Hydrochloric Acid → HCID 178461058, compound

HRID 1943874Notes

Reaction equation

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

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 312751,4-Dioxane

HCID 178461060HCID 178461060, compound

Product 1

HCID 178461058HCID 178461058, compoundYield 83%

Procedure

tert-Butyl 4-(5-(2,6-difluoro-3-(propylsulfonamido)benzamido)-1H-pyrazolo[3,4-b]pyridin-3-yl)piperidine-1-carboxylate (7 mg, 0.01 mmol) was treated with a 0.5M solution of HCl in dioxane (0.5 mL, 2 mmol) at room temperature for 1 hour. The volatiles were removed in vacuo to afford 2,6-difluoro-N-(3-(piperidin-4-yl)-1H-pyrazolo[3,4-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide hydrochloride as a solid (5 mg, 83%). 1H NMR (400 MHz, CD3OD) δ 8.87-8.90 (m, 1H), 8.62-8.58 (m, 1H), 7.70-7.64 (m, 1H), 7.18-7.13 (m, 1H), 3.76-3.52 (m, 3H), 3.33-3.22 (m, 2H), 3.15-3.11 (m, 2H), 2.38-2.30 (m, 2H), 2.25-2.13 (m, 2H), 1.93-1.83 (m, 2H), 1.06 (t, J=7.4 Hz, 3H). m/z (APCI-pos) M+1=479.2.

Workup

customThe volatiles were removed in vacuo

Sources & evidence

ORD record: ord-9cb6846d29ba490c9ec945ed82adf7ac
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394795B2

Reaction notes

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