p-Toluenesulfonic acid → n2-(2-Isopropoxy-5-methyl-4-(1-methylpiperidin-4-yl)phenyl)-n4-(2-(isopropylsulfonyl)phenyl)pyrazolo[1,5-a][1,3,5]triazine-2,4-diamine

HRID 1896085Notes

Reaction equation

[CH:1]([S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14]1[N:19]2[N:20]=[CH:21][CH:22]=[C:18]2[N:17]=[C:16](S(C)(=O)=O)[N:15]=1)(=[O:6])=[O:5])([CH3:3])[CH3:2].[CH:27]([O:30][C:31]1[CH:37]=[C:36]([CH:38]2[CH2:43][CH2:42][N:41]([CH3:44])[CH2:40][CH2:39]2)[C:35]([CH3:45])=[CH:34][C:32]=1[NH2:33])([CH3:29])[CH3:28].CC1C=CC(S(O)(=O)=O)=CC=1>C(O)(C)C>[CH:27]([O:30][C:31]1[CH:37]=[C:36]([CH:38]2[CH2:39][CH2:40][N:41]([CH3:44])[CH2:42][CH2:43]2)[C:35]([CH3:45])=[CH:34][C:32]=1[NH:33][C:16]1[N:15]=[C:14]([NH:13][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[S:4]([CH:1]([CH3:3])[CH3:2])(=[O:6])=[O:5])[N:19]2[N:20]=[CH:21][CH:22]=[C:18]2[N:17]=1)([CH3:29])[CH3:28]

Participants

Conditions

Temperature: 150 °C

Procedure

To a suspension of N-(2-(isopropylsulfonyl)phenyl)-2-(methysulfonyl)pyrazolo[1,5-a][1,3,5]triazin-4-amine (0.5 mmol) in 1 mL of isopropanol, was added 2-isopropoxy-5-methyl-4-(1-methylpiperidin-4-yl)aniline (0.5 mmol) and 4-methylbenzenesulfonic acid (1 mmol). The suspension was stirred at 150° C. for 3 hours. After cooling at RT and work-up, the residue was purified using a preparative HPLC to afford N2-(2-isopropoxy-5-methyl-4-(1-methylpiperidin-4-yl)phenyl)-N4-(2-(isopropylsulfonyl)phenyl)pyrazolo[1,5-a][1,3,5]triazine-2,4-diamine. 1H NMR (MeOD, 400 MHz) δ 8.51-8.54 (d, 1H), 7.94-8.04 (m, 2H), 7.35-7.47 (m, 3H), 6.90 (s, 1H), 6.34-6.35 (d, 1H), 4.54-4.60 (m. 1H), 3.82-3.85 (m, 2H), 3.23-3.30 (m, 1H), 2.91-3.01 (m, 6H), 2.25-2.33 (m, 5H), 2.03-2.06 (m, 2H), 1.33-1.35 (d, 6H), 1.26-1.28 (d, 6H); MS (ES+); 578.28 (M+1)+.

Workup

temperatureAfter cooling at RT
customthe residue was purified

Sources & evidence

ORD record: ord-66f1dd02992f47f0b2211c25edb70fbe
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08518931B2

Reaction notes

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