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 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
1,098,520 | Cl | null | null | null | ord_dataset-af85e6f81c2d49f08086afd6d9e6959c | 2011-01-01T00:10:00 | true | A mixture of 4-oxo-cyclohexanecarboxylic acid (4.05 g, 28.5 mmol) and phenylhydrazine hydrochloride (4.12 g, 28.5 mmol) in EtOH (200 ml) is stirred at reflux for 3 h. Then, the solvent is evaporated and the residue is dissolved in boiling toluene. Precipitating ammonium chloride is filtered off and the clear filtrate is cooled to rt. The resulting precipitate is filtered and tried under high vacuum to give pure subtitle compound as a white solid (5.16 g) in 84% yield. tR (LC-3) 2.21 min; ESI-MS (positive ion): m/z 216.30 [M+H]+(calcd 215.09 for C13H13NO2). 1H-NMR (CDCl3): 2.01 (m, 1H); 2.28 (m, 1H); 2.83 (m, 4H); 3.04 (dd, J=14.8 Hz, 4.7 Hz, 1H); 7.02 (m, 2H); 7.19 (d, J=7.2 Hz, 1H); 7.38 (d, J=7.0 Hz, 1H); 7.63 (s br, 1H). | O=C(O)C1CCc2[nH]c3ccccc3c2C1 | null | O=C1CCC(C(=O)O)CC1 | NNc1ccccc1 | null | O=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]([OH:10])=[O:9])[CH2:4][CH2:3]1.Cl.[C:12]1([NH:18]N)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CCO>[CH2:7]1[C:2]2[NH:18][C:12]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:3]=2[CH2:4][CH:5]([C:8]([OH:10])=[O:9])[CH2:6]1 | null | CCO | null | null | 25 | 84.1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
870,001 | O=C1CCc2cccc(Nc3ncc(-c4ccc(C(F)(F)F)cc4)o3)c2C1 | null | null | null | ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | 2009-01-01T00:03:00 | true | The title compound was prepared using the procedure as described in Example 2, substituting the product of Example 8C for the product of Example 1I. 1H NMR (DMSO-d6) 69.17 (s, 1H), 7.43-7.57 (m, 6H), 7.10 (t, 1H, J=7.3 Hz), 6.81 (d, 1H, J=6.8 Hz), 4.80 (d, 1H, J=3.9 Hz), 3.90 (m, 1H), 2.68-2.96 (m, 4H), 1.82 (m, 1H), 1.60 (m, 1H); MS (ESI+) m/z 385/387 (M+H, 79Br/81Br). | OC1CCc2cccc(Nc3ncc(-c4ccc(Br)cc4)o3)c2C1 | null | O=C1CCc2cccc(Nc3ncc(-c4ccc(Br)cc4)o3)c2C1 | null | null | [Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([NH:13][C:14]3[CH:15]=[CH:16][CH:17]=[C:18]4[C:23]=3[CH2:22][C:21](=[O:24])[CH2:20][CH2:19]4)=[N:10][CH:9]=2)=[CH:4][CH:3]=1.FC(F)(F)C1C=CC(C2OC(NC3C=CC=C4C=3CC(=O)CC4)=NC=2)=CC=1>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([NH:13][C:14]3[CH:15]=[CH:16][CH:17]=[C:18]4[C:23]=3[CH2:22][CH:21]([OH:24])[CH2:20][CH2:19]4)=[N:10][CH:9]=2)=[CH:4][CH:3]=1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
910,577 | Cl | [Li+] | [OH-] | null | ord_dataset-c663259b80f947e2a8923796fb0e9a6b | 2009-01-01T00:10:00 | true | To a solution of methyl [1-((3S)-3-isopropyl-3-{[3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl]carbonyl}cyclopentyl)piperidin-4-yl]acetate (470 mgs, 0.92 mmol) in methanol (5 ml) was added 2N Lithium Hydroxide solution (1.8 ml, 3.7 mmol), the reaction was then stirred overnight at room temperature. The reaction was neutralized to pH=5 using 3N HCl. The crude was purified on reverse phase HPLC using 5%-100% ACN/H2O to yield [1-((3S)-3-{[3-(1,1-difluoroethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl]carbonyl}-3-isopropylcyclopentyl)piperidin-4-yl]acetic acid (320 mgs, 91%), LC-MS 482 (M++1). | CC(C)[C@]1(C(=O)N2CCc3ncc(C(C)(F)F)cc3C2)CCC(N2CCC(CC(=O)O)CC2)C1 | null | COC(=O)CC1CCN(C2CC[C@@](C(=O)N3CCc4ncc(C(F)(F)F)cc4C3)(C(C)C)C2)CC1 | CO | null | [CH:1]([C@:4]1([C:20]([N:22]2[CH2:31][CH2:30][C:29]3[N:28]=[CH:27][C:26]([C:32]([F:35])(F)[F:33])=[CH:25][C:24]=3[CH2:23]2)=[O:21])[CH2:8][CH2:7][CH:6]([N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][C:16]([O:18]C)=[O:17])[CH2:11][CH2:10]2)[CH2:5]1)([CH3:3])[CH3:2].[OH-].[Li+].Cl.[CH3:39]O>>[F:35][C:32]([C:26]1[CH:27]=[N:28][C:29]2[CH2:30][CH2:31][N:22]([C:20]([C@@:4]3([CH:1]([CH3:2])[CH3:3])[CH2:8][CH2:7][CH:6]([N:9]4[CH2:10][CH2:11][CH:12]([CH2:15][C:16]([OH:18])=[O:17])[CH2:13][CH2:14]4)[CH2:5]3)=[O:21])[CH2:23][C:24]=2[CH:25]=1)([F:33])[CH3:39] | 8 | null | null | null | 25 | null | 91 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,516,828 | CS(N)(=O)=O | null | null | null | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | 2014-01-01T00:12:00 | true | Compound 10h was synthesized by a procedure similar to that described for (R)-10a using (Z)-tert-butyl(1-(naphthalen-1-yl)prop-1-enyloxy)dimethylsilane, (9h, 4.58 g, 0.015 mol), AD-mix-β (21.4 g), and CH3SO2NH2 (1.5 g, 0.0158 mol) in tert-butyl alcohol-water (60 mL:60 mL). The reaction was quenched with sodium sulfite (15.3 g). After purification by column chromatography on silica gel, 1.15 g (38%) of the title product was isolated plus 2.1 g of starting olefin was recovered, raising the effective yield to 70%: [α]20D +140.2° (c 3.2, CHCl3); 1H NMR (CDCl3) δ 8.51-8.46 (m, 1H), 8.04 (d, 1H, J=8.3 Hz), 7.93-7.87 (m, 1H), 7.80-7.75 (m, 1H), 7.66-7.48 (m, 3H), 5.30-5.17 (m, 1H), 3.96 (d, 111, J=5.8 Hz), 1.36 (d, 3H, J=7.1 Hz); 13C NMR (CDCl3) δ 205.7, 134.1, 133.5, 132.5, 130.7, 128.7, 128.4, 127.7, 126.9, 125.5, 124.4, 71.2, 21.3; LCMS (ESI) m/z 201.2 [(M+H)+, M=C13H12O2]. | C[C@@H](O)C(=O)c1cccc2ccccc12 | null | C/C=C(\O[Si](C)(C)C(C)(C)C)c1cccc2ccccc12 | CC[C@H]1CN2CC[C@H]1C[C@@H]2[C@@H](Oc1nnc(O[C@@H](c2ccnc3ccc(OC)cc23)[C@H]2C[C@@H]3CCN2C[C@@H]3CC)c2ccccc12)c1ccnc2ccc(OC)cc12 | null | C([Si]([O:8]/[C:9](/[C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1)=[CH:10]\[CH3:11])(C)C)(C)(C)C.CC[C@@H]1[C@@H]2C[C@H]([C@@H](OC3C4C(=CC=CC=4)C(O[C@@H](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C([O:43]C)C=C4)N(CC2)C1.CS(N)(=O)=O>C(O)(C)(C)C.O>[OH:43][C@H:10]([CH3:11])[C:9]([C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1)=[O:8] | null | CC(C)(C)O | O | null | null | null | 38.3 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,271,236 | null | null | null | null | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | 2013-01-01T00:03:00 | true | The title compound, MS: m/e=374.1 (M+H+), was prepared in accordance with the general method of example 1 from 2,6-dichloroquinoline, 2-methoxybenzylamine and (1-methyl-1H-imidazol-5-yl)methylamine. | COc1ccccc1CNc1ccc2cc(NCc3cncn3C)ccc2n1 | null | Clc1ccc2nc(Cl)ccc2c1 | Cn1cncc1CN | COc1ccccc1CN | Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7](Cl)[CH:8]=2)[N:3]=1.[CH3:13][O:14][C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH2:17][NH2:18].[CH3:23][N:24]1[C:28]([CH2:29][NH2:30])=[CH:27][N:26]=[CH:25]1>>[CH3:13][O:14][C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH2:17][NH:18][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH:30][CH2:29][C:28]3[N:24]([CH3:23])[CH:25]=[N:26][CH:27]=3)[CH:8]=2)[N:3]=1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
849,092 | null | null | null | null | ord_dataset-171b840ae6e84e45bab43b987d09f5c7 | 2008-01-01T00:11:00 | true | A mixture of 2-amino-4-(2-chlorophenyl)-thiophene-3-carboxylic acid ethyl ester (2 mmol, Example 8, Part B) and phthalic anhydride (2.2 mmol) in glacial acetic acid (20 mL) is heated at reflux overnight. After cooling to room temperature, the acetic acid is removed in vacuo and the residue triturated with petroleum ether. The crude product is collected by filtration, suspended in acetyl chloride (5 mL), and heated to reflux for one hour. After removing the solvent in vacuo, the residue is dissolved in ethyl acetate (30 mL), washed sequentially with 5% aqueous NaHCO3 (10 mL), water (10 mL), brine (10 mL), dried (Na2SO4), filtered, and concentrated in vacuo. Recrystallization from petroleum ether affords the desired product. | CCOC(=O)c1c(-c2ccccc2Cl)csc1N1C(=O)c2ccccc2C1=O | null | O=C1OC(=O)c2ccccc21 | CCOC(=O)c1c(-c2ccccc2Cl)csc1N | null | [CH2:1]([O:3][C:4]([C:6]1[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])=[CH:9][S:8][C:7]=1[NH2:18])=[O:5])[CH3:2].[C:19]1(=O)[O:24][C:22](=[O:23])[C:21]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:20]12>C(O)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])=[CH:9][S:8][C:7]=1[N:18]1[C:22](=[O:23])[C:21]2[C:20](=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:19]1=[O:24])=[O:5])[CH3:2] | null | CC(=O)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 |
1,607,674 | [Li+] | [OH-] | null | null | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | 2015-01-01T00:07:00 | true | Add lithium hydroxide (0.10 g, 4.18 mmol) to a suspension of 3-[(4-cyano-phenylcarbamoyl)-methoxy]-benzoic acid methyl ester (0.50 g, 1.61 mmol) in a 1:1:1 mixture of water: MeOH: tetrahydrofuran. Stir the mixture at room temperature for 36 h then dilute with water and wash with EtOAc. Adjust the pH of the aqueous phase by the addition of a 1 N solution of hydrochloric acid. Extract the mixture with EtOAc and dry the combined organic phase over anhydrous sodium sulfate. Concentrate under reduced pressure to provide 0.290 g of 3-[(4-cyano-phenylcarbamoyl)-methoxy]-benzoic acid as a solid. | N#Cc1ccc(NC(=O)COc2cccc(C(=O)O)c2)cc1 | null | COC(=O)c1cccc(OCC(=O)Nc2ccc(C#N)cc2)c1 | null | null | [OH-].[Li+].C[O:4][C:5](=[O:25])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][C:14](=[O:24])[NH:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[CH:18][CH:17]=2)[CH:7]=1.CO.O1CCCC1>O>[C:22]([C:19]1[CH:18]=[CH:17][C:16]([NH:15][C:14]([CH2:13][O:12][C:8]2[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=2)[C:5]([OH:25])=[O:4])=[O:24])=[CH:21][CH:20]=1)#[N:23] | 36 | O | C1CCOC1 | CO | 25 | null | 60.8 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
866,651 | [I-] | [Na+] | null | null | ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | 2009-01-01T00:03:00 | true | Sodium iodide (1.4 g, 9.3 mmol) was added to a solution of chloromethyl isopropyl carbonate (750 mg, 4.8 mmol) in acetone (5 mL). The resulting mixture was stirred at room temperature for 2.5 h, followed by addition of 2-(3-(2,6-dichlorophenyl)isoxazol-5-yl)pyridin-4-amine (500 mg, 1.6 mmol). The reaction mixture was then stirred at room temperature for 7 d. The reaction mixture was concentrated under reduced pressure to provide isopropyl 3-(2-(3-(2,6-dichlorophenyl)isoxazol-5-yl)pyridin-4-ylamino)propanoate, which was carried forward without further purification. 1H NMR (CDCl3): 8.56 (d, 1H), 7.96 (s, 1H), 7.62 (m, 1H), 7.42-7.30 (m, 4H), 7.01 (s, 1H), 6.26 (d, 2H), 5.02 (m, 1H), 1.31 ppm (d, 6H). | CC(C)OC(=O)CCNc1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 | null | CC(C)=O | CC(C)OC(=O)OCCl | Nc1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 | [I-].[Na+].[C:3](=[O:11])([O:7][CH:8]([CH3:10])[CH3:9])OCCl.[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:14]=1[C:20]1[CH:24]=[C:23]([C:25]2[CH:30]=[C:29]([NH2:31])[CH:28]=[CH:27][N:26]=2)[O:22][N:21]=1.[CH3:32][C:33](C)=O>>[Cl:19][C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([Cl:12])[C:14]=1[C:20]1[CH:24]=[C:23]([C:25]2[CH:30]=[C:29]([NH:31][CH2:32][CH2:33][C:3]([O:7][CH:8]([CH3:9])[CH3:10])=[O:11])[CH:28]=[CH:27][N:26]=2)[O:22][N:21]=1 | 2.5 | 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 |
705,450 | CC(=O)[O-] | null | null | null | ord_dataset-c408dfed796e4354b61e312e67f7143f | 2006-01-01T00:04:00 | true | Ammonium acetate (26 g, 0.34 mol) was added to a solution of {4-[2-Oxo-2-(3-trifluoromethyl-phenyl)-ethylcarbamoyl]-cyclohexylmethyl}-carbamic acid benzyl ester (5.4 g, 0.0113 mol) in acetic acid. The resulting homogeneous mixture was refluxed overnight and then concentrated under reduced pressure. The residue was partitioned between 10% NaOH and EtOAc (1:1) and the EtOAc layer was washed with 10% NaOH (3×) and brine. The EtOAc was dried (Na2SO4) and concentrated under reduced pressure to give {4-[4-(3-Trifluoromethyl-phenyl)-1H-imidazol-2-yl]-cyclohexylmethyl}-carbamic acid benzyl ester. 1H NMR (CDCl3): δ 1.02–1.18 (m, 2H), 1.46–1.62 (m, 3H), 1.86–1.96 (m, 2H), 2.12–2.21 (m, 2H), 2.74 (m, 1H), 3.10 (t, J=6 Hz, 2H), 4.91 (t, 1H, N—H), 5.10 (s, 2H), 7.22 (s, 1H), 7.32–7.37 (m, 5H), 7.45 (d, J=4.9 hz, 2H), 7.87 (m, 1H), 7.95 (s, 1H). MS 458 (M+H)+ | O=C(NCC1CCC(c2nc(-c3cccc(C(F)(F)F)c3)c[nH]2)CC1)OCc1ccccc1 | null | O=C(NCC1CCC(C(=O)NCC(=O)c2cccc(C(F)(F)F)c2)CC1)OCc1ccccc1 | [NH4+] | null | C([O-])(=O)C.[NH4+:5].[CH2:6]([O:13][C:14](=[O:39])[NH:15][CH2:16][CH:17]1[CH2:22][CH2:21][CH:20]([C:23](=O)[NH:24][CH2:25][C:26](=O)[C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=2)[CH2:19][CH2:18]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(O)(=O)C>[CH2:6]([O:13][C:14](=[O:39])[NH:15][CH2:16][CH:17]1[CH2:22][CH2:21][CH:20]([C:23]2[NH:24][CH:25]=[C:26]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=3)[N:5]=2)[CH2:19][CH2:18]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1 | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,456,517 | O=C([O-])[O-] | [Na+] | null | null | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | 2014-01-01T00:07:00 | true | 2-Chloro-3-fluoropyridine (0.4380 g, 3.33 mmol), 4-chlorophenylboronic acid (0.6248 g, 3.996 mmol), palladium tetrakistriphenylphosphine (0.1924 g, 0.1665 mmol), sodium carbonate (0.4235 g, 3.996 mmol), toluene (10 mL), and water (1 mL) were placed in a teflon lined vial. The vial was sealed and stirred at 125° C. for 21 hour. The mixture was cooled to ambient temperature and the whole mixture was purified on silica gel (EtOAc-hexanes gradient) to provide 569.4 mg of the title compound as white solid (82%). | Fc1cccnc1-c1ccc(Cl)cc1 | null | OB(O)c1ccc(Cl)cc1 | Fc1cccnc1Cl | null | Cl[C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>O>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:2]2[C:7]([F:8])=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:12][CH:11]=1 | 21 | Cc1ccccc1 | O | null | 125 | 82.4 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
22,236 | [Al+3] | [Cl-] | null | null | ord_dataset-19b9e29d593f4660ab77c07b459da9bb | 1977-01-01T00:04:00 | true | In a most preferred embodiment of the process of this invention, a solution of 0.05 equivalents of the isatin derivative, 0.06 mole equivalents of the carbanilide, and 0.30 moles of aluminum chloride in 200 ml. of nitrobenzene are maintained at 100° C for about 12 hours. The cooled solution is poured into one liter of ice water and 600 ml. of hexane to precipitate the product. After filtering, the product is suspended in 200 ml. of acetic acid, 5 ml. of water, and 20 ml. of sulfuric acid. This solution is refluxed for approximately 24 hours, cooled and filtered. This refluxing hydrolyzes the reacted anilide and yields the desired oxindole diamine derivative. The filtrate containing the oxindole diamine derivative is neutralized with sodium carbonate and the solution concentrated in vacuo and taken in about 300 ml. of boiling 1N hydrochloric acid. This solution is diluted in about 300 ml. of water, cooled to about 5° C, filtered, and made basic with ammonia to precipitate the product. The product is collected and may be recrystallized from a dioxane hexane solution to yield the pure oxindole diamine derivative. | NC1C(=O)N(N)c2ccccc21 | null | O=C1Nc2ccccc2C1=O | O=C(Nc1ccccc1)Nc1ccccc1 | O=[N+]([O-])c1ccccc1 | [NH:1]1[C:11]2C(=CC=CC=2)C(=O)C1=O.C1C=CC(N[C:19]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:20])=CC=1.[Cl-].[Al+3].[Cl-].[Cl-].[N+:32](C1C=CC=CC=1)([O-])=O>>[N:21]1([NH2:32])[C:22]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:11]([NH2:1])[C:19]1=[O:20] | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
786,444 | CC[SiH](CC)CC | null | null | null | ord_dataset-4ad5db8537994579bef51f16dd8bf0bd | 2007-01-01T00:08:00 | true | A 50 mL single-neck round bottom flask was charged with ethyl 6-acetyl-2-(trifluoromethyl)-2H-chromene-3-carboxylate (1.465 g, 4.662 mmole), dichloromethane (4 mL), and triethyl silane (1.71 mL, 1.25 g, 10.72 mmole) and stirred at RT overnight. The crude reaction was poured into water and extracted several times with dichloromethane. The combined organics were washed with water, then with aqueous 10% sodium carbonate solution, dried over MgSO4, filtered and concentrated in vacuo to yield a colorless oil. This oil was purified by silica chromatography (9 hexane: 1 ethyl acetate) yielding the title compound as a clear, colorless oil (1.25 g, 89%): 1H NMR (acetone-d6/300 MHz) 7.84 (s, 1H), 7.30 (d, 1H, J=2.0 Hz), 7.26 (dd, 1H, J=8.3, 2.0 Hz), 6.93 (d, 1H, J=8.3 Hz), 5.79 (q, 1H, J=7.3 Hz), 4.37-4.24 (m, 2H), 2.60 (q, 2H, J=7.6 Hz), 1.32 (t, 3H, J=7.3 Hz), 1.20 (t, 3H, J=7.6 Hz). GCMS m/z 300 (M+). | CCOC(=O)C1=Cc2cc(CC)ccc2OC1C(F)(F)F | null | CCOC(=O)C1=Cc2cc(C(C)=O)ccc2OC1C(F)(F)F | null | null | [C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[O:10][CH:9]([C:14]([F:17])([F:16])[F:15])[C:8]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:7]2)(=O)[CH3:2].ClCCl.C([SiH](CC)CC)C>O>[CH2:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[O:10][CH:9]([C:14]([F:15])([F:16])[F:17])[C:8]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:7]2)[CH3:2] | 8 | O | ClCCl | 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 |
