Dimethylformamide → HCID 86271307, compound

HRID 2177589Notes

Reaction equation

HRID 2177589 reaction equation
N1C=[CH:5][CH:4]=[N:3][C:2]=1[N:7]1[C:15]2[CH2:14][CH2:13][NH:12][CH2:11][C:10]=2[N:9]=[N:8]1.[F:16][C:17]1[C:25]([C:26]([F:29])([F:28])[F:27])=[CH:24][CH:23]=[CH:22][C:18]=1[C:19](O)=[O:20].ClC1C(C(F)(F)F)=CC=CC=1C(O)=O.C(Cl)Cl.[CH3:47][N:48](C=O)C>>[F:16][C:17]1[C:25]([C:26]([F:29])([F:28])[F:27])=[CH:24][CH:23]=[CH:22][C:18]=1[C:19]([N:12]1[CH2:13][CH2:14][C:15]2[N:7]([C:2]3[CH:47]=[N:48][CH:5]=[CH:4][N:3]=3)[N:8]=[N:9][C:10]=2[CH2:11]1)=[O:20]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 5180022-Fluoro-3-(trifluoromethyl)benzoic acidHCID 27366772-Chloro-3-(trifluoromethyl)benzoic acidHCID 90409586HCID 90409586, compound

Product 1

HCID 86271307HCID 86271307, compound

Procedure

The title compound was prepared in a manner analogous to Example 65 substituting the product of Example 69, Step A for 1-pyrimidin-2-yl-4,5,6,7-tetrahydro-1H-[1,2,3]triazolo[4,5-c]pyridine, 2-fluoro-3-(trifluoromethyl)benzoic acid for 2-chloro-3-(trifluoromethyl)-benzoic acid and DCM for DMF. MS (ESI): mass calcd. for C17H12F4N6O, 392.1. m/z found, 393.1 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 9.52 (dd, J=15.7, 1.4 Hz, 1H), 8.66 (dd, J=7.3, 2.5 Hz, 1H), 8.52-8.45 (m, 1H), 7.80-7.71 (m, 1H), 7.72-7.58 (m, 1H), 7.38 (dt, J=14.9, 7.7 Hz, 1H), 5.09 (s, 1H), 4.67 (s, 1H), 3.67 (s, 1H), 3.43 (t, J=5.8 Hz, 1H), 3.33 (s, 1H), 1.88-1.71 (s, 1H).

Sources & evidence

ORD record
ord-dcbc589416d74ab7ba0c31a36f38a0fa
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

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