4-tert-Butylbenzoyl chloride → HCID 66894549, compound

HRID 551880Notes

Reaction equation

HRID 551880 reaction equation
[NH2:1][C:2]1[C:3]([CH3:26])=[C:4]([C:8]2[N:9]=[C:10]([NH:17][C:18]3[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=3)[C:11]3[N:12]([CH:14]=[CH:15][N:16]=3)[CH:13]=2)[CH:5]=[CH:6][CH:7]=1.C(N(C(C)C)CC)(C)C.[C:36]([C:40]1[CH:48]=[CH:47][C:43]([C:44](Cl)=[O:45])=[CH:42][CH:41]=1)([CH3:39])([CH3:38])[CH3:37]>C1COCC1>[C:36]([C:40]1[CH:41]=[CH:42][C:43]([C:44]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([C:8]3[N:9]=[C:10]([NH:17][C:18]4[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=4)[C:11]4[N:12]([CH:14]=[CH:15][N:16]=4)[CH:13]=3)[C:3]=2[CH3:26])=[O:45])=[CH:47][CH:48]=1)([CH3:39])([CH3:37])[CH3:38]

Participants

5

Reactant 3

HCID 743724-tert-Butylbenzoyl chlorideHCID 81531DiisopropylethylamineHCID 66895438HCID 66895438, compound

Product 1

HCID 66894549HCID 66894549, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-[6-(3-amino-2-methyl-phenyl)-imidazo[1,2-a]pyrazin-8-ylamino]-benzonitrile (380 mg; 1.12 mmol) and diisopropylethylamine (187 mg; 1.45 mmol) in anhydrous THF (25 mL) is stirred under nitrogen at rt. A solution of 4-tert-Butyl-benzoyl chloride (230 mg; 1.17 mmol) in 5 mL anhydrous THF is then added dropwise to the stirring reaction solution. After 30 minutes, the mixture is partitioned between ethyl acetate (75 mL) and water (75 mL) and the water layer extracted with ethyl acetate (2×50 mL). The organic layers are pooled, washed with brine and dried over anhydrous sodium sulfate. The filtrate is then concentrated in vacuo and the crude oil dissolved in a minimum volume of CH2Cl2. Diethyl ether is added and the resulting precipitate is filtered and washed with diethyl ether to provide 4-tert-butyl-N-{3-[8-(4-cyano-phenylamino)-imidazo[1,2-a]pyrazin-6-yl]-2-methyl-phenyl}-benzamide as a light orange solid (450 mg)

Workup

  1. customthe mixture is partitioned between ethyl acetate (75 mL) and water (75 mL)
  2. extractionthe water layer extracted with ethyl acetate (2×50 mL)
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe filtrate is then concentrated in vacuo
  6. dissolutionthe crude oil dissolved in a minimum volume of CH2Cl2
  7. additionDiethyl ether is added
  8. filtrationthe resulting precipitate is filtered
  9. washwashed with diethyl ether

Sources & evidence

ORD record
ord-db2d1e3d9676466096794afe62cf41e1
Source dataset
uspto-grants-2011_05
Patent number
US07947835B2

Reaction notes

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