Hydrochloric Acid → (2-Fluoro-4-iodo-phenyl)-(4-[1,2,4]oxadiazol-5-yl-pyridin-3-yl)-amine

HRID 658378Notes

Reaction equation

HRID 658378 reaction equation
C(OC([C:6]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[NH:17][C:18]2[CH:23]=[CH:22][C:21]([I:24])=[CH:20][C:19]=2[F:25])[O:8][N:7]=1)=O)C.[Li+].[OH-].Cl>C1COCC1.O.O>[F:25][C:19]1[CH:20]=[C:21]([I:24])[CH:22]=[CH:23][C:18]=1[NH:17][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][C:11]=1[C:9]1[O:8][N:7]=[CH:6][N:10]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 590267925-[3-(2-Fluoro-4-iodo-phenylamino)-pyridin-4-yl]-[1,2,4]oxadiazole-3-carboxylic acid ethyl ester

Product 1

HCID 59026781(2-Fluoro-4-iodo-phenyl)-(4-[1,2,4]oxadiazol-5-yl-pyridin-3-yl)-amineYield 92.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 5-[3-(2-Fluoro-4-iodo-phenylamino)-pyridin-4-yl]-[1,2,4]oxadiazole-3-carboxylic acid ethyl ester (1.8 g, 3.96 mmol) in THF-H2O (1:1)(20 mL) LiOH (0.19 g, 7.93 mmL) was added. The reaction mixture was stirred for 2 hrs at RT. The pH was adjusted to 5 with 1N HCl and the mixture was diluted with water. A solid precipitated and was filtered to give the product (1.4 g). LC/MS (Method A) [4.39 min; 383(M+1)]

Workup

  1. customA solid precipitated
  2. filtrationwas filtered

Sources & evidence

ORD record
ord-4b4392be67ac4154a3a6ba3709508e6e
Source dataset
uspto-grants-2011_12
Patent number
US08076486B2

Reaction notes

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