1,2-Dichloroethane → (R)-3-fluoro-4-(1-(2-fluorophenylsulfonyl)piperidin-3-ylcarbamoyl)phenylboronic acid

HRID 595795

반응식

HRID 595795 반응식
[B:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[C:6]([F:13])[CH:5]=1)([OH:3])[OH:2].[F:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21]([N:24]1[CH2:29][CH2:28][CH2:27][C@@H:26]([NH2:30])[CH2:25]1)(=[O:23])=[O:22].CCN(C(C)C)C(C)C.C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl>C1COCC1.CN(C=O)C>[F:13][C:6]1[CH:5]=[C:4]([B:1]([OH:2])[OH:3])[CH:12]=[CH:11][C:7]=1[C:8](=[O:10])[NH:30][C@@H:26]1[CH2:27][CH2:28][CH2:29][N:24]([S:21]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[F:14])(=[O:22])=[O:23])[CH2:25]1

참가 물질

8

반응물 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27632014-Carboxy-3-fluorophenylboronic acidHCID 28418373(R)-1-(2-fluorophenylsulfonyl)piperidin-3-amine

생성물 1

HCID 123376552(R)-3-fluoro-4-(1-(2-fluorophenylsulfonyl)piperidin-3-ylcarbamoyl)phenylboronic acid

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 4-borono-2-fluorobenzoic acid (160 mg, 0.870 mmol), (R)-1-(2-fluorophenylsulfonyl)piperidin-3-amine (225 mg, 0.870 mmol), and DIEA (456 μL, 2.61 mmol) in THF (1450 μL) and DMF (1450 μL) was added HOAt (237 mg, 1.740 mmol) and EDC (417 mg, 2.175 mmol). After 3 h stirring at room temperature, the reaction mixture was extracted with EtOAc. The organic layer was washed with NaHCO3, water and brine, dried over anhydrous sodium sulfate, filtered off, and concentrated in vacuo yielding (R)-3-fluoro-4-(1-(2-fluorophenylsulfonyl)piperidin-3-ylcarbamoyl)phenylboronic acid, which was used in next step reaction without purification. LCMS (m/z): 425.2 (MH+), 0.72 min.

후처리

  1. extractionthe reaction mixture was extracted with EtOAc
  2. washThe organic layer was washed with NaHCO3, water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered off
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-4e5480f451d54182a4b5b1775d3e9eee
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242996B2

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