Triethylamine → HCID 66853865, compound

HRID 1668548Notes

Reaction equation

HRID 1668548 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2)[N:5]=[C:4]([S:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][CH2:26][C:27]([N:29]3[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]3)=[O:28])[N:20]=2)[N:3]=1.C(N(CC)CC)C.[C:43](Cl)(=[O:46])[CH2:44][CH3:45]>C(#N)C>[NH2:1][C:2]1[N:3]=[C:4]([S:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][CH2:26][C:27]([N:29]3[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]3)=[O:28])[N:20]=2)[N:5]=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:43](=[O:46])[CH2:44][CH3:45])=[CH:12][CH:11]=2)[C:7]=1[C:8]#[N:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 66853838HCID 66853838, compound

Product 1

HCID 66853865HCID 66853865, compoundYield 29.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The compound of Example 56 (150 mg) and triethylamine (0.5 mL) were dissolved in 10 mL of acetonitrile, and 0.1 g of propionyl chloride was added dropwise to the mixture and the mixture was stirred at room temperature for 30 minutes. After removing the solvent, the residue was dissolved in chloroform. Thereto water was added, the organic layer was washed with water (twice), then brine (once), and dried over magnesium sulfate. After the solvent was removed under reduced pressure, the resulting oil was purified by chromatography on silica gel (methylene chloride-methanol-aqueous ammonia=90:10:1) to give 50 mg of N-[4-(6-amino-5-cyano-2-{6-[3-(4-methylpiperazin-1-yl)-3-oxopropyl]pyridin-2-ylmethylsulfanyl}pyrimidin-4-yl)phenyl]propionamide as a light yellow powder.

Workup

  1. customAfter removing the solvent
  2. dissolutionthe residue was dissolved in chloroform
  3. additionThereto water was added
  4. washthe organic layer was washed with water (twice), then brine (once), and
  5. dry with materialdried over magnesium sulfate
  6. customAfter the solvent was removed under reduced pressure
  7. customthe resulting oil was purified by chromatography on silica gel (methylene chloride-methanol-aqueous ammonia=90:10:1)

Sources & evidence

ORD record
ord-dfac4b2577284d9087ece0223ffc03ba
Source dataset
uspto-grants-2011_08
Patent number
US07989446B2

Reaction notes

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