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 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
1,139,428 | C[Al](C)C | null | null | null | ord_dataset-68715347640045adb1b09e6a04722b0e | 2012-01-01T00:03:00 | true | Trimethylaluminium (2M in toluene, 1.92 mL, 3.85 mmol) was added dropwise to a stirred suspension of 5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-amine (381 mg, 1.54 mmol) and methyl 2-(4-cyclopropylpiperazin-1-yl)pyrimidine-5-carboxylate (404 mg, 1.54 mmol) in toluene (7.7 mL) at 25° C. The resulting solution was stirred at ambient temperature for 18 h and then heated at 60° C. for 2 h. The reaction mixture was quenched with methanol (20 mL) and treated with HCl (2N aqueous solution). The crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M NH3/MeOH and evaporated to dryness to afford impure product. The impure material was purified by preparative HPLC, using decreasingly polar mixtures of water (containing 0.1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford the title compound (100 mg, 14%) as a solid. | COc1cc(CCc2cc(NC(=O)c3cnc(N4CCN(C5CC5)CC4)nc3)[nH]n2)cc(OC)c1 | null | COC(=O)c1cnc(N2CCN(C3CC3)CC2)nc1 | COc1cc(CCc2cc(N)[nH]n2)cc(OC)c1 | null | C[Al](C)C.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH2:15][CH2:16][C:17]2[CH:18]=[C:19]([NH2:22])[NH:20][N:21]=2)[CH:10]=[C:11]([O:13][CH3:14])[CH:12]=1.[CH:23]1([N:26]2[CH2:31][CH2:30][N:29]([C:32]3[N:37]=[CH:36][C:35]([C:38](OC)=[O:39])=[CH:34][N:33]=3)[CH2:28][CH2:27]2)[CH2:25][CH2:24]1>C1(C)C=CC=CC=1>[CH:23]1([N:26]2[CH2:27][CH2:28][N:29]([C:32]3[N:37]=[CH:36][C:35]([C:38]([NH:22][C:19]4[NH:20][N:21]=[C:17]([CH2:16][CH2:15][C:9]5[CH:8]=[C:7]([O:6][CH3:5])[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=5)[CH:18]=4)=[O:39])=[CH:34][N:33]=3)[CH2:30][CH2:31]2)[CH2:25][CH2:24]1 | 18 | Cc1ccccc1 | null | null | 25 | null | 13.6 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,596,087 | [H-] | [Na+] | null | null | ord_dataset-e8c6a25568b64529b960953990e6921f | 2015-01-01T00:06:00 | true | To a solution of (±)-(7-methyl-4-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)-1-tosyl-1H-indol-5-yl)methanol (Example 52-C) (170 mg, 0.40 mmol) in DMF (1 mL) was added NaH (31.7 mg, 60% in mineral oil, 0.79 mmol) at room temperature, and then the mixture was stirred for 10 min. To the mixture was added MeI (25 uL, 0.40 mmol) at room temperature, and then the mixture was stirred for 2.5 h. The reaction was quenched by half saturated aqueous solution of KHSO4, and diluted with EtOAc. The bi-layer was partitioned. The organic phase was washed successively H2O and brine, dried over Na2SO4, and then filtered. Concentration of the filtrate gave the title compound, without need of any further purification. 1H NMR (400 MHz, DMSO-d6) δ 7.86 (d, J=3.79 Hz, 1H), 7.62 (d, J=8.34 Hz, 2H), 7.39 (d, J=8.34 Hz, 2H), 7.08 (s, 1H), 6.99 (d, J=3.79 Hz, 1H), 4.87 (d, J=11.37 Hz, 1H), 4.67 (d, J=11.37 Hz, 1H), 4.60-4.64 (m, 1H), 4.44-4.54 (m, 2H), 3.73-3.86 (m, 1H), 3.41-3.52 (m, 1H), 3.30 (s, 3H), 2.47 (s, 3H), 2.34 (s, 3H), 1.51-1.78 (m, 2H), 1.34-1.51 (m, 4H). | COCc1cc(C)c2c(ccn2S(=O)(=O)c2ccc(C)cc2)c1COC1CCCCO1 | null | Cc1ccc(S(=O)(=O)n2ccc3c(COC4CCCCO4)c(CO)cc(C)c32)cc1 | CI | null | [CH3:1][C:2]1[CH:3]=[C:4]([CH2:29][OH:30])[C:5]([CH2:21][O:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][O:24]2)=[C:6]2[C:10]=1[N:9]([S:11]([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH:8]=[CH:7]2.[H-].[Na+].[CH3:33]I>CN(C=O)C>[CH3:33][O:30][CH2:29][C:4]1[C:5]([CH2:21][O:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][O:24]2)=[C:6]2[C:10](=[C:2]([CH3:1])[CH:3]=1)[N:9]([S:11]([C:14]1[CH:15]=[CH:16][C:17]([CH3:18])=[CH:19][CH:20]=1)(=[O:13])=[O:12])[CH:8]=[CH:7]2 | 0.17 | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,077,709 | O=C1CCC(=O)N1Br | null | null | null | ord_dataset-afd812677c134591a99f46ce28de2524 | 2011-01-01T00:08:00 | true | To a solution of N-{3-[(Z)-2-(2-chloro-4-pyrimidinyl)-1-hydroxyethenyl]phenyl}-2,5-difluorobenzenesulfonamide (1.0 g, 2.4 mmol) in 25 mL DMA, NBS (0.420 g, 2.4 mmol) was added and the solution was allowed to stir 15 minutes at rt. 2,2-Dimethylpropanethioamide (0.277 g, 2.359 mmol) was then added and the reaction mixture was heated at 80° C. for 2 h. The reaction mixture was diluted with EtOAc and washed with water ×3. The organic layer was dried over MgSO4 and filtered. The organic solution was evaporated onto silica gel and chromatographed. 0-50% EtOAc in DCM to give the title compound (1.01 g, 81% yield). ES-LCMS m/z 521.1 (M+H). | CC(C)(C)c1nc(-c2cccc(NS(=O)(=O)c3cc(F)ccc3F)c2)c(-c2ccnc(Cl)n2)s1 | null | O=S(=O)(Nc1cccc(/C(O)=C/c2ccnc(Cl)n2)c1)c1cc(F)ccc1F | CC(C)(C)C(N)=S | null | [Cl:1][C:2]1[N:7]=[C:6](/[CH:8]=[C:9](/[C:11]2[CH:12]=[C:13]([NH:17][S:18]([C:21]3[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=3[F:28])(=[O:20])=[O:19])[CH:14]=[CH:15][CH:16]=2)\O)[CH:5]=[CH:4][N:3]=1.C1C(=O)N(Br)C(=O)C1.[CH3:37][C:38]([CH3:43])([CH3:42])[C:39](=[S:41])[NH2:40]>CC(N(C)C)=O.CCOC(C)=O.C(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[S:41][C:39]([C:38]([CH3:43])([CH3:42])[CH3:37])=[N:40][C:9]=2[C:11]2[CH:12]=[C:13]([NH:17][S:18]([C:21]3[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=3[F:28])(=[O:20])=[O:19])[CH:14]=[CH:15][CH:16]=2)[CH:5]=[CH:4][N:3]=1 | 0.25 | ClCCl | CC(=O)N(C)C | CCOC(C)=O | 25 | null | 82.2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,366,466 | O=S(=O)([O-])C(F)(F)F | [Yb+3] | null | null | ord_dataset-d932d1d683704a8bad3d064bcb197acc | 2013-01-01T00:11:00 | true | To a mixture of 4-{[1-(3-bromo-5-fluoro-phenyl)-methylidene]-amino}-benzoic acid ethyl ester (2.25 g, 6.43 mmol) and ytterbium(III) triflate hydrate (0.40 g, 0.64 mmol) in dry tetrahydrofuran (10 mL) at 25° C. was added isobutyraldehyde (0.59 mL, 6.43 mmol) and water (0.12 mL, 6.43 mmol) dropwise. The reaction mixture was stirred at 25° C. for 5 h. Then the reaction mixture was concentrated in vacuo and the residue was extracted with ethyl acetate (2×100 mL), washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to afford 2-(3-bromo-5-fluoro-phenyl)-4-hydroxy-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (2.33 g, 86%) as a light yellow oil: LC/MS m/e calcd for C20H21BrFNO3 M+: 422.3, observed: 404.3, 406.3. | CCOC(=O)c1ccc2c(c1)C(O)C(C)(C)C(c1cc(F)cc(Br)c1)N2 | null | CCOC(=O)c1ccc(N=Cc2cc(F)cc(Br)c2)cc1 | CC(C)C=O | null | [CH2:1]([O:3][C:4](=[O:21])[C:5]1[CH:10]=[CH:9][C:8]([N:11]=[CH:12][C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[C:15]([Br:20])[CH:14]=2)=[CH:7][CH:6]=1)[CH3:2].O.[O-]S(C(F)(F)F)(=O)=O.[Yb+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O.[CH:48](=[O:52])[CH:49]([CH3:51])[CH3:50].O>O1CCCC1>[CH2:1]([O:3][C:4]([C:5]1[CH:10]=[C:9]2[C:8](=[CH:7][CH:6]=1)[NH:11][CH:12]([C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[C:15]([Br:20])[CH:14]=1)[C:49]([CH3:51])([CH3:50])[CH:48]2[OH:52])=[O:21])[CH3:2] | 5 | O | C1CCOC1 | null | 25 | 85.8 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
350,064 | [Na+] | null | null | null | ord_dataset-66f304805e5d47fc8d3c722b1bd8dfa2 | 1996-01-01T00:12:00 | true | (5)To a solution of 2.89 g of methyl (2R,3R)-3-cyclopropyl-2,3-epoxypropionate in 112.5 ml of methanol-water (8:1) are added 14 ml of methyl formate and 16.60 g of sodium azide. Then, the reaction mixture is stirred at 50° C. overnight. The reaction mixture is cooled to room temperature and evaporated to remove methanol. The residue is dissolved in ethyl acetate. The solution is washed with brine and dried. The solvent is removed in vacuo. The residue is purified by silica gel column chromatography (solvent; hexane:ethyl acetate=4:l) to give 2.61 g of methyl (2R,3S)-3-cyclopropyl-3-azido--2-hydroxypropionate. | COC(=O)[C@H](O)[C@@H](N=[N+]=[N-])C1CC1 | null | [N-]=[N+]=[N-] | COC(=O)[C@@H]1O[C@@H]1C1CC1 | null | [CH:1]1([C@H:4]2[O:10][C@H:5]2[C:6]([O:8][CH3:9])=[O:7])[CH2:3][CH2:2]1.C(OC)=O.[N-:15]=[N+:16]=[N-:17].[Na+]>CO.O>[CH:1]1([C@H:4]([N:15]=[N+:16]=[N-:17])[C@@H:5]([OH:10])[C:6]([O:8][CH3:9])=[O:7])[CH2:3][CH2:2]1 | 8 | CO | COC=O | O | 50 | null | 69.3 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,682,122 | CC(=O)[O-] | Cl | [NH4+] | null | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | 2016-01-01T00:01:00 | true | In a similar fashion to Compound LXXXVII, (1S,2S,3R,4R)-3-(2,3-Diamino-5-chloro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide (75.00 mg, 0.2553 mmol), 1-Methyl-piperidine-4-carbaldehyde; hydrochloride (46.0 mg, 0.281 mmol), Ammonium acetate (39.4 mg, 0.511 mmol), and N,N-Diisopropylethylamine (53.37 uL, 0.3064 mmol) were reacted to produce 21.99 mg (21%) of the title compound. (300 MHz, DMSO-d6) 12.52 (s, 1H), 7.86 (s, 1H), 7.72 (s, 1H), 7.18 (s, 1H), 6.95 (d, J=9 Hz, 1H), 6.29 (m, 2H), 5.09 (t, J=17 Hz, 8.5 Hz, 1H), 2.87-2.54 (m, 7H), 2.18 (s, 3H), 1.98 (m, 4H), 1.81 (m, 2H), 1.38 (d, J=8 Hz, 1H). MS=499 (M+H), HPLC: 2.47 min. (G Method) | CN1CCC(c2nc3c(N[C@H]4[C@@H](C(N)=O)[C@@H]5C=C[C@H]4C5)c(Cl)cnc3[nH]2)CC1 | null | NC(=O)[C@@H]1[C@H](Nc2c(Cl)cnc(N)c2N)[C@H]2C=C[C@@H]1C2 | CN1CCC(C=O)CC1 | null | [NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([NH:9][C@@H:10]2[C@@H:15]3[CH2:16][C@@H:12]([CH:13]=[CH:14]3)[C@@H:11]2[C:17]([NH2:19])=[O:18])[C:5]([Cl:20])=[CH:4][N:3]=1.[CH3:21][N:22]1[CH2:27][CH2:26][CH:25]([CH:28]=O)[CH2:24][CH2:23]1.Cl.C([O-])(=O)C.[NH4+].C(N(CC)C(C)C)(C)C>>[Cl:20][C:5]1[C:6]([NH:9][C@@H:10]2[C@@H:15]3[CH2:16][C@@H:12]([CH:13]=[CH:14]3)[C@@H:11]2[C:17]([NH2:19])=[O:18])=[C:7]2[N:8]=[C:28]([CH:25]3[CH2:26][CH2:27][N:22]([CH3:21])[CH2:23][CH2:24]3)[NH:1][C:2]2=[N:3][CH:4]=1 | null | CCN(C(C)C)C(C)C | null | null | null | 21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,107,955 | [Pd] | null | null | null | ord_dataset-375a420ee9b042918ddca20f02df37d3 | 2011-01-01T00:11:00 | true | A suspension of 1-(2-fluoro-4-nitrophenyl)-1H-pyrazole (1.80 g, 8.70 mmol) and Pd—C (10%, 0.200 g) in MeOH (20 mL) (containing 10 drops of 6N HCl) was hydrogenated under balloon H2 overnight. The mixture was filtered through celite. The filtrate was concentrated in vacuo. The residue was dried on vacuum to give 3-fluoro-4-(1H-pyrazol-1-yl)benzenamine as a solid (1.55 g). MS 178.3 (M+H) | Nc1ccc(-n2cccn2)c(F)c1 | null | O=[N+]([O-])c1ccc(-n2cccn2)c(F)c1 | null | null | [F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[N:11]1[CH:15]=[CH:14][CH:13]=[N:12]1>CO.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[N:11]1[CH:15]=[CH:14][CH:13]=[N:12]1 | null | CO | null | null | null | null | 100.6 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
45,680 | Cl | null | null | null | ord_dataset-becaf7dc22c44672b22e4b94335cbf08 | 1978-01-01T00:09:00 | true | By the reaction of ethyl α,α-dimethyl-β-[4-(2-aminoethyl)-phenyl]-propionate hydrochloride with 5-chloro-2-methoxybenzoyl chloride, there is obtained α,α-dimethyl-β-{4-[2-(5-chloro-2-methoxybenzamido)-ethyl]-phenyl}-propionic acid; m.p. 138°-141° C., after recrystallization from ethyl acetate. | COc1ccc(Cl)cc1C(=O)NCCc1ccc(CC(C)(C)C(=O)O)cc1 | null | CCOC(=O)C(C)(C)Cc1ccc(CCN)cc1 | COc1ccc(Cl)cc1C(=O)Cl | null | Cl.[CH3:2][C:3]([CH3:19])([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][NH2:18])=[CH:12][CH:11]=1)[C:4]([O:6]CC)=[O:5].[Cl:20][C:21]1[CH:22]=[CH:23][C:24]([O:30][CH3:31])=[C:25]([CH:29]=1)[C:26](Cl)=[O:27]>>[CH3:19][C:3]([CH3:2])([CH2:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][NH:18][C:26](=[O:27])[C:25]2[CH:29]=[C:21]([Cl:20])[CH:22]=[CH:23][C:24]=2[O:30][CH3:31])=[CH:14][CH:15]=1)[C:4]([OH:6])=[O:5] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
9,238 | O=C(O)CCl | null | null | null | ord_dataset-ad879e603f9440f6bfb7fbd18e5e8761 | 1976-01-01T00:06:00 | true | It is also known to use 4- or Γ-mercaptopyridine as the starting compound. For instance, in J. Chem. Soc. 1939 873-877, King and Ware described the preparation of 4-pyridylthioacetic acid by treating 4-mercapto-pyridine with ClCH2COOH in a weakly basic medium, while Takahashi et al, as described in Pharm. Bull. (Japan) 2 30-34 (1954), obtain methyl-4-pyridylthioacetate by heating 4-mercaptopyridine for one hour on a water-bath with ClCH2CO2Me. In Gazz. Chim. Ital. 84 584-594 (1954), Musante and Fabbrini mention the preparation of 4-pyridylthioacetic acid by causing 4-mercapto-pyridine to react with ClCH2CONEt2 and treating the resulting 4-(diethylcarbamoylmethylmercapto)pyridine with KOH. In Wiss. Z. Tech. Hochsch. Chem. Leuna-Merseburg 2 187-193 (1959-1960) the preparation of (2-methyl-4-pyridylthio)acetic acid from ClCH2CO2H and 4-mercapto-2-methylpyridine is mentioned, the latter product being obtained by converting 4-nitro-2-methylpyridine-N-oxide into 4-chloro-2-methyl-pyridine and causing this to react with KHS. | COC(=S)Cc1ccncc1 | null | Sc1ccncc1 | OC(=S)Cc1ccncc1 | null | [N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]([OH:10])=[S:9])=[CH:3][CH:2]=1.S[C:12]1C=CN=CC=1.ClCC(O)=O>>[CH3:12][O:10][C:8](=[S:9])[CH2:7][C:4]1[CH:5]=[CH:6][N:1]=[CH:2][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 |
706,050 | Cl | null | null | null | ord_dataset-c408dfed796e4354b61e312e67f7143f | 2006-01-01T00:04:00 | true | To tert-butyl[2-isobutyl-6-(5-methyl-1,3,4-oxadiazol-3-yl)-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.20 g, 0.41 mmol) was added a solution (4 mL) of 4N hydrogen chloride in ethyl acetate and the mixture was stirred at room temperature for 17 h. The reaction mixture was concentrated under reduced pressure and to the residue was added diisopropyl ether (5 mL). The precipitated powder was collected by filtration. To this powder was added saturated aqueous sodium hydrogencarbonate (30 mL) and the mixture was extracted twice with a solution (25 mL) of ethyl acetate-tetrahydrofuran (1:1). The organic layers were combined and the mixture was washed with saturated brine (25 mL), dried over anhydrous magnesium sulfate (15 g) and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=20:1, (v/v)) and recrystallized from n-hexane-ethyl acetate (5:1) to give the title compound (0.11 g, 72%) as pale-yellow crystals. | CC1=NN(c2ccc3c(=O)n(CC(C)C)c(CN)c(-c4ccccc4)c3c2)CO1 | null | CC1=NN(c2ccc3c(=O)n(CC(C)C)c(CNC(=O)OC(C)(C)C)c(-c4ccccc4)c3c2)CO1 | null | null | C(OC(=O)[NH:7][CH2:8][C:9]1[N:10]([CH2:32][CH:33]([CH3:35])[CH3:34])[C:11](=[O:31])[C:12]2[C:17]([C:18]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[CH:16][C:15]([N:25]1[N:29]=[C:28]([CH3:30])[O:27][CH2:26]1)=[CH:14][CH:13]=2)(C)(C)C.Cl>C(OCC)(=O)C>[NH2:7][CH2:8][C:9]1[N:10]([CH2:32][CH:33]([CH3:35])[CH3:34])[C:11](=[O:31])[C:12]2[C:17]([C:18]=1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[CH:16][C:15]([N:25]1[N:29]=[C:28]([CH3:30])[O:27][CH2:26]1)=[CH:14][CH:13]=2 | 17 | CCOC(C)=O | null | null | 25 | null | 68.7 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
716,545 | Cl | null | null | null | ord_dataset-c8a367b56b4f406b878f51867b157d19 | 2006-01-01T00:06:00 | true | Prepared by Procedure E and Scheme M using 2-methyl-N-(3-{1-[5-(3-nitrophenyl)-5-oxopentyl]-4-piperidinyl}phenyl)propanamide and 1,1-diphenylhydrazine hydrochloride: ESMS m/e: 601.1 (M+H)+. | CC(C)C(=O)Nc1cccc(C2CCN(CCCc3c(-c4cccc([N+](=O)[O-])c4)n(-c4ccccc4)c4ccccc34)CC2)c1 | null | CC(C)C(=O)Nc1cccc(C2CCN(CCCCC(=O)c3cccc([N+](=O)[O-])c3)CC2)c1 | NN(c1ccccc1)c1ccccc1 | null | [CH3:1][CH:2]([CH3:33])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH2:20][CH2:21][C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([N+:30]([O-:32])=[O:31])[CH:25]=3)=O)[CH2:14][CH2:13]2)[CH:7]=1)=[O:4].Cl.[C:35]1([N:41]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)N)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>>[CH3:33][CH:2]([CH3:1])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH2:20][C:21]3[C:36]4[C:35](=[CH:40][CH:39]=[CH:38][CH:37]=4)[N:41]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[C:22]=3[C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([N+:30]([O-:32])=[O:31])[CH:25]=3)[CH2:14][CH2:13]2)[CH:7]=1)=[O:4] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
