Trifluoroacetic acid → Trifluoroacetic acid

HRID 853676Notes

Reaction equation

HRID 853676 reaction equation
C([O:14][C:15]1[C:16]2[C:41](=[O:42])[N:40]([CH2:43][C:44]3[CH:49]=[CH:48][C:47]([F:50])=[CH:46][CH:45]=3)[CH2:39][C:17]=2[C:18]([O:25][S:26]([C:29]2[S:33][C:32]([NH:34][C:35](=[O:37])[CH3:36])=[N:31][C:30]=2[CH3:38])(=[O:28])=[O:27])=[C:19]2[C:24]=1[N:23]=[CH:22][CH:21]=[CH:20]2)(C1C=CC=CC=1)C1C=CC=CC=1.[F:51][C:52]([F:57])([F:56])[C:53]([OH:55])=[O:54].C([SiH](CC)CC)C>ClCCl>[F:50][C:47]1[CH:48]=[CH:49][C:44]([CH2:43][N:40]2[C:41](=[O:42])[C:16]3[C:15]([OH:14])=[C:24]4[C:19]([CH:20]=[CH:21][CH:22]=[N:23]4)=[C:18]([O:25][S:26]([C:29]4[S:33][C:32]([NH:34][C:35](=[O:37])[CH3:36])=[N:31][C:30]=4[CH3:38])(=[O:28])=[O:27])[C:17]=3[CH2:39]2)=[CH:45][CH:46]=1.[C:53]([OH:55])([C:52]([F:57])([F:56])[F:51])=[O:54]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 601076382-acetylamino-4-methyl-thiazole-5-sulfonic acid 9-benzhydryloxy-7-(4-fluoro-benzyl)-8-oxo-7,8-dihydro-6H-pyrrolo[3,4 g]quinolin-5-yl ester

Product 2

HCID 6422Trifluoroacetic acidYield 74%HCID 104373422-acetylamino-4-methyl-thiazole-5-sulfonic acid 7-(4-fluoro-benzyl)-9-hydroxy-8-oxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinolin-5-yl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 272 (18.9 mg, 0.027 mmol) 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 triturated with diethyl ether/hexane (1/1) to afford 2-acetylamino-4-methyl-thiazole-5-sulfonic acid 7-(4-fluoro-benzyl)-9-hydroxy-8-oxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinolin-5-yl ester 273, TFA salt, (13.2 mg, 74%) as a yellow solid: 1H NMR (CD3OD) δ 8.9 (d, 1H), 8.2 (d, 1H), 7.6 (m, 1H), 7.4 (m, 2H), 7.1 (t, 2H), 4.7 (s, 2H), 4.4 (s, 2H), 2.23 (s, 3H), 2.21 (s, 3H); MS: 543 (M+1).

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe residue was triturated with diethyl ether/hexane (1/1)

Sources & evidence

ORD record
ord-c10bfbf284d14d429811b150598697b4
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

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