Acetyl chloride → HCID 117643681, compound

HRID 2171282Notes

Reaction equation

HRID 2171282 reaction equation
C(=O)([O-])O.[Na+].[C:6](Cl)(=[O:8])[CH3:7].C1COCC1.O.[O:16]=[C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19](=[O:26])[N:18]1[CH:27]1[CH:32]([NH:33][C:34]2[C:41]([F:42])=[CH:40][C:37]([C:38]#[N:39])=[C:36]([NH:43][C:44]3[CH:45]=[N:46][CH:47]=[C:48]([CH3:50])[CH:49]=3)[N:35]=2)[CH2:31][CH2:30][NH:29][CH2:28]1>C(OCC)(=O)C>[C:6]([N:29]1[CH2:30][CH2:31][CH:32]([NH:33][C:34]2[C:41]([F:42])=[CH:40][C:37]([C:38]#[N:39])=[C:36]([NH:43][C:44]3[CH:45]=[N:46][CH:47]=[C:48]([CH3:50])[CH:49]=3)[N:35]=2)[CH:27]([N:18]2[C:19](=[O:26])[C:20]3[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:17]2=[O:16])[CH2:28]1)(=[O:8])[CH3:7]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 21881883Oxolane--water (1/1)HCID 117643826HCID 117643826, compound

Product 1

HCID 117643681HCID 117643681, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydrogen carbonate (13 mg) and acetyl chloride (0.005 ml) were added to a THF/water (0.5 ml/0.5 ml) solution containing 6-((3-(1,3-dioxoisoindolin-2-yl)piperidin-4-yl)amino)-5-fluoro-2-((5-methylpyridin-3-yl)amino)nicotinonitrile (15 mg) obtained in the 2nd step under ice cooling, followed, by stirring at room temperature for 0.5 hours. Ethyl acetate was added to the reaction solution. The obtained organic layers were washed with saturated saline and dried over anhydrous sodium sulfate. Then, the solvent was distilled away under reduced pressure. Yellow oily matter of 6-((1-acetyl-3-(1,3-dioxoisoindolin-2-yl)piperidin-4-yl)amino)-5-fluoro-2-((5-methylpyridin-3-yl)amino)nicotinonitrile (12 mg) was thus obtained.

Workup

  1. customobtained in the 2nd step under ice cooling
  2. washThe obtained organic layers were washed with saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThen, the solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-71ed285309144c6cb4a6e02f91d37ccd
Source dataset
uspto-grants-2015_06
Patent number
US09051310B2

Reaction notes

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