Cesium carbonate → 6-(2-Methyl-2h-[1,2,4]triazol-3-ylmethoxy)-1-phenyl-1h-pyrazolo[3,4-b]pyridin-4-ylamine

HRID 1263494Notes

Reaction equation

[NH2:1][C:2]1[C:3]2[CH:11]=[N:10][N:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:4]=2[NH:5][C:6](=[O:8])[CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl.Cl[CH2:26][C:27]1[N:28]([CH3:32])[N:29]=[CH:30][N:31]=1>CN(C=O)C>[CH3:32][N:28]1[C:27]([CH2:26][O:8][C:6]2[N:5]=[C:4]3[N:9]([C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:10]=[CH:11][C:3]3=[C:2]([NH2:1])[CH:7]=2)=[N:31][CH:30]=[N:29]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-amino-1,7-dihydro-1-phenylpyrazolo[3,4-b]pyridin-6-one (0.30 g, 1.33 mmol) in DMF (8 ml) under nitrogen was added cesium carbonate (0.95 g, 2.92 mmol) followed by 3-chloromethyl-2-methyl-2H-[1,2,4]triazole hydrochloride (0.27 g, 1.61 mmol). The resulting suspension was heated at 60° C. for 17 h. The mixture was partitioned between saturated aqueous ammonium chloride solution and ethyl acetate. The layers were separated and the aqueous phase extracted a second time with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo to give the title compound as a white solid (0.41 g, 96%), m.p. 164-166° C. δH (400 MHz; CDCl3) 3.91 (3H, s), 4.70 (2H, br s), 5.58 (2H, s), 5.89 (1H, s), 7.28-7.31 (1H, m), 7.48-7.52 (2H, m), 7.88 (1H, s), 7.98 (1H, s), 8.15-8.18 (2H, m); m/z (ES+) 322 (M+H+).

Workup

customThe mixture was partitioned between saturated aqueous ammonium chloride solution and ethyl acetate
customThe layers were separated
extractionthe aqueous phase extracted a second time with ethyl acetate
washThe combined organic extracts were washed with brine
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-50e5acb5a2594b1994026d17649beeb5
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06541484B2

Reaction notes

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