Hydrochloric Acid → HCID 22732245, compound

HRID 2084008Notes

Reaction equation

HRID 2084008 reaction equation
[Cl: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]=[CH:4][N:3]=1.[C:16]([C:18]1[CH:33]=[CH:32][C:21]([C:22]([NH:24][C:25]2[CH:26]=[C:27]([CH:29]=[CH:30][CH:31]=2)[NH2:28])=[O:23])=[CH:20][CH:19]=1)#[N:17].Cl>C(O)(C)C.C(OCC)C>[ClH:1].[C:16]([C:18]1[CH:19]=[CH:20][C:21]([C:22]([NH:24][C:25]2[CH:26]=[C:27]([CH:29]=[CH:30][CH:31]=2)[NH:28][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][N:3]=2)=[O:23])=[CH:32][CH:33]=1)#[N:17]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 27693644-Chloro-6,7-dimethoxyquinazolineHCID 16785182HCID 16785182, compound

Product 1

HCID 22732245HCID 22732245, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
85 °C

Procedure

4-Chloro-6,7-dimethoxyquinazoline (225 mg) was added to 3-(4-cyanobenzamido)aniline (261 mg) in isopropanol (8 ml). A 1M solution of hydrogen chloride in diethyl ether (1.0 ml) was added and the reaction mixture stirred and heated to 85° C. for 18 hours. After cooling to room temperature the precipitated solid was isolated and washed with isohexane and diethyl ether. The title compound was obtained as a solid (399 mg); NMR: 3.99 (s, 3H), 4.01 (s, 3H), 7.37 (s, 1H), 7.45 (m, 2H), 7.65 (m, 1H), 8.02 (m, 2H), 8.12 (m, 2H), 8.20 (m, 1H), 8.31 (s, 2H), 8.80 (s, 1H), 10.71 (s, 1H), 11.44 (s, 1H); m/s: M+H+ 426.

Workup

  1. temperatureAfter cooling to room temperature the precipitated solid
  2. customwas isolated
  3. washwashed with isohexane and diethyl ether

Sources & evidence

ORD record
ord-a95910f57abc4a64accc4f856eb4548c
Source dataset
uspto-grants-2004_04
Patent number
US06716847B2

Reaction notes

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