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 853630Notes

Reaction equation

HRID 853630 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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].

Workup

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

Sources & evidence

ORD record
ord-e993cfc75f8b48bd883834d81b8a38f9
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

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