Trifluoroacetic acid → N-{1-[4'-(4-Amino-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarbonyl}-methanesulfonamide

HRID 45601Notes

Reaction equation

HRID 45601 reaction equation
C(OC(=O)[NH:7][C:8]1[C:9]([CH3:35])=[N:10][O:11][C:12]=1[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]3([C:28]([NH:30][S:31]([CH3:34])(=[O:33])=[O:32])=[O:29])[CH2:27][CH2:26]3)=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)(C)(C)C.C(O)(C(F)(F)F)=O.CCOC(C)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:7][C:8]1[C:9]([CH3:35])=[N:10][O:11][C:12]=1[C:13]1[CH:14]=[CH:15][C:16]([C:19]2[CH:20]=[CH:21][C:22]([C:25]3([C:28]([NH:30][S:31]([CH3:34])(=[O:33])=[O:32])=[O:29])[CH2:27][CH2:26]3)=[CH:23][CH:24]=2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 66577855{5-[4'-(1-Methanesulfonylaminocarbonyl-cyclopropyl)-biphenyl-4-yl]-3-methyl-isoxazol-4-yl}-carbamic acid tert-butyl esterHCID 86584982Sodium bicarbonate ethyl acetate

Product 1

HCID 66577832N-{1-[4'-(4-Amino-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarbonyl}-methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

{5-[4′-(1-Methanesulfonylaminocarbonyl-cyclopropyl)-biphenyl-4-yl]-3-methyl-isoxazol-4-yl}-carbamic acid tert-butyl ester (0.25 g, 0.49 mmol)) in CH2Cl2 (2 mL) and TFA (2 mL) was stirred overnight then poured into EtOAc/NaHCO3 (aq). The organic layer was concentrated to yield the title compound.

Workup

  1. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-a715fe4c2359439cae7db5105e23cd95
Source dataset
uspto-grants-2013_09
Patent number
US08541587B2

Reaction notes

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