Ethyl Acetate → HCID 58513257, compound

HRID 1405058Notes

Reaction equation

HRID 1405058 reaction equation
Cl[C:2]1[C:7]([C:8]#[C:9][C:10]2[CH:11]=[N:12][C:13]([NH2:16])=[CH:14][CH:15]=2)=[C:6]([CH3:17])[N:5]=[C:4]([NH2:18])[N:3]=1.[C:19]([O:23][C:24](=[O:32])[NH:25][CH:26]1[CH2:31][CH2:30][CH2:29][NH:28][CH2:27]1)([CH3:22])([CH3:21])[CH3:20].C(OCC)(=O)C.C([O-])([O-])=O.[Na+].[Na+]>CN1C(=O)CCC1.CS(C)=O>[C:19]([O:23][C:24](=[O:32])[NH:25][CH:26]1[CH2:31][CH2:30][CH2:29][N:28]([C:2]2[C:7]([C:8]#[C:9][C:10]3[CH:11]=[N:12][C:13]([NH2:16])=[CH:14][CH:15]=3)=[C:6]([CH3:17])[N:5]=[C:4]([NH2:18])[N:3]=2)[CH2:27]1)([CH3:22])([CH3:20])[CH3:21]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 42330413-(Boc-amino)piperidineHCID 58513427HCID 58513427, compound

Product 1

HCID 58513257HCID 58513257, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The title compound is synthesized according to general procedure GP7 starting from 2.0 g (7.7 mmol) 4-chloro-6-methyl-5-(6-amino-pyridin-3-ylethynyl)-pyrimidin-2-ylamine and 2.0 g (10.0 mmol) piperidin-3-yl-carbamic acid tert-butyl ester using 1.29 mL (9.2 mmol) triethylamine in 5 mL NMP and 5 mL DMSO. 200 mL ethyl acetate and 100 mL half concentrated aqueous Na2CO3 solution are added and the phases are separated. The aqueous phase is extracted 2 times with ethyl acetate (100 mL each). The combined organic layers are dried over sodium sulfate and the solvent is removed under reduced pressure. The crude product is used without further purification in the next step.

Workup

  1. customthe phases are separated
  2. extractionThe aqueous phase is extracted 2 times with ethyl acetate (100 mL each)
  3. dry with materialThe combined organic layers are dried over sodium sulfate
  4. customthe solvent is removed under reduced pressure
  5. customThe crude product is used without further purification in the next step

Sources & evidence

ORD record
ord-46b5efd6d6bb4b7f8b21a6f7543afe81
Source dataset
uspto-grants-2014_12
Patent number
US08916548B2

Reaction notes

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