1)C(C=CC(=O)O)Cc1ccc(Cl)cc1 | null | CCOC(=O)C=CC(Cc1ccc(Cl)cc1)N(C)C(=O)c1cc(C(F)(F)F)cc(C(F)(F)F)c1 | null | null | C([O:3][C:4](=[O:34])[CH:5]=[CH:6][CH:7]([N:16]([CH3:33])[C:17](=[O:32])[C:18]1[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[C:20]([C:28]([F:31])([F:30])[F:29])[CH:19]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)C.O.[OH-].[Li+].O.Cl>C1COCC1.CO.O>[CH3:33][N:16]([CH:7]([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([Cl:15])=[CH:13][CH:14]=1)[CH:6]=[CH:5][C:4]([OH:34])=[O:3])[C:17](=[O:32])[C:18]1[CH:19]=[C:20]([C:28]([F:29])([F:30])[F:31])[CH:21]=[C:22]([C:24]([F:25])([F:26])[F:27])[CH:23]=1 | null | O | C1CCOC1 | 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 |
492,442 | null | null | null | null | ord_dataset-3f9174c7efcb4f31becbd3516cde9572 | 2001-01-01T00:02:00 | true | By the same reaction and treatment as in Example 48 using cycloheptanone oxime and ethyl 4-(4-(4-chloro-3-trifluoromethylphenyl)piperidin-1-yl)-n-butyrate, 3-(3-(4-(4-chloro-3-trifluoromethylphenyl)piperidin-1-yl)propyl)-5,6,7,8-tetrahydro-4H-cyclohepta[c]isoxazole is obtained. | FC(F)(F)c1cc(C2CCN(CCCc3onc4c3CCCCC4)CC2)ccc1Cl | null | ON=C1CCCCCC1 | CCOC(=O)CCCN1CCC(c2ccc(Cl)c(C(F)(F)F)c2)CC1 | null | [C:1]1(=[N:8][OH:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][CH2:25][C:26](OCC)=O)[CH2:19][CH2:18]2)=[CH:13][C:12]=1[C:31]([F:34])([F:33])[F:32]>>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][CH2:25][C:26]3[O:9][N:8]=[C:1]4[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2]=34)[CH2:19][CH2:18]2)=[CH:13][C:12]=1[C:31]([F:34])([F:32])[F:33] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
781,124 | Cl | null | null | null | ord_dataset-8034115bd2ec4d3e95bd3ff7cfde0bde | 2007-01-01T00:07:00 | true | A mixture of 6-(1-(tert-butyloxycarbonyl)piperidin-4-yloxy)-4H-benzo[1,4]oxazin-3-one (3.78 g, 10.9 mmol), ethereal hydrogen chloride (50 mL) and dichloromethane (20 mL) was heated at 40° C. for 2 h, then allowed to stir at 20° C. for 18 h. The resulting colourless solid was collected by filtration to give the title compound (2.72 g, 88%). | O=C1COc2ccc(OC3CCNCC3)cc2N1 | null | CC(C)(C)OC(=O)N1CCC(Oc2ccc3c(c2)NC(=O)CO3)CC1 | null | null | C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:16]=[CH:17][C:18]3[O:23][CH2:22][C:21](=[O:24])[NH:20][C:19]=3[CH:25]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:26]>ClCCl>[ClH:26].[NH:8]1[CH2:9][CH2:10][CH:11]([O:14][C:15]2[CH:16]=[CH:17][C:18]3[O:23][CH2:22][C:21](=[O:24])[NH:20][C:19]=3[CH:25]=2)[CH2:12][CH2:13]1 | 18 | ClCCl | null | null | 40 | null | 88 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,432,519 | null | null | null | null | ord_dataset-5e6956e6e8c24a168866a253f4a66c6c | 2014-01-01T00:05:00 | true | N-(2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamidoethyl)-2′,4′-difluoro-4-hydroxybiphenyl-3-carboxamide was prepared in a similar fashion as N-(2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamidoethyl)-2-hydroxybenzamide, using the appropriate 2′,4′-difluoro-4-hydroxybiphenyl-3-carboxylic acid starting material. Mass calculated for C37H44F2N2O3=602.75. found: [M+H]+=603.3. | CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)NCCNC(=O)c1cc(-c2ccc(F)cc2F)ccc1O | null | CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)NCCNC(=O)c1ccccc1O | O=C(O)c1cc(-c2ccc(F)cc2F)ccc1O | null | [C:1]([NH:24][CH2:25][CH2:26][NH:27][C:28](=[O:36])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[OH:35])(=[O:23])[CH2:2][CH2:3]/[CH:4]=[CH:5]\[CH2:6]/[CH:7]=[CH:8]\[CH2:9]/[CH:10]=[CH:11]\[CH2:12]/[CH:13]=[CH:14]\[CH2:15]/[CH:16]=[CH:17]\[CH2:18]/[CH:19]=[CH:20]\[CH2:21][CH3:22].[F:37][C:38]1[CH:43]=[C:42]([F:44])[CH:41]=[CH:40][C:39]=1C1C=CC(O)=C(C(O)=O)C=1>>[C:1]([NH:24][CH2:25][CH2:26][NH:27][C:28]([C:29]1[CH:34]=[C:33]([C:41]2[CH:40]=[CH:39][C:38]([F:37])=[CH:43][C:42]=2[F:44])[CH:32]=[CH:31][C:30]=1[OH:35])=[O:36])(=[O:23])[CH2:2][CH2:3]/[CH:4]=[CH:5]\[CH2:6]/[CH:7]=[CH:8]\[CH2:9]/[CH:10]=[CH:11]\[CH2:12]/[CH:13]=[CH:14]\[CH2:15]/[CH:16]=[CH:17]\[CH2:18]/[CH:19]=[CH:20]\[CH2:21][CH3:22] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
