Ethanol hydrochloride → HCID 90313537, compound

HRID 1505798Notes

Reaction equation

HRID 1505798 reaction equation
[Cl:1][C:2]1[C:3]([CH3:38])=[C:4]([NH:8][C:9]([C:11]2[C:19]3[N:18]=[C:17]([NH:20][CH2:21][C:22]([OH:24])=[O:23])[NH:16][C:15]=3[CH:14]=[C:13]([NH:25][C:26]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:34]([F:37])([F:36])[F:35])=[O:27])[CH:12]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1.Cl.CCO>CO>[ClH:1].[Cl:1][C:2]1[C:3]([CH3:38])=[C:4]([NH:8][C:9]([C:11]2[C:19]3[N:18]=[C:17]([NH:20][CH2:21][C:22]([OH:24])=[O:23])[NH:16][C:15]=3[CH:14]=[C:13]([NH:25][C:26]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:34]([F:35])([F:36])[F:37])=[O:27])[CH:12]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21887872Ethanol hydrochlorideHCID 71267444HCID 71267444, compound

Product 1

HCID 90313537HCID 90313537, compoundYield 140.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

TFA (1 mL) was added to a solution of tert-butyl N-{4-[(3-chloro-2-methylphenyl)carbamoyl]-6-({[2-(trifluoro methyl)phenyl]carbonyl}amino)-1H-benzimidazol-2-yl}glycinate (95 mg) in methylene chloride (2 mL), and the mixture was stirred for 1 hour at room temperature, and concentrated. The residue was neutralized with 1N aqueous NaOH under ice-cooling and extracted with EtOAc. The ethyl acetate layer was dried over anhydrous magnesium sulfate and concentrated. The residue was purified on column chromatography to obtain N-{4-[(3-chloro-2-methylphenyl)carbamoyl]-6-({[2-(trifluoro methyl)phenyl]carbonyl}amino)-1H-benzimidazol-2-yl}glycine (50 mg) as white powder. N-{4-[(3-chloro-2-methylphenyl)carbamoyl]-6-({[2-(trifluoro methyl)phenyl]carbonyl}amino)-1H-benzimidazol-2-yl}glycine (16 mg) was suspended in MeOH. To the suspension was added 2N hydrogen chloride/EtOH solution (1 Eq) to obtain a homogeneous solution. The solvent was removed under reduced pressure. The residue was triturated in diethyl ether, and the precipitate was collected by filtration and dried to obtain the titled compound (12 mg) as white powder.

Workup

  1. customto obtain a homogeneous solution
  2. customThe solvent was removed under reduced pressure
  3. customThe residue was triturated in diethyl ether
  4. filtrationthe precipitate was collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-41ec62ba1c98473a927048dccd0af9f3
Source dataset
uspto-grants-2015_12
Patent number
US09216968B2

Reaction notes

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