Trifluoroacetic acid → Trifluoroacetic acid

HRID 853691Notes

Reaction equation

HRID 853691 reaction equation
C([O:14][C:15]1[C:16]2[C:35](=[O:36])[N:34]([CH2:37][C:38]3[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=3)[CH2:33][C:17]=2[C:18]([C:25]2[C:26]([O:31][CH3:32])=[N:27][CH:28]=[CH:29][CH:30]=2)=[C:19]2[C:24]=1[N:23]=[CH:22][CH:21]=[CH:20]2)(C1C=CC=CC=1)C1C=CC=CC=1.[F:45][C:46]([F:51])([F:50])[C:47]([OH:49])=[O:48].C([SiH](CC)CC)C>ClCCl>[F:44][C:41]1[CH:40]=[CH:39][C:38]([CH2:37][N:34]2[C:35](=[O:36])[C:16]3[C:15]([OH:14])=[C:24]4[C:19]([CH:20]=[CH:21][CH:22]=[N:23]4)=[C:18]([C:25]4[C:26]([O:31][CH3:32])=[N:27][CH:28]=[CH:29][CH:30]=4)[C:17]=3[CH2:33]2)=[CH:43][CH:42]=1.[C:47]([OH:49])([C:46]([F:51])([F:50])[F:45])=[O:48]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 58928663HCID 58928663, compound

Product 2

HCID 6422Trifluoroacetic acidYield 68%HCID 10024854HCID 10024854, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 288 (18 mg) dissolved in dichloromethane (1 mL) was added trifluoroacetic acid (100 μl) and triethylsilane (200 μl). The reaction mixture was stirred at room temperature for ½ hours under an inert atmosphere then concentrated in vacuo. The residue was purified by HPLC to afford 7-(4-fluoro-benzyl)-5-(2-methoxy-pyridin-3-yl)-9-hydroxy-6,7-dihydro-pyrrolo[3,4-g]quinolin-8-one 289, TFA salt, (11.6 mg, 68%) as a yellow solid: 1H NMR (CDCl3) δ 9.0 (d, 1H), 8.3 (d, 1H), 7.9 (d, 1H), 7.5 (m, 2H), 7.2 (m, 1H+1H), 7.0 (m, 2H+1H), 4.7 (dd, 2H), 4.1(dd, 2H), 3.8 (s, 1H); MS: 416 (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. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-c212f353a20b4b35a45a0897800c129a
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

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