Ammonium formate → HCID 51347781, compound

HRID 1968705Notes

Reaction equation

HRID 1968705 reaction equation
Cl[C:2]1[CH:3]=[N:4][CH:5]=[C:6](Cl)[C:7]=1[N:8]1[C:16](=[O:17])[C:15]2[C:10]([C:11]3[S:32][CH:31]=[CH:30][C:12]=3[N:13]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([N:25]4[CH:29]=[CH:28][CH:27]=[N:26]4)=[CH:21][CH:20]=3)[CH:14]=2)=[N:9]1.C([O-])=O.[NH4+]>CO>[N:25]1([C:22]2[CH:23]=[CH:24][C:19]([CH2:18][N:13]3[CH:14]=[C:15]4[C:16](=[O:17])[N:8]([C:7]5[CH:6]=[CH:5][N:4]=[CH:3][CH:2]=5)[N:9]=[C:10]4[C:11]4[S:32][CH:31]=[CH:30][C:12]3=4)=[CH:20][CH:21]=2)[CH:29]=[CH:28][CH:27]=[N:26]1

Participants

4

Reactant 2

HCID 2723923Ammonium formateHCID 51347632HCID 51347632, compound

Product 1

HCID 51347781HCID 51347781, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(3,5-Dichloropyridin-4-yl)-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[3,4-d]thieno[3,2-b]pyridin-3-one (Example 15, 15 mg, 0.030 mmol), ammonium formate (2.9 mg, 0,046 mmol, 1.5 equiv) and 1,1′-bis(diphenylphosphino)ferroenedichloro palladium (II) dichloromethane complex (4.4 mg, 6.1 lima 0.2 equiv) were combined in methanol (5 mL) and placed into a preheated oil bath at 70° C. for 14 hours. The mixture was cooled to ambient temperature and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 85:15; chloroform:methanol), providing the titled compound: 1H-NMR (400 MHz, d6-DMSO) δ 9.28 (1H, s), 8.76 (2H, br d, J=5.5 Hz), 8.57 (2H, br d, J=5.5 Hz), 8.48 (1H, d, J=2.5 Hz), 8.16 (1H, d, J=5.6 Hz), 7.84 (2H, d, J=8.6 Hz), 7.73 (1H, d, J=1.5 Hz), 7.68 (1H, d, J=5.6 Hz), 7.53 (2H, d, J=8.6 Hz), 6.53 (1H, dd, J=2.4, 1.8 Hz), 5.77 (2H, s) ppm; high resolution mass spectrometry (ES+) m/z 425.1184 [(M+H)+; calculated for C23H17N6OS: 425.1179].

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by silica gel gradient chromatography (100:0 to 85:15; chloroform:methanol)

Sources & evidence

ORD record
ord-f49018a4806b4d168ff833662b36d1d2
Source dataset
uspto-grants-2013_04
Patent number
US08426438B2

Reaction notes

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