Hydrochloric Acid → HCID 22347338, compound

HRID 897540Notes

Reaction equation

HRID 897540 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-d4237c926f6548fba9d94fb6f720e617
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

Loading…