Hydrochloric Acid → 3-{5-[5-(4-Isobutyl-phenyl)-[1,2,4]oxadiazol-3-yl]-pyridin-2-ylamino}-cyclobutanecarboxylic acid hydrochloride

HRID 2242260Notes

Reaction equation

HRID 2242260 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([CH2:19][CH:20]([CH3:22])[CH3:21])=[CH:15][CH:14]=3)[O:10][N:9]=2)=[CH:4][N:3]=1.Cl.C([O:26][C:27]([C@H:29]1[CH2:32][C@@H:31]([NH2:33])[CH2:30]1)=[O:28])C.OP([O-])([O-])=O.[K+].[K+].[OH-].[Na+].Cl>O.CS(C)=O>[ClH:1].[CH2:19]([C:16]1[CH:17]=[CH:18][C:13]([C:11]2[O:10][N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:33][CH:31]4[CH2:32][CH:29]([C:27]([OH:28])=[O:26])[CH2:30]4)=[N:3][CH:4]=3)[N:12]=2)=[CH:14][CH:15]=1)[CH:20]([CH3:22])[CH3:21]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24450Potassium Phosphate, DibasicHCID 592042672-Chloro-5-[5-(4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]pyridineHCID 178472514HCID 178472514, compound

Product 1

HCID 686492023-{5-[5-(4-Isobutyl-phenyl)-[1,2,4]oxadiazol-3-yl]-pyridin-2-ylamino}-cyclobutanecarboxylic acid hydrochlorideYield 86%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of 2-chloro-5-[5-(4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]pyridine (50 mg, 0.16 mmol), cis-3-amino-cylcobutanecarboxylic acid ethyl ester, hydrochloride (57.1 mg, 0.319 mmol), potassium phosphate dibasic (58.3 mg, 0.335 mmol) and DMSO (5 mL) was stirred in a sealed tube in the microwave at 200° C. for 10 minutes. The reaction mixture was cooled to room temperature and concentrated in vacuo. The resulting residue was dissolved in EtOH (3 mL). NaOH (19 mg, 0.478 mmol) and water (2 mL) were added to the reaction mixture and stirred in a sealed tube in the microwave at 180° C. for 10 minutes. The reaction mixture was cooled to room temperature, acidified with 1N HCl (5 mL), filtered and dried to provide the title compound (59 mg, 86% yield) as a solid.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe resulting residue was dissolved in EtOH (3 mL)
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-2019c6b59a29447089fb13a6878b8b61
Source dataset
uspto-grants-2010_03
Patent number
US07671043B2

Reaction notes

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