Ethanol → HCID 66616312, compound

HRID 1046530Notes

Reaction equation

HRID 1046530 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]([C:28]([OH:31])([CH3:30])[CH3:29])[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>[OH:31][C: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)([CH3:29])[CH3:30]

Participants

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 666162114-{4-[8-(1-Hydroxy-1-methyl-ethyl)-imidazo[1,2-a]pyridin-3-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylic acid ethyl ester

Product 1

HCID 66616312HCID 66616312, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-{4-[8-(1-hydroxy-1-methyl-ethyl)-imidazo[1,2-a]pyridin-3-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylic acid ethyl ester (0.215 g), LiOH—H2O (0.106 g), THF (20 mL), EtOH (5 mL) and water (5 mL) was stirred at RT overnight. The reaction mixture was then concentrated to remove THF and EtOH, neutralized with HCl (1 N), and the resulting solid filtered and dried at 50° C. under vacuum overnight to provide 4-{4-[8-(1-hydroxy-1-methyl-ethyl)-imidazo[1,2-a]pyridin-3-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylic acid (0.175 g), which was used without further purification.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. customto remove THF and EtOH
  3. filtrationthe resulting solid filtered
  4. customdried at 50° C. under vacuum overnight

Sources & evidence

ORD record
ord-f085e6ae82e8458da89b7c95675e222c
Source dataset
uspto-grants-2013_10
Patent number
US08569306B2

Reaction notes

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