Hydrochloric Acid → HCID 68582319, compound

HRID 2234057Notes

Reaction equation

HRID 2234057 reaction equation
C([NH:5][C:6]([C:8]1[N:9]=[C:10]([N:18]2[CH2:23][CH2:22][CH:21]([NH:24][C:25]([C:27]3[NH:28][C:29]([CH3:34])=[C:30]([Cl:33])[C:31]=3[Cl:32])=[O:26])[CH2:20][CH2:19]2)[S:11][C:12]=1[C:13]([O:15]CC)=[O:14])=O)(C)(C)C.[Li+].[OH-].C1COCC1.Cl>O.CO>[C:6]([C:8]1[N:9]=[C:10]([N:18]2[CH2:23][CH2:22][CH:21]([NH:24][C:25]([C:27]3[NH:28][C:29]([CH3:34])=[C:30]([Cl:33])[C:31]=3[Cl:32])=[O:26])[CH2:20][CH2:19]2)[S:11][C:12]=1[C:13]([OH:15])=[O:14])#[N:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 68579887HCID 68579887, compound

Product 1

HCID 68582319HCID 68582319, compoundYield 79.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of ethyl 4-[(tert-butylamino)carbonyl]-2-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-1,3-thiazole-5-carboxylate (Example 340; 140 mg, 0.31 mmol) and 2 N LiOH in water (0.93 ml, 1.86 mmol) in 6 ml 1:1 THF:MeOH was heated at 80° C. for 30 min in a microwave reactor. 1 N HCl (1.86 ml) was added and the mixture was diluted with water. Precipitated material was filtered and rinsed well with water. Drying of the precipitate in vacuo gave 105 mg of product.

Workup

  1. filtrationPrecipitated material was filtered
  2. washrinsed well with water
  3. customDrying of the precipitate in vacuo

Sources & evidence

ORD record
ord-178c96fc40dc4a13a65709c19cfb6425
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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