2-Chloro-6,7-dimethoxy-4-quinazolinamine → HCID 131712025, compound

HRID 1389165Notes

Reaction equation

HRID 1389165 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:16])[N:3]=1.Cl.[NH:18]1[CH2:23][CH2:22][CH:21]([CH2:24][CH2:25][C:26]([OH:28])=[O:27])[CH2:20][CH2:19]1>C(O)CCC>[ClH:16].[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:18]2[CH2:23][CH2:22][CH:21]([CH2:24][CH2:25][C:26]([O:28][CH2:11][CH2:6][CH2:7][CH3:8])=[O:27])[CH2:20][CH2:19]2)[N:3]=1

Participants

4

Reactant 2

HCID 902352-Chloro-6,7-dimethoxy-4-quinazolinamineHCID 211985473-(Piperidin-4-yl)propanoic acid--hydrogen chloride (1/1)

Product 1

HCID 131712025HCID 131712025, compoundYield 114.7%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

4-Amino-2-chloro-6,7-dimethoxyquinazoline (24.9 g) and 3-(4-piperidinyl)propionic acid, hydrochloride (20 g) in n-butanol (1000 ml) were stirred under reflux for 20 hours. The hot suspension was filtered and the insoluble material discarded. The filtrate was cooled in ice/water, the precipitated solid collected and the filtrate evaporated in vacuo. The resulting solid and the precipitated solid were combined and crystallised from isopropanol to give 4-amino-2-[4-(2-{n-butoxycarbonyl}ethyl)piperidino]-6,7-dimethoxyquinazoline, hydrochloride (27.0 g) with m.p. 250°-252°.

Workup

  1. temperatureunder reflux for 20 hours
  2. filtrationThe hot suspension was filtered
  3. temperatureThe filtrate was cooled in ice/water
  4. customthe precipitated solid collected
  5. customthe filtrate evaporated in vacuo
  6. customcrystallised from isopropanol

Sources & evidence

ORD record
ord-741510022d514c349793c795e552878b
Source dataset
uspto-grants-1981_01
Patent number
US04243666

Reaction notes

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