2-Methoxyethylamine → HCID 71267467, compound

HRID 1505796Notes

Reaction equation

HRID 1505796 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH2:5].Cl[C:7]1[NH:11][C:10]2[CH:12]=[C:13]([NH:27][C:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[C:36]([F:39])([F:38])[F:37])=[O:29])[CH:14]=[C:15]([C:16]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:20]=3[CH3:26])=[O:17])[C:9]=2[N:8]=1>>[Cl:25][C:21]1[C:20]([CH3:26])=[C:19]([NH:18][C:16]([C:15]2[C:9]3[N:8]=[C:7]([NH:5][CH2:4][CH2:3][O:2][CH3:1])[NH:11][C:10]=3[CH:12]=[C:13]([NH:27][C:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[C:36]([F:37])([F:38])[F:39])=[O:29])[CH:14]=2)=[O:17])[CH:24]=[CH:23][CH:22]=1

Participants

3

Reactant 2

HCID 80182-MethoxyethylamineHCID 71267437HCID 71267437, compound

Product 1

HCID 71267467HCID 71267467, compound

Procedure

2-Methoxyethylamine (2 mL) was added to 2-chloro-N-(3-chloro-2-methylphenyl)-6-({[2-(trifluoromethyl)phenyl]carbonyl}amino)-1H-benzimidazole-4-carboxamide (40 mg, Example 135). The mixture was stirred at 150° C. in a sealed pressure-proof stainless steel container for 17 hours. The reaction mixture was washed with brine and concentrated under reduced pressure. The residue was purified on column chromatography to obtain N-(3-chloro-2-methylphenyl)-2-[(2-methoxyethyl)amino]-6-({[2-(trifluoromethyl)phenyl]carbonyl}amino)-1H-benzimidazole-4-carboxamide (35 mg) as white powder. This was dissolved in MeOH (1 mL), 2N hydrogen chloride/EtOH solution (1 Eq) was added, and it was stirred and concentrated. The residue was triturated in diethyl ether, and the precipitate was collected by filtration and dried to obtain the titled compound (28 mg) as white powder.

Workup

  1. washThe reaction mixture was washed with brine
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified on column chromatography

Sources & evidence

ORD record
ord-b5cbd5df22c34a379ff392b8e07b38ef
Source dataset
uspto-grants-2015_12
Patent number
US09216968B2

Reaction notes

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