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 405022ノート

反応式

HRID 405022 の反応式
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]

参加物

8

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b67db9a80ed34386a8f6c04ab3671bbc
出典データセット
uspto-grants-2014_06
特許番号
US08748412B2

反応ノート

読み込み中…