Hydrochloric Acid → Cgp-20712

HRID 638061Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 638061
Cl.[NH2:2][CH2:3][CH:4]([OH:23])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]([CH3:22])[CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[N:17]=2)=[CH:9][CH:8]=1.[OH-:24].[K+].[CH3:26][C:27]1(C)NC(=O)[C:30]2[CH:34]=[CH:35][C:36](OCC=O)=[CH:37][C:29]=2[O:28]1.[C:43]([BH3-])#[N:44].[Na+].C[OH:48]>>[C:43]([C:34]1[CH:30]=[C:29]([CH:37]=[CH:36][C:35]=1[OH:48])[O:28][CH2:27][CH2:26][NH:2][CH2:3][CH:4]([OH:23])[CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[N:14]([CH3:22])[CH:15]=[C:16]([C:18]([F:21])([F:19])[F:20])[N:17]=2)=[CH:11][CH:12]=1)(=[O:24])[NH2:44]

Komponenten

7

Edukt 6

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 14797Potassium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 202550972,3-dihydro-2,2-dimethyl-7-(2-oxoethoxy)-4H-1,3-benzoxazin-4-oneHCID 202551961-amino-3-[4-(1-methyl-4-(trifluoromethyl)-1H-imidazol-2-yl)-phenoxy]-2-propanol

Produkt 1

HCID 2685Cgp-20712

Versuchsvorschrift

4.28 ml of 5.9N methanolic hydrochloric acid are added to a solution of 8.39 g of 1-amino-3-[4-(1-methyl-4-(trifluoromethyl)-1H-imidazol-2-yl)-phenoxy]-2-propanol in 250 ml of methanol. The pH is adjusted to 8-9 by the addition of solid potassium hydroxide; there are subsequently added 25 g of molecular sieve (pore size 3 Å), 5.6 g of 2,3-dihydro-2,2-dimethyl-7-(2-oxoethoxy)-4H-1,3-benzoxazin-4-one and finally 0.59 g of sodium cyanoborohydride. The mixture, containing the corresponding Schiff's base, is stirred under reflux at room temperature for 18 hours and, after the addition of 50 ml of 5.9N methanolic hydrochloric acid, for a further one hour, filtered and the solvent is removed in a rotary evaporator. The residue is chromatographed on silica gel with a mixture of chloroform/methanol/ammonia (40:50:5), the main fractions are freed of solvent and the residue is recrystallised from methanol, yielding 1-[2-(3 -carbamoyl-4-hydroxyphenoxy)-ethylamino]-3-[4-[1-methyl-4-(trifluoromethyl)-1H-imidazol-2-yl]-phenoxy]-2-propanol having a melting point of 195°-197°.

Aufarbeitung

  1. filtrationfiltered
  2. customthe solvent is removed in a rotary evaporator
  3. customThe residue is chromatographed on silica gel with a mixture of chloroform/methanol/ammonia (40:50:5)
  4. customthe residue is recrystallised from methanol

Quellen und Nachweise

ORD-Eintrag
ord-3daa54ff2b804767ae4f00ba3da46064
Quelldatensatz
uspto-grants-1985_12
Patentnummer
US04559354

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