Water → N4-(4,5-dichloro-2-fluoro-phenyl)-7-[2-ethoxy-ethoxy]-quinazoline-4,6-diamine

HRID 1255978Notes

Reaction equation

HRID 1255978 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28]O)=[C:17]([N+:20]([O-])=O)[CH:18]=3)[N:13]=[CH:12][N:11]=2)=[C:4]([F:30])[CH:3]=1.O.O.NN>CCO.[Ni]>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:23][CH2:24][CH2:25][O:26][CH2:27][CH3:28])=[C:17]([NH2:20])[CH:18]=3)[N:13]=[CH:12][N:11]=2)=[C:4]([F:30])[CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 692669552-{2-[4-(4,5-Dichloro-2-fluoro-phenylamino)-6-nitro-quinazoline-7-yloxy]-ethoxy}-ethanol

Product 1

HCID 69320196N4-(4,5-dichloro-2-fluoro-phenyl)-7-[2-ethoxy-ethoxy]-quinazoline-4,6-diamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Compound 29a is dissolved in a 9:1 mixture of EtOH:H2O at 85° C., a solution of hydrazine monohydrate in a Ra—Ni solution is added and the reaction mixture is stirred for 1 hour. The obtained solution is cooled and thereafter filtered over Celite®. The filtrate is evaporated under reduced pressure to afford Compound 41a.

Workup

  1. temperatureThe obtained solution is cooled
  2. filtrationfiltered over Celite®
  3. customThe filtrate is evaporated under reduced pressure

Sources & evidence

ORD record
ord-c3f9aeb72e344eec902f390ec3b3b362
Source dataset
uspto-grants-2013_06
Patent number
US08461166B2

Reaction notes

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