246,577 | null | null | null | null | ord_dataset-75ca79f43dad4cc8a934fe6487fa8eb1 | 1992-01-01T00:05:00 | true | A mixture of 0.51 g of 4,5-dihydro-6-(4-aminophenyl)-5-methyl-3(2H) pyridazinone and 0.28 g of 2-methyl-cyclopentane-1,3-dione in 5 ml of ethanol and 5 ml of acetic acid was refluxed over night. After cooling, the solution was evaporated in vacuo. The residue was purified by silica gel column chromatography (eluting solvent: chloroform:methanol=20:1) and recrystallized from methanol to give 0.32 g of the title compound. m.p. 285°-286° C. | CC1=C(Nc2ccc(C3=NNC(=O)CC3C)cc2)CCC1=O | null | CC1CC(=O)NN=C1c1ccc(N)cc1 | CC1C(=O)CCC1=O | null | [NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1.[CH3:16][CH:17]1[C:21](=[O:22])[CH2:20][CH2:19][C:18]1=O>C(O)C.C(O)(=O)C>[CH3:16][C:17]1[C:21](=[O:22])[CH2:20][CH2:19][C:18]=1[NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1 | null | CC(=O)O | CCO | null | null | 43.1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,266,674 | [Li+] | [OH-] | null | null | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | 2013-01-01T00:03:00 | true | A mixture of 5-benzenesulfonyl-2-methylsulfanylpyrimidine-4-carboxylic acid methyl ester (1.4 g) and tetrahydrofuran (20 mL) was treated with 1.0 M aqueous lithium hydroxide solution (2.2 mL), and the resulting mixture was stirred at room temperature for 1 hour. The mixture was concentrated under reduced pressure, pH adjusted to 4 by the addition of 0.1 M aqueous hydrochloric acid solution and extracted with ethyl acetate. The combined extract was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure to afford the title compound as a pale yellow solid (1.3 g). | CSc1ncc(S(=O)(=O)c2ccccc2)c(C(=O)O)n1 | null | COC(=O)c1nc(SC)ncc1S(=O)(=O)c1ccccc1 | null | null | C[O:2][C:3]([C:5]1[C:10]([S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[CH:9][N:8]=[C:7]([S:20][CH3:21])[N:6]=1)=[O:4].[OH-].[Li+]>O1CCCC1>[C:14]1([S:11]([C:10]2[C:5]([C:3]([OH:4])=[O:2])=[N:6][C:7]([S:20][CH3:21])=[N:8][CH:9]=2)(=[O:13])=[O:12])[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1 | 1 | C1CCOC1 | null | null | 25 | 97.1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
351,716 | [Li]CCCC | null | null | null | ord_dataset-127eb5fdd5b4402e92b51d0b55a5dcb5 | 1997-01-01T00:01:00 | true | This compound is prepared in a manner analogous to that of Step B of Example 6, using 9.1 grams (0.032 mole) of 3-fluoro-5-(4-fluorophenoxy)phenyl bromide, 14 mL (0.035 mole) of n-butyllithium (2.5M in hexanes), and 10.4 mL (0.095 mole) of trimethyl borate in 100 mL of tetrahydrofuran, yielding 3-fluoro-5-(4-fluorophenoxy)phenylboronic acid. | OB(O)c1cc(F)cc(Oc2ccc(F)cc2)c1 | null | Fc1ccc(Oc2cc(F)cc(Br)c2)cc1 | COB(OC)OC | null | [F:1][C:2]1[CH:3]=[C:4](Br)[CH:5]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[CH:7]=1.C([Li])CCC.[B:22](OC)([O:25]C)[O:23]C>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([B:22]([OH:25])[OH:23])[CH:5]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[CH:7]=1 | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,233,779 | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])O | [Na+] | null | ord_dataset-e96f5a2842f14e5380461c234100f05a | 2012-01-01T00:12:00 | true | To toluene 2.1 mL solution of tert-butyl 4-bromo-2-(4-fluoroanilino)benzoate 0.10 g were added ethanol 0.6 mL, water 0.3 mL, 3-fluorophenylboronic acid 46 mg, sodium hydrogen carbonate 69 mg and tetrakis(triphenylphosphine)palladium(0) 16 mg at room temperature, and it was heated and refluxed for 2 hours. After the reaction mixture was cooled to room temperature, tetrakis(triphenylphosphine)palladium(0) 16 mg were added, and it was heated and refluxed for 2 hours. After the reaction mixture was cooled to room temperature, toluene and saturated sodium hydrogen carbonate aqueous solution were added to it. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after washing with saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Trikonex company, Flash Tube 2008, eluent; hexane:ethyl acetate=10:1] to give tert-butyl 2-(4-fluoroanilino)-4-(3-fluorophenyl)benzoate. | CC(C)(C)OC(=O)c1ccc(-c2cccc(F)c2)cc1Nc1ccc(F)cc1 | null | CC(C)(C)OC(=O)c1ccc(Br)cc1Nc1ccc(F)cc1 | OB(O)c1cccc(F)c1 | null | Br[C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[C:4]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH:3]=1.[F:23][C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=1.C(=O)([O-])O.[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1.O.C(O)C>[F:22][C:19]1[CH:20]=[CH:21][C:16]([NH:15][C:4]2[CH:3]=[C:2]([C:28]3[CH:27]=[CH:26][CH:25]=[C:24]([F:23])[CH:29]=3)[CH:14]=[CH:13][C:5]=2[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[CH:17][CH:18]=1 | null | O | CCO | Cc1ccccc1 | 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 |
472,963 | null | null | null | null | ord_dataset-cd531114850e4f239b2a3661044ae672 | 2000-01-01T00:08:00 | true | 4-Hydroxypiperidine (75 mmol) and Boc-L-phenylalanine (38 mmol) were coupled according to Procedure A (0-25° C. reaction temperature, 144 hour reaction time) and the product used without further purification. Yield 12.2 g, 96%; HPLC (60/40) 3.45 minutes (97%). | CC(C)(C)OC(=O)N[C@@H](Cc1ccccc1)C(=O)N1CCC(O)CC1 | null | CC(C)(C)OC(=O)N[C@@H](Cc1ccccc1)C(=O)O | OC1CCNCC1 | null | [OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[C:8]([NH:15][C@H:16]([C:24](O)=[O:25])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]>>[C:11]([O:10][C:8](=[O:9])[NH:15][C@@H:16]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:24]([N:5]1[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]1)=[O:25])([CH3:14])([CH3:12])[CH3:13] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
545,554 | null | null | null | null | ord_dataset-d31180f42ced44719fd9e72685c798bf | 2002-01-01T00:05:00 | true | Under nitrogen, 27.9 mL of triethylamine was added to the concentrated solution of 2,3-dichloro-6-nitrobenzylalcohol (compound XI) prepared in the previous step. To this solution, 14.6 mL of thionyl chloride was added via an addition funnel over 15 minutes. Following addition, the solution is heated to 45-50° C. for 18 hours, then cooled to room temperature under nitrogen. Water and toluene are added to the reaction mixture and the mixture filtered. The filtrate is diluted with water, and the aqueous layer removed. The organic layer is washed with water (4×40 mL), and dried by azeotropic distillation. The solution is concentrated to give 1,2-dichloro-3-chloromethyl-4-nitrobenzene (compound (VIII), which could be used without further purification. | O=[N+]([O-])c1ccc(Cl)c(Cl)c1CCl | null | O=[N+]([O-])c1ccc(Cl)c(Cl)c1CO | O=S(Cl)Cl | null | C(N(CC)CC)C.[Cl:8][C:9]1[C:16]([Cl:17])=[CH:15][CH:14]=[C:13]([N+:18]([O-:20])=[O:19])[C:10]=1[CH2:11]O.S(Cl)([Cl:23])=O.O>C1(C)C=CC=CC=1>[Cl:8][C:9]1[C:16]([Cl:17])=[CH:15][CH:14]=[C:13]([N+:18]([O-:20])=[O:19])[C:10]=1[CH2:11][Cl:23] | null | Cc1ccccc1 | CCN(CC)CC | O | 47.5 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,763,296 | [Li+] | [OH-] | null | null | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | 2016-01-01T00:09:00 | true | 138 mg (0.33 mmol) of ethyl 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-cyclobutylpropanoate (racemate) were hydrolysed with lithium hydroxide according to General Method 6B. Yield: 104 mg (82% of theory) | COc1cn(C(CC2CCC2)C(=O)O)c(=O)cc1-c1cc(Cl)ccc1C#N | null | CCOC(=O)C(CC1CCC1)n1cc(OC)c(-c2cc(Cl)ccc2C#N)cc1=O | null | null | [Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:28]#[N:29])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH2:22][CH:23]3[CH2:26][CH2:25][CH2:24]3)[C:17]([O:19]CC)=[O:18])[C:10](=[O:27])[CH:9]=2)[CH:7]=1.[OH-].[Li+]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:28]#[N:29])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH2:22][CH:23]3[CH2:26][CH2:25][CH2:24]3)[C:17]([OH:19])=[O:18])[C:10](=[O:27])[CH:9]=2)[CH: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 |
353,028 | null | null | null | null | ord_dataset-127eb5fdd5b4402e92b51d0b55a5dcb5 | 1997-01-01T00:01:00 | true | A mixture of (S)-2-ethyl-4-(2-propyl)-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7-carboxylic acid (0.70 g) in thionyl chloride (15 ml) was stirred under reflux for 2 hours. Thionyl chloride was distilled off under reduced pressure to give (S)-2-ethyl-4-(2-propyl)-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7-carbonyl chloride (0.70 g). | CC[C@@H]1Oc2cc(C(=O)Cl)ccc2N(C(C)C)C1=O | null | CC[C@@H]1Oc2cc(C(=O)O)ccc2N(C(C)C)C1=O | O=S(Cl)Cl | null | [CH2:1]([C@H:3]1[C:8](=[O:9])[N:7]([CH:10]([CH3:12])[CH3:11])[C:6]2[CH:13]=[CH:14][C:15]([C:17]([OH:19])=O)=[CH:16][C:5]=2[O:4]1)[CH3:2].S(Cl)([Cl:22])=O>>[CH2:1]([C@H:3]1[C:8](=[O:9])[N:7]([CH:10]([CH3:12])[CH3:11])[C:6]2[CH:13]=[CH:14][C:15]([C:17]([Cl:22])=[O:19])=[CH:16][C:5]=2[O:4]1)[CH3:2] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,416,071 | O=C([O-])[O-] | [K+] | null | null | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | 2014-01-01T00:04:00 | true | 3-Cyclopentylphenol (40 mg, 0.25 mmol) and 2-chloro-oxazole-4-carboxylic acid [1-(3,5-difluoro-4-methanesulfonylamino-phenyl)-ethyl]-amide (40 mg, 0.11 mmol) was reacted using K2CO3 (50 mg, 0.36 mmol) as described above to give the title compound (40 mg, 75%) after purification by flash chromatography on silica gel (hexane: EtOAc=1:1). | CC(NC(=O)c1coc(Oc2cccc(C3CCCC3)c2)n1)c1cc(F)c(NS(C)(=O)=O)c(F)c1 | null | CC(NC(=O)c1coc(Cl)n1)c1cc(F)c(NS(C)(=O)=O)c(F)c1 | Oc1cccc(C2CCCC2)c1 | null | [CH:1]1([C:6]2[CH:7]=[C:8]([OH:12])[CH:9]=[CH:10][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[F:13][C:14]1[CH:15]=[C:16]([CH:26]([NH:28][C:29]([C:31]2[N:32]=[C:33](Cl)[O:34][CH:35]=2)=[O:30])[CH3:27])[CH:17]=[C:18]([F:25])[C:19]=1[NH:20][S:21]([CH3:24])(=[O:23])=[O:22].C([O-])([O-])=O.[K+].[K+]>>[F:25][C:18]1[CH:17]=[C:16]([CH:26]([NH:28][C:29]([C:31]2[N:32]=[C:33]([O:12][C:8]3[CH:9]=[CH:10][CH:11]=[C:6]([CH:1]4[CH2:2][CH2:3][CH2:4][CH2:5]4)[CH:7]=3)[O:34][CH:35]=2)=[O:30])[CH3:27])[CH:15]=[C:14]([F:13])[C:19]=1[NH:20][S:21]([CH3:24])(=[O:23])=[O:22] | null | null | null | null | null | null | 71.9 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
493,884 | [Zn] | null | null | null | ord_dataset-3f9174c7efcb4f31becbd3516cde9572 | 2001-01-01T00:02:00 | true | To a suspension of 2-methoxybenzaldehyde (622.4 mg, 4.57 mmol), 1,1-dimethylnitroethane (942.7 mg, 9.14 mmol) and zinc (896.3 mg, 13.7 mmol) in ethanol (15 ml) was added acetic acid (944.8 mg, 15.7 mmol) dropwise at 5° C. while stirring. The mixture was stirred at room temperature for one day. After the mixture was cooled to 5° C., zinc acetate was filtered off and the filtrate was concentrated and purified by silica gel chromatography (hexane/ethyl acetate=2/1). | COc1ccccc1C=[N+]([O-])C(C)(C)C | null | CC(C)(C)[N+](=O)[O-] | COc1ccccc1C=O | null | [CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=O.[CH3:11][C:12]([N+:15]([O-])=[O:16])([CH3:14])[CH3:13].C(O)(=O)C>C(O)C.[Zn]>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=[N+:15]([C:12]([CH3:14])([CH3:13])[CH3:11])[O-:16] | null | CC(=O)O | CCO | null | 5 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,295,697 | CC(=O)[O-] | Cl | [Na+] | null | ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c | 2013-01-01T00:05:00 | true | To a solution of 4-(4-(5-chloro-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidin-2-ylamino)-2,5-dimethylphenyl)cyclohexanone (15 mg, 0.033 mmol) in MeOH (0.5 mL) was added NaOAc (6 mg, 0.073 mmol) and NH2OH HCl (5 mg, 0.073 mmol). The resulting mixture was stirred at 70° C. for 2 h. and then cooled down to room temperature. The mixture was purified directly by preparative RP-HPLC to provide 4-(4-(5-chloro-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidin-2-ylamino)-2,5-dimethylphenyl)-cyclohexanone oxime; ESMS m/z 440.2 (M+H+). | Cc1cc(Nc2nc(Nc3cc(C)c(C4CCC(=NO)CC4)cc3C)ncc2Cl)n[nH]1 | null | Cc1cc(Nc2nc(Nc3cc(C)c(C4CCC(=O)CC4)cc3C)ncc2Cl)n[nH]1 | NO | null | [Cl:1][C:2]1[C:3]([NH:24][C:25]2[CH:29]=[C:28]([CH3:30])[NH:27][N:26]=2)=[N:4][C:5]([NH:8][C:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH:16]3[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]3)=[C:11]([CH3:23])[CH:10]=2)=[N:6][CH:7]=1.CC([O-])=O.[Na+].[NH2:36][OH:37].Cl>CO>[Cl:1][C:2]1[C:3]([NH:24][C:25]2[CH:29]=[C:28]([CH3:30])[NH:27][N:26]=2)=[N:4][C:5]([NH:8][C:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH:16]3[CH2:21][CH2:20][C:19](=[N:36][OH:37])[CH2:18][CH2:17]3)=[C:11]([CH3:23])[CH:10]=2)=[N:6][CH:7]=1 | 2 | CO | null | null | 70 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
946,430 | null | null | null | null | ord_dataset-ed680843f6d14f5c9901869b2a06b4a4 | 2010-01-01T00:03:00 | true | By reacting (S)-N-{3-[4-(4-oxo-3,3-dimethyl-piperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide (2.3 mmol) and methyl lithium (2.3 mmol) in tetrahydrofuran (20 ml) followed by silica gel chromatographic separation of diastereomer the compound was obtained in 69% yield. M.P. 114-116° C. and MS (M+1)=394 (MH+, 100%) for M.F.=C20H28FN3O4. | CC(=O)NC[C@H]1CN(c2ccc(N3CCC(C)(O)C(C)(C)C3)c(F)c2)C(=O)O1 | null | [Li]C | CC(=O)NC[C@H]1CN(c2ccc(N3CCC(=O)C(C)(C)C3)c(F)c2)C(=O)O1 | null | [O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][NH:20][C:21](=[O:23])[CH3:22])[O:16][C:15]3=[O:24])=[CH:10][C:9]=2[F:25])[CH2:4][C:3]1([CH3:27])[CH3:26].[CH3:28][Li]>O1CCCC1>[CH3:26][C:3]1([CH3:27])[C:2]([CH3:28])([OH:1])[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][NH:20][C:21](=[O:23])[CH3:22])[O:16][C:15]3=[O:24])=[CH:10][C:9]=2[F:25])[CH2:4]1 | null | C1CCOC1 | null | null | null | null | 69 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,558,458 | CC(C)(C)[O-] | [K+] | null | null | ord_dataset-4e54080057a44c3887653391e24c90b6 | 2015-01-01T00:03:00 | true | To a round-bottom flask at room temperature was added (R)-methyl 1-(4-bromophenyl)-2,2-diphenylcyclopropanecarboxylate (17.9 mmol, 7.3 g, 1.0 equiv) in dry DMSO (35 mL). t-BuOK (39.6 mmol, 4.4 g, 2.2 equiv) was added in several portions over 30 minutes under argon. The reaction was monitored by TLC technique until the starting material was consumed completely. The reaction mixture was cooled with ice bath and acidified by saturated ammonium chloride aqueous (15 mL), followed by a slow addition of 1 N HCl (50 mL) with vigorous stirring until the pH value reached 3-4. Sticky solid precipitate was collected by filtration, washed with water (3×5 mL), dissolved in ethyl acetate (150 mL), washed with brine (3×10 mL), dried over anhydrous MgSO4, and concentrated in vacuo. The crude material was purified using flash column chromatography eluting with a 4:1 mixture of hexanes/ethyl acetate to provide the desired product as a white solid (4.9 g, 69% yield). Recrystallization in pentane/ethyl acetate (50/1) provided the enantioenriched product as a white solid (4.46 g, 64% yield, 99% ee). (S)-1-(4-bromophenyl)-2,2-diphenylcyclopropanecarboxylic acid was prepared by the same procedure, | O=C(O)[C@@]1(c2ccc(Br)cc2)CC1(c1ccccc1)c1ccccc1 | null | COC(=O)[C@@]1(c2ccc(Br)cc2)CC1(c1ccccc1)c1ccccc1 | null | null | [Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([C:23]([O:25]C)=[O:24])[CH2:10][C:9]2([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.CC([O-])(C)C.[K+]>CS(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@:8]2([C:23]([OH:25])=[O:24])[CH2:10][C:9]2([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:6][CH:7]=1 | null | CS(C)=O | null | null | null | null | 69.6 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,223,247 | O=C([O-])[O-] | [Cs+] | null | null | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | 2012-01-01T00:11:00 | true | A suspension of 1-t-butyl 2-methyl (2S,4S)-4-{[(4-bromophenyl)sulfonyl]oxy}pyrrolidine-1,2-dicarboxylate (25.0 g, 53.8 mmol), 6-bromo-2-ethoxy-7-methoxyquinolin-4-ol (16.1 g, 53.8 mmol) and Cs2CO3 (52.6 g, 162 mmol) in NMP (300 mL) was stirred at 75° C., under N2, for 2 hours. At 22° C., the reaction was diluted with water (500 mL) and extracted with EtOAc (3×500 mL). The combined EtOAc layers were washed with water (3×100 mL), brine (100 mL), dried over Na2SO4, filtered and concentrated. The residue was chromatographed on silica gel 60, eluting with 0 to 50% EtOAc in hexane, to give the title product. 1H NMR (400 MHz, CDCl3) δ 8.13 (s, 1H); 7.16 (s, 1H); 6.02 (s, 1H); 5.05 (m, 1H); 4.49 (m, 3H); 4.00 (s, 3H); 3.91 (m, 2H); 3.78 (s, 3H); 2.67 (m, 1H); 2.37 (m, 1H); 1.47 (s, 3H); 1.44 (s, 9H) ppm. LRMS (ESI) m/z 525.0 [(M+H)+; calcd for C23H30BrN2O7: 298.0]. | CCOc1cc(O[C@@H]2C[C@@H](C(=O)OC)N(C(=O)OC(C)(C)C)C2)c2cc(Br)c(OC)cc2n1 | null | COC(=O)[C@@H]1C[C@H](OS(=O)(=O)c2ccc(Br)cc2)CN1C(=O)OC(C)(C)C | CCOc1cc(O)c2cc(Br)c(OC)cc2n1 | null | BrC1C=CC(S([O:11][C@@H:12]2[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:14]([C:24]([O:26][CH3:27])=[O:25])[CH2:13]2)(=O)=O)=CC=1.[Br:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][C:38]=1[O:39][CH3:40])[N:35]=[C:34]([O:41][CH2:42][CH3:43])[CH:33]=[C:32]2O.C([O-])([O-])=O.[Cs+].[Cs+]>CN1C(=O)CCC1.O>[Br:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][C:38]=1[O:39][CH3:40])[N:35]=[C:34]([O:41][CH2:42][CH3:43])[CH:33]=[C:32]2[O:11][C@H:12]1[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[C@H:14]([C:24]([O:26][CH3:27])=[O:25])[CH2:13]1 | 2 | O | CN1CCCC1=O | null | 75 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
