Trifluoroacetic acid → HCID 68006072, compound

HRID 1026534Notes

Reaction equation

HRID 1026534 reaction equation
C([O:5][C:6]([C:8]1([O:11][C:12]2[C:17]([NH:18][CH:19]3[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]3)=[CH:16][C:15]([Cl:32])=[CH:14][N:13]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[F:33][C:34]([F:39])([F:38])[C:35]([OH:37])=[O:36]>>[F:33][C:34]([F:39])([F:38])[C:35]([OH:37])=[O:36].[Cl:32][C:15]1[CH:14]=[N:13][C:12]2[O:11][C:8]3([CH2:10][CH2:9]3)[C:6](=[O:5])[N:18]([CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[C:17]=2[CH:16]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68006128HCID 68006128, compound

Product 1

HCID 68006072HCID 68006072, compound

Procedure

A trifluoroacetic acid solution (70 ml) of tert-butyl 4-[(2-{[1-(tert-butoxycarbonyl)cyclopropyl]oxy}-5-chloropyridin-3-yl)amino]piperidine-1-carboxylate (7.09 g) was stirred at 70° C. for 28 hours. The temperature was brought back to room temperature, followed by concentration under reduced pressure, and toluene was further added and concentrated under reduced pressure. After ether was added to the residue, the suspension was stirred for 2 hours, and then the insolubles were collected by filtration to afford 7′-chloro-1′-piperidin-4-ylspiro[cyclopropane-1,3′-pyrido[2,3-b][1,4]oxazine]-2′(1′H)-one trifluoroacetate (5.37 g).

Workup

  1. customwas brought back to room temperature
  2. concentrationfollowed by concentration under reduced pressure, and toluene
  3. additionwas further added
  4. concentrationconcentrated under reduced pressure
  5. additionAfter ether was added to the residue
  6. filtrationthe insolubles were collected by filtration

Sources & evidence

ORD record
ord-c05ad4a5b6ff40658272beda9337cedf
Source dataset
uspto-grants-2014_05
Patent number
US08729095B2

Reaction notes

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