Sodium Thiosulfate → 2-[4-(1,4-Dioxa-7-aza-spiro[4.4]non-7-yl)-3-fluorophenyl]-6-methoxy-2H-isoquinolin-1-one

HRID 69482ノート

反応式

HRID 69482 の反応式
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O:23]1[C:27]2([CH2:31][CH2:30][N:29]([C:32]3[CH:37]=[CH:36][C:35]([NH:38][C:39](=[O:51])[C:40]4[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][C:41]=4[CH2:48][CH2:49]O)=[CH:34][C:33]=3[F:52])[CH2:28]2)[O:26][CH2:25][CH2:24]1.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[O:26]1[C:27]2([CH2:31][CH2:30][N:29]([C:32]3[CH:37]=[CH:36][C:35]([N:38]4[CH:49]=[CH:48][C:41]5[C:40](=[CH:45][CH:44]=[C:43]([O:46][CH3:47])[CH:42]=5)[C:39]4=[O:51])=[CH:34][C:33]=3[F:52])[CH2:28]2)[O:23][CH2:24][CH2:25]1

参加物

5

反応物 3

HCID 24477Sodium ThiosulfateHCID 159087Triacetoxyperiodinane2 回HCID 68989883N-[4-(1,4-dioxa-7-aza-spiro[4.4]non-7-yl)-3-fluorophenyl]-2-(2-hydroxyethyl)-4-methoxy-benzamide

生成物 1

HCID 689902272-[4-(1,4-Dioxa-7-aza-spiro[4.4]non-7-yl)-3-fluorophenyl]-6-methoxy-2H-isoquinolin-1-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Dess-Martin periodinane (7 g) was added to a solution of N-[4-(1,4-dioxa-7-aza-spiro[4.4]non-7-yl)-3-fluorophenyl]-2-(2-hydroxyethyl)-4-methoxy-benzamide (4.6 g) in methylene chloride (279 mL). The reaction mixture was stirred for 2 h at room temperature, then further Dess-Martin periodinane (1.4 g) was added, stirring for a further 4 h at room temperature. Then 5% Na2S2O3 solution was added to the reaction solution and the organic phase was then washed with water. The methylene chloride phase was dried over sodium sulfate and the solvent was removed in vacuum. The raw product was purified by preparative HPLC. In this way the product was obtained with molecular weight 396.15 (C22H21FN2O4); MS (ESI): 397 (M+H+).

後処理

  1. stirringstirring for a further 4 h at room temperature
  2. washthe organic phase was then washed with water
  3. dry with materialThe methylene chloride phase was dried over sodium sulfate
  4. customthe solvent was removed in vacuum
  5. customThe raw product was purified by preparative HPLC
  6. customIn this way the product was obtained with molecular weight 396.15 (C22H21FN2O4)

出典と根拠

ORDレコード
ord-aa94c331bfbc44178c5186fc0abceb12
出典データセット
uspto-grants-2014_09
特許番号
US08822495B2

反応ノート

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