Methylamine → 4-{4-chloro-6-[4-(methylsulfonyl)phenyl]-2-(trifluoromethyl)pyrimidin-5-yl}-N-methylbenzenesulfonamide

HRID 1966333Notes

Reaction equation

[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=2)=[C:6]([C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=2)[N:5]=[C:4]([C:28]([F:31])([F:30])[F:29])[N:3]=1.[CH3:32][NH2:33]>ClCCl>[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([NH:33][CH3:32])(=[O:16])=[O:15])=[CH:10][CH:9]=2)=[C:6]([C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=2)[N:5]=[C:4]([C:28]([F:31])([F:30])[F:29])[N:3]=1

Participants

Conditions

Temperature: 5 °C

Procedure

To a solution of 4-{4-chloro-6-[4-(methylsulfonyl)phenyl]-2-(trifluoromethyl)pyrimidin-5-yl}benzenesulfonyl chloride (0.5 g, 0.98 mmol, prepared according to the procedure described for example 3) in dichloromethane (5 ml) was added methylamine solution (0.08 ml, 0.98 mmol, 40% aqueous solution) under stirring at 0-10° C. After 15 minutes of the stirring, TLC confirmed the completion of the reaction. Subsequently the solvent was distilled off under reduced pressure and the solid thus obtained was filtered, washed thoroughly with cold water to yield the title compound (0.446 g, yield 90.1%, purity by HPLC 98.1%). m.p: 226-230° C. 1H-NMR (400 MHz, DMSO-d6) δ: 2.09-2.10 (d, 3H), 3.1 (s, 3H), 7.43-7.44 (m, 1H, D2O exchangeable), 7.54-7.56 (d, 2H), 7.69-7.81 (m, 4H), 7.86-7.88 (d, 2H). IR (KBr) cm−1: 3335, 1562 and 1530; MS m/z: 506.1 (M++1).

Workup

customthe completion of the reaction
distillationSubsequently the solvent was distilled off under reduced pressure
customthe solid thus obtained
filtrationwas filtered
washwashed thoroughly with cold water

Sources & evidence

ORD record: ord-d9d72e89cbd84899973d35719a0703a8
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420653B2

Reaction notes

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