Acetyl chloride → HCID 15107894, compound

HRID 1085778Notes

Reaction equation

HRID 1085778 reaction equation
[NH2:1][C:2]1[N:6]2[N:7]=[C:8]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[C:9]3[CH2:10][CH2:11][CH2:12][CH2:13][C:14]=3[C:5]2=[N:4][N:3]=1.CN(C1C=CC=CN=1)C.C(N(CC)CC)C.[C:37](Cl)(=[O:39])[CH3:38]>ClC(Cl)C>[N:15]1([C:8]2[C:9]3[CH2:10][CH2:11][CH2:12][CH2:13][C:14]=3[C:5]3=[N:4][N:3]=[C:2]([NH:1][C:37](=[O:39])[CH3:38])[N:6]3[N:7]=2)[CH2:16][CH2:17][O:18][CH2:19][CH2:20]1

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 15107893HCID 15107893, compound

Product 1

HCID 15107894HCID 15107894, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A 5.80 gm (0.0211 mole) quantity of the compound of Example 15 was dissolved in 100 ml of dichloroethane, and 380 mg (0.003 mole) of dimethylaminopyridine and 3.1 gm (0.03 mole) of triethylamine were added, followed by 2.38 gm (0.030 mole) of acetyl chloride. This mixture was refluxed overnight and evaporated. The resulting mixture was partioned between dilute aqueous NaHCO3 and CH2Cl2. The organic layer was dried and evaporated. The residue was triturated with ether and the resulting solid was collected to give 4.40 g of N-(7,8,9,10-tetrahydro-6-(4-morpholinyl)-1, 2,4-triazolo[3,4-a]phthalazin-3yl)acetamide; mp 147-149° C. (toluene-hexane).

Workup

  1. temperatureThis mixture was refluxed overnight
  2. customevaporated
  3. customThe organic layer was dried
  4. customevaporated
  5. customThe residue was triturated with ether
  6. customthe resulting solid was collected

Sources & evidence

ORD record
ord-fc8adebecde64290a731e608231549fa
Source dataset
uspto-grants-1991_04
Patent number
US05011835

Reaction notes

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