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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 1971843
Notes
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Reaction equation

HRID 1971843 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 62493Pivaloyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 581268766-(Benzyloxy)-7-(5-(4-fluorobenzyl)thiazol-2-yl)-1-(2-oxo-2-(piperazin-1-yl)ethyl)imidazo[1,2-a]pyrimidin-5(1H)-one

Product 1

HCID 581269226-(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
Yield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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

  1. stirringThe mixture was stirred at room temperature for 2 hours
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes