4-chloro-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxylic acid → HCID 178509857, compound
Reaction equation
[NH2:1][CH2:2][C:3]1[C:4]([F:19])=[C:5]([O:10][C:11]2[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=2)[C:14]#[N:15])[C:6]([Cl:9])=[CH:7][CH:8]=1.[Cl:20][C:21]1[N:22]=[CH:23][N:24](COCC[Si](C)(C)C)[C:25]=1[C:26](O)=[O:27]>>[Cl:20][C:21]1[N:22]=[CH:23][NH:24][C:25]=1[C:26]([NH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[C:5]([O:10][C:11]2[CH:18]=[CH:17][CH:16]=[C:13]([C:14]#[N:15])[CH:12]=2)[C:4]=1[F:19])=[O:27]Participants
3
Procedure
The previously described 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}benzonitrile (0.28 mmol) and 4-chloro-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxylic acid (0.055 g, 0.20 mmol) were employed in a similar process described herein to prepare the title compound (0.056 g, 69%) as a white solid after deprotection and purification by Reverse-Phase HPLC (water:acetonitrile with 0.1% TFA). 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.73 (s, 1H) 7.42-7.55 (m, 2H) 7.29-7.42 (m, 2H) 7.17-7.27 (m, 2H) 4.65 (s, 2H). ES-LCMS: m/z 405.0, 407.0 (M+1).
Sources & evidence
- ORD record
- ord-bf1896748d3946f39cc53823990942fb
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08304419B2
Reaction notes
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