Potassium Iodide → 3-{4-[5-(4-tert-Butoxycarbonylamino-phenyl)-[1,2,4]oxadiazol-3-yl]-3-fluoro-phenyl}-2-(2-piperidin-1-yl-pyrimidin-4-ylamino)-propionic acid

HRID 405022노트

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HRID 405022 반응식
C([O:3][C:4](=[O:41])[CH:5]([NH:33][C:34]1[CH:39]=[CH:38][N:37]=[C:36](Cl)[N:35]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:17]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:20][CH:19]=3)[O:15][N:14]=2)=[C:9]([F:32])[CH:8]=1)C.C(OC(=O)C(N)CC1C=CC(C2N=C([C:59]3[CH:64]=[CH:63][C:62]([NH:65][C:66](OC(C)(C)C)=O)=CC=3)ON=2)=C(F)C=1)C.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+].ClC1N=C(Cl)C=CN=1>CN(C=O)C.CCCC[N+](CCCC)(CCCC)CCCC.[Br-]>[C:28]([O:27][C:25]([NH:24][C:21]1[CH:22]=[CH:23][C:18]([C:16]2[O:15][N:14]=[C:13]([C:10]3[CH:11]=[CH:12][C:7]([CH2:6][CH:5]([NH:33][C:34]4[CH:39]=[CH:38][N:37]=[C:36]([N:65]5[CH2:62][CH2:63][CH2:64][CH2:59][CH2:66]5)[N:35]=4)[C:4]([OH:3])=[O:41])=[CH:8][C:9]=3[F:32])[N:17]=2)=[CH:19][CH:20]=1)=[O:26])([CH3:29])([CH3:31])[CH3:30]

참가 물질

8

반응물 5

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 775312,4-DichloropyrimidineHCID 66630730Ethyl 2-amino-3-(4-(5-(4-((tert-butoxycarbonyl)amino)phenyl)-1,2,4-oxadiazol-3-yl)-3-fluorophenyl)propanoateHCID 866607833-{4-[5-(4-tert-Butoxycarbonylamino-phenyl)-[1,2,4]oxadiazol-3-yl]-3-fluoro-phenyl}-2-(2-chloro-pyrimidin-4-ylamino)-propionic acid ethyl ester

생성물 1

HCID 666317953-{4-[5-(4-tert-Butoxycarbonylamino-phenyl)-[1,2,4]oxadiazol-3-yl]-3-fluoro-phenyl}-2-(2-piperidin-1-yl-pyrimidin-4-ylamino)-propionic acid

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

3-{4-[5-(4-tert-Butoxycarbonylamino-phenyl)-[1,2,4]oxadiazol-3-yl]-3-fluoro-phenyl}-2-(2-chloro-pyrimidin-4-ylamino)-propionic acid ethyl ester. To solution of 2-Amino-3-{4-[5-(4-tert-butoxycarbonylamino-phenyl)-[1,2,4]oxadiazol-3-yl]-3-fluorophenyl}propionic acid ethyl ester in DMF (20 mL) were added sodium carbonate (360 mg, 3.4 mmol), potassium iodide (10 mg), TBAB (10 mg), and 2,4-dichloro-pyrimidine (503 mg, 3.4 mmol). The mixture was heated at 50° C. for 4 hrs. The mixture was cooled to room temperature and partitioned between ethyl acetate and water. The combined organic layers were washed with brine, dried over sodium sulfate, filtrated, concentrated, and purified by chromatography to give the title compound (96 mg).

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. custompartitioned between ethyl acetate and water
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltrated
  6. concentrationconcentrated
  7. custompurified by chromatography

출처 및 근거

ORD 기록
ord-b67db9a80ed34386a8f6c04ab3671bbc
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748412B2

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