3-{[3-(Aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile → HCID 178433280, compound

HRID 1875219Notes

Reaction equation

HRID 1875219 reaction equation
[CH3:1][C:2]1[N:6](COCC[Si](C)(C)C)[CH:5]=[N:4][C:3]=1[C:15]([OH:17])=O.[NH2:18][CH2:19][C:20]1[C:21]([F:37])=[C:22]([O:27][C:28]2[CH:29]=[C:30]([CH:33]=[C:34]([Cl:36])[CH:35]=2)[C:31]#[N:32])[C:23]([Cl:26])=[CH:24][CH:25]=1>>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][NH:18][C:15]([C:3]2[NH:4][CH:5]=[N:6][C:2]=2[CH3:1])=[O:17])=[C:21]([F:37])[C:22]=1[O:27][C:28]1[CH:29]=[C:30]([C:31]#[N:32])[CH:33]=[C:34]([Cl:36])[CH:35]=1

Participants

3

Reactant 2

HCID 594513923-{[3-(Aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrileHCID 59677338HCID 59677338, compound

Product 1

HCID 178433280HCID 178433280, compoundYield 254.4%

Procedure

The procedure and process are similar to that described herein except that 5-methyl-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-4-carboxylic acid (0.077 g, 0.30 mmol) and 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile (0.093 g, 0.30 mmol) were employed to provide the title compound (0.32 g, 25% overall) as a white solid after deprotection and purification by Reverse-Phase HPLC (water:acetonitrile with 0.1% NH4OH. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.29 (br. s., 1H), 8.43 (t, J=5.84 Hz, 1H), 7.82 (s, 1H), 7.57 (s, 1H), 7.44-7.54 (m, 3H), 7.32 (t, J=7.83 Hz, 1H), 4.45 (d, J=6.04 Hz, 2H), 2.43 (s, 3H). ES-LCMS: m/z 419.0, 421.0 (M+1).

Sources & evidence

ORD record
ord-e15c2ad9a97e4ad9adc14bbf6d6ec49d
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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