131,005 | null | null | null | null | ord_dataset-7724d657b6fc42848b62ca7c93d84bed | 1985-01-01T00:06:00 | true | By following serially the procedure of step (a) of example 5 and the procedure of example 6 and selecting 5,6-dimethoxy-1,7,8,12b-tetrahydrobenzo[6,7]cyclohepta[1,2,3-de]isoquinoline as the starting material of formula II, methyl iodide as the organohalide and phenylmethyl magnesium chloride as the Grignard reagent, (3,12b-trans)-5,6-dimethoxy-2-methyl-3-(phenylmethyl)-1,2,3,7,8,12b-hexahydrobenzo[6,7]cyclohepta[1,2,3-de]isoquinoline, mp 154°-156° C., NMR (CDCl3) δ2.4 (s, 3H), 3.77 & 3.85 (2s, 6H), 6.5 (s, 1H), 7.2 (m, 9H), was obtained via 5,6-dimethoxy-2-methyl-1,7,8,12b-tetrahydrobenzo[6,7]cyclohepta[1,2,3-de]isoquinolinium iodide, mp 195°-210° C. (dec), NMR (DMSO-d6) δ 3.83 (s, 3H), 3.88 (s, 3H), 3.97 (s, 3H), 4.42 (m, 2H), 5.18 (m, 1H), 7.10 (m, 4H), 7.38 (s, 1H), 9.17 (s, 1H). | COc1cc2c3c(c1OC)CCc1ccccc1C3C[N+](C)=C2 | [I-] | COc1cc2c3c(c1OC)CCc1ccccc1C3CN=C2 | Cl[Mg]Cc1ccccc1 | CI | [CH3:1][O:2][C:3]1[C:4]([O:21][CH3:22])=[C:5]2[CH2:16][CH2:15][C:14]3[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=3[CH:7]3[CH2:8][N:9]=[CH:10][C:11]([CH:12]=1)=[C:6]23.C[I:24].[C:25]1(C[Mg]Cl)C=CC=CC=1>>[I-:24].[CH3:1][O:2][C:3]1[C:4]([O:21][CH3:22])=[C:5]2[CH2:16][CH2:15][C:14]3[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=3[CH:7]3[CH2:8][N+:9]([CH3:25])=[CH:10][C:11]([CH:12]=1)=[C:6]23 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
143,109 | null | null | null | null | ord_dataset-1895fe091c3f47afa1ee96a41a250de4 | 1986-01-01T00:05:00 | true | React allyl-5-hydroxymethylimidazol-1-yl acetate with excess thionyl chloride in CH2Cl2 at ice bath temperatures for about 8 hours to form the title compound. | C=CCc1ncc(CCl)n1OC(C)=O | Cl | O=S(Cl)Cl | C=CCc1ncc(CO)n1OC(C)=O | null | [C:1]([O:4][N:5]1[C:9]([CH2:10]O)=[CH:8][N:7]=[C:6]1[CH2:12][CH:13]=[CH2:14])(=[O:3])[CH3:2].S(Cl)([Cl:17])=O>C(Cl)Cl>[ClH:17].[C:1]([O:4][N:5]1[C:9]([CH2:10][Cl:17])=[CH:8][N:7]=[C:6]1[CH2:12][CH:13]=[CH2:14])(=[O:3])[CH3:2] | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,504,092 | O=C([O-])[O-] | [K+] | null | null | ord_dataset-1a1aa5d1c3224edca0aec6e3398da985 | 2014-01-01T00:11:00 | true | To a stirred solution of 3-chloropropyl-1,3-dioxolane (0.2 g, 1.35 mmol) in dimethyl formamide (14 mL), was added 4-((3-(azido(phenyl)methyl)phenoxy)-methyl)benzoic acid (Example 51 Step 3) (0.5 g, 1.39 mmol) and potassium carbonate (0.38 g, 2.78 mmol). The reaction was allowed to stir at 80° C. for 16 hours. The reaction mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate (×3). The organic extracts were washed with brine, dried (sodium sulphate), filtered, and concentrated under reduced pressure. The crude material was purified by silica gel chromatography eluting with 0-100% ethyl acetate in iso-hexane to afford the title compound (0.63 g, 96%). | [N-]=[N+]=NC(c1ccccc1)c1cccc(OCc2ccc(C(=O)OCCCC3OCCO3)cc2)c1 | null | ClCCCC1OCCO1 | [N-]=[N+]=NC(c1ccccc1)c1cccc(OCc2ccc(C(=O)O)cc2)c1 | null | Cl[CH2:2][CH2:3][CH2:4][CH:5]1[O:9][CH2:8][CH2:7][O:6]1.[N:10]([CH:13]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:14]1[CH:15]=[C:16]([CH:28]=[CH:29][CH:30]=1)[O:17][CH2:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=1)=[N+:11]=[N-:12].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[N:10]([CH:13]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:14]1[CH:15]=[C:16]([CH:28]=[CH:29][CH:30]=1)[O:17][CH2:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([O:25][CH2:2][CH2:3][CH2:4][CH:5]2[O:9][CH2:8][CH2:7][O:6]2)=[O:24])=[CH:21][CH:20]=1)=[N+:11]=[N-:12] | 16 | O | CN(C)C=O | null | 80 | null | 98.6 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,180,828 | Cl | null | null | null | ord_dataset-0f9d2dbe929a45c3892ae75e81e99443 | 2012-01-01T00:06:00 | true | To a solution of tert-butyl(1S)-2,3-dihydro-1H-inden-1-yl(methyl)carbamate (1.84 g, 7.44 mmol) in MeOH (50.0 mL) under an atmosphere of nitrogen was added hydrochloric acid (6.00 mL, 72.4 mmol) and the mixture was stirred overnight. The reaction was concentrated in vacuo to afford the title compound as a white solid without further purification (1.35 g, 99%). LC/MS: Rt=0.85 min, ES+ 148 (AA standard). | CN[C@H]1CCc2ccccc21 | null | CN(C(=O)OC(C)(C)C)[C@H]1CCc2ccccc21 | null | null | [C@@H:1]1([N:10](C)[C:11](=O)OC(C)(C)C)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[ClH:19]>CO>[ClH:19].[CH3:11][NH:10][C@@H:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1 | 8 | CO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,126,170 | null | null | null | null | ord_dataset-285df12e34cd46e993e3c8ebc3a8962a | 2012-01-01T00:01:00 | true | The title compound is prepared in analogous manner as described for example 47a from 6-bromo-1,1-dimethyl-1,3-dihydro-isobenzofuran to yield a light yellow oil: TLC (hexane-EtOAc 1:1) Rf=0.50; HPLC RtA=1.43 min; 1H NMR (400 MHz, CDCl3): δ10.02 (s, 1H), 7.78 (d, 1H), 7.65 (s, 1H), 7.36 (d, 1H), 5.11 (s, 2H), 1.53 (s, 9H). | CC1(C)OCc2ccc(C=O)cc21 | null | CCOC(C)=O | CC1(C)OCc2ccc(Br)cc21 | null | Br[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][O:7][C:8]2([CH3:12])[CH3:11])=[CH:4][CH:3]=1.CCCCCC.C[CH2:20][O:21]C(C)=O>>[CH3:11][C:8]1([CH3:12])[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([CH:20]=[O:21])[CH:10]=2)[CH2:6][O:7]1 | null | CCCCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
761,231 | CN(C)c1ccncc1 | null | null | null | ord_dataset-2e58cb8db2bf482bbea23283b7e04488 | 2007-01-01T00:03:00 | true | 2-Thiophenecarbonylchloride (2.04 g, 1.49 mL) was added to a solution of tert-butyl-1-piperazinecarboxylate (2.5 g, 13.4 mmol) and DMAP (20 mg) in pyridine (15 mL) at 0° C. under N2 atmosphere and stirred at room temperature for overnight. The mixture was poured into ice water, the precipitate was filtered, washed several times with water, and dried to yield white solids (3.5 g, 88%). Mp 76° C. 1H NMR (DMSO-d6): δ 1.42 (s, 12H), 3.40 (m, 4H), 3.61 (m, 4H), 7.12 (m, 1H), 7.43 (d, J=4.1 Hz, 1H), 7.77 (d, J=4.8 Hz, 1H). EIMS m/z 297 (M+1), 319 (M+23). Anal. (C14H20N2O3S) C, H, N. | CC(C)(C)OC(=O)N1CCN(C(=O)c2cccs2)CC1 | null | O=C(Cl)c1cccs1 | CC(C)(C)OC(=O)N1CCNCC1 | null | [S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](Cl)=[O:7].[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][N:19]([C:6]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)=[O:7])[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:10])[CH3:11] | 8 | c1ccncc1 | null | null | 25 | null | 88.1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
978,656 | null | null | null | null | ord_dataset-f886e51ba1484c76a94bce1482f1eab9 | 2010-01-01T00:07:00 | true | A mixture of N-cyclopropyl-4-methyl-3-(1-(piperidin-4-yl)phthalazin-6-yl)benzamide N-cyclopropyl-4-methyl-3-(1-(piperidin-4-yl)phthalazin-6-yl)benzamide (29 μmol) in 2 mL ethanol was stirred at RT and treated with 2-trifluoromethylamine diacetate (142 μmol). The mixture was stirred at RT for 4 h, then purified directly by silica gel chromatography, eluting with 5% 2 M ammonia methanol/dichloromethane to give the title compound. | CC(=O)N1CCC(c2nncc3cc(-c4cc(C(=O)NC5CC5)ccc4C)ccc23)CC1 | null | Cc1ccc(C(=O)NC2CC2)cc1-c1ccc2c(C3CCNCC3)nncc2c1 | null | null | [CH:1]1([NH:4][C:5](=[O:29])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[C:19]([CH:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)=[N:18][N:17]=[CH:16]4)[CH:7]=2)[CH2:3][CH2:2]1.C1(N[C:34](=[O:58])[C:35]2C=CC(C)=C(C3C=C4C(=CC=3)C(C3CCNCC3)=NN=C4)C=2)CC1>C(O)C>[C:34]([N:26]1[CH2:27][CH2:28][CH:23]([C:19]2[C:20]3[C:15](=[CH:14][C:13]([C:8]4[CH:7]=[C:6]([CH:11]=[CH:10][C:9]=4[CH3:12])[C:5]([NH:4][CH:1]4[CH2:2][CH2:3]4)=[O:29])=[CH:22][CH:21]=3)[CH:16]=[N:17][N:18]=2)[CH2:24][CH2:25]1)(=[O:58])[CH3:35] | null | CCO | null | null | 25 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
191,445 | Cl | [Na+] | [OH-] | null | ord_dataset-d1bd8c96676b4d21aad27b173c6b4eff | 1989-01-01T00:06:00 | true | A mixture of 2.2 g of 1-(4-acetylaminophenyl)-3-allyl-3-azabicyclo[3.1.0]hexane-2,4-dione, 8 ml of water and 8 ml of concentrated hydrochloric acid is stirred for 3 hours at 100° C. The mixture is diluted with a small amount of water, cooled in an ice-water bath, made alkaline with 30% sodium hydroxide solution, and extracted twice with ethyl acetate. The organic phases are washed repeatedly with water and once with a concentrated aqueous solution of sodium chloride, dried over magnesium sulfate and filtered. The filtrate is concentrated and the residue is crystallised from ethyl acetate/petroleum ether. The title compound is obtained in the form of pale beige-coloured crystals with m.p. 104°-106° C. and with Rf=0.57 on thin-layer silica gel plates in the system methylene chloride/methanol (10:1). | C=CCN1C(=O)C2CC2(c2ccc(N)cc2)C1=O | null | C=CCN1C(=O)C2CC2(c2ccc(NC(C)=O)cc2)C1=O | null | null | C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]23[CH2:16][CH:15]2[C:14](=[O:17])[N:13]([CH2:18][CH:19]=[CH2:20])[C:12]3=[O:21])=[CH:7][CH:6]=1)(=O)C.Cl.[OH-].[Na+]>O>[NH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]23[CH2:16][CH:15]2[C:14](=[O:17])[N:13]([CH2:18][CH:19]=[CH2:20])[C:12]3=[O:21])=[CH:9][CH:10]=1 | 3 | O | null | null | 100 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
467,374 | O=C([O-])[O-] | [Cs+] | null | null | ord_dataset-8cd3720738054d76b936f66e14d8cba6 | 2000-01-01T00:06:00 | true | 4-cyano-3-hydroxybenzoic acid methyl ester, Example 34, Step 3 (300 mg, 1.7 mmol) was dissolved in DMF (8.5 ml) and treated with benzyl bromide (200 μl, 1.7 mmol). Cs2CO3 (610 mg, 1.87 mmol) was then added and the reaction mixture stirred at room temp. for 6 hours. The mixture was filtered and washed with DMF (3×10 mL). The solvent was removed in vacuo and the residue was purified by flash chromatography (15% EtOAc/Hexane) to yield the desired product. | COC(=O)c1ccc(C#N)c(OCc2ccccc2)c1 | null | BrCc1ccccc1 | COC(=O)c1ccc(C#N)c(O)c1 | null | [CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[C:6]([OH:12])[CH:5]=1.[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[C:6]([O:12][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:5]=1 | 6 | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
759,321 | Cl | null | null | null | ord_dataset-2e58cb8db2bf482bbea23283b7e04488 | 2007-01-01T00:03:00 | true | A mixture of N-(1-benzyl-4-methyl-4-piperidinyl)acetamide obtained in Example 10-2 (3.45 g) and conc. HCl (41 mL) was heated under reflux with stirring for 72 hrs. After cooling, the mixture was quenched by adding 3N potassium hydroxide solution, and the resulting solution (pH11) was extracted with chloroform. The organic layer was washed with brine, dried over MgSO4, and concentrated to give the title compound as a pale brown oil (2.86 g). | CC1(N)CCN(Cc2ccccc2)CC1 | null | CC(=O)NC1(C)CCN(Cc2ccccc2)CC1 | null | null | [CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([NH:15]C(=O)C)([CH3:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH3:14])([NH2:15])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1 | 72 | null | null | null | null | null | 100 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
498,100 | Cl | null | null | null | ord_dataset-18e9ed24dbd44e98b33bdc22aa7580a8 | 2001-01-01T00:04:00 | true | A stirred mixture of 2-7 (0.45 g, 1.4 mmol) and 6N HCl (10 mL) was heated at 50° C. for 1 h, followed by concentration to give 2-8 as a yellow oil. | O=C(O)CN1CCC(CCc2ccc3c(n2)NCCC3)C1=O | null | CCOC(=O)CN1CCC(CCc2ccc3c(n2)NCCC3)C1=O | null | null | [O:1]=[C:2]1[CH:6]([CH2:7][CH2:8][C:9]2[CH:18]=[CH:17][C:16]3[CH2:15][CH2:14][CH2:13][NH:12][C:11]=3[N:10]=2)[CH2:5][CH2:4][N:3]1[CH2:19][C:20]([O:22]CC)=[O:21].[ClH:25]>>[ClH:25].[O:1]=[C:2]1[CH:6]([CH2:7][CH2:8][C:9]2[CH:18]=[CH:17][C:16]3[CH2:15][CH2:14][CH2:13][NH:12][C:11]=3[N:10]=2)[CH2:5][CH2:4][N:3]1[CH2:19][C:20]([OH:22])=[O:21] | null | null | null | 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 | null |
1,583,108 | null | null | null | null | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | 2015-01-01T00:05:00 | true | Obtained by starting from (R)—((S)-5′-(tert-butyldimethylsilyloxy)-4′-iodo-2′-isopropyl-6′,8′-dihydro-5′H-spiro[cyclobutane-1,7′-quinoline]-3′-yl)(4-(trifluoromethyl)phenyl)methanol and 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. | CC(C)c1nc2c(c(C3=CCOCC3)c1[C@H](O)c1ccc(C(F)(F)F)cc1)[C@@H](O[Si](C)(C)C(C)(C)C)CC1(CCC1)C2 | null | CC1(C)OB(C2=CCOCC2)OC1(C)C | CC(C)c1nc2c(c(I)c1[C@H](O)c1ccc(C(F)(F)F)cc1)[C@@H](O[Si](C)(C)C(C)(C)C)CC1(CCC1)C2 | null | [Si:1]([O:8][C@H:9]1[CH2:18][C:17]2([CH2:21][CH2:20][CH2:19]2)[CH2:16][C:15]2[N:14]=[C:13]([CH:22]([CH3:24])[CH3:23])[C:12]([C@@H:25]([C:27]3[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=3)[OH:26])=[C:11](I)[C:10]1=2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[O:38]1[CH2:43][CH:42]=[C:41](B2OC(C)(C)C(C)(C)O2)[CH2:40][CH2:39]1>>[Si:1]([O:8][C@H:9]1[CH2:18][C:17]2([CH2:21][CH2:20][CH2:19]2)[CH2:16][C:15]2[N:14]=[C:13]([CH:22]([CH3:24])[CH3:23])[C:12]([C@@H:25]([C:27]3[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=3)[OH:26])=[C:11]([C:41]3[CH2:42][CH2:43][O:38][CH2:39][CH:40]=3)[C:10]1=2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,617,779 | Cl | O=C[O-] | [Na+] | null | ord_dataset-35c51552812941cda45194a013d34bb9 | 2015-01-01T00:08:00 | true | 0.91 g (2.30 mmol) of 2-(2,6-diethyl-4-methylphenyl)-5-formyl-3-oxooctahydropentalen-1-yl 2,2-dimethylpropanoate (Example I-b-2), 0.78 g (11.48 mmol) of sodium formate and 0.80 g (11.48 mmol) of hydroxylamine hydrochloride in 30 ml of formic acid are heated at reflux for 72 h. 50 ml of water are then added, and the mixture is stirred at room temperature for 1 h, taken up in ethyl acetate, washed twice with water, dried (magnesium sulphate) and concentrated using a rotary evaporator. The residue is chromatographed on silica gel (mobile phase ethyl acetate/hexane 1:6). This gives 0.31 g (44%) of the desired compound as a colourless oil. | CCc1cc(C)cc(CC)c1C1C(=O)C2CC(C#N)CC2C1=O | null | NO | CCc1cc(C)cc(CC)c1C1C(=O)C2CC(C=O)CC2C1OC(=O)C(C)(C)C | null | CC(C)(C)C([O:5][CH:6]1[CH:13]2[CH:9]([CH2:10][CH:11]([CH:14]=O)[CH2:12]2)[C:8](=[O:16])[CH:7]1[C:17]1[C:22]([CH2:23][CH3:24])=[CH:21][C:20]([CH3:25])=[CH:19][C:18]=1[CH2:26][CH3:27])=O.C([O-])=O.[Na+].Cl.[NH2:35]O.O>C(O)=O.C(OCC)(=O)C>[CH2:26]([C:18]1[CH:19]=[C:20]([CH3:25])[CH:21]=[C:22]([CH2:23][CH3:24])[C:17]=1[CH:7]1[C:6](=[O:5])[CH:13]2[CH:9]([CH2:10][CH:11]([C:14]#[N:35])[CH2:12]2)[C:8]1=[O:16])[CH3:27] | 1 | O=CO | CCOC(C)=O | O | 25 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
376,438 | [Al+3] | [Cl-] | null | null | ord_dataset-846d411edee44814931e062174d7ef12 | 1997-01-01T00:09:00 | true | In a 1-liter three-necked flask equipped with a stirring device, a thermometer and a nitrogen substituting device, 33.3 g of aluminum chloride and 200 milliliters of 1,2-dichloroethane were mixed and then 40.8 g of paranitrobenzoyl chloride was introduced with ice cooling to be dissolved. Then, a solution of 23.6 g of 1,6-diphenylhexane in 50 milliliters of 1,2-dichloroethane was added dropwise for 30 minutes. After the end of the dropwise adding, the solution was stirred for 3 hours with warming back to the room temperature. After the end of reaction was confirmed by a liquid chromatography, the reaction solution was poured in 500 milliliters of ice water, and then extracted with 1.8 liters of chloroform. The solution was washed with an aqueous solution of sodium hydrogencarbonate and water, and then dried with magnesium sulfate. Chloroform was removed off by a rotary evaporator, and then 56.0 g of 1,6-bis(4-(4-nitrobenzoyl)phenyl)hexane was obtained as crystals by recrystallizing from a mixed solvent of chloroform and ethyl acetate. | O=C(c1ccc(CCCCCCc2ccc(C(=O)c3ccc([N+](=O)[O-])cc3)cc2)cc1)c1ccc([N+](=O)[O-])cc1 | null | c1ccc(CCCCCCc2ccccc2)cc1 | O=C(Cl)c1ccc([N+](=O)[O-])cc1 | null | [Cl-].[Al+3].[Cl-].[Cl-].[N+:5]([C:8]1[CH:16]=[CH:15][C:11]([C:12](Cl)=[O:13])=[CH:10][CH:9]=1)([O-:7])=[O:6].[C:17]1([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>ClCCCl>[N+:5]([C:8]1[CH:16]=[CH:15][C:11]([C:12]([C:20]2[CH:21]=[CH:22][C:17]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]3[CH:30]=[CH:31][C:32]([C:12](=[O:13])[C:11]4[CH:10]=[CH:9][C:8]([N+:5]([O-:7])=[O:6])=[CH:16][CH:15]=4)=[CH:33][CH:34]=3)=[CH:18][CH:19]=2)=[O:13])=[CH:10][CH:9]=1)([O-:7])=[O:6] | 3 | ClCCCl | null | null | 25 | 105.4 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,553,074 | [Cl-] | [Li+] | null | null | ord_dataset-cac8df8aff894288876df4e093c9877f | 2015-01-01T00:02:00 | true | A 0° C. mixture of trimethyl phosphonoacetate (0.209 mL, 1.45 mmol), DBU (0.218 mL, 1.45 mmol) and LiCl (0.061 g, 1.45 mmol) in MeCN (5 mL) was stirred for 30 min under N2, after which 3-(1-(3-fluoro-5-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)propanal (0.35 g, 0.966 mmol) in MeCN (5 mL) was added. The reaction was stirred for 2 h at rt, then was concentrated in vacuo. The residue was diluted with Et2O, and then washed successively with 1N aq. HCl, sat. aq. NaHCO3, and brine, dried (MgSO4), and concentrated in vacuo. The residual crude oil was chromatographed (SiO2; gradient from 0% to 50% EtOAc/hexane over 20 min) to give the title compound (0.30 g, 0.717 mmol, 74.2% yield) as a white solid. 1H NMR (CDCl3) δ: 6.97 (dt, J=15.6, 6.8 Hz, 1H), 6.87 (t, J=1.8 Hz, 1H), 6.75 (ddd, J=10.1, 2.3, 1.4 Hz, 1H), 6.68 (dt, J=10.5, 2.3 Hz, 1H), 5.85 (dt, J=15.6, 1.6 Hz, 1H), 5.40 (t, J=3.2 Hz, 1H), 3.89 (ddd, J=11.3, 10.0, 3.1 Hz, 1H), 3.84-3.81 (m, 2H), 3.75 (s, 3H), 3.62 (dtd, J=11.4, 4.1, 1.4 Hz, 1H), 2.22-2.14 (m, 2H), 2.05-1.98 (m, 4H), 1.88-1.82 (m, 2H), 1.75-1.59 (m, 8H), 1.36-1.30 (m, 2H); 19F NMR (CDCl3) δ: −112.1. | COC(=O)/C=C/CCC12CCC(c3cc(F)cc(OC4CCCCO4)c3)(CC1)OC2 | null | O=CCCC12CCC(c3cc(F)cc(OC4CCCCO4)c3)(CC1)OC2 | COC(=O)CP(=O)(OC)OC | null | [CH3:1][O:2][C:3]([CH2:5]P(OC)(OC)=O)=[O:4].C1CCN2C(=NCCC2)CC1.[Li+].[Cl-].[F:25][C:26]1[CH:27]=[C:28]([C:39]23[CH2:46][CH2:45][C:42]([CH2:47][CH2:48][CH:49]=O)([CH2:43][CH2:44]2)[CH2:41][O:40]3)[CH:29]=[C:30]([O:32][CH:33]2[CH2:38][CH2:37][CH2:36][CH2:35][O:34]2)[CH:31]=1>CC#N>[F:25][C:26]1[CH:27]=[C:28]([C:39]23[CH2:44][CH2:43][C:42]([CH2:47][CH2:48]/[CH:49]=[CH:5]/[C:3]([O:2][CH3:1])=[O:4])([CH2:45][CH2:46]2)[CH2:41][O:40]3)[CH:29]=[C:30]([O:32][CH:33]2[CH2:38][CH2:37][CH2:36][CH2:35][O:34]2)[CH:31]=1 | 0.5 | C1CCC2=NCCCN2CC1 | CC#N | null | null | 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 |
