HCID 58541964, compound → HCID 53237380, compound

HRID 1966724Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:34]=[CH:33][C:11]3[N:12]([C:29]([CH3:32])([CH3:31])[CH3:30])[C:13]([C:16]4[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=4[N:23]4[CH:27]=[N:26][C:25]([CH3:28])=[N:24]4)(O)[NH:14][C:10]=3[CH:9]=2)=[CH:4][N:3]=1>CO>[C:29]([N:12]1[C:11]2[CH:33]=[CH:34][C:8]([C:5]3[CH:4]=[N:3][C:2]([NH2:1])=[N:7][CH:6]=3)=[CH:9][C:10]=2[N:14]=[C:13]1[C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1[N:23]1[CH:27]=[N:26][C:25]([CH3:28])=[N:24]1)([CH3:32])([CH3:31])[CH3:30]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 5-(2-amino-pyrimidin-5-yl)-1-tert-butyl-2-[5-chloro-2-(3-methyl-1,2,4-triazol-1-yl)-phenyl]-2,3-dihydro-1H-benzimidazol-2-ol plus regiosiomer (25 mg) in MeOH (25 mL) is heated at 70° C. for 16 hours. The reaction mixture is allowed to cool to room temperature and is concentrated under reduced pressure. The residue is purified by silica gel flash column chromatography with 5% MeOH in CH2Cl2 as the eluent followed by further purification using a HPLC C-18 column with CH3CN (0.1% TFA) in H2O (0.1% TFA) as the eluent to afford 5-{1-tert-butyl-2-[5-chloro-2-(3-methyl-1,2,4-triazol-1-yl)-phenyl]-1H-benzimidazol-5-yl}-pyrimidin-2-ylamine (Example 37) (9 mg, 37%) as a white solid LCMS (ESMS): m/z 459.20 (M++1) and 5-{1-tert-butyl-2-[5-chloro-2-(5-methyl-1,2,4-triazol-1-yl)-phenyl]-1H-benzimidazol-5-yl}-pyrimidin-2-ylamine (Example 38) (6 mg, 25%) as a white solid. LCMS (ESMS): m/z 459.20 (M++1)

Workup

temperatureto cool to room temperature
concentrationis concentrated under reduced pressure
customThe residue is purified by silica gel flash column chromatography with 5% MeOH in CH2Cl2 as the eluent
customfollowed by further purification

Sources & evidence

ORD record: ord-2d95931b97894136912c509fbc18f653
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420655B2

Reaction notes

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