Trifluoroacetic acid → methyl 3-[[7-[(4-fluorophenyl)methyl]-9-hydroxy-5-methoxy-8-oxo-6H-pyrrolo[3,4-g]quinolin-6-yl]sulfanyl]propanoate

HRID 853630ノート

反応式

HRID 853630 の反応式
[F:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[C:19](=[O:20])[C:18]3[C:17]([OH:21])=[C:16]4[C:11]([CH:12]=[CH:13][CH:14]=[N:15]4)=[C:10]([O:22][CH3:23])[C:9]=3[CH:8]2O)=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O.[CH3:34][O:35][C:36](=[O:40])[CH2:37][CH2:38][SH:39]>C(Cl)Cl>[CH3:34][O:35][C:36](=[O:40])[CH2:37][CH2:38][S:39][CH:8]1[C:9]2[C:10]([O:22][CH3:23])=[C:11]3[C:16](=[C:17]([OH:21])[C:18]=2[C:19](=[O:20])[N:7]1[CH2:6][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:26][CH:25]=1)[N:15]=[CH:14][CH:13]=[CH:12]3

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 18050Methyl 3-mercaptopropionateHCID 103834717-[(4-fluorophenyl)methyl]-6,9-dihydroxy-5-methoxy-6H-pyrrolo[3,4-g]quinolin-8-one

生成物 1

HCID 10479199methyl 3-[[7-[(4-fluorophenyl)methyl]-9-hydroxy-5-methoxy-8-oxo-6H-pyrrolo[3,4-g]quinolin-6-yl]sulfanyl]propanoate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 20 (215 mg, 0.422 mmol) in CH2Cl2 (4.2 mL) and TFA (98 μL, 1.26 mmol) was added methyl-3-mercaptopropionate (56 μL, 0.506 mmol). The solution was stirred at ambient temperature for 5 hours when LCMS analysis indicated complete conversion of the starting materials to the products. The solution was dried under reduced pressure and azeotroped with CH2Cl2 three times to provide the product 23 as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 2.30-2.38 (m, 4H), 3.63 (s, 3H), 4.04 (s, 3H),4.42 (d, 1H, J=15 Hz), 5.33 (d, 1H, J=15 Hz), 5.49 (s, 1H), 7.05 (t, 2H, J=9 Hz), 7.38 (dd, 2H, J=5, 8 Hz), 7.59 (dd, 1H, J=4,9 Hz), 8.53 (d, 1H, J=8 Hz), 8.91-9.01 (m, 1H); 19F NMR (282.6 MHz, CDCl3) δ 62.6; EI MS (m/z) 457.3 [MH+], 479.2 [M+Na].

後処理

  1. customThe solution was dried under reduced pressure
  2. customazeotroped with CH2Cl2 three times

出典と根拠

ORDレコード
ord-e993cfc75f8b48bd883834d81b8a38f9
出典データセット
uspto-grants-2007_08
特許番号
US07253180B2

反応ノート

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