Sodium Carbonate → HCID 178425144, compound

HRID 476006Notes

Reaction equation

HRID 476006 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.[NH:27]1[C:31]2[CH:32]=[CH:33][C:34](B(O)O)=[CH:35][C:30]=2[N:29]=[N:28]1.C(=O)([O-])[O-].[Na+].[Na+]>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.CS(C)=O>[NH:27]1[C:31]2[CH:32]=[CH:33][C:34]([C:2]3[CH:3]=[C:4]([C:14]([NH:16][CH2:17][C:18]4[C:19](=[O:26])[NH:20][C:21]([CH3:25])=[CH:22][C:23]=4[CH3:24])=[O:15])[C:5]4[CH:10]=[N:9][N:8]([CH:11]([CH3:13])[CH3:12])[C:6]=4[N:7]=3)=[CH:35][C:30]=2[N:29]=[N:28]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 565974256-Chloro-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamideHCID 178514825HCID 178514825, compound

Product 1

HCID 178425144HCID 178425144, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 679Dimethyl SulfoxideSolvent

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), 1H-1,2,3-benzotriazol-5-ylboronic acid (39.7 mg, 0.243 mmol), DMSO (2 mL), sodium carbonate (0.281 mL, 0.562 mmol) and bis(triphenylphosphine)palladium(II) chloride (10.51 mg, 0.015 mmol). The final product was collected as 22 mg (26%). LCMS E-S (M+H)=457.1 1H NMR (400 MHz, DMSO-d6) δ ppm 1.57 (d, 6 J=6.4 Hz, H), 2.14 (s, 3H), 2.24 (s, 3H), 4.43 (d, J=4.3 Hz, 2H), 5.31-5.46 (m, 1H), 5.91 (s, 1H), 8.07 (br. s., 1H), 8.34 (s, 1H), 8.41 (m, 2H), 8.85 (br. s., 1H), 9.02 (br. s., 1H), 11.59 (br. s., 1H).

Workup

  1. customThe final product was collected as 22 mg (26%)

Sources & evidence

ORD record
ord-aeb6d1246f724137bccff1bb951aedd7
Source dataset
uspto-grants-2014_01
Patent number
US08637509B2

Reaction notes

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