Water → HCID 70795650, compound

HRID 570453Notes

Reaction equation

HRID 570453 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]([NH:18][CH2:19][C:20]([O:22]C)=O)=[O:17])=[C:4]2[CH:3]=[CH:2]1.[CH2:24]([NH2:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C[Al](C)C.O>O1CCCC1>[CH2:24]([NH:31][C:20]([CH2:19][NH:18][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:17])=[O:22])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7504BenzylamineHCID 16682925TrimethylaluminumHCID 66957783HCID 66957783, compound

Product 1

HCID 70795650HCID 70795650, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl ({[3-(1H-pyrrolo[2,3-b]pyridin-4-ylamino)thiophen-2-yl]carbonyl}amino)acetate (50 mg, 0.15 mmol) in tetrahydrofuran (2 mL) was added a pre-mixed solution of benzylamine (25 uL, 0.23 mmol) and trimethylaluminum (2.0 M toluene, 91 uL, 0.18 mmol). The solution was stirred at room temperature for 10 minutes then water was added resulting in precipitation. The precipitate was collected by filtration and dried under vacuum to afford 3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid (benzylcarbamoyl-methyl)-amide (55 mg, 90%) (ESI) 406 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.54 (1H, br. s.) 10.31 (1H, s) 8.46 (1H, t, J=6.08 Hz) 8.39 (1H, t, J=5.69 Hz) 8.03 (1H, d, J=5.37 Hz) 7.81 (1H, d, J=5.42 Hz) 7.51 (1H, d, J=5.42 Hz) 7.33 (1H, dd, J=3.20, 2.71 Hz) 7.28 (4H, d, J=0.05 Hz) 7.16-7.25 (1H, m) 6.85 (1H, d, J=5.47 Hz) 6.44 (1H, dd, J=3.47, 1.90 Hz) 4.30 (2H, d, J=5.95 Hz) 3.89 (2H, d, J=5.71 Hz)

Workup

  1. customresulting in precipitation
  2. filtrationThe precipitate was collected by filtration
  3. customdried under vacuum

Sources & evidence

ORD record
ord-cc479389148544a0b15d4aba736c6c98
Source dataset
uspto-grants-2015_05
Patent number
US09023847B2

Reaction notes

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