(1R,2S)-Tranylcypromine → HCID 69314748, compound

HRID 1760541Notes

Reaction equation

HRID 1760541 reaction equation
[C:1]([O:4][C@@H:5]1[CH:11]=[CH:10][C@H:9]([N:12]2[C:16]3[N:17]=[C:18]([S:22][CH2:23][CH2:24][CH3:25])[N:19]=[C:20](Cl)[C:15]=3[N:14]=[N:13]2)[C:6]21[CH2:8][CH2:7]2)(=[O:3])[CH3:2].[C:26]1([C@@H:32]2[CH2:34][C@H:33]2[NH2:35])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.OC(C(O)C([O-])=O)C([O-])=O.C(N(CC)C(C)C)(C)C>ClCCl>[C:1]([O:4][C@@H:5]1[CH:11]=[CH:10][C@H:9]([N:12]2[C:16]3[N:17]=[C:18]([S:22][CH2:23][CH2:24][CH3:25])[N:19]=[C:20]([NH:35][C@@H:33]4[CH2:34][C@H:32]4[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[C:15]=3[N:14]=[N:13]2)[C:6]21[CH2:8][CH2:7]2)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 19493(1R,2S)-TranylcypromineHCID 81531DiisopropylethylamineHCID 38061142,3-DihydroxybutanedioateHCID 87780202HCID 87780202, compound

Product 1

HCID 69314748HCID 69314748, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product of step f) (0.5 g) and (1R-trans)-2-phenyl-cyclopropanamine, [R-(R*,R*)]-2,3-dihydroxybutanedioate (1:1) (prepared as described by L. A. Mitscher et al., J. Med. Chem. 1986, 29, 2044) (0.4 g) in dichloromethane (50 ml) was added N,N-diisopropylethylamine (2 ml) and the resulting solution was stirred and heated at reflux for 3 hours. The reaction mixture was concentrated to dryness under reduced pressure and purified by chromatography (SiO2; 4:1 isohexane:ethyl acetate) to give the subtitle compound (0.6 g).

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 hours
  3. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  4. custompurified by chromatography (SiO2; 4:1 isohexane:ethyl acetate)

Sources & evidence

ORD record
ord-66f48a721a0549c3aee4b38aca7e1b56
Source dataset
uspto-grants-2005_01
Patent number
US06844348B2

Reaction notes

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