645,748 | null | null | null | null | ord_dataset-c975a50a7600448fabd558f4a94a3e29 | 2004-01-01T00:08:00 | true | 5-Amino-1,2-dihydropyrazol-3-one (0.15 g, 1.5 mmol), 3-bromo-4-fluorobenzaldehyde (0.3 g, 1.5 mmol), and 1,3-cyclohexanedione (0.17 g, 1.5 mmol) were processed as described in Example 2 to provide 0.14 g of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 1.85 (m, 2H), 2.18 (m, 2H), 2.55 (m, 2H), 4.94 (s,1H), 7.12 (m, 1H), 718 (t, 1H), 7.4 (dd, 1H), 9.75 (s, 1H), 10.35 (bs, 1H), 11.33 (bs, 1H); MS (ESI−) m/z 376 (M−H)−; Anal. Calcd for C16H13N3BrFO2: C, 50.79; H, 3.44; N, 11.11. Found: C, 50.45; H, 3.42; N, 11.33. | O=C1CCCC2=C1C(c1ccc(F)c(Br)c1)c1c([nH][nH]c1=O)N2 | null | O=Cc1ccc(F)c(Br)c1 | Nc1cc(=O)[nH][nH]1 | O=C1CCCC(=O)C1 | [NH2:1][C:2]1[NH:6][NH:5][C:4](=[O:7])[CH:3]=1.[Br:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[F:17])[CH:12]=O.[C:18]1(=O)[CH2:23][CH2:22][CH2:21][C:20](=[O:24])[CH2:19]1>>[Br:8][C:9]1[CH:10]=[C:11]([CH:12]2[C:19]3[C:20](=[O:24])[CH2:21][CH2:22][CH2:23][C:18]=3[NH:1][C:2]3[NH:6][NH:5][C:4](=[O:7])[C:3]2=3)[CH:14]=[CH:15][C:16]=1[F:17] | null | null | null | null | null | 24.7 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,097,203 | null | null | null | null | ord_dataset-af85e6f81c2d49f08086afd6d9e6959c | 2011-01-01T00:10:00 | true | To a stirred solution of 1-(2-amino-pyridin-4-ylmethyl)-1H-benzo[d][1,3]oxazine-2,4-dione (600 mg, see preparation 7b) in pyridine (7 ml) was added isocyanato-acetic acid ethyl ester (0.4 ml). The reaction mixture was stirred at room temperature for 3 hours, and the solvent was evaporated under reduced pressure. The residue was dissolved in EtOAc and washed with water and brine. The organic layer was dried (MgSO4) and evaporated under reduced pressure. The resulting oil was treated with EtOAc (3 ml) and gave a precipitate that was isolated by filtration and dried in vacuo, affording {3-[4-(2,4-Dioxo-4H-benzo[d][1,3]oxazin-1-ylmethyl)-pyridin-2-yl]-ureido}-acetic acid ethyl ester (0.53 g). Step 2: This anhydride intermediate was converted into the title compound by reaction with O-(4-cyanobenzyl)hydroxylamine hydrochloride (see preparation 10), using general procedure 1A. 13C-NMR (DMSO-d6) δ 170.3, 167.4, 154.8, 153.5, 151.4, 148.5, 146.7, 141.8, 132.7, 132.2, 129.1, 128.0, 118.6, 115.4, 114.8, 112.9, 111.5, 110.7, 109.3, 76.0, 60.3, 45.2, 41.2, 14.0. | CCOC(=O)CNC(=O)Nc1cc(Cn2c(=O)oc(=O)c3ccccc32)ccn1 | null | CCOC(=O)CN=C=O | Nc1cc(Cn2c(=O)oc(=O)c3ccccc32)ccn1 | null | [NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][N:9]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[C:12](=[O:19])[O:11][C:10]2=[O:20])[CH:5]=[CH:4][N:3]=1.[CH2:21]([O:23][C:24](=[O:29])[CH2:25][N:26]=[C:27]=[O:28])[CH3:22]>N1C=CC=CC=1>[CH2:21]([O:23][C:24](=[O:29])[CH2:25][NH:26][C:27]([NH:1][C:2]1[CH:7]=[C:6]([CH2:8][N:9]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[C:12](=[O:19])[O:11][C:10]2=[O:20])[CH:5]=[CH:4][N:3]=1)=[O:28])[CH3:22] | 3 | c1ccncc1 | 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 |
682,145 | [Na+] | [OH-] | null | null | ord_dataset-3947f3e1be17462c8f7c7e6ea6e57d0a | 2005-01-01T00:08:00 | true | In methanol (25 ml) and THF (25 ml) was dissolved methyl 7-[4-(3-ethoxypropoxy)phenyl]-1-formyl-2,3-dihydro-1H-1-benzazepine-4-carboxylate (0.31 g). To the solution was added 1N sodium hydroxide solution (8 ml), and the mixture was stirred at 50° C. for 1.5 hours and concentrated. To the residue was added water, and the mixture was neutralized with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried with anhydrous magnesium sulfate, and the solvent was evaporated to give 7-[4-(3-ethoxypropoxy)phenyl]-1-formyl-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid (0.3 g) as colorless crystals. | CCOCCCOc1ccc(-c2ccc3c(c2)C=C(C(=O)O)CCN3C=O)cc1 | null | CCOCCCOc1ccc(-c2ccc3c(c2)C=C(C(=O)OC)CCN3C=O)cc1 | null | null | [CH2:1]([O:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[CH:16][C:17]3[N:23]([CH:24]=[O:25])[CH2:22][CH2:21][C:20]([C:26]([O:28]C)=[O:27])=[CH:19][C:18]=3[CH:30]=2)=[CH:10][CH:9]=1)[CH3:2].[OH-].[Na+]>CO.C1COCC1>[CH2:1]([O:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:15]=[CH:16][C:17]3[N:23]([CH:24]=[O:25])[CH2:22][CH2:21][C:20]([C:26]([OH:28])=[O:27])=[CH:19][C:18]=3[CH:30]=2)=[CH:12][CH:13]=1)[CH3:2] | 1.5 | CO | C1CCOC1 | null | 50 | null | 100.2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
722,808 | O=C([O-])[O-] | [K+] | null | null | ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | 2006-01-01T00:08:00 | true | 9.39 g of potassium carbonate and 4.39 g of ethylene carbonate are added to 20 g of the product from Example A6 in 200 ml of anhydrous DMF. The reaction mixture is heated at 140° C. for 18 h. The salts which precipitate are filtered off and washed with toluene. The combined organic phase is freed of solvent in vac. and used directly for the further reaction. | OCCOc1ccc(-c2nnnc(-c3cccc4ccccc34)c2-c2cccc3ccccc23)c(O)c1 | null | Oc1ccc(-c2nnnc(-c3cccc4ccccc34)c2-c2cccc3ccccc23)c(O)c1 | O=C1OCCO1 | null | C(=O)([O-])[O-].[K+].[K+].[C:7]1(=O)[O:11][CH2:10][CH2:9][O:8]1.[C:13]1([C:23]2[N:28]=[N:27][N:26]=[C:25]([C:29]3[CH:34]=[CH:33]C(O)=[CH:31][C:30]=3[OH:36])[C:24]=2[C:37]2[C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[CH:40]=[CH:39][CH:38]=2)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1>CN(C=O)C>[C:13]1([C:23]2[N:28]=[N:27][N:26]=[C:25]([C:29]3[CH:34]=[CH:33][C:7]([O:11][CH2:10][CH2:9][OH:8])=[CH:31][C:30]=3[OH:36])[C:24]=2[C:37]2[C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[CH:40]=[CH:39][CH:38]=2)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1 | null | CN(C)C=O | null | null | 140 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,685,564 | null | null | null | null | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | 2016-01-01T00:01:00 | true | To a stirred solution of ethyl 6-chloro-4-(isopropylamino)nicotinate (2) (3 g, 12.39 mmol) in ethanol (10 mL), hydrazine hydrate (3 mL) was added and refluxed at 80° C. for 3 h. The reaction mixture was cooled and concentrated to obtain crude compound. The residue obtained was triturated with diethyl ether and hexane and filtered to get solid, 6-chloro-4-(isopropylamino)nicotinohydrazide (10). LC/MS: Acquity BEH C18 2.1×50 mm, 1.8 micron; Solvent A=0.1% TFA in water; Solvent B=0.1% TFA in ACN; gradient 0-100% B over 2 min; retention time: 0.58 min; LCMS (ES-API), m/z 229.6 (M+H). | CC(C)Nc1cc(Cl)ncc1C(=O)NN | null | NN | CCOC(=O)c1cnc(Cl)cc1NC1CCC1 | null | [Cl:1][C:2]1[CH:12]=[C:11]([NH:13][CH:14]2[CH2:17]C[CH2:15]2)[C:5]([C:6](OCC)=[O:7])=[CH:4][N:3]=1.O.[NH2:19][NH2:20]>C(O)C>[Cl:1][C:2]1[CH:12]=[C:11]([NH:13][CH:14]([CH3:17])[CH3:15])[C:5]([C:6]([NH:19][NH2:20])=[O:7])=[CH:4][N:3]=1 | null | CCO | O | null | 80 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,147,280 | CNOC | Cl | F[B-](F)(F)F | null | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | 2012-01-01T00:04:00 | true | 0.58 g of 2-(3-(3,4-dichlorobenzyl)ureido)thiazole-4-carboxylic acid was dissolved in 15 ml of DMF and 3.0 eq. of DIEA and 1.05 eq. of TBTU was added. To the mixture, 1.2 eq. of N,O-dimethylhydroxylamine HCl salt was added and the reaction was stirred at room temp. overnight. The product was precipitated from water, filtered, washed with water and dried to give 2-(3-(3,4-dichlorobenzyl)ureido)-N-methoxy-N-methylthiazole-4-carboxamide. | CON(C)C(=O)c1csc(NC(=O)NCc2ccc(Cl)c(Cl)c2)n1 | null | CN(C)C(On1nnc2ccccc21)=[N+](C)C | O=C(NCc1ccc(Cl)c(Cl)c1)Nc1nc(C(=O)O)cs1 | null | [Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[Cl:21])[CH2:5][NH:6][C:7](=[O:17])[NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14]([OH:16])=O)[N:13]=1.CCN(C(C)C)C(C)C.CN([C:34]([O:38][N:39]1N=NC2C=CC=C[C:40]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.Cl.CNOC>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[Cl:21])[CH2:5][NH:6][C:7](=[O:17])[NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14]([N:39]([O:38][CH3:34])[CH3:40])=[O:16])[N:13]=1 | 8 | CN(C)C=O | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,117,729 | null | null | null | null | ord_dataset-4226e9b4f9f845db967ed997270dcafc | 2011-01-01T00:12:00 | true | To a stirred solution of 4-(bromomethyl)-3-nitrobenzonitrile (5.12 g, 21.57 mmol) and pyrrolidine (1.84 g, 25.88 mmol) in CH2Cl2 (72 mL) was added triethylamine (6.54 g, 64.71 mmol) dropwise at 0° C. The mixture was stirred at room temperature for 1.5 h and evaporated to dryness under reduced pressure. The residue was diluted with water (30 mL) and extracted with CH2Cl2 (3×100 mL). The CH2Cl2 solution was dried over anhydrous Na2SO4, filtered, and evaporated to dryness under reduced pressure. The residue was purified by MPLC on silica gel using a mixture of EtOAc and hexane as eluent to give 3-nitro-4-(pyrrolidin-1-ylmethyl)benzonitrile (2.24 g, 45%) as a yellow solid. 1H NMR (400 MHz, CDCl3): δ 8.16 (d, 1 H, J=1.6 Hz), 7.94 (br d, 1H, J=8.0 Hz), 7.83 (dd, 1H, J=8.0, 1.6 Hz), 3.99 (s, 2H), 2.54 (br s, 4H), 1.79 (m, 4H). | N#Cc1ccc(CN2CCCC2)c([N+](=O)[O-])c1 | null | C1CCNC1 | N#Cc1ccc(CBr)c([N+](=O)[O-])c1 | null | Br[CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[N+:11]([O-:13])=[O:12].[NH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.C(N(CC)CC)C>C(Cl)Cl>[N+:11]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:3]=1[CH2:2][N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)[C:7]#[N:8])([O-:13])=[O:12] | 1.5 | ClCCl | CCN(CC)CC | null | 25 | null | 44.9 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
71,504 | [K+] | null | null | null | ord_dataset-520610070b3c4780a03b44c7fcecc28f | 1980-01-01T00:10:00 | true | To a stirred suspension of 469 mg. of potassium thioacetate in 10 ml. of ethanol is added 1.76 g. of 1-[3-(4-bromobenzoyl)-3-bromopropionyl]-L-proline (Example 37). The mixture is stirred at room temperature for 18 hours, filtered and the filtrate evaporated to dryness. The residue is dissolved in dichloromethane, washed with water and saturated sodium chloride solution, dried over magnesium sulfate and evaporated to dryness in vacuo giving the desired product as 1.68 g. of a white glass. | CC(=O)SC(CC(=O)N1CCC[C@H]1C(=O)O)C(=O)c1ccc(Br)cc1 | null | CC([O-])=S | O=C(c1ccc(Br)cc1)C(Br)CC(=O)N1CCC[C@H]1C(=O)O | null | [C:1]([O-:4])(=[S:3])[CH3:2].[K+].[Br:6][C:7]1[CH:27]=[CH:26][C:10]([C:11]([CH:13](Br)[CH2:14][C:15]([N:17]2[CH2:24][CH2:23][CH2:22][C@H:18]2[C:19]([OH:21])=[O:20])=[O:16])=[O:12])=[CH:9][CH:8]=1>C(O)C>[C:1]([S:3][CH:13]([C:11](=[O:12])[C:10]1[CH:26]=[CH:27][C:7]([Br:6])=[CH:8][CH:9]=1)[CH2:14][C:15]([N:17]1[CH2:24][CH2:23][CH2:22][C@H:18]1[C:19]([OH:21])=[O:20])=[O:16])(=[O:4])[CH3:2] | 18 | CCO | null | null | 25 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
272,700 | [Pd] | null | null | null | ord_dataset-ee287d49cb8642e59ae9c3951f746312 | 1993-01-01T00:08:00 | true | 5-(4-[2-(N-Methyl-N-(2-benzothiazolyl)amino)ethoxy]benzylidene)-2,4-thiazolidinedione (2 g) in dry 1,4-dioxan (70 ml) was reduced under hydrogen in the presence of 10% palladium on charcoal (3 g) at ambient temperature and atmospheric pressure until hydrogen uptake ceased. The solution was filtered through diatomaceous earth, the filter pad was washed exhaustively with dioxan and the combined filtrates were evaporated to dryness under vacuum. The title compound (m.p. 167°-8° C.) was obtained after crystallisation from methanol. | CN(CCOc1ccc(CC2SC(=O)NC2=O)cc1)c1nc2ccccc2s1 | null | CN(CCOc1ccc(C=C2SC(=O)NC2=O)cc1)c1nc2ccccc2s1 | [H][H] | null | [CH3:1][N:2]([CH2:12][CH2:13][O:14][C:15]1[CH:28]=[CH:27][C:18]([CH:19]=[C:20]2[S:24][C:23](=[O:25])[NH:22][C:21]2=[O:26])=[CH:17][CH:16]=1)[C:3]1[S:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[H][H]>O1CCOCC1.[Pd]>[CH3:1][N:2]([CH2:12][CH2:13][O:14][C:15]1[CH:28]=[CH:27][C:18]([CH2:19][CH:20]2[S:24][C:23](=[O:25])[NH:22][C:21]2=[O:26])=[CH:17][CH:16]=1)[C:3]1[S:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1 | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,430,443 | CC(C)(C)c1ccc2c(=O)n(-c3cccc(-n4cc(C#N)c5ccccc54)c3C=O)ncc2c1 | null | null | null | ord_dataset-5e6956e6e8c24a168866a253f4a66c6c | 2014-01-01T00:05:00 | true | The preparation of 1-(3-(6-tert-butyl-1-oxophthalazin-2(1H)-yl)-2-formylphenyl)-1H-indole-3-carboxamide, via nitrile hydrolysis of 1-(3-(6-tert-butyl-1-oxophthalazin-2(1H)-yl)-2-formylphenyl)-1H-indole-3-carbonitrile (82 mg, 0.18 mmol) and use of catalyst hydrido(dimethylphosphinousacid-kp)[hydrogen bis-(dimethylphosphinito-kp)]platinum(II) catalyst (5 mg, 0.064 mmol) was carried out in a procedure analogous to that described in Example 18. Similar work up and purification provided desired product as a light yellow glassy solid (54 mg, 63% yield). LC/MS calcd for C28H24N4O3 (m/e) 464.5, obsd 465.0 (M+H, ES+): 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.44 (s, 9H) 7.21-7.37 (m, 3H) 7.48-7.59 (m, 2H) 7.67-7.76 (m, 2H) 7.85 (t, J=7.93, 1.00 Hz, 1H) 7.90 (s, 1H) 8.14-8.20 (m, 1H) 8.30 (s, 1H) 8.37 (d, J=8.31 Hz, 1H) 9.56 (s, 1H) | CC(C)(C)c1ccc2c(=O)n(-c3cccc(-n4cc(C(N)=O)c5ccccc54)c3CO)ncc2c1 | null | CC(C)(C)c1ccc2c(=O)n(-c3cccc(-n4cc(C(N)=O)c5ccccc54)c3C=O)ncc2c1 | null | null | [C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[N:10]([C:16]1[C:17]([CH:34]=[O:35])=[C:18]([N:22]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[C:24]([C:31]([NH2:33])=[O:32])=[CH:23]3)[CH:19]=[CH:20][CH:21]=1)[N:9]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2].C(C1C=C2C(=CC=1)C(=O)N(C1C(C=O)=C(N3C4C(=CC=CC=4)C(C#N)=C3)C=CC=1)N=C2)(C)(C)C>>[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[N:10]([C:16]1[C:17]([CH2:34][OH:35])=[C:18]([N:22]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[C:24]([C:31]([NH2:33])=[O:32])=[CH:23]3)[CH:19]=[CH:20][CH:21]=1)[N:9]=[CH:8]2)([CH3:4])([CH3:2])[CH3:3] | null | null | null | null | null | null | 63 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,196,979 | COc1nc(Cl)nc(OC)n1 | Cl | null | null | ord_dataset-4e81c470cc3b429faf5e1caa50f70a98 | 2012-01-01T00:08:00 | true | To a solution of 9 (254 mg, 0.8 mmol) in anhydrous DMF (10 mL) was added N-methylmorpholine (145 mg, 1.44 mmol) and 2-chloro-4,6-dimethoxy-1,3,5-triazine (253 g, 1.44 mmol). The resulting mixture was stirred at room temperature for 2 h. To this mixture were added N-methylmorpholine (145 mg, 1.44 mmol) and L-glutamate diethyl ester hydrochloride (290 mg, 1.2 mmol). The reaction mixture was stirred for an additional 4 h at room temperature and then evaporated to dryness under reduced pressure. The residue was dissolved in the minimum amount of CHCl3/MeOH (4:1) and chromatographed on a silica gel column (2×15 cm) and with 5% CHCl3 in MeOH as the eluent. Fractions that showed the desired spot (TLC) were pooled and the solvent evaporated to dryness to afford 252 mg of 10 as yellow powder in 63% yield. 1H NMR (DMSO-d6): δ 1.14-1.21 (m, 6H), 1.81-2.05 (m, 4H), 2.32-2.39 (t, J=7.6 Hz, 2H), 2.49-2.52 (t, J=7.2 Hz, 2H), 2.78-2.81 (t, J=7.2 Hz, 2H), 4.02-4.07 (m, 4H), 4.30-4.35 (m, 1H), 5.88 (s, 1H), 5.94 (s, 2H), 6.89-6.90 (d, J=3.6 Hz, 1H), 7.68-7.69 (d, J=3.6 Hz, 1H), 8.61-8.63 (d, J=8 Hz, 1H), 10.71 (s, 1H), 11.19 (s, 1H). | CCOC(=O)CC[C@H](NC(=O)c1ccc(CCCc2cc3c(=O)[nH]c(N)nc3[nH]2)s1)C(=O)OCC | null | Nc1nc2[nH]c(CCCc3ccc(C(=O)O)s3)cc2c(=O)[nH]1 | CCOC(=O)CC[C@H](N)C(=O)OCC | null | [NH2:1][C:2]1[NH:3][C:4](=[O:22])[C:5]2[CH:10]=[C:9]([CH2:11][CH2:12][CH2:13][C:14]3[S:18][C:17]([C:19]([OH:21])=O)=[CH:16][CH:15]=3)[NH:8][C:6]=2[N:7]=1.CN1CCOCC1.ClC1N=C(OC)N=C(OC)N=1.Cl.[CH2:42]([O:44][C:45](=[O:55])[C@H:46]([CH2:48][CH2:49][C:50]([O:52][CH2:53][CH3:54])=[O:51])[NH2:47])[CH3:43]>CN(C=O)C>[CH2:42]([O:44][C:45](=[O:55])[C@@H:46]([NH:47][C:19]([C:17]1[S:18][C:14]([CH2:13][CH2:12][CH2:11][C:9]2[NH:8][C:6]3[N:7]=[C:2]([NH2:1])[NH:3][C:4](=[O:22])[C:5]=3[CH:10]=2)=[CH:15][CH:16]=1)=[O:21])[CH2:48][CH2:49][C:50]([O:52][CH2:53][CH3:54])=[O:51])[CH3:43] | 2 | CN1CCOCC1 | CN(C)C=O | null | 25 | 62.6 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,627,369 | [Pd] | null | null | null | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | 2015-01-01T00:09:00 | true | A mixture of tert-butyl 4-(4-((4-((3-carbamoylphenyl)ethynyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)-3-methoxyphenyl)piperidine-1-carboxylate (I35) (0.073 g, 0.12 mmol) and 10% palladium on activated carbon (0.042 g) in DMF (3 mL) was stirred under a hydrogen atmosphere for 20 hours. The resulting mixture was filtered and filtrate evaporated to dryness under reduced pressure. The residue was chromatographed on silica gel (20-100% acetone/petroleum benzine 40-60° C.) to give the title compound (I36) (0.070 g, 95%). | COc1cc(C2CCNCC2)ccc1Nc1ncc(C(F)(F)F)c(CCc2cccc(C(N)=O)c2)n1 | null | COc1cc(C2CCN(C(=O)OC(C)(C)C)CC2)ccc1Nc1ncc(C(F)(F)F)c(C#Cc2cccc(C(N)=O)c2)n1 | null | null | [C:1]([C:4]1[CH:5]=[C:6]([C:10]#[C:11][C:12]2[C:17]([C:18]([F:21])([F:20])[F:19])=[CH:16][N:15]=[C:14]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([CH:29]4[CH2:34][CH2:33][N:32](C(OC(C)(C)C)=O)[CH2:31][CH2:30]4)=[CH:25][C:24]=3[O:42][CH3:43])[N:13]=2)[CH:7]=[CH:8][CH:9]=1)(=[O:3])[NH2:2]>[Pd].CN(C=O)C>[CH3:43][O:42][C:24]1[CH:25]=[C:26]([CH:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[CH:27]=[CH:28][C:23]=1[NH:22][C:14]1[N:13]=[C:12]([CH2:11][CH2:10][C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[C:1]([NH2:2])=[O:3])[C:17]([C:18]([F:19])([F:20])[F:21])=[CH:16][N:15]=1 | 20 | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
