Glycerol → HCID 67042291, compound

HRID 1402507Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[NH:9][C:10]([NH:12][C:13]1[CH:42]=[CH:41][C:16]([O:17][C:18]2[CH:23]=[CH:22][N:21]=[C:20]([C:24]3[NH:28][CH:27]=[C:26]([C:29]([NH:31][CH:32]([CH2:36][CH2:37][C:38]([OH:40])=[O:39])[C:33]([OH:35])=[O:34])=[O:30])[CH:25]=3)[CH:19]=2)=[CH:15][CH:14]=1)=[O:11].O[CH2:44][CH:45]([CH2:47][OH:48])[OH:46]>CN(C)C1C=CN=CC=1.C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[NH:9][C:10]([NH:12][C:13]1[CH:14]=[CH:15][C:16]([O:17][C:18]2[CH:23]=[CH:22][N:21]=[C:20]([C:24]3[NH:28][CH:27]=[C:26]([C:29]([NH:31][CH:32]([CH2:36][CH2:37][C:38]([O:40][CH2:44][CH:45]([OH:46])[CH2:47][OH:48])=[O:39])[C:33]([O:35][CH2:44][CH:45]([OH:46])[CH2:47][OH:48])=[O:34])=[O:30])[CH:25]=3)[CH:19]=2)=[CH:41][CH:42]=1)=[O:11]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 2-{[(5-{4-[4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenoxy]pyridin-2-yl}-1H-pyrrol-3-yl)carbonyl]amino}pentanedioic acid (60 mg, 0.10 mmol), glycerol (0.5 ml), 1-Ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride (EDC.HCl, 37 mg, 0.19 mmol) and 4-dimethylaminopyridine (DMAP, 5 mg, 0.04 mmol) in anhydrous THF (10 ml) was stirred at 60° C. for 3 hours. The mixture was cooled to room temperature, concentrated and purified by silica gel chromatography eluting with a gradient of 10˜15% MeOH/CHCl3 to give bis(2,3-dihydroxypropyl) 2-{[(5-{-4-[4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenoxy]pyridin-2-yl}-1H-pyrrol-3-yl)carbonyl]amino}pentanedioate as colorless oil. Yield: 40 mg, 53%.

Workup

temperatureThe mixture was cooled to room temperature
concentrationconcentrated
custompurified by silica gel chromatography
washeluting with a gradient of 10˜15% MeOH/CHCl3

Sources & evidence

ORD record: ord-3ce9459a487f4eda945274ec7e0ccb82
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906944B2

Reaction notes

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