Hydrochloric Acid → N5-(2-isopropoxy-5-methyl-4-(piperidin-4-yl)phenyl)-N7-(2-(isopropylsulfonyl)phenyl)pyrazolo[1,5-a]pyrimidine-5,7-diamine

HRID 1896087Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15]([CH:18]([CH3:20])[CH3:19])(=[O:17])=[O:16])[N:5]2[N:21]=[CH:22][CH:23]=[C:4]2[N:3]=1.[CH:24]([O:27][C:28]1[CH:34]=[C:33]([CH:35]2[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)[C:32]([CH3:41])=[CH:31][C:29]=1[NH2:30])([CH3:26])[CH3:25].Cl>C(O)(C)C.O1CCOCC1>[CH:24]([O:27][C:28]1[CH:34]=[C:33]([CH:35]2[CH2:36][CH2:37][NH:38][CH2:39][CH2:40]2)[C:32]([CH3:41])=[CH:31][C:29]=1[NH:30][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15]([CH:18]([CH3:20])[CH3:19])(=[O:17])=[O:16])[N:5]2[N:21]=[CH:22][CH:23]=[C:4]2[N:3]=1)([CH3:26])[CH3:25]

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of 5-chloro-N-(2-(isopropylsulfonyl)phenyl)pyrazolo[1,5-a]pyrimidin-7-amine (0.1 mmol) and 2-isopropoxy-5-methyl-4-(piperidin-4-yl)aniline (0.1 mmol) in 2 mL of isopropanol, was added 25 uL of HCl in dioxane (2 N). The suspension was stirred at 150° C. for 3 hours. After work-up and prep-HPLC, product was obtained. 1H NMR (CDCl3, 400 MHz) δ 7.88-7.95 (m, 3H), 7.73-7.75 (d, 1H), 7.61-7.64 (m, 1H), 7.23-7.26 (m, 1H), 6.88 (s, 1H), 6.75 (s, 1H), 6.17-6.18 (d, 1H), 6.09 (s, 1H), 4.46-4.54 (m. 1H), 3.30-3.34 (m, 2H), 3.12-3.21 (m, 1H), 2.79-2.83 (m, 3H), 2.27 (s, 3H), 1.77-1.79 (m, 4H), 1.15-1.28 (m, 12H); MS (ES+): 563.28 (M+1)+.

Workup

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

Sources & evidence

ORD record: ord-ecb99b3c3798488d997bd1edc40f512f
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08518931B2

Reaction notes

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