3-{[3-(Aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile → HCID 178509952, compound

HRID 1875267Notes

Reaction equation

HRID 1875267 reaction equation
[NH2:1][S:2]([C:5]1[N:6](COCC[Si](C)(C)C)[C:7]([C:11]([OH:13])=O)=[C:8]([Cl:10])[N:9]=1)(=[O:4])=[O:3].[NH2:22][CH2:23][C:24]1[C:25]([F:41])=[C:26]([O:31][C:32]2[CH:33]=[C:34]([CH:37]=[C:38]([Cl:40])[CH:39]=2)[C:35]#[N:36])[C:27]([Cl:30])=[CH:28][CH:29]=1>>[NH2:1][S:2]([C:5]1[NH:6][C:7]([C:11]([NH:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([O:31][C:32]3[CH:33]=[C:34]([C:35]#[N:36])[CH:37]=[C:38]([Cl:40])[CH:39]=3)[C:25]=2[F:41])=[O:13])=[C:8]([Cl:10])[N:9]=1)(=[O:3])=[O:4]

Participants

3

Reactant 2

HCID 594513923-{[3-(Aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrileHCID 70937131HCID 70937131, compound

Product 1

HCID 178509952HCID 178509952, compoundYield 41%

Procedure

2-(aminosulfonyl)-4-chloro-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxylic acid (0.26 mmol) and 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile (0.089 g, 0.29 mmol) were employed using a procedure similar to that described herein to provide the title compound (0.055 g, 41%) as a white solid after deprotection and purification by Reverse-Phase HPLC (water:acetonitrile with 0.1% formic acid). 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.55 (t, 1H), 7.35-7.43 (m, 2H), 7.27 (t, J=2.0 Hz, 1H), 7.24 (s, 1H), 4.63 (s, 2H). ES-LCMS: m/z 516.0, 518.0, 519.9 (M−1).

Sources & evidence

ORD record
ord-c0c59936f7b547ecb389dd51cd76a60b
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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