Benzoyl isothiocyanate → tert-butyl 4-fluoro-3-[(6-oxo-2-thioxo-1,2,6,7-tetrahydro-3H-purin-3-yl)methyl]-1H-indole-1-carboxylate

HRID 912676

반응식

HRID 912676 반응식
[NH2:1][C:2]([C:4]1[NH:8][CH:7]=[N:6][C:5]=1[NH:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][C:18]=2[F:20])[N:13]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:12]=1)=[O:3].C(N=[C:37]=[S:38])(=O)C1C=CC=CC=1>C(Cl)Cl>[F:20][C:18]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:19]=1[C:11]([CH2:10][N:9]1[C:5]3[N:6]=[CH:7][NH:8][C:4]=3[C:2](=[O:3])[NH:1][C:37]1=[S:38])=[CH:12][N:13]2[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]

참가 물질

4

반응물 2

HCID 68284Benzoyl isothiocyanateHCID 67417268HCID 67417268, 화합물

생성물 1

HCID 86631124tert-butyl 4-fluoro-3-[(6-oxo-2-thioxo-1,2,6,7-tetrahydro-3H-purin-3-yl)methyl]-1H-indole-1-carboxylate수율 48%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
80 °C

실험 절차

A solution of tert-butyl 3-({[5-(aminocarbonyl)-1H-imidazol-4-yl]amino}methyl)-4-fluoro-1H-indole-1-carboxylate (0.17 g, 0.45 mmol, obtained from Example 11(b)) and benzoyl isothiocyanate (0.073 mL, 0.54 mmol) in CH2Cl2 (5 mL) was stirred for 3 h 20 minutes and then evaporated. Ammonia (7 M in MeOH, 4 mL) was added to the residue and the mixture was heated to 80° C. for 2 h and then evaporated. Purification by flash chromatography using MeOH (2%) in CHCl3 gave the title compound (0.089 g, 48%).

후처리

  1. customevaporated
  2. additionAmmonia (7 M in MeOH, 4 mL) was added to the residue
  3. customevaporated
  4. customPurification by flash chromatography

출처 및 근거

ORD 기록
ord-b2adcce52c3f4ef780e218c95ce6ba45
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026244B2

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