Pivaloyl chloride → N-[2-tert-butyl-1-(cyclohexylmethyl)-1H-benzimidazol-5-yl]acetamide

HRID 1783897Notes

Reaction equation

HRID 1783897 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:16][C:17](=[O:19])[CH3:18])[CH:5]=[CH:6][C:7]=1[NH:8][CH2:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.[CH3:20][C:21]([CH3:26])([CH3:25])[C:22](Cl)=O>CN(C1C=CN=CC=1)C.ClCCl>[C:21]([C:26]1[N:8]([CH2:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[C:7]2[CH:6]=[CH:5][C:4]([NH:16][C:17](=[O:19])[CH3:18])=[CH:3][C:2]=2[N:1]=1)([CH3:25])([CH3:22])[CH3:20]

Participants

5

Reactant 2

HCID 62493Pivaloyl chlorideHCID 57591000N-{3-amino-4-[(cyclohexylmethyl)amino]phenyl}acetamide

Product 1

HCID 11232689N-[2-tert-butyl-1-(cyclohexylmethyl)-1H-benzimidazol-5-yl]acetamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Following the same procedure of Example 6, a mixture of N-{3-amino-4-[(cyclohexylmethyl)amino]phenyl}acetamide (1.57 g, 6.0 mmol) (for preparation see in Example 6, step D) and DMAP (0.15 g, 1.2 mmol) in dichloromethane (70 mL) was treated with trimethylacetyl choride (0.83 g, 6.6 mmol) at −10° C. After evaporation of the solvent, the residue was dissolved in 1,2-dichloroethane (40 mL) and then divided into eight Teflon-capped test tubes. The vessels were irradiated by microwave for 2 h at 170° C. After purification by MPLC (EtOAc as eluent on silica gel), the desired title compound was obtained as a white solid (1.42 g, 72%). 1H NMR (400 MHz, CD3OD): δ 1.24 (m, 5H), 1.64 (m, 2H), 1.67 (s, 9H), 1.70 (m, 1H), 1.77 (m, 2H), 2.12 (m, 1H), 2.18 (s, 3H), 4.45 (d, J=7.62 Hz, 2H), 7.50 (m, 1H), 7.84 (d, J=8.98 Hz, 1H), 8.43 (d, J=1.95 Hz, 1H). MS (ESI) (M+H)+: 328.3. Anal. Calcd for C20H29N3O+1.20 TFA+0.30H2O (469.71): C, 57.28; H, 6.61; N, 8.95. Found: C, 57.34; H. 6.67; N, 8.85.

Workup

  1. customAfter evaporation of the solvent
  2. dissolutionthe residue was dissolved in 1,2-dichloroethane (40 mL)
  3. customcapped test tubes
  4. customThe vessels were irradiated by microwave for 2 h at 170° C
  5. customAfter purification by MPLC (EtOAc as eluent on silica gel)

Sources & evidence

ORD record
ord-d51432f38f2c4258983d49f9195f03f3
Source dataset
uspto-grants-2009_03
Patent number
US07501447B2

Reaction notes

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