Hydrochloric Acid → 1-(4-methanesulfonyl-phenyl)-4-(piperidin-4-yloxy)-1H-pyrazolo[3,4-d]pyrimidine

HRID 719451Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[N:20]=[CH:19][N:18]=[C:17]3[N:21]([C:24]4[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][CH:25]=4)[N:22]=[CH:23][C:16]=23)[CH2:10][CH2:9]1)=O)(C)(C)C.C(#N)C.ClCCl.Cl>O1CCOCC1>[CH3:33][S:30]([C:27]1[CH:28]=[CH:29][C:24]([N:21]2[C:17]3=[N:18][CH:19]=[N:20][C:15]([O:14][CH:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)=[C:16]3[CH:23]=[N:22]2)=[CH:25][CH:26]=1)(=[O:31])=[O:32]

Participants

Conditions

Temperature: 40 °C

Procedure

Into a 200 mL round-bottomed flask was placed a stir bar, Compound A1 (1.2 g), anhydrous acetonitrile (50 mL), and dichloromethane (15 mL). 4M HCl in 1,4-dioxane (15 mL) was added under nitrogen and the mixture was stirred at 40° C. for 10 minutes. The solution turned cloudy. The precipitate was isolated and purified by HPLC to give Compound A6. 1H NMR (DMSO-d6, 400 MHz) δ 2.04 (m, 2H), 2.25 (m, 2H), 3.21 (m, 2H), 3.28 (s, 3H), 3.32 (m, 2H), 5.60 (m, 1H), 8.16 (d, 2H), 8.61 (d, 2H), 8.70 (s, 1H), 8.79 (s, 1H). LCMS: calculated for C17H19N5O3S 373.12, observed 374.1 (MH+).

Workup

customInto a 200 mL round-bottomed flask was placed
customThe precipitate was isolated
custompurified by HPLC

Sources & evidence

ORD record: ord-d4d9e4fe397a457aa854d3aa75607b8d
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07132426B2

Reaction notes

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