HCID 50925351, compound → HCID 50923446, compound

HRID 570489Notes

Reaction equation

HRID 570489 reaction equation
[N:1]([CH2:4][C@@H:5]([NH:12][C:13]([C:15]1[CH:19]=[CH:18][S:17][C:16]=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][C@@H:5]([NH:12][C:13]([C:15]1[CH:19]=[CH:18][S:17][C:16]=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 50925351HCID 50925351, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 50923446HCID 50923446, compoundYield 92.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-3-carboxylic acid ((S)-2-azido-1-phenyl-ethyl)-amide (40 mg, 0.1 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 2-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-3-carboxylic acid ((S)-2-amino-1-phenyl-ethyl)-amide (35 mg) (ESI) 378 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 12.61 (1H, br. s.) 11.45 (1H, s) 9.32 (1H, d, J=8.20 Hz) 8.28 (3H, br. s.) 8.08 (1H, d, J=6.88 Hz) 7.75 (1H, d, J=5.81 Hz) 7.47 (2H, d, J=5.86 Hz) 7.33 (2H, dd, J=7.57, 1.81 Hz) 7.12-7.24 (3H, m) 6.81 (1H, dd, J=2.49, 1.22 Hz) 6.68 (1H, d, J=6.88 Hz) 5.28 (1H, dd, J=10.54, 4.73 Hz) 3.40 (1H, td, J=11.53, 5.44 Hz) 3.12 (1H, dd, J=7.39, 4.61 Hz)

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-fc23eea2973747d084c67eea60b0c5be
Source dataset
uspto-grants-2015_05
Patent number
US09023847B2

Reaction notes

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