Water → HCID 136413229, 화합물

HRID 59859

반응식

HRID 59859 반응식
[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]

참가 물질

6

반응물 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

생성물 1

HCID 136413229HCID 136413229, 화합물수율 48.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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]+).

후처리

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

출처 및 근거

ORD 기록
ord-df36fe8a5ba749379eb9a3c2bd98cf71
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440964B2

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