700,325 | OP(O)O | [I-] | [K+] | null | ord_dataset-bbd7e53f000345838ad4920a07a169ff | 2006-01-01T00:03:00 | true | To a solution of hydroxy(1-acetyl-4,6-dimethylindolin-5-yl)acetic acid obtained in Example 1 (280 g) in acetic acid (1120 ml) were added phosphorous acid (130 g) and potassium iodide (17.6 g), and the resulting mixture was stirred for 2 hours at 100–107° C. After cooling to 50° C., water (1120 ml) was added, and crystals precipitated were separated by filtration and dried to afford (1-acetyl-4,6-dimethylindolin-5-yl)acetic acid (223 g, yield: 85%). | CC(=O)N1CCc2c1cc(C)c(CC(=O)O)c2C | null | CC(=O)N1CCc2c1cc(C)c(C(O)C(=O)O)c2C | null | null | O[CH:2]([C:6]1[C:7]([CH3:19])=[C:8]2[C:12](=[CH:13][C:14]=1[CH3:15])[N:11]([C:16](=[O:18])[CH3:17])[CH2:10][CH2:9]2)[C:3]([OH:5])=[O:4].P(O)(O)O.[I-].[K+].O>C(O)(=O)C>[C:16]([N:11]1[C:12]2[C:8](=[C:7]([CH3:19])[C:6]([CH2:2][C:3]([OH:5])=[O:4])=[C:14]([CH3:15])[CH:13]=2)[CH2:9][CH2:10]1)(=[O:18])[CH3:17] | 2 | CC(=O)O | O | null | 50 | 84.8 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
274,531 | null | null | null | null | ord_dataset-ee287d49cb8642e59ae9c3951f746312 | 1993-01-01T00:08:00 | true | A solution of [3-[[2-(diethoxyphosphinyl)ethyl]amino]propyl]carbamic acid phenylmethyl ester (3.17 g, 8.5 mmol) in absolute ethanol (40 mL) was added over 45 minutes to 3,4-diethoxy-3-cyclobutene-1,2-dione (2.3 mL, 16 mmol) dissolved ethanol (55 mL). After leaving overnight, the reaction mixture was preadsorbed onto silica gel and purified by flash chromotography (7 cm diameter, gradient elution was 2.5-10% methanol in dichloromethane) to yield [3-[[2-(diethoxyphosphinyl)ethyl](2-ethoxy-3,4-dioxo-1-cyclobuten-1-yl)amino]propyl]carbamic acid phenylmethyl ester as a viscous oil (3.75 g, 89%); 1H NMR (CDCl3, 400 MHz): δ 7.35 (m, 5H), 5.45 (br m, NH), 5.09 (s, 2H), 4.80-4.71 (m, 2H), 4.16-4.09 (m, 4H), 3.90-3.48 (m, 4H), 3.23-3.20 (m, 2H), 2.16-2.05 (m, 2 H), 1.85-1.79 (m, 2H), 1.47, 1.41 (t, J=7 Hz, 3H), 1.34 (t, J=7 Hz, 6H). | CCOc1c(N(CCCNC(=O)OCc2ccccc2)CCP(=O)(OCC)OCC)c(=O)c1=O | null | CCOc1c(OCC)c(=O)c1=O | CCOP(=O)(CCNCCCNC(=O)OCc1ccccc1)OCC | null | [C:1]1([CH2:7][O:8][C:9](=[O:25])[NH:10][CH2:11][CH2:12][CH2:13][NH:14][CH2:15][CH2:16][P:17]([O:22][CH2:23][CH3:24])([O:19][CH2:20][CH3:21])=[O:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:26]([O:28][C:29]1[C:30](=O)[C:31](=[O:36])[C:32]=1[O:33]CC)[CH3:27]>C(O)C>[C:1]1([CH2:7][O:8][C:9](=[O:25])[NH:10][CH2:11][CH2:12][CH2:13][N:14]([CH2:15][CH2:16][P:17]([O:19][CH2:20][CH3:21])([O:22][CH2:23][CH3:24])=[O:18])[C:30]2[C:31](=[O:36])[C:32](=[O:33])[C:29]=2[O:28][CH2:26][CH3:27])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1 | null | CCO | null | null | null | null | 88.9 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
