Hydrochloric Acid → HCID 136350297, compound

HRID 1506468Notes

Reaction equation

HRID 1506468 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:7](=[C:19]([C:22]4[O:26][N:25]=[C:24]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)[C:23]=4[C:33]([F:36])([F:35])[F:34])[O:20][N:21]=3)[CH2:8][N:9](C(OC(C)(C)C)=O)[C:10]=2[CH:11]=1.Cl>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:7](=[C:19]([C:22]4[O:26][N:25]=[C:24]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)[C:23]=4[C:33]([F:36])([F:34])[F:35])[O:20][N:21]=3)[CH2:8][NH:9][C:10]=2[CH:11]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67167280HCID 67167280, compound

Product 1

HCID 136350297HCID 136350297, compoundYield 101.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of tert-butyl 7-bromo-3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)isoxazolo[4,3-c]quinoline-5(4H)-carboxylate (Preparation 77C, 0.030 g, 0.053 mmol) and 6 N aqueous hydrochloric acid (0.107 mL, 0.640 mmol) in THF (5.0 mL) was stirred at room temperature overnight. The reaction mixture was concentrated, dissolved in dichloromethane (3 mL) and treated with TFA (0.5 mL) for 2 h. The reaction mixture was concentrated under vacuum, dissolved in 5 ml dichloromethane and carefully neutralized with 1N NaOH to approx. pH=7, filtered and the filtrate concentrated to give 7-bromo-3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,5-dihydroisoxazolo[4,3-c]quinoline (0.025 g, 0.054 mmol, 100%) as a yellowish solid. The product had an HPLC ret. time=4.43 min. (condition B). LC/MS M+1=463.4 and 465.2.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutiondissolved in dichloromethane (3 mL)
  3. additiontreated with TFA (0.5 mL) for 2 h
  4. concentrationThe reaction mixture was concentrated under vacuum
  5. dissolutiondissolved in 5 ml dichloromethane
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-5eb8c7c7001642dbbc63cdd3361abd62
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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