HCID 69214710, compound → HCID 508915, compound

HRID 279266Notes

Reaction equation

HRID 279266 reaction equation
[NH2:1][C:2]1[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][C:3]=1[C:4]([NH:6][CH2:7][C:8]([NH:10][C@@H:11]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2[CH:22]=[C:21]3[O:23][CH2:24][O:25][C:20]3=[CH:19][C:18]=2[N+:26]([O-])=O)[CH2:12]1)=[O:9])=[O:5]>[Pd].CO>[NH2:26][C:18]1[CH:19]=[C:20]2[O:25][CH2:24][O:23][C:21]2=[CH:22][C:17]=1[CH2:16][N:13]1[CH2:14][CH2:15][C@@H:11]([NH:10][C:8](=[O:9])[CH2:7][NH:6][C:4](=[O:5])[C:3]2[CH:29]=[C:30]([C:33]([F:35])([F:34])[F:36])[CH:31]=[CH:32][C:2]=2[NH2:1])[CH2:12]1

Participants

4

Reactant 1

HCID 69214710HCID 69214710, compound

Product 1

HCID 508915HCID 508915, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (R)-3-[{N-(2-amino-5-trifluoromethylbenzoyl)glycyl}amino]-1-(4,5-methylenedioxy-2-nitrobenzyl)pyrrolidine (30.5 mg), 10% Pd-activated carbone (6 mg), and methanol (3 mL) was stirred under a hydrogen atmosphere at room temperature for 10 h. The Pd catalyst was filtered off through Celite, and the filtrate was concentrated. Solid phase extraction (Bond Elut™ SI, 20% methanol/AcOEt) afforded (R)-1-(2-amino-4,5-methylenedioxybenzyl)-3-[{N-(2-amino-5-trifluoromethylbenzoyl)glycyl}amino]pyrrolidine (Compound No. 2127) (21.9 mg, 76%): The purity was determined by RPLC/MS (95%); ESI/MS m/e 480.1 (M++H, C22H24F3N5N4).

Workup

  1. filtrationThe Pd catalyst was filtered off through Celite
  2. concentrationthe filtrate was concentrated
  3. extractionSolid phase extraction (Bond Elut™ SI, 20% methanol/AcOEt)

Sources & evidence

ORD record
ord-16b9a76d662c4923802d823529101771
Source dataset
uspto-grants-2002_03
Patent number
US06362177B1

Reaction notes

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