Citric Acid → HCID 178463789, compound

HRID 388997Notes

Reaction equation

HRID 388997 reaction equation
C[O:2][C:3](=[O:37])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:11]2[NH:15][C:14]3[CH:16]=[C:17]([N:32]([CH2:35][CH3:36])[CH2:33][CH3:34])[C:18]([C:20](=[O:31])[NH:21][C:22]4[CH:30]=[C:29]5[C:25]([CH:26]=[N:27][NH:28]5)=[CH:24][CH:23]=4)=[CH:19][C:13]=3[N:12]=2)[CH:5]=1.[Li+].[OH-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO.C1COCC1>[CH2:35]([N:32]([CH2:33][CH3:34])[C:17]1[C:18]([C:20](=[O:31])[NH:21][C:22]2[CH:30]=[C:29]3[C:25]([CH:26]=[N:27][NH:28]3)=[CH:24][CH:23]=2)=[CH:19][C:13]2[N:12]=[C:11]([NH:10][C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[C:3]([OH:37])=[O:2])[NH:15][C:14]=2[CH:16]=1)[CH3:36]

Participants

6

Reactant 3

HCID 311Citric AcidHCID 3939Lithium HydroxideHCID 178463790HCID 178463790, compound

Product 1

HCID 178463789HCID 178463789, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[6-diethylamino-5-(1H-indazol-6-ylcarbamoyl)-1H-benzimidazol-2-ylamino]-benzoic acid methyl ester (0.2 mmol; see Example 115) in methanol (2 mL) and THF (2 mL) was added 1M aqueous LiOH solution (2 mL). The resulting solution was then stirred at RT until the reaction was complete. The pH of the reaction mixture was adjusted with 5% aqueous citric acid solution to bring its pH to 4-5. The solid obtained was filtered, washed with ice-cold water, and dried under vacuum to afford 3-[6-diethylamino-5-(1H-indazol-6-ylcarbamoyl)-1H-benzimidazol-2-ylamino]-benzoic acid as a white solid. MS: m/z 484 (M+H)+.

Workup

  1. customThe solid obtained
  2. filtrationwas filtered
  3. washwashed with ice-cold water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-6b47e326522547479289e9f36fc21a49
Source dataset
uspto-grants-2013_02
Patent number
US08377983B2

Reaction notes

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