N-bromobutanimide → 5-Bromo-3-(6-fluoro-1,3-benzoxazol-2-yl)pyrazin-2-amine
Reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]=[C:7]([C:9]3[C:10]([NH2:15])=[N:11][CH:12]=[CH:13][N:14]=3)[O:8][C:4]=2[CH:3]=1.[Br:18]N1C(=O)CCC1=O>>[Br:18][C:13]1[N:14]=[C:9]([C:7]2[O:8][C:4]3[CH:3]=[C:2]([F:1])[CH:17]=[CH:16][C:5]=3[N:6]=2)[C:10]([NH2:15])=[N:11][CH:12]=1Participants
Procedure
3-(6-fluoro-1,3-benzoxazol-2-yl)pyrazin-2-amine (300 mg) was reacted with 1-bromopyrrolidine-2,5-dione using analogous procedures to those described in the starting material portion of Example 17 to give 5-bromo-3-(6-fluoro-1,3-benzoxazol-2-yl)pyrazin-2-amine (150 mg), which was reacted with tert-butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazol-1-yl]piperidine-1-carboxylate (183 mg) to give tert-butyl 4-[4-[5-amino-6-(6-fluoro-1,3-benzoxazol-2-yl)pyrazin-2-yl]pyrazol-1-yl]piperidine-1-carboxylate (150 mg) according to the starting material portion of the procedure described in Example 17, except that 1,1′-bis(diphenylphosphino)ferrocenedichloropalladium(II) was used as the catalyst, 2M sodium carbonate as the base and dioxane:toluene (1:1) as the solvent. NMR Spectrum: (400 MHz, DMSOd6) 8.50 (s, 1H), 8.25 (s, 1H), 8.05 (s, 1H), 7.80 (dd, 1H), 7.50 (dd, 1H), 7.20 (dd, 1H), 4.40 (m, 1H), 4.20 (m, 1H), 3.00 (m, 2H), 2.10 (m, 1H), 1.90 (m, 3H), 1.50 (s, 9H) Mass spectrum: M+H+ 480.
Sources & evidence
- ORD record
- ord-921b47f46c2c4cf7a460c6a416ccbbe9
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08017611B2
Reaction notes
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