769,727 | Cl | null | null | null | ord_dataset-8214eb8444a44dc2900ccb42dbeff15e | 2007-01-01T00:05:00 | true | By using a method similar to the method of Example 532, combine 2-(2-nitro-phenylamino)-benzo[b]thiophene-3-carbonitrile (5.0 g, 17.0 mmol) and Tin(II) chloride (9.65 g, 51.0 mmol) in a mixed solvent of EtOH (50 mL) and 5.0 N HCl (50 mL), heat the suspension to reflux for 3 hours, cool to RT. The title compound 4.65 g (yield 91%) is obtained as a yellow solid by suction filtration. Mass spectrum: ACPI (m/e): 266.0 ((M+1-HCl); 1H NMR (300 MHz, DMSO-d6) ppm: 11.7 (br, 1H), 10.00 (br, 1H), 9.10 (br, 2H), 7.90–7.85 (m, 1H), 7.72–7.65 (m, 1H), 7.48–7.38 (m, 1H), 7.35–7.28 (m, 1H), 7.22–6.98 (m, 4H). | NC1=Nc2ccccc2Nc2sc3ccccc3c21 | null | N#Cc1c(Nc2ccccc2[N+](=O)[O-])sc2ccccc12 | Cl[Sn]Cl | null | [N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]1[S:15][C:14]2[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=2[C:12]=1[C:20]#[N:21])([O-])=O.[Sn](Cl)[Cl:23].Cl>CCO>[ClH:23].[CH:16]1[C:14]2[S:15][C:11]3[NH:10][C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:1]=[C:20]([NH2:21])[C:12]=3[C:13]=2[CH:19]=[CH:18][CH:17]=1 | null | CCO | null | null | 25 | null | 90.6 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
311,996 | null | null | null | null | ord_dataset-04982f13ed08448d93df6794846500f3 | 1995-01-01T00:06:00 | true | In 30.0 ml of tetrahydrofuran (THF), 10.0 g (45.42 mmol) of 2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z)fluoromethoxyiminoacetic acid were stirred at room temperature to completely dissolve the latter in the former, followed by cooling to -12° C. Added dropwise to the reaction mixture was a chlorinating reagent, which had been prepared beforehand by gradually adding 7.65 g (49.89 mmol) of phosphorus oxychloride at 5° C. into a mixture of 20 ml of THF and 3.7 g (49.93 mmol) of N,N-dimethylformamide (DMF) and then reacting them for 30 minutes. Subsequent to their reaction for 60 minutes with the temperature maintained at -15° C., the reaction mixture was poured into 150 ml of ice water and was then stirred for 20 minutes to precipitate crystals. The crystals were collected by filtration, washed twice with 15 ml aliquots of ice water and then, under reduced pressure, dried, whereby the title compound was obtained. Yield: 8.50 g (77.9%). Purity: 95.7%. | Nc1nc(/C(=N/OCF)C(=O)Cl)ns1 | null | O=P(Cl)(Cl)Cl | Nc1nc(/C(=N/OCF)C(=O)O)ns1 | null | [NH2:1][C:2]1[S:6][N:5]=[C:4](/[C:7](=[N:11]/[O:12][CH2:13][F:14])/[C:8](O)=[O:9])[N:3]=1.P(Cl)(Cl)([Cl:17])=O.CN(C)C=O>O1CCCC1>[NH2:1][C:2]1[S:6][N:5]=[C:4](/[C:7](=[N:11]/[O:12][CH2:13][F:14])/[C:8]([Cl:17])=[O:9])[N:3]=1 | 0.33 | CN(C)C=O | C1CCOC1 | null | -12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
382,289 | null | null | null | null | ord_dataset-f367d8d2baac490b9204609a79420961 | 1997-01-01T00:11:00 | true | In an oven-dried round bottomed flask was added L-proline, 1-[2-(3,4,5-trimethoxyphenyl)-2-oxoethyl] 2-(4-aminophenyl)ethylamide (100 mg, 0.23 mmol), and tetrahydrofuran (5 mL). The solution was stirred at 22° C., and treated with pyridine (0.037 mL, 0.45 mmol, 2.0 eq) followed by acetyl chloride (0.024 mL, 0.34 mmol, 1.5 eq). The reaction mixture was allowed to stir for one hour. The solvent was removed in vacuo and the residue partitioned between EtOAc (50 mL) and sat. NaHCO3 (50 mL). The organic layer was washed with sat. aq. NaCl, dried (MgSO4) and concentrated to an oil. The oil was purified by flash chromatography to provide 70 mg of L-proline, 1-[2-(3,4,5-trimethoxyphenyl)-2-oxoethyl] 2-(4-(N-acetyl)aminophenyl)ethylamide as a foam. | COc1cc(C(=O)CC(Cc2ccc(NC(C)=O)cc2)NC(=O)[C@@H]2CCCN2)cc(OC)c1OC | null | COc1cc(C(=O)CC(Cc2ccc(N)cc2)NC(=O)[C@@H]2CCCN2)cc(OC)c1OC | CC(=O)Cl | null | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13](=[O:32])[CH2:14][CH:15]([NH:24][C:25](=[O:31])[C@@H:26]2[CH2:30][CH2:29][CH2:28][NH:27]2)[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].N1C=CC=CC=1.[C:39](Cl)(=[O:41])[CH3:40]>O1CCCC1>[CH3:12][O:11][C:7]1[CH:6]=[C:5]([C:13](=[O:32])[CH2:14][CH:15]([NH:24][C:25](=[O:31])[C@@H:26]2[CH2:30][CH2:29][CH2:28][NH:27]2)[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:39](=[O:41])[CH3:40])=[CH:19][CH:18]=2)[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH3:10] | null | C1CCOC1 | c1ccncc1 | null | 22 | null | 62.9 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
