2-Chloro-6,7-dimethoxy-4-quinazolinamine → Terazosin Hydrochloride Anhydrous

HRID 1653671

Reaction equation

HRID 1653671 reaction equation
[Cl:1][C:2]1[N:11]=[C:10]([NH2:12])[C:9]2[C:4](=[CH:5][C:6]([O:15][CH3:16])=[C:7]([O:13][CH3:14])[CH:8]=2)[N:3]=1.[O:17]1[CH2:21][CH2:20][CH2:19][CH:18]1[C:22]([N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)=[O:23]>COC(O)C>[ClH:1].[O:17]1[CH2:21][CH2:20][CH2:19][CH:18]1[C:22]([N:24]1[CH2:25][CH2:26][N:27]([C:2]2[N:11]=[C:10]([NH2:12])[C:9]3[C:4](=[CH:5][C:6]([O:15][CH3:16])=[C:7]([O:13][CH3:14])[CH:8]=3)[N:3]=2)[CH2:28][CH2:29]1)=[O:23]

Participants

4

Reactant 2

HCID 902352-Chloro-6,7-dimethoxy-4-quinazolinamineHCID 27346411-(Tetrahydro-2-furoyl)piperazine

Product 1

HCID 44383Terazosin Hydrochloride Anhydrous

Reagents, catalysts & solvents 1

HCID 30156371-MethoxyethanolSolvent

Procedure

To 7.00 g 2-chloro-4-amino-6,7-dimethoxyquinazoline (Lancaster Synthesis) in 50 ml methoxyethanol was added 10.8 g, tetrahydrofuroylpiperazine, and the mixture refluxed 3 hours. The clear solution was concentrated and an aqueous solution of potassium bicarbonate was added. The resultant solid that formed was filtered and washed with water. It was then added to methanol and the resulting suspension was acidified with a solution of hydrogen chloride in isopropyl alcohol. The resulting solution was concentrated and the residue crystallized from isopropyl alcohol giving 8.12 g. of product, m.p. 278°-279° C.

Workup

  1. temperaturethe mixture refluxed 3 hours
  2. concentrationThe clear solution was concentrated
  3. additionan aqueous solution of potassium bicarbonate was added
  4. customThe resultant solid that formed
  5. filtrationwas filtered
  6. washwashed with water
  7. additionIt was then added to methanol
  8. concentrationThe resulting solution was concentrated
  9. customthe residue crystallized from isopropyl alcohol giving 8.12 g

Sources & evidence

ORD record
ord-0e41a6faa1c04f1c9c0eadce49ddc28e
Source dataset
uspto-grants-1995_04
Patent number
US05403847

Linked notes

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