Trifluoroacetic acid → N-(4-(7-((1-isobutylazetidin-3-yl)ethynyl)-4-oxo-4H-chromen-3-yl)phenyl)methanesulfonamide

HRID 1188265Notes

Reaction equation

HRID 1188265 reaction equation
[NH:1]1[CH2:4][CH:3]([C:5]#[C:6][C:7]2[CH:16]=[C:15]3[C:10]([C:11](=[O:28])[C:12]([C:17]4[CH:22]=[CH:21][C:20]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[CH:19][CH:18]=4)=[CH:13][O:14]3)=[CH:9][CH:8]=2)[CH2:2]1.FC(F)(F)C(O)=O.[CH:36](=O)[CH:37]([CH3:39])[CH3:38].C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.O1CCCC1>[CH2:36]([N:1]1[CH2:4][CH:3]([C:5]#[C:6][C:7]2[CH:16]=[C:15]3[C:10]([C:11](=[O:28])[C:12]([C:17]4[CH:22]=[CH:21][C:20]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[CH:19][CH:18]=4)=[CH:13][O:14]3)=[CH:9][CH:8]=2)[CH2:2]1)[CH:37]([CH3:39])[CH3:38]

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 6561IsobutyraldehydeHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 71506445N-(4-(7-(azetidin-3-ylethynyl)-4-oxo-4H-chromen-3-yl)phenyl)methanesulfonamide

Product 1

HCID 71506634N-(4-(7-((1-isobutylazetidin-3-yl)ethynyl)-4-oxo-4H-chromen-3-yl)phenyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 21493386Dce thfSolvent

Procedure

To a mixture of N-(4-(7-(azetidin-3-ylethynyl)-4-oxo-4H-chromen-3-yl)phenyl)methanesulfonamide.trifluoroacetic acid salt (75 mgs, 0.190 mmol) in 1,2-dichloroethane/tetrahydrofuran (3 mL/0.5 mL), was added isobutyraldehyde (0.03 mL, 0.285 mmol), triethylamine (0.05 mL, 0.38 mmol) and sodium triacetoxyborohydride (60 mgs, 0.285 mmol). The mixture was stirred at room temperature for 16 hours, then the reaction mixture was quenched by adding aqueous 1N sodium hydroxide, and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was triturated and washed with diethylether to give N-(4-(7-((1-isobutylazetidin-3-yl)ethynyl)-4-oxo-4H-chromen-3-yl)phenyl)methanesulfonamide:

Workup

  1. customthe reaction mixture was quenched
  2. additionby adding aqueous 1N sodium hydroxide
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe extract was dried over magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was triturated
  7. washwashed with diethylether

Sources & evidence

ORD record
ord-acbc44b9f8dc4b2980c5c5bc601f43d3
Source dataset
uspto-grants-2014_03
Patent number
US08673966B2

Reaction notes

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