HCID 69158465, compound → HCID 22293677, compound

HRID 967387Notes

Reaction equation

HRID 967387 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:19]3[CH:20]=[C:21]([Cl:24])[CH:22]=[CH:23][C:18]=3[O:17][CH2:16][C:15]2=[O:25])[CH2:10][CH2:9]1)=O)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]2[O:17][CH2:16][C:15](=[O:25])[N:14]([CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[C:19]=2[CH:20]=1

Participants

3

Reactant 1

HCID 69158465HCID 69158465, compound

Product 1

HCID 22293677HCID 22293677, compoundYield 137.7%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

4-(6-Chloro-3-oxo-2,3-dihydro-benzo[1,4]oxazin-4-yl)-piperidine-1-carboxylic acid tert-butyl ester (7.2 g, 19.6 mmol) was set stirring and a 1:1 TFA/CH2Cl2 solvent mixture was added. After 1 h the mixture was evaporated under reduced pressure and the resulting red oil brought up in Et2O. A solid formed and was filtered and air dried to give 7.2 g (96%) of a light beige solid. MS (electrospray): exact mass calculated for C13H15ClN2O2, 266.08. m/z found, 267.1 [M+H]+. 1H NMR (400 MHz, CD3OD): 7.52 (s, 1H), 7.20-7.00 (m, 2H), 4.60 (s, 2H), 4.50-4.40 (m, 1H), 3.65-3.55 (m, 2H), 3.28 (t, J=13.1 Hz, 2H), 3.10-3.00 (m, 2H), 2.15 (d, J=13.9 Hz, 2H).

Workup

  1. customAfter 1 h the mixture was evaporated under reduced pressure
  2. customA solid formed
  3. filtrationwas filtered
  4. customair dried

Sources & evidence

ORD record
ord-57eb7d2b5ba746b585890bb18e9a361e
Source dataset
uspto-grants-2005_10
Patent number
US06953793B2

Reaction notes

Loading…