Diisopropylethylamine → HCID 71267450, compound

HRID 1505800Notes

Reaction equation

HRID 1505800 reaction equation
Cl[C:2]1[NH:6][C:5]2[CH:7]=[C:8]([NH:22][C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]([F:34])([F:33])[F:32])=[O:24])[CH:9]=[C:10]([C:11]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:15]=3[CH3:21])=[O:12])[C:4]=2[N:3]=1.Cl.[NH:36]1[CH2:39][CH2:38][CH2:37]1.C(N(CC)C(C)C)(C)C>CCO>[N:36]1([C:2]2[NH:6][C:5]3[CH:7]=[C:8]([NH:22][C:23]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[C:31]([F:32])([F:33])[F:34])=[O:24])[CH:9]=[C:10]([C:11]([NH:13][C:14]4[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:15]=4[CH3:21])=[O:12])[C:4]=3[N:3]=2)[CH2:39][CH2:38][CH2:37]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 12308726Azetidine hydrochlorideHCID 71267437HCID 71267437, compound

Product 1

HCID 71267450HCID 71267450, compoundYield 32.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-chloro-N-(3-chloro-2-methylphenyl)-6-({[2-(trifluoromethyl)phenyl]carbonyl}amino)-1H-benzimidazole-4-carboxamide (80 mg, Example 135), azetidine hydrochloride (60 mg) and N,N-diisopropylethylamine (208 μL) in EtOH (1.8 mL) was reacted at 120° C. for 20 minutes in a microwave reactor (Biotage, Initiator). The reaction mixture was concentrated under reduced pressure, and the residue was purified on column chromatography to obtain 2-(azetidin-1-yl)-N-(3-chloro-2-methylphenyl)-6-({[2-(trifluoromethyl)phenyl]carbonyl}amino)-1H-benzimidazole-4-carboxamide (27 mg). This was dissolved in MeOH (1 mL), 2N hydrogen chloride/MeOH 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 (21 mg) as white powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified on column chromatography

Sources & evidence

ORD record
ord-c3d87b1decac41a986bd123c33361205
Source dataset
uspto-grants-2015_12
Patent number
US09216968B2

Reaction notes

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