Triethylamine → HCID 57593246, compound

HRID 1785335Notes

Reaction equation

HRID 1785335 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:14]=[C:13]([NH:15][CH2:16][C:17]#[CH:18])[C:12]([Br:19])=[CH:11][N:10]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:27][N:28]1[CH:32]=[C:31]([S:33](Cl)(=[O:35])=[O:34])[N:30]=[CH:29]1>C(#N)C>[Br:19][C:12]1[C:13]([NH:15][CH2:16][C:17]#[CH:18])=[N:14][C:9]([NH:8][C:5]2[CH:6]=[CH:7][C:2]([NH:1][S:33]([C:31]3[N:30]=[CH:29][N:28]([CH3:27])[CH:32]=3)(=[O:35])=[O:34])=[CH:3][CH:4]=2)=[N:10][CH:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27368871-methyl-1H-imidazole-4-sulfonyl chlorideHCID 57593369N2-(4-Amino-phenyl)-5-bromo-N4-prop-2-ynyl-pyrimidine-2,4-diamine

Product 1

HCID 57593246HCID 57593246, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N2-(4-Amino-phenyl)-5-bromo-N4-prop-2-ynyl-pyrimidine-2,4-diamine (100 mg, 0.3 mmole prepared in analogy to procedure 21) was dissolved in acetonitrile (10 ml) and triethylamine (1 ml) and 1-Methyl-1H-imidazole-4-sulfonyl chloride (120 mg, 0.66 mmole) was added at room temperature. The reaction mixture was stirred under reflux for 5 hours, the solvent was removed under reduced pressure and the crude product was purified by column chromatography on silica gel (ethyl acetate: hexanes 1:1). Yield 41 mg of 1-Methyl-1H-imidazole-4-sulfonic acid [4-(5-b bromo-4-prop-2-ynylamino-pyrimidin-2-ylamino)-phenyl]-amide. ESI-MS: 463.

Workup

  1. temperatureunder reflux for 5 hours
  2. customthe solvent was removed under reduced pressure
  3. customthe crude product was purified by column chromatography on silica gel (ethyl acetate: hexanes 1:1)

Sources & evidence

ORD record
ord-59347390abdc4841a5e6227ec895b081
Source dataset
uspto-grants-2009_03
Patent number
US07504410B2

Reaction notes

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