3,4-Difluoroaniline → HCID 67298096, compound

HRID 1520364Notes

Reaction equation

HRID 1520364 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]2[CH:17]=[CH:16][N:15]=[N:14][CH:13]=2)[N:3]=1.[F:18][C:19]1[CH:20]=[C:21]([NH2:26])[CH:22]=[CH:23][C:24]=1[F:25]>CC(O)C>[F:18][C:19]1[CH:20]=[C:21]([NH:26][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[C:4]([C:12]3[CH:17]=[CH:16][N:15]=[N:14][CH:13]=3)[N:3]=2)[CH:22]=[CH:23][C:24]=1[F:25]

Participants

4

Reactant 2

HCID 774693,4-DifluoroanilineHCID 86677080HCID 86677080, compound

Product 1

HCID 67298096HCID 67298096, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
85 °C

Procedure

(This method is representative of method G1, G2, and G3. These three methods can be implemented in a similar way except for substitution of the appropriate solvent and temperature) The mixture of 4-chloro-2-(pyridazin-4-yl)quinazoline (10 mg, 0.041 mmol, 1 eq.) and 3,4-difluorobenzenamine (11 mg, 0.082 mmol, 2 eq.) was suspended in i-PrOH. The mixture was heated at 85° C. overnight. After cooling, the resulting precipitate was filtered and purified on HPLC (Condition C). 7.3 mg of N-(3,4-difluorophenyl)-2-(pyridazin-4-yl)quinazolin-4-amine was obtained (yield 53%). LCMS m/z=336.0 (M+1) (Method B) (retention time=1.731 min). 1H-NMR (400 MHz, DMSO-d6): δ 10.23 (s, 1H), 10.00 (dd, J=2.2, 1.3 Hz, 1H), 9.44 (dd, J=5.4, 1.2 Hz, 1H), 8.59 (d, J=8.1 Hz, 1H), 8.39 (dd, J=5.4, 2.4 Hz, 1H), 8.05-8.13 (m, 1H), 7.99 (s, 1H), 7.97 (d, J=3.6 Hz, 1H), 7.72-7.79 (m, 2H), 7.51-7.61 (m, 1H).

Workup

  1. temperatureAfter cooling
  2. filtrationthe resulting precipitate was filtered
  3. custompurified on HPLC (Condition C)

Sources & evidence

ORD record
ord-b5e37edba91045c9b94201d464180d86
Source dataset
uspto-grants-2015_07
Patent number
US09073890B2

Reaction notes

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