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

HRID 2389818노트

반응식

HRID 2389818 반응식
[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

참가 물질

5

반응물 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178517471HCID 178517471, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 66133Benzyl triethylammonium chloride촉매

반응 조건

온도
120 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-84ee823158044240bf2b6cf9f15c8370
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08273752B2

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