1,517,009 | null | null | null | null | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | 2014-01-01T00:12:00 | true | To a suspension of methyl 2-(6-oxo-4-phenyl-2-(piperidin-1-yl)-1,6-dihydropyrimidin-5-yl)pentanoate (1.74 g; 4,71 mmol) in dry toluene (10 mL) under nitrogen atmosphere were carefully added phosphorus oxychloride (4.38 mL; 47.1 mmol) and dimethylaniline (0.476 mL; 3.77 mmol) and the reaction mixture was heated to reflux for 3 h. The volatiles were removed under reduced pressure (while the reaction mixture was still at elevated temperature), the residue was cooled in an ice-bath and quenched by adding crushed ice and a saturated solution of sodium hydrogen carbonate until neutralization. The aqueous layer was extracted with ethyl acetate, the organics were collected, dried over magnesium sulphate, filtered and concentrated under reduced pressure. Purification by flash-chromatography on silica gel using a gradient of ethyl acetate (1-10%) in heptane furnished 0.040 g (1.6%, over 3 last steps) of the title compound as a yellow oil. | CCCC(C(=O)OC)c1c(Cl)nc(N2CCCCC2)nc1-c1ccccc1 | null | O=P(Cl)(Cl)Cl | CCCC(C(=O)OC)c1c(-c2ccccc2)nc(N2CCCCC2)[nH]c1=O | null | O=[C:2]1[NH:7][C:6]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[N:5][C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:3]1[CH:20]([CH2:25][CH2:26][CH3:27])[C:21]([O:23][CH3:24])=[O:22].P(Cl)(Cl)([Cl:30])=O.CN(C)C1C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:30][C:2]1[C:3]([CH:20]([CH2:25][CH2:26][CH3:27])[C:21]([O:23][CH3:24])=[O:22])=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:5]=[C:6]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[N:7]=1 | null | Cc1ccccc1 | CN(C)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,655,007 | Br | null | null | null | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | 2015-01-01T00:11:00 | true | (R)-4-methoxy-2-(2-(methoxymethyl)pyrrolidin-1-yl)-5-(6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)pyrimidine (96 mg, 0.20 mmol) was dissolved in AcOH (3 mL) and then 48% hydrobromic acid (0.1 mL) was added. The mixture was heated at 90° C. FOR 3.5 hours. The mixture was concentrated and the residue was treated with NaHCO3 solution. The solution was extracted with EtOAc (3×) and the organic was washed with NaHCO3, dried over Na2SO4, filtered and concentrated to obtain the crude. The material was treated with ether and sonicated. The solid was filtered, washed with ether and dried under vacuum to obtain (R)-2-(2-(methoxymethyl)pyrrolidin-1-yl)-5-(6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)pyrimidin-4(3H)-one (58 mg, 60.1% yield). 1H NMR (400 MHz, DMSO-d6): δ 11.15 (br s, 1H), 8.73 (s, 1H), 8.36 (d, J=5.7 Hz, 1H), 8.28 (br s, 1H), 8.26 (s, 1H), 7.97 (s, 1H), 7.53 (m, 1H), 7.23 (d, J=2.4 Hz, 1H), 6.62 (m, 1H), 4.34 (m, 1H), 3.85 (s, 3H), 3.52-3.40 (m, 4H), 3.28 (s, 3H), 2.35 (s, 3H), 1.95 (br d, J=27.5 Hz, 4H); MS (ESI) m/z: 474.3 (M+H+). | COC[C@H]1CCCN1c1ncc(-c2ccc(Oc3ccnc(-c4cnn(C)c4)c3)c(C)n2)c(=O)[nH]1 | null | COC[C@H]1CCCN1c1ncc(-c2ccc(Oc3ccnc(-c4cnn(C)c4)c3)c(C)n2)c(OC)n1 | null | null | C[O:2][C:3]1[C:8]([C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18]([C:22]4[CH:23]=[N:24][N:25]([CH3:27])[CH:26]=4)[CH:17]=3)=[C:11]([CH3:28])[N:10]=2)=[CH:7][N:6]=[C:5]([N:29]2[CH2:33][CH2:32][CH2:31][C@@H:30]2[CH2:34][O:35][CH3:36])[N:4]=1.Br.CCOCC>CC(O)=O>[CH3:36][O:35][CH2:34][C@H:30]1[CH2:31][CH2:32][CH2:33][N:29]1[C:5]1[NH:4][C:3](=[O:2])[C:8]([C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18]([C:22]4[CH:23]=[N:24][N:25]([CH3:27])[CH:26]=4)[CH:17]=3)=[C:11]([CH3:28])[N:10]=2)=[CH:7][N:6]=1 | 3.5 | CC(=O)O | CCOCC | null | 90 | 61.2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,413,542 | null | null | null | null | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | 2014-01-01T00:04:00 | true | (S)-tert-butoxycarbonylamino-cyclohexyl-acetic acid cyclopentyl ester (1.17 g, 3.60 mmol) was dissolved in a TFA/DCM mixture (1:1, 10 ml) at 0° C. The solution was stirred for 90 minutes, the solvent removed in vacuo. The residue was azetroped with a DCM/heptane mixture (2×) to give a gum. The gum was redissolved in DCM (10 ml) and washed with saturated aqueous NaHCO3 solution (3×10 ml), dried (MgSO4) and filtered. The solvent of the filtrate was removed in vacuo to give the product as an oil (0.780 g, 78% yield). 1H NMR (300 MHz, CDCl3), δ: 1.00-1.40 (10H, m, CH×10), 1.50-2.00 (8H, m, CH×8), 3.25 (1H, d, CH, J=7.2Hz), 5.20 (1H, m, CH). | N[C@H](C(=O)OC1CCCC1)C1CCCCC1 | null | CC(C)(C)OC(=O)N[C@H](C(=O)OC1CCCC1)C1CCCCC1 | null | null | [CH:1]1([O:6][C:7](=[O:23])[C@@H:8]([NH:15]C(OC(C)(C)C)=O)[CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH2:5][CH2:4][CH2:3][CH2:2]1>C(O)(C(F)(F)F)=O.C(Cl)Cl.C(Cl)Cl>[CH:1]1([O:6][C:7](=[O:23])[C@@H:8]([NH2:15])[CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[CH2:5][CH2:4][CH2:3][CH2:2]1 | 1.5 | ClCCl | O=C(O)C(F)(F)F | null | null | 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 |
1,700,303 | null | null | null | null | ord_dataset-54347fcace774f89850681d6dec8009f | 2016-01-01T00:03:00 | true | The title compound was prepared in an analogous fashion to that described in Example 75 using (S)-5-bromo-6-(3-(hydroxymethyl)pyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 78.1) and 2-cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine to afford an off-white solid. UPLC-MS (condition 1) tR=2.30 min, m/z=499.0 [M+H]+, m/z=497.1 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 0.90-1.04 (m, 4H) 1.49-1.62 (m, 1H) 1.77-1.88 (m, 1H) 2.10-2.19 (m, 1H) 2.18-2.26 (m, 1H) 2.99 (dd, J=11.00, 6.85 Hz, 1H) 3.09-3.20 (m, 2H) 3.21-3.29 (m, 1H) 3.29-3.41 (m, 2H) 4.60 (br. s, 1H) 7.29-7.40 (m, 3H) 7.64 (dd, J=8.07, 2.20 Hz, 1H) 7.85 (d, J=9.05 Hz, 2H) 7.99 (d, J=2.20 Hz, 1H) 8.45 (d, J=2.20 Hz, 1H) 8.73 (d, J=2.20 Hz, 1H) 10.14 (s, 1H). | O=C(Nc1ccc(OC(F)(F)F)cc1)c1cnc(N2CC[C@H](CO)C2)c(-c2ccc(C3CC3)nc2)c1 | null | O=C(Nc1ccc(OC(F)(F)F)cc1)c1cnc(N2CC[C@H](CO)C2)c(Br)c1 | CC1(C)OB(c2ccc(C3CC3)nc2)OC1(C)C | null | Br[C:2]1[C:3]([N:22]2[CH2:26][CH2:25][C@H:24]([CH2:27][OH:28])[CH2:23]2)=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[CH:29]1([C:32]2[CH:37]=[CH:36][C:35](B3OC(C)(C)C(C)(C)O3)=[CH:34][N:33]=2)[CH2:31][CH2:30]1>>[CH:29]1([C:32]2[N:33]=[CH:34][C:35]([C:2]3[C:3]([N:22]4[CH2:26][CH2:25][C@H:24]([CH2:27][OH:28])[CH2:23]4)=[N:4][CH:5]=[C:6]([C:7]([NH:9][C:10]4[CH:11]=[CH:12][C:13]([O:16][C:17]([F:19])([F:18])[F:20])=[CH:14][CH:15]=4)=[O:8])[CH:21]=3)=[CH:36][CH:37]=2)[CH2:31][CH2:30]1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,254,029 | Cl[Ti](Cl)(Cl)Cl | null | null | null | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | 2013-01-01T00:01:00 | true | 8-Methoxy-3,4-dihydro-1H-quinolin-2-one (5 g) was dissolved in dichloromethane (100 ml), and dichloromethyl methyl ether (6.4 ml) was added at room temperature, followed by cooling in an ice water bath. Titanium tetrachloride (85 ml) was added dropwise at a temperature not higher than 10° C., and the resulting mixture was stirred at room temperature overnight. The reaction mixture was poured into ice water, and the aqueous layer was subjected to extraction with dichloromethane. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. Diethyl ether was added to the residue and the produced solid was collected by filtration and dried to thereby obtain 5.2 g (yield: 90%) of 8-methoxy-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehyde. | COc1ccc(C=O)c2c1NC(=O)CC2 | null | COC(Cl)Cl | COc1cccc2c1NC(=O)CC2 | null | [CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[NH:11][C:10](=[O:13])[CH2:9][CH2:8]2.[CH3:14][O:15]C(Cl)Cl>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[C:12]2[NH:11][C:10](=[O:13])[CH2:9][CH2:8][C:7]=2[C:6]([CH:14]=[O:15])=[CH:5][CH:4]=1 | 8 | ClCCl | null | null | 25 | 90 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
570,424 | [H-] | [Na+] | null | null | ord_dataset-5e1b2445a3d94ea592ddf2c284118a1e | 2002-01-01T00:11:00 | true | A solution of 11 g (0.0617 mol) of benzofuran-2,3-dione dioxime in 50 ml of dimethylformamide is added dropwise to a suspension of 2.4 g (0.06 mol) of 60% strength sodium hydride in 25 ml of dimethylformamide, and stirring is effected at 20° C. for one hour. 7.55 g (0.06 mol) of dimethyl sulphate are then added dropwise and stirring is continued at 20° C. for a further 16 hours. The reaction mixture is poured into water and the resulting mixture is extracted with ethyl acetate, the organic phase is dried over sodium sulphate and concentrated under reduced pressure. The residue is chromatographed over silica gel using hexane/acetone (7:3). Stirring the residue with diethyl ether affords 0.7 g of benzofuran-2,3-dione3-(O-methyl-oxime)2-oxime (VIII-1) as a mixture of stereoisomers consisting of 90.6% of isomer A and 9% of isomer B (HPLC). | CON=C1C(=NO)Oc2ccccc21 | null | ON=C1Oc2ccccc2C1=NO | COS(=O)(=O)OC | null | [O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3](=[N:10][OH:11])[C:2]1=[N:12][OH:13].[H-].[Na+].S(OC)(O[CH3:20])(=O)=O.O>CN(C)C=O>[CH3:20][O:11][N:10]=[C:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[O:1][C:2]1=[N:12][OH:13] | 1 | CN(C)C=O | O | null | null | 6.1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,744,898 | COc1cccc2c1CC[C@H](C)N2 | null | null | null | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | 2016-01-01T00:07:00 | true | (S)-8-Fluoro-5-methoxy-2-methyl-1,2,3,4-tetrahydroquinoline was synthesized from 8-fluoro-5-methoxy-2-methylquinoline according to the procedures described above for (2S)-5-methoxy-2-methyl-1,2,3,4-tetrahydroquinoline (Intermediate 1). MS (ESI, pos. ion) m/z 196 [M+H]+. | COc1ccc(F)c2c1CC[C@H](C)N2 | null | COc1ccc(F)c2nc(C)ccc12 | null | null | [F:1][C:2]1[CH:3]=[CH:4][C:5]([O:13][CH3:14])=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[CH:7]2.COC1C=CC=C2C=1CC[C@H](C)N2>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:13][CH3:14])=[C:6]2[C:11]=1[NH:10][C@@H:9]([CH3:12])[CH2:8][CH2:7]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 |
1,336,039 | CC(=O)O[BH-](OC(C)=O)OC(C)=O | O=C([O-])O | [Na+] | null | ord_dataset-08852243bba44cb28769a5833f1515fe | 2013-01-01T00:09:00 | true | To 10 mL of a chloroform solution containing 226 mg of 1-(2-(4-aminopiperidin-1-yl)ethyl)-7-methoxyquinoxalin-2(1H)-one and 150 mg of 2,2-difluorobenzo[1,3]dioxol-5-carbaldehyde, 43 μL of acetic acid was added, and stirred at room temperature for 1 hour. To the reaction mixture, 257 mg of sodium triacetoxyborohydride was added, and stirred for 2.5 hours. To the reaction mixture, aqueous saturated sodium hydrogen carbonate solution was added, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [Silica Gel; Kanto Chemical Co., Inc., Silica Gel 60, eluent; chloroform:methanol=10:1] to give 188 mg of 1-(2-(4-((2,2-difluorobenzo[1,3]dioxol-5-yl)methylamino)piperidin-1-yl)ethyl)-7-methoxyquinoxalin-2(1H)-one as a pale yellow solid. | COc1ccc2ncc(=O)n(CCN3CCC(NCc4ccc5c(c4)OC(F)(F)O5)CC3)c2c1 | null | COc1ccc2ncc(=O)n(CCN3CCC(N)CC3)c2c1 | O=Cc1ccc2c(c1)OC(F)(F)O2 | null | [NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH3:21])[CH:18]=3)[N:13]=[CH:12][C:11]2=[O:22])[CH2:4][CH2:3]1.[F:23][C:24]1([F:35])[O:28][C:27]2[CH:29]=[CH:30][C:31]([CH:33]=O)=[CH:32][C:26]=2[O:25]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(O)(=O)C.C(Cl)(Cl)Cl>[F:35][C:24]1([F:23])[O:28][C:27]2[CH:29]=[CH:30][C:31]([CH2:33][NH:1][CH:2]3[CH2:3][CH2:4][N:5]([CH2:8][CH2:9][N:10]4[C:19]5[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH3:21])[CH:18]=5)[N:13]=[CH:12][C:11]4=[O:22])[CH2:6][CH2:7]3)=[CH:32][C:26]=2[O:25]1 | 1 | ClC(Cl)Cl | CC(=O)O | null | 25 | 53.2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
988,116 | Cl | O=C([O-])[O-] | [K+] | null | ord_dataset-35b56288528641309a040cc2b6710b61 | 2010-01-01T00:08:00 | true | Add potassium carbonate (40 mg, 0.29 mmol) and bromoethanol (0.018 mL, 0.26 mmol) to a solution of (S)-9-[(3,5-Bis-trifluoromethyl-benzyl)-(2H-tetrazol-5-yl)-amino]-2,3,6,7,8,9-hexahydro-1H-5-aza-cyclohepta[f]indene-5-carboxylic acid isopropyl ester (50 mg, 0.086 mmol) in dimethylformamide (0.3 mL). Stir at room temperature for 18 hrs in a sealed tube. Then add bromoethanol (0.018 mL, 0.26 mmol) and stir for 2 hrs. Add a 1N solution of hydrochloric acid and extract with dichloromethane. Dry the organic phase over anhydrous sodium sulfate, filter and concentrate in vacuo. Purify the residue using silica gel cartridge, eluting with ethyl acetate/hexanes to afford the title compound (26 mg, 49%). MS (ES+): 627 (M+H). | CC(C)OC(=O)N1CCC[C@H](N(Cc2cc(C(F)(F)F)cc(C(F)(F)F)c2)c2nnn(CCO)n2)c2cc3c(cc21)CCC3 | null | CC(O)Br | CC(C)OC(=O)N1CCC[C@H](N(Cc2cc(C(F)(F)F)cc(C(F)(F)F)c2)c2nn[nH]n2)c2cc3c(cc21)CCC3 | null | C(=O)([O-])[O-].[K+].[K+].Br[CH:8]([OH:10])[CH3:9].[CH:11]([O:14][C:15]([N:17]1[C:30]2[C:22](=[CH:23][C:24]3[CH2:25][CH2:26][CH2:27][C:28]=3[CH:29]=2)[C@@H:21]([N:31]([CH2:37][C:38]2[CH:43]=[C:42]([C:44]([F:47])([F:46])[F:45])[CH:41]=[C:40]([C:48]([F:51])([F:50])[F:49])[CH:39]=2)[C:32]2[N:33]=[N:34][NH:35][N:36]=2)[CH2:20][CH2:19][CH2:18]1)=[O:16])([CH3:13])[CH3:12].Cl>CN(C)C=O>[CH:11]([O:14][C:15]([N:17]1[C:30]2[C:22](=[CH:23][C:24]3[CH2:25][CH2:26][CH2:27][C:28]=3[CH:29]=2)[C@@H:21]([N:31]([CH2:37][C:38]2[CH:39]=[C:40]([C:48]([F:49])([F:50])[F:51])[CH:41]=[C:42]([C:44]([F:45])([F:46])[F:47])[CH:43]=2)[C:32]2[N:33]=[N:34][N:35]([CH2:9][CH2:8][OH:10])[N:36]=2)[CH2:20][CH2:19][CH2:18]1)=[O:16])([CH3:13])[CH3:12] | 18 | CN(C)C=O | null | null | 25 | null | 48.2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
598,594 | null | null | null | null | ord_dataset-843ef38b45484f72826f5f39d8a29c4d | 2003-01-01T00:06:00 | true | The product from Example 305G and ethyl glycolate were processed as described in Example 62A to provide the title compound. | CCOC(=O)COc1cc(Oc2ccc(CN(Cc3ccc(F)cc3F)c3cccc([N+](=O)[O-])c3C)cc2)ccc1F | null | CCOC(=O)CO | Cc1c(N(Cc2ccc(Oc3ccc(F)c(O)c3)cc2)Cc2ccc(F)cc2F)cccc1[N+](=O)[O-] | null | [F:1][C:2]1[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:3]=1[CH2:4][N:5]([CH2:16][C:17]1[CH:31]=[CH:30][C:20]([O:21][C:22]2[CH:23]=[CH:24][C:25]([F:29])=[C:26]([OH:28])[CH:27]=2)=[CH:19][CH:18]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:7]=1[CH3:15].[C:37]([O:41][CH2:42][CH3:43])(=[O:40])[CH2:38]O>>[F:1][C:2]1[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:3]=1[CH2:4][N:5]([CH2:16][C:17]1[CH:31]=[CH:30][C:20]([O:21][C:22]2[CH:23]=[CH:24][C:25]([F:29])=[C:26]([CH:27]=2)[O:28][CH2:38][C:37]([O:41][CH2:42][CH3:43])=[O:40])=[CH:19][CH:18]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:7]=1[CH3:15] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
870,253 | O=C([O-])O | [Na+] | null | null | ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | 2009-01-01T00:03:00 | true | A mixture of 2-bromo-4′-methylacetophenone (152 mg, 0.7 mmol) and 4-bromobenzamide (200 mg, 1.0 mmol) was heated to 160° C. for 3 hours, cooled to room temperature, dissolved in ethyl acetate (20 mL), and treated with 5% sodium bicarbonate (20 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×10 mL). The combined extracts were dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 50% ethyl acetate/hexanes to provide the desired product. MS (DCI) m/e 314, 316 (M−H)−, (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 8.70 (s, 1H), 8.00-7.97 (m, 2H), 7.79-7.76 (m, 2H), 7.77-7.74 (m, 2H), 7.29-7.27 (m, 2H), 2.34 (s, 31). | Cc1ccc(-c2coc(-c3ccc(Br)cc3)n2)cc1 | null | Cc1ccc(C(=O)CBr)cc1 | NC(=O)c1ccc(Br)cc1 | null | Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1)=O.[Br:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([NH2:19])=[O:18])=[CH:15][CH:14]=1.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[Br:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]2[O:18][CH:2]=[C:3]([C:5]3[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=3)[N:19]=2)=[CH:15][CH:14]=1 | null | CCOC(C)=O | null | null | 160 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
938,660 | null | null | null | null | ord_dataset-90b0aa1f83334a02919b2be3a1c04542 | 2010-01-01T00:02:00 | true | 3-Bromo-benzoic acid (112 mg, 0.56 mmol) was coupled with ethyl ester (6) (100 mg, 0.56 mmol) following Method C to give the title compound. | CCOC(=O)Cc1cccc(NC(=O)c2cccc(Br)c2)c1 | null | CCOC(=O)Cc1cccc(N)c1 | O=C(O)c1cccc(Br)c1 | null | [Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.[CH2:11]([O:13][C:14](=[O:23])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([NH2:22])[CH:17]=1)[CH3:12]>>[CH2:11]([O:13][C:14](=[O:23])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][C:5](=[O:7])[C:4]2[CH:8]=[CH:9][CH:10]=[C:2]([Br:1])[CH:3]=2)[CH:17]=1)[CH3:12] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,343,500 | null | null | null | null | ord_dataset-6034127657614f02860ed057b62b882e | 2013-01-01T00:10:00 | true | The compound is prepared by the reaction of 1-bromo-6-(3-hydroxyphenyl)-naphthalene-2-ol (100 mg, 0.32 mmol, 1 eq) with N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamide (94.3 mg, 0.32 mmol, 1 eq) according to method A in 2 h. Purification by column chromatography with hexane/ethyl acetate 3/2 yields the desired compound in a yield of 64%, 83 mg. | CS(=O)(=O)Nc1cccc(-c2c(O)ccc3cc(-c4cccc(O)c4)ccc23)c1 | null | Oc1cccc(-c2ccc3c(Br)c(O)ccc3c2)c1 | CC1(C)OB(c2cccc(NS(C)(=O)=O)c2)OC1(C)C | null | Br[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=3)=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[OH:19].CC1(C)C(C)(C)OB([C:28]2[CH:29]=[C:30]([NH:34][S:35]([CH3:38])(=[O:37])=[O:36])[CH:31]=[CH:32][CH:33]=2)O1>>[OH:19][C:3]1[CH:4]=[CH:5][C:6]2[C:11](=[CH:10][CH:9]=[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=3)[CH:7]=2)[C:2]=1[C:28]1[CH:29]=[C:30]([NH:34][S:35]([CH3:38])(=[O:36])=[O:37])[CH:31]=[CH:32][CH:33]=1 | 2 | null | null | null | null | null | 64 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
30,846 | null | null | null | null | ord_dataset-56c07ce5503b46d1805bdf471f8f1c55 | 1977-01-01T00:10:00 | true | 534 mg. (3 mmol.) of N-bromosuccinimide (recrystallized from water) were added in small portions to a solution of 831 mg. (3 mmol.) of 3-acetyl-2,6-di-t-butylamino-4-methylpyridine (Compound V) in 20 ml. of carbon tetrachloride and 5 ml. of ethanol, and the reaction mixture was allowed to stand overnight at room temperature. The reaction mixture was evaporated down at reduced pressure, and the residue was partitioned between ether and water. The organic phase was dried over anhydrous sodium sulfate and evaporated at reduced pressure to obtain yellow crystals. Recrystallization from methanol/water gave the product (990 mg.), m.p. 99°-100° C. | CC(=O)c1c(NC(C)(C)C)nc(NC(C)(C)C)c(Br)c1C | null | O=C1CCC(=O)N1Br | CC(=O)c1c(C)cc(NC(C)(C)C)nc1NC(C)(C)C | null | [Br:1]N1C(=O)CCC1=O.[C:9]([C:12]1[C:13]([NH:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[N:14][C:15]([NH:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:16][C:17]=1[CH3:18])(=[O:11])[CH3:10].C(Cl)(Cl)(Cl)Cl>C(O)C>[C:9]([C:12]1[C:13]([NH:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[N:14][C:15]([NH:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[C:16]([Br:1])[C:17]=1[CH3:18])(=[O:11])[CH3:10] | 8 | ClC(Cl)(Cl)Cl | 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 |
