p-Toluenesulfonic acid → 5-chloro-N4-(2-(difluoromethylsulfonyl)phenyl)-N2-(2-isopropoxy-5-methyl-4-(piperidin-4-yl)phenyl)pyrimidine-2,4-diamine

HRID 2046961Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15]([CH:18]([F:20])[F:19])(=[O:17])=[O:16])[C:5]([Cl:21])=[CH:4][N:3]=1.[CH:22]([O:25][C:26]1[CH:32]=[C:31]([CH:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)[C:30]([CH3:39])=[CH:29][C:27]=1[NH2:28])([CH3:24])[CH3:23].CC1C=CC(S(O)(=O)=O)=CC=1>C(O)(C)C>[Cl:21][C:5]1[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15]([CH:18]([F:20])[F:19])(=[O:17])=[O:16])=[N:7][C:2]([NH:28][C:27]2[CH:29]=[C:30]([CH3:39])[C:31]([CH:33]3[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]3)=[CH:32][C:26]=2[O:25][CH:22]([CH3:24])[CH3:23])=[N:3][CH:4]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To a suspension of 2,5-dichloro-N-(2-(difluoromethylsulfonyl)phenyl)-pyrimidin-4-amine (0.5 mmol) in 1 mL of isopropanol, was added 2-isopropoxy-5-methyl-4-(piperidin-4-yl)aniline (0.5 mmol) and 4-methylbenzenesulfonic acid (0.5 mmol). The suspension was stirred at 150° C. for 3 hours. After work-up and prep-HPLC, product was obtained. MS (ES+): 566.17 (M+1)+.

Workup

customAfter work-up and prep-HPLC, product was obtained

Sources & evidence

ORD record: ord-f8b1637c05ec4705b56cc93e23f0b90d
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592432B2

Reaction notes

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