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

HRID 639270Notes

Reaction equation

HRID 639270 reaction equation
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

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5e3a4df184c34a19bd6a3e3c6d43f46b
Source dataset
uspto-grants-2010_04
Patent number
US07691848B2

Reaction notes

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