260,944 | [H-] | [Na+] | null | null | ord_dataset-ab5ba9f863cb41d9924be0bb3c730818 | 1993-01-01T00:01:00 | true | To methanol (5 ml) was added, under ice-cooling, 60% sodium hydride (213 mg), and the mixture was stirred for 5 minutes at room temperatures, to which was then added thiophenol (0.55 ml), followed by stirring for 15 hours. To the resultant mixture was added fumagillol (500 mg), which was stirred for 30 minutes, followed by adding water to suspend the reaction. The product was extracted with ethyl acetate, and the extract solution was washed with a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous saline solution, followed by drying over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by means of a silica gel column chromatography (carrier 25 g, developing solvent: ethyl acetate-hexane=1:2), followed by crystallization from isopropylether to afford 2-(1,2-epoxy-1,5-dimethyl-4-hexenyl)- 3-methoxy-1-phenylthiomethyl-1,4-cyclohexanediol (660 mg: yield 95%) as colorless crystals, m.p. 94° to 96° C. | COC1C(O)CCC(O)(CSc2ccccc2)C1C1(C)OC1CC=C(C)C | null | CO[C@@H]1[C@H](O)CC[C@]2(CO2)[C@H]1[C@@]1(C)O[C@@H]1CC=C(C)C | Sc1ccccc1 | null | CO.[H-].[Na+].[C:5]1([SH:11])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:12][C:13]([CH3:31])=[CH:14][CH2:15][C@H:16]1[O:18][C@@:17]1([C@@H:20]1[C@:25]2([O:27][CH2:26]2)[CH2:24][CH2:23][C@@H:22]([OH:28])[C@H:21]1[O:29][CH3:30])[CH3:19]>O>[O:18]1[CH:16]([CH2:15][CH:14]=[C:13]([CH3:31])[CH3:12])[C:17]1([CH:20]1[CH:21]([O:29][CH3:30])[CH:22]([OH:28])[CH2:23][CH2:24][C:25]1([CH2:26][S:11][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[OH:27])[CH3:19] | 15 | CO | O | null | null | 95 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,371,253 | OO | [Na+] | null | null | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | 2013-01-01T00:12:00 | true | A solution of ethyl 4-isopropylsulfanylbenzoate (350 mg, 1.6 mmol) and H2O2 (180 μL of 30% w/v, 1.6 mmol) in AcOH (2 mL) was stirred at ambient temperature for 3 h. The mixture was poured into sat. aq. Na2CO3 and the pH was adjusted to 10 with solid Na2CO3. The mixture was extracted with EtOAc (3×). The organics were combined and washed with sat. aq. Na2CO3, water (2×), then brine. The organic layer was dried over magnesium sulfate and was evaporated to dryness. The residue was purified by column chromatography (20-50% EtOAc in hexanes) to give ethyl 4-isopropylsulfinylbenzoate (65%). ESI-MS m/z calc. 240.1. found 241.3 (M+1)+. Retention time: 1.16 minutes (3 min run). | CCOC(=O)c1ccc(S(=O)C(C)C)cc1 | null | O=C([O-])[O-] | CCOC(=O)c1ccc(SC(C)C)cc1 | null | [CH:1]([S:4][C:5]1[CH:15]=[CH:14][C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][CH:6]=1)([CH3:3])[CH3:2].OO.C([O-])([O-])=[O:19].[Na+].[Na+]>CC(O)=O>[CH:1]([S:4]([C:5]1[CH:15]=[CH:14][C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][CH:6]=1)=[O:19])([CH3:2])[CH3:3] | null | CC(=O)O | null | null | null | 65 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
413,056 | null | null | null | null | ord_dataset-275344fd078b4340b89ca0b6e92beb95 | 1998-01-01T00:10:00 | true | 8.6 Grams of N-(2-aminoethyl)morpholine, 7.2 g of triethylamine and 120 ml of chloroform were charged in a flask equipped with a stirrer, a condenser and a calcium chloride drying tube and stirred with ice cooling. To the resulting solution was slowly added dropwise 18.2 g of hexadecyl chloroformate. After completion of the addition, the temperature of the solution was returned to room temperature, followed by refluxing with heating for 0.5 hour. The reaction mixture was cooled to room temperature, washed with water, dried over anhydrous magnesium sulfate and, then, concentrated under reduced pressure. The residue was recrystallized from acetonitrile to obtain 21.1 g of the desired product. m.p. 65° C. | CCCCCCCCCCCCCCCCOC(=O)NCCN1CCOCC1 | null | CCCCCCCCCCCCCCCCOC(=O)Cl | NCCN1CCOCC1 | null | [NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.C(N(CC)CC)C.Cl[C:18]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[O:19]>C(Cl)(Cl)Cl>[O:7]1[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][NH:1][C:18](=[O:19])[O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH2:5][CH2:6]1 | null | ClC(Cl)Cl | CCN(CC)CC | null | 25 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,537,912 | [Pd] | null | null | null | ord_dataset-8d5c200bca27407ab9febe7598e16458 | 2015-01-01T00:01:00 | true | A mixture of 3-[4-(benzyloxy)phenyl]-1-ethyl-6-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (0.68 g) and 10% palladium on carbon (0.30 g) in MeOH (15 mL) was hydrogenated under balloon pressure at room temperature for 2 h. The catalyst was removed by filtration and the filtrate was concentrated in vacuo to give 1-ethyl-3-(4-hydroxyphenyl)-6-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (0.50 g) as a pale yellow solid. | CCn1c(=O)n(-c2ccc(O)cc2)c2ncc(C)cc21 | null | CCn1c(=O)n(-c2ccc(OCc3ccccc3)cc2)c2ncc(C)cc21 | null | null | C([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:19]3=[N:20][CH:21]=[C:22]([CH3:24])[CH:23]=[C:18]3[N:17]([CH2:25][CH3:26])[C:16]2=[O:27])=[CH:11][CH:10]=1)C1C=CC=CC=1>[Pd].CO>[CH2:25]([N:17]1[C:18]2[C:19](=[N:20][CH:21]=[C:22]([CH3:24])[CH:23]=2)[N:15]([C:12]2[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=2)[C:16]1=[O:27])[CH3:26] | 2 | CO | null | null | null | 98.1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
441,021 | null | null | null | null | ord_dataset-3e8f24b5bc8e4d8bb9b6e7e89a956e12 | 1999-01-01T00:09:00 | true | 37.6 g 4-amino-2-(1-piperazinyl)-6,7-dimethoxyquinazoline and 15.8 g triethylamine are suspended in 400 ml methylene chloride. The suspension is cooled to -5° C. This suspension is stirred while 21.0 g tetrahydrofuran-2-carboxylic acid chloride are added drop by drop. The suspension is continued to be stirred for two hours at 0° C., thereafter the solvent is distilled off under vacuum. 200 ml methanol and 200 ml acetone are added to the residue. The resulting suspension is kept under reflux for 0.5 hours while stirring. Thereafter, it is cooled to 0° C. The product is isolated by filtration. 78 g of moist terazosin base are obtained. | COc1cc2nc(N3CCN(C(=O)C4CCCO4)CC3)nc(N)c2cc1OC | null | O=C(Cl)C1CCCO1 | COc1cc2nc(N3CCNCC3)nc(N)c2cc1OC | null | [NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[N:3]=1.C(N(CC)CC)C.[O:29]1[CH2:33][CH2:32][CH2:31][CH:30]1[C:34](Cl)=[O:35]>C(Cl)Cl>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:2]([NH2:1])=[N:3][C:4]([N:16]3[CH2:21][CH2:20][N:19]([C:34]([CH:30]4[O:29][CH2:33][CH2:32][CH2:31]4)=[O:35])[CH2:18][CH2:17]3)=[N:5][C:6]2=[CH:7][C:8]=1[O:14][CH3:15] | 2 | CCN(CC)CC | ClCCl | null | -5 | 154.9 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,373,889 | null | null | null | null | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | 2013-01-01T00:12:00 | true | 1-Chloro-4-nitro-benzene (5.0 g, 31.7 mmol) was added to excess aqueous methylamine solution-(40%, 30 mL) and heated in a pressure bomb for 16 h. The reaction mass was cooled to room temperature and a solid filtered off. The filtrate was evaporated to dryness and the combined solids were purified by trituration with pentane to afford methyl-(4-nitro-phenyl)-amine (4.5 g, 93%) as a solid. | CNc1ccc([N+](=O)[O-])cc1 | null | CN | O=[N+]([O-])c1ccc(Cl)cc1 | null | Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH3:11][NH2:12]>>[CH3:11][NH:12][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1 | null | null | null | null | 25 | 93 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
3,388 | [Cl-] | [Li]CCCC | [NH4+] | null | ord_dataset-15ce1bcfb62046d9bec87d32620888d5 | 1976-01-01T00:03:00 | true | To a flask equipped with a stirrer, dropping funnel, condenser and gas inlet tube maintained under a nitrogen atmosphere there is added at room temperature 19.7 g (0.146 mole) of N-methyl benzamide and 400 ml. dry tetrahydrofuran. The reaction flask is immersed in an ice bath and cooled to an internal temperature of 5°C. Stirring is initiated and 204 ml. of 1.6 M. n-butyl lithium (~0.321 mole) in hexane is added dropwise over about 1 hour maintaining the temperature below 8°C. The resulting dilithio salt is stirred at 5°C. for an additional hour and then a solution of 40 g. (0.146 mole) of 4'-chloro-2-dimethylaminomethyl benzophenone in 500 ml. tetrahydrofuran is added dropwise over about 1 hour maintaining the temperature between -10 to 10°C. The resulting mixture is stirred at 5°C. for 1 hour longer and 150 ml. of saturated ammonium chloride is added maintaining the temperature at about 10°C. The layers are separated and the organic phase dried over ahydrous magnesium sulfate, filtered and evaporated in vacuo. The residue is crystallized from ether to give α-(4-chlorophenyl)-α-(2-dimethylaminomethyl phenyl)-α-hydroxy-N-methyl-o-toluamide; m.p. 154°-156°C. | CNC(=O)c1ccccc1C(O)(c1ccc(Cl)cc1)c1ccccc1CN(C)C | null | CN(C)Cc1ccccc1C(=O)c1ccc(Cl)cc1 | CNC(=O)c1ccccc1 | null | [CH3:1][NH:2][C:3](=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C([Li])CCC.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:23](=[O:34])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH2:30][N:31]([CH3:33])[CH3:32])=[CH:19][CH:18]=1.[Cl-].[NH4+]>CCCCCC.O1CCCC1>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH2:30][N:31]([CH3:33])[CH3:32])([OH:34])[C:5]2[C:4]([C:3]([NH:2][CH3:1])=[O:10])=[CH:9][CH:8]=[CH:7][CH:6]=2)=[CH:19][CH:18]=1 | null | CCCCCC | C1CCOC1 | null | 5 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
89,718 | Cl | [Na+] | [OH-] | null | ord_dataset-aeb5378e6e67443e8a4f5c7a5ec3de51 | 1981-01-01T00:12:00 | true | 1.2 g (0.005 mol) of 2-(2-chloroethyl)-2,3,5,8-tetrahydro-1,3-dioxo-1H-1,2,4-triazolo[1,2-a]pyridazine-5-carboxylic acid were dissolved in 10 ml (0.10 mol) of 1-M sodium hydroxide solution. The solution was treated with 1 ml (0.008 mol) of benzyl mercaptan and the mixture was stirred at 100° C. for 3 hours. The mixture was acidified with concentrated hydrochloric acid and extracted with two 20 ml portions of ethyl acetate. The organic layer was extracted with 50 ml of saturated sodium bicarbonate solution. The aqueous extract was acidified with concentrated hydrochloric acid and re-extracted with two 25 ml portions of ethyl acetate. The organic extracts were dried over magnesium sulphate and evaporated to give 2-(2-benzylthioethyl)-2,3,5,8-tetrahydro-1,3-dioxo-1H-1,2,4-triazolo[1,2-a]pyridazine-5-carboxylic acid in the form of a colourless oil. | O=C(O)C1C=CCn2c(=O)n(CCSCc3ccccc3)c(=O)n21 | null | O=C(O)C1C=CCn2c(=O)n(CCCl)c(=O)n21 | SCc1ccccc1 | null | Cl[CH2:2][CH2:3][N:4]1[C:15](=[O:16])[N:7]2[CH2:8][CH:9]=[CH:10][CH:11]([C:12]([OH:14])=[O:13])[N:6]2[C:5]1=[O:17].[CH2:18]([SH:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>[OH-].[Na+]>[CH2:18]([S:25][CH2:2][CH2:3][N:4]1[C:15](=[O:16])[N:7]2[CH2:8][CH:9]=[CH:10][CH:11]([C:12]([OH:14])=[O:13])[N:6]2[C:5]1=[O:17])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1 | 3 | null | null | null | 100 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
672,586 | Cl | null | null | null | ord_dataset-e90cd41afe844e49875435eb99903799 | 2005-01-01T00:05:00 | true | A mixture of 47.79 g 3-iodoaniline, 27.7 ml ethyl acetoacetate and 0.13 ml 37% hydrochlorid acid in 65 ml benzene is boiled under a reflux condenser fitted with a water separator. After 4 h. 4 ml of water have been collected. The solvent is removed at reduced pressure and the residual oil dried in vacuo 3-(3-iodo-phenylamino)-but-2-enoic acid ethyl ester is obtained as a light brown oil. MS (ISP): 332.1 (M+H)+. | CCOC(=O)C=C(C)Nc1cccc(I)c1 | null | CCOC(=O)CC(C)=O | Nc1cccc(I)c1 | null | [I:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[C:9]([O:15][CH2:16][CH3:17])(=[O:14])[CH2:10][C:11]([CH3:13])=O.Cl.O>C1C=CC=CC=1>[CH2:16]([O:15][C:9](=[O:14])[CH:10]=[C:11]([NH:5][C:4]1[CH:6]=[CH:7][CH:8]=[C:2]([I:1])[CH:3]=1)[CH3:13])[CH3:17] | 4 | O | 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 |
1,440,898 | null | null | null | null | ord_dataset-275a3da8f45f4536ad29727f0ef9ba66 | 2014-01-01T00:06:00 | true | This compound was prepared by using procedures analogous to those described for the synthesis of Example 77 starting from N-[3-(7-{1-[3-(cyanomethyl)azetidin-3-yl]-1H-pyrazol-4-yl}imidazo[1,2-b]pyridazin-3-yl)phenyl]-N′-(2,2,2-trifluoroethyl)urea and tetrahydrofuran-3-carboxylic acid. LCMS (M+H)+: m/z=594.2. | N#CCC1(n2cc(-c3cnn4c(-c5cccc(NC(=O)NCC(F)(F)F)c5)cnc4c3)cn2)CN(C(=O)C2CCOC2)C1 | null | N#CCC1(n2cc(-c3cnn4c(-c5cccc(NC(=O)NCC(F)(F)F)c5)cnc4c3)cn2)CNC1 | O=C(O)C1CCOC1 | null | [C:1]([CH2:3][C:4]1([N:8]2[CH:12]=[C:11]([C:13]3[CH:18]=[N:17][N:16]4[C:19]([C:22]5[CH:23]=[C:24]([NH:28][C:29]([NH:31][CH2:32][C:33]([F:36])([F:35])[F:34])=[O:30])[CH:25]=[CH:26][CH:27]=5)=[CH:20][N:21]=[C:15]4[CH:14]=3)[CH:10]=[N:9]2)[CH2:7][NH:6][CH2:5]1)#[N:2].[O:37]1[CH2:41][CH2:40][CH:39]([C:42](O)=[O:43])[CH2:38]1>>[C:1]([CH2:3][C:4]1([N:8]2[CH:12]=[C:11]([C:13]3[CH:18]=[N:17][N:16]4[C:19]([C:22]5[CH:23]=[C:24]([NH:28][C:29]([NH:31][CH2:32][C:33]([F:35])([F:36])[F:34])=[O:30])[CH:25]=[CH:26][CH:27]=5)=[CH:20][N:21]=[C:15]4[CH:14]=3)[CH:10]=[N:9]2)[CH2:5][N:6]([C:42]([CH:39]2[CH2:40][CH2:41][O:37][CH2:38]2)=[O:43])[CH2:7]1)#[N: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 |
619,295 | [Pd] | O=C[O-] | [NH4+] | null | ord_dataset-2952e63264f5422a84e12cca1e0541ee | 2003-01-01T00:12:00 | true | A mixture of 1 g (4.3 mmole) (4S,5S)-5-(4-tert-butylphenyl)-4-methyl-oxazolidin-2-one p(see preparation 4, step 2), 2 g (31.74 mmole) ammonium formate and 0.1 g 10% palladium on carbon in 25 mL methanol was heated under reflux for 2 hrs. The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was partitioned between 10 mL 10% sodium carbonate and 25 mL ethyl acetate. The organic phase was dried (magnesium sulfate) and concentrated under reduced pressure. The title compound was isolated as the hydrochloride salt from diethyl ether, 0.93 g (95%), m.p. 259.5-261.3° C. | C[C@H](N)Cc1ccc(C(C)(C)C)cc1 | null | C[C@@H]1NC(=O)O[C@H]1c1ccc(C(C)(C)C)cc1 | null | null | [C:1]([C:5]1[CH:10]=[CH:9][C:8]([C@@H:11]2OC(=O)[NH:13][C@H:12]2[CH3:17])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>[Pd].CO>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:11][C@@H:12]([NH2:13])[CH3:17])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3] | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
960,003 | CN(C)c1ccncc1 | null | null | null | ord_dataset-ed65749688da45af8a8432967b017729 | 2010-01-01T00:05:00 | true | (2S)—N-(tert-Butoxycarbonyl)-3-(pyridin-3-yl)alanine (25.00 g, 93.88 mmol) is dissolved in 300 ml of dichloromethane under argon. Methanol (11.4 ml, 9.02 g, 281 mmol, 3 equivalents) and one grain of DMAP are added. The mixture is then cooled to 0° C. EDC (19.80 g, 103 mmol, 1.1 equivalents) is added. After 5 min, the ice bath is removed and the mixture is left to stir at RT over 1 h. The mixture is then concentrated in vacuo, and ethyl acetate is added to the residue and the mixture is extracted against a saturated sodium hydrogen carbonate solution. The aqueous phase is reextracted once with ethyl acetate, then the combined organic phases are washed with 0.5 M citric acid and then once again with a saturated sodium hydrogen carbonate solution. The organic phase is dried over sodium sulfate, filtered and concentrated in vacuo. An oil remains, which crystallizes during drying in an oil-pump vacuum. Yield: 23.60 g (90% of theory). | COC(=O)[C@H](Cc1cccnc1)NC(=O)OC(C)(C)C | null | CC(C)(C)OC(=O)N[C@@H](Cc1cccnc1)C(=O)O | ClCCCl | null | [C:1]([O:5][C:6]([NH:8][C@H:9]([C:17]([OH:19])=[O:18])[CH2:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.[CH2:22](Cl)CCl>ClCCl.CN(C1C=CN=CC=1)C>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17]([O:19][CH3:22])=[O:18])[CH2:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3] | 0.08 | CO | ClCCl | 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 |