462,017 | O=C([O-])[O-] | [I-] | [K+] | null | ord_dataset-5ca9db262dd24c5a9315cdc8ef055b7e | 2000-01-01T00:04:00 | true | A mixture of ethyl 4-(4-methylphenyl)-4-piperidine carboxylate (3.0 g, 0.012 mol, prepared similarly as described in the method in Pol. Pat. 105 435 or Ber. 74, 1433 (1941)), 5-(3-bromo-1-propylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (4.50 g, 0.0145 mol), anhydrous potassium carbonate (5.00 g, 0.036 mol) and potassium iodide (4.0 g, 0.024 mol) in 2-butanone (100 ml) was stirred at 80° C. for 7.5 h. The mixture was diluted with ether (150 ml) and water (150 ml) and the layers were separated. The aqueous phase was extracted with additional ether (80 ml) and the combined organic extracts were washed with water (100 ml) and dried (MgSO4). The solvent was removed in vacuo and the oily residue (6.60 g) was purified by gradient column chromatography on silica gel using mixtures of benzene and ethyl acetate as eluents. The benzene/ethyl acetate (9:1) fraction afforded 2.90 g (50%) of 4-(4-methylphenyl)-1-(3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-propyl)-4-piperidinecarboxylic acid ethyl ester. | CCOC(=O)C1(c2ccc(C)cc2)CCN(CCC=C2c3ccccc3CCc3ccccc32)CC1 | null | BrCCC=C1c2ccccc2CCc2ccccc21 | CCOC(=O)C1(c2ccc(C)cc2)CCNCC1 | null | [CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Br[CH2:20][CH2:21][CH:22]=[C:23]1[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[CH2:27][CH2:26][C:25]2[CH:34]=[CH:35][CH:36]=[CH:37][C:24]1=2.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(=O)CC.CCOCC.O>[CH2:17]([O:16][C:14]([C:8]1([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=2)[CH2:9][CH2:10][N:11]([CH2:20][CH2:21][CH:22]=[C:23]2[C:24]3[CH:37]=[CH:36][CH:35]=[CH:34][C:25]=3[CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]2=3)[CH2:12][CH2:13]1)=[O:15])[CH3:18] | null | O | CCOCC | CCC(C)=O | null | 50 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,088,731 | null | null | null | null | ord_dataset-52a37d876ddb453e86de0c15fa233d29 | 2011-01-01T00:09:00 | true | A mixture of the compound (2.12 g) obtained in Step 4 and 2-bromo-3-oxobutyric acid tert-butyl ester (2.0 g) in acetonitrile (20 ml) was stirred at 80° C. for 30 min. The reaction mixture was concentrated under reduced pressure, and the residue was partitioned by adding ethyl acetate and saturated aqueous sodium carbonate solution. The organic layer was washed successively with saturated aqueous sodium carbonate solution and saturated brine, dried over anhydrous sodium sulfate, filtrated, and concentrated under reduced pressure. The residue was purified by column chromatography (ethyl acetate:n-hexane=1:2) to give the title compound (1.82 g). | Cc1nc(N2CCN(S(=O)(=O)c3ccc(OC(F)(F)F)cc3)[C@@H](C(=O)OCc3ccccc3)C2)sc1C(=O)OC(C)(C)C | null | NC(=S)N1CCN(S(=O)(=O)c2ccc(OC(F)(F)F)cc2)[C@@H](C(=O)OCc2ccccc2)C1 | CC(=O)C(Br)C(=O)OC(C)(C)C | null | [CH2:1]([O:8][C:9]([C@H:11]1[CH2:16][N:15]([C:17](=[S:19])[NH2:18])[CH2:14][CH2:13][N:12]1[S:20]([C:23]1[CH:28]=[CH:27][C:26]([O:29][C:30]([F:33])([F:32])[F:31])=[CH:25][CH:24]=1)(=[O:22])=[O:21])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:34]([O:38][C:39](=[O:45])[CH:40](Br)[C:41](=O)[CH3:42])([CH3:37])([CH3:36])[CH3:35]>C(#N)C>[CH2:1]([O:8][C:9]([C@H:11]1[CH2:16][N:15]([C:17]2[S:19][C:40]([C:39]([O:38][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:45])=[C:41]([CH3:42])[N:18]=2)[CH2:14][CH2:13][N:12]1[S:20]([C:23]1[CH:24]=[CH:25][C:26]([O:29][C:30]([F:33])([F:31])[F:32])=[CH:27][CH:28]=1)(=[O:21])=[O:22])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1 | 0.5 | CC#N | null | null | 80 | 67.4 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,128,008 | F[P-](F)(F)(F)(F)F | null | null | null | ord_dataset-285df12e34cd46e993e3c8ebc3a8962a | 2012-01-01T00:01:00 | true | A mixture of (1R,10R,11S,16S)-1,11,15,15-tetramethyl-8,8-dioxo-8λ6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-3,5-dicarboxylic acid (85) (0.07 g, 0.2 mmol), HATU (0.25 g, 0.65 mmol) and 4-methylmorpholine (0.07 mL, 1 mmol) in THF (10 mL) and DMF (2.0 mL) was stirred at room temperature for 18 h in a sealed vessel. The mixture was concentrated under reduced pressure and the residue was triturated with water. The resulting solid was collected by filtration to give (1R,10R,11S,16S)-1,3-N,5-N,11,15,15-hexamethyl-8,8-dioxo-8λ6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-3,5-dicarboxamide (86) (0.035 g, 47%) as a white solid. 1H NMR (CD3OD): δ 8.38 (d, 1H), 7.88 (d, 1H), 3.54 (m, 2H), 2.90 (d, 6H), 2.67 (d, 1H), 2.18 (d, 1H), 1.90-1.48 (m, 9H), 1.46-1.14 (m, 3H), 1.06-0.93 (m, 4H), 0.90 (s, 3H), 0.87 (s, 3H). MS m/z 461 (C25H36N2O4S+H+). | CNC(=O)c1cc(C(=O)NC)c2c(c1)S(=O)(=O)C[C@@H]1[C@@]3(C)CCCC(C)(C)[C@@H]3CC[C@@]21C | null | CC1(C)CCC[C@]2(C)[C@H]3CS(=O)(=O)c4cc(C(=O)O)cc(C(=O)O)c4[C@]3(C)CC[C@@H]12 | CN1CCOCC1 | CN(C)C(On1nnc2cccnc21)=[N+](C)C | [CH3:1][C@@:2]12[CH2:19][CH2:18][C@@H:17]3[C@:12]([CH3:22])([CH2:13][CH2:14][CH2:15][C:16]3([CH3:21])[CH3:20])[C@H:11]1[CH2:10][S:9](=[O:24])(=[O:23])[C:8]1[C:3]2=[C:4]([C:28]([OH:30])=O)[CH:5]=[C:6]([C:25](O)=[O:26])[CH:7]=1.[CH3:31][N:32](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:55][N:56]1CCOCC1>C1COCC1.CN(C=O)C>[CH3:1][C@@:2]12[CH2:19][CH2:18][C@@H:17]3[C@:12]([CH3:22])([CH2:13][CH2:14][CH2:15][C:16]3([CH3:21])[CH3:20])[C@H:11]1[CH2:10][S:9](=[O:24])(=[O:23])[C:8]1[C:3]2=[C:4]([C:28]([NH:56][CH3:55])=[O:30])[CH:5]=[C:6]([C:25]([NH:32][CH3:31])=[O:26])[CH:7]=1 | 18 | C1CCOC1 | CN(C)C=O | null | 25 | 38 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
916,558 | [BH4-] | [Na+] | null | null | ord_dataset-8e59bd24817446f7b1c68e805b8e5f1d | 2009-01-01T00:11:00 | true | NaBH4 (5.2 g) was added to a stirred solution of 4,5-dichlorophthalic anhydride (20 g) in anhydrous DMF (100 mL) at 0° C. under nitrogen in small portions over 1 hour. The reaction was warmed to room temperature for a further 2 hours and poured into ice/1M HCl. The resultant white precipitate (4,5-dichloro-2-hydroxymethyl-benzoic acid) was collected by filtration and dried under vacuum. The precipitate was suspended in toluene (200 mL) with catalytic pTSA and heated to reflux under Dean-Stark conditions (precipitate dissolves on heating) for 18 hours. The reaction was cooled to room temperature and the resultant white precipitate collected by filtration to give the sub-title compound as a white solid (14.0 g, 75%); 1H NMR (400 MHz, d6-DMSO) δ 5.40 (2H, s), 8.05 (1H, s), 8.15 (1H, s). | O=C1OCc2cc(Cl)c(Cl)cc21 | null | O=C1OC(=O)c2cc(Cl)c(Cl)cc21 | null | null | [BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]2[C:11](=O)[O:10][C:8](=[O:9])[C:7]2=[CH:13][C:14]=1[Cl:15]>CN(C=O)C>[Cl:3][C:4]1[CH:5]=[C:6]2[C:7](=[CH:13][C:14]=1[Cl:15])[C:8](=[O:9])[O:10][CH2:11]2 | null | CN(C)C=O | null | null | 25 | 74.8 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,108,145 | null | null | null | null | ord_dataset-375a420ee9b042918ddca20f02df37d3 | 2011-01-01T00:11:00 | true | The process is carried out as in Example 80 above, with the compound from Example 60B, 6-acetyl-3-(4-bromophenyl)-1,9-dimethyl-1,9-dihydropyrido[2,3-b]indol-2-one and diethyl oxalate. | CCOC(=O)C(=O)CC(=O)c1ccc2c(c1)c1cc(-c3ccc(Br)cc3)c(=O)n(C)c1n2C | null | CCOC(=O)C(=O)OCC | CC(=O)c1ccc2c(c1)c1cc(-c3ccc(Br)cc3)c(=O)n(C)c1n2C | null | [C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH3:13])[C:8]1[N:14]([CH3:26])[C:15](=[O:25])[C:16]([C:18]3[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][CH:19]=3)=[CH:17][C:7]2=1)(=[O:3])[CH3:2].[C:27](OCC)(=[O:33])[C:28]([O:30][CH2:31][CH3:32])=[O:29]>>[CH2:31]([O:30][C:28](=[O:29])[C:27](=[O:33])[CH2:2][C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH3:13])[C:8]1[N:14]([CH3:26])[C:15](=[O:25])[C:16]([C:18]3[CH:19]=[CH:20][C:21]([Br:24])=[CH:22][CH:23]=3)=[CH:17][C:7]2=1)=[O:3])[CH3:32] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
548,891 | CC(C)COC(=O)Cl | CCN1CCOCC1 | null | null | ord_dataset-e967d076b4894c2c854795f019ed3c39 | 2002-01-01T00:06:00 | true | 2 g of 1-(N-(tert-butoxycarbonyl)-2(S)-amino-butyryl)-L-proline (6.6 mmol) prepared as in Example 2 c) are dissolved in tetrahydrofuran (40 ml). 0.86 ml of isobutyl chloroformate (6.6 mmol) and 0.85 ml of N.-ethylmorpholine (6.6 mmol) are then added to this solution, at −10° C. and under nitrogen. After stirring at −10° C. for 20 minutes, 2.75 ml of n-propylamine (33.0 mmol) are added. The mixture is left stirring at 0° C. for one hour and then at room temperature overnight. The solvent is evaporated off under vacuum and a white semi-solid material is obtained. It is dissolved in ethyl acetate (150 ml) and washed with 5% citric acid (30 ml), saturated sodium bicarbonate solution (30 ml) and brine (20 ml). After drying (Na2SO4) the mixture is filtered and the solvent is evaporated off. An oil is obtained, which is purified by liquid chromatography on a column (eluent: ethyl acetate) and a white solid is obtained. | CCCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CC)NC(=O)OC(C)(C)C | null | CCCN | CC[C@H](NC(=O)OC(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O | null | [C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:20][CH3:21])[C:10]([N:12]1[CH2:19][CH2:18][CH2:17][C@H:13]1[C:14]([OH:16])=O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC(OCC(C)C)=O.C(N1CCOCC1)C.[CH2:38]([NH2:41])[CH2:39][CH3:40]>O1CCCC1.C(OCC)(=O)C>[CH2:38]([NH:41][C:14](=[O:16])[C@@H:13]1[CH2:17][CH2:18][CH2:19][N:12]1[C:10](=[O:11])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:20][CH3:21])[CH2:39][CH3:40] | 0.33 | C1CCOC1 | CCOC(C)=O | null | -10 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,372,793 | Cl | null | null | null | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | 2013-01-01T00:12:00 | true | To the product from step 1 (91 mg, 0.246 mmol) was added 4M HCl in dioxane (6 mL) and the resulting mixture was stirred at rt for 3 h. The solvent was removed in vacuo to obtain the product as a oil (63 mg, 95%); MS; m/z 270 (M+H): LCMS (UV) 99%; 1H NMR (400 MHz, DMSO-d6) δ 1.71-1.78 (m, 1H), 1.89-2.0 (m, 2H), 2.1-2.15 (m, 1H), 3.16-3.24 (m, 2H), 3.88-3.93 (m, 1H), 4.11-4.15 (dd, 1H J1=8.4 Hz, J2=10.8 Hz), 4.22-4.26 (dd, 1H J1=3.6 Hz, J2=10.8 Hz), 6.91-6.94 (m, 2H), 7.03 (s, 3H), 7.06-7.1 (m, 1H), 7.34-7.38 (m, 2H) | c1ccc(Oc2ccc(OC[C@H]3CCCN3)cc2)cc1 | null | CC(C)(C)OC(=O)N1CCC[C@@H]1COc1ccc(Oc2ccccc2)cc1 | null | null | C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:17][CH:16]=1)=O)(C)(C)C.Cl>O1CCOCC1>[O:21]([C:18]1[CH:19]=[CH:20][C:15]([O:14][CH2:13][C@H:9]2[CH2:10][CH2:11][CH2:12][NH:8]2)=[CH:16][CH:17]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1 | 3 | C1COCCO1 | null | null | 25 | 95.1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
707,217 | Cl | null | null | null | ord_dataset-c8069773c1a148aca8ab417108daacc5 | 2006-01-01T00:05:00 | true | Made using the same procedure as for [4-(2,4-dichlorophenyl)-5-pyrazolylpyrimidin-2-yl]{2-[(5-nitro(2-pyridyl))amino]ethyl}amine dihydrochloride except that 2-benzimidazolyl-1-(2,4-dichlorophenyl)-3-(dimethylamino)prop-2-en-1-one (XIV, 468 mg, 1.3 mmol) was used and the crude product was purified by recrystallization (CH2Cl2/Et2O/hexanes). | O=[N+]([O-])c1ccc(NCCNc2ncc(-c3nc4ccccc4[nH]3)c(-c3ccc(Cl)cc3Cl)n2)nc1 | null | CN(C)C=C(C(=O)c1ccc(Cl)cc1Cl)c1nc2ccccc2[nH]1 | O=[N+]([O-])c1ccc(NCCNc2ncc(-c3cc[nH]n3)c(-c3ccc(Cl)cc3Cl)n2)nc1 | null | Cl.Cl.[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[C:11]1[C:16]([C:17]2C=CN[N:18]=2)=[CH:15][N:14]=[C:13]([NH:22][CH2:23][CH2:24][NH:25][C:26]2[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][N:27]=2)[N:12]=1.[N:35]1[C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=2NC=1C(=CN(C)C)C(C1C=CC([Cl:53])=CC=1Cl)=O>>[ClH:3].[ClH:53].[N:18]1[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=2[NH:35][C:17]=1[C:16]1[C:11]([C:5]2[CH:6]=[CH:7][C:8]([Cl:10])=[CH:9][C:4]=2[Cl:3])=[N:12][C:13]([NH:22][CH2:23][CH2:24][NH:25][C:26]2[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][N:27]=2)=[N:14][CH:15]=1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,256,093 | O=C(Cl)C/C=C/c1ccccc1 | [N-]=[N+]=NCCN | null | null | ord_dataset-266f60b4555945d6afb2d2bdf5fa04e0 | 2013-01-01T00:02:00 | true | As in the synthesis of N-(2-azidoethyl)tetradecanamide, (E)-4-phenylbut-3-enoyl chloride (0.198 g, 1.19 mmol) was reacted with 2-azidoethanamine (0.114 g, 1.19 mmol) and triethylamine (0.239 g, 2.37 mmol) in dichloromethane (5 mL) to give (E)-N-(2-azidoethyl)-4-phenylbut-3-enamide (0.168 g, 55%). 1H NMR (300 MHz, CDCl3) δ 7.68 (d, 1H), δ 7.45 (d, 2H), δ 7.29 (m, 3H), δ 7.04 (t, 1H), δ 6.59 (d, 1H), δ 3.55 (q, 2H), δ 3.47 (t, 2H) ppm; 13C NMR (75 MHz, CDCl3) δ 166.9, 141.6, 134.9, 130.1, 129.1, 128.1, 120.8, 51.1, 39.4 ppm; HRMS (ESI) calcd for C11H12N4O (M+) 216.1011, found 216.1005. | [N-]=[N+]=NCCNC(=O)C/C=C/c1ccccc1 | null | CCCCCCCCCCCCCC(=O)NCCN=[N+]=[N-] | null | null | [N:1]([CH2:4][CH2:5][NH:6][C:7](=[O:21])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]CCCC)=[N+:2]=[N-:3].C1(/C=C/CC(Cl)=O)C=CC=CC=1.N(CCN)=[N+]=[N-].C(N(CC)CC)C>ClCCl>[N:1]([CH2:4][CH2:5][NH:6][C:7](=[O:21])[CH2:8]/[CH:9]=[CH:10]/[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[N+:2]=[N-:3] | null | ClCCl | CCN(CC)CC | null | null | 55 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
888,923 | null | null | null | null | ord_dataset-d728a2f811c0424cbcdb5a84d02b93ae | 2009-01-01T00:06:00 | true | To a solution of methyl(2S)-3,3,3-trifluoro-2-hydroxy-2-methylpropanoate (3.26 g, 19.0 mmol) was added hydrazine monohydrate (2.1 ml). The mixture was heated at 130° C. for 90 min and cooled down to room temperature. After evaporation to dryness, the residue was purified on a small bed of silica gel (100% EtOAc) to afford the title compound. | C[C@](O)(C(=O)NN)C(F)(F)F | null | COC(=O)[C@](C)(O)C(F)(F)F | NN | null | [F:1][C:2]([F:11])([F:10])[C@:3]([OH:9])([CH3:8])[C:4](OC)=[O:5].O.[NH2:13][NH2:14]>>[F:1][C:2]([F:11])([F:10])[C@:3]([OH:9])([CH3:8])[C:4]([NH:13][NH2:14])=[O:5] | null | O | null | null | 130 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,674,063 | CC(C)COC(=O)Cl | N | null | null | ord_dataset-9cc455db05a444779921f786a45b21a6 | 2015-01-01T00:12:00 | true | To a solution of 1-phenyl-1H-1,2,3-triazole-5-carboxylic acid (1.0 g, 5.6 mmol) and 4-methylmorpholine (0.57 g, 5.6 mmol) in 1,2-dimethoxyethane (5 mL), isobutyl chloroformate (0.77, 5.6 mmol) was added to the mixture. After 30 minutes, ammonia in dioxane (16.8 mL, 8.4 mmol) was added to the reaction. Then it was stirred overnight. The solvent was removed and dissolved in 50 mL of ethyl acetate. The organic layer was washed with brine twice. The organic layer was dried with Na2SO4, filtered and concentrated and used without further purification. MS (m/z) 189 [M+H]+. | NC(=O)c1cnnn1-c1ccccc1 | null | CN1CCOCC1 | O=C(O)c1cnnn1-c1ccccc1 | null | [C:1]1([N:7]2[C:11]([C:12]([OH:14])=O)=[CH:10][N:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[N:16]1CCOCC1.ClC(OCC(C)C)=O.N.O1CCOCC1>COCCOC>[C:1]1([N:7]2[C:11]([C:12]([NH2:16])=[O:14])=[CH:10][N:9]=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1 | 0.5 | COCCOC | 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 |
29,681 | Cl | [Na+] | [OH-] | null | ord_dataset-dc78376bd0a946d1a5a41eec30282b7d | 1977-01-01T00:09:00 | true | The quinoline (30g), hydroxylamine hydrochloride (14g), sodium hydroxide (9g), ethanol (165ml) and water (65ml) were stirred and refluxed for 2 hours. Water (100ml) was added and the product was allowed to crystallise overnight. The crystals were removed by filtration and washed with water and dried to give 3-methyl-8-oximino-5,6,7,8-tetrahydroquinoline (27.5g) mp 188° C. | Cc1cnc2c(c1)CCCC2=NO | null | NO | Cc1cnc2c(c1)CCCC2=O | null | [CH3:1][C:2]1[CH:3]=[N:4][C:5]2[C:6](=O)[CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1.Cl.[NH2:14][OH:15].[OH-].[Na+].C(O)C>O>[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[C:6](=[N:14][OH:15])[CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1 | null | CCO | 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 |
