HCID 90003329, compound → HCID 123167069, compound

HRID 1778449Notes

Reaction equation

HRID 1778449 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([C@@H:25]3[CH2:30][CH2:29][CH2:28][N:27]([C:31](=[O:54])[C:32]([C:52]#[N:53])=[CH:33][C:34]([N:37]4[CH2:42][C@@H:41]([CH3:43])[N:40](C(OC(C)(C)C)=O)[C@@H:39]([CH3:51])[CH2:38]4)([CH3:36])[CH3:35])[CH2:26]3)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][C:12]=3[F:24])[C:3]=12>Cl.O1CCOCC1>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([C@@H:25]3[CH2:30][CH2:29][CH2:28][N:27]([C:31]([C:32](=[CH:33][C:34]([N:37]4[CH2:42][C@@H:41]([CH3:43])[NH:40][C@@H:39]([CH3:51])[CH2:38]4)([CH3:36])[CH3:35])[C:52]#[N:53])=[O:54])[CH2:26]3)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][C:12]=3[F:24])[C:3]=12

Participants

4

Reactant 1

HCID 90003329HCID 90003329, compound

Product 1

HCID 123167069HCID 123167069, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

The (2S,6R)-tert-butyl 4-(5-((R)-3-(4-amino-3-(2-fluoro-4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-yl)-4-cyano-2-methyl-5-oxopent-3-en-2-yl)-2,6-dimethylpiperazine-1-carboxylate (103.5 mg, 0.1400 mmol) was dissolved in 4N HCl in dioxane, and stirred at rt for 3 hours. The solvent was removed and 2 mL of MeOH was added to the residues. The mixture was neutralized to pH around 7-8 and extracted with DCM. The combined organic layer was washed with brine, dried over sodium sulfate, filtered, and the solvent evaporated to get pure product 2-((R)-3-(4-amino-3-(2-fluoro-4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carbonyl)-4-((3S,5R)-3,5-dimethylpiperazin-1-yl)-4-methylpent-2-enenitrile as a white solid. MS (pos. ion) m/z: 638 (M+1).

Workup

  1. customThe solvent was removed
  2. addition2 mL of MeOH was added to the residues
  3. extractionextracted with DCM
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-23187f1e98ae49d8abe5b059c849e7d6
Source dataset
uspto-grants-2016_02
Patent number
US09266895B2

Reaction notes

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