Lithium Hydroxide → 2-[6-(4-Methyl-piperazin-1-ylmethyl)-benzoimidazol-1-yl]-4-phenyl-thiazole-5-carboxylic acid

HRID 1667682Notes

Reaction equation

HRID 1667682 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][N:21]4[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]4)[CH:18]=[CH:19][C:14]=3[N:13]=[CH:12]2)=[N:8][C:7]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:5])C.O1CCCC1.[OH-].[Li+]>O>[CH3:27][N:24]1[CH2:25][CH2:26][N:21]([CH2:20][C:17]2[CH:18]=[CH:19][C:14]3[N:13]=[CH:12][N:11]([C:9]4[S:10][C:6]([C:4]([OH:5])=[O:3])=[C:7]([C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)[N:8]=4)[C:15]=3[CH:16]=2)[CH2:22][CH2:23]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 674282602-[6-(4-Methyl-piperazin-1-ylmethyl)-benzoimidazol-1-yl]-4-phenyl-thiazole-5-carboxylic acid ethyl ester

Product 1

HCID 674462532-[6-(4-Methyl-piperazin-1-ylmethyl)-benzoimidazol-1-yl]-4-phenyl-thiazole-5-carboxylic acidYield 64.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 0.041 g (0.089 mmole) of 2-[6-(4-methyl-piperazin-1-ylmethyl)-benzoimidazol-1-yl]-4-phenyl-thiazole-5-carboxylic acid ethyl ester (I.1a), 1 mL of tetrahydrofuran and 1 mL of water was added 0.011 g of lithium hydroxide. The reaction mixture was heated to 60 degrees for 30 minutes and then concentrated under reduced pressure. The mixture was diluted with 5 mL of water and then extracted with 5 mL of ethyl acetate. The pH of the aqueous layer was adjusted to ca 7 by addition of 1M hydrochloric acid and then extracted with 5 mL of ethyl acetate. A precipitate formed in aqueous layer after extraction. The solid was collected by filtration and air dried to give 0.025 g of 2-[6-(4-methyl-piperazin-1-ylmethyl)-benzoimidazol-1-yl]-4-phenyl-thiazole-5-carboxylic acid (I.1b) as an off-white solid.

Workup

  1. temperatureThe reaction mixture was heated to 60 degrees for 30 minutes
  2. concentrationconcentrated under reduced pressure
  3. additionThe mixture was diluted with 5 mL of water
  4. extractionextracted with 5 mL of ethyl acetate
  5. additionby addition of 1M hydrochloric acid
  6. extractionextracted with 5 mL of ethyl acetate
  7. customA precipitate formed in aqueous layer
  8. extractionafter extraction
  9. filtrationThe solid was collected by filtration and air
  10. customdried

Sources & evidence

ORD record
ord-5c45f790099043ddb2718eaa9bf60237
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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