Water → HCID 11490053, compound

HRID 13786Notes

Reaction equation

HRID 13786 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[NH:9][C:10]1[CH:15]=[C:14]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[CH:13]=[CH:12][N:11]=1.C(N(C(C)C)CC)(C)C.Cl.Cl.[CH2:33]([N:35]1[CH2:40][CH2:39][N:38]([CH2:41][C:42]2[CH:50]=[CH:49][C:45]([C:46](Cl)=[O:47])=[CH:44][C:43]=2[C:51]([F:54])([F:53])[F:52])[CH2:37][CH2:36]1)[CH3:34].O>C(#N)C.CN(C)C1C=CN=CC=1>[CH2:33]([N:35]1[CH2:36][CH2:37][N:38]([CH2:41][C:42]2[CH:50]=[CH:49][C:45]([C:46]([NH:6][C:5]3[CH:7]=[CH:8][C:2]([CH3:1])=[C:3]([NH:9][C:10]4[CH:15]=[C:14]([C:16]5[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=5)[CH:13]=[CH:12][N:11]=4)[CH:4]=3)=[O:47])=[CH:44][C:43]=2[C:51]([F:54])([F:52])[F:53])[CH2:39][CH2:40]1)[CH3:34]

Participants

7

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 231458504-(4-Ethylpiperazin-1-ylmethyl)-3-trifluoromethylbenzoyl chloride dihydrochlorideHCID 231458974-Methyl-3-[4-(3-pyridyl)pyridin-2-ylamino]aniline

Product 1

HCID 11490053HCID 11490053, compoundYield 22.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

200 mg of 4-methyl-3-[4-(3-pyridyl)pyridin-2-ylamino]aniline (Reference Example 23) was suspended in 4 ml of acetonitrile, and 78.8 mg of 4-(dimethylamino)pyridine and 484 μl of N,N-diisopropyl-N-ethylamine were added in turn. Under ice-cooling with stirring, 383 mg of 4-(4-ethylpiperazin-1-ylmethyl)-3-trifluoromethylbenzoyl chloride dihydrochloride (Reference Example 5) was added, followed by stirring at room temperature for 2 hours. To the reaction solution was added water and the mixture was subjected to extraction with ethyl acetate three times. The organic layers were washed with saturated saline and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 93 mg of the objective compound as pale yellow crystals.

Workup

  1. temperatureUnder ice-cooling
  2. stirringby stirring at room temperature for 2 hours
  3. extractionthe mixture was subjected to extraction with ethyl acetate three times
  4. washThe organic layers were washed with saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e224a7812f7c404bb5fb7c88ceb61e49
Source dataset
uspto-grants-2010_06
Patent number
US07728131B2

Reaction notes

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