Hydrochloric Acid → HCID 59085845, compound

HRID 397529Notes

Reaction equation

HRID 397529 reaction equation
[CH2:1]([O:3][C:4](=[O:33])[CH2:5][C:6]1[C:11]([Cl:12])=[CH:10][N:9]=[C:8]([N:13](C(OC(C)(C)C)=O)[CH2:14][C:15]([F:24])([F:23])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N+:17]=2[O-:22])[C:7]=1[F:32])[CH3:2].Cl.N#N>CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:33])[CH2:5][C:6]1[C:11]([Cl:12])=[CH:10][N:9]=[C:8]([NH:13][CH2:14][C:15]([F:23])([F:24])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N+:17]=2[O-:22])[C:7]=1[F:32])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 59085853HCID 59085853, compound

Product 1

HCID 59085845HCID 59085845, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 0.6 g (1.25 mmol) ethyl(2-{(tert-butoxycarbonyl)[2,2-difluoro-2-(1-oxido-2-pyridinyl)ethyl]amino}-5-chloro-3-fluoro-4-pyridinyl)acetate 1-7 in 20 mL EtOAc was passed a steady stream of HCl gas for 10 min, then the reaction mixture was allowed to stir at 0° C. for 1 hr. A stream of N2 gas was then passed through the mixture for 5 min, and the mixture poured into 200 mL EtOAc/50 mL 2M NaOH/7 mL conc NaOH and the layers mixed and separated. The aqueous, layer was back extracted with 50 mL EtOAc and the combined organic layers washed with 150 mL water, and brine, then dried over Na2SO4, filtered, concentrated, to give ethyl(5-chloro-2-{[2,2-difluoro-2-(1-oxido-2-pyridinyl)ethyl]amino}-3-fluoro-4-pyridinyl)acetate 1-8 which was used without further purification. 1H NMR (400 mHz, CDCl3) δ8.28 (br d, 1H, J=6.41 Hz); 7.81 (s, 1H); 7.62 (dd, 1H, J=8.06 and 2.20 Hz); 7.33 (m, 2H); 5.21 (br m, 1H); 4.68 (dt, 2H, J=13.9 and 6.59 Hz); 4.18 (q, 2H, J=6.96 Hz); 3.72 (d, 2H, J=1.47 Hz); 1.26 (t, 3H, J=7.14 Hz). Mass spectrum (electrospray) M+H=390.1

Workup

  1. customTo a 0° C.
  2. customfor 10 min
  3. additionthe layers mixed
  4. customseparated
  5. extractionThe aqueous, layer was back extracted with 50 mL EtOAc
  6. washthe combined organic layers washed with 150 mL water, and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-8cb44ccd02c241608695444b9ff9bd4c
Source dataset
uspto-grants-2003_08
Patent number
US06610701B2

Reaction notes

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