Hydrochloric Acid → HCID 58079827, compound

HRID 1961533Notes

Reaction equation

HRID 1961533 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:32]([F:35])([F:34])[F:33])[O:13][N:12]=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([C:20]4([F:31])[CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21]4)=[CH:16][CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl.C(Cl)Cl>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:32]([F:33])([F:35])[F:34])[O:13][N:12]=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([C:20]4([F:31])[CH2:23][NH:22][CH2:21]4)=[CH:16][CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 58079837HCID 58079837, compound

Product 1

HCID 58079827HCID 58079827, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of tert-butyl 3-(4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenyl)-3-fluoroazetidine-1-carboxylate (Preparation 14) in methanol (10 mL) was added a methanolic solution of HCl (10 mL of 1.25 M). Reaction mixture warmed to 65° C. for 1.5 hours. Reaction concentrated via rotavap to yield a viscuous oil. CH2Cl2 was added and a precipitate formed. Volatiles removed under reduced pressure to yield 573 mg of the title compound as a white solid. 1H NMR (DMSO-d6) δ 9.8-9.6 (br s, 2H) 7.9-7.8 (m, 3H), 7.75 (d, 2H), 7.63 (d, 2H), 4.64-4.29 (m, 6H)). LC/MS retention time=3.039 minutes, MS calculated for (C19H14Cl2F4N2O), 432.04; found 433.0 M+H.

Workup

  1. customReaction mixture
  2. customReaction
  3. concentrationconcentrated via rotavap
  4. customto yield a viscuous oil
  5. customa precipitate formed
  6. customVolatiles removed under reduced pressure

Sources & evidence

ORD record
ord-3c0e3efd41594eeca528ac2353348f38
Source dataset
uspto-grants-2013_04
Patent number
US08415310B2

Reaction notes

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