755,745 | O=C([O-])[O-] | [Cs+] | null | null | ord_dataset-1b0cd79134f0450eaac8396a4f956c30 | 2007-01-01T00:02:00 | true | 3-(4-Hydroxyphenyl)-2-methyl-2-phenoxypropionic acid ethyl ester (495 mg, 1.7 mmol) (see Ex. 1, Part C), toluene-4-sulfonic acid 2-[5-methyl-2-(3-thiophen-3-ylphenyl)oxazol-4-yl]ethyl ester (2.2 mmol) and Cs2CO3 (700 mg, 2.2 mmol) are combined in anhydrous DMF (25 mL) and stirred for 16 h at 55° C. under an atmosphere of nitrogen. The mixture was then cooled and diluted with ethyl acetate (100 mL), and washed with water then brine. The organic layer was dried with Na2SO4 and concentrated in vacuo to a viscous yellow oil. The residue was purified by flash column chromatography (100 g silica, 60×15 mL fractions, gradient elution 0–20% ethyl acetate in hexanes) to provide the title compound as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 8.23 (s, 1H), 7.90 (dt, J=7.6 Hz, J=1.2 Hz, 1H), 7.64 (dt, J=7.6 Hz, J=1.2 Hz, 1H), 7.56–7.55 (m, 1H), 7.48–7.39 (m, 3H), 7.23–7.14 (m, 5H), 6.96 (t, J=7.2 Hz, 1H), 6.83–6.81 (m, 4H), 4.24 (t, J=6.8 Hz, 2H), 4.12 (q, J=7.2 Hz, 2H), 3.26 (d, J=14.0 Hz, 1H), 3.10 (d, J=14.0 Hz, 1H), 3.00 (t, J=6.4 Hz, 2H), 2.39 (s, 3H), 1.38 (s, 3H) 1.21 (t, J=7.2 Hz, 3H); MS (EI) 568.2 (M+H)+. | CCOC(=O)C(C)(Cc1ccc(OCCc2nc(-c3cccc(-c4ccsc4)c3)oc2C)cc1)Oc1ccccc1 | null | CCOC(=O)C(C)(Cc1ccc(O)cc1)Oc1ccccc1 | Cc1ccc(S(=O)(=O)OCCc2nc(-c3cccc(-c4ccsc4)c3)oc2C)cc1 | null | [CH2:1]([O:3][C:4](=[O:22])[C:5]([CH3:21])([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[CH3:2].[CH3:23][C:24]1[O:28][C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([C:35]3[CH:39]=[CH:38][S:37][CH:36]=3)[CH:30]=2)=[N:26][C:25]=1[CH2:40][CH2:41]OS(C1C=CC(C)=CC=1)(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:22])[C:5]([CH3:21])([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:41][CH2:40][C:25]2[N:26]=[C:27]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([C:35]4[CH:39]=[CH:38][S:37][CH:36]=4)[CH:30]=3)[O:28][C:24]=2[CH3:23])=[CH:9][CH:8]=1)[CH3:2] | 16 | CCOC(C)=O | CN(C)C=O | null | 55 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,178,614 | null | null | null | null | ord_dataset-0f9d2dbe929a45c3892ae75e81e99443 | 2012-01-01T00:06:00 | true | The title compound was prepared following procedure described for example 35, step 1, but starting from Intermediate 36 (1 135.37 mg; 4.20 mmol) and Intermediate 1 (891.15 mg; 4.20 mmol). The reaction mixture was cooled to RT and concentrated affording yellow oil. It was precipitating in ACN. Solvent were removed and the solid was washed with MeOH, filtered off and dried under vacuum to afford the title compound as a white powder. 1H NMR (CDCl3) δ 8.43 (s, 1H), 8.18-7.99 (m, 4H), 7.41-7.35 (m, 3H), 7.29-7.24 (m, 1H), 7.11 (d, J=7.2 Hz, 1H), 4.27-4.17 (m, 2H), 3.98 (s, 3H), 3.34 (s, 3H), 2.50-2.28 (m, 2H), 1.05 (t, J=7.5 Hz, 3H). LC/MS (Method B): 447.2 (M+H)+. HPLC (Method A) Rt 6.14 min (Purity: 99.5%). | CCc1ccccc1-c1ccc(-c2nc(-c3ccc(C(=O)OC)c(F)c3)no2)cc1COC | null | CCc1ccccc1-c1ccc(C(=O)O)cc1COC | COC(=O)c1ccc(C(N)=NO)cc1F | null | [CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15](O)=O)=[CH:11][C:10]=1[CH2:18][O:19][CH3:20])[CH3:2].[NH2:21][C:22](=[N:34][OH:35])[C:23]1[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[C:25]([F:33])[CH:24]=1>>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:35][N:34]=[C:22]([C:23]3[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[C:25]([F:33])[CH:24]=3)[N:21]=2)=[CH:11][C:10]=1[CH2:18][O:19][CH3:20])[CH3:2] | null | 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 |
49,232 | CC(C)CCON=O | Cl | null | null | ord_dataset-0bb2e99daa66408fb8dbd6a0781d241c | 1978-01-01T00:12:00 | true | To a stirred solution of 7.49 g. of N-benzyloxycarbonyl-L-seryl-L-tyrosyl hydrazide [this compound is reported in Helv. Chim. Acta, 41, 1852 (1958)] in 50 ml. of N,N-dimethylformamide, cooled to -30° C., is first added 16.9 ml. of 3.607 N hydrogen chloride in tetrahydrofuran and then 2.7 ml. of isoamyl nitrite, and the resulting mixture is stirred at -30° C. for 30 minutes. The mixture, which contains N-benzyloxycarbonyl-L-seryl-L-tyrosyl azide, is next cooled to -60° C., and to it are added first 8.57 ml. of triethylamine, then 4.297 g. of glycyl-L-leucine methyl ester hydrochloride and finally 2.52 ml. more of triethylamine. The stirred mixture is allowed to warm to 0° C. during one hour and is stirred at 0° C. for one hour and kept at -5° C. for 48 hours. It is then filtered, and the filtrate is evaporated under reduced pressure at 40°-50° C. The gummy residue is partitioned between dilute hydrochloric acid and ethyl acetate, and the organic layer is separated, washed with saturated aqueous sodium bicarbonate and with saturated aqueous sodium chloride, dried, and evaporated to give a solid residue of N-benzyloxycarbonyl-L-seryl-L-tyrosylglycyl-L-leucine methyl ester; m.p. 166°-167° C., following two crystallizations from ethyl acetate-ether; [α]D25 -25.4° (2% in N,N-dimethylformamide); [α]D25 -38.2° (2.09% in methanol). | COC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](CO)NC(=O)OCc1ccccc1 | null | [N-]=[N+]=NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](CO)NC(=O)OCc1ccccc1 | COC(=O)[C@H](CC(C)C)NC(=O)CN | null | Cl.N(OCCC(C)C)=O.[CH2:10]([O:17][C:18]([NH:20][C@H:21]([C:24]([NH:26][C@H:27]([C:36]([N:38]=[N+]=[N-])=[O:37])[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1)=[O:25])[CH2:22][OH:23])=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl.[CH3:42][O:43][C:44](=[O:55])[C@H:45]([CH2:51][CH:52]([CH3:54])[CH3:53])[NH:46][C:47](=[O:50])[CH2:48]N>O1CCCC1.C(N(CC)CC)C.CN(C)C=O>[CH3:42][O:43][C:44](=[O:55])[C@H:45]([CH2:51][CH:52]([CH3:53])[CH3:54])[NH:46][C:47](=[O:50])[CH2:48][NH:38][C:36](=[O:37])[C@H:27]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1)[NH:26][C:24](=[O:25])[C@H:21]([CH2:22][OH:23])[NH:20][C:18]([O:17][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:19] | 1 | CN(C)C=O | CCN(CC)CC | C1CCOC1 | -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 |
1,161,379 | [Br-] | [H-] | [Na+] | null | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | 2012-01-01T00:05:00 | true | To a solution of diethyl methylmalonate (5.19 g) in 100 mL of THF was added NaH (1.2 g, 60%) at 0° C. in portions. The mixture was stirred at 0° C. for 10 min, and to this solution was then added the bromide intermediate (3.84 g) in one portion. The mixture was warmed to 23° C. and stirred for 1 h before the addition of water. The resulting mixture was extracted with ethyl acetate, concentrated and purified by Biotage (5-10% ethyl acetate in hexane) to give the diester containing some diethyl methyl malonate contaminant as a crude oil. | CCOC(=O)C(CC)C(=O)OC | null | CCOC(=O)C(C)C(=O)OCC | C1CCOC1 | null | [CH3:1][CH:2]([C:8]([O:10][CH2:11]C)=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].[Br-].O.[CH2:17]1COCC1>>[CH3:17][CH2:1][CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:8]([O:10][CH3:11])=[O:9] | 0.17 | O | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
471,454 | Cl[Ti](Cl)(Cl)Cl | null | null | null | ord_dataset-cd531114850e4f239b2a3661044ae672 | 2000-01-01T00:08:00 | true | To a solution of 17.7 g of the 2-ethyl-2,4,5,7-tetramethylindane in 100 ml of dry dichloromethane was continuously added 9.5 ml of α,α-dichloromethyl methyl ether and 11.6 ml of TiCl4 at 0° C. The reaction mixture was stirred at room temperature for 2 hours, quenched with 200 ml of water, and separated the organic layer. The aqueous layer was extracted with dichloromethane. The combined organic layer was dried over magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by silica-gel column chromatography to afford 18.26 g of the title compound as brown solid. | CCC1(C)Cc2c(C)c(C)c(C=O)c(C)c2C1 | null | COC(Cl)Cl | CCC1(C)Cc2c(C)cc(C)c(C)c2C1 | null | [CH2:1]([C:3]1([CH3:15])[CH2:11][C:10]2[C:5](=[C:6]([CH3:14])[CH:7]=[C:8]([CH3:13])[C:9]=2[CH3:12])[CH2:4]1)[CH3:2].[CH3:16][O:17]C(Cl)Cl>ClCCl.Cl[Ti](Cl)(Cl)Cl>[CH2:1]([C:3]1([CH3:15])[CH2:11][C:10]2[C:5](=[C:6]([CH3:14])[C:7]([CH:16]=[O:17])=[C:8]([CH3:13])[C:9]=2[CH3:12])[CH2:4]1)[CH3:2] | 2 | ClCCl | null | null | 25 | 90 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
755,881 | null | null | null | null | ord_dataset-1b0cd79134f0450eaac8396a4f956c30 | 2007-01-01T00:02:00 | true | A solution of methanesulphonic anhydride (8.33 g, 47.8 mmol) in dichloromethane (30 ml) was added dropwise over 30 minutes to an ice-cooled solution of (R)-2-butanol (4.0 ml, 43.5 mmol) and triethylamine (6.65 ml, 47.8 mmol) in dichloromethane (70 ml). The reaction was then allowed to warm to room temperature and stirred for 18 hours. The mixture was then washed with water, 2N hydrochloric acid, then dried (Na2SO4) and evaporated under reduced pressure to give the title compound as a pale yellow oil, 7.0 g. | CC[C@@H](C)OS(C)(=O)=O | null | CS(=O)(=O)OS(C)(=O)=O | CC[C@@H](C)O | null | [CH3:1][S:2]([O:5]S(C)(=O)=O)(=[O:4])=[O:3].[CH3:10][C@@H:11](O)[CH2:12][CH3:13].C(N(CC)CC)C>ClCCl>[CH3:1][S:2]([O:5][C@H:11]([CH3:10])[CH2:12][CH3:13])(=[O:4])=[O:3] | 18 | CCN(CC)CC | ClCCl | 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 |
417,979 | [Al+3] | [H-] | [Li+] | null | ord_dataset-94e21e9990034c729ea727e7d2ab0eb0 | 1998-01-01T00:12:00 | true | 1840 mg of (2R,4R)-1-ethoxycarbonyl-4-hydroxy-2-{2-[6-methyl-2-(2-phenylethyl)phenoxy]ethyl}pyrrolidine [prepared as described in step (b) above], 20 ml of tetrahydrofuran and 530 mg of lithium aluminum hydride were allowed to react together and subsequently treated in the same manner as described in step (b) of Example 1. The concentrated substance thus obtained was purified by silica gel column chromatography, using a 5:1 by volume mixture of methylene chloride and methanol as the eluent, to give 1050 mg (yield 67%) of the title compound as a colorless solid substance. | Cc1cccc(CCc2ccccc2)c1OCC[C@@H]1C[C@@H](O)CN1C | null | CCOC(=O)N1C[C@H](O)C[C@H]1CCOc1c(C)cccc1CCc1ccccc1 | null | null | C(O[C:4]([N:6]1[CH2:10][C@H:9]([OH:11])[CH2:8][C@H:7]1[CH2:12][CH2:13][O:14][C:15]1[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[OH:11][C@H:9]1[CH2:10][N:6]([CH3:4])[C@H:7]([CH2:12][CH2:13][O:14][C:15]2[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][C:16]=2[CH2:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:8]1 | null | C1CCOC1 | null | null | null | null | 66.8 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
598,946 | null | null | null | null | ord_dataset-82e842e611ef4a05b6e7f9ea0a46d52d | 2003-01-01T00:07:00 | true | A mixture of (R)-7-ethoxymethyl-1-(5-hydroxyhexyl)-8-mercapto-3-methylxanthine (0.19 g, 0.533 mmol) potassium carbonate (0.15 g, 10.7 mmol) and 1-bromo-2-chloroethane (114 mg, 0.80 mmol) in acetonitrile (10 ml) was stirred at 65° C. for 1.5 hours. After concentrating under reduced pressure, the residue was purified by column chromatography on silica gel eluting with ethyl acetate-hexane (1:1) to provide (R)-7-ethoxymethyl-8-(2-chloroethylsulfanyl)-1-(5-hydroxyhexyl)-3-methylxanthine (150 mg, 67% yield) as a white powder. | CCOCn1c(SCCCl)nc2c1c(=O)n(CCCC[C@@H](C)O)c(=O)n2C | null | ClCCBr | CCOCn1c(S)nc2c1c(=O)n(CCCC[C@@H](C)O)c(=O)n2C | null | [CH2:1]([O:3][CH2:4][N:5]1[C:13]2[C:12](=[O:14])[N:11]([CH2:15][CH2:16][CH2:17][CH2:18][C@H:19]([OH:21])[CH3:20])[C:10](=[O:22])[N:9]([CH3:23])[C:8]=2[N:7]=[C:6]1[SH:24])[CH3:2].Br[CH2:26][CH2:27][Cl:28]>C(#N)C>[CH2:1]([O:3][CH2:4][N:5]1[C:13]2[C:12](=[O:14])[N:11]([CH2:15][CH2:16][CH2:17][CH2:18][C@H:19]([OH:21])[CH3:20])[C:10](=[O:22])[N:9]([CH3:23])[C:8]=2[N:7]=[C:6]1[S:24][CH2:26][CH2:27][Cl:28])[CH3:2] | 1.5 | CC#N | null | null | 65 | null | 67.2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,689,561 | Br[Mg]CCC1CC1 | II | [Mg] | null | ord_dataset-c1e70ad912eb438f8d34b1dc681f809a | 2016-01-01T00:02:00 | true | Magnesium metal (39.0 mg, 2.0 mmol) and iodine (one crystal) was taken up in dry diethyl ether (1.2 mL) and (2-bromoethyl)cyclopropane (200 mg, 1.3 mmol) was added dropwise until iodine color faded. The remainder was then added dropwise over 15 minutes to maintain a gentle reflux and then cooled to 0° C. (2-cyclopropylethyl)magnesium bromide (1.1 M, 0.38 mL, 0.41 mmol) was added to a cooled (0° C.) solution of (6-(3,5-dimethylisoxazol-4-yl)-2-ethoxy-1H-benzo[d]imidazol-4-yl)(pyridin-2-yl)methanone (50 mg, 0.14 mmol) in dry THF (1.0 mL) under argon and allowed to stir for 10 minutes. The reaction was quenched with water, extracted three times with EtOAc, and combined organic layers were concentrated and purified by reverse-phase HPLC to give 3-cyclopropyl-1-(6-(3,5-dimethylisoxazol-4-yl)-2-ethoxy-1H-benzo[d]imidazol-4-yl)-1-(pyridin-2-yl)propan-1-ol intermediate. The intermediate was taken up in EtOH (1.5 mL) and 0.2 mL concentrated HCl and heated to 65° C. for 2 hours and concentrated to afford the desired product as a white powder. | CCOc1nc2c(C(O)(CCC3CC3)c3ccccn3)cc(-c3c(C)noc3C)cc2[nH]1 | null | BrCCC1CC1 | CCOc1nc2c(C(=O)c3ccccn3)cc(-c3c(C)noc3C)cc2[nH]1 | null | [Mg].II.Br[CH2:5][CH2:6][CH:7]1[CH2:9][CH2:8]1.C1(CC[Mg]Br)CC1.[CH3:17][C:18]1[C:22]([C:23]2[CH:24]=[C:25]([C:35]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=3)=[O:36])[C:26]3[N:30]=[C:29]([O:31][CH2:32][CH3:33])[NH:28][C:27]=3[CH:34]=2)=[C:21]([CH3:43])[O:20][N:19]=1>C(OCC)C.C1COCC1>[CH:7]1([CH2:6][CH2:5][C:35]([C:25]2[C:26]3[N:30]=[C:29]([O:31][CH2:32][CH3:33])[NH:28][C:27]=3[CH:34]=[C:23]([C:22]3[C:18]([CH3:17])=[N:19][O:20][C:21]=3[CH3:43])[CH:24]=2)([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=2)[OH:36])[CH2:9][CH2:8]1 | 0.17 | CCOCC | 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 |
335,834 | null | null | null | null | ord_dataset-65c44df6676d4ce3a1874db5d7958ca9 | 1996-01-01T00:08:00 | true | In accordance with the general procedure described in Example 1, reaction of 10 g (0.055 mol) of 3-dimethylamino-(3-thienyl)-2-propen-1-one [described in EP-A-0 233 461] and 15 g (0.060 mol) of 3-(1,1,2,2-tetrafluoroethoxy)phenylguanidine nitrate gives N-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]-4-(3-thienyl)-2-pyrimidine-amine; FAB-MS:370 (M+ +1), m.p. 110°-111°, Rf =0.8 (ethyl acetate:hexane=1:1). | FC(F)C(F)(F)Oc1cccc(Nc2nccc(-c3ccsc3)n2)c1 | null | CN(C)C=CC(=O)c1ccsc1 | N=C(N)Nc1cccc(OC(F)(F)C(F)F)c1 | null | CN(C)[CH:3]=[CH:4][C:5]([C:7]1[CH:11]=[CH:10][S:9][CH:8]=1)=O.[N+]([O-])(O)=O.[F:17][C:18]([F:33])([O:22][C:23]1[CH:24]=[C:25]([NH:29][C:30]([NH2:32])=[NH:31])[CH:26]=[CH:27][CH:28]=1)[CH:19]([F:21])[F:20]>>[F:17][C:18]([F:33])([O:22][C:23]1[CH:24]=[C:25]([NH:29][C:30]2[N:32]=[C:5]([C:7]3[CH:11]=[CH:10][S:9][CH:8]=3)[CH:4]=[CH:3][N:31]=2)[CH:26]=[CH:27][CH:28]=1)[CH:19]([F:20])[F:21] | null | O=[N+]([O-])O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,687,187 | null | null | null | null | ord_dataset-c1e70ad912eb438f8d34b1dc681f809a | 2016-01-01T00:02:00 | true | 6-Bromo-5-(2,4-difluorophenyl)-1,2,4-triazin-3-amine (0.13 g, 21%) was prepared from 5-(2,4-difluorophenyl)-1,2,4-triazin-3-amine (0.45 g, 2.1 mmol) and N-bromosuccinimide (0.49 g, 2.80 mmol) according to the general procedure of Preparation 3. | Nc1nnc(Br)c(-c2ccc(F)cc2F)n1 | null | O=C1CCC(=O)N1Br | Nc1nncc(-c2ccc(F)cc2F)n1 | null | [F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([NH2:15])[N:12]=[N:13][CH:14]=1.[Br:16]N1C(=O)CCC1=O>>[Br:16][C:14]1[N:13]=[N:12][C:11]([NH2:15])=[N:10][C:9]=1[C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[F:1] | null | null | null | null | null | null | 21.6 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,041,833 | [Fe] | [Cl-] | [NH4+] | null | ord_dataset-3af92aec23dc4810b92eb0d8c60023ee | 2011-01-01T00:03:00 | true | The product from Example 255b was reduced with Fe and NH4Cl following the procedure from Example 9E to provide the title compound (980 mg, 90%). | Nc1cc(NC(=O)c2ccco2)ccc1Sc1ccc(O)cc1 | null | O=C(Nc1ccc(Sc2ccc(O)cc2)c([N+](=O)[O-])c1)c1ccco1 | null | null | [OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]3[O:19][CH:20]=[CH:21][CH:22]=3)=[O:17])=[CH:11][C:10]=2[N+:23]([O-])=O)=[CH:4][CH:3]=1.[NH4+].[Cl-]>[Fe]>[NH2:23][C:10]1[CH:11]=[C:12]([NH:15][C:16]([C:18]2[O:19][CH:20]=[CH:21][CH:22]=2)=[O:17])[CH:13]=[CH:14][C:9]=1[S:8][C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=1 | null | null | null | null | null | 90 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
314,192 | CC[O-] | [Na+] | null | null | ord_dataset-bd998d3fe946475e835418aaf647c00d | 1995-01-01T00:08:00 | true | Add 0.5 cm3 of a molar solution of sodium ethanolate in ethanol to a solution of 1 g (3.78 mmol) of ethyl 7-acetoxy-1,4-benzodioxin-2-carboxylate in 15 cm3 of anhydrous ethanol under a nitrogen atmosphere. Stir for 18 hours at room temperature and then neutralise with Dowex X-8 resin, acid form, which has been washed beforehand with ethanol. After filtration and concentration to dryness under partial pressure, the crude product obtained is purified by chromatography on a silica column (eluant: petroleum ether/diethyl ether, 80:20). Ethyl 7-hydroxy-1,4-benzodioxin-2-carboxylate is thereby obtained in a yield of 96%. Melting point: 160° C. ##STR43## | CCOC(=O)C1=COc2ccc(O)cc2O1 | null | CCOC(=O)C1=COc2ccc(OC(C)=O)cc2O1 | null | null | C([O-])C.[Na+].C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[O:17][CH:16]=[C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[O:14][C:13]=2[CH:23]=1)(=O)C>C(O)C>[OH:8][C:9]1[CH:10]=[CH:11][C:12]2[O:17][CH:16]=[C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[O:14][C:13]=2[CH:23]=1 | 18 | CCO | null | null | 25 | 96 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,662,644 | CCCCCCCCc1ccc(NC(=O)NCCC(=O)OCC)cc1 | null | null | null | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | 2015-01-01T00:11:00 | true | When the product of Step D was substituted for ethyl 3-(3-(4-octylphenyl)ureido)propanoate in Example 11, Step B, the identical process afforded the title compound in 84% yield, as a colourless solid. 1H-NMR (CDCl3) 7.68 (d, 1H, J=8.7 Hz); 6.94 (m, 2H); 5.24 (t, 1H, J=5.9 Hz); 3.86 (t, 2H, J=8.7 Hz); 3.58 (q, 2H, J=5.9 Hz); 3.11 (t, 2H, J=8.5 Hz); 2.67 (t, 2H, J=5.8 Hz); 2.5 (t, 2H, J=8 Hz); 1.54 (m, 2H); 1.25 (m, 10H); 0.86 (t, 3H, J=6.8 Hz). | CCCCCCCCc1ccc2c(c1)CCN2C(=O)NCCC(=O)O | null | CCCCCCCCc1ccc2c(c1)CCN2C(=O)NCCC(=O)OCC | null | null | [CH2:1]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:18]([NH:20][CH2:21][CH2:22][C:23]([O:25]CC)=[O:24])=[O:19])[CH2:13][CH2:12]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(C1C=CC(NC(=O)NCCC(OCC)=O)=CC=1)CCCCCCC>>[CH2:1]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:18]([NH:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[O:19])[CH2:13][CH2:12]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8] | null | null | null | null | null | 84 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
