HCID 117871264, compound → HCID 118354449, compound

HRID 525298Notes

Reaction equation

HRID 525298 reaction equation
[C:1]([O:5][C:6](=[O:33])[N:7]([C@H:9]([C:11](=[O:32])[NH:12][C@H:13]([C:17]([N:19]1[C:23]2=[N:24][CH:25]=[CH:26][CH:27]=[C:22]2[CH2:21][C@H:20]1[CH2:28][N:29]=[N+]=[N-])=[O:18])[CH:14]([CH3:16])[CH3:15])[CH3:10])[CH3:8])([CH3:4])([CH3:3])[CH3:2]>[Pd].CO>[C:1]([O:5][C:6](=[O:33])[N:7]([C@H:9]([C:11](=[O:32])[NH:12][C@H:13]([C:17]([N:19]1[C:23]2=[N:24][CH:25]=[CH:26][CH:27]=[C:22]2[CH2:21][C@H:20]1[CH2:28][NH2:29])=[O:18])[CH:14]([CH3:16])[CH3:15])[CH3:10])[CH3:8])([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 1

HCID 117871264HCID 117871264, compound

Product 1

HCID 118354449HCID 118354449, compoundYield 90.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of {(S)-1-[(S)-1-((S)-2-azidomethyl-2,3-dihydro-pyrrolo[2,3-b]pyridine-1-carbonyl)-2-methyl-propylcarbamoyl]-ethyl}-methyl-carbamic acid tert-butyl ester (550 mg) and 10% palladium on carbon in methanol (4 mL) was stirred under a hydrogen atmosphere (balloon) for 2 h. The reaction mixture was filtered through a Celite pad and the filtrate was evaporated to dryness to give {(S)-1-[(S)-1-((S)-2-aminomethyl-2,3-dihydro-pyrrolo[2,3-b]pyridine-1-carbonyl)-2-methyl-propylcarbamoyl]-ethyl}-methyl-carbamic acid tert-butyl ester (470 mg), m/z=434 (M+H).

Workup

  1. filtrationThe reaction mixture was filtered through a Celite pad
  2. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-a22323bf9e184bfcbe3eb9b7da6d812e
Source dataset
uspto-grants-2016_05
Patent number
US09340573B2

Reaction notes

Loading…