Sodium hydride → (S)-N-(2-chloroethyl)-5-(4-(5-fluoro-2-methoxypyridin-3-yl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

HRID 1426965노트

반응식

HRID 1426965 반응식
[F:1][C:2]1[CH:3]=[C:4]([C@H:10]2[CH2:14][O:13][C:12](=[O:15])[NH:11]2)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[H-].[Na+].Cl[C:19]1[CH:24]=[CH:23][N:22]2[N:25]=[CH:26][C:27]([C:28]([NH:30][CH2:31][CH2:32][Cl:33])=[O:29])=[C:21]2[N:20]=1.[NH4+].[Cl-]>CN(C=O)C.O>[Cl:33][CH2:32][CH2:31][NH:30][C:28]([C:27]1[CH:26]=[N:25][N:22]2[CH:23]=[CH:24][C:19]([N:11]3[C@@H:10]([C:4]4[C:5]([O:8][CH3:9])=[N:6][CH:7]=[C:2]([F:1])[CH:3]=4)[CH2:14][O:13][C:12]3=[O:15])=[N:20][C:21]=12)=[O:29]

참가 물질

7

반응물 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 86691741(S)-4-(5-fluoro-2-methoxypyridin-3-yl)oxazolidin-2-oneHCID 866917475-chloro-N-(2-chloroethyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

생성물 1

HCID 86691748(S)-N-(2-chloroethyl)-5-(4-(5-fluoro-2-methoxypyridin-3-yl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide수율 81%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of (S)-4-(5-fluoro-2-methoxypyridin-3-yl)oxazolidin-2-one (prepared according to Example 30; 50 mg, 0.236 mmol) in DMF (1 mL) was added sodium hydride (11 mg, 0.28 mmol, 60% in mineral oil). The mixture was stirred at ambient temperature for 20 minutes, then treated with 5-chloro-N-(2-chloroethyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (61 mg, 0.236 mmol). The mixture was stirred at 16 hours, and then treated with saturated NH4Cl solution (10 mL) and water (20 mL). The resulting precipitate was collected by filtration, washed with water and Et2O, then dried under reduced pressure to afford (S)-N-(2-chloroethyl)-5-(4-(5-fluoro-2-methoxypyridin-3-yl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (83 mg, 81% yield) as a beige solid. MS (apci) m/z=434.9 (M+H).

후처리

  1. stirringThe mixture was stirred at 16 hours
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water and Et2O
  4. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-55f8413649d24305b0a69a0cc4fc660f
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933084B2

반응 노트

불러오는 중…