1,2-Dichloroethane → 2-(Benzenesulfonyl-pyridin-2-yl-amino)-N-[3-(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-cyclohexyl]-acetamide

HRID 352251ノート

反応式

HRID 352251 の反応式
I.[NH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH:5]([N:9]2[C:18]3[CH:17]=[CH:16][CH:15]=[C:14]([Cl:19])[C:13]=3[C:12]3=[N:20][O:21][C:22]([CH3:23])=[C:11]3[C:10]2=[O:24])[CH2:4]1.[C:25]1([S:31]([N:34]([CH2:41][C:42](O)=[O:43])[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=2)(=[O:33])=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.ON1C2N=CC=CC=2N=N1.C(Cl)CCl>CN(C=O)C.CN(C1C=CN=CC=1)C>[C:25]1([S:31]([N:34]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=2)[CH2:41][C:42]([NH:2][CH:3]2[CH2:8][CH2:7][CH2:6][CH:5]([N:9]3[C:18]4[CH:17]=[CH:16][CH:15]=[C:14]([Cl:19])[C:13]=4[C:12]4=[N:20][O:21][C:22]([CH3:23])=[C:11]4[C:10]3=[O:24])[CH2:4]2)=[O:43])(=[O:33])=[O:32])[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

参加物

7

反応物 4

HCID 111,2-DichloroethaneHCID 181649HOAtHCID 14721802-[(Phenylsulfonyl)(2-pyridinyl)amino]acetic acidHCID 227137135-(3-Aminocyclohexyl)-9-chloro-3-methyl-5H-isoxazolo[4,3-c]quinolin-4-one hydroiodide

生成物 1

HCID 227141272-(Benzenesulfonyl-pyridin-2-yl-amino)-N-[3-(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-cyclohexyl]-acetamide収率 47%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 5-(3-amino-cyclohexyl)-9-chloro-3-methyl-5H-isoxazolo[4,3-c]quinolin-4-one hydroiodide, 130 mg (0.28 mmol) in 10 mL of DMF was added 82 mg (0.28 mmol) of (benzenesulfonyl-pyridin-2-yl-amino)-acetic acid (Bionet), 46 mg (0.34 mmol) of 1-hydroxy-7-azabenzo-triazole, 66 mg (0.34 mmol) of EDC, 5 mg of DMAP and 120 μL (0.84 mmol) of TEA. The reaction mixture was stirred six days at rt. and was concentrated to dryness. The residue was dissolved in 20% isopropanol/chloroform, washed with saturated NaHCO3, washed with brine, dried over Na2SO4, filtered and concentrated to dryness. The residue was purified by radial chromatography using a MeOH/chloroform gradient and concentrated to dryness. The residue was slurried in ether/hexanes and concentrated to dryness to yield 79 mg (47%) of the title compound as a tan foam. MS (ion spray) 606.1 (M+).

後処理

  1. concentrationand was concentrated to dryness
  2. dissolutionThe residue was dissolved in 20% isopropanol/chloroform
  3. washwashed with saturated NaHCO3
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe residue was purified by radial chromatography
  9. concentrationconcentrated to dryness
  10. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-7ec032b0875642e993cfe32909e3ce70
出典データセット
uspto-grants-2004_06
特許番号
US06743794B2

反応ノート

読み込み中…