N-(3-Chloro-4-fluorophenyl)-7-methoxy-6-nitroquinazolin-4-amine → N4-(3-Chloro-4-fluorophenyl)-7-methoxy-4,6-quinazolinediamine

HRID 467610Notes

Reaction equation

HRID 467610 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:23][CH3:24])=[C:17]([N+:20]([O-])=O)[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8]>[Ni].C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:23][CH3:24])=[C:17]([NH2:20])[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 1

HCID 21847811N-(3-Chloro-4-fluorophenyl)-7-methoxy-6-nitroquinazolin-4-amine

Product 1

HCID 21847826N4-(3-Chloro-4-fluorophenyl)-7-methoxy-4,6-quinazolinediamineYield 99%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

7.1 g of (3-Chloro-4-fluoro-phenyl)-(7-methoxy-6-nitro-quinazolin-4-yl)-amine was reduced using Raney nickel catalyst in THF, then filtered and evaporated to give 6.4 g N4-(3-Chloro-4-fluoro-phenyl)-7-methoxy-quinazoline-4,6-diamine (99% yield). This product was reacted with 4-Chloro-but-2-enoyl chloride as described in Scheme 1 to provide 4-Chloro-but-2-enoic acid [4-(3-chloro-4-fluoro-phenylamino)-7-methoxy-quinazolin-6-yl]-amide.

Workup

  1. filtrationfiltered
  2. customevaporated

Sources & evidence

ORD record
ord-d6f336a46b874fbfb2ede5451ddb1aec
Source dataset
uspto-grants-2014_01
Patent number
US08623883B2

Reaction notes

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