2-Fluoro-3-(trifluoromethyl)benzoyl chloride → (2-Fluoro-3-(trifluoromethyl)phenyl)(4-methyl-1-(pyridin-2-yl)-6,7-dihydro-1H-imidazo[4,5-c]pyridin-5(4H)-yl)methanone

HRID 2177565Notes

Reaction equation

HRID 2177565 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[CH:15]=[CH:14][N:13]=[CH:12][C:11]=3[N:10]=[CH:9]2)=[N:6][CH:7]=1.[F:17][C:18]1[C:26]([C:27]([F:30])([F:29])[F:28])=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21].Cl[C:32]1C(C(F)(F)F)=CC=CC=1C(Cl)=O>>[F:17][C:18]1[C:26]([C:27]([F:30])([F:29])[F:28])=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([N:13]1[CH2:14][CH2:15][C:16]2[N:8]([C:5]3[CH:4]=[CH:3][CH:2]=[CH:7][N:6]=3)[CH:9]=[N:10][C:11]=2[CH:12]1[CH3:32])=[O:21]

Participants

4

Reactant 3

HCID 27375592-Fluoro-3-(trifluoromethyl)benzoyl chlorideHCID 38276332-Chloro-3-(trifluoromethyl)benzoyl chlorideHCID 904095831-(5-Fluoropyridin-2-yl)-1H-imidazo[4,5-c]pyridine

Product 1

HCID 86271854(2-Fluoro-3-(trifluoromethyl)phenyl)(4-methyl-1-(pyridin-2-yl)-6,7-dihydro-1H-imidazo[4,5-c]pyridin-5(4H)-yl)methanone

Procedure

Example 19 was prepared in an analogous way as Example 11 substituting Intermediate 3 for Intermediate 1 and Intermediate 13 for Intermediate 12 in Step A. 1H NMR (500 MH, CDCl3) δ 8.53 (dd, J=12.7, 11.7 Hz, 1H), 8.03-7.99 (m, 1H), 7.92-7.80 (m, 1H), 7.70-7.60 (m, 2H), 7.40-7.27 (m, 3H), 5.78 (s, 1H), 5.10-4.56 (m, 1H), 3.75-3.31 (m, 1H), 3.31-2.76 (m, 2H), 1.83-1.38 (m, 3H). MS (ESI): mass calculated for C20H16F4N4O, 404.13. m/z found 405.2 [M+H]+.

Sources & evidence

ORD record
ord-43a9565648384aa1ac6c5de403d1aa27
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

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