Potassium Acetate → (S)-tert-Butyl 4-(1-amino-3-(4-(2-methyl-3-oxoisoindolin-5-yl)phenyl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

HRID 216974

반응식

HRID 216974 반응식
[NH2:1][C:2](=[O:37])[C@@H:3]([NH:20][C:21]([C:23]1([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1)=[O:22])[CH2:4][C:5]1[CH:10]=[CH:9][C:8](B2OC(C)(C)C(C)(C)O2)=[CH:7][CH:6]=1.Br[C:39]1[CH:47]=[C:46]2[C:42]([CH2:43][N:44]([CH3:49])[C:45]2=[O:48])=[CH:41][CH:40]=1.C([O-])(=O)C.[K+]>C(#N)C.O>[NH2:1][C:2](=[O:37])[C@@H:3]([NH:20][C:21]([C:23]1([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:33])([CH3:35])[CH3:34])[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1)=[O:22])[CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:39]2[CH:47]=[C:46]3[C:42](=[CH:41][CH:40]=2)[CH2:43][N:44]([CH3:49])[C:45]3=[O:48])=[CH:9][CH:10]=1

참가 물질

6

반응물 3

HCID 517044Potassium AcetateHCID 469420086-bromo-2-methyl-2,3-dihydro-1H-isoindol-1-oneHCID 59568592(S)-tert-Butyl 4-(1-amino-1-oxo-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

생성물 1

HCID 59568554(S)-tert-Butyl 4-(1-amino-3-(4-(2-methyl-3-oxoisoindolin-5-yl)phenyl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate수율 64.3%

시약·촉매·용매 2

HCID 962Water용매2회HCID 6342Acetonitrile용매

실험 절차

(S)-tert-Butyl 4-(1-amino-1-oxo-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 16, step (i), 300 mg), 6-bromo-2-methylisoindolin-1-one (Example 30, step (i), 131 mg) and potassium acetate (171 mg) in a mixture of acetonitrile (15 mL) and water (5 mL) was stirred under nitrogen at 90° C. with 1,1 bis(di-tert-butylphosphino)ferrocene palladium dichloride (378 mg). After 4 h the reaction mixture was cooled to room temperature and diluted with water (50 mL). The products were extracted with ethyl acetate (3×50 mL) and the combined extracts dried over magnesium sulfate and concentrated to afford the sub-titled compound (200 mg).

후처리

  1. extractionThe products were extracted with ethyl acetate (3×50 mL)
  2. dry with materialthe combined extracts dried over magnesium sulfate
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-42abd4b3fe714ff9baa8e0a42f8b6af3
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193239B2

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