Methanol → 3-(5-Methylpyridin-2-yl)-5-(pyrrolidine-1-carbonyl)benzoic acid

HRID 1845224Notes

Reaction equation

HRID 1845224 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([CH:15]=[C:16]([C:18]([N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)=[O:19])[CH:17]=2)[C:11]([O:13]C)=[O:12])=[N:6][CH:7]=1.CO.[OH-].[Na+]>O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([CH:15]=[C:16]([C:18]([N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)=[O:19])[CH:17]=2)[C:11]([OH:13])=[O:12])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 58188359Methyl 3-(5-methylpyridin-2-yl)-5-(pyrrolidine-1-carbonyl)benzoate

Product 1

HCID 581882913-(5-Methylpyridin-2-yl)-5-(pyrrolidine-1-carbonyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a round-bottom flask were charged methyl 3-(5-methylpyridin-2-yl)-5-(pyrrolidine-1-carbonyl)benzoate (0.80 g, 2.47 mmol), methanol (40 mL), sodium hydroxide (0.20 g, 5.0 mmol) and water (10 mL). The mixture was stirred at room temperature for 1 h. The volatiles were removed under reduced pressure. The residue was treated with 1N HCl (10 mL), concentrated, and purified via preparative HPLC to afford the desired product. LC-MS: 311.5 [M+1]+; 1H NMR (400 MHz, DMSO-d6): 8.61 (t, J=1.7 Hz, 1H), 8.52 (t, J=0.8 Hz, 1H), 8.16 (t, J=1.8 Hz, 1H), 7.99 (t, J=1.5 Hz, 1H), 7.80 (d, J=8.2 Hz, 1H), 7.72-7.69 (m, 1H), 3.50 (t, J=6.7 Hz, 2H), 3.41 (t, J=6.5 Hz, 2H), 2.35 (s, 3H), 1.91-1.81 (m, 4H).

Workup

  1. customThe volatiles were removed under reduced pressure
  2. additionThe residue was treated with 1N HCl (10 mL)
  3. concentrationconcentrated
  4. custompurified via preparative HPLC

Sources & evidence

ORD record
ord-be1fb8ad35424d5a8e1675b3d971cbd3
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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