2-Chloroquinoxaline → (1R,6S)-8-(6-Methyl-2-trifluoromethyl-pyrimidin-4-yl)-3,8-diaza-bicyclo[4.2.0]octane

HRID 1193061Notes

Reaction equation

HRID 1193061 reaction equation
C12N(C3C=NC4C(=CC=CC=4)N=3)CC1CCNC2.C(OC([N:26]1[CH2:33][CH2:32][CH:31]2[CH:28]([NH:29][CH2:30]2)[CH2:27]1)=O)(C)(C)C.Cl[C:35]1[CH:40]=[C:39]([CH3:41])[N:38]=[C:37]([C:42]([F:45])([F:44])[F:43])[N:36]=1.ClC1C=NC2C(=CC=CC=2)N=1>>[CH3:41][C:39]1[N:38]=[C:37]([C:42]([F:45])([F:43])[F:44])[N:36]=[C:35]([N:29]2[C@@H:28]3[C@@H:31]([CH2:32][CH2:33][NH:26][CH2:27]3)[CH2:30]2)[CH:40]=1

Participants

5

Reactant 4

HCID 2389382-ChloroquinoxalineHCID 250672674-Chloro-6-methyl-2-(trifluoromethyl)pyrimidineHCID 43810891Tert-butyl 3,8-diazabicyclo[4.2.0]octane-3-carboxylate2×HCID 671166512-(3,8-Diaza-bicyclo[4.2.0]oct-8-yl)-quinoxaline

Product 1

HCID 68156957(1R,6S)-8-(6-Methyl-2-trifluoromethyl-pyrimidin-4-yl)-3,8-diaza-bicyclo[4.2.0]octane

Procedure

The title compound was prepared in a manner analogous to Intermediate 2, substituting (1R,6S)-(3,8-diaza-bicyclo[4.2.0]octane-3-carboxylic acid tert-butyl ester for 3,8-diaza-bicyclo[4.2.0]octane-3-carboxylic acid tert-butyl ester and 4-chloro-2-trifluoromethyl-6-methyl-pyrimidine for 2-chloro-quinoxaline in Step A. MS (ESI) mass calcd. for C12H15F3N4, 272.27; m/z found 273.0 [M+H]+. 1H NMR (CDCl3): 6.29 (s, br, 1H), 6.13 (s, 1H), 4.52 (d, J=8.0, 1H), 4.08-3.94 (m, 1H), 3.87-3.75 (m, 1H), 3.64 (t, J=19.8, 1H), 3.39-3.26 (m, 1H), 3.11 (dd, J=14.2, 3.5, 1H), 3.00-2.77 (m, 2H), 2.38 (s, 3H), 2.22-2.07 (m, 1H), 1.92-1.79 (m, 1H).

Sources & evidence

ORD record
ord-5c458a5266eb41559d59d9c9e4f6a021
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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