Hydrochloric Acid → HCID 131734883, compound

HRID 919559Notes

Reaction equation

HRID 919559 reaction equation
C[Si](C)(C)CCOC[N:7]1[C:11]2=[N:12][CH:13]=[N:14][C:15]([NH:16][C@@H:17]3[CH2:22][CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18]3)=[C:10]2[CH:9]=[N:8]1.[ClH:32]>O1CCOCC1>[ClH:32].[NH:19]1[CH2:20][CH2:21][CH2:22][C@@H:17]([NH:16][C:15]2[N:14]=[CH:13][N:12]=[C:11]3[NH:7][N:8]=[CH:9][C:10]=23)[CH2:18]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 123836724HCID 123836724, compound

Product 1

HCID 131734883HCID 131734883, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of compound (R)-tert-butyl 3-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)piperidine-1-carboxylate (1 g, 2.22 mmol) in dioxane (10 mL) at 0° C., a solution of HCl in dioxane (10 mL) was added until the pH was acidic at 0° C. and stirred for 30 min, at the same temperature. The reaction mixture was concentrated to give a residue that was triturated with ether to give (R)—N-(piperidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine hydrochloride as a free flowing solid. Then the compound was dissolved in MeOH, and to the reaction mixture was added a carbonate polymer support resin until the mixture turns basic (Checked by pH paper). The reaction mixture was filtered and the filtrate was concentrated in vacuo to yield the titled compound (350 mg, 72%). 1H NMR (400 MHz, DMSO-d6): δ 13.1 (bs, 1H), 8.28 (s, 1H), 8.23 (s, 1H), 4.46 (bs, 2H), 3.36-3.34 (m, 2H), 3.16-3.08 (m, 1H), 2.99-2.86 (m, 2H), 2.50 (bs, 1H), 1.97-1.81 (m, 2H), 1.68-1.58 (m, 2H). LC-MS: m/z [M+1]=219.

Workup

  1. customwas acidic at 0° C.
  2. concentrationThe reaction mixture was concentrated
  3. customto give a residue that
  4. customwas triturated with ether

Sources & evidence

ORD record
ord-6812edf947e34dde9729aeeed4fefbf0
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

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