Triethylamine → HCID 15107889, compound

HRID 1085776Notes

Reaction equation

HRID 1085776 reaction equation
[NH2:1][C:2]1[N:6]2[N:7]=[C:8]([N:15]3[CH2:20][CH2:19][CH2:18][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.C(N(CC)CC)C.[C:28](Cl)(=[O:31])[CH2:29][CH3:30]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[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:28](=[O:31])[CH2:29][CH3:30])[N:6]3[N:7]=2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 15107888HCID 15107888, compound

Product 1

HCID 15107889HCID 15107889, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

An 8.17 gm (0.030 mole) quantity of the compound of Example 9 was added to 3.54 gm (0.035 mole) of triethylamine, 300 mg of 4-dimethylaminopyridine, 3.24 gm (0.035 mole) of propionyl chloride and 50 ml of methylene chloride. This mixture was refluxed for 61/2 hours. The solvent was evaporated. The residue was patitioned between CH2Cl2 and water. The organic layer was washed with water, dried, and evaporated, resulting in a gummy residue. This residue was triturated with ether and hexane, producing a white solid. The solid was filtered and washed with ethane, then treated with benzene and hexane producing crystalline N-(7,8,9,10-tetrahydro-6-(1-piperidinyl)-1,2,4-triazolo [3,4-a]phthalazin-3yl)propanamide; mp 173-174° C. (benzene-hexane).

Workup

  1. temperatureThis mixture was refluxed for 61/2 hours
  2. customThe solvent was evaporated
  3. washThe organic layer was washed with water
  4. customdried
  5. customevaporated
  6. customresulting in a gummy residue
  7. customThis residue was triturated with ether and hexane
  8. customproducing a white solid
  9. filtrationThe solid was filtered
  10. washwashed with ethane
  11. additiontreated with benzene and hexane producing crystalline N-(7,8,9,10-tetrahydro-6-(1-piperidinyl)-1,2,4-triazolo [3,4-a]phthalazin-3yl)propanamide

Sources & evidence

ORD record
ord-05994ef4a3454088b65f385cb96c01a8
Source dataset
uspto-grants-1991_04
Patent number
US05011835

Reaction notes

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