Phosphorus oxychloride → 5-Chloro-2-(morpholin-4-ylmethyl)-7-[4-(trifluoromethyl)phenyl][1,2,4]triazolo[1,5-c]pyrimidine

HRID 2171552ノート

反応式

HRID 2171552 の反応式
[N:1]1([CH2:7][C:8]2[N:16]=[C:15]3[N:10]([C:11](O)=[N:12][C:13]([C:17]4[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=4)=[CH:14]3)[N:9]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(=O)(O)[O-].[Na+].P(Cl)(Cl)([Cl:35])=O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[Cl:35][C:11]1[N:10]2[N:9]=[C:8]([CH2:7][N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)[N:16]=[C:15]2[CH:14]=[C:13]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)[N:12]=1

参加物

5

反応物 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178517471HCID 178517471、化合物

生成物 1

HCID 593131385-Chloro-2-(morpholin-4-ylmethyl)-7-[4-(trifluoromethyl)phenyl][1,2,4]triazolo[1,5-c]pyrimidine

試薬・触媒・溶媒 1

HCID 66133Benzyl triethylammonium chloride触媒

反応条件

温度
120 °C

実験手順

850 mg (2.2 mmol) of 2-(morpholin-4-ylmethyl)-7-[4-(trifluoromethyl)phenyl][1,2,4]triazolo-[1,5-c]pyrimidin-5-ol (Example 135A) are introduced into phosphoryl chloride (20 ml), 1.98 g (8.7 mmol) of benzyltriethylammonium chloride are added, and the reaction mixture is stirred at 120° C. for 2 h. The reaction mixture is slowly poured, while stirring vigorously, into ice-water, and solid sodium bicarbonate is added until a pH of 8 is reached. The reaction mixture is extracted with ethyl acetate (150 ml), and the organic phase is separated off, dried (magnesium sulphate) and concentrated. The residue is chromatographed on silica gel (mobile phase dichloromethane/ethanol 100:1 to 20:1). 650 mg (75% of theory) of the product are obtained as a solid.

後処理

  1. additionare added
  2. additionThe reaction mixture is slowly poured
  3. additionis added until a pH of 8
  4. extractionThe reaction mixture is extracted with ethyl acetate (150 ml)
  5. customthe organic phase is separated off
  6. dry with materialdried (magnesium sulphate)
  7. concentrationconcentrated
  8. customThe residue is chromatographed on silica gel (mobile phase dichloromethane/ethanol 100:1 to 20:1)
  9. custom650 mg (75% of theory) of the product are obtained as a solid

出典と根拠

ORDレコード
ord-f93aea2ae6ad4779bc1961212b0cd302
出典データセット
uspto-grants-2015_06
特許番号
US09051323B2

反応ノート

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