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Sulfamide → Phenyl-1,3-dihydro-2-thia-1,3,9-triaza-cyclopenta[a]naphthalene 2,2-dioxide

HRID 513810
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HRID 513810 반응식
[S:1](N)(N)(=[O:3])=[O:2].[C:6]1([NH:12][C:13]2[C:22]([NH2:23])=[C:21]3[C:16](C=CC=N3)=[CH:15][CH:14]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>N1C=CC=CC=1>[C:6]1([N:12]2[C:13]3=[C:14]4[C:15](=[CH:16][CH:21]=[C:22]3[NH:23][S:1]2(=[O:3])=[O:2])[CH:8]=[CH:7][CH:6]=[N:12]4)[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1
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참가 물질

4

반응물 2

HCID 82267SulfamideHCID 131733285N*7*-Phenyl-quinoline-7,8-diamine

생성물 1

HCID 68183426Phenyl-1,3-dihydro-2-thia-1,3,9-triaza-cyclopenta[a]naphthalene 2,2-dioxide수율 36%

시약·촉매·용매 1

HCID 1049Pyridine용매

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온도
115 °C

실험 절차

Sulfamide (34 mg, 0.35 mmol) was added to a solution of N*7*-phenyl-quinoline-7,8-diamine 576 (56 mg, 0.23 mmol) in pyridine (2 ml) and the mixture was heated in a microwave at 115° C. for 2 h. After cooling, the solvent was removed in vacuo. The residue was dissolved in EtOAc (50 ml) and the organic phase was washed with sat. NaHCO3 solution (30 ml), dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by column chromatography DCM/MeOH/TEA (98:2:0.5-90:10:0.5 gradient) followed by preparative HPLC (acidic conditions 1) to give the title compound (12.3 mg, 17%).

후처리

  1. temperatureAfter cooling
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in EtOAc (50 ml)
  4. washthe organic phase was washed with sat. NaHCO3 solution (30 ml)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by column chromatography DCM/MeOH/TEA (98:2:0.5-90:10:0.5 gradient)

출처 및 근거

ORD 기록
ord-23ff1a25bec241e8a2fca1b5e5e9c09b
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09102688B2

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