Tetrahydrofuran → HCID 90229434, compound

HRID 1505808Notes

Reaction equation

HRID 1505808 reaction equation
C1COCC1.Cl[C:7]1[NH:11][C:10]2[CH:12]=[C:13]([NH:27][C:28]([C:30]3[CH:35]=[C:34]([Cl:36])[CH:33]=[CH:32][C:31]=3[Cl: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.[NH2:38][CH2:39][C:40]([CH3:44])([CH3:43])[CH2:41][OH:42]>C(OCC)(=O)C>[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:38][CH2:39][C:40]([CH3:44])([CH3:43])[CH2:41][OH:42])[NH:11][C:10]=3[CH:12]=[C:13]([NH:27][C:28]([C:30]3[CH:35]=[C:34]([Cl:36])[CH:33]=[CH:32][C:31]=3[Cl:37])=[O:29])[CH:14]=2)=[O:17])[CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 1173261-Propanol, 3-amino-2,2-dimethyl-HCID 90230053HCID 90230053, compound

Product 1

HCID 90229434HCID 90229434, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

THF (1 mL) was added to 2-chloro-N-(3-chloro-2-methylphenyl)-6-{[(2,5-dichlorophenyl)carbonyl]amino}-1H-benzimidazole-4-carboxamide (50 mg) and 3-amino-2,2-dimethyl-1-propanol (400 mg). The mixture was stirred at 150° C. in a sealed pressure-proof stainless steel container for 8 hours. The reaction mixture was diluted with ethyl acetate, washed with brine and concentrated under reduced pressure. The residue was purified on column chromatography to obtain N-(3-chloro-2-methylphenyl)-6-{[(2,5-dichlorophenyl)carbonyl]amino}-2-[(3-hydroxy-2,2-dimethylpropyl)amino]-1H-benzimidazole-4-carboxamide (50 mg) as pale yellow powder. This was dissolved in MeOH (1 mL), and 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 (40 mg) as white powder.

Workup

  1. washwashed with brine
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified on column chromatography

Sources & evidence

ORD record
ord-ec817571341344d3b5c725ebab837af5
Source dataset
uspto-grants-2015_12
Patent number
US09216968B2

Reaction notes

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