Hydrochloric Acid → HCID 57893693, compound

HRID 1822045Notes

Reaction equation

HRID 1822045 reaction equation
Cl.C(OC([N:9]1[CH2:14][CH2:13][C@H:12]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][C:23](=[O:32])[C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=3[Cl:31])[N:17]=2)[CH2:11][C@@H:10]1[CH3:33])=O)(C)(C)C>O1CCOCC1>[Cl:31][C:25]1[CH:26]=[C:27]([F:30])[CH:28]=[CH:29][C:24]=1[C:23]([NH:22][C:18]1[CH:19]=[CH:20][CH:21]=[C:16]([O:15][C@H:12]2[CH2:13][CH2:14][NH:9][C@@H:10]([CH3:33])[CH2:11]2)[N:17]=1)=[O:32]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57893578HCID 57893578, compound

Product 1

HCID 57893693HCID 57893693, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Add 1 mL of conc. hydrochloric acid into a solution of 4-[6-(2-chloro-4-fluoro-benzoylamino)-pyridin-2-yloxy]-cis-2-methyl-piperidine-1-carboxylic acid tert-butyl ester isomer 2 (preparation 109, 0.678 g) in 1,4-dioxane 20 mL and heat at 100° C. After 40 min., partition between ethyl acetate and saturated aqueous NaCl, dry over anhydrous sodium sulfate, evaporate and purify on a silica gel column eluting with dichloromethane-2M NH3 in methanol, gradient to give the title compound (0.53 g). Mass spectrum (electric spray) m/z=364 (M+1); 1H NMR (CDCl3): 8.53 (br s, 1H), 7.84 (br d, 1H), 7.73 (dd, 1H), 7.63 (dd, 1H), 7.21 (dd, 1H), 7.10 (ddd, 1H), 6.49 (dd, 1H), 4.93 (m, 1H), 3.14 (m, 1H), 2.78 (m, 2H), 2.12 (m, 2H), 1.75 (br, 1H), 1.48 (m, 1H), 1.19 (m, 1H), 1.12 (d, 3H).

Workup

  1. custompartition between ethyl acetate and saturated aqueous NaCl
  2. dry with materialdry over anhydrous sodium sulfate
  3. customevaporate
  4. custompurify on a silica gel column
  5. washeluting with dichloromethane-2M NH3 in methanol, gradient

Sources & evidence

ORD record
ord-15633634ec05466d97c3ee596b6ef753
Source dataset
uspto-grants-2009_10
Patent number
US07608629B2

Reaction notes

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