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Potassium Carbonate → (S)-methyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(3-(1-methyl-1H-indazol-5-yl)-2-oxopyridin-1(2H)-yl)benzo[d]thiazol-6-yl)acetate

HRID 879314
ノート
印刷プレビュー

反応式

HRID 879314 の反応式
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[C:12](=[O:17])[NH:13][CH:14]=[CH:15][CH:16]=3)=[CH:8][CH:9]=2)[CH:4]=[N:3]1.Br[C:19]1[S:20][C:21]2[C:27]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=3)=[C:26]([C@H:35]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])[C:36]([O:38][CH3:39])=[O:37])[C:25]([CH3:45])=[CH:24][C:22]=2[N:23]=1.CN[C@@H]1CCCC[C@H]1NC.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cu]I>[C:41]([O:40][C@@H:35]([C:26]1[C:25]([CH3:45])=[CH:24][C:22]2[N:23]=[C:19]([N:13]3[CH:14]=[CH:15][CH:16]=[C:11]([C:7]4[CH:6]=[C:5]5[C:10](=[CH:9][CH:8]=4)[N:2]([CH3:1])[N:3]=[CH:4]5)[C:12]3=[O:17])[S:20][C:21]=2[C:27]=1[C:28]1[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=1)[C:36]([O:38][CH3:39])=[O:37])([CH3:44])([CH3:42])[CH3:43]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 86699809Methyl (S)-2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-(tert-butoxy)acetateHCID 866998333-(1-methyl-1H-indazol-5-yl)pyridin-2(1H)-one

生成物 1

HCID 86699834(S)-methyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(3-(1-methyl-1H-indazol-5-yl)-2-oxopyridin-1(2H)-yl)benzo[d]thiazol-6-yl)acetate

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
110 °C

実験手順

To a solution of 3-(1-methyl-1H-indazol-5-yl)pyridin-2(1H)-one (13.0 mg, 0.055 mmol), (S)-methyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (22 mg, 0.046 mmol), trans-N1,N2-dimethylcyclohexane-1,2-diamine (9 μL, 0.055 mmol) and potassium carbonate (13 mg, 0.091 mmol) in DMF (0.5 mL) was added copper(I) iodide (5.0 mg, 0.026 mmol). The mixture was degassed with N2 for 5 minutes and then heated at 110° C. for 3 h. The mixture was then diluted with EtOAc, extracted with H2O, brine, dried over Na2SO4, filtered and concentrated and purified by flash column chromatography (silica gel, 0 to 100% ethyl acetate/hexanes) to give the product. LCMS-ESI+ (m/z): [M+H]+ calcd for C34H32ClN4O4S: 627.18; Found: 627.2.

後処理

  1. customThe mixture was degassed with N2 for 5 minutes
  2. additionThe mixture was then diluted with EtOAc
  3. extractionextracted with H2O, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash column chromatography (silica gel, 0 to 100% ethyl acetate/hexanes)
  8. customto give the product

出典と根拠

ORDレコード
ord-44dec4cc840f4390810caad78338b731
出典データセット
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08987250B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート