Dimethylformamide → HCID 21995979、化合物

HRID 1978556ノート

反応式

HRID 1978556 の反応式
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]3[S:19](=[O:21])(=[O:20])[CH2:18][CH2:17][C:16]([C:22](O)=[O:23])=[CH:15][C:14]=3[CH:25]=2)=[CH:6][CH:5]=1)[CH3:2].C(Cl)(=O)C(Cl)=O.CN(C=O)C.[CH2:37]1[CH2:56][O:55][C:39]2([CH2:44][CH2:43][CH:42]([N:45]([CH2:47][C:48]3[CH:54]=[CH:53][C:51]([NH2:52])=[CH:50][CH:49]=3)[CH3:46])[CH2:41][CH2:40]2)[O:38]1>C1COCC1.O.C(N(CC)CC)C>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]3[S:19](=[O:20])(=[O:21])[CH2:18][CH2:17][C:16]([C:22]([NH:52][C:51]4[CH:50]=[CH:49][C:48]([CH2:47][N:45]([CH:42]5[CH2:41][CH2:40][C:39]6([O:38][CH2:37][CH2:56][O:55]6)[CH2:44][CH2:43]5)[CH3:46])=[CH:54][CH:53]=4)=[O:23])=[CH:15][C:14]=3[CH:25]=2)=[CH:6][CH:5]=1)[CH3:2]

参加物

8

反応物 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 10754953HCID 10754953、化合物HCID 219958687-(4-Ethoxyphenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid

生成物 1

HCID 21995979HCID 21995979、化合物収率 60.4%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8471Triethylamine溶媒

実験手順

To a solution of 7-(4-ethoxyphenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid (180 mg) in THF (10 ml) were added at room temperature oxalyl chloride (0.09 ml) and a drop of DMF, and the mixture was stirred for 1 hour. The mixture was concentrated under reduced pressure, and the residue was dissolved in THF (10 ml). The solution was added dropwise at 0° C. to a solution of 4-[N-(4,4-ethylenedioxycyclohexyl)-N-methylaminomethyl]aniline [0.153 g (0.553 mmol)] and triethylamine (0.14 ml) in THF (5 ml), and the mixture was stirred at room temperature for 16 hours. To the mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried with magnesium sulfate. The solvent was evaporated under reduced pressure to give crude crystals, which were recrystallized from ethanol/diisopropylether to give colorless crystals of 7-(4-ethoxyphenyl)-N-[4-[N-(4,4-ethylenedioxycyclohexyl)-N-methylaminomethyl]phenyl]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxamide (Compound 18) (187 mg).

後処理

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in THF (10 ml)
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried with magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customto give crude crystals, which
  8. customwere recrystallized from ethanol/diisopropylether

出典と根拠

ORDレコード
ord-dd7f3b3173e54fe0a01d39f61ae90d38
出典データセット
uspto-grants-2001_05
特許番号
US06235771B1

反応ノート

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