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Dimethyl Sulfoxide → [(S)-1-(2-Amino-9-fluoro-5-methyl-1,3-dioxo-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinazolin-8-yl)pyrrolidin-3-yl]carbamic acid tert-butyl ester

HRID 10335
ノート
印刷プレビュー

反応式

HRID 10335 の反応式
N[C:2]1([CH3:19])[N:13]2[C:14]3[C:9]([C:10](=[O:16])[NH:11][C:12]2=[O:15])=[CH:8][C:7]([F:17])=[C:6](F)[C:5]=3[CH2:4][CH2:3]1.[C:20]([O:24][C:25](=[O:32])[NH:26][C@H:27]1[CH2:31][CH2:30][NH:29][CH2:28]1)([CH3:23])([CH3:22])[CH3:21].C([N:35](CC)CC)C.CS(C)=O>O>[C:20]([O:24][C:25](=[O:32])[NH:26][C@H:27]1[CH2:31][CH2:30][N:29]([C:6]2[C:5]3[CH2:4][CH2:3][CH:2]([CH3:19])[N:13]4[C:14]=3[C:9]([C:10](=[O:16])[N:11]([NH2:35])[C:12]4=[O:15])=[CH:8][C:7]=2[F:17])[CH2:28]1)([CH3:23])([CH3:21])[CH3:22]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 1514396(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 219792245-amino-8,9-difluoro-5-methyl-6,7-dihydro-5H-pyrido[3,2,1-ij]quinazoline-1,3-dione

生成物 1

HCID 58681896[(S)-1-(2-Amino-9-fluoro-5-methyl-1,3-dioxo-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinazolin-8-yl)pyrrolidin-3-yl]carbamic acid tert-butyl ester
収率 71.8%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A solution of 0.12 g (0.45 mmol) of 5-amino-8,9-difluoro-5-methyl-6,7-dihydro-5H-pyrido[3,2,1-ij]quinazoline-1,3-dione (Example 24i), 0.34 g (1.8 mmol) of (S)-3-pyrrolidinylcarbamic acid tert-butyl ester (J. Med. Chem., 1992; 35:1764), 0.2 g (2.0 mmol) of triethylamine and 7 mL of dimethyl sulfoxide is heated at 110° C. for 18 hours. The reaction is cooled to room temperature, diluted with 80 mL of ice and water and stirred at 5° C. for 1 hour. The resulting precipitate is removed by filtration, washed with water and dried in vacuo. The solid is chromatographed over flash grade silica gel (230–400 mesh) eluting with dichloromethane/ethanol (9:1) to give 0.14 g of the title compound, mp 98–100° C.

後処理

  1. customThe resulting precipitate is removed by filtration
  2. washwashed with water
  3. customdried in vacuo
  4. customThe solid is chromatographed over flash grade silica gel (230–400 mesh)
  5. washeluting with dichloromethane/ethanol (9:1)

出典と根拠

ORDレコード
ord-7529c8caf4b748479316487eac532aa3
出典データセット
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07094780B1

反応ノート

読み込み中…

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