424,146 | null | null | null | null | ord_dataset-1a231de00bfe4443b547e1f03885ed41 | 1999-01-01T00:01:00 | true | 2-(3-tert-Butoxycarbonylaminomethylpyrrolidin-1-yl)ethylamine (1 g) was dissolved in methylene chloride (10 ml) and a solution of methyl isocyanate (0.24 ml) in methylene chloride was dropwise added under ice-cooling. The mixture was stirred at room temperature for 1 hr, and the reaction mixture was concentrated under reduced pressure to give 1-(2-(3-methylureido)ethyl)-3-tert-butoxycarbonylaminomethylpyrrolidine. | CNC(=O)NCCN1CCC(CNC(=O)OC(C)(C)C)C1 | null | CN=C=O | CC(C)(C)OC(=O)NCC1CCN(CCN)C1 | null | [C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][NH2:17])[CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:18][N:19]=[C:20]=[O:21]>C(Cl)Cl>[CH3:18][NH:19][C:20](=[O:21])[NH:17][CH2:16][CH2:15][N:12]1[CH2:13][CH2:14][CH:10]([CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:11]1 | 1 | 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 |
900,401 | null | null | null | null | ord_dataset-de6bce51790e4004a27e1a8f2bcc7ded | 2009-01-01T00:08:00 | true | The title compound was prepared from [4-(3-amino-phenyl)-8-chloro-quinolin-3-yl]-phenyl-methanone and (3-formyl-phenyl)-acetic acid methyl ester according to the procedure of Example 66. MS (ESI) m/z 507. | O=C(O)Cc1cccc(CNc2cccc(-c3c(C(=O)c4ccccc4)cnc4c(Cl)cccc34)c2)c1 | null | Nc1cccc(-c2c(C(=O)c3ccccc3)cnc3c(Cl)cccc23)c1 | COC(=O)Cc1cccc(C=O)c1 | null | [NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[C:13]([Cl:18])[CH:14]=[CH:15][CH:16]=3)[N:11]=[CH:10][C:9]=2[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:20])[CH:5]=[CH:6][CH:7]=1.C[O:28][C:29](=[O:39])[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([CH:37]=O)[CH:32]=1>>[C:19]([C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:8]=1[C:4]1[CH:3]=[C:2]([NH:1][CH2:37][C:33]3[CH:32]=[C:31]([CH2:30][C:29]([OH:39])=[O:28])[CH:36]=[CH:35][CH:34]=3)[CH:7]=[CH:6][CH:5]=1)=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])(=[O:20])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH: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 |
691,665 | [Na+] | [OH-] | null | null | ord_dataset-6214af00a7eb47f3887ef21a94320a7e | 2005-01-01T00:11:00 | true | Sodium hydroxide (1.2 g, 3.0 mmole) was added to a solution of 4-(1,2-dimethyl-imidazol-5-yl)-2-(4-acetamidoanilino)pyrimidine (Example 164; 1.25 g, 3.88 mmole) in isopropanol (12 mL) and water (0.5 mL) and the mixture heated under reflux for 90 minutes. The mixture was allowed to cool and was partitioned between saturated aqueous sodium hydrogen carbonate solution and EtOAc. The organic layer was separated and the volatiles evaporated. The residue was purified by column chromatography on silica gel eluting with DCM/7M methanolic ammonia (96:4) to give the title compound (0.75 g, 69%) as a brown solid. NMR: 2.33 (s, 3H), 3.85 (s, 3H), 4.75 (brs, 2H), 6.51 (d, 2H), 6.92 (d, 1H), 7.22 (d, 2H), 7.51 (s, 1H), 8.22 (d, 1H), 8.90 (s, 1H); m/z 281. | Cc1ncc(-c2ccnc(Nc3ccc(N)cc3)n2)n1C | null | CC(=O)Nc1ccc(Nc2nccc(-c3cnc(C)n3C)n2)cc1 | null | null | [OH-].[Na+].[CH3:3][N:4]1[C:8]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([NH:22]C(=O)C)=[CH:18][CH:17]=3)[N:10]=2)=[CH:7][N:6]=[C:5]1[CH3:26]>C(O)(C)C.O>[CH3:3][N:4]1[C:8]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=3)[N:10]=2)=[CH:7][N:6]=[C:5]1[CH3:26] | null | CC(C)O | O | 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 | null |
