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Potassium Carbonate → tert-Butyl 2-(3-(2-(4-methylthiazol-2-ylamino)pyridin-4-ylthio)phenoxy)acetate

HRID 910965
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HRID 910965 반응식
C(=O)([O-])[O-].[K+].[K+].[CH3:7][C:8]1[N:9]=[C:10]([NH:13][C:14]2[CH:19]=[C:18]([S:20][C:21]3[CH:22]=[C:23]([OH:27])[CH:24]=[CH:25][CH:26]=3)[CH:17]=[CH:16][N:15]=2)[S:11][CH:12]=1.Br[CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31]>CN(C=O)C.O>[CH3:7][C:8]1[N:9]=[C:10]([NH:13][C:14]2[CH:19]=[C:18]([S:20][C:21]3[CH:22]=[C:23]([CH:24]=[CH:25][CH:26]=3)[O:27][CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH:17]=[CH:16][N:15]=2)[S:11][CH:12]=1
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참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 578989303-(2-(4-Methylthiazol-2-ylamino)pyridin-4-ylthio)phenol

생성물 1

HCID 24826426tert-Butyl 2-(3-(2-(4-methylthiazol-2-ylamino)pyridin-4-ylthio)phenoxy)acetate수율 60%

시약·촉매·용매 2

HCID 962Water용매
HCID 6228
Dimethylformamide
용매

실험 절차

A mixture of potassium carbonate (1.08 g, 7.82 mmol), 3-(2-(4-methylthiazol-2-ylamino)pyridin-4-ylthio)phenol (0.274 g, 0.869 mmol), and tert-butyl 2-bromoacetate (0.169 g, 0.869 mmol) in DMF (5 mL). The reaction mixture was stirred at room temperature overnight, then diluted with water and extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered and concentrated. The residue was purified using prepacked silica gel column chromatography with 15-20% ethyl acetate to afford the desired product (0.224 g, 58.8% yield) as light yellow solid. 1H NMR (CDCl3) δ 8.08 (d, 1H), 7.33 (t, 1H), 7.15 (m, 1H), 7.04 (t, 1H), 6.98 (m, 1H), 6.57 (dd, 1H), 6.49 (dd, 1H), 6.33 (d, 1H), 4.50 (s, 2H, 2.22 (d, 3H), 1.46 (s, 9H); Mass spectrum (esi) m/z=430 (100)(M+H).

후처리

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified

출처 및 근거

ORD 기록
ord-3189a4eb91754b03a211f6874cb80d0c
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08022222B2

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