Acetyl chloride → HCID 70795514, compound

HRID 570428Notes

Reaction equation

HRID 570428 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][NH:11][C:12]([C:14]1[S:15][CH:16]=[CH:17][C:18]=1[NH:19][C:20]1[CH:25]=[CH:24][N:23]=[C:22]2[NH:26][CH:27]=[CH:28][C:21]=12)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[C:38](Cl)(=[O:40])[CH3:39]>O1CCCC1>[C:38]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:9][CH2:10][NH:11][C:12]([C:14]1[S:15][CH:16]=[CH:17][C:18]=1[NH:19][C:20]1[CH:25]=[CH:24][N:23]=[C:22]2[NH:26][CH:27]=[CH:28][C:21]=12)=[O:13])(=[O:40])[CH3:39]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 50923854HCID 50923854, compound

Product 1

HCID 70795514HCID 70795514, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid (2-benzylamino-ethyl)-amide (95 mg, 0.24 mmol), diisopropylethylamine (84 uL, 0.49 mmol) and acetyl chloride (25 uL, 0.37 mmol) in tetrahydrofuran (2.0 mL) was stirred at room temperature for 18 h. The solution was concentrated in vacuo then 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-(acetyl-benzyl-amino)-ethyl]-amide (25 mg, 24%). LCMS (ESI) 434 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.56 (1H, br. s.) 10.16-10.43 (1H, m) 8.15 (0H, t, J=5.00 Hz) 8.02 (1H, t, J=2.71 Hz) 7.72-7.86 (1H, m) 7.44-7.54 (1H, m) 7.13-7.39 (6H, m) 6.83 (1H, dd, J=12.23, 5.49 Hz) 6.36-6.50 (1H, m) 4.49-4.61 (2H, m) 3.34-3.50 (4H, m) 1.91-2.19 (3H, m)

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customthen purified by ISCO Companion (silica, 10% methanol, methylene chloride, 1% ammonium hydroxide)

Sources & evidence

ORD record
ord-d40259f4836d477aa35fe486bc9d69fd
Source dataset
uspto-grants-2015_05
Patent number
US09023847B2

Reaction notes

Loading…