Triethylamine → HCID 42601891, compound

HRID 404772Notes

Reaction equation

HRID 404772 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]3[CH:17]=[C:18]([NH2:22])[CH:19]=[CH:20][CH:21]=3)[CH:10]=2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[C:30](Cl)(=[O:33])[CH:31]=[CH2:32]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]3[CH:17]=[C:18]([NH:22][C:30](=[O:33])[CH:31]=[CH2:32])[CH:19]=[CH:20][CH:21]=3)[CH:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 57708355HCID 57708355, compound

Product 1

HCID 42601891HCID 42601891, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-[6-(3-bromophenylamino)-pyrimidin-4-ylamino]phenylamine (250 mg, 0.7 mmol) and triethylamine (180 mg, 1.75 mmol) in 5 mL of THF was stirred at RT. Acryloyl chloride (80 mg, 0.9 mmol) was added into the reaction mixture and it was stirred at RT for 1 h. The solvent was removed by vacuum evaporation and the crude product was purified by flash chromatography on silica gel with EtOAc/DCM solvent system to afford 115 mg (40% yield) of the title compound as a light colored solid. MS (m/z): MH+=410, 412. 1H NMR (DMSO): 10.15 (s, 1H), 9.36 (s, 1H), 9.28 (s, 1H), 8.34 (s, 1H), 8.02 (s, 1H), 8.00 (s, 1H), 7.51-7.11 (m, 5H), 6.47 (dd, 1H, J=10.1 Hz, J2=17.0 Hz), 6.27 (dd, 1H, J=1.9 Hz, J2=17.0 Hz), 6.20 (s, 1H), 5.76 (dd, 1H, J=10.1 Hz, J2=1.9 Hz) ppm.

Workup

  1. customThe solvent was removed by vacuum evaporation
  2. customthe crude product was purified by flash chromatography on silica gel with EtOAc/DCM solvent system

Sources & evidence

ORD record
ord-d3bca7b523de47499edd9d11c754aff2
Source dataset
uspto-grants-2014_06
Patent number
US08748606B2

Reaction notes

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