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

HRID 2242260노트

반응식

HRID 2242260 반응식
[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]

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2019c6b59a29447089fb13a6878b8b61
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07671043B2

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