Trifluoroacetic acid → HCID 53746879, compound

HRID 1418689Notes

Reaction equation

HRID 1418689 reaction equation
[CH3:1][C:2]1[C:3](=[O:34])[N:4]2[C:16](=[CH:17][C:18]=1[CH:19]([O:22][C:23](=[O:33])[CH2:24][NH:25]C(OC(C)(C)C)=O)[CH2:20][CH3:21])[C:7]1=[N:8][C:9]3[C:14]([CH:15]=[C:6]1[CH2:5]2)=[CH:13][CH:12]=[CH:11][CH:10]=3.FC(F)(F)C(O)=O>COC1C=CC=C(OC)C=1>[NH2:25][CH2:24][C:23]([O:22][CH:19]([C:18]1[CH:17]=[C:16]2[N:4]([CH2:5][C:6]3[C:7]2=[N:8][C:9]2[C:14]([CH:15]=3)=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:3](=[O:34])[C:2]=1[CH3:1])[CH2:20][CH3:21])=[O:33]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67874079HCID 67874079, compound

Product 1

HCID 53746879HCID 53746879, compound

Reagents, catalysts & solvents 1

HCID 90251,3-DimethoxybenzeneSolvent

Procedure

To a stirring suspension of (±)-8-methyl-7-[1-[[[[(1,1-dimethylethoxy)carbonyl]amino]acetyl]oxy]propyl]indolizino[1,2-b]quinolin-9(11H)-one (1.15 g, 2.5 mmol) in 1,3-dimethoxybenzene (12 mL) under an argon atmosphere was added trifluoroacetic acid (13 mL). After stirring for 1.5 h at room temperature, the mixture was concentrated under reduced pressure. The residue was dissolved in H2O, extracted with Et2O, filtered and lyophilized to afford the title compound as a pale yellow solid. 1H NMR (DMSO-d6) d 8.68 (s, 1H), 8.24 (m, 1H), 8.13 (m, 1H), 7.86 (apparent br t, 1H), 7.70 (apparent br t, 1H), 7.19 (s, 1H), 5.91 (apparent br t, 1H), 5.26 (s, 2H), 4.02 (br s, 2H), 2.25 (s, 3H), 2.06-1.81 (m, 2H), 0.96 (t, J=7.2Hz, 3H). Anal. Calcd for C21H21N3O3.CF3CO2H.9/4 H2O; C, 53.33; H, 5.16; N, 8.11. Found: C, 53.09; H, 4.91; N, 7.74.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in H2O
  3. extractionextracted with Et2O
  4. filtrationfiltered

Sources & evidence

ORD record
ord-f807f567faad409baae8bb84704fc0cf
Source dataset
uspto-grants-1999_03
Patent number
US05883255

Reaction notes

Loading…