742,690 | [Na+] | [OH-] | null | null | ord_dataset-437aa6654d5044ddaef3346dc4c6e08a | 2006-01-01T00:11:00 | true | At 0° C. to the solution of 250 mg (0196 mmol) of Boc-Lys(ClZ)-Arg(Tos)-Pro-Ala-Lys(ClZ)-OBzl (SEQ ID NO: 15) in 6 ml of methanol 5 ml of the solution of NaOH in methanol (2 mol/L) were added. The reaction mixture was stirred at 0° C. for 2 h and TLC (chloroform/methanol, 15:1) indicated complete disappearance of Boc-Lys(ClZ)-Arg(Tos)-Pro-Ala-Lys(ClZ)-Obzl (SEQ ID NO: 15). The reaction mixture was neutralized to pH 7 and evaporated at room temperature to remove methanol. The residue was acidified to pH 1–2 with hydrochloric acid (2 mol/L) to provide 200 mg (86%) of the title compound as a colorless powder. | 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)O)cc1 | null | 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 | null | [NH:1]([C:82]([O:84][C:85]([CH3:88])([CH3:87])[CH3:86])=[O:83])[C@H:2]([C:19]([NH:21][C@H:22]([C:40]([N:42]1[CH2:81][CH2:80][CH2:79][C@H:43]1[C:44]([NH:46][C@H:47]([C:49]([NH:51][C@H:52]([C:69]([O:71]CC1C=CC=CC=1)=[O:70])[CH2:53][CH2:54][CH2:55][CH2:56][NH:57][C:58]([O:60][CH2:61][C:62]1[CH:68]=[CH:67][CH:66]=[CH:65][C:63]=1[Cl:64])=[O:59])=[O:50])[CH3:48])=[O:45])=[O:41])[CH2:23][CH2:24][CH2:25][NH:26][C:27](=[NH:39])[NH:28][S:29]([C:32]1[CH:38]=[CH:37][C:35]([CH3:36])=[CH:34][CH:33]=1)(=[O:31])=[O:30])=[O:20])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=1[Cl:14])=[O:9].[OH-].[Na+].C(Cl)(Cl)Cl.CO>CO>[NH:1]([C:82]([O:84][C:85]([CH3:86])([CH3:88])[CH3:87])=[O:83])[C@H:2]([C:19]([NH:21][C@H:22]([C:40]([N:42]1[CH2:81][CH2:80][CH2:79][C@H:43]1[C:44]([NH:46][C@H:47]([C:49]([NH:51][C@H:52]([C:69]([OH:71])=[O:70])[CH2:53][CH2:54][CH2:55][CH2:56][NH:57][C:58]([O:60][CH2:61][C:62]1[CH:68]=[CH:67][CH:66]=[CH:65][C:63]=1[Cl:64])=[O:59])=[O:50])[CH3:48])=[O:45])=[O:41])[CH2:23][CH2:24][CH2:25][NH:26][C:27](=[NH:39])[NH:28][S:29]([C:32]1[CH:33]=[CH:34][C:35]([CH3:36])=[CH:37][CH:38]=1)(=[O:31])=[O:30])=[O:20])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=1[Cl:14])=[O:9] | 2 | CO | ClC(Cl)Cl | null | 0 | 86.1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,698,412 | O=C([O-])[O-] | [Cs+] | null | null | ord_dataset-54347fcace774f89850681d6dec8009f | 2016-01-01T00:03:00 | true | A solution of 410 mg (1.2 mmol) 6-chloro-2-ethylsulfanyl-N-[(3-fluorophenyl)-methyl]-4-methyl-pyridine-3-carboxylic acid amide (synthesis is described in section b) of example 2), 125 mg (1.0 mmol) 3-methoxy-azetidine and 824 mg (2.53 mmol) Cs2CO3 in 1,4-dioxane (7 ml) was heated at 110° C. for 24 h. Subsequently the RM was concentrated in vacuo. The residue obtained was partitioned between water and EtOAc. The organic layer was separated, dried over MgSO4 and concentrated in vacuo. Purification of the residue by CC (hexane/EtOAc 3:1) provided 122 mg (0.31 mmol, 31%) 2-ethylsulfanyl-N-[(3-fluorophenyl)-methyl]-6-(3-methoxy-azetidin-1-yl)-4-methyl-pyridine-3-carboxylic acid amide (example 6). [M+H]+ 390.2. | CCSc1nc(N2CC(OC)C2)cc(C)c1C(=O)NCc1cccc(F)c1 | null | COC1CNC1 | CCSc1nc(Cl)cc(C)c1C(=O)NCc1cccc(F)c1 | null | Cl[C:2]1[N:7]=[C:6]([S:8][CH2:9][CH3:10])[C:5]([C:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)=[O:12])=[C:4]([CH3:22])[CH:3]=1.[CH3:23][O:24][CH:25]1[CH2:28][NH:27][CH2:26]1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1>[CH2:9]([S:8][C:6]1[C:5]([C:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)=[O:12])=[C:4]([CH3:22])[CH:3]=[C:2]([N:27]2[CH2:28][CH:25]([O:24][CH3:23])[CH2:26]2)[N:7]=1)[CH3:10] | null | C1COCCO1 | null | null | null | 31 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
741,148 | null | null | null | null | ord_dataset-437aa6654d5044ddaef3346dc4c6e08a | 2006-01-01T00:11:00 | true | 4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,5-dimethylaniline (51 mg) was dissolved in N,N-dimethylformamide (2 ml) and triethylamine (1 ml) to prepare a solution. Thiophosgene (51 mg) was then added to the solution, and the mixture was stirred at room temperature for 6 hr. Next, 1-(2-aminoethyl)pyrrolidine (50 mg) was added thereto, and the mixture was further stirred at room temperature for 16 hr. Ethyl acetate was added to the reaction solution, followed by washing with water and saturated brine in that order. The organic layer was then dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by HPLC using chloroform/methanol for development to give the title compound (8 mg, yield 10%). | COc1cc2nccc(Oc3cc(C)c(NC(=S)NCCN4CCCC4)cc3C)c2cc1OC | null | COc1cc2nccc(Oc3cc(C)c(N)cc3C)c2cc1OC | NCCN1CCCC1 | S=C(Cl)Cl | [CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[C:22]([CH3:23])=[CH:21][C:19]([NH2:20])=[C:18]([CH3:24])[CH:17]=1.C(N(CC)CC)C.[C:32](Cl)(Cl)=[S:33].[NH2:36][CH2:37][CH2:38][N:39]1[CH2:43][CH2:42][CH2:41][CH2:40]1>CN(C)C=O.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[C:22]([CH3:23])=[CH:21][C:19]([NH:20][C:32]([NH:36][CH2:37][CH2:38][N:39]2[CH2:43][CH2:42][CH2:41][CH2:40]2)=[S:33])=[C:18]([CH3:24])[CH:17]=1 | 6 | CCN(CC)CC | CN(C)C=O | CCOC(C)=O | 25 | 10.6 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
397,026 | O=S(=O)(O)O | null | null | null | ord_dataset-a4a191e812a64d0598ea918f047e8da7 | 1998-01-01T00:04:00 | true | To 2.8 g of concentrated nitric acid was added dropwise 3.7 g of concentrated sulfuric acid at room temperature, followed by stirring for 10 minutes to obtain a mixed acid solution. A 0.5 g quantity of 5-amino-3-(2,6-dichloro-4-trifluoromethylphenyl)-1-methylpyrazole (13) was added in small portions to the solution at 60° C., and the mixture was stirred at the same temperature for 1 hour. The reaction mixture was added to water, the resulting mixture was extracted with ether, and the aqueous layer was made weakly alkaline with a saturated sodium carbonate aqueous solution and then extracted with ethyl acetate, followed by washing with brine and drying over anhydrous magnesium sulfate. Removal of the solvent gave 0.2 g of the desired compound in the form of orange crystals (yield 35.1%), m.p. 107°-108° C. | Cn1nc(-c2c(Cl)cc(C(F)(F)F)cc2Cl)c([N+](=O)[O-])c1N | null | Cn1nc(-c2c(Cl)cc(C(F)(F)F)cc2Cl)cc1N | O=[N+]([O-])O | null | [N+:1]([O-:4])(O)=[O:2].S(=O)(=O)(O)O.[NH2:10][C:11]1[N:15]([CH3:16])[N:14]=[C:13]([C:17]2[C:22]([Cl:23])=[CH:21][C:20]([C:24]([F:27])([F:26])[F:25])=[CH:19][C:18]=2[Cl:28])[CH:12]=1>O>[NH2:10][C:11]1[N:15]([CH3:16])[N:14]=[C:13]([C:17]2[C:22]([Cl:23])=[CH:21][C:20]([C:24]([F:25])([F:27])[F:26])=[CH:19][C:18]=2[Cl:28])[C:12]=1[N+:1]([O-:4])=[O:2] | 0.17 | 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 |
183,244 | N | null | null | null | ord_dataset-f25e1b7f8ef54305a5170f5395a768c7 | 1989-01-01T00:01:00 | true | 1-[3,4-Bis(acetyloxy)benzoyl]-2-imidazolidinone (11 g, 0.035 mol) was suspended in a mixture of 50 ml of ethanol and 50 ml of water, 4.2 ml (0.07 mol) of aqueous ammonia solution was added with stirring. After 15 minutes, a clear solution was formed, which was evaporated to a small volume. 1-(3,4-Dihydroxybenzoyl)-2-imidazolidinone crystallized out yielding 6.1 g of the title compound, melting point 208°-210° C. | O=C1NCCN1C(=O)c1ccc(O)c(O)c1 | null | CC(=O)Oc1ccc(C(=O)N2CCNC2=O)cc1OC(C)=O | null | null | C([O:4][C:5]1[CH:6]=[C:7]([CH:16]=[CH:17][C:18]=1[O:19]C(=O)C)[C:8]([N:10]1[CH2:14][CH2:13][NH:12][C:11]1=[O:15])=[O:9])(=O)C.N>C(O)C.O>[OH:4][C:5]1[CH:6]=[C:7]([CH:16]=[CH:17][C:18]=1[OH:19])[C:8]([N:10]1[CH2:14][CH2:13][NH:12][C:11]1=[O:15])=[O:9] | 0.25 | O | CCO | null | null | 78.4 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,728,542 | [Cl-] | null | null | null | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | 2016-01-01T00:05:00 | true | Prepared according to example 38c starting from 300 mg (0.58 mmol) of 10-(3-Carboxy-azetidin-1-yl)-5,6,8,9-tetrahydro-1,4,7,10a-tetraaza-cyclohept[f]indene-7-carboxylic acid tert-butyl ester (as DIPEA salt) and 120 mg (0.70 mmol) of 4,4-Difluoro-perhydro-azepinium chloride. | CC(C)(C)OC(=O)N1CCc2nc3ccnn3c(N3CC(C(=O)N4CCCC(F)(F)CC4)C3)c2CC1 | null | CC(C)(C)OC(=O)N1CCc2nc3ccnn3c(N3CC(C(=O)O)C3)c2CC1 | FC1(F)CCC[NH2+]CC1 | null | [C:1]([O:5][C:6]([N:8]1[CH2:28][CH2:27][C:12]2=[C:13]([N:20]3[CH2:23][CH:22]([C:24](O)=[O:25])[CH2:21]3)[N:14]3[C:18]([N:19]=[C:11]2[CH2:10][CH2:9]1)=[CH:17][CH:16]=[N:15]3)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl-].[F:30][C:31]1([F:38])[CH2:37][CH2:36][CH2:35][NH2+:34][CH2:33][CH2:32]1>>[C:1]([O:5][C:6]([N:8]1[CH2:28][CH2:27][C:12]2=[C:13]([N:20]3[CH2:21][CH:22]([C:24]([N:34]4[CH2:35][CH2:36][CH2:37][C:31]([F:38])([F:30])[CH2:32][CH2:33]4)=[O:25])[CH2:23]3)[N:14]3[C:18]([N:19]=[C:11]2[CH2:10][CH2:9]1)=[CH:17][CH:16]=[N:15]3)=[O:7])([CH3:4])([CH3:3])[CH3:2] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
765,560 | null | null | null | null | ord_dataset-7a8649d55889427e85b208ae89475895 | 2007-01-01T00:04:00 | true | A solution of example 673A (550 mg, 1.64 mmol) in CHCl3 (5 mL) was treated with SOCl2 (5 mL), stirred at room temperature for 3 hours then concentrated to give the title compound. MS (ESI (+)) m/e 352.7, 354.7 (M+H)+. | Nc1ncc(-c2cccc(CCl)c2)c2scc(Br)c12 | null | O=S(Cl)Cl | Nc1ncc(-c2cccc(CO)c2)c2scc(Br)c12 | null | [NH2:1][C:2]1[C:7]2[C:8]([Br:11])=[CH:9][S:10][C:6]=2[C:5]([C:12]2[CH:13]=[C:14]([CH2:18]O)[CH:15]=[CH:16][CH:17]=2)=[CH:4][N:3]=1.O=S(Cl)[Cl:22]>C(Cl)(Cl)Cl>[Br:11][C:8]1[C:7]2[C:2]([NH2:1])=[N:3][CH:4]=[C:5]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][Cl:22])[CH:13]=3)[C:6]=2[S:10][CH:9]=1 | 3 | ClC(Cl)Cl | 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 |
1,163,199 | null | null | null | null | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | 2012-01-01T00:05:00 | true | 5-(5-Ethyl-2-methyl-6-oxo-1,6-dihydropyridin-3-yl)thiophene-2-sulfonyl chloride is reacted with methyl(1-methylpyrrolidin-3-yl)amine as described in Steps 5 and 6, Example 24 to give the title compound as a yellow solid (90% yield). LC/MS: RT 2.12 min; m/e 396; 1H NMR (δ, ppm): 11.82 (1H, br), 7.61 (1H, d), 7.37 (1H, s), 7.22 (1H, d), 4.08 (1H, m), 2.76 (3H, s), 2.20-2.69 (m), 1.94 (1H, m), 1.55 (1H, m), 1.10 (3H, t). | CCc1cc(-c2ccc(S(=O)(=O)N(C)C3CCN(C)C3)s2)c(C)[nH]c1=O | Cl | CCc1cc(-c2ccc(S(=O)(=O)Cl)s2)c(C)[nH]c1=O | CNC1CCN(C)C1 | null | [CH2:1]([C:3]1[C:8](=[O:9])[NH:7][C:6]([CH3:10])=[C:5]([C:11]2[S:15][C:14]([S:16]([Cl:19])(=[O:18])=[O:17])=[CH:13][CH:12]=2)[CH:4]=1)[CH3:2].[CH3:20][NH:21][CH:22]1[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23]1>>[ClH:19].[CH3:20][N:21]([CH:22]1[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23]1)[S:16]([C:14]1[S:15][C:11]([C:5]2[CH:4]=[C:3]([CH2:1][CH3:2])[C:8](=[O:9])[NH:7][C:6]=2[CH3:10])=[CH:12][CH:13]=1)(=[O:18])=[O:17] | null | 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 |
183,562 | Cl | O=C([O-])[O-] | [Na+] | null | ord_dataset-8537fa92abf34c849134600c0c2bbcc7 | 1989-01-01T00:02:00 | true | N-methyl-2-(4-methylaminocarbonylmethoxyphenyl)-1-methylethanamine hydrochloride (2.73 g) was suspended in tetrahydrofuran (10 ml) containing triethylamine (6 ml) and a solution of α-bromoacetophenone (1.99 g) in tetrahydrofuran (10 ml) was added dropwise. After stirring overnight this solution was treated with saturated sodium carbonate solution, extracted with dichloromethane, the organic phase was dried (magnesium sulphate), filtered and evaporated to give a red oil which was used without further purification. | CNC(=O)COc1ccc(CC(C)N(C)CC(=O)c2ccccc2)cc1 | null | CNC(=O)COc1ccc(CC(C)NC)cc1 | O=C(CBr)c1ccccc1 | null | Cl.[CH3:2][NH:3][CH:4]([CH3:18])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]([NH:16][CH3:17])=[O:15])=[CH:8][CH:7]=1.C(N(CC)CC)C.Br[CH2:27][C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:29].C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1>[CH3:2][N:3]([CH:4]([CH3:18])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]([NH:16][CH3:17])=[O:15])=[CH:8][CH:7]=1)[CH2:27][C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:29] | 8 | CCN(CC)CC | 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 |
793,764 | [I-] | [K+] | null | null | ord_dataset-744b04e8228742eb9aa4bde36f5dedf1 | 2007-01-01T00:10:00 | true | (2S)-2-{[(R)-(4-bromophenyl)(phenyl)methyl]oxy}-N-(cyanomethyl)-4-methylpentanamide from example 68 (150 mg, 0.361 mmol), 4-(methylthio)phenyl boronic acid (67 mg, 0.398 mmol, 1.1 eg), [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium (II)complex) (7.9 mg, 0.011 mmol, 0.03 eg), potassium iodide (180 mg, 1.08 mmol, 3 eg), potassium carbonate (149 mg, 1.08 mmol, 3 eg) were mixed together in anisole (5 mL). The reaction mixture was degased 3× with nitrogen, then heated at 90° C. under latm of CO for 18 hours. The crude reaction mixture was concentrated under high vacuum and the residue was chromatographed with 30% EtOAc/hexane to give the title compound. | CSc1ccc(C(=O)c2ccc([C@H](O[C@@H](CC(C)C)C(=O)NCC#N)c3ccccc3)cc2)cc1 | null | CSc1ccc(B(O)O)cc1 | CC(C)C[C@H](O[C@H](c1ccccc1)c1ccc(Br)cc1)C(=O)NCC#N | O=C([O-])[O-] | Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:9][C@@H:10]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:11]([NH:13][CH2:14][C:15]#[N:16])=[O:12])=[CH:4][CH:3]=1.[CH3:27][S:28][C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1.[I-].[K+].[C:40](=O)([O-])[O-:41].[K+].[K+]>C1(OC)C=CC=CC=1>[C:15]([CH2:14][NH:13][C:11](=[O:12])[C@@H:10]([O:9][C@@H:8]([C:5]1[CH:6]=[CH:7][C:2]([C:40](=[O:41])[C:32]2[CH:33]=[CH:34][C:29]([S:28][CH3:27])=[CH:30][CH:31]=2)=[CH:3][CH:4]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:17][CH:18]([CH3:20])[CH3:19])#[N:16] | null | COc1ccccc1 | 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 | null |
904,492 | Cl | [BH4-] | [Na+] | null | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | 2009-01-01T00:09:00 | true | (1R,2S)-2-Amino-cyclopentanecarboxylic acid methyl ester hydrochloride (prepared as described in Example 11a, 0.2 g, 1.27 mmol) was dissolved in methanol (5.5 mL), followed by addition of 4-fluoro-3-chlorobenzaldehyde (0.201 g, 1.27 mmol) and stirred at 25° C. for 10 min. After this time, 5.2 M acetic acid (0.245 mL) was added, stirred at 25° C. for 5 min before placing in an ice-bath. Once at 0° C., sodium borohydride (0.203 mg, 3.2 mmol) was added portionwise after which time the mixture was allowed to warm to 25° C. and continued to stir for 17 h. The reaction mixture was quenched by pouring into saturated aqueous sodium bicarbonate solution (200 mL) and extracted with ethyl acetate (200 mL). The organic layer was concentrated in vacuo and purified by flash column chromatography (Teledyne Isco RediSep Flash Column; 0-80% ethyl acetate in hexanes) to afford the desired product, (1R,2S)-2-(3-chloro-4-fluoro-benzylamino)-cyclopentanecarboxylic acid methyl ester (256 mg, 0.898 mmol, 70% as a yellow oil, containing residual ethyl acetate. 1H NMR (400 MHz, CDCl3) δ: 1.55-1.97 (m, 6H), 2.86 (dd, 1H, J1=14.2 Hz, J2=7.0 Hz), 3.19 (dd, 1H, J1=13.1 Hz, J2=6.9 Hz), 3.62 (s, 3H), 3.64 (d, 2H, J=6.2 Hz), 6.96 (t, 1H, J=8.5 Hz), 7.04-7.08 (m, 1H), 7.26-7.28 (m, 1H). LC-MS (ESI) calcd for C14H17ClFNO2 285.09, found 286.0 [M+H+]. | COC(=O)[C@@H]1CCC[C@@H]1NCc1ccc(F)c(Cl)c1 | null | COC(=O)[C@@H]1CCC[C@@H]1N | O=Cc1ccc(F)c(Cl)c1 | null | Cl.[CH3:2][O:3][C:4]([C@@H:6]1[CH2:10][CH2:9][CH2:8][C@@H:7]1[NH2:11])=[O:5].[F:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][C:14]=1[Cl:21].C(O)(=O)C.[BH4-].[Na+]>CO>[CH3:2][O:3][C:4]([C@@H:6]1[CH2:10][CH2:9][CH2:8][C@@H:7]1[NH:11][CH2:17][C:16]1[CH:19]=[CH:20][C:13]([F:12])=[C:14]([Cl:21])[CH:15]=1)=[O:5] | 0.17 | CO | CC(=O)O | null | 25 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,207,318 | null | null | null | null | ord_dataset-fb72428f30234761b4216139dc228d0c | 2012-01-01T00:09:00 | true | Following the general method as outlined in Example 37, starting from tert-butyl(4-cyano-2-ethynyl phenoxy)acetate (Intermediate 46) and 3-[(3-bromo-4-methylphenyl)sulfonyl]propan-1-ol (Intermediate 68), the title compound was obtained as an off-white solid. | Cc1ccc(S(=O)(=O)CCCO)cc1C#Cc1cc(C#N)ccc1OCC(=O)O | null | C#Cc1cc(C#N)ccc1OCC(=O)OC(C)(C)C | Cc1ccc(S(=O)(=O)CCCO)cc1Br | null | C([O:5][C:6](=[O:19])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][C:10]=1[C:17]#[CH:18])(C)(C)C.Br[C:21]1[CH:22]=[C:23]([S:28]([CH2:31][CH2:32][CH2:33][OH:34])(=[O:30])=[O:29])[CH:24]=[CH:25][C:26]=1[CH3:27]>>[C:15]([C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:7][C:6]([OH:5])=[O:19])=[C:10]([C:17]#[C:18][C:21]2[CH:22]=[C:23]([S:28]([CH2:31][CH2:32][CH2:33][OH:34])(=[O:30])=[O:29])[CH:24]=[CH:25][C:26]=2[CH3:27])[CH:11]=1)#[N:16] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
