Isobutanol → HCID 56655170, compound

HRID 1464963Notes

Reaction equation

HRID 1464963 reaction equation
[H-].[Na+].[CH3:3][CH:4]([CH3:7])[CH2:5][OH:6].Cl[C:9]1[N:14]=[CH:13][N:12]=[C:11]([N:15]2[CH2:20][CH2:19][N:18]([C:21]([C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[C:25]([F:30])[CH:24]=3)=[O:22])[CH2:17][CH2:16]2)[CH:10]=1>CN(C=O)C>[F:30][C:25]1[CH:24]=[C:23]([C:21]([N:18]2[CH2:19][CH2:20][N:15]([C:11]3[CH:10]=[C:9]([O:6][CH2:5][CH:4]([CH3:7])[CH3:3])[N:14]=[CH:13][N:12]=3)[CH2:16][CH2:17]2)=[O:22])[CH:28]=[CH:27][C:26]=1[CH3:29]

Participants

5

Reactant 3

HCID 6560IsobutanolHCID 24758Sodium hydrideHCID 86686656HCID 86686656, compound

Product 1

HCID 56655170HCID 56655170, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (60% in mineral oil, 20 mg, 0.52 mmol) in DMF was added 2-methylpropan-1-ol (39 mg, 0.52 mmol) at rt. After stirring at rt for 15 min, (4-(6-chloropyrimidin-4-yl)piperazin-1-yl)(3-fluoro-4-methylphenyl)methanone (35 mg, 0.11 mmol) was added to the mixture. After stirring at rt for 12 h, the mixture was poured onto water (5 mL), and the aqueous phase was extracted with dichloromethane (three times). The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was purified by preparative LC-MS to give 14.4 mg (37% yields) of the title compound.

Workup

  1. stirringAfter stirring at rt for 12 h
  2. additionthe mixture was poured onto water (5 mL)
  3. extractionthe aqueous phase was extracted with dichloromethane (three times)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative LC-MS
  7. customto give

Sources & evidence

ORD record
ord-bb6f35d842c04e758e99c766c4489947
Source dataset
uspto-grants-2015_04
Patent number
US08999974B2

Reaction notes

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