Diethanolamine → 4-(4-(3-Cyano-4-(ethylsulfonyl)phenylamino)-4-oxobutyl)phenylboronic acid

HRID 735503노트

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HRID 735503 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH2:23][CH3:24])(=[O:22])=[O:21])=[C:16]([C:25]#[N:26])[CH:15]=2)=[O:12])=[CH:4][CH:3]=1.CC1(C)C[O:32][B:31](B2OCC(C)(C)CO2)[O:30]C1.C([O-])(=O)C.[K+].N(CCO)CCO>C(O)(C)C.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe]>[C:25]([C:16]1[CH:15]=[C:14]([NH:13][C:11](=[O:12])[CH2:10][CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([B:31]([OH:32])[OH:30])=[CH:3][CH:4]=2)[CH:19]=[CH:18][C:17]=1[S:20]([CH2:23][CH3:24])(=[O:22])=[O:21])#[N:26]

참가 물질

7

반응물 4

HCID 8113DiethanolamineHCID 517044Potassium AcetateHCID 2734316Bis(neopentyl glycolato)diboronHCID 578426674-(4-Bromophenyl)-N-(3-cyano-4-(ethylsulfonyl)phenyl)butanamide

생성물 1

HCID 578426844-(4-(3-Cyano-4-(ethylsulfonyl)phenylamino)-4-oxobutyl)phenylboronic acid수율 57.9%

시약·촉매·용매 2

HCID 53485975CID 53485975촉매HCID 3776Isopropanol용매

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온도
80 °C

실험 절차

A flask containing 6C (83 mg, 0.19 mmol), 5,5,5′,5′-tetramethyl-[2,2′]bi[[1,3,2]dioxaborinanyl] (47.6 mg, 0.211 mmol), potassium acetate (83 mg, 0.84 mmol), and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (4.4 mg, 0.0060 mmol) was purged with argon. DMSO (1 mL) was added, and the reaction mixture was degassed with three cycles of vacuum followed by argon backfill. The reaction mixture was heated for 2 h at 80° C., cooled to rt, and diluted with water (100 mL). The aqueous solution was extracted with diethyl ether (3×25 mL), dried (MgSO4), and concentrated under reduced pressure. The residue was dissolved in a mixture of diethyl ether (1 mL), DCM (˜0.1 mL), and EtOAc (˜0.1 mL). Diethanolamine (22 mg, 0.21 mmol) in isopropanol (0.5 mL) was added, and the reaction mixture was stirred overnight at rt. The reaction mixture was concentrated, and the residue was purified by reverse phase HPLC (under the standard acidic conditions) to give 6D (44 mg, 57%) as a clear oil. MS (ESI) m/z 425.4 (M+CH3OH—H2O+H)+.

후처리

  1. customwas purged with argon
  2. additionDMSO (1 mL) was added
  3. customthe reaction mixture was degassed with three cycles of vacuum
  4. temperaturecooled to rt
  5. additiondiluted with water (100 mL)
  6. extractionThe aqueous solution was extracted with diethyl ether (3×25 mL)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated under reduced pressure
  9. dissolutionThe residue was dissolved in a mixture of diethyl ether (1 mL), DCM (˜0.1 mL), and EtOAc (˜0.1 mL)
  10. concentrationThe reaction mixture was concentrated
  11. customthe residue was purified by reverse phase HPLC (under the standard acidic conditions)

출처 및 근거

ORD 기록
ord-dbf33763284642fc828585fa8e4469ba
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592331B2

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