p-Toluenesulfonic acid → HCID 25160548, compound

HRID 2046970Notes

Reaction equation

HRID 2046970 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]=[C:18](S(C)(=O)=O)[N:17]=[C:16]2[NH:24][N:25]=[CH:26][C:15]=12)(=[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][NH:41][CH2:40][CH2:39]2)[C:35]([CH3:44])=[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][NH:41][CH2:42][CH2:43]2)[C:35]([CH3:44])=[CH:34][C:32]=1[NH:33][C:18]1[N:17]=[C:16]2[NH:24][N:25]=[CH:26][C:15]2=[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]=1)([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 58290851N-(2-(isopropylsulfonyl)phenyl)-6-(methylsulfonyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amineHCID 582908952-Isopropoxy-5-methyl-4-(piperidin-4-yl)aniline

Product 1

HCID 25160548HCID 25160548, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
150 °C

Procedure

To a suspension of N-(2-(isopropylsulfonyl)phenyl)-6-(methylsulfonyl)-1H-pyrazolo[3,4-d]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 prep-HPLC, the final product was obtained. 1H NMR (CDCl3, 400 MHz) δ 8.74-8.77 (d, 1H), 8.24 (s, 1H), 7.92-7.96 (m, 2H), 7.65-7.70 (m, 1H), 7.27-7.33(m, 1H), 6.85(s, 1H), 4.60-4.67 (m. 1H), 3.71-3.74 (m, 2H), 3.25-3.32 (m, 1H), 2.78-2.97(m, 6H), 2.28-2.33 (m, 5H), 1.95-1.98 (m, 2H), 1.39-1.41(d, 6H), 1.33-1.35 (d, 6H); MS (ES+): 578.28 (M+1)+.

Sources & evidence

ORD record
ord-52dc62911a0a48f28e90aecd165e4000
Source dataset
uspto-grants-2013_11
Patent number
US08592432B2

Reaction notes

Loading…