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

HRID 61722노트

반응식

HRID 61722 반응식
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]

참가 물질

6

반응물 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, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-c6834d34a236423aaa36409a16b1896e
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440922B2

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