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Tyramine → 10-[(4-Chlorophenoxy)acetyl]-N-[2-(4-hydroxyphenyl)ethyl]-10,11-dihydro-5H-pyrrolo[2,1-C][1,4]benzodiazepine-3-carboxamide

HRID 639270
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HRID 639270 반응식
ClC(Cl)(Cl)[C:3]([C:5]1[N:14]2[C:8]([CH2:9][N:10]([C:19](=[O:29])[CH2:20][O:21][C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[CH2:13]2)=[CH:7][CH:6]=1)=[O:4].[NH2:32][CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][CH:36]=1>CS(C)=O.C(#N)C>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([O:21][CH2:20][C:19]([N:10]2[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[CH2:13][N:14]3[C:5]([C:3]([NH:32][CH2:33][CH2:34][C:35]4[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][CH:36]=4)=[O:4])=[CH:6][CH:7]=[C:8]3[CH2:9]2)=[O:29])=[CH:23][CH:24]=1
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참가 물질

5

반응물 2

HCID 5610TyramineHCID 160392192,2,2-trichloro-1-{10-[(4-chlorophenoxy)acetyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanone

생성물 1

HCID 1603922010-[(4-Chlorophenoxy)acetyl]-N-[2-(4-hydroxyphenyl)ethyl]-10,11-dihydro-5H-pyrrolo[2,1-C][1,4]benzodiazepine-3-carboxamide

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 6342
Acetonitrile
용매

실험 절차

A solution of 2,2,2-trichloro-1-{10-[(4-chlorophenoxy)acetyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanone of Example 67 (0.3 mmol) and tyramine (0.62 mmol) in dimethylsulfoxide (0.2 mL) and acetonitrile (4 mL) was stirred at 80° C. for 18 hours. The solvents were evaporated and the residue was dissolved in dichloromethane, washed with water, dried over anhydrous sodium sulfate and evaporated. The compound was purified by HPLC (normal phase, Luna® CN bonded packing) and crystallized from ethyl acetate/hexane (0.12 g), m.p. 206-207 ° C. MS [(+)ESI, m/z]: 516 [M+H]+ Anal. Calcd for C29H26CIN3O4: C, 67.50; H, 5.08; N, 8.14. Found: C, 67.35; H, 5.07; N, 8.08.

후처리

  1. customThe solvents were evaporated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. customThe compound was purified by HPLC (normal phase, Luna® CN bonded packing)
  7. customcrystallized from ethyl acetate/hexane (0.12 g), m.p. 206-207 ° C

출처 및 근거

ORD 기록
ord-5e3a4df184c34a19bd6a3e3c6d43f46b
출처 데이터셋
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07691848B2

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