2-Chloro-6-fluorobenzylamine → 2-[(2-Chloro-6-fluorobenzyl)amino]-N-(2-methoxypyrimidin-5-yl)benzenesulfonamide

HRID 1772896

Reaction equation

HRID 1772896 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8](Cl)(=[O:10])=[O:9].[NH2:12][C:13]1[CH:14]=[N:15][C:16]([O:19][CH3:20])=[N:17][CH:18]=1.[Cl:21][C:22]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:23]=1[CH2:24][NH2:25]>O1CCOCC1.CC#N>[Cl:21][C:22]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:23]=1[CH2:24][NH:25][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:12][C:13]1[CH:14]=[N:15][C:16]([O:19][CH3:20])=[N:17][CH:18]=1)(=[O:10])=[O:9]

Participants

6

Reactant 3

HCID 848332-Chloro-6-fluorobenzylamineHCID 1377612-Fluorobenzenesulphonyl chlorideHCID 3529042-Methoxypyrimidin-5-amine

Product 1

HCID 900219032-[(2-Chloro-6-fluorobenzyl)amino]-N-(2-methoxypyrimidin-5-yl)benzenesulfonamideYield 9%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Procedure

The title compound (106 mg, impure, used without further purification) was prepared in two steps from 2-fluorobenzenesulfonyl chloride (0.46 mL, 3.5 mmol) and 5-amino-2-methoxypyrimidine (482 mg, 3.85 mmol) in 1,4-dioxane at 100° C.; followed by 2-chloro-6-fluorobenzyl amine (0.36 mL, 2.8 mmol) in MeCN (1.5 mL) at 180° C. in a Biotage Initiator microwave reactor using the methods of (IntB1).

Sources & evidence

ORD record
ord-b2ab220cfe2c403abf927cfa50f04389
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Linked notes

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