Hydrochloric Acid → HCID 178478976, compound

HRID 387527Notes

Reaction equation

HRID 387527 reaction equation
[CH:1]1([C:4]2[C:5]([N:14]3[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]3)=[C:6]3[C:12]([I:13])=[N:11][NH:10][C:7]3=[N:8][CH:9]=2)[CH2:3][CH2:2]1.[ClH:27]>O1CCOCC1>[ClH:27].[CH:1]1([C:4]2[C:5]([N:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)=[C:6]3[C:12]([I:13])=[N:11][NH:10][C:7]3=[N:8][CH:9]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178452207HCID 178452207, compound

Product 1

HCID 178478976HCID 178478976, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of tert-butyl 4-(5-cyclopropyl-3-iodo-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (200 mg, 0.426 mmol) and 4N HCl in dioxane (4 mL) was stirred at room temperature for 2 hours. The solvent was then removed in vacuo, and the residue was triturated with CH3CN. The solid formed was filtered, washed with Et2O and dried to provide 5-cyclopropyl-3-iodo-4-(piperazin-1-yl)-1H-pyrazolo[3,4-b]pyridine hydrochloride salt (179 mg, 95% yield) as a solid. 1H NMR (400 MHz, d6-DMSO) δ 9.47 (br s, 2H), 8.32 (s, 1H), 3.67-3.62 (m, 4H), 3.42-3.35 (m, 4H), 2.09-2.03 (m, 1H), 1.07-1.01 (m, 2H), 0.80-0.76 (m, 2H); LCMS (APCI+) m/z 370 (M+H)+, Retention time=1.87 minutes.

Workup

  1. customThe solvent was then removed in vacuo
  2. customthe residue was triturated with CH3CN
  3. customThe solid formed
  4. filtrationwas filtered
  5. washwashed with Et2O
  6. customdried

Sources & evidence

ORD record
ord-11dd3864d064455cbf4597a101d2a46f
Source dataset
uspto-grants-2013_02
Patent number
US08372842B2

Reaction notes

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