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Potassium Carbonate → tert-Butyl (5-{[4-{[4-(difluoromethoxy)phenyl]amino}-1,1-dioxido-3-oxo-5-phenylisothiazol-2(3H)-yl]methyl}pyridin-2-yl)carbamate

HRID 729268
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HRID 729268 반응식
[F:1][CH:2]([F:11])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=1.Cl[C:13]1[C:14](=[O:26])[NH:15][S:16](=[O:25])(=[O:24])[C:17]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[C:27]([O:31][C:32](=[O:42])[NH:33][C:34]1[CH:39]=[CH:38][C:37]([CH2:40]Br)=[CH:36][N:35]=1)([CH3:30])([CH3:29])[CH3:28].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:1][CH:2]([F:11])[O:3][C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:13]2[C:14](=[O:26])[N:15]([CH2:40][C:37]3[CH:38]=[CH:39][C:34]([NH:33][C:32](=[O:42])[O:31][C:27]([CH3:29])([CH3:28])[CH3:30])=[N:35][CH:36]=3)[S:16](=[O:25])(=[O:24])[C:17]=2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:8][CH:9]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 11430Potassium CarbonateHCID 7373634-(Difluoromethoxy)anilineHCID 23030321tert-Butyl (5-(bromomethyl)pyridin-2-yl)carbamateHCID 686616564-Chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide

생성물 1

HCID 86623729tert-Butyl (5-{[4-{[4-(difluoromethoxy)phenyl]amino}-1,1-dioxido-3-oxo-5-phenylisothiazol-2(3H)-yl]methyl}pyridin-2-yl)carbamate수율 13%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

[4-[Difluoromethoxy)phenyl]amine (0.27 g, 1.7 mmol) was added to an ice cold solution of 4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide (0.41 g, 1.7 mmol) in DMF (4 ml) and the mixture was stirred for 1 h. tert-Butyl[5-(bromomethyl)pyridin-2-yl]carbamate (0.48 g, 1.7 mmol) and anhydrous potassium carbonate (0.23 g, 1.7 mmol) were added. The reaction mixture was stirred over night, concentrated and the residue was dissolved in DCM. The mixture was washed with water and concentrated and the residue was purified using preparative HPLC to give the title compound (0.12 g, 13%). 1H NMR (400 MHz, d6-DMSO): δ 1.41 (s, 9H), 3.77 (dd, 2H), 7.22-7.24 (m, 3H), 7.27 (t, 1H), 7.39-7.45 (m, 5H), 7.48 (d, 1H), 7.78 (d, 1H), 7.86 (dd, 2H), 9.57 (s, 1H), 11.18 (s, 1H); Mass Spectrum: M+H+ 573.

후처리

  1. additionwere added
  2. concentrationconcentrated
  3. dissolutionthe residue was dissolved in DCM
  4. washThe mixture was washed with water
  5. concentrationconcentrated
  6. customthe residue was purified

출처 및 근거

ORD 기록
ord-a0e16348babc42139ec1a602863c685a
출처 데이터셋
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07582629B2

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