4-Fluorobenzoyl chloride → 8-Methoxy-2-(2-(4-fluorobenzamido)ethyl)-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole hydrochloride

HRID 5349

반응식

HRID 5349 반응식
[CH3:1][O:2][CH:3]1[CH:14]2[CH:10]([CH2:11][N:12]([CH2:15][CH2:16][NH2:17])[CH2:13]2)[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]1=2.[F:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([Cl:25])=[O:24])=[CH:21][CH:20]=1>C(Cl)Cl.C(N(CC)CC)C>[ClH:25].[CH3:1][O:2][CH:3]1[CH:14]2[CH:10]([CH2:11][N:12]([CH2:15][CH2:16][NH:17][C:23](=[O:24])[C:22]3[CH:26]=[CH:27][C:19]([F:18])=[CH:20][CH:21]=3)[CH2:13]2)[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]1=2

참가 물질

5

반응물 2

HCID 678794-Fluorobenzoyl chlorideHCID 197956898-Methoxy-2-(2-aminoethyl)-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

생성물 1

HCID 197956978-Methoxy-2-(2-(4-fluorobenzamido)ethyl)-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole hydrochloride

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8471Triethylamine용매

반응 조건

온도
-20 °C

실험 절차

The product from Example 17 (0.95 g) was dissolved in 50 ml methylene chloride and 1.5 ml triethyl amine. The solution was cooled to -20° C. and 0.59 ml p-fluorobenzoyl chloride was added. After 30 min, the reaction was quenched in 5% NaHCO3 and extracted with ethyl acetate. The organic extracts were dried (Na2SO4), evaporated, and the product was dissolved in ether and treated with ethereal HCl and then evaporated to dryness. The resulting product was recrystallized from ethyl acetate and ether to yield 0.772 g of the desired product as a white solid, mp: 197°-8° C. NMR (d6DMSO) δ2.60-3.10 (m, 3H), 3.00-3.50 (m, 4H), 3.59 (m, 2H), 3.78 (s, 3H), 3.82-4.22 (m, 3H), 6.83 (d, 1H), 6.87 (d, 1H), 7.23 (t, 1H), 7.34 (m, 2 H), 8.00 (m, 2H).

후처리

  1. customthe reaction was quenched in 5% NaHCO3
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic extracts were dried (Na2SO4)
  4. customevaporated
  5. dissolutionthe product was dissolved in ether
  6. additiontreated with ethereal HCl
  7. customevaporated to dryness
  8. customThe resulting product was recrystallized from ethyl acetate and ether

출처 및 근거

ORD 기록
ord-f54e63fe817945f5aca1b6509ef67a57
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05244888

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