Ethanol → 3-[5-(2-Amino-pyrimidin-5-yl)-1-tert-butyl-1H-benzimidazol-2-yl]-4-1,2,4-triazol-1-yl-benzoic acid

HRID 1966746Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:33]=[CH:32][C:11]3[N:12]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:13]([C:15]4[CH:16]=C([CH:20]=[CH:21][C:22]=4[N:23]4[CH:27]=[N:26][CH:25]=[N:24]4)C#N)=[N:14][C:10]=3[CH:9]=2)=[CH:4][N:3]=1.[OH-:34].[K+].[CH3:36][CH2:37][OH:38]>O>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:33]=[CH:32][C:11]3[N:12]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:13]([C:15]4[CH:16]=[C:36]([CH:20]=[CH:21][C:22]=4[N:23]4[CH:27]=[N:26][CH:25]=[N:24]4)[C:37]([OH:34])=[O:38])=[N:14][C:10]=3[CH:9]=2)=[CH:4][N:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 3-[5-(2-amino-pyrimidin-5-yl)-1-tert-butyl-1H-benzimidazol-2-yl]-4-1,2,4-triazol-1-yl-benzonitrile (Example 7) (400 mg, 0.92 mmol) in EtOH (10 mL) is added KOH (103 mg, 1.8 mmol) in H2O (1 mL) at room temperature. The mixture is heated to 80° C. for 48 hours. The solution is cooled down and is concentrated under vacuum. The residue is dissolved in H2O (10 mL) and the pH of the solution is adjusted to 6 with 2M HCl solution. The white solid that precipitates out from the solution is collected by filtration. The white solid is dried under vacuum providing the title compound. LCMS (ESMS): m/z 455.20 (M++1)

Workup

temperatureThe solution is cooled down
concentrationis concentrated under vacuum
dissolutionThe residue is dissolved in H2O (10 mL)
customThe white solid that precipitates out from the solution
filtrationis collected by filtration
customThe white solid is dried under vacuum

Sources & evidence

ORD record: ord-354e54afbd2d4a1c9f4d849a813b6673
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420655B2

Reaction notes

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