Sodium Bicarbonate → 6-(Benzyloxy)-7-(5-(4-fluorobenzyl)thiazol-2-yl)-1-(2-oxo-2-(piperazin-1-yl)ethyl)imidazo[1,2-a]pyrimidin-5(1H)-one

HRID 1971842Notes

Reaction equation

HRID 1971842 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]([N:22]3[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]3)=[O:21])[C:12]2=[N:11][C:10]=1[C:35]1[S:36][C:37]([CH2:40][C:41]2[CH:46]=[CH:45][C:44]([F:47])=[CH:43][CH:42]=2)=[CH:38][N:39]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+]>CO.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:21])[N:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[C:12]2=[N:11][C:10]=1[C:35]1[S:36][C:37]([CH2:40][C:41]2[CH:42]=[CH:43][C:44]([F:47])=[CH:45][CH:46]=2)=[CH:38][N:39]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 86650581tert-Butyl 4-(2-(6-(benzyloxy)-7-(5-(4-fluorobenzyl)thiazol-2-yl)-5-oxoimidazo[1,2-a]pyrimidin-1(5H)-yl)acetyl)piperazine-1-carboxylate

Product 1

HCID 581268766-(Benzyloxy)-7-(5-(4-fluorobenzyl)thiazol-2-yl)-1-(2-oxo-2-(piperazin-1-yl)ethyl)imidazo[1,2-a]pyrimidin-5(1H)-oneYield 82%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of the product of example 111 (4.32 g, 8.23 mmol) in MeOH (50 ml), 6N HCl (25 ml) was added drop-wise at room temperature. The mixture was stirred for 2 hours, after which saturated sodium bicarbonate was added to adjust the pH 9˜10, and then extracted with CH2Cl2. The extracts were combined, washed with brine, and then dried over sodium sulfate. The solvent was removed under pressure to give the titled product as yellow slide (3.0 g, 82% yield).

Workup

  1. extractionextracted with CH2Cl2
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed under pressure

Sources & evidence

ORD record
ord-887bedf3026a414fb4534a5455415be5
Source dataset
uspto-grants-2013_04
Patent number
US08431581B2

Reaction notes

Loading…