2-(difluoro(4-fluorophenyl)methyl)-7-fluoro-N-(5-methyl-1H-pyrazol-3-yl)quinazolin-4-amine → 4-Chloro-2-(difluoro(4-fluorophenyl)methyl)-7-methylquinazoline

HRID 625764Notes

Reaction equation

HRID 625764 reaction equation
F[C:2](F)(C1C=CC(F)=CC=1)C1N=C(NC2C=C(C)NN=2)C2C(=CC(F)=CC=2)N=1.[Cl:29][C:30]1[C:39]2[C:34](=[CH:35][C:36](F)=[CH:37][CH:38]=2)[N:33]=[C:32]([C:41]([F:50])([F:49])[C:42]2[CH:47]=[CH:46][C:45]([F:48])=[CH:44][CH:43]=2)[N:31]=1>>[Cl:29][C:30]1[C:39]2[C:34](=[CH:35][C:36]([CH3:2])=[CH:37][CH:38]=2)[N:33]=[C:32]([C:41]([F:49])([F:50])[C:42]2[CH:43]=[CH:44][C:45]([F:48])=[CH:46][CH:47]=2)[N:31]=1

Participants

3

Reactant 2

HCID 468926232-(difluoro(4-fluorophenyl)methyl)-7-fluoro-N-(5-methyl-1H-pyrazol-3-yl)quinazolin-4-amineHCID 729429294-Chloro-2-(difluoro(4-fluorophenyl)methyl)-7-fluoroquinazoline

Product 1

HCID 729429274-Chloro-2-(difluoro(4-fluorophenyl)methyl)-7-methylquinazolineYield 13%

Procedure

2-(Difluoro(4-fluorophenyl)methyl)-7-methyl-N-(5-methyl-1H-pyrazol-3-yl)quinazolin-4-amine was obtained according to the procedure described in Example 20 for preparation of 2-(difluoro(4-fluorophenyl)methyl)-7-fluoro-N-(5-methyl-1H-pyrazol-3-yl)quinazolin-4-amine, substituting 4-chloro-2-(difluoro(4-fluorophenyl)methyl)-7-fluoroquinazoline in Example 20 with 4-chloro-2-(difluoro(4-fluorophenyl)methyl)-7-methylquinazoline (13% yield). 1H NMR (300 MHz, DMSO-d6) δ 2.26 (s, 3H), 2.50 (s, 3H), 6.30 (s, 1H), 7.34 (t, 2H), 7.47 (m, 1H), 7.71-7.66 (m, 3H), 8.56 (d, 1H), 10.59 (s, 1H), 12.20 (bs, 1H); LC-MS (ESI) m/z 384 (M+H)+.

Sources & evidence

ORD record
ord-5f4142ca8229453b9a76e4105d178302
Source dataset
uspto-grants-2016_04
Patent number
US09308207B2

Reaction notes

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