4-Chloro-6-methylpyrimidine → (1R,6S)-3-{[5-Fluoro-2-(2H-1,2,3-triazol-2-yl)phenyl]carbonyl}-8-(6-methylpyrimidin-4-yl)-3,8-diazabicyclo[4.2.0]octane

HRID 1193206Notes

Reaction equation

HRID 1193206 reaction equation
C12[N:8]([C:9]3C=N[C:16]4[C:11](=CC=[CH:14][CH:15]=4)[N:10]=3)CC1CCNC2.[C@@H:19]12[NH:26][CH2:25][C@@H:24]1[CH2:23][CH2:22][N:21]([C:27]([C:29]1[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:30]=1[N:36]1[N:40]=[CH:39][CH:38]=[N:37]1)=[O:28])[CH2:20]2.ClC1C=C(C)N=CN=1>>[F:35][C:33]1[CH:32]=[CH:31][C:30]([N:36]2[N:40]=[CH:39][CH:38]=[N:37]2)=[C:29]([C:27]([N:21]2[CH2:22][CH2:23][C@@H:24]3[C@@H:19]([N:26]([C:11]4[CH:16]=[C:15]([CH3:14])[N:8]=[CH:9][N:10]=4)[CH2:25]3)[CH2:20]2)=[O:28])[CH:34]=1

Participants

4

Reactant 3

HCID 5817964-Chloro-6-methylpyrimidineHCID 67116560(1R,6S)-3,8-diazabicyclo[4.2.0]octan-3-yl(5-fluoro-2-(2H-1,2,3-triazol-2-yl)phenyl)methanoneHCID 671166512-(3,8-Diaza-bicyclo[4.2.0]oct-8-yl)-quinoxaline

Product 1

HCID 67116572(1R,6S)-3-{[5-Fluoro-2-(2H-1,2,3-triazol-2-yl)phenyl]carbonyl}-8-(6-methylpyrimidin-4-yl)-3,8-diazabicyclo[4.2.0]octane

Procedure

The title compound was prepared in a manner analogous to Intermediate 2, Step A, using (1R,6S)-3,8-diazabicyclo[4.2.0]octan-3-yl(5-fluoro-2-(2H-1,2,3-triazol-2-yl)phenyl)methanone and 4-chloro-6-methylpyrimidine. MS (ESI) mass calcd. for C20H20FN7O, 393.4; m/z found, 394.2 [M+H]+.

Sources & evidence

ORD record
ord-ab62a034891b40868e2ffa1944168e31
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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