Hydrochloric Acid → HCID 22347338, compound

HRID 432250Notes

Reaction equation

HRID 432250 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:26]3[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27]3)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17]C(OC(C)(C)C)=O)=[C:13]([F:25])[CH:12]=3)[C:3]=12.Cl.C(=O)([O-])[O-].[Na+].[Na+]>CC(C)=O>[NH2:17][C:14]1[CH:15]=[CH:16][C:11]([C:10]2[C:3]3[C:4](=[N:5][CH:6]=[N:7][C:2]=3[NH2:1])[N:8]([CH:26]3[CH2:27][CH2:28][NH:29][CH2:30][CH2:31]3)[N:9]=2)=[CH:12][C:13]=1[F:25]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 22346715HCID 22346715, compound

Product 1

HCID 22347338HCID 22347338, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of tert-butyl 4-(4-amino-3-{4-[(tert-butoxycarbonyl)amino]-3-fluorophenyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-piperidinecarboxylate (6.26 g, 11.9 mmol), 5M HCl (95 mL) and acetone (390 mL) was stirred at ambient temperature for 16 h. The reaction was basified with sodium carbonate and concentrated under reduced pressure. The residues were partitioned between CH2Cl2 (200 mL) and water (200 mL) and the aqueous phase was extracted with additional CH2Cl2 (2×200 mL). The combined organic layers were dried over anhydrous sodium sulfate and evaporated to dryness to afford 3-(4-amino-3-fluorophenyl)-1-(4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (3.427 g, 88%); 1H NMR (DMSO-d6, 400 MHz) δ 1.85 (2H, br t), 2.06 (2H, m), 2.65 (2H, m), 3.10 (2H, m), 4.72 (1H, m), 5.45 (2H, br s), 6.89 (1H, m), 7.22 (2H, m) and 8.19 (1H, s).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residues were partitioned between CH2Cl2 (200 mL) and water (200 mL)
  3. extractionthe aqueous phase was extracted with additional CH2Cl2 (2×200 mL)
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-644f17bcb24b45fca48c858139cf7cd7
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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