Benzaldehyde → HCID 66852007, compound

HRID 1172265Notes

Reaction equation

HRID 1172265 reaction equation
Cl.[NH2:2][C:3]1[N:8]=[C:7]([S:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[N:12]=2)[N:6]=[C:5]([C:24]2[CH:29]=[CH:28][C:27]([NH:30][C:31](=[O:33])[CH3:32])=[CH:26][CH:25]=2)[C:4]=1[C:34]#[N:35].[CH:36](=O)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C(N(CC)CC)C.C([BH3-])#N.[Na+]>CN(C=O)C.CO>[NH2:2][C:3]1[N:8]=[C:7]([S:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][N:18]3[CH2:19][CH2:20][N:21]([CH2:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[CH2:22][CH2:23]3)[N:12]=2)[N:6]=[C:5]([C:24]2[CH:29]=[CH:28][C:27]([NH:30][C:31](=[O:33])[CH3:32])=[CH:26][CH:25]=2)[C:4]=1[C:34]#[N:35]

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 66852409HCID 66852409, compound

Product 1

HCID 66852007HCID 66852007, compoundYield 40.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

The compound of Example 18 (146 mg), benzaldehyde (28 mg) and triethylamine (75 mg) were dissolved in a mixture of 1 mL of DMF and 2 mL of methanol, the resulting mixture was stirred at room temperature overnight. To the reaction mixture under ice temperature, 30 mg of sodium cyanoborohydride was added, and the mixture was stirred at the same temperature for 1 hour. The reaction solution was evaporated to dryness under reduced pressure, thereto ice-water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and then concentrated to dryness under reduced pressure. The residue was purified by chromatography on silica gel (methylene chloride-methanol-triethylamine=600:20:1) to give 60 mg of N-(4-{6-amino-2-[6-(4-benzylpiperazin-1-ylmethyl)pyridin-2-ylmethylsulfanyl]-5-cyanopyrimidin-4-yl}phenyl)acetamide as a white powder.

Workup

  1. stirringthe mixture was stirred at the same temperature for 1 hour
  2. customThe reaction solution was evaporated to dryness under reduced pressure
  3. additionice-water was added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated to dryness under reduced pressure
  8. customThe residue was purified by chromatography on silica gel (methylene chloride-methanol-triethylamine=600:20:1)

Sources & evidence

ORD record
ord-840883c4d2fc49b7b675b1106ab51a67
Source dataset
uspto-grants-2010_11
Patent number
US07834002B2

Reaction notes

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