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

HRID 1783897Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1783897
[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]

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-d51432f38f2c4258983d49f9195f03f3
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07501447B2

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