Acetonitrile → HCID 135416291, 화합물

HRID 2191548노트

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HRID 2191548 반응식
Br[C:2]1[N:6]=[C:5]([N:7]2[CH2:12][CH2:11][CH:10]([NH:13][C:14](=[O:20])[O:15][CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:9][CH2:8]2)[S:4][N:3]=1.CC1(C)C(C)(C)OB([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[OH:35])O1.C([O-])([O-])=O.[K+].[K+].CC#N>O>[OH:35][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[C:2]1[N:6]=[C:5]([N:7]2[CH2:12][CH2:11][CH:10]([NH:13][C:14](=[O:20])[O:15][CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:9][CH2:8]2)[S:4][N:3]=1

참가 물질

6

반응물 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 27346222-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 58182722HCID 58182722, 화합물

생성물 1

HCID 135416291HCID 135416291, 화합물

시약·촉매·용매 1

HCID 962Water용매2회

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온도
175 °C

실험 절차

A mixture of isobutyl 1-(3-bromo-1,2,4-thiadiazol-5-yl)piperidin-4-ylcarbamate (0.38 g, 1.1 mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenol (0.35 g, 1.6 mmol), Pd(Ph3)4 (12 mg, 11 μmol), K2CO3 (0.29 g, 2.1 mmol), CH3CN (3.0 mL), and H2O (0.3 mL) was sealed in a microwave vessel and heated by microwave irradiation at 175° C. for 15 minutes. The reaction was cooled to room temperature, diluted with water, and extracted with CH2Cl2. The combined extracts were washed with water, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by reverse phase HPLC (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)) to yield isobutyl 1-(3-(2-hydroxyphenyl)-1,2,4-thiadiazol-5-yl)piperidin-4-ylcarbamate. LC/MS: m/z 377.3 (M+H)+ at 3.77 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

후처리

  1. customwas sealed in a microwave vessel
  2. temperatureThe reaction was cooled to room temperature
  3. extractionextracted with CH2Cl2
  4. washThe combined extracts were washed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by reverse phase HPLC (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA))

출처 및 근거

ORD 기록
ord-2a3579cea98e4e7aa43a6eb252d13043
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08329702B2

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