Ammonia → (1S,4R)-4-(4-amino-7-fluoro-1H-imidazo[4,5-c]pyridin-1-yl)cyclopent-2-enol

HRID 470172노트

반응식

HRID 470172 반응식
F[C:2]1[C:7]2[N:8]=[CH:9][N:10]([C@@H:11]3[CH2:15][C@H:14]([OH:16])[CH:13]=[CH:12]3)[C:6]=2[C:5]([F:17])=[CH:4][N:3]=1.[NH3:18]>>[NH2:18][C:2]1[C:7]2[N:8]=[CH:9][N:10]([C@@H:11]3[CH2:15][C@H:14]([OH:16])[CH:13]=[CH:12]3)[C:6]=2[C:5]([F:17])=[CH:4][N:3]=1

참가 물질

3

반응물 2

HCID 222AmmoniaHCID 58329283(1S,4R)-4-(4,7-difluoro-1H-imidazo[4,5-c]pyridin-1-yl)cyclopent-2-enol

생성물 1

HCID 58329277(1S,4R)-4-(4-amino-7-fluoro-1H-imidazo[4,5-c]pyridin-1-yl)cyclopent-2-enol

반응 조건

온도
100 °C

실험 절차

Liquid ammonia (100 mL) was added to (1S,4R)-4-(4,7-difluoro-1H-imidazo[4,5-c]pyridin-1-yl)cyclopent-2-enol (3-2) (220 mg, 0.6 mmol, 1 equiv). The resulting solution was heated in a high pressure vessel to 100° C. for 3 days. The mixture was then concentrated and purified via reverse phase chromatography (5-95% CH3CN/water with 0.1% TFA modifier) to yield (1S,4R)-4-(4-amino-7-fluoro-1H-imidazo[4,5-c]pyridin-1-yl)cyclopent-2-enol (3-3) as a white solid. LRMS m/z (M+H) 235.0 found, 235.1 required.

후처리

  1. concentrationThe mixture was then concentrated
  2. custompurified via reverse phase chromatography (5-95% CH3CN/water with 0.1% TFA modifier)

출처 및 근거

ORD 기록
ord-91f473d670454d7d94da68b663df8f19
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629275B2

반응 노트

불러오는 중…