1,580,458 | [Br-] | null | null | null | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | 2015-01-01T00:05:00 | true | To a solution of 1-(3-bromophenyl)-5-[(4-methoxybenzyl)oxy]-4-oxo-1,4-dihydropyridine-2-carbaldehyde (3.0 g, 7.25 mmol), in dry THF (50 mL) was added MeMgBr (7.25 mL of a 3 M solution in THF, 21.8 mmol) dropwise at −30° C., and the reaction mixture was stirred at −30° C. then warmed to room temperature and stirred for another 2 h. The reaction mixture was cooled to 0° C., 2 mL water was added, and the mixture was diluted with ethyl acetate. The layers were separated, and the organic fraction was dried (MgSO4), concentrated under reduced pressure, and purified by Prep-HPLC to give 1.8 g (58%) of 1-(3-bromophenyl)-2-(1-hydroxyethyl)-5-[(4-methoxybenzyl)oxy]pyridin-4(1H)-one. Chiral resolution of 12.0 g 1-(3-bromophenyl)-2-(1-hydroxyethyl)-5-[(4-methoxybenzyl)oxy]pyridin-4(1H)-one was accomplished by SFC of racemic material using a Chiral Technologies ChiralPak AD-H column (25% MeOH in CO2, 3 cm diameter×25 cm length, 70 mL/min flow, 200 mg per injection), and afforded (80%) of the first eluting enantiomer and (79%) of the second eluting enantiomer. 1H-NMR (CD3OD, 400 MHz) δ 7.76 (d, J=8.0 Hz, 1H), 7.64 (s, 1H), 7.51-7.41(m, 2H), 7.38-7.35 (m, 2H), 7.33-7.31 (m, 2H), 6.88-6.86 (m, 2H), 6.76 (s, 1H), 4.95 (s, 2H), 4.39-4.34 (m, 1H), 3.76 (s, 3H), 1.26 (d, J=6.0 Hz, 2H). MS (ESI) m/z (M+H)+ 430.1/432.1. | COc1ccc(COc2cn(-c3cccc(Br)c3)c(C(C)O)cc2=O)cc1 | null | COc1ccc(COc2cn(-c3cccc(Br)c3)c(C=O)cc2=O)cc1 | C[Mg+] | null | [Br:1][C:2]1[CH:3]=[C:4]([N:8]2[CH:13]=[C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[C:11](=[O:24])[CH:10]=[C:9]2[CH:25]=[O:26])[CH:5]=[CH:6][CH:7]=1.[CH3:27][Mg+].[Br-].O>C1COCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[CH:13]=[C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[C:11](=[O:24])[CH:10]=[C:9]2[CH:25]([OH:26])[CH3:27])[CH:5]=[CH:6][CH:7]=1 | null | O | C1CCOC1 | CCOC(C)=O | -30 | 58 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
330,938 | [BH4-] | [Na+] | null | null | ord_dataset-2c460e2ef9934444aaf26fec1f75741f | 1996-01-01T00:05:00 | true | To a solution of 1-{4-[2-(2-methylphenyl)benzoylamino]benzoyl}-2,3,4,5-tetrahydro-1H-1-benzazepin-5-one (620 mg) in methanol (20 ml) was added sodium borohydride (49.4 mg) and the mixture was stirred at ambient temperature for 4 hours. The mixture was diluted with chloroform and the solution was washed with water and brine, and dried over magnesium sulfate. The solvent was evaporated in vacuo to give a syrup and the residue was purified by silica gel column (30g, 1% methanol in chloroform) to give 5-hydroxy-1-{4-[2-(2-methylphenyl)benzoylamino]benzoyl}-2,3,4,5-tetrahydro-1H-1-benzazepine (580 mg). | Cc1ccccc1-c1ccccc1C(=O)Nc1ccc(C(=O)N2CCCC(O)c3ccccc32)cc1 | null | Cc1ccccc1-c1ccccc1C(=O)Nc1ccc(C(=O)N2CCCC(=O)c3ccccc32)cc1 | null | null | [CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:36]=[CH:35][CH:34]=[CH:33][C:9]=1[C:10]([NH:12][C:13]1[CH:32]=[CH:31][C:16]([C:17]([N:19]2[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[C:23](=[O:30])[CH2:22][CH2:21][CH2:20]2)=[O:18])=[CH:15][CH:14]=1)=[O:11].[BH4-].[Na+]>CO.C(Cl)(Cl)Cl>[OH:30][CH:23]1[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[N:19]([C:17](=[O:18])[C:16]2[CH:15]=[CH:14][C:13]([NH:12][C:10](=[O:11])[C:9]3[CH:33]=[CH:34][CH:35]=[CH:36][C:8]=3[C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[CH3:1])=[CH:32][CH:31]=2)[CH2:20][CH2:21][CH2:22]1 | 4 | ClC(Cl)Cl | CO | null | 25 | null | 93.2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,578,869 | [K+] | null | null | null | ord_dataset-9741bb5fd93044078df2a45f45733054 | 2015-01-01T00:04:00 | true | 15.0 g (124.4 mmol) of 2-methylbutyryl chloride were dissolved in 150 ml of abs. THF and cooled to 0° C., and 114 ml (114 mmol) of a 1 M solution