Trifluoroacetic acid → 5-(4,4-Difluorooctahydro-4aH-cyclopropa[3,4]cyclopenta[1,2-c]pyrrol-4a-yl)-1-(2,2-dimethylpropyl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

HRID 629902노트

반응식

HRID 629902 반응식
[CH3:1][C:2]([CH3:34])([CH3:33])[CH2:3][N:4]1[C:12]2[C:7](=[N:8][C:9]([C:13]34[C:28]([F:30])([F:29])[CH:14]3[CH:15]3[CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH:16]3[CH2:27]4)=[CH:10][CH:11]=2)[N:6]([CH3:31])[C:5]1=[O:32].FC(F)(F)C(O)=O>ClCCl>[F:30][C:28]1([F:29])[C:13]2([C:9]3[N:8]=[C:7]4[N:6]([CH3:31])[C:5](=[O:32])[N:4]([CH2:3][C:2]([CH3:34])([CH3:1])[CH3:33])[C:12]4=[CH:11][CH:10]=3)[CH2:27][CH:16]3[CH:15]([CH:14]12)[CH2:19][NH:18][CH2:17]3

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 71136671tert-butyl 4a-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo-[4,5-b]pyridin-5-yl]-4,4-difluorooctahydro-2H-cyclopropa[3,4]cyclopenta[1,2-c]pyrrole-2-carboxylate

생성물 1

HCID 711366875-(4,4-Difluorooctahydro-4aH-cyclopropa[3,4]cyclopenta[1,2-c]pyrrol-4a-yl)-1-(2,2-dimethylpropyl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

tert-butyl 4a-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo-[4,5-b]pyridin-5-yl]-4,4-difluorooctahydro-2H-cyclopropa[3,4]cyclopenta[1,2-c]pyrrole-2-carboxylate (30-2, 100 mg, 0.21 mmol) was added to a mixture of dichloromethane (2.0 mL) and trifluoroacetic acid (0.5 mL) at room temperature. After stirring for 18 h, the solvent was removed in vacuo. The resulting residue was then diluted with ethyl acetate (100 mL) and washed sequentially with saturated sodium bicarbonate (2×50 mL), water (1×50 mL) and brine (1×50 mL). The organics were dried over magnesium sulfate, filtered, and concentrated in vacuo to give 1-[(2,2-Difluorocyclopropyl)methyl]-5-(1,2,3,3a,4,6a-hexahydrocyclopenta-[c]pyrrol-5-yl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (30-3) as a white solid. This material was carried on without further purification.

후처리

  1. customthe solvent was removed in vacuo
  2. additionThe resulting residue was then diluted with ethyl acetate (100 mL)
  3. washwashed sequentially with saturated sodium bicarbonate (2×50 mL), water (1×50 mL) and brine (1×50 mL)
  4. dry with materialThe organics were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-0d936da22ca3479b999eb478d0b678c8
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315518B2

반응 노트

불러오는 중…