Gamma-Butyrolactone → HCID 178520695, 화합물

HRID 45862

반응식

HRID 45862 반응식
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[C:9]([C:13]3[CH:14]=[C:15]([NH:19][C:20]([NH:22][C:23]4[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=4)=[O:21])[CH:16]=[CH:17][CH:18]=3)=[N:10][NH:11][CH:12]=2)[CH:5]=[CH:4][N:3]=1.[C:33]1(=[O:38])[O:37][CH2:36][CH2:35][CH2:34]1.[Na].C[Si](C)(C)N[Si](C)(C)C>O1CCCC1>[OH:38][CH2:33][CH2:34][CH2:35][C:36]([NH:1][C:2]1[CH:7]=[C:6]([C:8]2[C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([NH:19][C:20](=[O:21])[NH:22][C:23]4[CH:28]=[CH:27][C:26]([C:29]([F:31])([F:32])[F:30])=[CH:25][CH:24]=4)[CH:14]=3)=[N:10][NH:11][CH:12]=2)[CH:5]=[CH:4][N:3]=1)=[O:37]

참가 물질

5

반응물 3

HCID 7302Gamma-ButyrolactoneHCID 45051731Sodium hexamethyidisilazaneHCID 178507322HCID 178507322, 화합물

생성물 1

HCID 178520695HCID 178520695, 화합물수율 59%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

30 mg (0.068 mmol) of 1-{3-[4-(2-aminopyridin-4-yl)-1H-pyrazol-3-yl]phenyl}-3-[4-(trifluoromethyl)phenyl]urea were dissolved in 2 ml of dry tetrahydrofuran and 15 μl (0.34 mmol) of γ-butyrolactone were added. The reaction mixture was cooled to 0° C. and a solution of 680 μl (0.68 mmol) of hexamethyldisilazane sodium salt 1M in THF in 2 ml of the same solvent were added dropwise. The mixture was maintained at 0° C. for 6 hours and at room temperature overnight, then partitioned between dichloromethane and water. The organic phase was dried over sodium sulphate and evaporated. The crude was finally purified by preparative HPLC in reverse phase conditions (basic eluant), giving 20 mg (59%) of the title compound.

후처리

  1. temperatureThe mixture was maintained at 0° C. for 6 hours and at room temperature overnight
  2. custompartitioned between dichloromethane and water
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. customevaporated
  5. customThe crude was finally purified by preparative HPLC in reverse phase conditions (basic eluant)

출처 및 근거

ORD 기록
ord-3cff4afe910941b08835c59a82d566ad
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541575B2

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