Potassium Carbonate → HCID 136056017, compound

HRID 1770856Notes

Reaction equation

HRID 1770856 reaction equation
Cl[CH2:2][C:3]1[NH:4][C:5](=[O:8])[NH:6][N:7]=1.[NH2:9][S:10]([C:13]1[CH:14]=[C:15]([NH:20][C:21]2[N:26]=[C:25]([NH:27][C:28]3[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=3)[C:24]([F:35])=[CH:23][N:22]=2)[CH:16]=[CH:17][C:18]=1[F:19])(=[O:12])=[O:11].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[NH2:9][S:10]([C:13]1[CH:14]=[C:15]([NH:20][C:21]2[N:26]=[C:25]([NH:27][C:28]3[CH:33]=[CH:32][C:31]([O:34][CH2:2][C:3]4[NH:4][C:5](=[O:8])[NH:6][N:7]=4)=[CH:30][CH:29]=3)[C:24]([F:35])=[CH:23][N:22]=2)[CH:16]=[CH:17][C:18]=1[F:19])(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 25185595HCID 25185595, compoundHCID 1355466853H-1,2,4-Triazol-3-one, 5-(chloromethyl)-1,2-dihydro-2×

Product 1

HCID 136056017HCID 136056017, compoundYield 20.4%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a solution of 5-chloromethyl-2,4-dihydro-1,2,4-triazol-3-one (35 mg, 0.26 mmol) in 2-butanone, were added N2-(3-aminosulfonyl-4-fluorophenyl)-5-fluoro-N4-(4-hydroxyphenyl)-2,4-pyrimidinediamine (100 mg, 0.25 mmol) and potassium carbonate (35 mg, 0.25 mmol). The resulting mixture was microwaved at 140° C. for 5 hours, and then additional of 5-chloromethyl-2,4-dihydro-1,2,4-triazol-3-one was added as needed The reaction solvent was removed under a reduced pressure, and the residual was purified by column chromatography (silica gel, dichloromethane: methanol 8:2 v/v) to give 25 mg of N2-(3-aminosulfonyl-4-fluorophenyl)-5-fluoro-N4-[4-(2,4-dihydro-3-oxo-1,2,4-triazol-5-yl)methoxyphenyl]-2,4-pyrimidinediamine (76) as a light yellow solid. 1H NMR (D2O): δ 7.90-7.89 (d, J=3 Hz, 1H), 7.60-7.58 (d, J=6 Hz, 1H), 7.34 (bs, 2H), 7.24-7.18 (m, 2H), 7.05-7.02 (d, J=9.0 Hz, 2H), 6.65-6.62 (d, J=9.0 Hz, 2H), 5.11 (br s, 2H); LCMS (m/z): 491.05 (MH+).

Workup

  1. customThe resulting mixture was microwaved at 140° C. for 5 hours
  2. customwas removed under a reduced pressure
  3. customthe residual was purified by column chromatography (silica gel, dichloromethane: methanol 8:2 v/v)

Sources & evidence

ORD record
ord-94d3a4927d1a40d48797b8dbc63428f9
Source dataset
uspto-grants-2016_02
Patent number
US09248190B2

Reaction notes

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