4-chloro-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxylic acid → HCID 178492275, compound
Reaction equation
[NH2:1][CH2:2][C:3]1[C:4]([F:21])=[C:5]([O:10][C:11]2[CH:12]=[C:13]([CH:16]=[C:17]([O:19][CH3:20])[CH:18]=2)[C:14]#[N:15])[C:6]([Cl:9])=[CH:7][CH:8]=1.[Cl:22][C:23]1[N:24]=[CH:25][N:26](COCC[Si](C)(C)C)[C:27]=1[C:28](O)=[O:29]>>[Cl:22][C:23]1[N:24]=[CH:25][NH:26][C:27]=1[C:28]([NH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[C:5]([O:10][C:11]2[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:13]([C:14]#[N:15])[CH:12]=2)[C:4]=1[F:21])=[O:29]Participants
3
Procedure
3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-(methyloxy)benzonitrile (0.30 mmol) and 4-chloro-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxylic acid (0.083 g, 0.30 mmol) were employed in a similar process described herein to prepare the title compound (0.096 g, 74%) 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 7.74 (s, 1H) 7.29-7.46 (m, 2H) 7.04 (s, 1H) 6.69-6.83 (m, 2H) 4.65 (s, 2H) 3.83 (s, 3H). ES-LCMS: m/z 435.8, 437.7 (M+1).
Sources & evidence
- ORD record
- ord-1a6e8716e388412693d0c26a1805c4d9
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08304419B2
Reaction notes
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