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 1426965ノート

反応式

HRID 1426965 の反応式
[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]

参加物

7

反応物 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

生成物 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-carboxamide収率 81%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-55f8413649d24305b0a69a0cc4fc660f
出典データセット
uspto-grants-2015_01
特許番号
US08933084B2

反応ノート

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