Hydrochloric Acid → HCID 5330192, compound

HRID 1791571Notes

Reaction equation

HRID 1791571 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[CH2:24]1[O:33][C:32]2[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][C:26]=2[O:25]1.Cl>C(O)(C)C>[O:33]1[C:32]2[CH:31]=[CH:30][C:28]([NH:29][C:2]3[C:11]4[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]5[CH2:23][CH2:22][O:21][CH2:20][CH2:19]5)=[C:9]([O:12][CH3:13])[CH:10]=4)[N:5]=[CH:4][N:3]=3)=[CH:27][C:26]=2[O:25][CH2:24]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 843101,3-Benzodioxol-5-amineHCID 118239414-Chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazoline

Product 1

HCID 5330192HCID 5330192, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

A solution of 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinazoline (74 mg, 0.23 mmol), (prepared as described for the starting material in Example 1), and 3,4-(methylenedioxy)aniline (53 mg, 0.24 mmol) in a solution of isopropanol (3.5 ml) containing 5.5M hydrogen chloride in isopropanol (42 μl) was heated for 3 hours. After cooling to ambient temperature, the reaction mixture was cooled to 0° C. and maintained at this temperature overnight. The precipitate was collected by filtration, washed with ethyl acetate and dried under vacuum to give 4-(1,3-benzodioxol-5-ylamino)-6-methoxy-7-(3-morpholinopropoxy)quinazoline (82 mg, 76%).

Workup

  1. temperaturewas heated for 3 hours
  2. temperaturethe reaction mixture was cooled to 0° C.
  3. temperaturemaintained at this temperature overnight
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with ethyl acetate
  6. customdried under vacuum

Sources & evidence

ORD record
ord-5ead54da921b4c8c9f7bda41c38444cd
Source dataset
uspto-grants-2006_07
Patent number
US07074800B1

Reaction notes

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