Trifluoroacetic acid → HCID 68093248, compound

HRID 1778374Notes

Reaction equation

HRID 1778374 reaction equation
C(O)(C(F)(F)F)=O.[F:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([N:18]([C:27]2[C:36]([C:37]([O:39][CH3:40])=[O:38])=[C:35]3[C:30]([C:31]4[CH:43]=[CH:42][O:41][C:32]=4[CH2:33][O:34]3)=[CH:29][CH:28]=2)COCC[Si](C)(C)C)(=[O:17])=[O:16])=[C:11](/[CH:44]=[CH:45]\[CH2:46][N:47]2[CH2:52][CH2:51][O:50][CH2:49][CH2:48]2)[CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[F:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:18][C:27]2[C:36]([C:37]([O:39][CH3:40])=[O:38])=[C:35]3[C:30]([C:31]4[CH:43]=[CH:42][O:41][C:32]=4[CH2:33][O:34]3)=[CH:29][CH:28]=2)(=[O:16])=[O:17])=[C:11](/[CH:44]=[CH:45]\[CH2:46][N:47]2[CH2:48][CH2:49][O:50][CH2:51][CH2:52]2)[CH:10]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 66685688HCID 66685688, compound2×

Product 1

HCID 68093248HCID 68093248, compoundYield 44.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (2 mL) was added to a solution of methyl 7-{N-[4-fluoro-2-((Z)-3-{morpholin-4-yl}prop-1-enyl)benzenesulfonyl]-N-(2-trimethylsilanylethoxymethyl)amino]-4H-furo[2,3-c]chromene-6-carboxylate (Intermediate 52, 1.15 g) in DCM (20 mL). The reaction mixture was stirred at room temperature for 30 minutes. Aqueous potassium carbonate was added and the layers were separated. The organic layer was dried (Na2SO4), filtered and the filtrate was concentrated in vacuo. The residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane, with a gradient of 20-80% to give methyl 7-{4-fluoro-2-[(Z)-3-(morpholin-4-yl)prop-1-enyl]benzenesulfonylamino}-4H-furo[2,3-c]chromene-6-carboxylate (0.412 g) as a yellow foam.

Workup

  1. customthe layers were separated
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was purified by chromatography on silica
  6. washeluting with a mixture of ethyl acetate and cyclohexane, with a gradient of 20-80%

Sources & evidence

ORD record
ord-26feba33735a426fb80ea4761e362374
Source dataset
uspto-grants-2016_02
Patent number
US09266896B2

Reaction notes

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