Pivaloyl chloride → Methyl {2-tert-butyl-1-[(4,4-difluorocyclohexyl)methyl]-1H-benzimidazol-5-yl}carbamate

HRID 1987197Notes

Reaction equation

HRID 1987197 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:18][C:19](=[O:22])[O:20][CH3:21])[CH:5]=[CH:6][C:7]=1[NH:8][CH2:9][CH:10]1[CH2:15][CH2:14][C:13]([F:17])([F:16])[CH2:12][CH2:11]1.[CH3:23][C:24]([CH3:29])([CH3:28])[C:25](Cl)=O>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:24]([C:29]1[N:8]([CH2:9][CH:10]2[CH2:15][CH2:14][C:13]([F:17])([F:16])[CH2:12][CH2:11]2)[C:7]2[CH:6]=[CH:5][C:4]([NH:18][C:19](=[O:22])[O:20][CH3:21])=[CH:3][C:2]=2[N:1]=1)([CH3:28])([CH3:25])[CH3:23]

Participants

5

Reactant 2

HCID 62493Pivaloyl chlorideHCID 57723210HCID 57723210, compound

Product 1

HCID 57723214Methyl {2-tert-butyl-1-[(4,4-difluorocyclohexyl)methyl]-1H-benzimidazol-5-yl}carbamate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Methyl (3-amino-4-{[(4,4-difluorocyclohexyl)methyl]amino}phenyl)carbamate (185 mg, 0.590 mmol) and DMAP (15 mg, 0.118 mmol) were dissolved in 10 mL of DCM. Trimethylacetyl chloride (0.080 mL, 0.649 mmol) was added dropwise and the solution was stirred at rt for 2 h. The solution was washed with aqueous NaHCO3 solution, brine and dried over anhydrous MgSO4. The solvent was concentrated. The residue was dissolved in 4 mL of DCE and P2O5 (catalytic) was added and the solution was heated at 125° C. for 1 h using a Personal Chemistry microwave apparatus.

Workup

  1. washThe solution was washed with aqueous NaHCO3 solution, brine
  2. dry with materialdried over anhydrous MgSO4
  3. concentrationThe solvent was concentrated
  4. dissolutionThe residue was dissolved in 4 mL of DCE
  5. additionP2O5 (catalytic) was added
  6. temperaturethe solution was heated at 125° C. for 1 h

Sources & evidence

ORD record
ord-1442fd00a4344bbd8d23007b1672dc33
Source dataset
uspto-grants-2009_06
Patent number
US07550495B2

Reaction notes

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