Water → HCID 136413229、化合物

HRID 59859

反応式

HRID 59859 の反応式
[O:1]=[C:2]([CH3:29])[CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:17]=[CH:16][N:15]([C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=3)[N:14]=2)=[CH:9][CH:8]=1)=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH:36]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[N:45]=[C:46]=[S:47])([CH3:38])[CH3:37].O>CN(C)C=O>[OH:1]/[C:2](/[CH3:29])=[C:3](/[C:46](=[S:47])[NH:45][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=1[CH:36]([CH3:37])[CH3:38])\[C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[N:17]=[CH:16][N:15]([C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]([F:27])([F:26])[F:28])=[CH:20][CH:19]=3)[N:14]=2)=[CH:11][CH:12]=1)=[O:5]

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1420522-Isopropylphenyl isothiocyanateHCID 866757993-oxo-N-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-butanamide

生成物 1

HCID 136413229HCID 136413229、化合物収率 48.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A portion of the solid from Step 1 (0.50 g, 1.24 mmol) was dissolved in 5 mL of dry N,N-dimethylformamide (DMF) and stirred at ambient temperature while potassium carbonate (0.25 g, 1.81 mmol) and 2-isopropylphenyl isothiocyanate (0.25 g, 1.41 mmol) were added. The solution was stirred for 18 h, then it was poured into 15 mL of water, extracted with ether, and the solvent evaporated. Chromatography of the crude product (0-70% EtOAc-hexanes) gave 350 mg of the title compound as an off-white solid. mp 141-144° C. 1H NMR (400 MHz, CDCl3) δ 15.35-14.58 (m, 1H), 10.93 (s, 1H), 8.57 (m, 3H), 8.31-8.11 (m, 6H), 7.71 (m, 12H), 7.56-7.30 (m, 15H), 5.35 (s, 1H), 3.02 (heptet, J=6.9 Hz, 1H), 2.52 (s, 3H), 1.35-1.11 (m, 6H); ESIMS m/z 582 ([M+H]+).

後処理

  1. additionwere added
  2. extractionextracted with ether
  3. customthe solvent evaporated

出典と根拠

ORDレコード
ord-df36fe8a5ba749379eb9a3c2bd98cf71
出典データセット
uspto-grants-2016_09
特許番号
US09440964B2

関連ノート

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