Thionyl Chloride → HCID 178526400, compound

HRID 500690Notes

Reaction equation

HRID 500690 reaction equation
FC1C=C2C(C(=O)NC=N2)=CC=1.[F:13][C:14]1[CH:23]=[C:22]2[C:17]([C:18](=O)[NH:19][CH:20]=[N:21]2)=[CH:16][C:15]=1[N+:25]([O-:27])=[O:26].S(Cl)([Cl:30])=O>>[Cl:30][C:18]1[NH:19][CH2:20][N:21]=[C:22]2[C:17]=1[CH:16]=[C:15]([N+:25]([O-:27])=[O:26])[C:14]([F:13])=[CH:23]2

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 1353984967-Fluoroquinazolin-4(3H)-oneHCID 1353985077-Fluoro-6-nitroquinazolin-4(1H)-one

Product 1

HCID 178526400HCID 178526400, compound

Procedure

4-Chloro-7-fluoro-6-nitroquinazoline (7) can be prepared by methods similar to those described in J.Med. Chem. 1996, 39, 918-928. Generally, 2-amino-4-fluoro-benzoic acid (1) can be reacted with formamidine (2) and acetic acid (3) in the presence of 2-methoxyethanol to provide 7-Fluoro-3H-quinazolin-4-one (4). The 7-fluoro-3H-quinazolin-4-one (4) can be nitrated to 7-fluoro-6-nitro-3H-quinazolin-4-one (5), which can be treated with thionyl chloride to yield 4-chloro-6-nitro-7-fluoro-3H-quinazoline (6). The 4-chloro-quinazoline compound (6) can be combined with a desirably substituted aniline, represented above by 4-fluoro-3-chloro-aniline, in the presence of a tertiary amine and isopropanol to provide the 4-anilino-6-nitro-7-fluoro-quinazoline (7).

Sources & evidence

ORD record
ord-ea1afb10c4a14617a7607909663c0107
Source dataset
uspto-grants-2010_08
Patent number
US07772243B2

Reaction notes

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