Trifluoroacetic acid → HCID 9862729, compound

HRID 427269Notes

Reaction equation

HRID 427269 reaction equation
C(OC([N:8]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[O:11][CH:10]([CH2:18][NH:19][CH2:20][CH2:21][CH2:22][C:23]2[C:31]3[C:26](=[CH:27][CH:28]=[C:29]([F:32])[CH:30]=3)[NH:25][CH:24]=2)[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[O:11]1[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH:8][CH2:9][CH:10]1[CH2:18][NH:19][CH2:20][CH2:21][CH2:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([F:32])[CH:30]=2)[NH:25][CH:24]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 53929073HCID 53929073, compound

Product 1

HCID 9862729HCID 9862729, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared in a 19% yield by reacting {[3-(5-fluoro-1H-indol-3-yl)-propylamino]-methyl}-3,4-dihydro-benzo [1,4]oxazine-4-carboxylic acid tert-butyl ester (0.49 g, 1.1 mmol) with trifluoroacetic acid (20 mL) in methylene chloride (20 mL). The reaction mixture was stirred at room temperature for two hours and then poured into saturated sodium carbonate and extracted with methylene chlloride. The organic layer was dried over anhydrous sodium sulfate, filtered and chromatographed (5% MeOH in methylene chloride) afforded 0.06 g (19%) of product as an oil. The oxalate salt was prepared in ethanol: mp 168-170° C.

Workup

  1. extractionextracted with methylene chlloride
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customchromatographed (5% MeOH in methylene chloride)

Sources & evidence

ORD record
ord-73806b6692004373aff45d63e2811c53
Source dataset
uspto-grants-2001_11
Patent number
US06313114B1

Reaction notes

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