Triethylamine → HCID 15428777, compound

HRID 617180Notes

Reaction equation

HRID 617180 reaction equation
[NH2:1][C:2]1[N:11]=[C:10]([CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(N(CC)CC)C.[CH2:25]1[O:33][C:32]2[CH:31]=[CH:30][C:29]([CH2:34][C:35](Cl)=[O:36])=[CH:28][C:27]=2[O:26]1.C(=O)([O-])O.[Na+]>ClCCl>[NH2:1][C:2]1[N:11]=[C:10]([CH:12]2[CH2:17][CH2:16][N:15]([C:35](=[O:36])[CH2:34][C:29]3[CH:30]=[CH:31][C:32]4[O:33][CH2:25][O:26][C:27]=4[CH:28]=3)[CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 2756584Benzo[1,3]dioxol-5-yl-acetyl chlorideHCID 154287752-Amino-4-(4-piperidinyl)quinazoline

Product 1

HCID 15428777HCID 15428777, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 3,4-methylenedioxyphenylacetic acid (569 mg, 3.16 mmol) in chloroform (6 ml) was added thionyl chloride (1.2 ml). The mixture was refluxed for about 3 hours, and was evaporated. Toluene was added to the residue and the mixture was evaporated to remove the excess of thionyl chloride. To the residue was added dichloromethane (3 ml) to give a dichloromethane solution of 3,4-methylenedioxyphenylacetyl chloride. To an ice-cold mixture of 2-amino-4-(4-piperidinyl)quinazoline (600 mg, 2.63 mmol) and triethylamine (319 mg, 3.16 mmol) in dichloromethane (16 ml) was added dropwise the solution of 3,4-methylenedioxyphenylacetyl chloride prepared above under a nitrogen atmosphere. The mixture was stirred for about two hours and to the reaction mixture was added dichloromethane and saturated sodium hydrogencarbonate aqueous solution followed by extraction. The organic layer was washed with water, and then dried over sodium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography (dichloromethane:methanol=30:1). Crystallization from methanol gave the titled compound (617 mg).

Workup

  1. customprepared above under a nitrogen atmosphere
  2. extractionfollowed by extraction
  3. washThe organic layer was washed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (dichloromethane:methanol=30:1)
  7. customCrystallization from methanol

Sources & evidence

ORD record
ord-b7820777653c462f8a7af225103b724b
Source dataset
uspto-grants-1999_09
Patent number
US05948786

Reaction notes

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