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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
ノート
印刷プレビュー

反応式

HRID 729268 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

[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.

後処理

  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

出典と根拠

ORDレコード
ord-a0e16348babc42139ec1a602863c685a
出典データセット
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07582629B2

反応ノート

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