Hydrochloric Acid → Cgp-20712

HRID 638061ノート

反応式

HRID 638061 の反応式
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]

参加物

7

反応物 6

HCID 313Hydrochloric Acid2 回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

生成物 1

HCID 2685Cgp-20712

実験手順

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°.

後処理

  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

出典と根拠

ORDレコード
ord-3daa54ff2b804767ae4f00ba3da46064
出典データセット
uspto-grants-1985_12
特許番号
US04559354

反応ノート

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