Methylamine → HCID 178482374, compound

HRID 491644Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[NH:13][C:12]3[CH:14]=[CH:15][C:16]([O:18][C:19]4[CH:24]=[CH:23][N:22]=[C:21](S(C)(=O)=O)[N:20]=4)=[CH:17][C:11]=3[N:10]=2)=[CH:4][C:3]=1[C:29]([F:32])([F:31])[F:30].[CH3:33][NH2:34]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[NH:13][C:12]3[CH:14]=[CH:15][C:16]([O:18][C:19]4[CH:24]=[CH:23][N:22]=[C:21]([NH:34][CH3:33])[N:20]=4)=[CH:17][C:11]=3[N:10]=2)=[CH:4][C:3]=1[C:29]([F:32])([F:31])[F:30]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of (4-chloro-3-trifluoromethyl-phenyl)-[5-(2-methanesulfonyl-pyrimidin-4-yloxy)-1H-benzimidazol-2-yl]-amine (Step B, 120 mg, 0.2 mmol, 1.0 eq.) in anhydrous THF (4 mL) was added 1 mL of 2 M CH3NH2 in THF (2 mmol, 10 eq). The solution was heated to 80° C. for 1 h. The THF was removed under reduced pressure and the crude was purified by column chromatography (0-10% MeOH/CH2Cl2 with 1% NH4OH) to yield pure (4-chloro-3-trifluoromethyl-phenyl)-[5-(2-methylamino-pyrimidin-4-yloxy)-1H-benzimidazol-2-yl]-amine. MS m/z=435.1 (M+H)+; MW Calc'd for C19H14ClF3N6O: 434.09.

Workup

customThe THF was removed under reduced pressure
customthe crude was purified by column chromatography (0-10% MeOH/CH2Cl2 with 1% NH4OH)

Sources & evidence

ORD record: ord-0bcea19a27624dedbc966d5062332b5b
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07531553B2

Reaction notes

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