Methanol → HCID 66605825, compound

HRID 2410803Notes

Reaction equation

HRID 2410803 reaction equation
[C:1]([C:4]1[C:9]2[NH:10][C:11]3[CH:12]=[C:13]([C:17]([O:19]C(C)C)=[O:18])[CH:14]=[CH:15][C:16]=3[C:8]=2[N:7]=[C:6]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:5]=1)(=[O:3])[NH2:2].CO.[OH-].[Na+]>C1COCC1>[C:1]([C:4]1[C:9]2[NH:10][C:11]3[CH:12]=[C:13]([C:17]([OH:19])=[O:18])[CH:14]=[CH:15][C:16]=3[C:8]=2[N:7]=[C:6]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:5]=1)(=[O:3])[NH2:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 66604406HCID 66604406, compound

Product 1

HCID 66605825HCID 66605825, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of isopropyl 4-carbamoyl-2-phenyl-5H-pyrido[3,2-b]indole-7-carboxylate (2 g, 5.36 mmol) in a mixture of THF (36 ml), MeOH (15 ml) and 1 N aqueous NaOH (12 ml, 120 mmol) was stirred at 25° C. overnight. The organic solvents were removed and the residue was dissolved in water, washed with DCM (20 mL), and acidified to about pH 3 with 1 N aqueous HCl to give a yellow gel-like precipitate. This was chilled in an ice bath and the precipitate was collected by filtration, washed with water, and dried to leave 4-carbamoyl-2-phenyl-5H-pyrido[3,2-b]indole-7-carboxylic acid (2.1 g, 5.1 mmol, 95% yield). MS (ESI) m/z 332.00 (M+H). 1H NMR (500 MHz, MeOD) δ ppm 8.67 (1H, d, J=8.55 Hz), 8.58-8.64 (1H, m), 8.54 (1H, s), 8.03-8.17 (3H, m), 7.67-7.79 (3H, m).

Workup

  1. customThe organic solvents were removed
  2. dissolutionthe residue was dissolved in water
  3. washwashed with DCM (20 mL)
  4. customto give a yellow gel-like precipitate
  5. temperatureThis was chilled in an ice bath
  6. filtrationthe precipitate was collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-6be76baf06604488b3e944722effa99d
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

Loading…