Benzenesulfonyl chloride, 2,4-dimethyl- → (1R,6S)2-[3-(2,4-Dimethyl-benzenesulfonyl)-3,8-diaza-bicyclo[4.2.0]oct-8-yl]-quinoxaline

HRID 1193138Notes

Reaction equation

HRID 1193138 reaction equation
[C@@H:1]12[N:8]([C:9]3[CH:18]=[N:17][C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[N:10]=3)[CH2:7][C@@H:6]1[CH2:5][CH2:4][NH:3][CH2:2]2.C1(C2C=CN=C(N3C4C(CCNC4)C3)N=2)C=CC=CC=1.[CH3:39][C:40]1[CH:45]=[C:44]([CH3:46])[CH:43]=[CH:42][C:41]=1[S:47](Cl)(=[O:49])=[O:48].CC1C=CC(C)=CC=1S(Cl)(=O)=O>>[CH3:39][C:40]1[CH:45]=[C:44]([CH3:46])[CH:43]=[CH:42][C:41]=1[S:47]([N:3]1[CH2:4][CH2:5][C@@H:6]2[C@@H:1]([N:8]([C:9]3[CH:18]=[N:17][C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[N:10]=3)[CH2:7]2)[CH2:2]1)(=[O:48])=[O:49]

Participants

5

Reactant 4

HCID 69109Benzenesulfonyl chloride, 2,4-dimethyl-HCID 87910Benzenesulfonyl chloride, 2,5-dimethyl-HCID 671167498-(4-Phenyl-pyrimidin-2-yl)-3,8-diaza-bicyclo[4.2.0]octaneHCID 68156918(1R,6S)-2-(3,8-diaza-bicyclo[4.2.0]oct-8-yl)quinoxaline

Product 1

HCID 52920409(1R,6S)2-[3-(2,4-Dimethyl-benzenesulfonyl)-3,8-diaza-bicyclo[4.2.0]oct-8-yl]-quinoxaline

Procedure

The title compound was prepared in a manner analogous to Example 19, substituting (1R,6S)-2-(3,8-diaza-bicyclo[4.2.0]oct-8-yl)-quinoxaline (Intermediate 3) for 8-(4-phenyl-pyrimidin-2-yl)-3,8-diaza-bicyclo[4.2.0]octane and 2,4-dimethyl-benzenesulfonyl chloride for 2,5-dimethyl-benzenesulfonyl chloride. MS (ESI) mass calcd. for C22H24N4O2S, 408.52; m/z found 409.2 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.96 (s, 1H), 7.86 (dd, J=8.2, 1.3, 1H), 7.66 (d, J=1.2, 1H), 7.58-7.52 (m, 1H), 7.49 (dd, J=8.4, 1.1, 1H), 7.43-7.37 (m, 1H), 6.62-6.48 (m, 2H), 4.69-4.61 (m, 1H), 4.22-3.95 (m, 4H), 3.85-3.74 (m, 1H), 3.69-3.59 (m, 1H), 3.41 (dd, J=14.0, 2.8, 1H), 3.05-2.89 (m, 1H), 2.42 (s, 3H), 2.30-2.14 (m, 1H), 2.09 (s, 3H), 2.05-1.92 (m, 1H).

Sources & evidence

ORD record
ord-9210dae6fb4f43658c3a54871bed78db
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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