Trifluoroacetic acid → 9'-(Trifluoromethyl)-spiro[piperidine-4,6'-pyrido[2,3-b]pyrrolo[1,2-d][1,4]oxazine]

HRID 2204086Notes

Reaction equation

HRID 2204086 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[N:7]2[C:8]3[CH:27]=[CH:26][CH:25]=[N:24][C:9]=3[O:10][C:11]3([CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]3)[C:6]2=[CH:5][CH:4]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:28][C:2]([F:1])([F:29])[C:3]1[N:7]2[C:8]3[CH:27]=[CH:26][CH:25]=[N:24][C:9]=3[O:10][C:11]3([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[C:6]2=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67465074Tert-butyl 9'-(trifluoromethyl)spiro-[piperidine-4,6'-pyrido[2,3-b]pyrrolo[1,2-d][1,4]oxazine]-1-carboxylate

Product 1

HCID 674655859'-(Trifluoromethyl)-spiro[piperidine-4,6'-pyrido[2,3-b]pyrrolo[1,2-d][1,4]oxazine]Yield 95.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 9′-(trifluoromethyl)spiro[piperidine-4,6′-pyrido[2,3-b]pyrrolo[1,2-d][1,4]oxazine]-1-carboxylate (83 mg, 0.20 mmol) in CH2Cl2 (3 mL) was added TFA (1.0 mL, 13 mmol) and the mixture was stirred at room temperature for 15 min before being evaporated to dryness. The residue was taken up in EtOAc and sat. aq. Na2CO3, the layers were separated, and aqueous layer was extracted with EtOAc (2×). The organics were combined, washed with sat. aq. Na2CO3, brine, dried (Na2SO4) and evaporated to dryness to give 9′-(trifluoromethyl)-spiro[piperidine-4,6′-pyrido[2,3-b]pyrrolo[1,2-d][1,4]oxazine] as a pale yellow solid (59 mg). ESI-MS m/z calc. 309.1, found 310.3 (M+1)+; Retention time: 1.32 minutes (3 min run).

Workup

  1. custombefore being evaporated to dryness
  2. customsat. aq. Na2CO3, the layers were separated
  3. extractionaqueous layer was extracted with EtOAc (2×)
  4. washwashed with sat. aq. Na2CO3, brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-e3e65894f1dc4819ba7c88b889390105
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

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