3-[3-(7-Formylimidazo[1,2-alpha]pyridin 3-yl)phenyl]thiophene-2-carbonitrile → 3-[3-(7-(2-Dimethylaminoethoxy)iminomethylimidazo[1,2-alpha]pyridin-3-yl)phenyl]thiophene-2-carbonitrile
Reaction equation
Cl.[CH3:2][N:3]([CH3:8])[CH2:4][CH2:5][O:6][NH2:7].[CH:9]([C:11]1[CH:16]=[CH:15][N:14]2[C:17]([C:20]3[CH:21]=[C:22]([C:26]4[CH:30]=[CH:29][S:28][C:27]=4[C:31]#[N:32])[CH:23]=[CH:24][CH:25]=3)=[CH:18][N:19]=[C:13]2[CH:12]=1)=O>>[CH3:2][N:3]([CH3:8])[CH2:4][CH2:5][O:6][N:7]=[CH:9][C:11]1[CH:16]=[CH:15][N:14]2[C:17]([C:20]3[CH:21]=[C:22]([C:26]4[CH:30]=[CH:29][S:28][C:27]=4[C:31]#[N:32])[CH:23]=[CH:24][CH:25]=3)=[CH:18][N:19]=[C:13]2[CH:12]=1Participants
3
Procedure
The title compound was prepared in a similar manner to that described in Example 14 using O-(2-dimethylaminoethyl)hydroxylamine hydrochloride (144 mg, 0.82 mmol) and 3-[3-(7-formylimidazo[1,2-α]pyridin-3-yl)phenyl]thiophene-2-carbonitrile (90 mg, 0.27 mmol) to afford a yellow solid (42 mg, 38%), essentially as a single geometric isomer, m.p. 74-75° C. 1H NMR (360 MHz, CDCl3) δH 2.33 (6H, s), 2.67-2.71 (2H, m), 4.30-4.34 (2H, m), 7.33-7.37 (2H, m), 7.63-7.70 (4H, m), 7.79 (1H, s), 7.91 (1H, s), 8.15 (1H, s), 8.45 (1H, d, J 7); m/z (ES+) 416 (M++H).
Sources & evidence
- ORD record
- ord-38be777e8e764f90b2b439cf543c68ef
- Source dataset
- uspto-grants-2005_03
- Patent number
- US06872731B2
Reaction notes
Loading…