Cyanogen Bromide → (S)-3-(3-(4-(5-amino-1,3,4-oxadiazol-2-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(4-fluorophenyl)oxazolidin-2-one

HRID 539125노트

반응식

HRID 539125 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:12][O:11][C:10](=[O:13])[N:9]2[C:14]2[CH:19]=[CH:18][N:17]3[N:20]=[CH:21][C:22]([C:23]4[CH:32]=[CH:31][C:26]([C:27]([NH:29][NH2:30])=[O:28])=[CH:25][CH:24]=4)=[C:16]3[N:15]=2)=[CH:4][CH:3]=1.[N:33]#[C:34]Br.C([O-])(O)=O.[Na+]>O1CCOCC1.O.CCOC(C)=O>[NH2:33][C:34]1[O:28][C:27]([C:26]2[CH:31]=[CH:32][C:23]([C:22]3[CH:21]=[N:20][N:17]4[CH:18]=[CH:19][C:14]([N:9]5[C@@H:8]([C:5]6[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=6)[CH2:12][O:11][C:10]5=[O:13])=[N:15][C:16]=34)=[CH:24][CH:25]=2)=[N:29][N:30]=1

참가 물질

7

반응물 3

HCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 67035490(S)-4-(5-(4-(4-fluorophenyl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzohydrazide

생성물 1

HCID 67034511(S)-3-(3-(4-(5-amino-1,3,4-oxadiazol-2-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(4-fluorophenyl)oxazolidin-2-one수율 16%

시약·촉매·용매 3

HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

실험 절차

To a suspension of (S)-4-(5-(4-(4-fluorophenyl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzohydrazide (0.040 g, 0.0925 mmol) in dioxane (4 mL) was added cyanic bromide (0.0216 g, 0.204 mmol) followed by a solution of NaHCO3 (0.00933 g, 0.111 mmol) in water (0.9 mL). The resulting mixture was stirred at ambient temperature overnight, then diluted with EtOAc. The organic layer was washed with brine and water, dried (phase separator silicone treated filter paper) and concentrated. The crude material was purified on silica gel (2-5% MeOH in DCM) to provide (S)-3-(3-(4-(5-amino-1,3,4-oxadiazol-2-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(4-fluorophenyl)oxazolidin-2-one (0.0066 g, 16% yield). LCMS (APCI+) m/z 458 [M+H]+.

후처리

  1. washThe organic layer was washed with brine and water
  2. customdried
  3. addition(phase separator silicone treated filter paper)
  4. concentrationconcentrated
  5. customThe crude material was purified on silica gel (2-5% MeOH in DCM)

출처 및 근거

ORD 기록
ord-229b5807c8ed4616a99e4fc427e2c048
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865726B2

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