Triethylamine → HCID 15107895, compound

HRID 1085779Notes

Reaction equation

HRID 1085779 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.C(N(CC)CC)C.[C:28](Cl)(=[O:31])[CH2:29][CH3:30]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[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)[CH2:16][CH2:17][O:18][CH2:19][CH2:20]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 15107893HCID 15107893, compound

Product 1

HCID 15107895HCID 15107895, compoundYield 76.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5.80 gm (0.0211 mole) of the compound of Example 15 in 50 ml of CH2Cl2 was added 3.03 g (0.03 mole) of triethylamine, 384 mg (0.003 mole) of 4-dimethylaminopyridine and 2.78 g (0.03 mole) of propionyl chloride. The mixture was heated at reflux for 15 hours, cooled, and partitioned between CH2Cl2 and aqueous NaHCO3. The organic layer was dried (Na2SO4) and concentrated to give a thick oil which crystallized on trituration with toluene-hexane. The resulting white solid was collected to give 5.32 gm of N-(7,8,9,10-tetrahydro-6-(4-morpholinyl)-1,2,4-triazolo [3,4-a]phthalazin3-yl)propanamide; mp 164-166° C. (ethanol-ether). Calculated: C, 58.16; H, 6.71, N, 25.44. Found: C, 58.17; H, 6.70; N, 25.67.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 15 hours
  3. temperaturecooled
  4. custompartitioned between CH2Cl2 and aqueous NaHCO3
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. concentrationconcentrated
  7. customto give a thick oil which
  8. customcrystallized on trituration with toluene-hexane
  9. customThe resulting white solid was collected

Sources & evidence

ORD record
ord-922d7e09b4ad4556a0b290785195194b
Source dataset
uspto-grants-1991_04
Patent number
US05011835

Reaction notes

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