Triethylamine → 2-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

HRID 853675Notes

Reaction equation

HRID 853675 reaction equation
C(N(CC)CC)C.[C:8]([NH:11][C:12]1[S:13][C:14]([S:18](Cl)(=[O:20])=[O:19])=[C:15]([CH3:17])[N:16]=1)(=[O:10])[CH3:9].[CH:22]([O:35][C:36]1[C:37]2[C:49](=[O:50])[N:48]([CH2:51][C:52]3[CH:57]=[CH:56][C:55]([F:58])=[CH:54][CH:53]=3)[CH2:47][C:38]=2[C:39]([OH:46])=[C:40]2[C:45]=1[N:44]=[CH:43][CH:42]=[CH:41]2)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CCOC(C)=O.CCCCCC>CN(C1C=CN=CC=1)C.CCOC(C)=O>[CH:22]([O:35][C:36]1[C:37]2[C:49](=[O:50])[N:48]([CH2:51][C:52]3[CH:57]=[CH:56][C:55]([F:58])=[CH:54][CH:53]=3)[CH2:47][C:38]=2[C:39]([O:46][S:18]([C:14]2[S:13][C:12]([NH:11][C:8](=[O:10])[CH3:9])=[N:16][C:15]=2[CH3:17])(=[O:19])=[O:20])=[C:40]2[C:45]=1[N:44]=[CH:43][CH:42]=[CH:41]2)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 969512-Acetamido-4-methylthiazole-5-sulfonyl chlorideHCID 21226206Ethyl acetate hexaneHCID 1361585899-Benzhydryloxy-7-(4-fluoro-benzyl)-5-hydroxy-6,7-dihydro-pyrrolo[3,4-g]quinolin-8-one

Product 1

HCID 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 esterYield 79%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (50 g), DMAP (catalytic amount) and 2-acetylamino-4-methyl-thiazole-5-sulfonyl chloride (25.5 mg, 0.10 mmol) were added to 0.034 mmol 45. The reaction mixture was stirred at room temperature for 18 hours under an inert atmosphere. The reaction was monitored by TLC (EtOAc/hexane 3/7) (Rf 44=0.5, Rf 45=0, Rf 272=0.2) and LC/MS. After completion of the reaction, the mixture was diluted with EtOAc (20 mL) and washed with 1N HCl, saturated NaHCO3 and brine. The organic phase was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (ethylacetate/hexane—3/7) to afford 2-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 272 (18.9 mg, 79%).

Workup

  1. customAfter completion of the reaction
  2. washwashed with 1N HCl, saturated NaHCO3 and brine
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography (ethylacetate/hexane—3/7)

Sources & evidence

ORD record
ord-3a4b66164e644dcb91ce1178134ad53c
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

Loading…