benzyl {(5S)-5-{[(5-methoxy-2-methyl-1H-indol-3-yl)acetyl]amino}-5-[5-(2-naphthyl)-1H-imidazol-2-yl]pentyl}carbamate → N-{(1S)-5-amino-1-[5-(2-naphthyl)-1H-imidazol-2-yl]pentyl}-2-(5-methoxy-2-methyl-1H-indol-3-yl)acetamide

HRID 659713Notes

Reaction equation

HRID 659713 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:12])=[C:6]2[CH2:13][C:14]([NH:16][C@H:17]([C:33]1[NH:34][C:35]([C:38]2[CH:47]=[CH:46][C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[CH:39]=2)=[CH:36][N:37]=1)[CH2:18][CH2:19][CH2:20][CH2:21][NH:22]C(=O)OCC1C=CC=CC=1)=[O:15]>CO.[Pd]>[NH2:22][CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]([NH:16][C:14](=[O:15])[CH2:13][C:6]1[C:5]2[C:9](=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=2)[NH:8][C:7]=1[CH3:12])[C:33]1[NH:34][C:35]([C:38]2[CH:47]=[CH:46][C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[CH:39]=2)=[CH:36][N:37]=1

Participants

4

Reactant 1

HCID 86631539benzyl {(5S)-5-{[(5-methoxy-2-methyl-1H-indol-3-yl)acetyl]amino}-5-[5-(2-naphthyl)-1H-imidazol-2-yl]pentyl}carbamate

Product 1

HCID 16061501N-{(1S)-5-amino-1-[5-(2-naphthyl)-1H-imidazol-2-yl]pentyl}-2-(5-methoxy-2-methyl-1H-indol-3-yl)acetamideYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A stirred solution (0.2 M) of the product from step 3 in MeOH was added to 10% Pd on carbon (17% w/w) and the heterogeneous mixture was stirred under H2 (g) at RT for the weekend. The reaction mixture was filtered through a pad of celite and washed with MeOH. Evaporation of the solvent yielded (94%) the title compound as a solid.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. washwashed with MeOH
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-3b0fb1ab73c94be088a88a114703149c
Source dataset
uspto-grants-2011_12
Patent number
US08080573B2

Reaction notes

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