Hydrochloric Acid → HCID 53821205, compound

HRID 488413Notes

Reaction equation

[C:1]1([C@H:7]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:23][CH2:24][CH2:25][O:26]C4CCCCO4)=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.C(=O)(O)[O-].[Na+]>CO>[C:1]1([C@H:7]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:23][CH2:24][CH2:25][OH:26])=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of 7.70 g 4-[(R)-(1-phenyl-ethyl)amino]-7-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-6-nitro-quinazoline in 120 ml of methanol are added 2 ml of concentrated hydrochloric acid. The reaction mixture is stirred for 1.5 hours at 50° C. After cooling, the mixture is neutralized with solid sodium bicarbonate and concentrated in vacuo. The solid residue is dissolved in ethyl acetate, washed with concentrated aqueous sodium bicarbonate solution, dried over magnesium sulfate, and concentrated. The residue is triturated with 30 ml of diethyl ether, filtered off with suction, and dried. Yield: 4,34 g (88% of theory), Melting point: 187-192° C. Mass spectrum (ESI*): m/z=355 [M+H]*

Workup

temperatureAfter cooling
concentrationconcentrated in vacuo
dissolutionThe solid residue is dissolved in ethyl acetate
washwashed with concentrated aqueous sodium bicarbonate solution
dry with materialdried over magnesium sulfate
concentrationconcentrated
customThe residue is triturated with 30 ml of diethyl ether
filtrationfiltered off with suction
customdried

Sources & evidence

ORD record: ord-c8b0ca9ce4cb45acb686f94e82d94d03
Source dataset: uspto-grants-2005_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06972288B1

Reaction notes

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