Lithium Hydroxide → 4-(3-Chloro-phenyl)-2-[6-(4-morpholin-4-yl-butyl)-benzoimidazol-1-yl]-thiazole-5-carboxylic acid

HRID 1667767Notes

Reaction equation

HRID 1667767 reaction equation
C([O:3][C:4]([C:6]1[S:10][C:9]([N:11]2[C:15]3[CH:16]=[C:17]([CH2:20][CH2:21][CH2:22][CH2:23][N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)[CH:18]=[CH:19][C:14]=3[N:13]=[CH:12]2)=[N:8][C:7]=1[C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[CH:31]=1)=[O:5])C.O1CCCC1.[OH-].[Li+]>O>[Cl:36][C:32]1[CH:31]=[C:30]([C:7]2[N:8]=[C:9]([N:11]3[C:15]4[CH:16]=[C:17]([CH2:20][CH2:21][CH2:22][CH2:23][N:24]5[CH2:25][CH2:26][O:27][CH2:28][CH2:29]5)[CH:18]=[CH:19][C:14]=4[N:13]=[CH:12]3)[S:10][C:6]=2[C:4]([OH:5])=[O:3])[CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 674437834-(3-Chloro-phenyl)-2-[6-(4-morpholin-4-yl-butyl)-benzoimidazol-1-yl]-thiazole-5-carboxylic acid ethyl ester

Product 1

HCID 674429774-(3-Chloro-phenyl)-2-[6-(4-morpholin-4-yl-butyl)-benzoimidazol-1-yl]-thiazole-5-carboxylic acidYield 72.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 0.078 g (0.15 mmole) of 4-(3-chloro-phenyl)-2-[6-(4-morpholin-4-yl-butyl)-benzoimidazol-1-yl]-thiazole-5-carboxylic acid ethyl ester (I.41f), 2 mL of tetrahydrofuran and 2 mL of water was added 0.034 g (1.49 mmole) of lithium hydroxide. The mixture was stirred at ambient temperature for 2 hours, then concentrated under reduced pressure and diluted with 5 mL of water. The pH was adjusted to ca. 6-7 by addition of 3M hydrochloric acid. The precipitate was collected by filtration to give 0.054 g of 4-(3-chloro-phenyl)-2-[6-(4-morpholin-4-yl-butyl)-benzoimidazol-1-yl]-thiazole-5-carboxylic acid (I.41 g) as a white solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additiondiluted with 5 mL of water
  3. additionThe pH was adjusted to ca. 6-7 by addition of 3M hydrochloric acid
  4. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-d4868c59dea2462fa1d6eaf6a5b69971
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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