Water → 8-{2-(Tert-butyloxycarbonylaminosulfonyl)amino-ethoxy}-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

HRID 61722ノート

反応式

HRID 61722 の反応式
FC(F)(F)C(O)=O.[NH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]2[C:27](=[O:28])[C:26]3[C:25]4[C:20](=[CH:21][C:22]([C:29]#[N:30])=[CH:23][CH:24]=4)[NH:19][C:18]=3[C:17]([CH3:32])([CH3:31])[C:16]=2[CH:33]=1.[C:34]([O:38][C:39]([N-:41][S:42](N1C=CC(=[N+](C)C)C=C1)(=[O:44])=[O:43])=[O:40])([CH3:37])([CH3:36])[CH3:35].O>N1C=CC=CC=1>[C:34]([O:38][C:39]([NH:41][S:42]([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]2[C:27](=[O:28])[C:26]3[C:25]4[C:20](=[CH:21][C:22]([C:29]#[N:30])=[CH:23][CH:24]=4)[NH:19][C:18]=3[C:17]([CH3:31])([CH3:32])[C:16]=2[CH:33]=1)(=[O:44])=[O:43])=[O:40])([CH3:37])([CH3:35])[CH3:36]

参加物

6

反応物 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 668337928-(2-amino-ethoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrileHCID 178482962HCID 178482962、化合物

生成物 1

HCID 668341498-{2-(Tert-butyloxycarbonylaminosulfonyl)amino-ethoxy}-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile収率 69.8%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

Trifluoroacetic acid salt of 8-(2-amino-ethoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound A8-2, 20 mg, 0.044 mmol) was dissolved in pyridine (0.5 mL), added with N-(tert-butoxycarbonyl)-N-[4-(dimethyl azaniumylidene)-1,4-dihydropyridin-1-yl sulfonyl]azanide (13.5 mg, 1 eq.), and then stirred at room temperature for 14 hr. The reaction solution was added to water, and then extracted with ethyl acetate. After washing with saturated brine, the organic layer was dried over sodium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were separated by silica gel preparative TLC (ethyl acetate) to obtain the title compound (16.1 mg, 68%).

後処理

  1. extractionextracted with ethyl acetate
  2. washAfter washing with saturated brine
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. customThe drying agent was removed by filtration
  5. customthe residues obtained
  6. concentrationafter concentration under reduced pressure
  7. customwere separated by silica gel preparative TLC (ethyl acetate)

出典と根拠

ORDレコード
ord-c6834d34a236423aaa36409a16b1896e
出典データセット
uspto-grants-2016_09
特許番号
US09440922B2

反応ノート

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