of potassium tert-butylate in THF were added dropwise. After the addition had ended, the mixture was stirred at 0° C. for 1 h and then at RT for h, and about half of the solvent was then removed under reduced pressure. After addition of diethyl ether, sat. sodium bicarbonate solution was added dropwise with vigorous stirring. After phase separation, the aqueous phase was extracted with diethyl ether, and the combined organic phases were washed with sat. sodium carbonate solution, dried over sodium sulphate and concentrated under reduced pressure. The crude product was purified by vacuum distillation (19 mm Hg, 40-45° C.). This gave a total of 6.35 g of the target product (32.3% of theory). | CCC(C)C(=O)OC(C)(C)C | null | CC(C)(C)[O-] | CCC(C)C(=O)Cl | null | [CH3:1][CH:2]([CH2:6][CH3:7])[C:3](Cl)=[O:4].[CH3:8][C:9]([O-:12])([CH3:11])[CH3:10].[K+]>C1COCC1>[CH3:1][CH:2]([CH2:6][CH3:7])[C:3]([O:12][C:9]([CH3:11])([CH3:10])[CH3:8])=[O:4] | 1 | C1CCOC1 | null | null | 0 | 32.3 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
882,129 | O=C([O-])[O-] | [K+] | null | null | ord_dataset-3592bd645cd143ee8274cd0d834ae581 | 2009-01-01T00:05:00 | true | A mixture of 0.48 g of 3-acetoxy-2-(methoxycarbonyl)methylthiopyridine, 0.15 g of potassium carbonate, and 3 ml of methanol was stirred at room temperature for 3 hours. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated. The residue was subjected to silica gel column chromatography to give 0.26 g of 3-hydroxy-2-(methoxycarbonyl)methylthiopyridine. | COC(=O)CSc1ncccc1O | null | COC(=O)CSc1ncccc1OC(C)=O | null | null | C([O:4][C:5]1[C:6]([S:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[N:7][CH:8]=[CH:9][CH:10]=1)(=O)C.C(=O)([O-])[O-].[K+].[K+].CO>O>[OH:4][C:5]1[C:6]([S:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[N:7][CH:8]=[CH:9][CH:10]=1 | 3 | CO | O | null | 25 | 65.6 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,601,926 | Cl | null | null | null | ord_dataset-e8c6a25568b64529b960953990e6921f | 2015-01-01T00:06:00 | true | 4-((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(2-(6-(carboxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl)ethylcarbamoyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-yloxy)-2,2-dimethyl-4-oxobutanoic acid (Example 80, 0.3 g) was taken in MeOH (3 ml) and cooled the contents to 0° C. then Aq HCl (0.5 ml) was added and the contents were stirred for 6 hours at room temperature. After completion of the reaction (monitored by TLC), the reaction mixture was evaporated under reduced pressure. The residue was taken in water and extracted with DCM, the organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography using 5% methanol in DCM as eluent to furnish the title compound (0.08 g) as a white solid. 1H NMR (300 MHz, CDCl3): 0.57-0.97 (m, 19H); 1.18-1.21 (m, 8H); 1.25-1.41 (m, 12H); 1.49-1.62 (m, 8H); 1.65-1.82 (m, 10H); 1.85-1.98 (m, 4H); 2.56-2.69 (m, 2H); 2.88-3.06 (m, 3H); 3.29-3.38 (m, 1H); 3.89-3.90 (m, 1H); 4.44-4.47 (m, 1H); 4.56 (s, 1H); 4.71 (s, 1H); Mass: 744 [M+1]. | C=C(C)[C@@H]1CC[C@]2(C(=O)NCCC(O)CC(O)CC(=O)O)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](OC(=O)CC(C)(C)C(=O)O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12 | null | C=C(C)[C@@H]1CC[C@]2(C(=O)NCCC3CC(CC(=O)OC(C)(C)C)OC(C)(C)O3)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](OC(=O)CC(C)(C)C(=O)O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12 | null | null | C([O:5][C:6](=[O:60])[CH2:7][CH:8]1[O:13]C(C)(C)[O:11][CH:10]([CH2:16][CH2:17][NH:18][C:19]([C@:21]23[CH2:56][CH2:55][C@@H:54]([C:57]([CH3:59])=[CH2:58])[C@@H:22]2[C@@H:23]2[C@@:36]([CH3:39])([CH2:37][CH2:38]3)[C@@:35]3([CH3:40])[C@@H:26]([C@:27]4([CH3:53])[C@@H:32]([CH2:33][CH2:34]3)[C:31]([CH3:42])([CH3:41])[C@@H:30]([O:43][C:44](=[O:52])[CH2:45][C:46]([CH3:51])([CH3:50])[C:47]([OH:49])=[O:48])[CH2:29][CH2:28]4)[CH2:25][CH2:24]2)=[O:20])[CH2:9]1)(C)(C)C.Cl>CO>[C:47]([C:46]([CH3:51])([CH3:50])[CH2:45][C:44]([O:43][C@H:30]1[CH2:29][CH2:28][C@@:27]2([CH3:53])[C@@H:32]([CH2:33][CH2:34][C@:35]3([CH3:40])[C@@H:26]2[CH2:25][CH2:24][C@H:23]2[C@@:36]3([CH3:39])[CH2:37][CH2:38][C@@:21]3([C:19]([NH:18][CH2:17][CH2:16][CH:10]([OH:11])[CH2:9][CH:8]([OH:13])[CH2:7][C:6]([OH:60])=[O:5])=[O:20])[CH2:56][CH2:55][C@@H:54]([C:57]([CH3:59])=[CH2:58])[C@@H:22]32)[C:31]1([CH3:42])[CH3:41])=[O:52])([OH:49])=[O:48] | 6 | CO | null | null | 0 | null | 30.1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
996,510 | O=C([O-])[O-] | [Cs+] | null | null | ord_dataset-b6d8835b0c934476a36e6149e7597487 | 2010-01-01T00:09:00 | true | To a solution of 6-Bromo-2-(2,4-dichloro-benzoyl)-benzofuran-3-one (3.30 g, 8.55 mmol) in acetone (50 mL) was added dimethyl sulfate (1.19 g, 9.40 mmol) and cesium carbonate (4.18 g, 12.82 mmol). The resulting mixture was heated at 50 deg for 6 hours is at which time the reaction mixture was concentrated via rotary evaporation. The resulting mixture was taken up in EtOAc and washed twice with water and one time with a saturated sodium carbonate solution. The organic portion was dried over MgSO4 and then filtered and concentrated. The resultant oil was purified via column chromatography (10% MeOH/Dichloromethane) to provide the title compound (950 mg, 28%). 1H-NMR (CDCl3): δ 8.03 (d, 1H), 7.65 (d, 1H), 7.46 (m, 2H), 7.35 (m, 2H), 2.46 (s, 3H). | COc1c(C(=O)c2ccc(Cl)cc2Cl)oc2cc(Br)ccc12 | null | O=C(c1ccc(Cl)cc1Cl)C1Oc2cc(Br)ccc2C1=O | COS(=O)(=O)OC | null | [Br:1][C:2]1[CH:21]=[CH:20][C:5]2[C:6](=[O:19])[CH:7]([C:9](=[O:18])[C:10]3[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=3[Cl:17])[O:8][C:4]=2[CH:3]=1.S(OC)(O[CH3:26])(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[Br:1][C:2]1[CH:21]=[CH:20][C:5]2[C:6]([O:19][CH3:26])=[C:7]([C:9]([C:10]3[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=3[Cl:17])=[O:18])[O:8][C:4]=2[CH:3]=1 | null | CC(C)=O | null | null | null | 27.8 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,186,845 | CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C | F[P-](F)(F)(F)(F)F | null | null | ord_dataset-9cd817a75dfc4fe7ad19d4232772d5ff | 2012-01-01T00:07:00 | true | To a vial containing a solution of 2-(2,6-dichloro-phenyl)-3H-benzoimidazol-5-ylamine in dioxane (0.2 M, 0.10 mL) was added DIPEA (0.5 M in toluene, 0.050 mL) and acetic acid (0.2 M in toluene, 0.12 mL), followed by BOP reagent (0.2 M in DMF, 0.15 mL). After overnight at ambient temperature, the mixture was then diluted by MeOH and the whole was loaded onto a solid phase extraction (SPE) cartridge that contained strong cation exchange (SCX) (1 g media in 6 mL cartridge, United Chemical Technology). Wash-to-waste (5 mL MeOH) was followed by elute-to-collect (5 mL 20:2:1 ethyl acetate-MeOH-Et3N) and, after evaporation of volatiles, the crude was further purified by silica gel column chromatography to N-[2-(2-Chloro-phenyl)-3H-benzoimidazol-5-yl]-acetamide: MS (m/z) 320.02 (M+1). | CC(=O)Nc1ccc2nc(-c3ccccc3Cl)[nH]c2c1 | null | Nc1ccc2nc(-c3c(Cl)cccc3Cl)[nH]c2c1 | CC(=O)O | null | Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[NH:10][C:11]2[CH:17]=[C:16]([NH2:18])[CH:15]=[CH:14][C:12]=2[N:13]=1.CCN(C(C)C)C(C)C.[C:28](O)(=[O:30])[CH3:29].CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F>O1CCOCC1.CO>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[CH:2][C:3]=1[C:9]1[NH:10][C:11]2[CH:17]=[C:16]([NH:18][C:28](=[O:30])[CH3:29])[CH:15]=[CH:14][C:12]=2[N:13]=1 | 8 | CCN(C(C)C)C(C)C | CO | 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 |
