Dimethylamine → HCID 136395933, compound

HRID 1489034Notes

Reaction equation

HRID 1489034 reaction equation
[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:21](=[O:22])[N:12]3[CH2:13][NH:14][C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=4[C:11]3=[N:10]2)=[CH:5][CH:4]=1.[CH3:23][NH:24][CH3:25]>C1COCC1>[ClH:1].[CH3:23][N:24]([CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:21](=[O:22])[N:12]3[CH2:13][NH:14][C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=4[C:11]3=[N:10]2)=[CH:5][CH:4]=1)[CH3:25]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 136018531HCID 136018531, compound2×

Product 1

HCID 136395933HCID 136395933, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 2-[4-(chloromethyl)-phenyl]-5,6-dihydro-1,2,4-triazolo[4,3-c]-quinazolin-3-one (Compound 20) (150 mg, 0.48 mmol) and dimethylamine (1 ml, 40% in H2O) in THF was heated at 40° C. for 1.5 hours. The reaction was extracted with CH2Cl2 (3×50 ml) and the combined organic layers were dried over Na2SO4 and evaporated under reduced pressure. The residue was dissolved in ethyl acetate and saturated HCl/ethyl acetate solution was added to yield 2-[4-(N,N-dimethylaminomethyl)phenyl]-5,6-dihydro-1,2,4-triazolo-[4,3-c]quinazolin-3-one hydrochloride (Compound 21), m.p. 244°-247° C.

Workup

  1. extractionThe reaction was extracted with CH2Cl2 (3×50 ml)
  2. dry with materialthe combined organic layers were dried over Na2SO4
  3. customevaporated under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. additionsaturated HCl/ethyl acetate solution was added

Sources & evidence

ORD record
ord-9baeccf3102a46859276a00cf7c8d68e
Source dataset
uspto-grants-1997_10
Patent number
US05677309

Reaction notes

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