Hydrochloric Acid → HCID 59495697, compound
Reaction equation
[F:1][C:2]1[CH:11]=[C:10]([C:12]2[N:16]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]4[CH3:29])=[C:19]([NH:30][S:31]([CH3:34])(=[O:33])=[O:32])[CH:18]=3)[O:14][N:13]=2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].Cl>>[F:1][C:2]1[CH:11]=[C:10]([C:12]2[N:16]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]4[CH3:29])=[C:19]([NH:30][S:31]([CH3:34])(=[O:33])=[O:32])[CH:18]=3)[O:14][N:13]=2)[CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]Participants
Procedure
The title compound was prepared following procedure described for example 4, step 2, but starting from methyl 2-fluoro-4-(5-{4-(2-methylpiperidin-1-yl)-3-[(methylsulfonyl)amino]phenyl}-1,2,4-oxadiazol-3-yl)benzoate, obtained in step 1 (280 mg; 0.57 mmol). After 18 h, HCl (573.14 μL; 5 M; 2.87 mmol) was added and the mixture was evaporated to dryness. The solid was triturated in water and filtered to afford the title compound as a light yellow powder (220 mg; 80%). 1H NMR (DMSO-d6, 300 MHz) δ 13.6 (bs, 1H), 8.67, (bs, 1H), 8.20 (d, 2.1 Hz, 1H), 8.08, (t, J=7.9 Hz, 1H), 8 (dd, J=8.1, 1.6 Hz, 1H), 7.95-7.90 (m, 2H), 7.55 (d, J=8.4 Hz, 1H), 3.22 (s, 3H), 3.18-3.12 (m, 1H), 2.92-2.88 (m, 1H), 2.65-2.57 (m, 1H), 1.82-1.68 (m, 4H), 1.53-1.44 (m, 2H), 0.81 (d, J=6 Hz, 3H). LC/MS (Method B): 475.3 (M+H)+. HPLC (Method A) Rt 4.68 min (purity: 97.0%). CHN analysis: [C22H23N4O5SF] Calculated: C, 55.69%; H, 4.89%; N, 11.81%. Found: C, 55.41%; H, 4.76%; N, 11.70%.
Workup
- customThe title compound was prepared following procedure
- customobtained in step 1 (280 mg; 0.57 mmol)
- customthe mixture was evaporated to dryness
- customThe solid was triturated in water
- filtrationfiltered
Sources & evidence
- ORD record
- ord-2a1d1cd10ee442c38749f21926d6ffc0
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08202865B2
Reaction notes
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