13,670 | Cl | null | null | null | ord_dataset-7f88a5da29d74264aae5239be74b3981 | 1976-01-01T00:10:00 | true | To ten grams of 2-amino-3-(p-chlorophenyl)-1-methylindole hydrochloride in 80 ml. of pyridine, 5.4 ml. acetic anhydride are added under stirring at 20°-25° C. After five hours the pyridine is distilled off in vacuo at 40°-45° C and the oily residue solidifies with water. The product is crystallized from methanol. Yield 7.9 g. M.p. 196°-197° C. | CC(=O)Nc1c(-c2ccc(Cl)cc2)c2ccccc2n1C | null | Cn1c(N)c(-c2ccc(Cl)cc2)c2ccccc21 | CC(=O)OC(C)=O | null | Cl.[NH2:2][C:3]1[N:4]([CH3:19])[C:5]2[C:10]([C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:20](OC(=O)C)(=[O:22])[CH3:21]>N1C=CC=CC=1>[C:20]([NH:2][C:3]1[N:4]([CH3:19])[C:5]2[C:10]([C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)(=[O:22])[CH3:21] | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,403,195 | [K+] | [OH-] | null | null | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | 2014-01-01T00:03:00 | true | A solution of ethyl 7-aminothieno[2,3-b]pyrazine-6-carboxylate 7 (10 g, 44.8 mmol) and potassium hydroxide (5.0 g, 90 mmol) in THF (50 mL), ethanol (50 mL) and water (20 mL) was stirred at 70° C. for 2 h. Quenched in a cold solution of 2N HCl, and the resulting precipitate was collected to give crude 7-aminothieno[2,3-b]pyrazine-6-carboxylic acid 8 (8.59 g, 98%). 1H-NMR (400 MHz, DMSO-d6) 7.03 (br s, 2H), 8.77 (s, 2H), 12.8 (br s, 1H). | Nc1c(C(=O)O)sc2nccnc12 | null | CCOC(=O)c1sc2nccnc2c1N | null | null | [NH2:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][N:9]=2)[S:4][C:3]=1[C:11]([O:13]CC)=[O:12].[OH-].[K+]>C1COCC1.C(O)C.O>[NH2:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][N:9]=2)[S:4][C:3]=1[C:11]([OH:13])=[O:12] | null | CCO | C1CCOC1 | O | null | null | 98.2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,300,548 | null | null | null | null | ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c | 2013-01-01T00:05:00 | true | 55 mg of 3-(2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)benzenamine was reacted with N,N-dimethylglycine via General Procedure I to give N-(3-(2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)phenyl)-2-(dimethylamino)acetamide. 70 mg of the crude N-(3-(2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)phenyl)-2-(dimethylamino)acetamide was coupled to 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole 7 via General Procedure A. The product was purified by reverse phase HPLC to yield 3 mg of 152. MS (Q1) 514 (M)+. | CN(C)CC(=O)Nc1cccc(-c2cc3nc(Cl)nc(N4CCOCC4)c3s2)c1 | null | CN(C)CC(=O)O | Nc1cccc(-c2cc3nc(Cl)nc(N4CCOCC4)c3s2)c1 | null | [Cl:1][C:2]1[N:3]=[C:4]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[C:5]2[S:10][C:9]([C:11]3[CH:12]=[C:13]([NH2:17])[CH:14]=[CH:15][CH:16]=3)=[CH:8][C:6]=2[N:7]=1.[CH3:24][N:25]([CH3:30])[CH2:26][C:27](O)=[O:28]>>[Cl:1][C:2]1[N:3]=[C:4]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[C:5]2[S:10][C:9]([C:11]3[CH:12]=[C:13]([NH:17][C:27](=[O:28])[CH2:26][N:25]([CH3:30])[CH3:24])[CH:14]=[CH:15][CH:16]=3)=[CH:8][C:6]=2[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 |
987,349 | Cl | [K+] | [OH-] | null | ord_dataset-35b56288528641309a040cc2b6710b61 | 2010-01-01T00:08:00 | true | To a solution of (2R*,4S*)-4-{[3,5-bis(trifluoromethyl)benzyl]-[5-(4-ethoxycarbonylpiperidin-1-yl)pyrimidin-2-yl]}amino-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (245 mg) in ethanol (2 ml) is added aqueous 2N-potassium hydroxide solution (0.332 ml) and the mixture is heated under reflux at 50° C. for 1 hour. The reaction solution is diluted with ethyl acetate and acidified with 1N-hydrochloric acid. The organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by column chromatography (silica gel; chloroform to chloroform:methanol=90:10) to give (2R*,4S*)-4-{[3,5-bis(trifluoromethyl)benzyl]-[5-(4-carboxypiperidin-1-yl) pyrimidin-2-yl]}amino-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (210 mg). MS (m/z): 711 [M+H]+. | CCOC(=O)N1c2ccc(OC)nc2[C@@H](Nc2ncc(N3CCC(C(=O)O)CC3)c(Cc3cc(C(F)(F)F)cc(C(F)(F)F)c3)n2)C[C@H]1CC | null | CCOC(=O)C1CCN(c2cnc(N[C@H]3C[C@@H](CC)N(C(=O)OCC)c4ccc(OC)nc43)nc2Cc2cc(C(F)(F)F)cc(C(F)(F)F)c2)CC1 | null | null | [CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[N:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=2)[C@@H:9]([NH:18][C:19]2[N:24]=[C:23]([CH2:25][C:26]3[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[C:28]([C:36]([F:39])([F:38])[F:37])[CH:27]=3)[C:22]([N:40]3[CH2:45][CH2:44][CH:43]([C:46]([O:48]CC)=[O:47])[CH2:42][CH2:41]3)=[CH:21][N:20]=2)[CH2:8][C@H:7]1[CH2:51][CH3:52])=[O:5])[CH3:2].[OH-].[K+].Cl>C(O)C.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[N:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=2)[C@@H:9]([NH:18][C:19]2[N:24]=[C:23]([CH2:25][C:26]3[CH:31]=[C:30]([C:32]([F:33])([F:34])[F:35])[CH:29]=[C:28]([C:36]([F:37])([F:38])[F:39])[CH:27]=3)[C:22]([N:40]3[CH2:41][CH2:42][CH:43]([C:46]([OH:48])=[O:47])[CH2:44][CH2:45]3)=[CH:21][N:20]=2)[CH2:8][C@H:7]1[CH2:51][CH3:52])=[O:5])[CH3:2] | null | CCO | CCOC(C)=O | null | 50 | 89.1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,721,304 | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [Na+] | null | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | 2016-01-01T00:05:00 | true | Following the procedure for 1, 5 (4.84 g, 13.1 mmol), 5-bromo-2-iodopyridine (3.72 g, 13.1 mmol), tetrakis(triphenylphosphine)palladium(0) (0.757 g, 0.655 mmol), Na2CO3 (4.97 g, 46.9 mmol), H2O (45 mL) and THF (75 mL) yielded 6 (4.73 g, 90% yield) as a colorless solid after flash chromatography (SiO2, 1:1 hexanes-dichloromethane) and subsequent trituration with EtOAc. | Brc1ccc(-c2ccc(-n3c4ccccc4c4ccccc43)cc2)nc1 | null | CC1(C)OB(c2ccc(-n3c4ccccc4c4ccccc43)cc2)OC1(C)C | Brc1ccc(I)nc1 | null | CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[C:27]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:21]4[C:16]3=[CH:17][CH:18]=[CH:19][CH:20]=4)=[CH:11][CH:10]=2)O1.[Br:29][C:30]1[CH:31]=[CH:32][C:33](I)=[N:34][CH:35]=1.C([O-])([O-])=O.[Na+].[Na+].O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(C)=O.C1COCC1>[Br:29][C:30]1[CH:31]=[CH:32][C:33]([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=4[C:22]4[C:27]3=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:11][CH:10]=2)=[N:34][CH:35]=1 | null | O | C1CCOC1 | CCOC(C)=O | null | null | 90.4 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,728,316 | CC(C)(C)ON=O | null | null | null | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | 2016-01-01T00:05:00 | true | To a solution of 4-(4-amino-2-bromophenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (0.095 g, 0.162 mmol) in dry acetonitrile (1.617 mL) at 0° C. was added tert-butyl nitrite (0.027 mL, 0.226 mmol), followed by dropwise addition of azidotrimethylsilane (0.026 mL, 0.194 mmol). The resulting mixture was stirred for 20 minutes at RT. The reaction was concentrated under a vacuum, and purified via silica gel MPLC, eluting with a gradient of 0% to 100% ethyl acetate in heptanes to provide 4-(4-azido-2-bromophenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide as tan solid. The material was taken up in DCM (1.5 mL), and TFA (0.125 mL, 1.617 mmol) was added. The reaction was stirred at RT for 1.5 h, after which the reaction was concentrated under a vacuum. The material was purified by reverse-phase preparative HPLC using a Phenomenex Luna column, 5 micron, C18(2), 100 Å, 150×30 mm, 0.1% TFA in CH3CN/H2O, gradient 30% to 90% over 20 min to provide 4-(4-azido-2-bromophenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide 2,2,2-trifluoroacetate (0.0308 g, 0.051 mmol) as a tan solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.55-3.63 (m, 1 H) 3.64-3.72 (m, 1 H) 4.27-4.34 (m, 1 H) 4.35-4.41 (m, 1 H) 6.10 (d, J=8.41 Hz, 1 H) 6.78 (d, J=4.69 Hz, 1H) 7.08-7.15 (m, 2 H) 7.22 (d, J=4.60 Hz, 1 H) 7.28 (dd, J=8.51, 2.54 Hz, 1 H) 7.53 (d, J=8.51 Hz, 1 H) 7.56 (d, J=2.54 Hz, 1 H) 12.55 (br. s., 1 H). m/z (ESI) 493.0 (M+H)+. | COc1ccc(CN(c2nccs2)S(=O)(=O)c2ccc3c(c2)OCCN3c2ccc(N=[N+]=[N-])cc2Br)cc1 | null | COc1ccc(CN(c2nccs2)S(=O)(=O)c2ccc3c(c2)OCCN3c2ccc(N)cc2Br)cc1 | C[Si](C)(C)N=[N+]=[N-] | null | [NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][O:11][C:10]3[CH:14]=[C:15]([S:18]([N:21]([CH2:27][C:28]4[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=4)[C:22]4[S:23][CH:24]=[CH:25][N:26]=4)(=[O:20])=[O:19])[CH:16]=[CH:17][C:9]2=3)=[C:4]([Br:36])[CH:3]=1.N(OC(C)(C)C)=O.[N:44]([Si](C)(C)C)=[N+:45]=[N-]>C(#N)C>[N:1]([C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][O:11][C:10]3[CH:14]=[C:15]([S:18]([N:21]([CH2:27][C:28]4[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=4)[C:22]4[S:23][CH:24]=[CH:25][N:26]=4)(=[O:20])=[O:19])[CH:16]=[CH:17][C:9]2=3)=[C:4]([Br:36])[CH:3]=1)=[N+:44]=[N-:45] | 0.33 | CC#N | 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 |
1,549,199 | null | null | null | null | ord_dataset-cac8df8aff894288876df4e093c9877f | 2015-01-01T00:02:00 | true | This compound was prepared in a manner according to 4-(2-methyl-6-phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzaldehyde by using 3-cyclopropyl-1H-pyrazol-5 amine in the first step. | O=Cc1ccc(-c2nc3cc(C4CC4)nn3cc2-c2ccccc2)cc1 | null | Cc1cc2nc(-c3ccc(C=O)cc3)c(-c3ccccc3)cn2n1 | Nc1cc(C2CC2)n[nH]1 | null | [CH3:1][C:2]1[CH:24]=[C:5]2[N:6]=[C:7]([C:16]3[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=3)[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:9][N:4]2[N:3]=1.[CH:25]1(C2C=C(N)NN=2)C[CH2:26]1>>[CH:1]1([C:2]2[CH:24]=[C:5]3[N:6]=[C:7]([C:16]4[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=4)[C:8]([C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=4)=[CH:9][N:4]3[N:3]=2)[CH2:26][CH2:25]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 |
317,184 | null | null | null | null | ord_dataset-eb32c2b9cbdf4fc39ce6c9fe0fa11430 | 1995-01-01T00:10:00 | true | 2-bromo-4-isopropylaniline and 4-chlorobenzene boronic acid were combined to form 2-(4-chlorophenyl)-4-isopropylaniline, and | CC(C)c1ccc(N)c(-c2ccc(Cl)cc2)c1 | null | CC(C)c1ccc(N)c(Br)c1 | OB(O)c1ccc(Cl)cc1 | null | Br[C:2]1[CH:8]=[C:7]([CH:9]([CH3:11])[CH3:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[Cl:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1>>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:2]2[CH:8]=[C:7]([CH:9]([CH3:11])[CH3:10])[CH:6]=[CH:5][C:3]=2[NH2:4])=[CH:15][CH:14]=1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,002,450 | COC(=O)N=C(SC)C(=Nc1ccc(-c2noc(C)n2)cc1)c1cc(OC)cc(OCCO[Si](C)(C)C(C)(C)C)c1F | null | null | null | ord_dataset-70899a0178cc441482746c093624afa0 | 2010-01-01T00:10:00 | true | The same procedure was carried out as in Examples (200b) to (200c), except that [2-(5-fluoro-8-methoxychroman-6-yl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene]carbamic acid methyl ester (Example (33d)) and 0.1% trifluoroacetic acid were used instead of respectively the (2-{3-[2-(t-butyldimethylsilanyloxy)ethoxy]-2-fluoro-5-methoxyphenyl}-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene)carbamic acid methyl ester in Example (200b) and 0.1% acetic acid in Example (200c), to give the title compound. | COc1cc(C(Nc2ccc(C(=N)N)cc2)c2nn(-c3ncccc3N)c(=O)[nH]2)c(F)c2c1OCCC2 | null | COC(=O)N=C(SC)C(=Nc1ccc(-c2noc(C)n2)cc1)c1cc(OC)c2c(c1F)CCCO2 | COc1cc(OCCO)c(F)c(C(Nc2ccc(C(=N)N)cc2)c2nn(-c3ncccc3N)c(=O)[nH]2)c1 | null | C(O)(=O)C.[NH2:5][C:6]1[C:7]([N:12]2[C:16](=[O:17])[NH:15][C:14]([CH:18]([NH:32][C:33]3[CH:41]=[CH:40][C:36]([C:37]([NH2:39])=[NH:38])=[CH:35][CH:34]=3)[C:19]3[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[C:21](OCCO)[C:20]=3[F:31])=[N:13]2)=[N:8][CH:9]=[CH:10][CH:11]=1.COC(=O)N=C(SC)C(C1C(F)=C2C(=C(OC)C=1)[O:67][CH2:66][CH2:65][CH2:64]2)=NC1C=CC(C2N=C(C)ON=2)=CC=1.[F:77][C:78]([F:83])([F:82])[C:79]([OH:81])=[O:80].COC(=O)N=C(SC)C(C1C=C(OC)C=C(OCCO[Si](C(C)(C)C)(C)C)C=1F)=NC1C=CC(C2N=C(C)ON=2)=CC=1>C(O)(=O)C>[F:77][C:78]([F:83])([F:82])[C:79]([OH:81])=[O:80].[NH2:5][C:6]1[C:7]([N:12]2[C:16](=[O:17])[NH:15][C:14]([CH:18]([NH:32][C:33]3[CH:41]=[CH:40][C:36]([C:37]([NH2:39])=[NH:38])=[CH:35][CH:34]=3)[C:19]3[C:20]([F:31])=[C:21]4[C:22](=[C:23]([O:25][CH3:26])[CH:24]=3)[O:67][CH2:66][CH2:65][CH2:64]4)=[N:13]2)=[N:8][CH:9]=[CH:10][CH:11]=1 | null | O=C(O)C(F)(F)F | 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 |
54,556 | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | ord_dataset-053897d9b1744303b2fdfe3e796ca27b | 1979-01-01T00:04:00 | true | 1 g. of 3-(3',4'-dichloro-4-biphenylyl)-3-hydroxybutyric acid and 0.1 g. of p-toluenesulfonic acid in 35 ml. of toluene are heated under reflux for 3 hours and water by-product is removed. The reaction mixture is worked up to give 3-(3',4'-dichloro-4-biphenylyl)-2-butenoic acid. | CC(=CC(=O)O)c1ccc(-c2ccc(Cl)c(Cl)c2)cc1 | null | CC(O)(CC(=O)O)c1ccc(-c2ccc(Cl)c(Cl)c2)cc1 | null | null | [Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([C:15](O)([CH3:20])[CH2:16][C:17]([OH:19])=[O:18])=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([CH3:20])=[CH:16][C:17]([OH:19])=[O:18])=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8] | null | 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 | null |
480,967 | null | null | null | null | ord_dataset-21c1b1c06c7e4e09a38b5b1c71a32e52 | 2000-01-01T00:10:00 | true | 1-(5-Amino-2,4-difluorophenyl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (150 mg), 3-amino-1-propanol (75 mg) and triethylamine (200 mg) were added to pyridine (350 mg), and the mixture was stirred at 45° C. for 43 hours. The reaction mixture was concentrated under reduced pressure. A process of adding ethanol (2 ml) to the residue and then concentrating the mixture under reduced pressure was conducted twice repeatedly. Concentrated hydrochloric acid (120 mg) was added to the residue, and the mixture was concentrated under reduced pressure. Ethanol (1 ml) was added to the resultant residue, and deposits were collected by filtration and washed with ethanol and diisopropyl ether in that order to obtain the title compound (80 mg) as a colorless powder. | Nc1cc(-n2cc(C(=O)O)c(=O)c3cc(F)c(NCCCO)c(Cl)c32)c(F)cc1F | null | NCCCO | Nc1cc(-n2cc(C(=O)O)c(=O)c3cc(F)c(F)c(Cl)c32)c(F)cc1F | null | [NH2:1][C:2]1[C:3]([F:26])=[CH:4][C:5]([F:25])=[C:6]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([F:20])=[C:15](F)[C:16]=3[Cl:18])[C:11](=[O:21])[C:10]([C:22]([OH:24])=[O:23])=[CH:9]2)[CH:7]=1.[NH2:27][CH2:28][CH2:29][CH2:30][OH:31].C(N(CC)CC)C>N1C=CC=CC=1>[NH2:1][C:2]1[C:3]([F:26])=[CH:4][C:5]([F:25])=[C:6]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([F:20])=[C:15]([NH:27][CH2:28][CH2:29][CH2:30][OH:31])[C:16]=3[Cl:18])[C:11](=[O:21])[C:10]([C:22]([OH:24])=[O:23])=[CH:9]2)[CH:7]=1 | 43 | CCN(CC)CC | c1ccncc1 | null | 45 | 46.7 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,263,421 | Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1 | [Cu]I | null | null | ord_dataset-266f60b4555945d6afb2d2bdf5fa04e0 | 2013-01-01T00:02:00 | true | To a degassed solution of 1.3 mL DMF at room temperature containing (S)-5-ethynyl-N-[methyl(oxo)phenyl-λ6-sulfanylidene]nicotinamide (63 mg, 0.22 mmol), 4-iodophenol (121 mg, 0.55 mmol), and triethylamine (0.09 mL, 0.66 mmol) was added dichlorobis(triphenylphosphine)palladium(II) (15 mg, 0.022 mmol) and copper(I)iodide (4 mg, 0.022 mmol). After proceeding for 1 hour the reaction was partitioned between EtOAc and H2O. The mixture was filtered to remove an insoluble brown precipitate and the EtOAc layer was washed with H2O, brine, dried with anhydrous Na2SO4 and rotary evaporated. The brown film was chromatographed eluting with CHCl3/EtOAc to give a yellow solid which was recrystallized from CHCl3/hexane to give the title compound as an off-white solid (38 mg, 45%). | C[S@@](=O)(=NC(=O)c1cncc(C#Cc2ccc(O)cc2)c1)c1ccccc1 | null | Oc1ccc(I)cc1 | C#Cc1cncc(C(=O)N=[S@@](C)(=O)c2ccccc2)c1 | null | [C:1]([C:3]1[CH:4]=[N:5][CH:6]=[C:7]([CH:20]=1)[C:8]([N:10]=[S@@:11]([CH3:19])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])#[CH:2].I[C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1.C(N(CC)CC)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.CN(C=O)C>[OH:28][C:25]1[CH:26]=[CH:27][C:22]([C:2]#[C:1][C:3]2[CH:4]=[N:5][CH:6]=[C:7]([CH:20]=2)[C:8]([N:10]=[S@@:11]([CH3:19])(=[O:18])[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:9])=[CH:23][CH:24]=1 | 1 | CCN(CC)CC | CN(C)C=O | null | null | null | 45.9 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
968,644 | CN(C)c1ccncc1 | null | null | null | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | 2010-01-01T00:06:00 | true | Isobutyryl chloride (10.4 mL, 98.04 mmol) was added drop wise to a stirred and a cooled (0° C.) solution of the product of Example 5E (61.28 mmol), diisopropylethyl amine (21.3 mL, 122.56 mmol), and 4-dimethylaminopyridine (0.30 g, 3.0 mmol) in dry dichloromethane (150 mL). The resulting solution was allowed to stir at 0° C. for five hours. After the completion of reaction (monitored by TLC), methanol (5 mL) was added to quench excess acid chloride. The solvent was removed under reduced pressure and the resulting slurry was partitioned using diethyl ether (200 mL) and saturated NH4Cl (100 mL). The organic layer was washed successively with 20% NaHSO4, NaHCO3, brine, and it was dried over MgSO4. After removal of solvent, the crude oil was purified over silica gel column using 10% diethyl ether in hexanes to give the title compound as a colorless oil: (20.5 g, 84% over 2 steps). | CC(C)C(=O)OCC=CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C | null | CC(C)C(=O)Cl | CC(C)(C)[Si](OCC=CCO)(c1ccccc1)c1ccccc1 | null | [C:1](Cl)(=[O:5])[CH:2]([CH3:4])[CH3:3].[C:7]([Si:11]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[O:12][CH2:13][CH:14]=[CH:15][CH2:16][OH:17])([CH3:10])([CH3:9])[CH3:8].C(N(C(C)C)CC)(C)C.CO>CN(C)C1C=CN=CC=1.ClCCl>[C:7]([Si:11]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[O:12][CH2:13][CH:14]=[CH:15][CH2:16][O:17][C:1](=[O:5])[CH:2]([CH3:4])[CH3:3])([CH3:10])([CH3:8])[CH3:9] | null | CCN(C(C)C)C(C)C | CO | ClCCl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
