Lithium hydroxide, monohydrate → HCID 66616329, compound

HRID 1046536Notes

Reaction equation

HRID 1046536 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH:9]([NH:12][C:13]2[N:18]=[C:17]([C:19]3[N:23]4[CH:24]=[CH:25][CH:26]=[C:27]([O:28][CH2:29][CH2:30][CH2:31][S:32]([CH3:35])(=[O:34])=[O:33])[C:22]4=[N:21][CH:20]=3)[CH:16]=[CH:15][N:14]=2)[CH2:8][CH2:7]1)=[O:5])C.O[Li].O>C1COCC1.CCO.O>[CH3:35][S:32]([CH2:31][CH2:30][CH2:29][O:28][C:27]1[C:22]2[N:23]([C:19]([C:17]3[CH:16]=[CH:15][N:14]=[C:13]([NH:12][CH:9]4[CH2:10][CH2:11][CH:6]([C:4]([OH:5])=[O:3])[CH2:7][CH2:8]4)[N:18]=3)=[CH:20][N:21]=2)[CH:24]=[CH:25][CH:26]=1)(=[O:34])=[O:33]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 66616479HCID 66616479, compound

Product 1

HCID 66616329HCID 66616329, compoundYield 95.3%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-{4-[8-(3-methanesulfonyl-propoxy)-imidazo[1,2-a]pyridine-3-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylic acid ethyl ester (0.1 g) and LiOH—H2O (42 mg) in THF (20 mL), EtOH (5 mL) and water (5 mL) was stirred at RT overnight. The reaction mixture was then concentrated, diluted with water, neutralized with HCl (1 N), and the resulting solid filtered and dried at 50° C. under vacuum overnight to provide 4-{4-[8-(3-methanesulfonyl-propoxy)-imidazo[1,2-a]pyridine-3-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylic acid (90 mg), which was used without further purification.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. additiondiluted with water
  3. filtrationthe resulting solid filtered
  4. customdried at 50° C. under vacuum overnight

Sources & evidence

ORD record
ord-189d5529b0a2455c8882eeae1a587d80
Source dataset
uspto-grants-2013_10
Patent number
US08569306B2

Reaction notes

Loading…