Cesium carbonate → 6-{[4-(Aminocarbonyl)phenyl]amino}-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

HRID 476014Notes

Reaction equation

HRID 476014 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:15]([NH:17][CH2:18][C:19]2[C:20](=[O:27])[NH:21][C:22]([CH3:26])=[CH:23][C:24]=2[CH3:25])=[O:16])[C:5]2[C:10](C)=[N:9][N:8]([CH:12]([CH3:14])[CH3:13])[C:6]=2[N:7]=1.[NH2:28][C:29]1[CH:37]=[CH:36][C:32]([C:33]([NH2:35])=[O:34])=[CH:31][CH:30]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C)C(=O)C>[NH2:35][C:33]([C:32]1[CH:36]=[CH:37][C:29]([NH:28][C:2]2[CH:3]=[C:4]([C:15]([NH:17][CH2:18][C:19]3[C:20](=[O:27])[NH:21][C:22]([CH3:26])=[CH:23][C:24]=3[CH3:25])=[O:16])[C:5]3[CH:10]=[N:9][N:8]([CH:12]([CH3:13])[CH3:14])[C:6]=3[N:7]=2)=[CH:30][CH:31]=1)=[O:34]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 760794-AminobenzamideHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 565974266-Chloro-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-3-methyl-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

Product 1

HCID 565971616-{[4-(Aminocarbonyl)phenyl]amino}-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 31374DimethylacetamideSolvent

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]-3-methyl-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (70 mg, 0.180 mmol), 4-aminobenzamide (29.5 mg, 0.217 mmol), cesium carbonate (88 mg, 0.271 mmol), N,N-dimethylacetamide (DMA) (1.5 mL), palladium(II) acetate (2.431 mg, 10.83 μmol) and Xantphos (10.44 mg, 0.018 mmol) wherein the reaction temperature was 150° C. and reaction time was 1 h. The final product was collected as 12 mg (14%). LCMS E-S (M+H)=488.2 1H NMR (400 MHz, DMSO-d6) δ ppm 1.48 (d, J=6.4 Hz, 6H), 2.13 (s, 3H), 2.23 (s, 3H), 2.32 (s, 3H), 4.35 (d, J=4.8 Hz, 2H), 4.99 (quin, J=6.8 Hz, 1H), 5.89 (s, 1H), 6.65 (s, 1H), 7.15 (br. s., 1H), 7.75-7.82 (m, 1H), 7.84-7.96 (m, 4H), 8.56 (t, J=4.9 Hz, 1H), 9.77 (s, 1H).

Workup

  1. customwas 150° C.
  2. customreaction time
  3. customThe final product was collected as 12 mg (14%)

Sources & evidence

ORD record
ord-1f9abc44fcd348d3a3723ca08f8c1292
Source dataset
uspto-grants-2014_01
Patent number
US08637509B2

Reaction notes

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