Benzoyl chloride → HCID 50924763, compound

HRID 570450Notes

Reaction equation

HRID 570450 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[S:8][CH:9]=[CH:10][C:11]=1[NH:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]2[NH:19][CH:20]=[CH:21][C:14]=12)=[O:6].C(N(C(C)C)CC)(C)C.[C:31](Cl)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C(Cl)Cl>[C:31]([NH:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[S:8][CH:9]=[CH:10][C:11]=1[NH:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]2[NH:19][CH:20]=[CH:21][C:14]=12)=[O:6])(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 81531DiisopropylethylamineHCID 509244533-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid (2-amino-ethyl)-amide

Product 1

HCID 50924763HCID 50924763, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid (2-amino-ethyl)-amide (40 mg, 0.12 mmol) and diisopropylethylamine (0.1 mL, 0.59 mmol) in methylene chloride (1.0 mL) was added benzoyl chloride (15 uL, 0.13 mmol) and stirred at room temperature for 30 min. The crude reaction was purified by ISCO Companion (silica, (silica, 0-5% methanol, methylene chloride, 1% ammonium hydroxide) to afford 3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid (2-benzoylamino-ethyl)-amide (48 mg, 48%). LCMS (ESI) 406 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.51 (1H, br. s.) 10.36 (1H, s) 8.55 (1H, s) 8.24 (1H, br. s.) 8.00 (1H, d, J=5.27 Hz) 7.73-7.85 (3H, m) 7.43-7.52 (2H, m) 7.35-7.42 (2H, m) 7.28 (1H, d, J=3.32 Hz) 6.82 (1H, d, J=5.47 Hz) 6.40 (1H, d, J=3.51 Hz) 3.39-3.45 (4H, m)

Workup

  1. customThe crude reaction
  2. customwas purified by ISCO Companion (silica, (silica, 0-5% methanol, methylene chloride, 1% ammonium hydroxide)

Sources & evidence

ORD record
ord-0be4a87f4b3d470bbabc38909029e611
Source dataset
uspto-grants-2015_05
Patent number
US09023847B2

Reaction notes

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