Sodium Hydroxide → HCID 178493175, compound

HRID 2233520Notes

Reaction equation

HRID 2233520 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:9][CH2:10][C:11](O)=O)[CH:4]=1.[NH2:14][C:15]1[C:20]([NH2:21])=[CH:19][C:18]([I:22])=[CH:17][N:16]=1.[OH-].[Na+]>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:9][CH2:10][C:11]2[NH:14][C:15]3=[N:16][CH:17]=[C:18]([I:22])[CH:19]=[C:20]3[N:21]=2)[CH:4]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 21882727HCID 21882727, compound2×HCID 218827665-Iodopyridine-2,3-diamine

Product 1

HCID 178493175HCID 178493175, compoundYield 61.2%

Conditions

Temperature
140 °C

Procedure

With stirring, a mixture of 8.06 g of 3-(4-methoxypyridin-2-yl)propionic acid (starting material B1), 9.5 g of 2,3-diamino-5-iodopyridine (Cugola et al., Bioorg. Med. Chem. Lett. 22, 2749-2754 (1996)) and 150 g of polyphosphoric acid (PPA) is heated at 140° C. for 22 hours. After cooling, the mixture is poured into about 1000 ml of ice-water and then neutralized (pH 7-8) using 6N aqueous sodium hydroxide solution. The mixture is extracted four times with ethyl acetate and the combined organic phases are evaporated to dryness. The residue is crystallized first from ethyl acetate and then from methanol, giving 9.4 g of the title compound as a light-beige powder of m.p. 207-208° C.; the mass spectrum shows the molecular peak MH+ at 381.2 Da.

Workup

  1. temperatureAfter cooling
  2. extractionThe mixture is extracted four times with ethyl acetate
  3. customthe combined organic phases are evaporated to dryness
  4. customThe residue is crystallized first from ethyl acetate

Sources & evidence

ORD record
ord-f378f8f15695497d97abd3f65039bc4e
Source dataset
uspto-grants-2010_05
Patent number
US07709488B2

Reaction notes

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