Lithium Hydroxide → HCID 86717888, compound

HRID 1844140Notes

Reaction equation

HRID 1844140 reaction equation
[CH:1]1([C:4]2[N:5]=[C:6]3[C:11]([O:12][CH2:13][C:14]4[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=4[F:21])=[CH:10][CH:9]=[CH:8][N:7]3[C:22]=2[C:23]([O:25]CC)=[O:24])[CH2:3][CH2:2]1.[OH-].[Li+]>CO.O1CCCC1>[CH:1]1([C:4]2[N:5]=[C:6]3[C:11]([O:12][CH2:13][C:14]4[C:15]([F:21])=[CH:16][CH:17]=[CH:18][C:19]=4[F:20])=[CH:10][CH:9]=[CH:8][N:7]3[C:22]=2[C:23]([OH:25])=[O:24])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 3939Lithium Hydroxide2×HCID 86717887HCID 86717887, compound

Product 1

HCID 86717888HCID 86717888, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

410 mg of ethyl 2-cyclopropyl-8-[(2,6-difluorobenzyl)oxy]imidazo[1,2-a]pyridine-3-carboxylate (Example 27A, 1.1 mmol, 1 equivalent) were initially charged in 15 ml of methanol/tetrahydro-furan (1:1), and 5.5 ml of a 1 N aqueous lithium hydroxide solution (5.5 mmol, 5 equivalents) were added. The reaction mixture was stirred at RT overnight, another 5.5 ml of 1 N aqueous lithium hydroxide solution were added, and the mixture was stirred at RT for another night. The mixture was concentrated and the residue was taken up in water and acidified with 1 N aqueous hydrochloric acid. The precipitated product was filtered off and dried under high vacuum. This gave 293 mg (77% of theory) of the title compound.

Workup

  1. stirringthe mixture was stirred at RT for another night
  2. concentrationThe mixture was concentrated
  3. filtrationThe precipitated product was filtered off
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-6555f482054c45cab00de8e3a18d7330
Source dataset
uspto-grants-2015_02
Patent number
US08946215B2

Reaction notes

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