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 1426965Notes

Reaction equation

HRID 1426965 reaction equation
[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]

Participants

7

Reactant 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

Product 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-carboxamideYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-55f8413649d24305b0a69a0cc4fc660f
Source dataset
uspto-grants-2015_01
Patent number
US08933084B2

Reaction notes

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