Acetyl chloride → HCID 86723880, compound

HRID 576775Notes

Reaction equation

HRID 576775 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[C:13](=[O:14])[C:12]([C:15]2[N:19]([C:20]3[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=3)[N:18]=[CH:17][CH:16]=2)=[C:11]([CH3:28])[N:10]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[CH:30]=2)[C:9]1=[O:39].C(N(CC)CC)C.[C:47](Cl)(=[O:49])[CH3:48].C(=O)([O-])O.[Na+]>ClCCl>[C:24]([C:23]1[CH:22]=[CH:21][C:20]([N:19]2[C:15]([C:12]3[C:13](=[O:14])[N:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][NH:2][C:47](=[O:49])[CH3:48])[C:9](=[O:39])[N:10]([C:29]4[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:36])([F:38])[F:37])[CH:30]=4)[C:11]=3[CH3:28])=[CH:16][CH:17]=[N:18]2)=[CH:27][CH:26]=1)#[N:25]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 86723881HCID 86723881, compound

Product 1

HCID 86723880HCID 86723880, compoundYield 59.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[5-[3-(5-aminopentyl)-6-methyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl]-1H-pyrazol-1-yl]benzonitrile hydrochloride (prepared in Example 85) (6.4 mg) and triethylamine (10 μl) in dichloromethane (1.0 ml) was added acetyl chloride (0.7 mg) in ice-cooling and the resulting mixture was stirred for five minutes and stirred at room temperature for thirty minutes. To the reaction mixture was added aqueous saturated sodium hydrogen carbonate solution (10 ml) and the resulting mixture was extracted with chloroform (10 ml×2). The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform/methanol) to afford N-[5-[5-[1-(4-cyanophenyl)-1H-pyrazol-5-yl]-4-methyl-2,6-dioxo-3-(3-trifluoromethylphenyl)-2,3-dihydropyrimidin-1(6H)-yl]pentyl]acetamide (3.0 mg).

Workup

  1. temperaturecooling
  2. stirringstirred at room temperature for thirty minutes
  3. extractionthe resulting mixture was extracted with chloroform (10 ml×2)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: chloroform/methanol)

Sources & evidence

ORD record
ord-11b760128ff1400f9670c9ae15f69432
Source dataset
uspto-grants-2015_05
Patent number
US09040516B2

Reaction notes

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