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

HRID 1783897노트

반응식

HRID 1783897 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d51432f38f2c4258983d49f9195f03f3
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07501447B2

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