646,093 | Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1 | I[Cu]I | null | null | ord_dataset-c975a50a7600448fabd558f4a94a3e29 | 2004-01-01T00:08:00 | true | Under an argon atmosphere, 40 g (0.155 mol) of 9-bromoanthracene, 3.3 g (4.6 mmol) of bis(triphenylphosphine)palladium(II) dichloride and 0.87 g (3 mmol) of copper Iodide were dissolved in 500 ml of diisopropylamine in a 1 L 3-necked flask equipped with a stirrer, thermometer and reflux condenser. 23 g (0.233 mol) of trimethylsilyl acetylene was then slowly dropped into the resulting mixture at room temperature. The reaction mixture was slowly heated to 80° C. and refluxed for 12 hours. After the reaction was completed, the reaction mixture was cooled down to room temperature, and then the precipitated salt was filtered off. The solvent was removed under a reduced pressure, and then the residue was dissolved in methylene chloride. The organic layer was washed with water several times and then dried with anhydrous magnesium sulfate. The solvent was removed to obtain orange-colored liquid, which was purified by silica gel column chromatography using hexane as an eluent, and then recrystallized from ethanol to give yellow crystal. The yellow crystal was recovered and sufficiently dried in a vacuum oven at 40° C., to give 32 g (83.3% yield) of the desired product having a melting point of 66-68° C. | C#Cc1cccc2cc3ccccc3c([Si](C)(C)C)c12 | null | C#C[Si](C)(C)C | Brc1c2ccccc2cc2ccccc12 | null | Br[C:2]1[C:3]2[C:8]([CH:9]=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[CH3:16][Si:17]([C:20]#[CH:21])([CH3:19])[CH3:18]>C(NC(C)C)(C)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I>[CH3:16][Si:17]([CH3:19])([CH3:18])[C:20]1[C:4]2[C:3]([CH:2]=[C:15]3[C:21]=1[C:11]([C:10]#[CH:9])=[CH:12][CH:13]=[CH:14]3)=[CH:8][CH:7]=[CH:6][CH:5]=2 | null | CC(C)NC(C)C | null | null | 80 | null | 75.2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,585,356 | [Cl-] | [NH4+] | null | null | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | 2015-01-01T00:05:00 | true | To a solution of tert-butyl-3-(3,5-difluorophenyl)-3-methoxypyrrolidin-1-carboxylate (2.64 g, 8.4 mmol) in methylene chloride (20 mL), was added trifluoroacetic acid (5 mL). The mixture was stirred for 1 h at ambient temperature after which aqueous saturated ammonium chloride solution (50 ml) was added and the aqueous phase was extracted with methylene chloride (2×50 mL). The combined organic phase was dried (Na2SO4), filtered and evaporated to give the crude product, purification on a Biotage Isolute SCX-3 SPE column (washed with methanol and eluted with methanol/triethylamine, 4:1) gave the title compound (1.3 g, 73%). MS m/z (rel. intensity, 70 eV) 213 (M+, 0.5), 183 (bp), 171 (89), 141 (80), 113 (88). | COC1(c2cc(F)cc(F)c2)CCNC1 | null | COC1(c2cc(F)cc(F)c2)CCN(C(=O)OC(C)(C)C)C1 | null | null | C(OC([N:8]1[CH2:12][CH2:11][C:10]([C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([F:22])[CH:16]=2)([O:13][CH3:14])[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.[Cl-].[NH4+]>C(Cl)Cl>[F:22][C:17]1[CH:16]=[C:15]([C:10]2([O:13][CH3:14])[CH2:11][CH2:12][NH:8][CH2:9]2)[CH:20]=[C:19]([F:21])[CH:18]=1 | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | 72.6 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
402,942 | [Na] | null | null | null | ord_dataset-7fed188163cf4ccca934ec71504c7f8a | 1998-01-01T00:05:00 | true | There was dissolved 15.0 g (0.0604 mol) of 3-[3-(piperidinomethyl)phenoxy]propylamine in 150 ml of dichloromethane and added dropwise 6. 82 g (0.0604 mol) of chloroacetyl chloride under cooling with ice. After dropping, the mixture was stirred for 3.5 hours under cooling with ice and then the solvent was removed under reduced pressure. The residue was dissolved in 150 ml of ethanol and this solution was added to a solution which was prepared by adding 4.65 g (0.0604 mol) of 2-aminoethanethiol to a solution of 3.06 g (0.1329 mol) of sodium 150 ml of ethanol and stirring for 30 minutes at room temperature, and the obtained mixture was refluxed with heating for 3 hours. After being allowed to cool at room temperature, the precipitate was filtrated off, and the solvent was removed under reduced pressure. The obtained residue was dissolved in ethyl acetate and washed with water, and dried over Glauber's salt. Then the solvent was removed under reduced pressure to give 20.4 g of the titled compound as oily matter. | NCCSCC(=O)NCCCOc1cccc(CN2CCCCC2)c1 | null | NCCS | O=C(Cl)CCl | NCCCOc1cccc(CN2CCCCC2)c1 | [N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[O:11][CH2:12][CH2:13][CH2:14][NH2:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[CH2:20][C:21](Cl)=[O:22].[NH2:24][CH2:25][CH2:26][SH:27].[Na]>ClCCl.C(O)C>[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[O:11][CH2:12][CH2:13][CH2:14][NH:15][C:21](=[O:22])[CH2:20][S:27][CH2:26][CH2:25][NH2:24])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1 | 3.5 | CCO | ClCCl | null | 25 | 92.4 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
295,844 | CS(=O)(=O)[O-] | [H-] | [Na+] | null | ord_dataset-ec7cb3d5a8704f64b01d401ea555974f | 1994-01-01T00:09:00 | true | A stirred mixture of 4-hydroxy-alpha-oxobenzeneacetic acid methyl ester (0.724 g) in dimethylformamide (10 mL) under argon was treated with 55% sodium hydride (0.175 g), stirred for 15 minutes and treated with the mesylate of 2-(3,4-dimethoxyphenoxy)ethanol (1.65 g). The mixture was heated at 60° C. overnight and worked up as in Example 20. The material was purified by HPLC (dichloromethane-diethyl ether, 99:1) and crystallized from dichloromethane-hexane to provide 0.9 g of 4-[[2-(3,4-dimethoxyphenoxy)ethyl]oxy]-alpha-oxobenzeneacetic acid methyl ester, mp 93°-94° C. | COC(=O)C(=O)c1ccc(OCCOc2ccc(OC)c(OC)c2)cc1 | null | COC(=O)C(=O)c1ccc(O)cc1 | COc1ccc(OCCO)cc1OC | null | [CH3:1][O:2][C:3](=[O:13])[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[H-].[Na+].S([O-])(=O)(=O)C.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH:30]=[CH:31][C:32]=1[O:33][CH3:34])[O:26][CH2:27][CH2:28]O>CN(C)C=O>[CH3:1][O:2][C:3](=[O:13])[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:28][CH2:27][O:26][C:25]2[CH:30]=[CH:31][C:32]([O:33][CH3:34])=[C:23]([O:22][CH3:21])[CH:24]=2)=[CH:7][CH:6]=1 | 0.25 | CN(C)C=O | null | null | 60 | 62.1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
660,273 | Br | null | null | null | ord_dataset-04d607efe1d9485eb99fafa06880f62e | 2005-01-01T00:02:00 | true | A mixture of N-(4-chlorobenzyl)-2-(chloromethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide (100 mg, 0.25 mmol), 2-(methylamino)-1-pyridin-3-ylethanol hydrobromide (Arch. Pharm. 1961, 294 453-68)(89 mg, 0.38 mmol) and diisopropylethylamine (134 μL, 0.76 mmol) in dry DMF (5.0 mL) was stirred for 30 hours at room temperature. The solution was diluted with water (15 mL). The resulting milky suspension was stirred vigorously for 30 minutes, and then left standing overnight at room temp. The mixture was filtered, and the collected solid was washed with water and dried in vacuo, leaving a white solid. Recrystallization from acetonitrile (10 mL, dissolved with warming and then cooled to 0° C. overnight) gave the title compound (87 mg) as a white solid. | Cc1c(CN(C)CC(O)c2cccnc2)sc2c(=O)c(C(=O)NCc3ccc(Cl)cc3)cn(C)c12 | null | CNCC(O)c1cccnc1 | Cc1c(CCl)sc2c(=O)c(C(=O)NCc3ccc(Cl)cc3)cn(C)c12 | null | [Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:23])[C:12]3[S:19][C:18]([CH2:20]Cl)=[C:17]([CH3:22])[C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1.Br.[CH3:27][NH:28][CH2:29][CH:30]([C:32]1[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=1)[OH:31].C(N(C(C)C)CC)(C)C>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:23])[C:12]3[S:19][C:18]([CH2:20][N:28]([CH2:29][CH:30]([OH:31])[C:32]4[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=4)[CH3:27])=[C:17]([CH3:22])[C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:24][CH:25]=1 | 30 | O | CN(C)C=O | CCN(C(C)C)C(C)C | 25 | null | 68.1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
637,202 | Cl | null | null | null | ord_dataset-a192df1b44174b5886ef2005f759d553 | 2004-01-01T00:05:00 | true | 0.10 g (0.20 mMol) 4-{4-methoxy-2-[(2-methoxy-pyridine-4-carbonyl)-amino]-benzothiazol-7-yl}-piperidine-1-carboxylic acid tert-butyl ester were dissolved in 2 ml 2.5 M HCl/MeOH and heated to reflux for 1.5 h. The reaction mixture was concentrated in vacuo and taken up in 3 ml isopropanol. The suspension formed was filtered and the material on the filter was washed with diethyl ether and dried in vacuo. One obtained 0.075 g (86%) 2-methoxy-N-(4-methoxy-7-piperidin-4-yl-benzothiazol-2-yl)-isonicotinamide 1:2 hydrochloride as a yellow solid. F.p.: 305-310° C. | COc1cc(C(=O)Nc2nc3c(OC)ccc(C4CCNCC4)c3s2)ccn1 | null | COc1cc(C(=O)Nc2nc3c(OC)ccc(C4CCN(C(=O)OC(C)(C)C)CC4)c3s2)ccn1 | null | null | C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:22]3[S:21][C:20]([NH:23][C:24]([C:26]4[CH:31]=[CH:30][N:29]=[C:28]([O:32][CH3:33])[CH:27]=4)=[O:25])=[N:19][C:18]=3[C:17]([O:34][CH3:35])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>Cl.CO>[CH3:33][O:32][C:28]1[CH:27]=[C:26]([CH:31]=[CH:30][N:29]=1)[C:24]([NH:23][C:20]1[S:21][C:22]2[C:14]([CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[CH:15][CH:16]=[C:17]([O:34][CH3:35])[C:18]=2[N:19]=1)=[O:25] | null | CO | null | null | null | 94.1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
546,206 | O=S(=O)([O-])O | [K+] | null | null | ord_dataset-d31180f42ced44719fd9e72685c798bf | 2002-01-01T00:05:00 | true | First, 9.39 g of 4-(1-hydroxyethyl)-4′-(trans-4-pentylcyclohexyl)biphenyl, 0.52 g of potassium hydrogensulfate, and 50 ml of toluene were put in a 300 ml flask provided with a water content quantitative tube, and subjected to azeotropic dehydration under reflux for four hours. After the reaction, ether was added to the reaction solution, which was then washed with a saturated brine, and dried with sodium sulfate. The solvent was then distilled off. The residue was recrystallized from hexane to obtain 1.88 g (Y: 21.1%) of 4-(trans-4-pentylcyclohexyl)vinylbiphenyl. The purity of the resultant compound was 100.0% as measured by GC, 99.9% as measured by HPLC, and 1 spot as measured by TLC. The phase transfer temperature of the resultant compound was as follows. | CCCCC[C@H]1CC[C@H](C=Cc2ccc(-c3ccccc3)cc2)CC1 | null | Cc1ccccc1 | CCCCC[C@H]1CC[C@H](c2ccc(-c3ccc(C(C)O)cc3)cc2)CC1 | null | OC([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C@H:16]3CC[C@H](CCCCC)C[CH2:17]3)=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)C.S([O-])(O)(=O)=O.[K+].[C:33]1([CH3:39])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CCOCC>[CH2:39]([C@H:33]1[CH2:38][CH2:37][C@H:36]([CH:17]=[CH:16][C:13]2[CH:12]=[CH:11][C:10]([C:7]3[CH:8]=[CH:9][CH:4]=[CH:5][CH:6]=3)=[CH:15][CH:14]=2)[CH2:35][CH2:34]1)[CH2:9][CH2:4][CH2:5][CH3:6] | null | CCOCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,472,493 | CNC | CS(=O)(=O)Cl | null | null | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | 2014-01-01T00:08:00 | true | To a solution of methyl 2-(hydroxymethyl)-2′-methylbiphenyl-4-carboxylate (2.12 g, 8.27 mmol) in DCM (65 mL) was added DIEA (7.03 mL, 41.4 mmol) and methanesulfonyl chloride (768 μL, 9.93 mmol) at 0° C. and stirred for 25 min. After this time, a 2M solution of dimethylamine in THF (12.4 mL, 24.8 mmol) was added and the resulting mixture was stirred at RT for 16 hours. The reaction mixture was partitioned between DCM and a 5N aqueous solution of NaOH. The organic layer was dried (MgSO4) and concentrated under vacuum. A purification by chromatography (silica, DCM/MeOH) gave the title compound as a light yellow solid (2.03 g, 86%). 1H NMR (DMSO-d6) δ 8.27 (d, J=1.4 Hz, 1H), 7.95 (dd, J=7.8, 1.9 Hz, 1H), 7.32-7.18 (m, 4H), 7.06 (d, J=7.3 Hz, 1H), 3.94 (s, 3H), 3.24-3.10 (m, 2H), 2.11 (s, 6H), 2.01 (s, 3H). HPLC (Method A) Rt 2.90 min (Purity 100.0%). LC/MS (Method B): 284.1 (M−H)−. | COC(=O)c1ccc(-c2ccccc2C)c(CN(C)C)c1 | null | CCN(C(C)C)C(C)C | COC(=O)c1ccc(-c2ccccc2C)c(CO)c1 | null | O[CH2:2][C:3]1[CH:8]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][C:4]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19].C[CH2:21][N:22](C(C)C)[CH:23](C)C.CS(Cl)(=O)=O.CNC.C1COCC1>C(Cl)Cl>[CH3:21][N:22]([CH2:2][C:3]1[CH:8]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][C:4]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19])[CH3:23] | 0.42 | C1CCOC1 | ClCCl | null | null | null | 86.6 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
555,512 | CC(C)(O)C#N | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | ord_dataset-ec9decb576c4424c9685993f6262bd9c | 2002-01-01T00:07:00 | true | Diethylazodicarboxylate (5.2 g) is added dropwise to a solution of 4-bromo-phenethylalcohol (2.01 g), and triphenylphosphine (7.9 g) in diethyl ether (16 mL) at 0° C. The reaction mixture is stirred for 10 minutes and a solution of acetone cyanohydrin (2.6 g) in diethyl ether (10 mL) is added. The clear orange solution is stirred for 5 minutes at 0° C. and then at 25° C. for 12 hours. The reaction mixture is then filtered, and washed with diethyl ether. The filtrate is concentrated under reduced pressure and chromatographed over silica gel (10% ethyl acetate-hexanes is used as the eluant) to provide the desired product as a pale yellow oil (2.04 g). | N#CCCc1ccc(Br)cc1 | null | OCCc1ccc(Br)cc1 | CCOC(=O)/N=N/C(=O)OCC | null | CCO[C:4](/[N:6]=N/C(OCC)=O)=O.[Br:13][C:14]1[CH:22]=[CH:21][C:17]([CH2:18][CH2:19]O)=[CH:16][CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)(O)C#N>C(OCC)C>[Br:13][C:14]1[CH:22]=[CH:21][C:17]([CH2:18][CH2:19][C:4]#[N:6])=[CH:16][CH:15]=1 | 0.17 | CCOCC | null | null | null | null | 97.1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
321,565 | O=[Pt] | null | null | null | ord_dataset-eed8d32c2f1d46a89ba39d04dfaa83b1 | 1995-01-01T00:12:00 | true | 5.3 gm of methyl 18-methyl-16-eicosenoate charged into an autoclave together with 0.3 gm of platinum oxide and 30 ml of acetic acid were reduced under 100 atm hydrogen pressure at 100° C. for 5 hours. After the reaction, the catalyst was removed by filtration and the solvent was evaporated to obtain 3 gm of methyl 18-methyleicosanoate, which was purified by flash column chromatography (chloroform). The product was dissolved into 150 ml of a 5% sodium hydroxide-ethanol solution and stirred at room temperature for 8 hours. Then, 95 ml of 2N sulfuric acid was added to obtain a solid. The solid material was filtered and washed with water to obtain 3.1 gm of 18-methyleicosanoic acid (yield: 59% from methyl 18-methyl-16-eicosenoate). | CCC(C)CCCCCCCCCCCCCCCCC(=O)OC | null | [H][H] | CCC(C)C=CCCCCCCCCCCCCCCC(=O)OC | null | [CH3:1][CH:2]([CH2:23][CH3:24])[CH:3]=[CH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20].[H][H]>[Pt]=O.C(O)(=O)C>[CH3:1][CH:2]([CH2:23][CH3:24])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20] | null | CC(=O)O | null | null | null | 56.3 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,231,133 | null | null | null | null | ord_dataset-e96f5a2842f14e5380461c234100f05a | 2012-01-01T00:12:00 | true | Heat 259.8 mg (0.771 mmol) of 4-chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine and 228 mg of 4-(2-aminophenyl)butanoic acid methyl ester (85% strength, approx. 1.0 mmol) to 150° C. overnight. After cooling, concentrate under reduced pressure, add dichloromethane to the residue and purify the crude product by chromatography on silica gel (eluent: dichloromethane/ethyl acetate 50:1→10:1). The product thus obtained is purified further by preparative RP-HPLC. 33.1 mg (8.7% of theory) of the target product are obtained. | COC(=O)CCCc1ccccc1Nc1ncnc2oc(-c3ccccc3)c(-c3ccc(OC)cc3)c12 | null | COC(=O)CCCc1ccccc1N | COc1ccc(-c2c(-c3ccccc3)oc3ncnc(Cl)c23)cc1 | null | Cl[C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[C:9]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[O:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH3:25][O:26][C:27](=[O:38])[CH2:28][CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[NH2:37]>>[CH3:25][O:26][C:27](=[O:38])[CH2:28][CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[NH:37][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[C:9]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[O:8][C:4]=2[N:5]=[CH:6][N:7]=1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
