Hydrochloric Acid → HCID 12069228, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9](SC)[O:8][C:5]2=[N:6][CH:7]=1.Br[C:14]1[CH:15]=[C:16]([N+:21]([O-])=O)[C:17](O)=[N:18][CH:19]=1.Cl.C(O[CH2:29][CH3:30])(=O)C>>[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([N:21]3[CH:15]4[CH2:29][CH2:30][N:18]([CH2:19][CH2:14]4)[CH2:17][CH2:16]3)[O:8][C:5]2=[N:6][CH:7]=1Participants
5
Procedure
The title compound was prepared from 6-bromo-2-methylsulfanyl-oxazolo[5,4-b]pyridine (prepared from 5-bromo-2-hydroxy-3-nitropyridine by the methods described in Examples 4, 5 and 7) by the procedure described in Example 9 in 64% yield: 1H NMR (CDCl3, 400 MHz) δ 7.90 (d, 1H, J=2.1 Hz), 7.59 (d, 1H, J=2.1 Hz), 4.50-4.49 (m, 1h), 3.91 (t, 2H, J=5.8 Hz), 3.18-3.11 (m, 4H), 3.03-2.96 (m, 2H), 2.16-2.08 (m, 2H), 1.85-1.76 (m, 2H); 13C NMR (CDCl3, 100 MHz) δ 161.4, 138.8, 125.3, 121.4, 116.7, 116.2, 57.0, 50.6, 46.4, 44.3, 26.8; MS (Cl) m/z 323.0 (M+1); HPLC retention time=3.08 min. The hydrochloride salt was prepared by diluting in ethyl acetate and adding a 2.5 N HCl solution in ethyl acetate: mp>300° C.
Sources & evidence
- ORD record
- ord-c2687c40d75346869d14dcd6e2722954
- Source dataset
- uspto-grants-2004_10
- Patent number
- US06809094B2
Reaction notes
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