Dimethyl Sulfoxide → HCID 56598543, compound

HRID 476007Notes

Reaction equation

HRID 476007 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:14]([NH:16][CH2:17][C:18]2[C:19](=[O:26])[NH:20][C:21]([CH3:25])=[CH:22][C:23]=2[CH3:24])=[O:15])[C:5]2[CH:10]=[N:9][N:8]([CH:11]([CH3:13])[CH3:12])[C:6]=2[N:7]=1.CC1(C)C(C)(C)OB([C:35]2[CH:44]=[CH:43][C:38]3[NH:39][C:40](=[O:42])[NH:41][C:37]=3[CH:36]=2)O1.[CH3:46]S(C)=O>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:24][C:23]1[CH:22]=[C:21]([CH3:25])[NH:20][C:19](=[O:26])[C:18]=1[CH2:17][NH:16][C:14]([C:4]1[C:5]2[C:10]([CH3:46])=[N:9][N:8]([CH:11]([CH3:13])[CH3:12])[C:6]=2[N:7]=[C:2]([C:35]2[CH:44]=[CH:43][C:38]3[NH:39][C:40](=[O:42])[NH:41][C:37]=3[CH:36]=2)[CH:3]=1)=[O:15]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 438110655-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-2(3H)-oneHCID 565974256-Chloro-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

Product 1

HCID 56598543HCID 56598543, compound

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

The title compound was prepared in the same manner as described in example 74 using 6-chloro-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (70 mg, 0.187 mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydro-2H-benzimidazol-2-one (61.0 mg, 0.235 mmol), DMSO (1.5 mL) sodium carbonate (0.281 mL, 0.562 mmol), and bis(triphenylphosphine)palladium(II) chloride (10.13 mg, 0.014 mmol). The final product was collected as 19 mg (21%). LCMS E-S (M+H)=486.3 1H NMR (400 MHz, DMSO-d6) δ ppm 1.50 (d, J=6.8 Hz, 6H), 2.12 (s, 3H), 2.24 (s, 3H), 2.43 (s, 3H), 4.39 (d, J=4.6 Hz, 2H), 5.15-5.35 (m, 1H), 5.89 (s, 1H), 7.05 (d, J=8.1 Hz, 1H), 7.61 (s, 1H), 7.77-7.93 (m, 2H), 8.70-8.85 (m, 1H), 10.79 (br. s., 1H), 10.87 (br. s., 1H), 11.54 (br. s., 1H).

Workup

  1. customThe final product was collected as 19 mg (21%)

Sources & evidence

ORD record
ord-4cc3225fc8bb4315bc7e97addd950973
Source dataset
uspto-grants-2014_01
Patent number
US08637509B2

Reaction notes

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