271,468 | null | null | null | null | ord_dataset-347c0709d28a44dea43ca42052be4db3 | 1993-01-01T00:07:00 | true | To N-(1-benzyl-4-piperidinyl)-2-formyl-3-methylaniline (7.0 g) are added methanol (100 ml) and methyl (triphenylphosphoranylidene)acetate (15 g) and the mixture is refluxed for 1 hour. After cooling, the formed crystals are separated by filtration to give methyl 2-methyl-5-[(1-benzyl-4-piperidinyl)amino]cinnamate (5.6 g) as pale yellow powders, m.p. 140°-142° C. | COC(=O)C=Cc1cc(NC2CCN(Cc3ccccc3)CC2)ccc1C | null | Cc1cccc(NC2CCN(Cc3ccccc3)CC2)c1C=O | COC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1 | CO | [CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:16]=2C=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(=[CH:43][C:44]([O:46][CH3:47])=[O:45])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:48]O>>[CH3:48][C:18]1[CH:19]=[CH:20][C:15]([NH:14][CH:11]2[CH2:10][CH2:9][N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:13][CH2:12]2)=[CH:16][C:17]=1[CH:21]=[CH:43][C:44]([O:46][CH3:47])=[O:45] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,667,400 | [Cl-] | [Na+] | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | ord_dataset-9cc455db05a444779921f786a45b21a6 | 2015-01-01T00:12:00 | true | 1-[3-(1-Azido-2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-5-chloro-2-ethoxy-4-fluorophenyl]ethanone (750 mg, 1.8 mmol) (from Step 5) was stirred in tetrahydrofuran (10 mL) with water (0.33 mL) and triphenylphosphine was added. The mixture was heated to 60° C. for 2 hours and cooled to rt. Brine was added and the mixture was extracted with ethyl acetate. The extracts were dried over sodium sulfate, filtered and evaporated to give the desired compound 700 mg, 100%. LCMS calculated for C18H30ClFNO3Si (M+H)+: m/z=390.2; found: 390.2. | CCOc1c(C(C)=O)cc(Cl)c(F)c1C(N)CO[Si](C)(C)C(C)(C)C | null | CCOc1c(C(C)=O)cc(Cl)c(F)c1C(CO[Si](C)(C)C(C)(C)C)N=[N+]=[N-] | null | null | [N:1]([CH:4]([C:14]1[C:15]([O:25][CH2:26][CH3:27])=[C:16]([C:22](=[O:24])[CH3:23])[CH:17]=[C:18]([Cl:21])[C:19]=1[F:20])[CH2:5][O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8])=[N+]=[N-].O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.[Cl-].[Na+].O>[NH2:1][CH:4]([C:14]1[C:15]([O:25][CH2:26][CH3:27])=[C:16]([C:22](=[O:24])[CH3:23])[CH:17]=[C:18]([Cl:21])[C:19]=1[F:20])[CH2:5][O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8] | null | O | C1CCOC1 | null | 60 | null | 99.7 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,639,845 | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | 2015-01-01T00:09:00 | true | A solution of Intermediate 1 (1 g, 3.24 mmol) and 3-amino-4-methylbenzamide (584 mg, 3.89 mmol) in 0.08 M PTSA in 1,4-dioxane was heated to 90° C. for 48 h. TLC showed the completion of starting material (TLC system: 10% methanol/DCM, (Rf): 0.5). The reaction mixture was concentrated, quenched with water, and the precipitated solid was filtered and dried under vacuum. The crude solid was purified by silica gel column chromatography by using 3% methanol/DCM as eluents. The purified solid was further triturated with ether, filtered and dried under vacuum to get the title compound as an off-white solid (430 mg, 31%). 1HNMR (400 MHz, D6-DMSO) δ 2.17 (s, 3H), 5.78-5.81 (dd, 1H J=1.8, 10.1 Hz), 6.28-6.32 (dd, 1H J=1.8, 17 Hz), 6.43-6.50 (dd, 1H J=10.1, 17 Hz), 7.04-7.08 (m, 2H), 7.18-7.24 (m, 2H), 7.27 (br s, 1H), 7.52-7.54 (dd, 1H J=1.7, 7.9 Hz), 7.73-7.76 (m, 1H), 7.87 (br s, 1H), 7.92 (d, 1H), 8.03 (s, 1H), 8.39 (s, 1H), 8.62 (s, 1H), 10.19 (s, 1H). MS m/z: 423.5 (ES+, M+H). | C=CC(=O)Nc1ccccc1Nc1nc(Nc2cc(C(N)=O)ccc2C)ncc1Cl | null | C=CC(=O)Nc1ccccc1Nc1nc(Cl)ncc1Cl | Cc1ccc(C(N)=O)cc1N | null | Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH:15][C:16](=[O:19])[CH:17]=[CH2:18])[C:5]([Cl:20])=[CH:4][N:3]=1.[NH2:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][C:30]=1[CH3:31])[C:25]([NH2:27])=[O:26].CO.C(Cl)Cl>CC1C=CC(S(O)(=O)=O)=CC=1.O1CCOCC1>[C:16]([NH:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[NH:8][C:6]1[C:5]([Cl:20])=[CH:4][N:3]=[C:2]([NH:21][C:22]2[CH:23]=[C:24]([CH:28]=[CH:29][C:30]=2[CH3:31])[C:25]([NH2:27])=[O:26])[N:7]=1)(=[O:19])[CH:17]=[CH2:18] | null | CO | ClCCl | C1COCCO1 | null | 31.4 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
134,307 | [Zn] | null | null | null | ord_dataset-b76b52f4448a4eedb28ffcd8f902046a | 1985-01-01T00:09:00 | true | Methyl 2-[(4R)-3-bromo-4-allyl-2-oxoazetidin-1-yl]-3-methyl-2-butenoate (840 mg) was dissolved in methylene chloride (6 ml) and cooled to 5° C. To this cooled solution were added acetic acid (0.5 ml) and zinc powder (0.60 g), and the mixture was allowed to warm to room temperature. After stirring for 30 minutes, the reaction mixture was diluted with ethyl acetate (6 ml) and filtered through a pad of Celite. The filtrate was further diluted with ethyl acetate (50 ml) and washed successively with water, dilute sodium bicarbonate and brine. Drying over magnesium sulfate and evaporation left an oil, which was chromatographed on silica gel (20 g) eluting with a mixture of benzene and acetone (5:1) to give methyl 2-[(4R)-4-allyl-2-oxoazetidin-1-yl]-3-methyl-2-butenoate (174 mg) as an oil. | C=CC[C@@H]1CC(=O)N1C(C(=O)OC)=C(C)C | null | C=CC[C@@H]1C(Br)C(=O)N1C(C(=O)OC)=C(C)C | null | null | Br[CH:2]1[C@@H:5]([CH2:6][CH:7]=[CH2:8])[N:4]([C:9](=[C:14]([CH3:16])[CH3:15])[C:10]([O:12][CH3:13])=[O:11])[C:3]1=[O:17].C(O)(=O)C>C(Cl)Cl.C(OCC)(=O)C.[Zn]>[CH2:6]([C@H:5]1[N:4]([C:9](=[C:14]([CH3:16])[CH3:15])[C:10]([O:12][CH3:13])=[O:11])[C:3](=[O:17])[CH2:2]1)[CH:7]=[CH2:8] | 0.5 | CCOC(C)=O | ClCCl | CC(=O)O | 5 | 28 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
190,264 | [Li]CCCC | null | null | null | ord_dataset-be83cbc722064f3696975001242f9f1a | 1989-01-01T00:05:00 | true | A solution of 1-methoxymethoxy-naphthalene (3.76 g, 0.020 mole) in dry ether (40 mL) was treated with n-butyllithium (1.6M in hexane; 25.0 mL, 0.040 mole) at room temperature over a period of 15 minutes. After stirring for an additional 1.5 hours, a solution of cyclohexanone (4.90 g, 0.050 mole) in ether (15 mL) was added and the resulting mixture was stirred at room temperature for 2 hours. It was then quenched with saturated aqueous ammonium chloride and the crude product was isolated by extraction with ether. Chromatography with 9:1 hexane/ethyl acetate provided the title compound as a colorless oil (3.30 g, 58%). | COCOc1c(C2(O)CCCCC2)ccc2ccccc12 | null | O=C1CCCCC1 | COCOc1cccc2ccccc12 | null | [CH3:1][O:2][CH2:3][O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1.C([Li])CCC.[C:20]1(=[O:26])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.CCCCCC.C(OCC)(=O)C>CCOCC>[OH:26][C:20]1([C:6]2[CH:7]=[CH:8][C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:5]=2[O:4][CH2:3][O:2][CH3:1])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1 | 1.5 | CCOCC | CCCCCC | CCOC(C)=O | null | null | 57.6 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
686,856 | null | null | null | null | ord_dataset-56747de2718a4ac5bf061651d1cc9e3e | 2005-01-01T00:10:00 | true | To a stirred solution of the 2-methyl-5-(2-pyrrolidine-1-yl-ethylamino)-1H-indole-3-carboxylic acid benzyl ester (147 mg, 0.39 mmol, 1.0 eq) and triethylamine (47.6 mg, 0.47 mmol, 1.2 eq) in acetonitrile in an ice-water bath was added dropwise a solution of acetyl chloride in acetonitrile. After the ice-water bath was removed, the reaction mixture was heated to reflux for overnight. After the mixture was concentrated, the residue was purified by preparative HPLC (reverse-phase, 10-100 CH3CN:H2O, 0.1% TFA) to yield the desire indole amine in 33.0% yield. Elemental Analysis: C25H29N3O3.2HCl.0.3H2O Calcd: C: 60.31; H: 6.40; N: 8.44. Found: C: 60.63; H: 6.40; N: 8.04. ESI-MS: m/z 420.78 (M+H)+. | Nc1cc2ccccc2[nH]1 | null | Cc1[nH]c2ccc(NCCN3CCCC3)cc2c1C(=O)OCc1ccccc1 | CCN(CC)CC | null | C(OC([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17](NCCN3CCCC3)[CH:18]=2)[NH:13][C:12]=1C)=O)C1C=CC=CC=1.C([N:31](CC)CC)C.C(Cl)(=O)C>C(#N)C>[NH:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]=[C:12]1[NH2:31] | null | CC(=O)Cl | CC#N | null | null | null | 33 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
671,962 | CCN=C=NCCCN(C)C | Cl | On1nnc2ccccc21 | null | ord_dataset-e90cd41afe844e49875435eb99903799 | 2005-01-01T00:05:00 | true | A solution (2R)-2-(4,4-dimethyl-2-oxopentyl)-4-pentenoic acid (Preparation 112) (15.91 g, 74.3 mmol), 1-hydroxybenzotriazole hydrate (11.00 g, 81.4 mmol), L-serine ethylester hydrochloride (13.84 g, 81.6 mmol) and N,N-diisopropylethylamine (27 ml, 156.0 mmol) in dichloromethane (280 ml) was treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (15.67 g, 81.7 mmol) and stirred at room temperature for 18 hours under a nitrogen atmosphere. The reaction mixture was diluted with dichloromethane and washed with water, aqueous citric acid (2M), saturated sodium hydrogen carbonate solution and brine, dried over anhydrous sodium sulphate and filtered. The solvent was removed under reduced pressure to afford the title compound as a yellow oil (23.8 g). | C=CC[C@H](CC(=O)CC(C)(C)C)C(=O)N[C@@H](CO)C(=O)OCC | null | C=CC[C@H](CC(=O)CC(C)(C)C)C(=O)O | CCOC(=O)[C@@H](N)CO | null | [CH3:1][C:2]([CH3:15])([CH3:14])[CH2:3][C:4](=[O:13])[CH2:5][C@@H:6]([CH2:10][CH:11]=[CH2:12])[C:7]([OH:9])=O.O.ON1C2C=CC=CC=2N=N1.Cl.[CH2:28]([O:30][C:31](=[O:36])[C@H:32]([CH2:34][OH:35])[NH2:33])[CH3:29].C(N(CC)C(C)C)(C)C.Cl.CN(C)CCCN=C=NCC>ClCCl>[CH3:14][C:2]([CH3:1])([CH3:15])[CH2:3][C:4](=[O:13])[CH2:5][C@@H:6]([CH2:10][CH:11]=[CH2:12])[C:7]([NH:33][C@@H:32]([CH2:34][OH:35])[C:31]([O:30][CH2:28][CH3:29])=[O:36])=[O:9] | 18 | CCN(C(C)C)C(C)C | O | ClCCl | 25 | 97.8 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,532,078 | null | null | null | null | ord_dataset-8d5c200bca27407ab9febe7598e16458 | 2015-01-01T00:01:00 | true | The title compound was prepared according to Method 4 using (4S,5R)-3-(tert-butoxycarbonyl)-5-isopropyl-2,2-dimethyl-1,3-oxazolidine-4-carboxylic acid (Preparation 60) and 4-(1-methylethyl)-1,2-benzenediamine. | CC(C)c1ccc2[nH]c([C@@H](N)[C@H](O)C(C)C)nc2c1 | null | CC(C)[C@H]1OC(C)(C)N(C(=O)OC(C)(C)C)[C@@H]1C(=O)O | CC(C)c1ccc(N)c(N)c1 | null | C(OC([N:8]1[C@H:12]([C:13](O)=O)[C@@H:11]([CH:16]([CH3:18])[CH3:17])[O:10]C1(C)C)=O)(C)(C)C.[CH3:21][CH:22]([C:24]1[CH:25]=[C:26]([NH2:31])[C:27]([NH2:30])=[CH:28][CH:29]=1)[CH3:23]>>[NH2:8][C@H:12]([C:13]1[NH:30][C:27]2[CH:28]=[CH:29][C:24]([CH:22]([CH3:21])[CH3:23])=[CH:25][C:26]=2[N:31]=1)[C@H:11]([OH:10])[CH:16]([CH3:18])[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 |
1,701,529 | O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F | null | null | null | ord_dataset-54347fcace774f89850681d6dec8009f | 2016-01-01T00:03:00 | true | A solution of 47.9 g (161 mmol) of (2S,5S)-tert-butyl 5-hydroxy-1-(2,2,2-trifluoroacetyl)piperidine-2-carboxylate in dehydrated acetonitrile (318 mL) was cooled from −30 to −40° C. under argon atmosphere, and 20.5 mL (177 mmol) of 2,6-lutidine was added, and then 28.4 mL (169 mmol) of trifluoromethanesulfonic acid anhydride was added dropwise over 40 minutes, followed by further allowing to react at −30° C. for 15 minutes. To this reaction mixture was added 39.7 g (322 mmol) of benzyloxyamine (washed with acetonitrile (11 mL)) within 8 minutes, followed by raising the temperature to 0° C. within 30 minutes, and further 20.5 mL (177 mmol) of 2,6-lutidine was added, followed by allowing to react at 0 to 5° C. for 2 days. This reaction mixture was concentrated under reduced pressure, and the resulting residue was diluted with ethyl acetate (960 mL) and washed sequentially with water (960 mL), 10% aqueous citric acid solution (960 mL×3 times), 6.5% aqueous sodium hydrogencarbonate solution (480 mL) and saturated brine (480 mL). Each aqueous layer was back-extracted with ethyl acetate (960 mL), the organic layers were combined, and the solvent was distilled off under reduced pressure. The resulting residue was dissolved in 1,4-dioxane (320 mL) solution and water (86 mL), and, under ice cooling, 2.5M NaOH (128 mL) was added dropwise, followed by allowing to react at the same temperature for 0.5 hours. Acetic acid (ca. 9.3 mL) was added to the reaction mixture, followed by concentration under reduced pressure, and subsequently the resulting concentrated residue was extracted with ethyl acetate (580 mL, 290 mL). After the organic layers were washed respectively with 50% aqueous potassium carbonate solution (580 mL), they were combined, and the solvent was distilled off under reduced pressure. The resulting residue was applied to silica gel column chromatography (hexane/ethyl acetate=4/1→0/1→ethyl acetate/methanol=100/1→19/1) to afford 36.58 g of the title compound as a colorless oil (yield 74%). Instrumental data were consistent with those of Example 4. | CC(C)(C)OC(=O)[C@@H]1CC[C@@H](NOCc2ccccc2)CN1 | null | NOCc1ccccc1 | CC(C)(C)OC(=O)[C@@H]1CC[C@H](O)CN1C(=O)C(F)(F)F | null | O[C@@H:2]1[CH2:7][N:6](C(=O)C(F)(F)F)[C@H:5]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:4][CH2:3]1.N1C(C)=CC=CC=1C.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[CH2:44]([O:51][NH2:52])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>C(#N)C.C(O)(=O)C>[CH2:44]([O:51][NH:52][C@H:2]1[CH2:7][NH:6][C@H:5]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[CH2:4][CH2:3]1)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1 | null | Cc1cccc(C)n1 | CC#N | CC(=O)O | 0 | 74.2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
896,996 | null | null | null | null | ord_dataset-de6bce51790e4004a27e1a8f2bcc7ded | 2009-01-01T00:08:00 | true | Similar procedure as described in example 384 was used, starting from 1-Isopropoxy-3-(5-methyl-1H-pyrazol-3-ylamino)-isoquinoline-6-carboxylic acid and Methyl-(2-piperidin-1-yl-ethyl)-amine to give 1-Isopropoxy-3-(5-methyl-1H-pyrazol-3-ylamino)-isoquinoline-6-carboxylic acid methyl-(2-piperidin-1-yl-ethyl)-amide. LC-MS: m/e 451 (MH+). | Cc1cc(Nc2cc3cc(C(=O)N(C)CCN4CCCCC4)ccc3c(OC(C)C)n2)n[nH]1 | null | CNCCN1CCCCC1 | Cc1cc(Nc2cc3cc(C(=O)O)ccc3c(OC(C)C)n2)n[nH]1 | null | [CH:1]([O:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([C:15]([OH:17])=O)=[CH:12][CH:13]=2)[CH:8]=[C:7]([NH:18][C:19]2[CH:23]=[C:22]([CH3:24])[NH:21][N:20]=2)[N:6]=1)([CH3:3])[CH3:2].[CH3:25][NH:26][CH2:27][CH2:28][N:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1>>[CH3:25][N:26]([CH2:27][CH2:28][N:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)[C:15]([C:11]1[CH:10]=[C:9]2[C:14](=[CH:13][CH:12]=1)[C:5]([O:4][CH:1]([CH3:2])[CH3:3])=[N:6][C:7]([NH:18][C:19]1[CH:23]=[C:22]([CH3:24])[NH:21][N:20]=1)=[CH:8]2)=[O: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 |
120,637 | Cl | null | null | null | ord_dataset-1d493fcbd5494078b46e816998dcb991 | 1984-01-01T00:08:00 | true | In 100 ml of ethanol was dissolved 10.0 g. (0.05 mole) of sodium 2,4-dichloro-3-methylphenolate. With stirring at room temperature, 9.1 g (0.05 mole) of ethyl 2-bromopropionate was added. The mixture was heated under relfux for 4 hours. The ethanol was distilled off under reduced pressure, and the residue was extracted with 50 ml of diethyl ether. The ethereal layer was washed with 25 ml of a 5% aqueous solution of sodium hydroxide and 25 ml of water, and dried over anyhdrous magnesium sulfate. The dessicant was removed by filtration, and the diethyl ether was distilled off to give 11.8 g of crude ethyl 2-(2,4-dichloro-3-methylphenoxy)propionate. The crude ester (11.8 g) was dissolved in 100 ml of glacial acetic acid. Concentrated hydrochloric acid (25 ml) was added, and the mixture was stirred at 100° C. for 40 minutes. The reaction mixture was cooled, and poured onto 300 ml of ice water. The precipitated crystals were filtered, washed with water, and dried to give 9.2 g of 2-(2,4-dichloro-3-methylphenoxy)-propionic acid. The yield was 73.9% based on the sodium 2,4-dichloro-3-methylphenolate, and the final product had a melting point of 149.5 to 150.5° C. | Cc1c(Cl)ccc(OC(C)C(=O)O)c1Cl | null | CCOC(=O)C(C)Oc1ccc(Cl)c(C)c1Cl | null | null | [Cl:1][C:2]1[C:15]([CH3:16])=[C:14]([Cl:17])[CH:13]=[CH:12][C:3]=1[O:4][CH:5]([CH3:11])[C:6]([O:8]CC)=[O:7].Cl>C(O)(=O)C>[Cl:1][C:2]1[C:15]([CH3:16])=[C:14]([Cl:17])[CH:13]=[CH:12][C:3]=1[O:4][CH:5]([CH3:11])[C:6]([OH:8])=[O:7] | 0.67 | CC(=O)O | null | null | 100 | 86.7 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
214,827 | null | null | null | null | ord_dataset-5ebf3d05077a4f7fb91a1cd9bdc504d2 | 1990-01-01T00:09:00 | true | 7-Methylsulfonylamino-3-methylthio-6-phenoxy-4H-1-benzopyran-4-one was reacted with m-chloroperbenzoic acid in equimolar amounts to obtain 3-methylsulfinyl-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one [Compound No. 5]. | CS(=O)c1coc2cc(NS(C)(=O)=O)c(Oc3ccccc3)cc2c1=O | null | CSc1coc2cc(NS(C)(=O)=O)c(Oc3ccccc3)cc2c1=O | O=C(OO)c1cccc(Cl)c1 | null | [CH3:1][S:2]([NH:5][C:6]1[C:18]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:17][C:9]2[C:10](=[O:16])[C:11]([S:14][CH3:15])=[CH:12][O:13][C:8]=2[CH:7]=1)(=[O:4])=[O:3].ClC1C=CC=C(C(OO)=[O:34])C=1>>[CH3:15][S:14]([C:11]1[C:10](=[O:16])[C:9]2[CH:17]=[C:18]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:6]([NH:5][S:2]([CH3:1])(=[O:3])=[O:4])=[CH:7][C:8]=2[O:13][CH:12]=1)=[O:34] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
472,177 | [Fe] | null | null | null | ord_dataset-cd531114850e4f239b2a3661044ae672 | 2000-01-01T00:08:00 | true | The product of Example 11 (778 mg), methanol (40.5 mL), acetic acid (13.5 mL) and iron powder (382 mg) were heated at reflux and stirred mechanically for 6 h. More iron powder (1.15 g) was added and the reaction was heated at reflux 2 more hours, after which it was cooled, filtered through celite, and concentrated to a thick black oil. Added ethyl acetate (200 mL) and water (100 mL), stirred, and filtered through celite. The layers were separated and the ethyl acetate dried over MgSO4 and concentrated to a thick yellow oil (754 mg). The oil was chromatographed on silica gel using ethyl acetate/hexane (1:9) as eluent. The title compound was obtained as an off-white solid (526 mg). CI-HRMS calc'd. for C22H26N4Br (M+H)+ : 425.134083. Found: 425.131850. | CCN(c1nc(C)cc(-c2ccccc2N)n1)c1ccc(C(C)C)cc1Br | null | CCN(c1nc(C)cc(-c2ccccc2[N+](=O)[O-])n1)c1ccc(C(C)C)cc1Br | null | null | [Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[N:11]([CH2:28][CH3:29])[C:12]1[N:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N+:24]([O-])=O)[CH:15]=[C:14]([CH3:27])[N:13]=1.CO>[Fe].C(O)(=O)C>[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[N:11]([CH2:28][CH3:29])[C:12]1[N:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[NH2:24])[CH:15]=[C:14]([CH3:27])[N:13]=1 | 6 | CC(=O)O | CO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
491,712 | [K+] | null | null | null | ord_dataset-37b0416f244344a08cf357e851eedf2a | 2001-01-01T00:01:00 | true | Potassium thioacetate (0.22 g) is added to a solution of 1.07 g of (3R,5S)-1-allyloxycarbonyl-3-methane sulfonyloxy-5-[2-(imidazo[5,1-b]thiazol-2-yl)vinyl]pyrrolidine (a mixture of geometrical isomers) in 5 ml of DMF, and the mixture is stirred at 70° C. for 4 hr. Ethyl acetate is added to the reaction mixture, and the mixture is successively washed with water and a saturated aqueous sodium hydrogencarbonate solution, and saturated saline and dried over magnesium sulfate. The solvent is removed by evaporation. The residue is purified by column chromatography on silica gel to give 0.42 g of the title compound. | C=CCOC(=O)N1C[C@@H](SC(C)=O)C[C@H]1C=Cc1cn2cncc2s1 | null | CC([O-])=S | C=CCOC(=O)N1C[C@H](OS(C)(=O)=O)C[C@H]1C=Cc1cn2cncc2s1 | null | [C:1]([O-:4])(=[S:3])[CH3:2].[K+].[CH2:6]([O:9][C:10]([N:12]1[C@H:16]([CH:17]=[CH:18][C:19]2[S:23][C:22]3=[CH:24][N:25]=[CH:26][N:21]3[CH:20]=2)[CH2:15][C@@H:14](OS(C)(=O)=O)[CH2:13]1)=[O:11])[CH:7]=[CH2:8].C(OCC)(=O)C>CN(C=O)C>[C:1]([S:3][C@H:14]1[CH2:15][C@@H:16]([CH:17]=[CH:18][C:19]2[S:23][C:22]3=[CH:24][N:25]=[CH:26][N:21]3[CH:20]=2)[N:12]([C:10]([O:9][CH2:6][CH:7]=[CH2:8])=[O:11])[CH2:13]1)(=[O:4])[CH3:2] | 4 | CN(C)C=O | CCOC(C)=O | null | 70 | null | 57.8 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
