Dimethylformamide → HCID 21897585, compound

HRID 1864159Notes

Reaction equation

[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15]3=[N:16][CH:17]=[N:18][C:19]([NH:20][CH:21]4[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]4)=[C:14]3[CH:13]=[N:12]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].BrC1C=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[CH:30]N=1.C(=O)([O-])[O-].[K+].[K+].[CH3:44][N:45]([CH:47]=O)C>>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15]3=[N:16][CH:17]=[N:18][C:19]([NH:20][CH:21]4[CH2:26][CH2:25][N:24]([C:44]5[CH:30]=[CH:31][C:32]([C:34]([F:37])([F:36])[F:35])=[CH:47][N:45]=5)[CH2:23][CH2:22]4)=[C:14]3[CH:13]=[N:12]2)=[CH:7][CH:6]=1)(=[O:3])=[O:4]

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 11430Potassium Carbonate

HCID 27815432-Bromo-4-(trifluoromethyl)pyridine

HCID 21897507HCID 21897507, compound

Product 1

HCID 21897585HCID 21897585, compoundYield 32%

Conditions

Temperature: 165 °C

Procedure

A mixture of [1-(4-methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]-piperidin-4-yl-amine (100 mg, 0.24 mmol), 2-bromo-4-trifluoromethylpyridine (166 mg, 0.73 mmol), and potassium carbonate (102 mg, 0.73 mmol) in DMF (1.0 mL) was heated under microwave irradiation for 20 minutes at 165° C. The crude mixture was purified by HPLC to provide compound A128 as a white solid (41 mg, 32%). Exact mass calculated for C23H22F3N7O2S 517.15, found 518.2 (MH+).

Workup

customThe crude mixture was purified by HPLC

Sources & evidence

ORD record: ord-b985d79eada04b1a997d3021b5118fe7
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625906B2

Reaction notes

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