Pivaloyl chloride → 6-(benzyloxy)-7-(5-(4-fluorobenzyl)thiazol-2-yl)-1-(2-oxo-2-(4-pivaloylpiperazin-1-yl)ethyl)imidazo[1,2-a]pyrimidin-5(1H)-one

HRID 1971843Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]2[CH:16]=[CH:17][N:18]([CH2:19][C:20](=[O:27])[N:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[C:12]2=[N:11][C:10]=1[C:28]1[S:29][C:30]([CH2:33][C:34]2[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=2)=[CH:31][N:32]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[C:50](Cl)(=[O:55])[C:51]([CH3:54])([CH3:53])[CH3:52].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]2[CH:16]=[CH:17][N:18]([CH2:19][C:20](=[O:27])[N:21]3[CH2:26][CH2:25][N:24]([C:50](=[O:55])[C:51]([CH3:54])([CH3:53])[CH3:52])[CH2:23][CH2:22]3)[C:12]2=[N:11][C:10]=1[C:28]1[S:29][C:30]([CH2:33][C:34]2[CH:35]=[CH:36][C:37]([F:40])=[CH:38][CH:39]=2)=[CH:31][N:32]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of the product of example 112 (200 mg, 0.36 mmol) and DIPEA (50.94 mg, 0.39 mmol) in CH2Cl2 (10 ml) was stirred at 0° C. Then pivaloyl chloride (47.48 mg, 0.39 mmol) was added dropwise. The mixture was stirred at room temperature for 2 hours, after which saturated sodium bicarbonate was added and then extracted with ethyl acetate. The extracts were combined, washed with brine, and then dried over sodium sulfate. The product was purified by column chromatography (CH2Cl2/MeOH=10/1) to give the desired product (207 mg, 90% yield).

Workup

stirringThe mixture was stirred at room temperature for 2 hours
extractionextracted with ethyl acetate
washwashed with brine
dry with materialdried over sodium sulfate
customThe product was purified by column chromatography (CH2Cl2/MeOH=10/1)

Sources & evidence

ORD record: ord-b835cf3b4cf2462ab86da827fad5e835
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431581B2

Reaction notes

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