422,390 | null | null | null | null | ord_dataset-1a231de00bfe4443b547e1f03885ed41 | 1999-01-01T00:01:00 | true | substituting 1-(2-(2,2,2-trifluoroethoxy)phenyl]piperazine and 1-biphenyl-3-ylmethyl-3-(3-chloropropyl)-5-methyl-2,4(1H,3H)-pyrimidinedione gave 1-biphenyl-3-ylmethyl-3-(3-{4-[2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl}-propyl)-5-methyl-2,4(1H,3H)-pyrimidinedione hydrochloride, m.p. 93°-94° C.; Anal.: Calcd. for C33H35F3N4O3.HCl: C, 63.06; H, 5.77; N, 8.92%; Found: C, 61.66; H, 5.90; N, 8.50%; | Cc1cn(Cc2cccc(-c3ccccc3)c2)c(=O)n(CCCN2CCN(c3ccccc3OCC(F)(F)F)CC2)c1=O | Cl | FC(F)(F)COc1ccccc1N1CCNCC1 | Cc1cn(Cc2cccc(-c3ccccc3)c2)c(=O)n(CCCCl)c1=O | null | [F:1][C:2]([F:18])([F:17])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.[C:19]1([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][N:26]2[CH:31]=[C:30]([CH3:32])[C:29](=[O:33])[N:28]([CH2:34][CH2:35][CH2:36][Cl:37])[C:27]2=[O:38])[CH:20]=1>>[ClH:37].[C:19]1([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][N:26]2[CH:31]=[C:30]([CH3:32])[C:29](=[O:33])[N:28]([CH2:34][CH2:35][CH2:36][N:14]3[CH2:15][CH2:16][N:11]([C:6]4[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=4[O:4][CH2:3][C:2]([F:1])([F:17])[F:18])[CH2:12][CH2:13]3)[C:27]2=[O:38])[CH:20]=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 |
953,071 | [H-] | [Na+] | null | null | ord_dataset-3feb2a95f66e4706a4a50c977ccd9bf8 | 2010-01-01T00:04:00 | true | 22.5 ml (113 mmol) of triethyl phosphono-acetate are dissolved in 100 ml of THF. 4.5 g (113 mmol) of 60% sodium hydride are then added, and the medium is stirred for 30 minutes at ambient temperature. A solution of 20 g (75.6 mmol) of 3-(tert-butyldimethylsilanyloxy)propan-1-one in 100 ml of THF is then added drop by drop. The medium is stirred for 6 hours, then treated with water and extracted with ethyl acetate. The residue obtained is purified by chromatography on silica gel (eluent ethyl acetate 10-heptane 90). A yellow oil is obtained (m=7.6 g; Y=30%). | CCOC(=O)/C=C(\CC)c1cccc(O[Si](C)(C)C(C)(C)C)c1 | null | O | CC(C)(C)[Si](C)(C)OCCC=O | C1CCOC1 | [H-].[Na+].[Si:3]([O:10][CH2:11][CH2:12][CH:13]=O)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4].[OH2:15].[CH2:16]1[CH2:20][O:19][CH2:18][CH2:17]1>>[Si:3]([O:10][C:11]1[CH:12]=[C:13](/[C:11](/[CH2:12][CH3:13])=[CH:17]/[C:18]([O:19][CH2:20][CH3:16])=[O:15])[CH:7]=[CH:6][CH:8]=1)([C:6]([CH3:7])([CH3:8])[CH3:9])([CH3:4])[CH3:5] | 0.5 | null | 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 |
74,723 | C[C@H]1CC(=O)C=C2CC[C@H]3[C@@H]4CC[C@H](O)[C@@]4(C)CC[C@@H]3[C@]21CO | null | null | null | ord_dataset-b9d8ddf9c2884d40859b6b5f24815a7d | 1980-01-01T00:12:00 | true | Substituting 17β,19-dihydroxy-1α,17α-dimethyl-4-androsten-3-one and 17β,19-dihydroxy-4-methyl-4-androsten-3-one in lieu of the 17β,19-dihydroxy-1α-methyl-4-androsten-3-one above, results in the preparation of 1α,17α-dimethyl-4-androstene-17β,19-diol and 4-methyl-4-androsten-17β,19-diol, respectively. | CC1=C2CC[C@@H]3[C@H](CC[C@]4(C)[C@@H](O)CC[C@@H]34)[C@@]2(CO)CCC1 | null | CC1=C2CC[C@@H]3[C@H](CC[C@]4(C)[C@@H](O)CC[C@@H]34)[C@@]2(CO)CCC1=O | null | null | [OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:19]([CH2:20][CH2:21][C@:3]12[CH3:4])[C@:16]1([CH2:17][OH:18])[C:11](=[C:12]([CH3:23])[C:13](=O)[CH2:14][CH2:15]1)[CH2:10][CH2:9]3.O[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@]12C)[C@]1(CO)C(=CC(=O)C[C@@H]1C)CC3>>[CH3:23][C:12]1[CH2:13][CH2:14][CH2:15][C@@:16]2([CH2:17][OH:18])[C:11]=1[CH2:10][CH2:9][C@@H:8]1[C@@H:19]2[CH2:20][CH2:21][C@@:3]2([CH3:4])[C@H:5]1[CH2:6][CH2:7][C@@H:2]2[OH: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 |
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