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Pivaloyl chloride → Methyl [2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]carbamate

HRID 1987192
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1987192
[NH2:1][C:2]1[CH:3]=[C:4]([NH:16][C:17](=[O:20])[O:18][CH3:19])[CH:5]=[CH:6][C:7]=1[NH:8][CH2:9][CH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.[CH3:21][C:22]([CH3:27])([CH3:26])[C:23](Cl)=O>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:22]([C:27]1[N:8]([CH2:9][CH:10]2[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)[C:7]2[CH:6]=[CH:5][C:4]([NH:16][C:17](=[O:20])[O:18][CH3:19])=[CH:3][C:2]=2[N:1]=1)([CH3:26])([CH3:23])[CH3:21]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 62493Pivaloyl chlorideHCID 57723219Methyl {3-amino-4-[(tetrahydro-2H-pyran-4-ylmethyl)amino]phenyl}carbamate

Produkt 1

HCID 57723208Methyl [2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]carbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344Dichloromethane
Lösungsmittel

Versuchsvorschrift

Methyl {3-amino-4-[(tetrahydro-2H-pyran-4-ylmethyl)amino]phenyl}carbamate (2.29 g, 8.20 mmol) and DMAP (0.20 g, 1.64 mmol) were dissolved in 75 mL of DCM. Trimethylacetyl chloride (1.10 mL, 9.02 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 residue was dissolved in 25 mL of AcOH and was heated at 125° C. for 1 h using a Personal Chemistry microwave apparatus. The solvent was evaporated. The residue was dissolved in EtOAc and washed with aqueous NaHCO3 solution, brine and dried over anhydrous MgSO4. The crude product was purified by silica gel flash chromatography using 4:3/hexanes: acetone as eluent. Yield: 1.81 g (64%). 1H NMR (400 MHz, CHLOROFORM-D) δ 1.48-1.54 (m, 4 H), 1.56 (s, 9 H), 2.23-2.35 (m, 1 H), 3.27-3.35 (m, 2 H), 3.78 (s, 3 H), 3.96 (t, J=2.93 Hz, 1 H), 3.99 (t, J=3.03 Hz, 1 H), 4.18 (d, J=7.42 Hz, 2 H), 6.63 (br.s, 1 H), 7.24-7.28 (m, 1 H), 7.41 (br.s, 1 H), 7.61 (d, J=1.95 Hz, 1 H).

Aufarbeitung

  1. washThe solution was washed with aqueous NaHCO3 solution, brine
  2. dry with materialdried over anhydrous MgSO4
  3. dissolutionThe residue was dissolved in 25 mL of AcOH
  4. temperaturewas heated at 125° C. for 1 h
  5. customThe solvent was evaporated
  6. dissolutionThe residue was dissolved in EtOAc
  7. washwashed with aqueous NaHCO3 solution, brine
  8. dry with materialdried over anhydrous MgSO4
  9. customThe crude product was purified by silica gel flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bf3b00f7917943e19b5e0edcf4d7b325
Quelldatensatz
uspto-grants-2009_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07550495B2

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