Ammonium Chloride → N4-(3-Chloro-4-fluorophenyl)-7-(((3S)-tetrahydro-3-furanyl)oxy)-4,6-quinazolinediamine

HRID 563868Notes

Reaction equation

HRID 563868 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][C@H:24]4[CH2:28][CH2:27][O:26][CH2:25]4)=[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].[Cl-].[NH4+].[H][H]>CN(C=O)C.[Ni]>[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][C@H:24]4[CH2:28][CH2:27][O:26][CH2:25]4)=[C:17]([NH2:20])[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 54376755N-(3-Chloro-4-fluorophenyl)-6-nitro-7-[[(3S)-tetrahydro-3-furanyl]oxy]-4-quinazolinamineHCID 178418361HCID 178418361, compound

Product 1

HCID 15606392N4-(3-Chloro-4-fluorophenyl)-7-(((3S)-tetrahydro-3-furanyl)oxy)-4,6-quinazolinediamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

100 g of 4-[(3-chloro-4-fluorophenyl)amino]-6-nitro-7-((S)-tetrahydrofuran-3-yloxy)-quinazoline are hydrogenated in 400 ml DMF in the presence of 33.1 g Raney nickel and 18.7 g ammonium chloride at 40° C., until the calculated amount of hydrogen has been taken up. The catalyst is filtered off and the filtrate is added dropwise to 1.2 l water. The suspension is stirred for 2.5 h at 0° C., suction filtered and washed with 500 ml of water. The residue is dried overnight at 55° C. under reduced pressure.

Workup

  1. filtrationThe catalyst is filtered off
  2. additionthe filtrate is added dropwise to 1.2 l water
  3. filtrationsuction filtered
  4. washwashed with 500 ml of water
  5. customThe residue is dried overnight at 55° C. under reduced pressure

Sources & evidence

ORD record
ord-68ac33eccdd5441aaaeb400ab1082d58
Source dataset
uspto-grants-2011_11
Patent number
US08067593B2

Reaction notes

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