1-Piperazinecarboxylic acid, ethyl ester → 2-(4-Carbethoxypiperazin-1-yl)-4-amino-6,7-dimethoxyquinazoline

HRID 461332Notes

Reaction equation

HRID 461332 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](Cl)[N:3]=1.[CH3:17][CH2:18][O:19][C:20]([N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)=[O:21]>>[C:20]([N:22]1[CH2:27][CH2:26][N:25]([C:4]2[N:3]=[C:2]([NH2:1])[C:11]3[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=2)[CH2:24][CH2:23]1)([O:19][CH2:18][CH3:17])=[O:21]

Participants

3

Reactant 2

HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 902352-Chloro-6,7-dimethoxy-4-quinazolinamine

Product 1

HCID 133706732-(4-Carbethoxypiperazin-1-yl)-4-amino-6,7-dimethoxyquinazoline

Conditions

Temperature
100 °C

Procedure

In a reaction vessel equipped with stirrer, thermometer and drying tube was charged 60 ml. of isoamyl alcohol, 10 g. (0.042 mole) of 4-amino-2-chloro-6,7-dimethoxyquinazoline (prepared as described in U.S. Pat. No. 3,511,836) and 7.3 g. (0.047 mole) ethyl-N-piperazinocarboxylate (Aldrich Chemical Co.). The mixture was heated at 100° C. for 3 hours and allowed to stand overnight at room temperature. The mixture was diluted with 120 ml. of isoamyl alcohol and filtered to obtain 14.3 g. (94%) of the hydrochloride salt of the title compound, which melted sharply at 295° C.

Workup

  1. customIn a reaction vessel equipped with stirrer
  2. customthermometer and drying tube
  3. additionwas charged 60 ml
  4. additionThe mixture was diluted with 120 ml
  5. filtrationof isoamyl alcohol and filtered
  6. customto obtain 14.3 g

Sources & evidence

ORD record
ord-7b4e09c206f44fffa65c05624613a57d
Source dataset
uspto-grants-1977_12
Patent number
US04062844

Reaction notes

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