cis-3-Boc-3,8-diazabicyclo[4.2.0]octane → (1S,6R)-3-(4,6-Dimethylpyrimidin-2-yl)-8-{[2-fluoro-6-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]carbonyl}-3,8-diazabicyclo[4.2.0]octane

HRID 2175042Notes

Reaction equation

HRID 2175042 reaction equation
[C@H:1]12[N:8](C(C3C=CC=CC=3C3ON=C(C)N=3)=O)C[C@H:6]1[CH2:5][CH2:4]N[CH2:2]2.C(O[C:28]([N:30]1[CH2:37][CH2:36][C@@H:35]2[C@@H:32]([NH:33][CH2:34]2)[CH2:31]1)=O)(C)(C)C.[F:38][C:39]1[CH:47]=[CH:46][CH:45]=[C:44]([C:48]2[O:52][N:51]=[C:50]([CH3:53])[N:49]=2)[C:40]=1[C:41]([OH:43])=O.CC1N=C(C2C=CC=CC=2C(O)=O)O[N:56]=1>>[CH3:4][C:5]1[CH:6]=[C:1]([CH3:2])[N:8]=[C:28]([N:30]2[CH2:37][CH2:36][C@H:35]3[C@H:32]([N:33]([C:41]([C:40]4[C:44]([C:48]5[O:52][N:51]=[C:50]([CH3:53])[N:49]=5)=[CH:45][CH:46]=[CH:47][C:39]=4[F:38])=[O:43])[CH2:34]3)[CH2:31]2)[N:56]=1

Participants

5

Reactant 4

HCID 16099092cis-3-Boc-3,8-diazabicyclo[4.2.0]octaneHCID 231463052-(3-Methyl-1,2,4-oxadiazol-5-yl)benzoic acidHCID 67086669(1S,6R)-3,8-Diazabicyclo[4.2.0]octan-8-yl(2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl)methanoneHCID 670868322-Fluoro-6-(3-methyl-1,2,4-oxadiazol-5-yl)benzoic acid

Product 1

HCID 67086602(1S,6R)-3-(4,6-Dimethylpyrimidin-2-yl)-8-{[2-fluoro-6-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]carbonyl}-3,8-diazabicyclo[4.2.0]octane

Procedure

The title compound was prepared in a manner analogous to Intermediate 12, Step B substituting Intermediate 34 for (1R,6S) 3,8-diaza-bicyclo[4.2.0]octane-3-carboxylic acid tert-butyl ester and Intermediate 16 for 2-(3-methyl-1,2,4-oxadiazol-5-yl)benzoic acid. MS (ESI) mass calculated for C22H23FN6O2, 422.19; m/z found, 423.2.

Sources & evidence

ORD record
ord-279fa587ab00452c97ba056867be34ab
Source dataset
uspto-grants-2015_06
Patent number
US09062044B2

Reaction notes

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