Morpholine → Methyl 1-(2-fluorophenyl)-5-(morpholin-4-ylmethyl)-1H-1,2,3-triazole-4-carboxylate

HRID 219562

반응식

HRID 219562 반응식
[N:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[F:10])=[N+:2]=[N-:3].Cl[CH2:12][C:13](=O)[CH2:14][C:15]([O:17][CH3:18])=[O:16].[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1>>[F:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N:1]1[C:13]([CH2:12][N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[C:14]([C:15]([O:17][CH3:18])=[O:16])[N:3]=[N:2]1

참가 물질

4

반응물 3

HCID 8083MorpholineHCID 36240Methyl 4-chloroacetoacetateHCID 116079241-Azido-2-fluorobenzene

생성물 1

HCID 68649638Methyl 1-(2-fluorophenyl)-5-(morpholin-4-ylmethyl)-1H-1,2,3-triazole-4-carboxylate

실험 절차

A solution of 1-azido-2-fluorobenzene, prepared according to Platz, M. S. et al. J. Org. Chem. 1989, 54, 5938-5945 (500 mg; 3.65 mmol; 1 eq.) and methyl 4-chloroacetoacetate (823 mg; 5.47 mmol; 1.5 eq.) in morpholine (10 ml) was stirred at 50° C. overnight. The reaction mixture was evaporated. Water was added (20 mL) and was extracted with EtOAc (2×20 mL). Combined organic phases were extracted with 3 portions of HCl 1 N. Combined aqueous phases were made alkaline with NaOH 5N and were extracted with EtOAc (3×20 mL). Organic layers were dried over magnesium sulfate and evaporated, affording the title product as a dark red oil. It was used in the next step without further purification. HPLC (Method A) Rt 1.81 min. (Purity: 82.5%).

후처리

  1. customThe reaction mixture was evaporated
  2. additionWater was added (20 mL)
  3. extractionwas extracted with EtOAc (2×20 mL)
  4. extractionCombined organic phases were extracted with 3 portions of HCl 1 N
  5. extractionwere extracted with EtOAc (3×20 mL)
  6. dry with materialOrganic layers were dried over magnesium sulfate
  7. customevaporated

출처 및 근거

ORD 기록
ord-d420a75a5add4873a536843d43ff921c
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202856B2

연결된 노트

불러오는 중…