Hydrochloric Acid → HCID 118890620, compound

HRID 919554Notes

Reaction equation

HRID 919554 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 123872063HCID 123872063, compound

Product 1

HCID 118890620HCID 118890620, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of compound (S)-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., was added a solution of HCl in dioxane (10 mL) until the pH was acidic at 0° C. and stirred for 30 min at the same temperature. The reaction mixture was concentrated in vacuo to give a residue that was triturated with ether to give (S)—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 resin was added 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 intermediate (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 in vacuo
  3. customto give a residue that
  4. customwas triturated with ether

Sources & evidence

ORD record
ord-bc5a5763ac0f4210bb97e64fd6e3118f
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

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