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2-Aminothiazole → HCID 11723599, 화합물

HRID 2213110
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HRID 2213110 반응식
Br[CH:2]([CH3:19])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[C:7]([O:17][CH3:18])[CH:6]=1)=O.[NH2:20][C:21]1[S:22][CH:23]=[CH:24][N:25]=1>C(O)C>[CH3:18][O:17][C:7]1[CH:6]=[C:5]([C:3]2[N:20]=[C:21]3[N:25]([C:2]=2[CH3:19])[CH:24]=[CH:23][S:22]3)[CH:10]=[CH:9][C:8]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1
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참가 물질

4

반응물 2

HCID 21552-AminothiazoleHCID 219565192-Bromo-1-(3-methoxy-4-pyridin-2-ylphenyl)propan-1-one

생성물 1

HCID 11723599HCID 11723599, 화합물

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of 2-bromo-1-(3-methoxy-4-pyridin-2-ylphenyl)propan-1-one (153 mg, 0.50 mmol) and 2-aminothiazole (50 mg, 0.50 mmol) in ethanol (1 mL) was heated to reflux for 12 h, then concentrated. The residue was dissolved in ethyl acetate (25 mL) and washed with saturated aqueous NaHCO3 (10 mL) and brine (10 mL). The organic layer was dried (MgSO4), concentrated and purified by flash column chromatography on silica gel eluting with EtOAc:hexanes (2:1 to 1:0) to afford 6-(3-methoxy-4-pyridin-2-ylphenyl)-5-methylimidazo[2,1-b][1,3]thiazole. 1H NMR (CDCl3, 500 MHz) δ 8.73 (m, 1H), 7.94 (d, 1H), 7.88 (d, 1H), 7.73 (dt, 1H), 7.52 (s, 1H), 7.35 (dd, 1H), 7.34 (dd, 1H), 7.22 (m, 1H), 6.86 (dd, 1H), 3.98 (s, 3H), 2.66 (s, 3H) ppm. MS (ESI) 322 (M)+.

후처리

  1. temperatureto reflux for 12 h
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in ethyl acetate (25 mL)
  4. washwashed with saturated aqueous NaHCO3 (10 mL) and brine (10 mL)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. concentrationconcentrated
  7. custompurified by flash column chromatography on silica gel eluting with EtOAc:hexanes (2:1 to 1:0)

출처 및 근거

ORD 기록
ord-fbe28aef313741ad8dca150a599a7cc7
출처 데이터셋
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07105533B2

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