Trifluoroacetic acid → Trifluoroacetic acid

HRID 853681Notes

Reaction equation

HRID 853681 reaction equation
[CH2:1]([O:3][C:4](=[O:47])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[C:20]3[CH2:21][N:22]([CH2:25][C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=4)[C:23](=[O:24])[C:19]=3[C:18]([O:33]C(C3C=CC=CC=3)C3C=CC=CC=3)=[C:17]3[C:12]=2[CH:13]=[CH:14][CH:15]=[N:16]3)[CH:6]=1)[CH3:2].[F:48][C:49]([F:54])([F:53])[C:50]([OH:52])=[O:51].C([SiH](CC)CC)C>ClCCl>[CH2:1]([O:3][C:4](=[O:47])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[C:20]3[CH2:21][N:22]([CH2:25][C:26]4[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=4)[C:23](=[O:24])[C:19]=3[C:18]([OH:33])=[C:17]3[C:12]=2[CH:13]=[CH:14][CH:15]=[N:16]3)[CH:6]=1)[CH3:2].[C:50]([OH:52])([C:49]([F:54])([F:53])[F:48])=[O:51]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 58929047HCID 58929047, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 44414030HCID 44414030, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 277 dissolved in dichloromethane (2 mL) was added trifluoroacetic acid (200 μl) and triethylsilane (400 μl). The reaction mixture was stirred at room temperature for ½ hours under an inert atmosphere then concentrated in vacuo. The residue was redissolved in DMSO (1 mL) and purified by prep-HPLC to afford 3-[7-(4-fluoro-benzyl)-9-hydroxy-8-oxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinolin-5-yl]-benzoic acid ethyl ester 278, TFA salt, (25 mg, 0.003 mmol, 44% in two steps) as a yellow solid: 1H NMR (CDCl3) δ 9.0 (d, 1H), 8.2 (d, 1H), 8.0 (s, 1H), 7.7 (m, 1H), 7.6 (dd, 1H), 7.5 (dd, 2H), 7.0 (m, 2H), 7.1 (t, 2H), 4.7 (dd, 2H), 4.4(q, 2H), 4.3 (dd, 2H), 1.4 (t, 3H); MS: 457 (M+1). HPLC conditions: mobile phase A was 0.1% TFA in water, mobile phase b was 0.1% TFA in CH3CN; gradient from 5% to 60% B in 20 min; flow rate was 20 mL/min; column was Phenomenex, luna 5μ, C18 (2), 150 mm×21.1 mm.

Workup

  1. concentrationthen concentrated in vacuo
  2. dissolutionThe residue was redissolved in DMSO (1 mL)
  3. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-a149a122f85348b4a79305c34042f45a
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

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