2,2-Dimethylbutyryl chloride → HCID 57591005, compound

HRID 1783896Notes

Reaction equation

HRID 1783896 reaction equation
[CH3:1][C:2]([CH3:8])([CH2:6][CH3:7])[C:3](Cl)=[O:4].Cl.[CH:10]1([CH2:16][N:17]2[C:21]3[CH:22]=[CH:23][C:24]([NH2:26])=[CH:25][C:20]=3[N:19]=[C:18]2[C:27]([CH3:31])([CH3:30])[CH2:28][CH3:29])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>CN(C1C=CN=CC=1)C.C(#N)C.CCOC(C)=O>[CH:10]1([CH2:16][N:17]2[C:21]3[CH:22]=[CH:23][C:24]([NH:26][C:3](=[O:4])[C:2]([CH3:8])([CH3:1])[CH2:6][CH3:7])=[CH:25][C:20]=3[N:19]=[C:18]2[C:27]([CH3:30])([CH3:31])[CH2:28][CH3:29])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1

Participants

6

Reactant 2

HCID 799582,2-Dimethylbutyryl chlorideHCID 68861536HCID 68861536, compound

Product 1

HCID 57591005HCID 57591005, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

2,2-Dimethylbutyryl chloride (24.6 mg, 0.18 mmol) was added to a mixture of 1-(cyclohexylmethyl)-2-(1,1-dimethylpropyl)-1H-benzimidazol-5-amine hydrochloride (65.0 mg, 0.15 mmol) (for preparation see in Example 7, step B) and DMAP (73.3 mg, 0.60 mmol) in acetonitrile (5 mL) at 0° C. The mixture was stirred for 6 h at room temperature, diluted with EtOAc (50 mL), washed with saturated NaHCO3 aqueous solution (10 mL), saturated NaCl aqueous solution (10 mL) and dried over Na2SO4. After filtration and evaporation, the residue was purified by MPLC (EtOAc as eluent on silica gel) to give the desired title compound as a syrup (51.6 mg, 87%). 1H NMR (400 MHz, CD3OD): δ 0.84 (t, J=7.52 Hz, 3H), 0.91 (t, J=7.52 Hz, 3H), 1.25 (m, 5H), 1.28 (s, 6H), 1.64 (m, 3H), 1.67 (s, 6H), 1.72 (q, J=7.49 Hz, 2H), 1.78 (m, 2H), 2.02 (q, J=7.49 Hz, 2H), 2.13 (m, 1H), 4.45 (d, J=7.62 Hz, 2H), 7.64 (dd, J=8.98, 1.76 Hz, 1H), 7.85 (d, J=9.18 Hz, 1H), 8.34 (s, 1H). MS (ESI) (M+H)+: 398.3. Anal. Calcd for C25H39N3O+1.50 TFA+0.70H2O (581.25): C, 57.86; H, 7.27; N, 7.23. Found: C, 57.90; H, 7.19; N, 7.34.

Workup

  1. washwashed with saturated NaHCO3 aqueous solution (10 mL), saturated NaCl aqueous solution (10 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationAfter filtration and evaporation
  4. customthe residue was purified by MPLC (EtOAc as eluent on silica gel)

Sources & evidence

ORD record
ord-aba0c9350b3d445eba5866611aea8a27
Source dataset
uspto-grants-2009_03
Patent number
US07501447B2

Reaction notes

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