Triethylamine → HCID 20437729, compound

HRID 1979927Notes

Reaction equation

HRID 1979927 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[N:3]=1.[Cl:22][C:23]1[N:24]=[N:25][C:26](OC)=[CH:27][CH:28]=1.C(N(CC)CC)C>C(O)CCCC>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([N:16]2[CH2:21][CH2:20][N:19]([C:26]3[N:25]=[N:24][C:23]([Cl:22])=[CH:28][CH:27]=3)[CH2:18][CH2:17]2)[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 744033-Chloro-6-methoxypyridazineHCID 6162672-(1-Piperazinyl)-4-amino-6,7-dimethoxyquinazoline

Product 1

HCID 20437729HCID 20437729, compound

Reagents, catalysts & solvents 1

HCID 62761-PentanolSolvent

Procedure

4-Amino-6,7-dimethoxy-2-piperazinoquinazoline (3.0 g, 10.4 mmole), 3-chloro-6-methoxy-pyridazine (3.96 g, 27.4 mmole) and triethylamine (5.0 g, 49.5 mmole) in n-pentanol (210 ml) were heated under reflux for 25 hours. The solvent was evaporated in vacuo and the residue partitioned between chloroform and saturated aqueous sodium carbonate solution. The organic layer was separated, washed with water, dried (Na2SO4) and evaporated in vacuo. The residue was chromatographed on silica gel (200 g) eluting with chloroform followed by 5% methanol in chloroform. Further purification of the major product by HPLC using a Waters 500 Prep. LC/system, eluting with 6% by volume methanol in methylene chloride at a flow rate of 0.15 liters per minute gave the desired product which was recrystallized from methanol, m.p. 269°-270° C. (0.5 g).

Workup

  1. temperatureunder reflux for 25 hours
  2. customThe solvent was evaporated in vacuo
  3. customthe residue partitioned between chloroform and saturated aqueous sodium carbonate solution
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialdried (Na2SO4)
  7. customevaporated in vacuo
  8. customThe residue was chromatographed on silica gel (200 g)
  9. washeluting with chloroform
  10. customFurther purification of the major product by HPLC
  11. washLC/system, eluting with 6% by volume methanol in methylene chloride at a flow rate of 0.15 liters per minute

Sources & evidence

ORD record
ord-b4a18c4ec4974838b7db9ec7bbe1c006
Source dataset
uspto-grants-1984_11
Patent number
US04483857

Reaction notes

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