Water → HCID 9826054, compound

HRID 1956772Notes

Reaction equation

[CH2:1]([C:5]1[N:6]([CH2:13][C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[N:20]=[C:19]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]([OH:32])=[O:31])[CH:18]=[C:17]3C(O)=O)[C:7]([CH2:11][OH:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4].S(=O)(=O)(O)O.O.C(=O)([O-])[O-].[Na+].[Na+]>N1C2C(=CC=CC=2)C=CC=1>[CH2:1]([C:5]1[N:6]([CH2:13][C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[N:20]=[C:19]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]([OH:32])=[O:31])[CH:18]=[CH:17]3)[C:7]([CH2:11][OH:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 170 °C

Procedure

In 10 ml of quinoline were dissolved 44.2 mg of the 6-[(2-butyl-4-chloro-5-hydroxymethyl-1H-imidazol-1-yl)methyl]-2-(2-carboxyphenyl)-4-quinolinecarboxylic acid obtained in Example 9. After adding 100 mg of conc. sulfuric acid, the mixture was heated at 170° C. for 1 hour. Then the reaction mixture was poured into water, made alkaline by adding sodium carbonate and washed with toluene. The aqueous layer was neutralized with 3M hydrochloric acid until a precipitate was formed. Then the precipitate was collected by filtration and purified by flash chromatography on silica gel with the use of chloroform/methanol. Thus 25 mg of 2-{6-[(2-butyl-4-chloro-5-hydroxymethyl-1H-imidazol-1-yl)methyl]quinolin-2-yl}benzoic acid were obtained. NMR (270 MHz, CDCl3): δ 7.2-8.2 (m,9H); 5.4 (s,2H); 4.5 (s,2H); 2.6 (t,J=8Hz,2H); 1.2-1.8 (m,4H); 1.4 (m,2H); 0.8 (t,J=8Hz,3H).

Workup

washwashed with toluene
customwas formed
filtrationThen the precipitate was collected by filtration
custompurified by flash chromatography on silica gel with the use of chloroform/methanol

Sources & evidence

ORD record: ord-c9b96e061be64d1ea18a209b2cb71e0c
Source dataset: uspto-grants-1998_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05780634

Reaction notes

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