Cesium carbonate → HCID 56598682, compound

HRID 1522405Notes

Reaction equation

HRID 1522405 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.[NH2:27][C:28]1[CH:37]=[CH:36][C:31]2[NH:32][C:33](=[O:35])[NH:34][C:30]=2[CH:29]=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>[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[CH:10]=[N:9][N:8]([CH:11]([CH3:13])[CH3:12])[C:6]=2[N:7]=[C:2]([NH:27][C:28]2[CH:37]=[CH:36][C:31]3[NH:32][C:33](=[O:35])[NH:34][C:30]=3[CH:29]=2)[CH:3]=1)=[O:15]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 667655-Amino-2-hydroxybenzimidazoleHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 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 56598682HCID 56598682, compound

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]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (70 mg, 0.187 mmol), 5-amino-1,3-dihydro-2H-benzimidazol-2-one (33.5 mg, 0.225 mmol), cesium carbonate (92 mg, 0.281 mmol), N,N-dimethylacetamide (DMA) (2 mL), palladium(II) acetate (2.52 mg, 0.011 mmol) and Xantphos (10.83 mg, 0.019 mmol) wherein the reaction temperature was 150° C. and reaction time was 8 h. The final product was collected as 25 mg (27%). LCMS E-S (M+H)=487.2 1H NMR (400 MHz, DMSO-d6) δ ppm 1.50-1.61 (m, 6 H), 2.13 (s, 3 H), 2.23 (s, 3 H), 4.38 (d, J=5.0 Hz, 2 H), 5.20 (quin, J=6.6 Hz, 1 H), 5.90 (s, 1 H), 6.79-6.91 (m, 2 H), 8.04 (d, J=8.3 Hz, 1 H), 8.26-8.33 (m, 2 H), 8.84 (t, J=5.0 Hz, 1 H), 11.50 (s, 1 H).

Workup

  1. customwas 150° C.
  2. customreaction time
  3. customThe final product was collected as 25 mg (27%)

Sources & evidence

ORD record
ord-58cf8a673ec746dd9e641403fff25da9
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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