Sodium hydride → HCID 66747856, compound

HRID 1464971Notes

Reaction equation

HRID 1464971 reaction equation
[H-].[Na+].[CH2:3]([O:7][C:8]1[N:13]=[CH:12][N:11]=[C:10]([N:14]2[CH2:19][CH2:18][NH:17][C:16](=[O:20])[CH2:15]2)[CH:9]=1)[CH:4]([CH3:6])[CH3:5].Cl[CH2:22][C:23]1[O:24][C:25]2[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=2[N:27]=1>CN(C=O)C>[O:24]1[C:25]2[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=2[N:27]=[C:23]1[CH2:22][N:17]1[CH2:18][CH2:19][N:14]([C:10]2[CH:9]=[C:8]([O:7][CH2:3][CH:4]([CH3:6])[CH3:5])[N:13]=[CH:12][N:11]=2)[CH2:15][C:16]1=[O:20]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 20619892-(Chloromethyl)-1,3-benzoxazoleHCID 66748301HCID 66748301, compound

Product 1

HCID 66747856HCID 66747856, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (60% in mineral oil, 2.8 mg, 0.07 mmol) in DMF was added 4-(6-isobutoxypyrimidin-4-yl)piperazin-2-one (16 mg, 0.064 mmol). After 5 min, 2-(chloromethyl)benzo[d]oxazole (10.7 mg, 0.064 mmol) was added, and the mixture was stirred at rt for 30 min. The mixture was quenched with water, extracted with EtOAc (twice). The combined organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by preparative LC-MS to give 9.3 mg (38% yields) of the title compound.

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with EtOAc (twice)
  3. dry with materialThe combined organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative LC-MS
  6. customto give

Sources & evidence

ORD record
ord-5bda42803e9f4efe91b0e70d6dc4a6af
Source dataset
uspto-grants-2015_04
Patent number
US08999974B2

Reaction notes

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