Ethyl Acetate → HCID 117667074, compound

HRID 1526238Notes

Reaction equation

HRID 1526238 reaction equation
[C:1]([C:4]1[C:5]([NH:13][C:14]2[CH:15]=[N:16][N:17]([CH:19]3[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]3)[CH:18]=2)=[N:6][C:7]([Cl:12])=[C:8]([CH2:10][CH3:11])[N:9]=1)(=[O:3])[NH2:2].C(OCC)(=O)C.C(OC(=O)C)C.Cl>C(O)C>[Cl:12][C:7]1[N:6]=[C:5]([NH:13][C:14]2[CH:15]=[N:16][N:17]([CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[CH:18]=2)[C:4]([C:1]([NH2:2])=[O:3])=[N:9][C:8]=1[CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 21866389Hydrogen chloride-ethyl acetateHCID 117667282HCID 117667282, compound

Product 1

HCID 117667074HCID 117667074, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of tert-butyl 4-{4-[(3-carbamoyl-6-chloro-5-ethylpyrazin-2-yl)amino]-1H-pyrazol-1-yl}piperidine-1-carboxylate (1.69 g), ethyl acetate (10 mL), and ethanol (10 mL) was added a 4 M hydrogen chloride ethyl acetate solution (20 mL), followed by stirring at room temperature for 2 hours. The mixture was subjected to liquid separation by the addition of a 1 M aqueous sodium hydroxide solution and chloroform. The organic phase was dried over anhydrous sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure to obtain 5-chloro-6-ethyl-3-{[1-(piperidin-4-yl)-1H-pyrazol-4-yl]amino}pyrazine-2-carboxamide (1.32 g) as a yellow solid.

Workup

  1. customThe mixture was subjected to liquid separation by the addition of a 1 M aqueous sodium hydroxide solution and chloroform
  2. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7d1d210cba1f43858fca0773c30b5c34
Source dataset
uspto-grants-2015_07
Patent number
US09085540B2

Reaction notes

Loading…