1-(Bromomethyl)-2,3-dichlorobenzene → 7-[2-Chloro-3-(trifluoromethyl)benzyl]-3-pyridin-2-yl-6,7-dihydro[1,2,4]triazolo[4,3-a]pyrazin-8(5H)-one

HRID 576713Notes

Reaction equation

HRID 576713 reaction equation
[N:1]1[CH:6]=[CH:5]N=[CH:3][C:2]=1[C:7]1[N:11]2[CH2:12][CH2:13][NH:14][C:15](=[O:16])[C:10]2=[N:9][N:8]=1.Br[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[C:20]=1[Cl:29].Br[CH2:31]C1C=CC=C(Cl)C=1Cl>>[Cl:29][C:20]1[C:21]([C:25]([F:28])([F:27])[F:26])=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][N:14]1[CH2:13][CH2:12][N:11]2[C:7]([C:2]3[CH:3]=[CH:31][CH:5]=[CH:6][N:1]=3)=[N:8][N:9]=[C:10]2[C:15]1=[O:16]

Participants

4

Reactant 3

HCID 27346021-(Bromomethyl)-2,3-dichlorobenzeneHCID 27788481-(Bromomethyl)-2-chloro-3-(trifluoromethyl)benzeneHCID 904025243-(pyrazin-2-yl)-6,7-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-8(5H)-one

Product 1

HCID 862793467-[2-Chloro-3-(trifluoromethyl)benzyl]-3-pyridin-2-yl-6,7-dihydro[1,2,4]triazolo[4,3-a]pyrazin-8(5H)-oneYield 89%

Procedure

Example 9 was made in a manner analogous to Example 2 substituting Intermediate 2 for Intermediate 1 and 1-(bromomethyl)-2-chloro-3-(trifluoromethyl)benzene for 1-(bromomethyl)-2,3-dichlorobenzene to provide the desired compound as a white solid (66 mg, 89%). MS (ESI): mass calcd. for C18H13ClF3N5O, 407.1; m/z found, 408.1 [M+H]+. 1H NMR (600 MHz, DMSO-d6) δ 8.75 (ddd, J=4.8, 1.6, 0.9 Hz, 1H), 8.29 (dt, J=8.0, 0.9 Hz, 1H), 8.05 (dt, J=7.8, 1.7 Hz, 1H), 7.82 (dd, J=12.7, 7.8 Hz, 2H), 7.64-7.49 (m, 2H), 4.97-4.90 (m, 2H), 4.88 (s, 2H), 3.98-3.88 (m, 2H).

Sources & evidence

ORD record
ord-1e212edcaf914ecbb38fe73764f748a4
Source dataset
uspto-grants-2015_05
Patent number
US09040534B2

Reaction notes

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