HCID 50924916, compound → HCID 50924917, compound

HRID 570455Notes

Reaction equation

HRID 570455 reaction equation
[N:1]([CH2:4][CH: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-].[H][H]>CO.[Pd]>[NH2:1][CH2:4][CH: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

5

Reactant 2

HCID 50924916HCID 50924916, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 50924917HCID 50924917, compoundYield 78.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid (2-azido-1-phenyl-ethyl)-amide (120 mg, 0.27 mmol), 5% Pd/C (cat) in methanol (5 mL) was subjected to an atmosphere of hydrogen (balloon). After completion the solution was filtered and concentrated in vacuo. The residue was purified by ISCO Companion (silica, 10% methanol, methylene chloride, 1% ammonium hydroxide) to afford 3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid (2-amino-1-phenyl-ethyl)-amide (80 mg, 75%) (ESI) 378 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.51 (1H, br. s.) 8.00 (1H, d, J=5.47 Hz) 7.82 (1H, d, J=5.42 Hz) 7.45 (1H, d, J=5.42 Hz) 7.25-7.35 (5H, m) 7.16-7.24 (1H, m) 6.75 (1H, d, J=5.47 Hz) 6.39 (1H, d, J=3.12 Hz) 4.97 (1H, dd, J=8.03, 5.34 Hz) 2.85-2.94 (1H, m) 2.77-2.85 (1H, m)

Workup

  1. filtrationAfter completion the solution was filtered
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by ISCO Companion (silica, 10% methanol, methylene chloride, 1% ammonium hydroxide)

Sources & evidence

ORD record
ord-affb0f329ff94faf9a71d65dca65c8ef
Source dataset
uspto-grants-2015_05
Patent number
US09023847B2

Reaction notes

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