Benzoic Acid → HCID 66852565, compound

HRID 1668542Notes

Reaction equation

HRID 1668542 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].[C:36](O)(=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C.C(N(CC)CC)C>[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]([C:36](=[O:43])[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 243Benzoic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 66852409HCID 66852409, compound

Product 1

HCID 66852565HCID 66852565, compoundYield 90.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

The compound of Example 18 (292 mg), benzoic acid (61 mg) and triethylamine (0.2 mL) was dissolved in 3 mL of DMF, to the above solution, 80 mg of HOBt was added under stirring at ice temperature. After stirring the mixture at the same temperature for 15 minutes, thereto 115 mg of WSC was added, and the mixture was stirred at room temperature overnight. The reaction solution was evaporated to dryness under reduced pressure, and ice-water was added to the resulting residue, 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=300:10:1) to give 261 mg of N-(4-{6-amino-2-[6-(4-benzoylpiperazin-1-ylmethyl)pyridin-2-ylmethylsulfanyl]-5-cyanopyrimidin-4-yl}phenyl)acetamide as a white powder.

Workup

  1. additionwas added
  2. stirringAfter stirring the mixture at the same temperature for 15 minutes
  3. stirringthe mixture was stirred at room temperature overnight
  4. customThe reaction solution was evaporated to dryness under reduced pressure, and ice-water
  5. additionwas added to the resulting residue
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated to dryness under reduced pressure
  10. customThe residue was purified by chromatography on silica gel (methylene chloride-methanol-triethylamine=300:10:1)

Sources & evidence

ORD record
ord-59fcb6febcdd431b8797e932a1e0d2fc
Source dataset
uspto-grants-2011_08
Patent number
US07989446B2

Reaction notes

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