2-Chloro-4,6-dimethylpyrimidine → HCID 67086946, compound

HRID 2175038Notes

Reaction equation

HRID 2175038 reaction equation
[C@@H:1]12[N:8]([C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)=[O:10])[CH2:7][C@@H:6]1[CH2:5][CH2:4][NH:3][CH2:2]2.C1(C2C=CC=CC=2)C=CC=CC=1C(N1C2C(CCNC2)C1)=O.Cl[C:45]1[N:50]=[C:49]([CH3:51])[CH:48]=[C:47]([CH3:52])[N:46]=1.ClC1C=NC2C(=CC=CC=2)N=1>>[CH3:52][C:47]1[CH:48]=[C:49]([CH3:51])[N:50]=[C:45]([N:3]2[CH2:4][CH2:5][C@@H:6]3[C@@H:1]([N:8]([C:9]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[C:17]4[S:18][CH:19]=[CH:20][CH:21]=4)=[O:10])[CH2:7]3)[CH2:2]2)[N:46]=1

Participants

5

Reactant 4

HCID 205502-Chloro-4,6-dimethylpyrimidineHCID 2389382-ChloroquinoxalineHCID 67086667HCID 67086667, compoundHCID 89593632HCID 89593632, compound

Product 1

HCID 67086946HCID 67086946, compound

Procedure

The title compound was prepared in a manner analogous to Example 1, substituting (1R,6S) (3,8-diaza-bicyclo[4.2.0]oct-8-yl)-(2-thiophen-2-yl-phenyl)-methanone (Intermediate 7) for biphenyl-2-yl-(3,8-diaza-bicyclo[4.2.0]oct-8-yl)-methanone and 2-chloro-4,6-dimethyl-pyrimidine for 2-chloro quinoxaline. MS (ESI) mass calcd. for C23H24N4OS, 404.53; m/z found 405.2 [M+H]+. 1H NMR (CDCl3) 7.54-7.27 (m, 4H), 7.25-7.12 (m, 2H), 7.07 (dd, J=5.1, 3.6, 0.7H), 6.81-6.75 (m, 0.3H), 6.29 (d, J=17.6, 1H), 4.78-4.54 (m, 0.75H), 4.10-3.55 (m, 4.5H), 3.52-3.33 (m, 0.75H), 3.01-2.90 (m, 0.6H), 2.73-2.56 (m, 1H), 2.30 (d, J=23.8, 6H), 2.10-1.50 (m, 2.4H).

Sources & evidence

ORD record
ord-66d9a5ea745545b5ae07c83ef236a61d
Source dataset
uspto-grants-2015_06
Patent number
US09062044B2

Reaction notes

Loading…