2-Ethyl-4-methyl-1,3-oxazole-5-carboxylic acid → 2-(4-(4-(5-(2-Ethyl-4-methyloxazole-5-carboxamido)pyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetic acid
Reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]34[CH2:21][CH2:20][C:17]([CH2:22][C:23]([O:25]C)=[O:24])([CH2:18][CH2:19]3)[O:16][CH2:15]4)=[CH:10][CH:9]=2)=[N:6][CH:7]=1.[CH2:27]([C:29]1[O:30][C:31]([C:35](O)=[O:36])=[C:32]([CH3:34])[N:33]=1)[CH3:28]>>[CH2:27]([C:29]1[O:30][C:31]([C:35]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[CH:9]=[CH:10][C:11]([C:14]45[CH2:19][CH2:18][C:17]([CH2:22][C:23]([OH:25])=[O:24])([CH2:20][CH2:21]4)[O:16][CH2:15]5)=[CH:12][CH:13]=3)=[N:6][CH:7]=2)=[O:36])=[C:32]([CH3:34])[N:33]=1)[CH3:28]Participants
3
Procedure
The title compound was prepared analogous to Example 12, starting from methyl 2-(4-(4-(5-aminopyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate (114 mg, 0.32 mmol) and 2-ethyl-4-methyloxazole-5-carboxylic acid (60.2 mg, 0.39 mmol). The crude product was purified on prep-HPLC to afford the title compound as off-white solid after drying (28 mg, 17% yield). HR/MS (M+H)+ found 476.2166. calc. 476.2185, RT: 2.76 (Condition L). 1H NMR (400 MHz, DMSO-d6) δ ppm 10.55 (s, 1H), 8.98 (s, 1H), 8.24 (d, J=8.0 Hz, 1H), 8.01 (d, J=12.0 Hz, 2H), 7.95 (d, J=12.0 Hz, 1H), 7.43 (d, J=8.0 Hz, 2H), 3.91 (s, 2H), 2.86 (q, J=8.0 Hz, 2H), 2.36 (s, 2H), 2.25 (s, 2H), 2.09-1.90 (m, 8H), 1.36 (t, J=8.0 Hz, 3H).
Workup
- customThe title compound was prepared analogous to Example 12
- customThe crude product was purified on prep-HPLC
Sources & evidence
- ORD record
- ord-49765b81f11a404eb783390e2cd4b489
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08993619B2
Reaction notes
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