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

HRID 1081516Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1081516
[CH2:1]([O:3][C:4]1[CH:33]=[CH:32][C:7]2[N:8]([S:18]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([OH:29])=O)=[CH:23][C:22]=3[O:30][CH3:31])(=[O:20])=[O:19])[C:9](=[O:17])[N:10]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)[C:6]=2[CH:5]=1)[CH3:2].[CH3:34][N:35]([CH3:41])[CH2:36][C:37]([NH2:40])([CH3:39])[CH3:38].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:11]1([N:10]2[C:6]3[CH:5]=[C:4]([O:3][CH2:1][CH3:2])[CH:33]=[CH:32][C:7]=3[N:8]([S:18]([C:21]3[CH:26]=[CH:25][C:24]([C:27](=[O:29])[NH:40][C:37]([CH3:39])([CH3:38])[CH2:36][N:35]([CH3:41])[CH3:34])=[CH:23][C:22]=3[O:30][CH3:31])(=[O:19])=[O:20])[C:9]2=[O:17])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 226843(2-Amino-2-methylpropyl)dimethylamineHCID 152290425-Ethoxy-1,3-dihydro-1-(2-methoxy-4-carboxybenzenesulfonyl)-3-cyclohexyl-2H-benzimidazol-2-one

Produkt 1

HCID 233642313-Cyclohexyl-5-ethoxy-1,3-dihydro-1-[2-methoxy-4-[N-(2-dimethylamino-1,1-dimethylethyl)carbamoyl]benzenesulfonyl]-2H-benzimidazol-2-oneAusbeute 53,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 1 g of the compound obtained in EXAMPLE 13, 1 g of 2-dimethylamino -1,1- dimethylethylamine (synthesized according to J. Am. Chem. Soc., 1946, 68, 10-12), 1 g of BOP, 1 ml of DIPEA and 20 ml of DCM is stirred for 16 hours at RT. The reaction mixture is evaporated under vacuum, the residue is extracted with AcOEt, washed with a 1N solution of NaOH, extracted with a 6N solution of HCl, washed with AcOEt, the acidic aqueous phase is rendered alkaline by the addition of 2N NaOH, extracted with AcOEt and dried over Na2SO4 and the solvent is evaporated off under vacuum. The residue is chromatographed on silica using a DCM/MeOH mixture (99/1; v/v) as the eluent to give 0.65 g of the expected product after crystallization from iso ether. M.p.=161° C.

Aufarbeitung

  1. customThe reaction mixture is evaporated under vacuum
  2. extractionthe residue is extracted with AcOEt
  3. washwashed with a 1N solution of NaOH
  4. extractionextracted with a 6N solution of HCl
  5. washwashed with AcOEt
  6. additionby the addition of 2N NaOH
  7. extractionextracted with AcOEt
  8. dry with materialdried over Na2SO4
  9. customthe solvent is evaporated off under vacuum
  10. customThe residue is chromatographed on silica using a DCM/MeOH mixture (99/1; v/v) as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-a22e3644e0034c9ba4f7b23107f49fd2
Quelldatensatz
uspto-grants-1996_12
Patentnummer
US05585394

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