Water → HCID 86606575, compound

HRID 2244449Notes

Reaction equation

HRID 2244449 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:11]2[S:15][C:14]([CH3:16])=[N:13][C:12]=2[C:17](=[O:26])[NH:18][C:19]2[CH:24]=[CH:23][N:22]=[C:21]([CH3:25])[CH:20]=2)[CH:5]=1.O.[OH-].[Na+]>C1COCC1>[CH3:25][C:21]1[CH:20]=[C:19]([NH:18][C:17]([C:12]2[N:13]=[C:14]([CH3:16])[S:15][C:11]=2[NH:10][C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([CH2:3][OH:2])[CH:5]=2)=[O:26])[CH:24]=[CH:23][N:22]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 14798Sodium HydroxideHCID 68407175HCID 68407175, compound

Product 1

HCID 86606575HCID 86606575, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-[2-Methyl-4-(2-methyl-pyridin-4-ylcarbamoyl)-thiazol-5-ylamino]-benzoic acid methyl ester (example 222, 0.425 g, 1.11 mmol) was dissolved in 15 mL dry THF. Lithiumalumiumhydride (0.169 g, 4.44 mmol) was added and the reaction mixture was stirred at room temperature for 1 h. Water (0.169 mL), 15% NaOH (0.169 mL) and again water (0.507 mL) was slowly added and the reaction mixture was filtered and evaporated. The crude material was recrystallized from ethyl acetate and dichloromethane to yield the title compound as a yellow solid (0.257 g, 65%), MS (ISP): m/e=355.3 (M+H+).

Workup

  1. additionwas added
  2. filtrationthe reaction mixture was filtered
  3. customevaporated
  4. customThe crude material was recrystallized from ethyl acetate and dichloromethane

Sources & evidence

ORD record
ord-3fa45ff8180449528245ecf8fa4c82ac
Source dataset
uspto-grants-2010_03
Patent number
US07678815B2

Reaction notes

Loading…