Tetrahydrofuran → HCID 71267541, compound

HRID 1505809Notes

Reaction equation

HRID 1505809 reaction equation
C1COCC1.Cl[C:7]1[NH:11][C:10]2[CH:12]=[C:13]([NH:27][C:28]([C:30]3[C:35]([F:36])=[CH:34][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.[CH:38]([O:41][CH2:42][CH2:43][NH2:44])([CH3:40])[CH3:39]>C(OCC)(=O)C>[Cl:37][C:31]1[CH:32]=[CH:33][CH:34]=[C:35]([F:36])[C:30]=1[C:28]([NH:27][C:13]1[CH:14]=[C:15]([C:16]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:20]=2[CH3:26])=[O:17])[C:9]2[N:8]=[C:7]([NH:44][CH2:43][CH2:42][O:41][CH:38]([CH3:40])[CH3:39])[NH:11][C:10]=2[CH:12]=1)=[O:29]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 5338662-(Propan-2-yloxy)ethan-1-amineHCID 90229380HCID 90229380, compound

Product 1

HCID 71267541HCID 71267541, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

THF (1 mL) was added to 2-chloro-6-{[(2-chloro-6-fluorophenyl)carbonyl]amino}-N-(3-chloro-2-methylphenyl)-1H-benzimidazole-4-carboxamide (50 mg) and 2-aminoethyl isopropyl ether (32 mg). The mixture was stirred at 150° C. in a sealed pressure-proof stainless steel container for 17 hours. The reaction mixture was diluted with ethyl acetate and washed with brine and concentrated under reduced pressure. The residue was purified on column chromatography to obtain 6-{[(2-chloro-6-fluorophenyl)carbonyl]amino}-N-(3-chloro-2-methylphenyl)-2-{[2-(propan-2-yloxy)ethyl]amino}-1H-benzimidazole-4-carboxamide (41 mg) as pale yellow 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 (35 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-3b8df723e4254346944a8fc9adf2ab02
Source dataset
uspto-grants-2015_12
Patent number
US09216968B2

Reaction notes

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