Lithium Hydroxide → HCID 25206017, compound

HRID 1809173Notes

Reaction equation

HRID 1809173 reaction equation
C[O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11][C:12]2[C:13]3[N:14]([C:18]([C:21]4[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=4)=[CH:19][N:20]=3)[CH:15]=[CH:16][N:17]=2)=[CH:6][CH:5]=1.[OH-].[Li+]>O1CCCC1.O>[CH3:30][O:29][C:23]1[CH:22]=[C:21]([C:18]2[N:14]3[CH:15]=[CH:16][N:17]=[C:12]([NH:11][CH2:10][C:7]4[CH:6]=[CH:5][C:4]([C:3]([OH:31])=[O:2])=[CH:9][CH:8]=4)[C:13]3=[N:20][CH:19]=2)[CH:26]=[CH:25][C:24]=1[O:27][CH3:28]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 25206651HCID 25206651, compound

Product 1

HCID 25206017HCID 25206017, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-{[3-(3,4-Dimethoxy-phenyl)-imidazo[1,2-a]pyrazin-8-ylamino]-methyl}-benzoic acid methyl ester (0.20 g, 0.48 mmol) in tetrahydrofuran (4 ml) was added lithium hydroxide (0.72 ml, 0.72 mmol, 1 M aqueous solution). The reaction was stirred at ambient temperature for 24 hours then diluted with water (30 mL) and washed with ethyl acetate (30 ml). The aqueous phase was acidified with 1 M aqueous HCl and extracted with ethyl acetate (3×30 ml), the organic layers were combined and dried with magnesium sulphate, filtered and concentrated in vaccuo. The product, 4-{[3-(3,4-Dimethoxy-phenyl)-imidazo[1,2-a]pyrazin-8-ylamino]-methyl}-benzoic acid, is obtained as an off white solid (50 mg, 26%) (LC-MS m/z 405 [M+H]+).

Workup

  1. washwashed with ethyl acetate (30 ml)
  2. extractionextracted with ethyl acetate (3×30 ml)
  3. dry with materialdried with magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vaccuo

Sources & evidence

ORD record
ord-f9d355f317a64fc99437b3e430fdb64d
Source dataset
uspto-grants-2013_01
Patent number
US08362018B2

Reaction notes

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