3-{[3-(Aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile → HCID 178486155, compound

HRID 1875256Notes

Reaction equation

HRID 1875256 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([S:18]([N:21]([CH3:23])[CH3:22])(=[O:20])=[O:19])[N:5](COCC[Si](C)(C)C)[C:6]=1[C:7]([OH:9])=O.[NH2:24][CH2:25][C:26]1[C:27]([F:43])=[C:28]([O:33][C:34]2[CH:35]=[C:36]([CH:39]=[C:40]([Cl:42])[CH:41]=2)[C:37]#[N:38])[C:29]([Cl:32])=[CH:30][CH:31]=1>>[Cl:1][C:2]1[N:3]=[C:4]([S:18]([N:21]([CH3:22])[CH3:23])(=[O:19])=[O:20])[NH:5][C:6]=1[C:7]([NH:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([O:33][C:34]2[CH:35]=[C:36]([C:37]#[N:38])[CH:39]=[C:40]([Cl:42])[CH:41]=2)[C:27]=1[F:43])=[O:9]

Participants

3

Reactant 2

HCID 594513923-{[3-(Aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrileHCID 70937207HCID 70937207, compound

Product 1

HCID 178486155HCID 178486155, compoundYield 59.4%

Procedure

4-chloro-2-[(dimethylamino)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 (0.045 g, 0.14 mmol) were employed using a procedure similar to that described herein to provide the title compound (0.039 g, 59%) 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 7.54 (s, 1H), 7.34-7.42 (m, 2H), 7.26 (s, 1H), 7.22 (s, 1H), 4.64 (s, 2H), 2.86 (s, 6H). ES-LCMS: m/z 546.1, 547.9, 550.0 (M+1).

Sources & evidence

ORD record
ord-42061cd5a4e94e3f8aa358176d9b0e10
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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