Hydrochloric Acid → HCID 71279180, compound

HRID 1621091Notes

Reaction equation

HRID 1621091 reaction equation
[CH3:1][N:2]1[C:6]([C:7](=[O:21])[NH:8][CH2:9][CH2:10][C:11]2[N:15]([CH3:16])[C:14]3[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=3[N:12]=2)=[C:5]([C:22]([O:24]C)=[O:23])[N:4]=[C:3]1[CH3:26].[Li+].[OH-].Cl>C1COCC1.CO>[CH3:1][N:2]1[C:6]([C:7](=[O:21])[NH:8][CH2:9][CH2:10][C:11]2[N:15]([CH3:16])[C:14]3[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=3[N:12]=2)=[C:5]([C:22]([OH:24])=[O:23])[N:4]=[C:3]1[CH3:26]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 71279102HCID 71279102, compound

Product 1

HCID 71279180HCID 71279180, compoundYield 95.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 1,2-dimethyl-5-(2-(1-methyl-1H-benzo[d]imidazol-2-yl)ethylcarbamoyl)-1H-imidazole-4-carboxylate (98 mg, 276 μmol) in THF (2 mL) and MeOH (1 mL) at room temperature was added LiOH (1M, 1.1 mL, 1.1 mmol). The reaction mixture was stirred at r. t. for 6 h. The reaction mixture was acidified with hydrochloric acid (1M, 1.5 mL), all volatiles were removed in vacuo and the residue was suspended in dichloromethane/MeOH (95:5) and filtered. The liquid was evaporated and dried in vacuo to give the product as colorless amorphous material (95 mg, 264 μmol, 95.9%) which was used without any further purification for the next step. MS: M=340.2 (M−H)−

Workup

  1. customall volatiles were removed in vacuo
  2. filtrationfiltered
  3. customThe liquid was evaporated
  4. customdried in vacuo

Sources & evidence

ORD record
ord-70901498a001442e9219e3bdc28f1fea
Source dataset
uspto-grants-2014_07
Patent number
US08772510B2

Reaction notes

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