Trifluoroacetic acid → HCID 22293849, compound

HRID 967396Notes

Reaction equation

HRID 967396 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:19](=[O:20])[CH2:18][O:17][C:16]3[CH:21]=[CH:22][CH:23]=[N:24][C:15]2=3)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:8]1[CH2:9][CH2:10][CH:11]([N:14]2[C:19](=[O:20])[CH2:18][O:17][C:16]3[CH:21]=[CH:22][CH:23]=[N:24][C:15]2=3)[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59774562HCID 59774562, compound

Product 1

HCID 22293849HCID 22293849, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 0.37 g (0.0011 mol) of 4-(3-oxo-2,3-dihydro-pyrido[3,2-b][1,4]oxazin-4-yl)-piperidine-1-carboxylic acid tert-butyl ester in CH2Cl2 (2.5 mL) was added 2.5 mL of TFA. After 2.5 h, the solvent was removed. The residue was partitioned between EtOAc (200 mL) and 1 N NaOH (150 mL). The aqueous layer was extracted with EtOAc (3×100 mL) and the combined organic layers were dried over Na2SO4, and concentrated to afford 0.24 g (94%) of a white/pink solid. 1H NMR (400 MHz, CDCl3): 7.87 (dd, J=4.8 Hz, 1.5 Hz, 1H), 7.25 (dd, J=7.8 Hz, 1.8 Hz, 1H), 6.84 (dd, J=7.8 Hz, 4.8 Hz, 1H), 4.98-4.83 (m, 1H), 4.45 (s, 2H), 3.90 (s, 1H), 3.06 (d, J=8.3 Hz, 2H), 2.65-2.53 (m, 4H), 1.65-1.53 (m, 2H).

Workup

  1. customthe solvent was removed
  2. customThe residue was partitioned between EtOAc (200 mL) and 1 N NaOH (150 mL)
  3. extractionThe aqueous layer was extracted with EtOAc (3×100 mL)
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cf66a3b93f944805b00907967d96352f
Source dataset
uspto-grants-2005_10
Patent number
US06953793B2

Reaction notes

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