Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → 1-[1-(8,9-dimethyl-9H-purin-6-yl)piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one

HRID 528030Notes

Reaction equation

HRID 528030 reaction equation
[NH2:1][C:2]1[C:3]([N:10]2[CH2:15][CH2:14][CH:13]([N:16]3C4C=CC=CC=4[NH:18][C:17]3=[O:25])[CH2:12][CH2:11]2)=[N:4][CH:5]=[N:6][C:7]=1[NH:8][CH3:9].[C:26]12(CS(O)(=O)=O)C(C)(C)[CH:30]([CH2:31][CH2:32]1)[CH2:29][C:27]2=O.[CH3:41][C:42](C)(C)C([O-])([O-])[O-]>C(#N)C>[CH3:41][C:42]1[N:8]([CH3:9])[C:7]2[C:2]([N:1]=1)=[C:3]([N:10]1[CH2:11][CH2:12][CH:13]([N:16]3[C:27]4[CH:29]=[CH:30][CH:31]=[CH:32][C:26]=4[NH:18][C:17]3=[O:25])[CH2:14][CH2:15]1)[N:4]=[CH:5][N:6]=2

Participants

5

Reactant 3

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 21927715TrimethylorthoacetateHCID 668022691-(1-(5-amino-6-(methylamino)pyrimidin-4-yl)piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one

Product 1

HCID 668017311-[1-(8,9-dimethyl-9H-purin-6-yl)piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-oneYield 385%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 1-{1-[5-amino-6-(methylamino)pyrimidin-4-yl]piperidin-4-yl}-1,3-dihydro-2H-benzimidazol-2-one (150 mg, 0.442 mmol) in acetonitrile (2 mL) was added camphorsulfonic acid (4.9 mg, 0.02 mmol) and trimethylorthoacetate (2 mL, 16.6 mmol). The mixture was heated at reflux for 15 h, then was cooled to ambient and was purified by preparative-HPLC to afford 1-[1-(8,9-dimethyl-9H-purin-6-yl)piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one as a beige solid (28 mg, 0.077 mmol, 17% yield).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 15 h
  3. temperaturewas cooled to ambient and
  4. customwas purified by preparative-HPLC

Sources & evidence

ORD record
ord-a7bb55dee08a4083a18b32277d3d07d8
Source dataset
uspto-grants-2016_05
Patent number
US09346807B2

Reaction notes

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