Trifluoroacetic acid → HCID 71522964, compound

HRID 1411232Notes

Reaction equation

HRID 1411232 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11]3)[CH2:9][N:8]([C:22](=[O:30])[NH:23][C:24]3[S:25][C:26]([Cl:29])=[CH:27][N:28]=3)[C:5]2=[CH:6][CH:7]=1.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][CH2:13][NH:12][CH2:11]3)[CH2:9][N:8]([C:22]([NH:23][C:24]3[S:25][C:26]([Cl:29])=[CH:27][N:28]=3)=[O:30])[C:5]2=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 71522963t-Butyl 5-bromo-1-((5-chlorothiazol-2-yl)carbamoyl)spiro[indoline-3,3'-pyrrolidine]-1'-carboxylate

Product 1

HCID 71522964HCID 71522964, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The t-butyl 5-bromo-1-((5-chlorothiazol-2-yl)carbamoyl)spiro[indoline-3,3′-pyrrolidine]-1′-carboxylate (54.2 mg, 0.105 mmol) obtained in Example 1 was dissolved in methylene chloride (0.5 mL). Thereafter, trifluoroacetic acid (0.5 mL) was added to the above obtained solution at room temperature, and the obtained mixture was then stirred for 1 hour. The reaction solution was neutralized with a saturated aqueous solution of sodium hydrogen carbonate, and a solid was then collected by filtration, followed by drying, to obtain the captioned compound (43.2 mg, 100%) in the form of a white solid.

Workup

  1. filtrationa solid was then collected by filtration
  2. customby drying

Sources & evidence

ORD record
ord-a69fccf7b2954f10b796f8217c9edf86
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

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