HCID 58541965, compound → HCID 58541933, compound

HRID 1966747Notes

Reaction equation

HRID 1966747 reaction equation
C([O:3][C:4](=[O:38])[CH2:5][N:6]1[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]2[N:21]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:20]3[CH:26]=[CH:27][C:28]([C:30]4[CH:31]=[N:32][C:33]([NH2:36])=[N:34][CH:35]=4)=[CH:29][C:19]=3[N:18]=2)=[N:9][C:8]([CH3:37])=[N:7]1)C>C(#N)C>[NH2:36][C:33]1[N:34]=[CH:35][C:30]([C:28]2[CH:27]=[CH:26][C:20]3[N:21]([C:22]([CH3:23])([CH3:24])[CH3:25])[C:17]([C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=4[C:10]4[N:6]([CH2:5][C:4]([OH:38])=[O:3])[N:7]=[C:8]([CH3:37])[N:9]=4)=[N:18][C:19]=3[CH:29]=2)=[CH:31][N:32]=1

Participants

3

Reactant 1

HCID 58541965HCID 58541965, compound

Product 1

HCID 58541933HCID 58541933, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(5-{2-[5-(2-Amino-pyrimidin-5-yl)-1-tert-butyl-1H-benzimidazol-2-yl]-phenyl}-3-methyl-1,2,4-triazol-1-yl)-acetic acid ethyl ester (40 mg, 0.078 mmol) and Amberlyst A26 (OH− form) (450 mg, 0.6 mmol) are combined in acetonitrile (5 mL) and the mixture is agitated for 3 hours, filtered, and the isolate is washed with acetonitrile (2×5 mL). The product is purified by silica gel flash column chromatography eluting with 20% formic acid in acetonitrile (1 mL). The eluent is concentrated to afford the title compound (37 mg, 38%) LCMS (ESMS): m/z 483.2 (M++1)

Workup

  1. filtrationfiltered
  2. washthe isolate is washed with acetonitrile (2×5 mL)
  3. customThe product is purified by silica gel flash column chromatography
  4. washeluting with 20% formic acid in acetonitrile (1 mL)
  5. concentrationThe eluent is concentrated

Sources & evidence

ORD record
ord-9bbe77ae5f1d4461bb918984f4fe7b86
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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