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

HRID 596104Notes

Reaction equation

HRID 596104 reaction equation
[NH2:1][C:2]1[C:7]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[C:10]([F:17])[CH:9]=2)=[CH:6][C:5]([C:18]2[CH2:19][NH:20][C:21](=[O:23])[CH:22]=2)=[CH:4][N:3]=1>CO.[Pd]>[NH2:1][C:2]1[C:7]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[C:10]([F:17])[CH:9]=2)=[CH:6][C:5]([CH:18]2[CH2:22][C:21](=[O:23])[NH:20][CH2:19]2)=[CH:4][N:3]=1

Participants

4

Reactant 1

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

Product 1

HCID 1180447264-(2-Amino-5-(5-oxopyrrolidin-3-yl)pyridin-3-yl)-2-fluorobenzoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 4-(2-amino-5-(5-oxo-2,5-dihydro-1H-pyrrol-3-yl)pyridin-3-yl)-2-fluorobenzoic acid (100 mg, 0.319 mmol) in MeOH (15 mL) under N2 atmosphere was added Pd—C (67.9 mg, 0.064 mmol). The reaction mixture was stirred at room temperature for 24 h under H2 balloon. The reaction mixture was filter through Celite and washed with methanol. The filtrate was evaporated. The crude was proceed for next step. LCMS(m/z): 316.2 (MH+), 0.338 min.

Workup

  1. filtrationThe reaction mixture was filter through Celite
  2. washwashed with methanol
  3. customThe filtrate was evaporated
  4. custom316.2 (MH+), 0.338 min.

Sources & evidence

ORD record
ord-deac39459b0a42bfa57de071a8e88e9d
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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