2-{[3-(Aminomethyl)-6-chloro-2-fluorophenyl]oxy}-6-chloro-4-pyridinecarbonitrile → HCID 178432876, compound
Reaction equation
[NH2:1][CH2:2][C:3]1[C:4]([F:20])=[C:5]([O:10][C:11]2[CH:16]=[C:15]([C:17]#[N:18])[CH:14]=[C:13]([Cl:19])[N:12]=2)[C:6]([Cl:9])=[CH:7][CH:8]=1.[Cl:21][C:22]1[N:23]=[C:24]([CH3:30])[NH:25][C:26]=1[C:27](O)=[O:28]>>[Cl:21][C:22]1[N:23]=[C:24]([CH3:30])[NH:25][C:26]=1[C:27]([NH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[C:5]([O:10][C:11]2[CH:16]=[C:15]([C:17]#[N:18])[CH:14]=[C:13]([Cl:19])[N:12]=2)[C:4]=1[F:20])=[O:28]Participants
3
Procedure
The previously described 2-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-6-chloro-4-pyridinecarbonitrile (0.040 g, 0.13 mmol) and 4-chloro-2-methyl-1H-imidazole-5-carboxylic acid (0.023 g, 0.14 mmol) were employed in a similar process described herein to prepare the title compound (0.037 g, 64%) as a white solid after purification by Reverse-Phase HPLC (water:acetonitrile with 0.1% TFA) followed by neutralization. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 11.92 (br. s., 1H) 7.13-7.34 (m, 5H) 4.72 (d, J=5.91 Hz, 2H) 2.36 (s, 3H). ES-LCMS: m/z 453.9, 456.0 (M+1).
Sources & evidence
- ORD record
- ord-6d0a3cd0ecdb4c34853f6fb1c0713c70
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08304419B2
Reaction notes
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