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

HRID 1193063Notes

Reaction equation

HRID 1193063 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]([C:41]([F:44])([F:43])[F:42])[N:38]=[C:37]([N:45]([CH3:47])[CH3:46])[N:36]=1.ClC1C=NC2C(=CC=CC=2)N=1>>[C@@H:28]12[N:29]([C:35]3[CH:40]=[C:39]([C:41]([F:44])([F:42])[F:43])[N:38]=[C:37]([N:45]([CH3:47])[CH3:46])[N:36]=3)[CH2:30][C@@H:31]1[CH2:32][CH2:33][NH:26][CH2:27]2

Participants

5

Reactant 4

HCID 2389382-ChloroquinoxalineHCID 179991074-Chloro-N,N-dimethyl-6-(trifluoromethyl)pyrimidin-2-amineHCID 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 69932407(1R,6S)-[4-(3,8-diaza-bicyclo[4.2.0]oct-8-yl)-6-trifluoromethyl-pyrimidin-2-yl]-dimethyl-amine

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-6-trifluoromethyl-pyrimidin-2-yl)-dimethyl-amine for 2-chloro-quinoxaline in Step A. MS (ESI) mass calcd. for C13H18F3N5, 301.31. m/z found 302.1 [M+H]+. 1H NMR (CDCl3): 9.04 (s, 1H), 5.98-5.63 (m, 1H), 4.56 (dd, J=4.9, 3.1, 1H), 3.99 (t, J=7.8, 1H), 3.88-3.70 (m, 2H), 3.68-3.37 (m, 2H), 3.33-3.17 (m, 1H), 3.16-3.00 (m, 6H), 2.95-2.74 (m, 1H), 2.33-1.85 (m, 2H).

Sources & evidence

ORD record
ord-36fd0eebb1a348529411b350af0a74de
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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