Ammonium Hydroxide → GPR119 agonist 2

HRID 532488

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HRID 532488 반응식
[CH:1]([C:4]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][CH:12]([OH:15])[CH2:11][CH2:10]2)[O:6][N:5]=1)([CH3:3])[CH3:2].[H-].[Na+].[F:18][C:19]1[CH:24]=[C:23]([S:25]([CH3:28])(=[O:27])=[O:26])[CH:22]=[CH:21][C:20]=1[C:29]1[C:33]2[N:34]=[CH:35][N:36]=[C:37](S(C)(=O)=O)[C:32]=2[S:31][CH:30]=1.[OH-].[NH4+]>CN(C)C=O>[F:18][C:19]1[CH:24]=[C:23]([S:25]([CH3:28])(=[O:27])=[O:26])[CH:22]=[CH:21][C:20]=1[C:29]1[C:33]2[N:34]=[CH:35][N:36]=[C:37]([O:15][CH:12]3[CH2:11][CH2:10][N:9]([C:7]4[O:6][N:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[N:8]=4)[CH2:14][CH2:13]3)[C:32]=2[S:31][CH:30]=1

참가 물질

6

반응물 4

HCID 14923Ammonium HydroxideHCID 24758Sodium hydrideHCID 218977441-(3-Isopropyl-1,2,4-oxadiazol-5-YL)piperidin-4-OLHCID 682992807-(2-Fluoro-4-methanesulfonyl-phenyl)-4-methanesulfonyl-thieno[3,2-d]pyrimidine

생성물 1

HCID 86699298GPR119 agonist 2수율 59.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-ol (30 mg) was dissolved in N,N-dimethylformamide (2 mL) and cooled to an internal temperature of 0° C. Then, NaH (9 mg) was slowly added thereto and stirred for 30 min. 7-(2-fluoro-4-methanesulfonyl-phenyl)-4-methanesulfonyl-thieno[3,2-d]pyrimidine (50 mg) synthesized in Preparation Example 2 was slowly added thereto and heated to room temperature, followed by stirring for 2 hours. Then, the reaction mixture was mixed with a saturated solution of ammonium hydroxide, and extracted twice with ethyl acetate. The organic layer thus obtained was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain a foamy residue. The residue was crystallized in the presence of diethyl ether to obtain the title compound (40 mg) as a whitish solid.

후처리

  1. additionwas slowly added
  2. temperatureheated to room temperature
  3. stirringby stirring for 2 hours
  4. extractionextracted twice with ethyl acetate
  5. customThe organic layer thus obtained
  6. washwas washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customto obtain a foamy residue
  10. customThe residue was crystallized in the presence of diethyl ether

출처 및 근거

ORD 기록
ord-a6374645a9fd4d26a7e8ae902fa7a44a
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853213B2

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