938,457 | null | null | null | null | ord_dataset-90b0aa1f83334a02919b2be3a1c04542 | 2010-01-01T00:02:00 | true | Prepared by the method of Example 31 using 2,6-bis(hydroxymethyl)pyridine (0.11 g) and 2,3-dichloro-N-(3,5-dichloro-2-pyrazinyl)benzenesulphonamide (Example 74) (0.11 g) in N-methylpyrrolidinone (2 mL). Yield 0.043 g. | O=S(=O)(Nc1ncc(Cl)nc1OCc1cccc(CO)n1)c1cccc(Cl)c1Cl | null | O=S(=O)(Nc1ncc(Cl)nc1Cl)c1cccc(Cl)c1Cl | OCc1cccc(CO)n1 | null | [OH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][OH:10])[N:4]=1.[Cl:11][C:12]1[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=1[S:19]([NH:22][C:23]1[C:28](Cl)=[N:27][C:26]([Cl:30])=[CH:25][N:24]=1)(=[O:21])=[O:20]>CN1CCCC1=O>[Cl:11][C:12]1[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=1[S:19]([NH:22][C:23]1[C:28]([O:1][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][OH:10])[N:4]=2)=[N:27][C:26]([Cl:30])=[CH:25][N:24]=1)(=[O:21])=[O:20] | null | CN1CCCC1=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,264,989 | [Na+] | [OH-] | null | null | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | 2013-01-01T00:03:00 | true | To a solution of ethyl (4-{[3-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-thiadiazol-3-yl)-2-ethylphenyl]methyl}-1-piperidinyl)acetate (D145) (80 mg, 0.148 mmol) in Isopropanol (6 mL) and Water (6.00 mL) was added NaOH (1.476 mL, 0.738 mmol). The reaction solution was heated to 90° C. for 2 hours. The solvent was removed in vacuo and the residue was acidified to pH=3-4, extracted with ethyl acetate. The combined organic phases were dried, concentrated and purified by Mass Directed AutoPrep to afford (4-{[3-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-thiadiazol-3-yl)-2-ethylphenyl]methyl}-1-piperidinyl)acetic acid (E105) (59 mg) as a TFA salt. δH (DMSO-d6, 400 MHz): 1.01 (3H, t), 1.28 (6H, d), 1.55 (2H, m), 1.72 (3H, m), 2.62 (2H, d), 2.87 (4H, m), 3.38 (2H, m), 3.98 (2H, s), 4.79 (1H, m), 7.23 (2H, m), 7.32 (1H, d), 7.59 (1H, dd), 7.95 (1H, dd), 8.07 (1H, d). δF (DMSO-d6, 376 MHz): −73.5. MS (ES): C27H32ClN3O3S requires 513.2. found 514.2 (M+H+). | CCc1c(CC2CCN(CC(=O)O)CC2)cccc1-c1nsc(-c2ccc(OC(C)C)c(Cl)c2)n1 | null | CCOC(=O)CN1CCC(Cc2cccc(-c3nsc(-c4ccc(OC(C)C)c(Cl)c4)n3)c2CC)CC1 | null | null | [Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[S:16][N:15]=[C:14]([C:17]3[C:18]([CH2:36][CH3:37])=[C:19]([CH2:23][CH:24]4[CH2:29][CH2:28][N:27]([CH2:30][C:31]([O:33]CC)=[O:32])[CH2:26][CH2:25]4)[CH:20]=[CH:21][CH:22]=3)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[OH-].[Na+]>C(O)(C)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[S:16][N:15]=[C:14]([C:17]3[C:18]([CH2:36][CH3:37])=[C:19]([CH2:23][CH:24]4[CH2:25][CH2:26][N:27]([CH2:30][C:31]([OH:33])=[O:32])[CH2:28][CH2:29]4)[CH:20]=[CH:21][CH:22]=3)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10] | null | O | CC(C)O | null | 90 | 77.5 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,519,951 | [H-] | [Na+] | null | null | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | 2014-01-01T00:12:00 | true | 1-Cyclobutyl-piperidin-4-ol (0.04 grams, 0.26 mmol) in tetrahydrofuran (3 mL) was treated with cooled and stirred suspension of sodium hydride (0.021 grams, 0.51 mmol) in tetrahydrofuran (8 mL) slowly over the period of 5 minutes and the reaction mixture was stirred for 2 hours at room temperature. A solution of (2-Bromo-4,5,7,8-tetrahydro-thiazolo[5,4-d]azepin-6-yl)-cyclopropyl-methanone (0.053 grams, 0.17 mmol, obtained in above step) in tetrahydrofuran (3 mL) was added drop wise over a period of 5 minutes and refluxed for 15 hours. Reaction mass was quenched onto ice cold water and the product was extracted with ethyl acetate (3×10 mL). The combined organics were washed with water followed by brine and dried over anhydrous sodium sulphate. Organic volatiles were evaporated under vacuum. The residue obtained was purified by flash chromatography (methanol/chloroform 3/97) to obtain the title compound (0.05 grams). | O=C(C1CC1)N1CCc2nc(OC3(C4CCC4)CCNCC3)sc2CC1 | null | OC1CCN(C2CCC2)CC1 | O=C(C1CC1)N1CCc2nc(Br)sc2CC1 | C1CCOC1 | C1([N:5]2[CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]2)CCC1.[H-].[Na+].Br[C:15]1[S:16][C:17]2[CH2:18][CH2:19][N:20]([C:25]([CH:27]3[CH2:29][CH2:28]3)=[O:26])[CH2:21][CH2:22][C:23]=2[N:24]=1.O1[CH2:34][CH2:33][CH2:32][CH2:31]1>>[CH:31]1([C:8]2([O:11][C:15]3[S:16][C:17]4[CH2:18][CH2:19][N:20]([C:25]([CH:27]5[CH2:29][CH2:28]5)=[O:26])[CH2:21][CH2:22][C:23]=4[N:24]=3)[CH2:7][CH2:6][NH:5][CH2:10][CH2:9]2)[CH2:34][CH2:33][CH2:32]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 |
708,780 | NN | null | null | null | ord_dataset-c8069773c1a148aca8ab417108daacc5 | 2006-01-01T00:05:00 | true | To a solution of 4-iodo-3-nitroanisole (5 g, 17.9 mmole) in 100 ml methanol was added FeCl3 (50 mg, 0.3 mmole) and activated carbon (40 mg). The mixture was heated to reflux and hydrazine hydrate (1.75 g, 35 mmole) was added dropwise. The mixture was refluxed for an additional 8 hours and cooled to room temperature, filtered through Celite. The filtrate was concentrated and purified by column chromatography (eluting with 10% EtOAc in hexanes) to give 4.05 g product as pale yellow oil (91% yield). 1H NMR (300 MHz, CDCl3) δ 7.47 (1H, d, J=8.7 Hz), 6.31 (1H, d, J=2.8 Hz), 6.13 (1H, dd, J=2.8, 8.7 Hz), 3.73 (3H, s). | COc1ccc(I)c(N)c1 | null | COc1ccc(I)c([N+](=O)[O-])c1 | null | null | [I:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[N+:10]([O-])=O.O.NN>CO>[I:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[NH2:10] | null | O | CO | null | 25 | null | 90.8 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
398,577 | [Pd+2] | CC(=O)[O-] | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | ord_dataset-a4a191e812a64d0598ea918f047e8da7 | 1998-01-01T00:04:00 | true | A solution of allyl acetate (13.5 ml, 125 mmol) in THF (8 ml), was evacuated and purged with argon (3 times). Palladium acetate (122 mg, 0.50mmol) and triphenylphosphine (525 mg, 2.0 mmol) were added as solutions in tetrahydrofuran (1.5 ml each), followed by 3-nitro-6-trifluoromethyl-2-pyridinone (2.6 g, 12.5 mmol) in THF (2 ml). The reaction was heated to reflux for 64 h, and more allyl acetate (13.5 ml, 125 mmol), triphenylphosphine (525 mg, 2.0 mmol), palladium acetate (122 mg, 0.5 mmol), and tetrahydrofuran (13 ml) were added. After a further 24 h and 48 h at reflux addditional allyl acetate (13.5 ml, 125 mmol), palladium acetate (122 mg, 0.5 mmol), and triphenylphosphine (525 mg, 2.0 mmol) were added and the reaction was heated to reflux for a further 24 h. The reaction was cooled and evaported in vacuo to a gum which was purified by flash column chromatography on silica (15% ethyl acetate/hexane) to give the product contaminated with unreacted 3-nitro-6-trifluoromethyl-2-pyridinone. This material was diluted with ethyl acetate and washed with water adjusted to pH 12 with sodium carbonate, dried (Na2SO4), and evaporated in vacuo to give the title compound (1.05 g): 1H NMR (CDCl3) selected signals at δ4.80 (d, J=5.8 Hz, 2H), 5.28-5.33 (m, 2H), 5.86-5.96 (m, 1H), 6.80 (d, J=7.9 Hz, 1H), 8.22 (d, J=7.9 Hz, 1H). | C=CCn1c(C(F)(F)F)ccc([N+](=O)[O-])c1=O | null | O=c1[nH]c(C(F)(F)F)ccc1[N+](=O)[O-] | C=CCOC(C)=O | null | C(O[CH2:5][CH:6]=[CH2:7])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N+:27]([C:30]1[C:31](=[O:40])[NH:32][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:34][CH:35]=1)([O-:29])=[O:28]>C1COCC1.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N+:27]([C:30]1[C:31](=[O:40])[N:32]([CH2:7][CH:6]=[CH2:5])[C:33]([C:36]([F:39])([F:37])[F:38])=[CH:34][CH:35]=1)([O-:29])=[O:28] | 24 | C1CCOC1 | CCOC(C)=O | null | null | 33.8 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,512,380 | Cl | null | null | null | ord_dataset-1a1aa5d1c3224edca0aec6e3398da985 | 2014-01-01T00:11:00 | true | To a solution of (S)-methyl 5-(tert-butyldimethylsilyloxy)-4-(3-(2,3-difluorobenzyl)-1-methylureido)pentanoate (9.7 g, 21.6 mmol) in MeOH (40 mL) was added HCl (4 N in dioxane, 5.4.0 mL, 21.6 mmol). The resulting solution was stirred at RT for 1 h. The mixture was concentrated and re-dissolved in EtOAc. The organic mixture was washed with saturated NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give (S)-methyl 4-(3-(2,3-difluorobenzyl)-1-methylureido)pentanoate (6.84 g, crude) as a white solid, which was used without further purification. LRMS (M+H+) m/z 331.2. | COC(=O)CC[C@H](C)N(C)C(=O)NCc1cccc(F)c1F | null | COC(=O)CC[C@@H](CO[Si](C)(C)C(C)(C)C)N(C)C(=O)NCc1cccc(F)c1F | null | null | [Si](O[CH2:9][C@@H:10]([N:17]([CH3:30])[C:18]([NH:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:23]=1[F:29])=[O:19])[CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])(C(C)(C)C)(C)C.Cl>CO>[F:29][C:23]1[C:24]([F:28])=[CH:25][CH:26]=[CH:27][C:22]=1[CH2:21][NH:20][C:18](=[O:19])[N:17]([C@@H:10]([CH3:9])[CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH3:30] | 1 | CO | null | null | 25 | null | 100.7 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
221,327 | null | null | null | null | ord_dataset-42629b4cf1094978a5e5f29f22639ee7 | 1991-01-01T00:01:00 | true | Methyl [1-(3-propylphenyl)hydrazino]acetate (700 mg) was dissolved in acetonitrile (10 ml) under nitrogen at room temperature. Methyl isocyanate (0.69 ml) was added to the solution which was then heated at 80° for 85 min. The solvent was removed in vacuo and the residue was dissolved in ether (10 ml). Hexane (20 ml) was added to precipitate a solid which was filtered off to give the title compound (677 mg), m.p. 76°-77°. | CCCc1cccc(N(CC(=O)OC)NC(=O)NC)c1 | null | CCCc1cccc(N(N)CC(=O)OC)c1 | CN=C=O | null | [CH2:1]([C:4]1[CH:5]=[C:6]([N:10]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[NH2:11])[CH:7]=[CH:8][CH:9]=1)[CH2:2][CH3:3].[CH3:17][N:18]=[C:19]=[O:20]>C(#N)C>[CH3:17][NH:18][C:19]([NH:11][N:10]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([CH2:1][CH2:2][CH3:3])[CH:5]=1)=[O:20] | null | CC#N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
588,128 | Cl | null | null | null | ord_dataset-7a74d48eeefd45aba53e7258f3ae067a | 2003-01-01T00:04:00 | true | The 4,6-dichloro-pyrido[3,4-d]pyrimidine obtained from the previous reaction was taken up in dioxane (50 ml), the 3-methyl 4-phenoxy aniline hydrochloride (2.8 g, 12 mmol) was added and the contents heated to an external bath temperature of −80° C. for 3 hours, whereupon yellow precipitation occurred. Further dioxane (20 ml) was added and the contents heated at −75° C. for 12 hours. The solution was then filtered and the yellow solid placed under vacuum to provide the desired (6-chloro-pyrido[3,4-d]pyrimidin-4-yl)-(3-methyl-4-phenoxy-phenyl)-amine hydrochloride (3.6 g, ˜100%). 1H NMR (CD3OD; 400 MHz) δ 9.05 (s, 1H), 8.87 (s, 1H), 8.64 (s, 1H), 7.69 (d, J=2.5 Hz, 1H), 7.58 (dd, J=8.7, 2.5 Hz, 1H),7.35 (dd, J=8.7, 7.5 Hz, 2H), 7.10 (t, J=7.2 Hz, 1H), 6.94 (d, J=8.7 Hz, 3H), 2.29 (s, 3H). MS m/z (MH+): 363.2 | Cc1cc(Nc2ncnc3cnc(Cl)cc23)ccc1Oc1ccccc1 | null | Cc1cc(N)ccc1Oc1ccccc1 | Clc1cc2c(Cl)ncnc2cn1 | null | [Cl:1][C:2]1[C:3]2[CH:11]=[C:10]([Cl:12])[N:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.Cl.[CH3:14][C:15]1[CH:16]=[C:17]([CH:19]=[CH:20][C:21]=1[O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[NH2:18]>O1CCOCC1>[ClH:1].[Cl:12][C:10]1[N:9]=[CH:8][C:4]2[N:5]=[CH:6][N:7]=[C:2]([NH:18][C:17]3[CH:19]=[CH:20][C:21]([O:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[C:15]([CH3:14])[CH:16]=3)[C:3]=2[CH:11]=1 | null | C1COCCO1 | null | null | -80 | 100 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,475,346 | null | null | null | null | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | 2014-01-01T00:09:00 | true | The title compound was prepared in analogy to the synthesis of compound of Example 2, using tert-butyl 4-(4-(4,4,5-trimethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate and with an additional deprotection step before final reduction (tR 1.0 min (conditions 1), MH+=410). | c1cnc2ccc(Cc3cnc4ccc(-c5cnn(C6CCNCC6)c5)nn34)cc2c1 | null | CC1OB(c2cnn(C3CCN(C(=O)OC(C)(C)C)CC3)c2)OC1(C)C | Cn1cc(-c2ccc3ncc(Cc4ccc5ncccc5c4)n3n2)cn1 | null | [CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:13]([CH2:16][C:17]4[CH:18]=[C:19]5[C:24](=[CH:25][CH:26]=4)[N:23]=[CH:22][CH:21]=[CH:20]5)=[CH:14][N:15]=3)[N:12]=2)[CH:4]=[N:3]1.CC1(C)C(C)OB([C:34]2C=N[N:37]([CH:39]3CCN(C(OC(C)(C)C)=O)C[CH2:40]3)[CH:38]=2)O1>>[NH:37]1[CH2:39][CH2:40][CH:1]([N:2]2[CH:6]=[C:5]([C:7]3[CH:8]=[CH:9][C:10]4[N:11]([C:13]([CH2:16][C:17]5[CH:18]=[C:19]6[C:24](=[CH:25][CH:26]=5)[N:23]=[CH:22][CH:21]=[CH:20]6)=[CH:14][N:15]=4)[N:12]=3)[CH:4]=[N:3]2)[CH2:34][CH2:38]1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,527,569 | [Al+3] | [Cl-] | null | null | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | 2014-01-01T00:12:00 | true | To a solution of 5-bromo-2-chloro-4-methoxybenzoic acid (4, 15 g, 56.5 mmol) in toluene (72 mL) was added thionyl chloride (8.24 mL, 113 mmol) and N,N-dimethylformamide (0.1 mL). The solution was refluxed at 90° C. for 4 h, cooled to room temperature and evaporated to remove toluene and residual reagent. The obtained acyl chloride was diluted with dichloromethane (240 mL) and added portionwise aluminum chloride (8.3 g, 62.2 mmol) and phenetole (7.2 mL, 56.5 mmol) at 0° C. The reaction mixture was stirred at room temperature overnight, quenched with 1N HCl (15 mL) and H2O (15 mL). The organic layer was extracted with dichloromethane two times, washed with 1N HCl and brine, dried over magnesium sulfate, filtered and concentrated in vacuo to yield the title compound as a yellowish solid which was used without further purification. | CCOc1ccc(C(=O)c2cc(Br)c(OC)cc2Cl)cc1 | null | COc1cc(Cl)c(C(=O)O)cc1Br | CCOc1ccccc1 | null | [Br:1][C:2]1[C:3]([O:12][CH3:13])=[CH:4][C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.S(Cl)(Cl)=O.[Cl-].[Al+3].[Cl-].[Cl-].[C:22]1([O:28][CH2:29][CH3:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1(C)C=CC=CC=1.CN(C)C=O>[Br:1][C:2]1[C:3]([O:12][CH3:13])=[CH:4][C:5]([Cl:11])=[C:6]([C:7]([C:25]2[CH:26]=[CH:27][C:22]([O:28][CH2:29][CH3:30])=[CH:23][CH:24]=2)=[O:9])[CH:10]=1 | 8 | Cc1ccccc1 | CN(C)C=O | O=S(Cl)Cl | 90 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,495,010 | [Pd+2] | [OH-] | null | null | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | 2014-01-01T00:10:00 | true | A suspension of ethyl {4-[2-tert-butyl-4-(1-methylethenyl)phenyl]piperazin-1-yl}(oxo)acetate (Example 166, 0.17 g, 0.474 mmol) and palladium hydroxide (20% on carbon, wetted with ca. 50% water, 20 mg) in ethyl acetate (3 mL) was stirred under hydrogen at room temperature for 30 minutes. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure to provide ethyl {4-[2-tert-butyl-4-(1-methylethyl)phenyl]piperazin-1-yl}(oxo)acetate (0.133 g, 78%) as a colorless oil. | CCOC(=O)C(=O)N1CCN(c2ccc(C(C)C)cc2C(C)(C)C)CC1 | null | C=C(C)c1ccc(N2CCN(C(=O)C(=O)OCC)CC2)c(C(C)(C)C)c1 | null | null | [C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:13])=[CH2:12])[CH:8]=[CH:7][C:6]=1[N:14]1[CH2:19][CH2:18][N:17]([C:20](=[O:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:16][CH2:15]1)([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C.[OH-].[Pd+2].[OH-]>[C:1]([C:5]1[CH:10]=[C:9]([CH:11]([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[N:14]1[CH2:19][CH2:18][N:17]([C:20](=[O:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:16][CH2:15]1)([CH3:3])([CH3:4])[CH3:2] | 0.5 | CCOC(C)=O | null | null | 25 | 77.8 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
426,946 | CCC(=O)CC(=O)[O-] | [Al+3] | null | null | ord_dataset-1ecf96d88f254270bff816ee7eeffef6 | 1999-01-01T00:02:00 | true | A mixture of 5.3 g of the aluminum tri(methyl acetylacetate) catalyst mentioned in Example 1 and 85 g of 1,2-propylene carbonate was heated to 170° C. and, at this temperature a mixture of 55 g (0.47 mol) of methyl acetoacetate and 43.7 g (0.52 mol) of 2-methyl-3-butyn-2-ol was metered in at a constant rate over the course of 4 h. After the addition was complete, the mixture was stirred at 170° C. for 30 min. During this time, CO2 was evolved and low boilers distilled out. The reaction mixture was subsequently cooled, and the 2-methyl-2,4-heptadien-6-one which was formed was distilled out under about 100 mbar. This resulted in 42 g of pure 2-methyl-2,4-heptadien-6-one, which corresponds to a yield of 72% of theory based on reacted 2-methyl-3-butyn-2-ol. | CC(=O)C=CC=C(C)C | null | O=C=O | COC(=O)CC(C)=O | C#CC(C)(C)O | [C:1]([O:7]C)(=O)[CH2:2][C:3]([CH3:5])=O.[CH3:9][C:10](O)(C#C)[CH3:11].[C:15](=O)=O>CCC(CC([O-])=O)=O.CCC(CC([O-])=O)=O.CCC(CC([O-])=O)=O.[Al+3].C1(=O)OC(C)CO1>[CH3:9][C:10](=[CH:5][CH:3]=[CH:2][C:1](=[O:7])[CH3:15])[CH3:11] | 0.5 | CC1COC(=O)O1 | null | null | 170 | 72 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
