Hydrochloric Acid → HCID 57893710, compound

HRID 1822035Notes

Reaction equation

HRID 1822035 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])[CH: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)[CH:17]=1)=[O:32]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57893766HCID 57893766, compound

Product 1

HCID 57893710HCID 57893710, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Add 0.7 mL of conc. hydrochloric acid into a solution of 4-[3-(2-chloro-4-fluoro-benzoylamino)-phenoxy]-cis-2-methyl-piperidine-1-carboxylic acid tert-butyl ester isomer 2 (Preparation 86, 0.464 g) in 1,4-dioxane 20 mL and heat at 100° C. for 40 min. Partition between ethyl acetate and saturated aqueous NaCl, dry over anhydrous sodium sulfate, evaporate and purify on a silica gel column (10 g, solvent: dichloromethane-2M NH3 in methanol, gradient) to give the title compound (0.298 g). Mass spectrum (electrospray) m/z=363 (M+1); 1H NMR (CDCl3): 7.94 (br s, 1H), 7.77 (dd, 1H), 7.41 (t, 1H), 7.24 (t, 1H), 7.19 (dd, 1H), 7.08 (m, 2H), 6.72 (m, 1H), 4.29 (m, 1H), 3.46 (s, 3H), 3.17 (m, 1H), 2.73 (m, 2H), 2.14 (m, 2H), 1.69 (br, 1H), 1.51 (m, 1H), 1.22 (m, 1H), 1.14 (d, J=6.4 Hz, 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 (10 g, solvent: dichloromethane-2M NH3 in methanol, gradient)

Sources & evidence

ORD record
ord-051a045c29a9444a92ce69ea794553e3
Source dataset
uspto-grants-2009_10
Patent number
US07608629B2

Reaction notes

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