Diisopropylethylamine → 3-Cyclohexyl-5-ethoxy-1,3-dihydro-1-[2-methoxy-4-[N-(2-dimethylamino-1,1-dimethylethyl)carbamoyl]benzyl]-2H-benzimidazol-2-one

HRID 2258546

Reaktionsgleichung

Reaktionsgleichung von HRID 2258546
[C:1]([NH:5][C:6]([C:8]1[CH:33]=[CH:32][C:11]([CH2:12][N:13]2[C:17]3[CH:18]=[CH:19][C:20]([O:22][CH2:23][CH3:24])=[CH:21][C:16]=3[N:15]([CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[C:14]2=[O:31])=[C:10]([O:34][CH3:35])[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:36][N:37](C)[CH2:38]C(N)(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH:25]1([N:15]2[C:16]3[CH:21]=[C:20]([O:22][CH2:23][CH3:24])[CH:19]=[CH:18][C:17]=3[N:13]([CH2:12][C:11]3[CH:32]=[CH:33][C:8]([C:6](=[O:7])[NH:5][C:1]([CH3:4])([CH3:2])[CH2:3][N:37]([CH3:38])[CH3:36])=[CH:9][C:10]=3[O:34][CH3:35])[C:14]2=[O:31])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 226843(2-Amino-2-methylpropyl)dimethylamineHCID 229224911-[4-(N-tert-Butylcarbamoyl)-2-methoxybenzyl]-3-cyclohexyl-5-ethoxy-1,3-dihydro-2H-benzimidazol-2-one

Produkt 1

HCID 229225653-Cyclohexyl-5-ethoxy-1,3-dihydro-1-[2-methoxy-4-[N-(2-dimethylamino-1,1-dimethylethyl)carbamoyl]benzyl]-2H-benzimidazol-2-oneAusbeute 9,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 1.5 g of the compound obtained in Example 15 Step B, 1 g of 2-dimethylamino-1,1-dimethylethylamine (synthesized according to J. Am. Chem. Soc., 1946, 68, 12-14), 1.6 g of BOP and 2 g of DIPEA in 20 ml of DCM is left stirring for 1 hour at RT. The reaction mixture is concentrated under vacuum, the residue is extracted with EtOAc, the organic phase is washed with 1N NaOH solution, with water and dried over Na2SO4, and the solvent is evaporated off under vacuum. The residue is chromatographed on silica, eluting with a DCM/MeOH mixture (98/2; v/v). 0.15 g of the expected product is obtained after crystallization from iso ether, mp=161° C.

Aufarbeitung

  1. waitis left
  2. concentrationThe reaction mixture is concentrated under vacuum
  3. extractionthe residue is extracted with EtOAc
  4. washthe organic phase is washed with 1N NaOH solution, with water
  5. dry with materialdried over Na2SO4
  6. customthe solvent is evaporated off under vacuum
  7. customThe residue is chromatographed on silica
  8. washeluting with a DCM/MeOH mixture (98/2; v/v)

Quellen und Nachweise

ORD-Eintrag
ord-34fee72ea51d494195a7bcb32bf1ea19
Quelldatensatz
uspto-grants-1997_08
Patentnummer
US05661169

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