133,148 | null | null | null | null | ord_dataset-34cf5f1378de4e34844aea93a2f9a9d3 | 1985-01-01T00:08:00 | true | 42 ml of triethylamine, 25 ml of isopropylamine, 250 ml of methylethylketone and 32 g of 2,4,6-trichloro-5-methoxypyrimidine (prepared as indicated by Budesinsky et Coll., Ceskoslov. Farm. 10, 241-247, 1961) were stirred together at 20° C. for 6 hours. The reaction mixture was then evaporated under reduced pressure and the residue fixed on a silica gel column. This was followed by elution with a 95/5 toluene-diethylamine mixture. In this way were isolated 20.2 g of 4-isopropylamino-2,6-dichloro-5-methoxypyrimidine. | COc1c(Cl)nc(Cl)nc1NC(C)C | null | COc1c(Cl)nc(Cl)nc1Cl | CC(C)N | null | C(N(CC)CC)C.[CH:8]([NH2:11])([CH3:10])[CH3:9].[Cl:12][C:13]1[N:18]=[C:17](Cl)[C:16]([O:20][CH3:21])=[C:15]([Cl:22])[N:14]=1>CC(CC)=O>[CH:8]([NH:11][C:17]1[C:16]([O:20][CH3:21])=[C:15]([Cl:22])[N:14]=[C:13]([Cl:12])[N:18]=1)([CH3:10])[CH3:9] | null | CCC(C)=O | 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 |
1,152,393 | CN | null | null | null | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | 2012-01-01T00:04:00 | true | To a solution of 6-chloro-N-methylnicotinoyl chloride (7.39 g, 42.0 mmol) in tetrahydrofuran (50 mL), methylamine (42 mL, 84.0 mmol) and triethylamine (6.4 mL, 46.2 mmol) were added under ice-cold conditions, and the resultant mixture was stirred at room temperature for 3 hours. After completion of the reaction, the reaction solution was concentrated in vacuo, then filtered, and washed with tetrahydrofuran. The obtained residue was recrystallized (ethyl acetate/hexane) and 6-chloro-N-methylnicotinamide (6.52 g, yield 91%) was obtained as a white crystal. | CNC(=O)c1ccc(Cl)nc1 | null | CCN(CC)CC | CN1CC(C(=O)Cl)=CC=C1Cl | null | [Cl:1][C:2]1[N:3](C)[CH2:4][C:5](=[CH:9][CH:10]=1)[C:6](Cl)=[O:7].CN.[CH2:14]([N:16](CC)CC)C>O1CCCC1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:16][CH3:14])=[O:7])=[CH:4][N:3]=1 | null | C1CCOC1 | 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 |
129,097 | CC(C)(C)ON[C@H](C(=O)O)C(=C=O)CSCCNC(=O)OCc1ccccc1 | CCOC(=O)[C@@H]1Cc2ccccc2CN1 | O=C([O-])C(F)(F)F | null | ord_dataset-d6b60b593b1c4668bc6843cd65a5d232 | 1985-01-01T00:04:00 | true | S-(2-Benzyloxycarbonylaminoethyl)-N-tert-butoxy-carbonyl-L-homocysteine (2.14 g., 0.00518 mole) and ethyl 1,2,3,4-tetrahydroisoquinoline-3-(S)-carboxylate (1.12 g., 0.00545 mole) were coupled via the procedure described in Example 5 to give 2.24 g. (72%) of ethyl N-[S-(2-benzyloxycarbonylaminoethyl)-N-tert-butoxycarbonyl-L-homocysteinyl]-1,2,3,4-tetrahydroisoquinoline-3-(S)-carboxylate (1); an oil. Compound 1 (1.10 g., 0.00183 mole) was stirred for 50 minutes at room temperature with 25 ml of trifluoroacetate acid. Concentration in vacuo gave ethyl N-[S-(2-benzyloxycarbonylaminoethyl)-L-homocysteinyl]1,2,3,4-tetrahydroisoquinoline-3-(S)-carboxylate (2) as a crude orange oil. This intermediate (2) was reductively alkylated with 2-oxo-4-phenylbutyric acid (3.00 g., 0.0068 mole) according to the procedure described in Example 5. After chromatography on an LH-20 column with methanol, 0.30 g. (25%) of ethyl N-[S-(2-benzyloxycarbonylaminoethyl)-N-(1-carboxy-3-phenylpropyl)-L-homocysteinyl]-1,2,3,4-tetrahydroisoquinoline-3-(S)-carboxylate (3) was obtained; a colorless oil. | CCOC(=O)[C@@H]1Cc2ccccc2CN1C(=O)[C@@H](N)CCSCCNC(=O)OCc1ccccc1 | null | CCOC(=O)[C@@H]1Cc2ccccc2CN1C(=O)[C@H](CCSCCNC(=O)OCc1ccccc1)NC(=O)OC(C)(C)C | null | null | C(OC(NCCSCC(=C=O)[C@@H](C(O)=O)NOC(C)(C)C)=O)C1C=CC=CC=1.C1C2C(=CC=CC=2)C[C@@H](C(OCC)=O)N1.[CH2:44]([O:51][C:52]([NH:54][CH2:55][CH2:56][S:57][CH2:58][CH2:59][C@@H:60]([C:69]([N:71]1[C@H:80]([C:81]([O:83][CH2:84][CH3:85])=[O:82])[CH2:79][C:78]2[C:73](=[CH:74][CH:75]=[CH:76][CH:77]=2)[CH2:72]1)=[O:70])[NH:61]C(OC(C)(C)C)=O)=[O:53])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1.FC(F)(F)C([O-])=O>>[CH2:44]([O:51][C:52]([NH:54][CH2:55][CH2:56][S:57][CH2:58][CH2:59][C@@H:60]([C:69]([N:71]1[C@H:80]([C:81]([O:83][CH2:84][CH3:85])=[O:82])[CH2:79][C:78]2[C:73](=[CH:74][CH:75]=[CH:76][CH:77]=2)[CH2:72]1)=[O:70])[NH2:61])=[O:53])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=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 |
640,908 | null | null | null | null | ord_dataset-1c0bae7388cf460091d56129e95b3145 | 2004-01-01T00:06:00 | true | The synthesis of the sulfonamide containing carboxylic acid precursor corresponding to the autoinducer analog 10 was accomplished by the two step sequence described below. Accordingly, a solution of α-toluenesulfonyl chloride (10 mmol) in CH2Cl2 (5 mL) was added dropwise to a stirred solution of octylamine (20 mmol) in CH2Cl2 (20 mL) at 0° C. The resulting mixture was subsequently stirred at room temperature for 30 min and was then extracted with H2O (3×24 mL) The organic phase was dried (MgSO4) and the solvent was evaporated in vacuo to provide the corresponding α-toluenesulfonamide (262 mg, 93%) as a colorless solid. Subsequent oxidative degradation of the phenyl moiety within this compound via the procedure of Sharpless, et al. [e.g., cat. RuCl3 hydrate, NaIO4, H2O/CH3CN/CCl4 (vide supra)] furnished the α-sulfonamidoacetic acid corresponding to homoserine lactone 10. Accordingly, a mixture of the above a-toluenesulfonamide (1.00 mmol), CCl4 (2 mL), CH3CN (2 mL), H2O (3 mL) and NaIO4 (14.50 mmol) was vigorously stirred at room temperature and RuCl3 hydrate (5 mg) was added. The reaction mixture was vigorously stirred for a further 2 h at room temperature and then CH2Cl2 (10 mL) was added and the phases were separated. The upper aqueous phase was extracted with three portions of CH2Cl2 and the combined organic phases were dried (MgSO4) and the solvents were removed in vacuo. Recrystallization of the residue from EtOH provided the α-sulfonamidoacetic acid (181 mg, 72%) as a colorless solid. | NS(=O)(=O)Cc1ccccc1 | null | O=S(=O)(Cl)Cc1ccccc1 | CCCCCCCCN | null | [C:1]1([CH2:7][S:8](Cl)(=[O:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([NH2:20])CCCCCCC>C(Cl)Cl>[C:1]1([CH2:7][S:8]([NH2:20])(=[O:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1 | 0.5 | ClCCl | null | null | 25 | 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 |
68,176 | [Mg] | null | null | null | ord_dataset-dabcd66611f34094b1baca0095305a66 | 1980-01-01T00:07:00 | true | To 0.85 gm of magnesium in a thoroughly dried flask equipped with condensor and magnetic stirrer was added 5 mls of anhydrous tetrahydrofuran and 0.5 ml of dibromo ethane. A solution of 4.5 gms of 1,1-dimethoxy-9-chlorononane in 40 mls of toluene was added dropwise. When addition was half complete, a few drops of bromoethane were added and the addition was continued. The temperature was maintained at 75°±5° for two hours. The Grignard reagent was decanted into another flask and 100 mgs of cuprous chloride (CuCl) catalyst was added, followed by dropwise addition of 3.0 gms of a mixture (approximately 60:40) of 1-chloro-2-pentene and 3-chloro-1-pentene dissolved in 15 mls of toluene. The reaction flask was cooled in a water bath at 20°±5°. Magnesium chloride began to precipitate after ten minutes. The reaction stood overnight at room temperature. 50 mls of 3 N hydrochloric acid was added and the reaction mixture was stirred and heated at reflux for 1 hour. The aqueous layer was separated and washed two times with toluene. The organic layer and the toluene washes were combined and dried over sodium sulphate. The solvents were removed on the rotary evaporator and the residue was distilled at 83° at 0.10 torr yielding 2.3 gms of crude 11-tetradecenal. GLC analysis showed that the contaminating 10-ethyl-11-dodecenal was present in only 11.5%. For physical constants see Example 5. | CCC=CCCCCCCCCCC=O | null | CC(Br)Br | COC(CCCCCCCCCl)OC | C1CCOC1 | [Mg].[O:2]1[CH2:6][CH2:5][CH2:4][CH2:3]1.Br[CH:8](Br)[CH3:9].CO[CH:13](OC)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]CCl>C1(C)C=CC=CC=1.BrCC>[CH:3](=[O:2])[CH2:4][CH2:5][CH2:6][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH:14]=[CH:13][CH2:8][CH3:9] | 8 | CCBr | 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 |
742,677 | C(=NC1CCCCC1)=NC1CCCCC1 | Cl | On1nnc2ccccc21 | null | ord_dataset-437aa6654d5044ddaef3346dc4c6e08a | 2006-01-01T00:11:00 | true | At 0° C. the solution of 746 mg (0.81 mmol) of HCl.Arg(Tos)-Pro-Ala-Lys(ClZ)-OBzl (SEQ ID NO: 12) in 50 ml of anhydrous tetrahydrofuran was adjusted to pH 9, to which the pre-cold solution of 340 mg (0.82 mmol) of Boc-Lys(ClZ)-OH, 110 mg (0.82 mmol) of 1-hydroxybenzotriazole and 170 mg (0.82 mmol) of dicyclohexylcarbodiimide in 40 ml of anhydrous tetrahydrofuran was added. The reaction mixture was stirred at 0° C. for 2 h and at room temperature for 16 h and TLC (chloroform/methanol, 10:1) indicated complete disappearance of HCl.Arg(Tos)-Pro-Ala-Lys(ClZ)-OBzl (SEQ ID NO: 12). The resulted precipitates of N,N-dicyclohexylurea were filtrated and the filtrate was diluted with 100 ml of ethyl acetate. The solution obtained was washed successively with saturated NaCO3 in water (50 ml×3), saturated NaCl in water (50 ml×3) and KHSO4 in water (5%, 50 ml×3). The separated ethyl acetate layer was dried with anhydrous MgSO4, and then evaporated. The residue was purified on sinica gel chromatography (CHCl3/CH3OH, 30/1) to provide 850 mg (81%) of the title compound as a glassy mass. Mp 78–88° C., FAB-MS (m/e) 1111.3[M+H]+, 1132.5[M+Na]+, 1010.0[M-Boc]+. | Cc1ccc(S(=O)(=O)NC(=N)NCCC[C@H](NC(=O)[C@H](CCCCNC(=O)OCc2ccccc2Cl)NC(=O)OC(C)(C)C)C(=O)N2CCC[C@H]2C(=O)N[C@@H](C)C(=O)N[C@@H](CCCCNC(=O)OCc2ccccc2Cl)C(=O)OCc2ccccc2)cc1 | null | Cc1ccc(S(=O)(=O)NC(=N)NCCC[C@H](N)C(=O)N2CCC[C@H]2C(=O)N[C@@H](C)C(=O)N[C@@H](CCCCNC(=O)OCc2ccccc2Cl)C(=O)OCc2ccccc2)cc1 | CC(C)(C)OC(=O)N[C@@H](CCCCNC(=O)OCc1ccccc1Cl)C(=O)O | null | Cl.[NH2:2][C@H:3]([C:21]([N:23]1[CH2:62][CH2:61][CH2:60][C@H:24]1[C:25]([NH:27][C@H:28]([C:30]([NH:32][C@H:33]([C:50]([O:52][CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)=[O:51])[CH2:34][CH2:35][CH2:36][CH2:37][NH:38][C:39]([O:41][CH2:42][C:43]1[CH:49]=[CH:48][CH:47]=[CH:46][C:44]=1[Cl:45])=[O:40])=[O:31])[CH3:29])=[O:26])=[O:22])[CH2:4][CH2:5][CH2:6][NH:7][C:8](=[NH:20])[NH:9][S:10]([C:13]1[CH:19]=[CH:18][C:16]([CH3:17])=[CH:15][CH:14]=1)(=[O:12])=[O:11].[NH:63]([C:84]([O:86][C:87]([CH3:90])([CH3:89])[CH3:88])=[O:85])[C@H:64]([C:81](O)=[O:82])[CH2:65][CH2:66][CH2:67][CH2:68][NH:69][C:70]([O:72][CH2:73][C:74]1[CH:80]=[CH:79][CH:78]=[CH:77][C:75]=1[Cl:76])=[O:71].ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1.C(Cl)(Cl)Cl.CO>[NH:63]([C:84]([O:86][C:87]([CH3:90])([CH3:89])[CH3:88])=[O:85])[C@H:64]([C:81]([NH:2][C@H:3]([C:21]([N:23]1[CH2:62][CH2:61][CH2:60][C@H:24]1[C:25]([NH:27][C@H:28]([C:30]([NH:32][C@H:33]([C:50]([O:52][CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)=[O:51])[CH2:34][CH2:35][CH2:36][CH2:37][NH:38][C:39]([O:41][CH2:42][C:43]1[CH:49]=[CH:48][CH:47]=[CH:46][C:44]=1[Cl:45])=[O:40])=[O:31])[CH3:29])=[O:26])=[O:22])[CH2:4][CH2:5][CH2:6][NH:7][C:8](=[NH:20])[NH:9][S:10]([C:13]1[CH:14]=[CH:15][C:16]([CH3:17])=[CH:18][CH:19]=1)(=[O:11])=[O:12])=[O:82])[CH2:65][CH2:66][CH2:67][CH2:68][NH:69][C:70]([O:72][CH2:73][C:74]1[CH:80]=[CH:79][CH:78]=[CH:77][C:75]=1[Cl:76])=[O:71] | 16 | ClC(Cl)Cl | CO | C1CCOC1 | 0 | null | 81 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
530,974 | O=C([O-])[O-] | [K+] | null | null | ord_dataset-7774db17e619477ea20ee621abe71257 | 2002-01-01T00:01:00 | true | 3.0 g of 4-chloro-5-formyl-2-phenylimidazole (Chem. Pharm. Bull. 1976, 24(5), 960), 7.0 g of 4-bromobenzyl bromide and 11.7 g of K2CO3 are stirred at RT for 20 h in 200 ml of DMF. The reaction mixture is then poured onto 500 ml of water, and the precipitate is filtered off with suction and chromatographed on silica gel using DIP. 3.9 g of an amorphous foam are obtained. | O=Cc1c(Cl)nc(-c2ccccc2)n1Cc1ccc(Br)cc1 | null | BrCc1ccc(Br)cc1 | O=Cc1[nH]c(-c2ccccc2)nc1Cl | null | [Cl:1][C:2]1[N:3]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:5][C:6]=1[CH:7]=[O:8].[Br:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Br)=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Br:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][N:5]2[C:6]([CH:7]=[O:8])=[C:2]([Cl:1])[N:3]=[C:4]2[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:18][CH:17]=1 | null | O | CN(C)C=O | null | null | 71.5 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,132,807 | null | null | null | null | ord_dataset-aaeaab5f3720492494c1cbbdd0ed2820 | 2012-01-01T00:02:00 | true | A mixture of tert-butyl 2-(4-(1-oxo-6-propylisoindolin-2-yl)phenyl)propanoate (0.084 g, 0.22 mmol) and formic acid (15 mL) was stirred overnight at room temperature. The mixture was then concentrated under reduced pressure, suspended in hexanes (5 mL), sonicated, and the solid collected by filtration to afford 2-(4-(1-oxo-6-propylisoindolin-2-yl)phenyl)propanoic acid (0.041 g, 57%) as a white solid: mp 175-177° C.; 1H NMR (300 MHz, CDCl3) δ 7.83 (d, J=8.6 Hz, 2H), 7.74 (s, 1H), 7.41-7.37 (m, 4H), 4.81 (s, 2H), 3.77 (q, J=7.1 Hz, 1H), 2.70 (t, J=7.4 Hz, 2H), 1.73-1.65 (m, 2H), 1.54 (d, J=7.2 Hz, 3H), 0.95 (t, J=7.3 Hz, 3H); ESI MS m/z 324 [M+H]+. | CCCc1ccc2c(c1)C(=O)N(c1ccc(C(C)C(=O)O)cc1)C2 | null | CCCc1ccc2c(c1)C(=O)N(c1ccc(C(C)C(=O)OC(C)(C)C)cc1)C2 | null | null | [O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:11][CH2:12][CH3:13])[CH:9]=2)[CH2:4][N:3]1[C:14]1[CH:19]=[CH:18][C:17]([CH:20]([CH3:28])[C:21]([O:23]C(C)(C)C)=[O:22])=[CH:16][CH:15]=1>C(O)=O>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:11][CH2:12][CH3:13])[CH:9]=2)[CH2:4][N:3]1[C:14]1[CH:19]=[CH:18][C:17]([CH:20]([CH3:28])[C:21]([OH:23])=[O:22])=[CH:16][CH:15]=1 | 8 | O=CO | null | null | 25 | 57.6 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
374,748 | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | ord_dataset-ee5599340390470d8e5b5ac1feddf9d6 | 1997-01-01T00:08:00 | true | The alcohol of Example 17 is dissolved in 5 mL of nitro ethyl acetate. A catalytic amount of p-toluene-sulfonic acid is added and the reaction mixture is heated to 120° C. for 3 hours. Excess nitro ethyl acetate is removed by distillation and the residue is purified by silica gel chromatography eluting with 15% ethyl acetate-hexane to give 2.25 g (79%) of product as a yellow oil; | CCOC(=O)C(C(c1ccc2c(c1)OCO2)c1ccc2c(c1)OCO2)[N+](=O)[O-] | null | CCOC(=O)C[N+](=O)[O-] | OC(c1ccc2c(c1)OCO2)c1ccc2c(c1)OCO2 | null | [O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([C:12]3[CH:20]=[CH:19][C:15]4[O:16][CH2:17][O:18][C:14]=4[CH:13]=3)O)=[CH:9][C:4]=2[O:3][CH2:2]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:32][CH2:33][O:34][C:35]([CH2:37][N+:38]([O-:40])=[O:39])=[O:36]>>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([C:12]3[CH:20]=[CH:19][C:15]4[O:16][CH2:17][O:18][C:14]=4[CH:13]=3)[CH:37]([N+:38]([O-:40])=[O:39])[C:35]([O:34][CH2:33][CH3:32])=[O:36])=[CH:9][C:4]=2[O:3][CH2:2]1 | null | null | null | null | 120 | null | 79 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
568,700 | [H-] | [Na+] | null | null | ord_dataset-5e1b2445a3d94ea592ddf2c284118a1e | 2002-01-01T00:11:00 | true | The product from Example 21, step e) (0.4 g, 0.0009 mol) and (2-methyl-2H-[1,2,4]triazol-3-yl)methanol (0.12 g, 0.0011 mol) were dissolved in dry N,N-dimethylformamide (10 ml) under nitrogen and sodium hydride (60% wt in oil) (0.035 g, 0.0009 mol) was added. The solution was stirred at room temperature for 3 h after which solvent was removed in vacuo and the residue was purified using silica gel chromatography with 0%→60% ethyl acetate/dichloromethane as eluent. Trituration with isohexane and recrystallisation from ethyl acetate/isohexane gave the required product (0.137 g, mp=144° C.). Data for the title compound: 1H NMR (400 MHz, CDCl3) δ 1.50 (9H, s), 3.84 (3H, s), 5.48 (2H, s), 7.18-7.26 (1H, m), 7.27-7.35 (1H, m), 7.47 (1H, m), 7.87 (1H, s), 9.41 (1H, s); MS (ES+) m/e 400 [MH]+; Anal. Found: C, 57.30; H, 4.64; N, 24.64%. C19H19F2N7O requires: C, 57.14; H, 4.79; N, 24.55%. | Cn1ncnc1COc1nn2c(-c3cc(F)ccc3F)nncc2c1C(C)(C)C | null | Cn1ncnc1CO | Cc1ccc(S(=O)(=O)Oc2nn3c(-c4cc(F)ccc4F)nncc3c2C(C)(C)C)cc1 | null | [C:1]([C:5]1[C:6]([O:22]S(C2C=CC(C)=CC=2)(=O)=O)=[N:7][N:8]2[C:13]=1[CH:12]=[N:11][N:10]=[C:9]2[C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[F:21])([CH3:4])([CH3:3])[CH3:2].[CH3:33][N:34]1[C:38]([CH2:39]O)=[N:37][CH:36]=[N:35]1.[H-].[Na+]>CN(C)C=O>[F:21][C:15]1[CH:16]=[CH:17][C:18]([F:20])=[CH:19][C:14]=1[C:9]1[N:8]2[N:7]=[C:6]([O:22][CH2:39][C:38]3[N:34]([CH3:33])[N:35]=[CH:36][N:37]=3)[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[C:13]2[CH:12]=[N:11][N:10]=1 | 3 | CN(C)C=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 |
1,217,793 | CC(C)(C)[O-] | Cl | [K+] | null | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | 2012-01-01T00:10:00 | true | Bis(dibenzylidineacetone)palladium (2 mg, 0.0035 mmol) and (2′-dicyclohexyl phosphanyl-biphenyl-2-yl)-dimethylamine (3.3 mg, 0.0084 mmol) were added to dry toluene (10 mL purged with argon) and stirred for 15 minutes under argon. Potassium tert-butoxide (197 mg, 1.75 mmol), 6-methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride salt (134 mg, 0.67 mmol) and N-(4-bromo-2,6-dimethyphenyl)-3,3-dimethylbutanamide (200 mg, 0.67 mmol) were then added and the reaction mixture was stirred at 80° C. overnight. The reaction mixture was then cooled to room temperature, concentrated, filtered through a pad of silica gel, and recrystallized from toluene to afford the title compound as a solid. | COc1ccc2c(c1)CCN(c1cc(C)c(NC(=O)CC(C)(C)C)c(C)c1)C2 | null | Cc1cc(Br)cc(C)c1NC(=O)CC(C)(C)C | COc1ccc2c(c1)CCNC2 | null | CC(C)([O-])C.[K+].Cl.[CH3:8][O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH2:16][NH:15][CH2:14][CH2:13]2.Br[C:21]1[CH:26]=[C:25]([CH3:27])[C:24]([NH:28][C:29](=[O:35])[CH2:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[C:23]([CH3:36])[CH:22]=1>C1(C)C=CC=CC=1>[CH3:8][O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH2:16][N:15]([C:21]1[CH:26]=[C:25]([CH3:27])[C:24]([NH:28][C:29](=[O:35])[CH2:30][C:31]([CH3:32])([CH3:33])[CH3:34])=[C:23]([CH3:36])[CH:22]=1)[CH2:14][CH2:13]2 | 0.25 | Cc1ccccc1 | 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 |
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