Diisopropylethylamine → HCID 136395934, compound

HRID 1489038Notes

Reaction equation

HRID 1489038 reaction equation
Cl[C:2]1[N:11]2[C:12](=[O:21])[N:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:14]=[C:10]2[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1.C(N(C(C)C)CC)(C)C.[BH4-].[Na+]>[Pd].O>[C:15]1([N:13]2[C:12](=[O:21])[N:11]3[CH2:2][NH:3][C:4]4[CH2:5][CH2:6][CH2:7][CH2:8][C:9]=4[C:10]3=[N:14]2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 4311764Sodium borohydrideHCID 154288415-Chloro-2-phenyl-7,8,9,10-tetrahydro-1,2,4-triazolo[4,3-c]quinazolin-3-one

Product 1

HCID 136395934HCID 136395934, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of 5-chloro-2-phenyl-7,8,9,10-tetrahydro-1,2,4-triazolo[4,3-c]quinazolin-3-one (150 mg, 0.5 mmol), diisopropylethylamine (130 ml, 0.74 mmol) and 10% Pd-C (30 mg) was hydrogenated under H2 balloon for 1 hour. The reaction was filtered through Celite. NaBH4 (30 mg, 0.79 mmol) was added to the filtrate and the mixture was heated to reflux temperature. The reaction was poured into water and extracted with CH2Cl2 (3×50 ml). The combined organic layers were dried over Na2 SO4 and evaporated under reduced pressure. The residue was triturated with ethanol and filtered to afford 2-phenyl-5,6,7,8,9,10-hexahydro-1,2,4-triazolo[4,3-c]-quinazolin-3-one (Compound 31), m.p. 158°-159° C.

Workup

  1. customfor 1 hour
  2. filtrationThe reaction was filtered through Celite
  3. temperaturethe mixture was heated
  4. temperatureto reflux temperature
  5. extractionextracted with CH2Cl2 (3×50 ml)
  6. customThe combined organic layers were dried over Na2 SO4
  7. customevaporated under reduced pressure
  8. customThe residue was triturated with ethanol
  9. filtrationfiltered

Sources & evidence

ORD record
ord-1557ad3d4d7c485585f4a8b1bfd78d40
Source dataset
uspto-grants-1997_10
Patent number
US05677309

Reaction notes

Loading…