Trifluoroacetic acid → 4-(2-amino-5-(5-oxo-2,5-dihydro-1H-pyrrol-3-yl)pyridin-3-yl)-2-fluorobenzoic acid

HRID 596103Notes

Reaction equation

HRID 596103 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH2:12][N:11](C(OC(C)(C)C)=O)[C:10](=[O:20])[CH:9]=2)=[CH:4][C:3]=1[C:21]1[CH:26]=[CH:25][C:24]([C:27]([O:29]C(C)(C)C)=[O:28])=[C:23]([F:34])[CH:22]=1.C(O)(C(F)(F)F)=O>C1(C)C=CC=CC=1>[NH2:1][C:2]1[C:3]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([OH:29])=[O:28])=[C:23]([F:34])[CH:22]=2)=[CH:4][C:5]([C:8]2[CH2:12][NH:11][C:10](=[O:20])[CH:9]=2)=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118045974Tert-butyl 4-(6-amino-5-(4-(tert-butoxycarbonyl)-3-fluorophenyl)pyridin-3-yl)-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate

Product 1

HCID 1180467894-(2-amino-5-(5-oxo-2,5-dihydro-1H-pyrrol-3-yl)pyridin-3-yl)-2-fluorobenzoic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To tert-butyl 4-(6-amino-5-(4-(tert-butoxycarbonyl)-3-fluorophenyl)pyridin-3-yl)-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate (158 mg, 0.337 mmol) was added TFA (2 mL, 26.0 mmol). The reaction mixture was stirred at room temperature for 1 h. After toluene was added, the volatile solvents were evaporated. The crude product was used for the next step. LCMS(m/z): 314.2 (MH+), 0.382 min.

Workup

  1. customthe volatile solvents were evaporated
  2. custom314.2 (MH+), 0.382 min.

Sources & evidence

ORD record
ord-cb6c0fde9db14a8cba63b2e8837b33dd
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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