Hydrochloric Acid → HCID 71279237, compound

HRID 1621147Notes

Reaction equation

HRID 1621147 reaction equation
[CH3:1][N:2]1[C:6]([C:7](=[O:23])[NH:8][CH2:9][CH2:10][C:11]2[N:12]([CH3:22])[CH:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:15]=2)=[C:5]([C:24]([O:26]C)=[O:25])[N:4]=[N:3]1.[Li+].[OH-].Cl.ClCCl>C1COCC1.CO>[CH3:1][N:2]1[C:6]([C:7](=[O:23])[NH:8][CH2:9][CH2:10][C:11]2[N:12]([CH3:22])[CH:13]=[C:14]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:15]=2)=[C:5]([C:24]([OH:26])=[O:25])[N:4]=[N:3]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 6344DichloromethaneHCID 71279172HCID 71279172, compound

Product 1

HCID 71279237HCID 71279237, compoundYield 70.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 1-methyl-5-(2-(1-methyl-4-phenyl-1H-imidazol-2-yl)ethylcarbamoyl)-1H-1,2,3-triazole-4-carboxylate (77 mg, 209 μmol) in THF (0.9 mL) and MeOH (0.3 mL) was added LiOH (1M aqueous solution, 418 μL, 418 μmol) at 0-5° C. The ice bath was removed and the mixture was stirred at RT for 4 h. HCl (1M aqueous solution, 0.42 mL, 0.42 mmol) was added and the solution was poured into dichloromethane (40 mL) to result in a suspension. The solid precipitate was filtered, washed with THF/water 4:1 and dried in vacuo to give the product as colorless solid (52 mg, 147 μmol, 70.2%).

Workup

  1. customThe ice bath was removed
  2. customto result in a suspension
  3. filtrationThe solid precipitate was filtered
  4. washwashed with THF/water 4:1
  5. customdried in vacuo

Sources & evidence

ORD record
ord-68831177d67e483bbfe7b8da0db24d6f
Source dataset
uspto-grants-2014_07
Patent number
US08772510B2

Reaction notes

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