4,7-difluoro-3-((3aS,4R,6S,6aR)-2,2,6-trimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-3H-imidazo[4,5-c]pyridine → 7-fluoro-3-((3aS,4R,6S,6aR)-2,2,6-trimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-3H-imidazo[4,5-c]pyridin-4-amine

HRID 470189

반응식

HRID 470189 반응식
F[C:2]1[C:7]2[N:8]=[CH:9][N:10]([C@H:11]3[C@H:18]4[C@H:14]([O:15][C:16]([CH3:20])([CH3:19])[O:17]4)[C@@H:13]([CH3:21])[CH2:12]3)[C:6]=2[C:5]([F:22])=[CH:4][N:3]=1.F[C:24]1[C:29]2[N:30]([C@H:33]3[C@H:40]4[C@H:36]([O:37][C:38]([CH3:42])([CH3:41])[O:39]4)[C@@H:35]([CH3:43])[CH2:34]3)[CH:31]=[N:32][C:28]=2[C:27]([F:44])=[CH:26][N:25]=1>N>[F:22][C:5]1[C:6]2[N:10]([C@H:11]3[C@H:18]4[C@H:14]([O:15][C:16]([CH3:20])([CH3:19])[O:17]4)[C@@H:13]([CH3:21])[CH2:12]3)[CH:9]=[N:8][C:7]=2[C:2]([NH2:25])=[N:3][CH:4]=1.[F:44][C:27]1[C:28]2[N:32]=[CH:31][N:30]([C@H:33]3[C@H:40]4[C@H:36]([O:37][C:38]([CH3:42])([CH3:41])[O:39]4)[C@@H:35]([CH3:43])[CH2:34]3)[C:29]=2[C:24]([NH2:3])=[N:25][CH:26]=1

참가 물질

5

반응물 2

HCID 583292804,7-difluoro-3-((3aS,4R,6S,6aR)-2,2,6-trimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-3H-imidazo[4,5-c]pyridineHCID 583292964,7-difluoro-1-((3 aS,4R,6S,6aR)-2,2,6-trimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-1H-imidazo [4,5-c]pyridine

생성물 2

HCID 672501877-fluoro-3-((3aS,4R,6S,6aR)-2,2,6-trimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-3H-imidazo[4,5-c]pyridin-4-amineHCID 672505457-fluoro-1-((3aS,4R,6S,6aR)-2,2,6-trimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-1H-imidazo[4,5-c]pyridin-4-amine

시약·촉매·용매 1

HCID 222Ammonia용매

반응 조건

온도
100 °C

실험 절차

Liquid ammonia (150 mL) was added to a mixture of 4,7-difluoro-1-((3aS,4R,6S,6aR)-2,2,6-trimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-1H-imidazo[4,5-c]pyridine (6-3) (180 mg, 0.6 mmol, 1 equiv) and 4,7-difluoro-3-((3aS,4R,6S,6aR)-2,2,6-trimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-3H-imidazo[4,5-c]pyridine (6-4) (180 mg, 0.6 mmol, 1 equiv). The resulting solution was heated in a high pressure vessel to 100° C. for 2 days. The mixture was then concentrated and purified by flash chromatography (12 g SiO2; 20-100% EtOAc in hexanes and then 100% ethanol to elute 6-3) to yield 7-fluoro-1-((3aS,4R,6S,6aR)-2,2,6-trimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-1H-imidazo[4,5-c]pyridin-4-amine (6-5) as a tan solid and 7-fluoro-3-((3aS,4R,6S,6aR)-2,2,6-trimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-3H-imidazo[4,5-c]pyridin-4-amine (6-6) as a tan solid. LRMS m/z (M+H) 306.9 found, 307.1 required.

후처리

  1. concentrationThe mixture was then concentrated
  2. custompurified by flash chromatography (12 g SiO2
  3. wash20-100% EtOAc in hexanes and then 100% ethanol to elute 6-3)

출처 및 근거

ORD 기록
ord-854cafc5fefc409c980abf8b9d476869
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629275B2

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