3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid ((S)-2-azido-1-phenyl-ethyl)-amide → 3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid ((S)-2-amino-1-phenyl-ethyl)-amide

HRID 570492Notes

Reaction equation

HRID 570492 reaction equation
[N:1]([CH2:4][C@@H:5]([NH:12][C:13]([C:15]1[S:16][CH:17]=[CH:18][C:19]=1[NH:20][C:21]1[CH:26]=[CH:25][N:24]=[C:23]2[NH:27][CH:28]=[CH:29][C:22]=12)=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[N+]=[N-]>CO.[Pd]>[NH2:1][CH2:4][C@@H:5]([NH:12][C:13]([C:15]1[S:16][CH:17]=[CH:18][C:19]=1[NH:20][C:21]1[CH:26]=[CH:25][N:24]=[C:23]2[NH:27][CH:28]=[CH:29][C:22]=12)=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 1

HCID 866731553-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid ((S)-2-azido-1-phenyl-ethyl)-amide

Product 1

HCID 509235913-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid ((S)-2-amino-1-phenyl-ethyl)-amideYield 66%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid ((S)-2-azido-1-phenyl-ethyl)-amide (130.00 mg; 0.32 mmol; 1.00 eq.) in methanol (50.00 ml) was subjected to hydrogenation with 10% palladium on carbon via H-Cube at 1 mL/min. After completion the solution was concentrated in vacuo. The crude was purified by Yamazen (basic condition, 0.1% NH4OH in Water/ACN) to afford the title compound as white solid in 66% yield. LCMS: m/e 378 (M+H). 1H NMR (DMSO-d6): ppm 11.53 (1H, br. s.), 8.00 (1H, d, J=5.48 Hz), 7.82 (1H, d, J=5.12 Hz), 7.45 (1H, d, J=5.48 Hz), 7.26-7.33 (5H, m), 7.18-7.22 (1H, m), 6.75 (1H, d, J=5.52 Hz), 6.39 (1H, d, J=3.28 Hz), 4.96 (1H, dd, J=8.08, 5.52 Hz), 2.78-2.88 (2H, m).

Workup

  1. concentrationAfter completion the solution was concentrated in vacuo
  2. customThe crude was purified by Yamazen (basic condition, 0.1% NH4OH in Water/ACN)

Sources & evidence

ORD record
ord-47c0fc63cf1f4cfdacbfbf13cd57a4f5
Source dataset
uspto-grants-2015_05
Patent number
US09023847B2

Reaction notes

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