Pentaerythritol → HCID 71293584, compound

HRID 1402585Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([NH:11][C:12]2[CH:32]=[CH:31][C:15]([O:16][C:17]3[CH:22]=[CH:21][N:20]=[C:19]([C:23]4[NH:27][CH:26]=[C:25]([C:28]([OH:30])=[O:29])[CH:24]=4)[CH:18]=3)=[CH:14][CH:13]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1.Cl.CN(C)CCCN=C=NCC.[OH:45][CH2:46][C:47]([CH2:52]O)([CH2:50][OH:51])[CH2:48][OH:49]>O1CCCC1.CN(C)C1C=CN=CC=1>[CH3:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([NH:11][C:12]2[CH:32]=[CH:31][C:15]([O:16][C:17]3[CH:22]=[CH:21][N:20]=[C:19]([C:23]4[NH:27][CH:26]=[C:25]([C:28]([O:30][CH2:52][C:47]([CH2:50][OH:51])([CH2:48][OH:49])[CH2:46][OH:45])=[O:29])[CH:24]=4)[CH:18]=3)=[CH:14][CH:13]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirred suspension of 5-{4-[4-({[(3-methylphenyl)amino]carbonyl}amino)phenoxy]pyridin-2-yl}-1H-pyrrole-3-carboxylic acid (150 mg, 0.35 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC, 102 mg, 0.53 mmol) in 10 ml of anhydrous tetrahydrofuran were added pentaerythritol (143 mg, 1.05 mmol) and 4-dimethylaminopyridine (10 mg, 0.08 mmol). The mixture was heated at 60° C. for 16 hours, cooled to room temperature and evaporated to dryness. The residue was purified by C-18 reverse phase chromatography eluting with a gradient of 10˜50% of acetonitrile in water to afford 3-hydroxy-2,2-bis(hydroxymethyl)propyl 5-{4-[4-({[(3-methylphenyl)amino]carbonyl}amino)phenoxy]pyridin-2-yl}-1H-pyrrole-3-carboxylate as white solid. Yield: 46 mg, 24%.

Workup

temperaturecooled to room temperature
customevaporated to dryness
customThe residue was purified by C-18 reverse phase chromatography
washeluting with a gradient of 10˜50% of acetonitrile in water

Sources & evidence

ORD record: ord-279054c8e2764306aa19157625285daa
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906944B2

Reaction notes

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