595,654 | null | null | null | null | ord_dataset-843ef38b45484f72826f5f39d8a29c4d | 2003-01-01T00:06:00 | true | (3S) 3-(1-Fluorenylmethoxycarbonylamino)-4-oxobutyric acid tert-butyl ester semicarbazone (4; 226 mg, 0.5 mmol; prepared in a similar manner as the benzyloxycarbonyl analog described in Graybill et al. Int. J. Protein Res., 44, pp. 173-82 (1994)) was dissolved in 10 ml of acetonitrile (20 ml) and diethylamine (2 ml) was added to the solution. The reaction was stirred for two hours, concentrated in vacuo, the resulting dissolved in acetonitrile and concentrated in vacuo again to give (3S) 3-amino-4-oxobutyric acid tert-butyl ester semicarbazone. A 5° C. solution of the semicarbazone and 3 (188 mg, 0.424 mmol) in methylene chloride/DMF (6 ml of 1:1) was treated with 1-hydroxybenzotriazole (HOBt; 57 mg, 0.424 mmol) and 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (EDC; 115 mg, 0.6 mmol) and the reaction was stirred at room temperature for 16 hr. The reaction was diluted with ethyl acetate (100 ml) and washed with water, aqueous saturated NaHCO3 and aqueous saturated NaCl, dried over dried over anhydrous Na2SO4 and concentrated in vacuo. Chromatography (SiO2, 5% ammonium hydroxide/5% methanol/methylene chloride eluent) gave 250 mg of 5. | CC(C)(C)OC(CC(N)C=O)=NNC(N)=O | null | CC(C)(C)OC(CC(C=O)NC(=O)OCc1cccc2c1Cc1ccccc1-2)=NNC(N)=O | null | null | [C:1]([O:5][C:6](=[N:29][NH:30][C:31]([NH2:33])=[O:32])[CH2:7][CH:8]([NH:11]C(OCC1C2CC3C(=CC=CC=3)C=2C=CC=1)=O)[CH:9]=[O:10])([CH3:4])([CH3:3])[CH3:2].C(NCC)C>C(#N)C>[C:1]([O:5][C:6](=[N:29][NH:30][C:31]([NH2:33])=[O:32])[CH2:7][CH:8]([NH2:11])[CH:9]=[O:10])([CH3:4])([CH3:2])[CH3:3] | 2 | CC#N | CCNCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
102,737 | null | null | null | null | ord_dataset-bdb961f26fac426eaa2de8f54a284acf | 1983-01-01T00:02:00 | true | A mixture of 8.8 g of 7,7,9,9-tetramethyl-1,4-dioxa-8-azaspiro[4.5]decane and 7.0 g of 2,2-bis[4-(2,3-epoxypropoxy)cyclohexyl]propane was heated at 120° C. for 30 hours. After completion of the reaction, the reaction mixture was purified by column chromatography through silica gel eluted with ethyl acetate. The desired Compound No. 207 was obtained in the form of a pale yellow oil which after being kept at ambient temperature, turned to a solid melting at 48°-50° C. | CC(C)(C1CCC(OCC(O)CN2C(C)(C)CC3(CC2(C)C)OCCO3)CC1)C1CCC(OCC(O)CN2C(C)(C)CC3(CC2(C)C)OCCO3)CC1 | null | CC(C)(C1CCC(OCC2CO2)CC1)C1CCC(OCC2CO2)CC1 | CC1(C)CC2(CC(C)(C)N1)OCCO2 | null | [CH3:1][C:2]1([CH3:14])[NH:11][C:10]([CH3:13])([CH3:12])[CH2:9][C:4]2([O:8][CH2:7][CH2:6][O:5]2)[CH2:3]1.[O:15]1[CH2:39][CH:16]1[CH2:17][O:18][CH:19]1[CH2:24][CH2:23][CH:22]([C:25]([CH:28]2[CH2:33][CH2:32][CH:31]([O:34][CH2:35][CH:36]3[O:38][CH2:37]3)[CH2:30][CH2:29]2)([CH3:27])[CH3:26])[CH2:21][CH2:20]1>>[OH:15][CH:16]([CH2:39][N:11]1[C:10]([CH3:13])([CH3:12])[CH2:9][C:4]2([O:5][CH2:6][CH2:7][O:8]2)[CH2:3][C:2]1([CH3:14])[CH3:1])[CH2:17][O:18][CH:19]1[CH2:20][CH2:21][CH:22]([C:25]([CH:28]2[CH2:29][CH2:30][CH:31]([O:34][CH2:35][CH:36]([OH:38])[CH2:37][N:11]3[C:2]([CH3:14])([CH3:1])[CH2:3][C:4]4([O:5][CH2:6][CH2:7][O:8]4)[CH2:9][C:10]3([CH3:13])[CH3:12])[CH2:32][CH2:33]2)([CH3:27])[CH3:26])[CH2:23][CH2:24]1 | null | null | null | null | 120 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
824,922 | null | null | null | null | ord_dataset-0ca5627a13c049a99463095023b09fe5 | 2008-01-01T00:06:00 | true | Heat a mixture of (S)-2-(2-oxoethyl)-piperazine-1,4-dicarboxylic acid di-tert-butyl ester (1.38 g, 4.21 mmol) and (carbethoxymethylene)triphenylphosphorane (1.87 g, 5.38 mmol) in THF (17 mL) at reflux for 4 h. Concentrate the mixture under reduced pressure and purify by silica gel chromatography eluting with 20% to 50% EtOAc in hexanes. Combine the purified fractions, concentrate under reduced pressure, azeotrope with CH2Cl2/hexanes (1:2) and place under vacuum to give the title compound: yellow tar (0.961 g), mass spectrum (m/e): 416.09(M+NH4). | CCOC(=O)C=CC[C@H]1CN(C(=O)OC(C)(C)C)CCN1C(=O)OC(C)(C)C | null | CC(C)(C)OC(=O)N1CCN(C(=O)OC(C)(C)C)[C@@H](CC=O)C1 | C1CCOC1 | CCOC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1 | [C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][C@@H:9]1CC=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:24]([CH:29]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:26][CH2:27][CH3:28])=[O:25].[CH2:49]1COC[CH2:50]1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[CH2:10][C@@H:9]1[CH2:49][CH:50]=[CH:29][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[O:7])([CH3:3])([CH3:4])[CH3:2] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,511,386 | NN | null | null | null | ord_dataset-1a1aa5d1c3224edca0aec6e3398da985 | 2014-01-01T00:11:00 | true | The product of Step D (0.72 g, 1.41 mmol) was dissolved in methanol (4 mL) and tetrahydrofuran (4 mL). To the resulting solution was added hydrazine (2 mL, 60 mmol). The solution was stirred at 50° C. for 2 h. The reaction mixture was concentrated under reduced pressure and the residue was purified by combi-flash chromatography eluting with MeOH/EtOAc (20-60%). The product was further purified by prep.-LC/MS (pH=10). The purification afforded 210 mg (39.0% yield) of the final product as a white solid. LC/MS found: 383.1 (M+1)+; 1H NMR (300 MHz, DMSO-d6) δ: 7.9 (d, J=13.8 Hz, 2H), 7.58 (dd, J1=7.9 Hz, J2=1.1 Hz, 1H), 7.48 (d, J=1.9 Hz, 1H), 6.96 (m, 3H), 6.45 (d, J=1.9 Hz, 1H), 4.47 (s, 2H), 4.41 (m, 1H), 3.86 (s, 3H), 3.04 (dd, J1=14.3 Hz, J2=4.8 Hz, 1H), 2.89 (dd, J1=14.0 Hz, J2=3.9 Hz, 1H), 2.85 (d, J=6.80 Hz, 2H). | Cn1nccc1-c1ccc2c(c1)CN([C@H](CN)Cc1cc(F)cc(F)c1)C2=O | null | Cn1nccc1-c1ccc2c(c1)CN([C@@H](Cc1cc(F)cc(F)c1)CN1C(=O)c3ccccc3C1=O)C2=O | null | null | [CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[C:12](=[O:16])[N:11]([C@@H:17]([CH2:30][C:31]2[CH:36]=[C:35]([F:37])[CH:34]=[C:33]([F:38])[CH:32]=2)[CH2:18][N:19]2C(=O)C4C(=CC=CC=4)C2=O)[CH2:10]3)=[CH:5][CH:4]=[N:3]1.NN>CO.O1CCCC1>[NH2:19][CH2:18][C@@H:17]([N:11]1[CH2:10][C:9]2[C:13](=[CH:14][CH:15]=[C:7]([C:6]3[N:2]([CH3:1])[N:3]=[CH:4][CH:5]=3)[CH:8]=2)[C:12]1=[O:16])[CH2:30][C:31]1[CH:32]=[C:33]([F:38])[CH:34]=[C:35]([F:37])[CH:36]=1 | 2 | C1CCOC1 | CO | null | 50 | null | 38.9 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
92,662 | [Na+] | [OH-] | null | null | ord_dataset-dba7c8cf38834984ba5e6376158f46fe | 1982-01-01T00:03:00 | true | 3-(4-Chlorophenyl)-5-aminoisoxazole (1 gram) and 2,6-dichlorobenzoylchloride (5 grams) were placed in a 100 ml. reaction vessel and heated to near reflux for 11/2 hours. The mixture was then cooled to room temperature and treated with 25 ml. of 2 N NaOH and 25 ml. ethanol. After refluxing for 2 hours, the ethanol was slowly removed at reduced pressure. A solid precipitate was collected by filtration. The remaining solution was treated with activated charcoal, filtered, and cooled to room temperature. The aqueous solution was extracted with chloroform. The chloroform was washed with water and dried (Na2SO4). Removal of the solvent afforded an oily product which was recrystallized from ether/hexane, m.p. 208°-209° C. | O=C(Nc1cc(-c2ccc(Cl)cc2)no1)c1c(Cl)cccc1Cl | null | Nc1cc(-c2ccc(Cl)cc2)no1 | O=C(Cl)c1c(Cl)cccc1Cl | null | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([NH2:13])[O:10][N:9]=2)=[CH:4][CH:3]=1.[Cl:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:16]=1[C:17](Cl)=[O:18].[OH-].[Na+]>C(O)C>[Cl:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:16]=1[C:17]([NH:13][C:11]1[O:10][N:9]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[CH:12]=1)=[O:18] | null | CCO | null | null | 25 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
149,176 | Cl | null | null | null | ord_dataset-f222e615b1f74f0fabef9cd9b98516b7 | 1986-01-01T00:10:00 | true | A solution of triethylamine (15 g) in chloroform (15 ml) was added dropwise to a stirred mixture of 2-aminopropiophenone hydrochloride (12 g) and chloroform (65 ml) at ice bath temperature in 10 minutes. To the stirred mixture was added dropwise a solution of ethyl chloroformate (8 g) in chloroform (20 ml) under the same conditions and then stirring was continued for 4 hours at ice bath temperature. The solution was evaporated under reduced pressure and the residue was dissolved in a mixture of ethyl acetate and water. The organic layer was separated, washed successively with a saturated aqueous solution of sodium bicarbonate, water, 5% hydrochloric acid, and water, dried over magnesium sulfate, and evaporated under reduced pressure to give an oil containing the object compound. The above obtained product was purified by column chromatography on silica gel (200 g) using a mixture of diisopropyl ether and chloroform (1:4) as an eluent to give an oil of 2-ethoxycarbonylaminopropiophenone (10.48 g). | CCOC(=O)NC(C)C(=O)c1ccccc1 | null | CCOC(=O)Cl | CC(N)C(=O)c1ccccc1 | null | C(N(CC)CC)C.Cl.[NH2:9][CH:10]([CH3:19])[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:12].Cl[C:21]([O:23][CH2:24][CH3:25])=[O:22]>C(Cl)(Cl)Cl>[CH2:24]([O:23][C:21]([NH:9][CH:10]([CH3:19])[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:12])=[O:22])[CH3:25] | 4 | CCN(CC)CC | ClC(Cl)Cl | null | null | 73.3 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,542,955 | CN(C)C(On1nnc2ccccc21)=[N+](C)C | F[P-](F)(F)(F)(F)F | O=S(=O)(O)O | null | ord_dataset-cac8df8aff894288876df4e093c9877f | 2015-01-01T00:02:00 | true | 0.15 g (0.45 mmol) of 2-[(isoquinoline-3-carbonyl)-amino]-1H-benzoimidazole-5-carboxylic acid was reacted with 0.26 g (0.68 mmol) of HBTU and 0.06 g (0.45 mmol) of 2-aminoimidazole sulfate in 3.0 mL of DMF and 1.0 mL of DIEA as described in general procedure A. After cooling to room temperature, the reaction mixture was diluted with water, the solid was collected by filtration, dissolved with MeOH and evaporated onto silica gel, and isolated by flash column chromatography (500 mL DCM/20 mL NH3/MeOH) to yield ˜10 mg of the desired isoquinoline-3-carboxylic acid [5-(1H-imidazol-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-amide. LCMS: 398.0 (M+1)+ | O=C(Nc1ncc[nH]1)c1ccc2[nH]c(NC(=O)c3cc4ccccc4cn3)nc2c1 | null | O=C(O)c1ccc2[nH]c(NC(=O)c3cc4ccccc4cn3)nc2c1 | Nc1ncc[nH]1 | null | [CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]([NH:13][C:14]2[NH:18][C:17]3[CH:19]=[CH:20][C:21]([C:23]([OH:25])=O)=[CH:22][C:16]=3[N:15]=2)=[O:12])[N:2]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.S(O)(O)(=O)=O.[NH2:55][C:56]1[NH:57][CH:58]=[CH:59][N:60]=1>CN(C=O)C.CCN(C(C)C)C(C)C.O>[NH:57]1[CH:58]=[CH:59][N:60]=[C:56]1[NH:55][C:23]([C:21]1[CH:20]=[CH:19][C:17]2[NH:18][C:14]([NH:13][C:11]([C:3]3[N:2]=[CH:1][C:10]4[C:5]([CH:4]=3)=[CH:6][CH:7]=[CH:8][CH:9]=4)=[O:12])=[N:15][C:16]=2[CH:22]=1)=[O:25] | null | O | CCN(C(C)C)C(C)C | CN(C)C=O | 25 | null | 5.6 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
210,080 | O=[Cr](=O)([O-])Cl | c1cc[nH+]cc1 | null | null | ord_dataset-e0a818f9350b46cdb184d2ac404ede9f | 1990-01-01T00:06:00 | true | A solution of 5-phenylpent-4-yn-1-ol (250 mg) in dry CH2Cl2 (2 ml) was added to a suspension of pyridinium chlorochromate (520 mg) in dry CH2Cl2 (3 ml). The mixture was stirred for 2.5 hours and diluted with ether, and the organic solution was decanted off. The oily residue was treated with ether (5×20 ml) and the extracts were washed successively with 5% NaHCO3, water and brine. After drying, the solvent was removed to yield 5-phenylpent-4-ynal. | O=CCCC#Cc1ccccc1 | null | OCCCC#Cc1ccccc1 | null | null | [C:1]1([C:7]#[C:8][CH2:9][CH2:10][CH2:11][OH:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl.CCOCC>[C:1]1([C:7]#[C:8][CH2:9][CH2:10][CH:11]=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1 | 2.5 | CCOCC | ClCCl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,571,800 | null | null | null | null | ord_dataset-9741bb5fd93044078df2a45f45733054 | 2015-01-01T00:04:00 | true | The above compound may be made analogous to Example 1 using ethyl 1-(7-fluoro-6-isopropyl-4-oxo-3,4-dihydroquinazolin-2-yl)-1H-pyrazole-4-carboxylate in step D and diethylamine in step E. MS (ESI): predicted mass calcd. for C19H22FN5O2, 371.2 | CCN(CC)c1nc(-n2cc(C(=O)O)cn2)nc2cc(F)c(C(C)C)cc12 | null | CCOC(=O)c1cnn(-c2nc3cc(F)c(C(C)C)cc3c(=O)[nH]2)c1 | CCNCC | null | [F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=O)[NH:7][C:8]([N:12]3[CH:16]=[C:15]([C:17]([O:19]CC)=[O:18])[CH:14]=[N:13]3)=[N:9]2)=[CH:4][C:3]=1[CH:23]([CH3:25])[CH3:24].[CH2:26]([NH:28][CH2:29][CH3:30])[CH3:27]>>[CH2:26]([N:28]([CH2:29][CH3:30])[C:6]1[C:5]2[C:10](=[CH:11][C:2]([F:1])=[C:3]([CH:23]([CH3:24])[CH3:25])[CH:4]=2)[N:9]=[C:8]([N:12]2[CH:16]=[C:15]([C:17]([OH:19])=[O:18])[CH:14]=[N:13]2)[N:7]=1)[CH3:27] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
598,498 | null | null | null | null | ord_dataset-843ef38b45484f72826f5f39d8a29c4d | 2003-01-01T00:06:00 | true | The product from Example 89B and 2-methyl-3-nitroaniline were processed as in Example 6A to provide the title compound. MS (ESI−) m/z 403 (M−H)−. | C=CCOc1cc(C)cc(Oc2ccc(CNc3cccc([N+](=O)[O-])c3C)cc2)c1 | null | C=CCOc1cc(C)cc(Oc2ccc(C=O)cc2)c1 | Cc1c(N)cccc1[N+](=O)[O-] | null | [CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH:17]=[C:18]([CH3:20])[CH:19]=1)[O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=1)[CH:2]=[CH2:3].[CH3:21][C:22]1[C:28]([N+:29]([O-:31])=[O:30])=[CH:27][CH:26]=[CH:25][C:23]=1[NH2:24]>>[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH:17]=[C:18]([CH3:20])[CH:19]=1)[O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][NH:24][C:23]2[CH:25]=[CH:26][CH:27]=[C:28]([N+:29]([O-:31])=[O:30])[C:22]=2[CH3:21])=[CH:11][CH:10]=1)[CH:2]=[CH2:3] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,433,854 | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [Na+] | null | ord_dataset-5e6956e6e8c24a168866a253f4a66c6c | 2014-01-01T00:05:00 | true | A glass microwave reaction vessel was charged with 3-morpholino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-2-amine (0.150 g, 0.422 mmol, prepared as in Example 2, Step 1-2) and 4-chloro-1-(2-iodo-3-methylphenyl)-3-methyl-1H-pyrazole (0.281 g, 0.845 mmol) in dioxane (3 mL) and 2 M aqueous sodium carbonate (1.0 mL, 2.0 mmol). The vessel was capped with a septum and the solution was degassed by bubbling nitrogen gas through the solution for 10 min. Next, Pd (PPh3)4 (0.049 g, 0.042 mmol) was added and the vessel was sealed. The reaction mixture was stirred and heated in a microwave reactor at 140° C. for 15 min. The reaction was poured into water and the mixture was extracted with EtOAc. The combined organic extracts were washed with water, saturated sodium chloride, and dried over sodium sulfate. The solution was filtered and concentrated in vacuo to give the crude material. The crude material was purified by reverse-phase preparative HPLC with 0.1% TFA in CH3CN/H2O, gradient 5-70% over 20 min to provide 6-(2-(4-chloro-3-methyl-1H-pyrazol-1-yl)-6-methylphenyl)-3-morpholinoquinolin-2-amine as a white solid. The purified compound was portioned between DCM and saturated sodium bicarbonate. The layers were separated and the aqueous layer was extracted with DCM. The combined organic extracts were washed with saturated sodium chloride and dried over sodium sulfate. The solution was filtered and concentrated in vacuo to give 6-(2-(4-chloro-3-methyl-1H-pyrazol-1-yl)-6-methylphenyl)-3-morpholinoquinolin-2-amine as a white solid. MS (ESI, pos. ion) m/z: 434 (M+1). | Cc1cccc(-n2cc(Cl)c(C)n2)c1-c1ccc2nc(N)c(N3CCOCC3)cc2c1 | null | Cc1cccc(-n2cc(Cl)c(C)n2)c1I | CC1(C)OB(c2ccc3nc(N)c(N4CCOCC4)cc3c2)OC1(C)C | null | [O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]([NH2:26])=[N:9][C:10]3[C:15]([CH:16]=2)=[CH:14][C:13](B2OC(C)(C)C(C)(C)O2)=[CH:12][CH:11]=3)[CH2:3][CH2:2]1.[Cl:27][C:28]1[C:29]([CH3:41])=[N:30][N:31]([C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([CH3:39])[C:34]=2I)[CH:32]=1.C(=O)([O-])[O-].[Na+].[Na+].O>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:27][C:28]1[C:29]([CH3:41])=[N:30][N:31]([C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([CH3:39])[C:34]=2[C:13]2[CH:14]=[C:15]3[C:10](=[CH:11][CH:12]=2)[N:9]=[C:8]([NH2:26])[C:7]([N:4]2[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)=[CH:16]3)[CH:32]=1 | null | C1COCCO1 | O | null | 140 | 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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