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

HRID 570491Notes

Reaction equation

HRID 570491 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][C:9]([NH:10][C:11]3[CH:15]=[CH:14][S:13][C:12]=3[C:16]([OH:18])=O)=[C:4]2[CH:3]=[CH:2]1.[N:19]([CH2:22][C@H:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[NH2:24])=[N+:20]=[N-:21].CCN(C(C)C)C(C)C.O>CN(C=O)C>[N:19]([CH2:22][C@@H:23]([NH:24][C:16]([C:12]1[S:13][CH:14]=[CH:15][C:11]=1[NH:10][C:9]1[CH:8]=[CH:7][N:6]=[C:5]2[NH:1][CH:2]=[CH:3][C:4]=12)=[O:18])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)=[N+:20]=[N-:21]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 10953837HCID 10953837, compoundHCID 669574403-(1H-pyrrolo[2,3-b]pyridin-4-ylamino)thiophene-2-carboxylic acid

Product 1

HCID 866731553-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid ((S)-2-azido-1-phenyl-ethyl)-amideYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(1H-pyrrolo[2,3-b]pyridin-4-ylamino)thiophene-2-carboxylic acid (130.00 mg; 0.50 mmol; 1.00 eq.), (1S)-2-azido-1-phenylethanamine (129.67 mg; 0.55 mmol; 1.10 eq.), n,n-diisopropylethylamine (0.33 ml; 2.01 mmol; 4.00 eq.) in DMF (2.00 ml), O-(7-azabenzotriazol-1-yl)-n,n,n′,n′-tetramethyluronium hexafluoro-phosphate (209.70 mg; 0.55 mmol; 1.10 eq.) was added. The resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into water. The solid was too tiny to be filtered. The aqueous mixture was extracted with ethyl acetate to afford the title compound in 79% yield. LCMS: m/e 404 (M+H). 1H NMR (DMSO-d6): ppm 11.56 (1H, br, s.), 10.25 (1H, s.), 8.72 (1H, d, J=8.44 Hz), 8.02 (1H, d, J=5.48 Hz), 7.85 (1H, d, J=5.52 Hz), 7.50 (1H, d, J=5.48 Hz), 7.42-7.44 (1H, m), 7.26-7.35 (4H, m), 6.81 (1H, d, J=5.16 Hz), 6.40 (1H, dd, J=3.28, 1.84 Hz), 5.27-5.32 (1H, m), 3.79 (1H, dd, J=12.84, 9.52 Hz), 3.60 (1H, dd, J=12.48, 4.76 Hz).

Workup

  1. filtrationto be filtered
  2. extractionThe aqueous mixture was extracted with ethyl acetate

Sources & evidence

ORD record
ord-6ff4e374c7fa42678f4f6862287161e7
Source dataset
uspto-grants-2015_05
Patent number
US09023847B2

Reaction notes

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