Lithium Hydroxide → 4-(5-Bromoimidazo[1,2-a]pyrazin-8-ylamino) benzoic acid

HRID 1924892Notes

Reaction equation

HRID 1924892 reaction equation
C[O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[C:12]3[N:13]([CH:18]=[CH:19][N:20]=3)[C:14]([Br:17])=[CH:15][N:16]=2)=[CH:6][CH:5]=1.[Li+].[OH-]>C1COCC1.O>[Br:17][C:14]1[N:13]2[CH:18]=[CH:19][N:20]=[C:12]2[C:11]([NH:10][C:7]2[CH:6]=[CH:5][C:4]([C:3]([OH:21])=[O:2])=[CH:9][CH:8]=2)=[N:16][CH:15]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 590230964-(5-Bromoimidazo[1,2-a]pyrazin-8-ylamino)benzoic acid methyl ester

Product 1

HCID 582288294-(5-Bromoimidazo[1,2-a]pyrazin-8-ylamino) benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(5-bromoimidazo[1,2-a]pyrazin-8-ylamino)benzoic acid methyl ester (6.02 g, 17.3 mmol) and LiOH (7.3 g, 174 mmol) in THF (200 mL) and water (200 mL) is stirred at 25° C. for 18 hours. The majority of the solvents are removed in vacuo, then to the remaining aqueous solution is added EtOAc. The aqueous layer is separated, then washed once more EtOAc. The aqueous phase is separated, acidified to pH 5 using concentrated hydrochloric acid and the resultant solid filtered and dried in the vacuum oven. The solid is identified as the desired title acid.

Workup

  1. customThe majority of the solvents are removed in vacuo
  2. additionto the remaining aqueous solution is added EtOAc
  3. customThe aqueous layer is separated
  4. washwashed once more EtOAc
  5. customThe aqueous phase is separated
  6. filtrationthe resultant solid filtered
  7. customdried in the vacuum oven

Sources & evidence

ORD record
ord-5d8d106a86684156b0b2db7bc3b7cbf0
Source dataset
uspto-grants-2012_05
Patent number
US08178530B2

Reaction notes

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