Tributylphosphine → 1-(2-Cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-((5-(trifluoromethyl)thiophen-2-yl)methoxy)pyridin-2(1H)-one

HRID 2202978노트

반응식

HRID 2202978 반응식
[CH:1]1([C:4]2[N:8]([CH3:9])[C:7]3[CH:10]=[C:11]([N:14]4[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:15]4=[O:21])[CH:12]=[CH:13][C:6]=3[N:5]=2)[CH2:3][CH2:2]1.[F:22][C:23]([F:32])([F:31])[C:24]1[S:28][C:27]([CH2:29]O)=[CH:26][CH:25]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1COCC1>[CH:1]1([C:4]2[N:8]([CH3:9])[C:7]3[CH:10]=[C:11]([N:14]4[CH:19]=[CH:18][C:17]([O:20][CH2:29][C:27]5[S:28][C:24]([C:23]([F:32])([F:31])[F:22])=[CH:25][CH:26]=5)=[CH:16][C:15]4=[O:21])[CH:12]=[CH:13][C:6]=3[N:5]=2)[CH2:2][CH2:3]1

참가 물질

6

반응물 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 539255405-(Trifluoromethyl)-2-thiophenemethanolHCID 896910841-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-hydroxypyridin-2(1H)-one

생성물 1

HCID 896910961-(2-Cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-((5-(trifluoromethyl)thiophen-2-yl)methoxy)pyridin-2(1H)-one수율 35.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
60 °C

실험 절차

To a mixture of 1-(2-cyclopropyl-1-methyl-1H-benzo[d]imidazol-6-yl)-4-hydroxypyridin-2(1H)-one (100 mg), (5-(trifluoromethyl)thiophen-2-yl)methanol (130 mg) and tributylphosphine (0.26 ml) in THF (10 ml) was added 1,1′-(azodicarbonyl)dipiperidine (269 mg), and the mixture was stirred at 60° C. overnight. The solvent was evaporated and the residue was purified by silica gel column chromatography (hexane/EtOAc then EtOAc/MeOH), followed by NH silica gel column chromatography (hexane/EtOAc). The resulting solid was recrystallized from EtOAc-EtOH to give the title compound (55.7 mg) as an off-white solid.

후처리

  1. customThe solvent was evaporated
  2. customthe residue was purified by silica gel column chromatography (hexane/EtOAc
  3. customThe resulting solid was recrystallized from EtOAc-EtOH

출처 및 근거

ORD 기록
ord-5268ae557d24472896eb9b434f58147e
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365540B2

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