Pyridine → tert-butyl {[1-[(5-cyano-2-furyl)sulfonyl]-4-fluoro-5-(2-fluoropyridin-3-yl)-1H-pyrrol-3-yl]methyl}methylcarbamate

HRID 1426739Notes

Reaction equation

HRID 1426739 reaction equation
[NH2:1][C:2]([C:4]1[O:8][C:7]([S:9]([N:12]2[C:16]([C:17]3[C:18]([F:23])=[N:19][CH:20]=[CH:21][CH:22]=3)=[C:15]([F:24])[C:14]([CH2:25][N:26]([CH3:34])[C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:13]2)(=[O:11])=[O:10])=[CH:6][CH:5]=1)=O.N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>O1CCCC1>[C:2]([C:4]1[O:8][C:7]([S:9]([N:12]2[C:16]([C:17]3[C:18]([F:23])=[N:19][CH:20]=[CH:21][CH:22]=3)=[C:15]([F:24])[C:14]([CH2:25][N:26]([CH3:34])[C:27](=[O:33])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[CH:13]2)(=[O:11])=[O:10])=[CH:6][CH:5]=1)#[N:1]

Participants

5

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 67396181tert-butyl {[1-{[5-(aminocarbonyl)-2-furyl]sulfonyl}-4-fluoro-5-(2-fluoropyridin-3-yl)-1H-pyrrol-3-yl]methyl}methylcarbamate

Product 1

HCID 67397187tert-butyl {[1-[(5-cyano-2-furyl)sulfonyl]-4-fluoro-5-(2-fluoropyridin-3-yl)-1H-pyrrol-3-yl]methyl}methylcarbamateYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl {[1-{[5-(aminocarbonyl)-2-furyl]sulfonyl}-4-fluoro-5-(2-fluoropyridin-3-yl)-1H-pyrrol-3-yl]methyl}methylcarbamate (285 mg) in tetrahydrofuran (2.5 mL) were added pyridine (181 mg) and trifluoroacetic anhydride (211 mg) under ice-cooling, and the mixture was stirred for 2 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica-gel column chromatography (eluent: hexane-ethyl acetate=6:1→3:2) to give the title compound as a pale-yellow oil (yield 258 mg, 94%).

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica-gel column chromatography (eluent: hexane-ethyl acetate=6:1→3:2)

Sources & evidence

ORD record
ord-a1c2c5ef3bc44cea936881e19a19e0f1
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

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