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Cesium carbonate → ditert-butyl [(2Z)-2-[4-[4-chloro-2-(2-methylpyrazol-3-yl)phenoxy]-3-cyanophenyl]sulfonylimino-1,3-thiazol-3-yl]methyl phosphate

HRID 1401943
ノート
印刷プレビュー

反応式

HRID 1401943 の反応式
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([S:13]([NH:16][C:17]3[S:18][CH:19]=[CH:20][N:21]=3)(=[O:15])=[O:14])=[CH:9][C:8]=2[C:22]#[N:23])=[C:4]([C:26]2[N:30]([CH3:31])[N:29]=[CH:28][CH:27]=2)[CH:3]=1.[P:32]([O:44][CH2:45]Cl)([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[P:32]([O:44][CH2:45][N:21]1[CH:20]=[CH:19][S:18]/[C:17]/1=[N:16]\[S:13]([C:10]1[CH:11]=[CH:12][C:7]([O:6][C:5]2[CH:24]=[CH:25][C:2]([Cl:1])=[CH:3][C:4]=2[C:26]2[N:30]([CH3:31])[N:29]=[CH:28][CH:27]=2)=[C:8]([C:22]#[N:23])[CH:9]=1)(=[O:14])=[O:15])([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])([O:39][C:40]([CH3:41])([CH3:42])[CH3:43])=[O:33]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 11701630Di-tert-butyl (chloromethyl) phosphateHCID 594365994-[4-Chloro-2-(1-methyl-1H-pyrazol-5-yl)phenoxy]-3-cyano-N-1,3-thiazol-2-ylbenzenesulfonamide

生成物 1

HCID 59436487ditert-butyl [(2Z)-2-[4-[4-chloro-2-(2-methylpyrazol-3-yl)phenoxy]-3-cyanophenyl]sulfonylimino-1,3-thiazol-3-yl]methyl phosphate収率 84.9%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

4-[4-Chloro-2-(1-methyl-1H-pyrazol-5-yl)phenoxy]-3-cyano-N-1,3-thiazol-2-ylbenzenesulfonamide, (Example 170, 200 mg, 0.000424 mol), di-tert-butyl chloromethyl phosphate (J. Med. Chem. 51 (2008) p1111-1114, supplementary data) (160 mg, 0.000619 mol) and cesium carbonate (420 mg, 0.00129 mol) were stirred in dimethylformamide (2 mL) at 60° C. for 18 hours. The mixture was cooled then partitioned between tert-butylmethyl ether (80 mL) and water (40 mL), the organic layer was dried over anhydrous sodium sulphate, filtered and the solvent removed in vacuo to give the title compound as a pale yellow gum, (250 mg).

後処理

  1. temperatureThe mixture was cooled
  2. customthen partitioned between tert-butylmethyl ether (80 mL) and water (40 mL)
  3. dry with materialthe organic layer was dried over anhydrous sodium sulphate
  4. filtrationfiltered
  5. customthe solvent removed in vacuo

出典と根拠

ORDレコード
ord-631928307d6c40cb87d8bc3ac118ca7a
出典データセット
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08907101B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート