3-{[3-(Aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile → HCID 178486283, compound

HRID 1875262Notes

Reaction equation

HRID 1875262 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([S:18]([NH:21][CH3:22])(=[O:20])=[O:19])[N:5](COCC[Si](C)(C)C)[C:6]=1[C:7]([OH:9])=O.[NH2:23][CH2:24][C:25]1[C:26]([F:42])=[C:27]([O:32][C:33]2[CH:34]=[C:35]([CH:38]=[C:39]([Cl:41])[CH:40]=2)[C:36]#[N:37])[C:28]([Cl:31])=[CH:29][CH:30]=1>>[Cl:1][C:2]1[N:3]=[C:4]([S:18]([NH:21][CH3:22])(=[O:19])=[O:20])[NH:5][C:6]=1[C:7]([NH:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([O:32][C:33]2[CH:34]=[C:35]([C:36]#[N:37])[CH:38]=[C:39]([Cl:41])[CH:40]=2)[C:26]=1[F:42])=[O:9]

Participants

3

Reactant 2

HCID 594513923-{[3-(Aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrileHCID 70937195HCID 70937195, compound

Product 1

HCID 178486283HCID 178486283, compoundYield 54%

Procedure

4-chloro-2-[(methylamino)sulfonyl]-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxylic acid (0.12 mmol) and 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile (0.040 g, 0.13 mmol) were employed using a procedure similar to that described herein to provide the title compound (0.034 g, 54%) 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 (s, 1H), 7.40 (s, 2H), 7.27 (s, 1H), 7.24 (s, 1H), 4.63 (s, 2H), 2.70 (s, 3 H). ES-LCMS: m/z 532.1, 534.1, 536.0 (M+1).

Sources & evidence

ORD record
ord-f9627f2cb6524692a8e33a14068a43ea
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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