Ethylene Glycol → HCID 131726733, compound

HRID 971145Notes

Reaction equation

HRID 971145 reaction equation
[CH3:1][O:2][C:3](=[O:35])[C:4]([C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][C:16]3[C:19]([S:30]([CH3:33])(=[O:32])=[O:31])=[N:20][N:21]([C:22]4[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=4)[C:15]=3[C:14]2=[O:34])=[CH:9][CH:8]=1)([CH3:6])[CH3:5].N.C(O)[CH2:38][OH:39]>>[OH:39][CH2:38][CH2:1][O:2][C:3](=[O:35])[C:4]([C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][C:16]3[C:19]([S:30]([CH3:33])(=[O:32])=[O:31])=[N:20][N:21]([C:22]4[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=4)[C:15]=3[C:14]2=[O:34])=[CH:9][CH:8]=1)([CH3:6])[CH3:5]

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 222AmmoniaHCID 69516820HCID 69516820, compound

Product 1

HCID 131726733HCID 131726733, compoundYield 33%

Conditions

Temperature
80 °C

Procedure

2-{4-[3-Methanesulfonyl-1-(4-methoxyphenyl)-7-oxo-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-6-yl]phenyl}-2-methylproprionic acid methyl ester (0.077 g, 0.15 mmol) was placed in a sealed tube containing 10% ammonia in ethylene glycol (3 mL) and heated 80° C. for 2 h. The reaction was cooled, quenched with H2O, extracted with EtOAc, and dried (MgSO4). Purification by chromatography on silica (1:1 hexanes/ethyl acetate) and then HPLC purification afforded 27 mg (33%) title compound. High Resolution Mass Spec (M+H)+ for C26H30N3O7S 528.1776.

Workup

  1. temperatureThe reaction was cooled
  2. customquenched with H2O
  3. extractionextracted with EtOAc
  4. dry with materialdried (MgSO4)
  5. customPurification by chromatography on silica (1:1 hexanes/ethyl acetate)
  6. customHPLC purification

Sources & evidence

ORD record
ord-a47f621a960c4d149338451d563cd542
Source dataset
uspto-grants-2007_12
Patent number
US07312214B2

Reaction notes

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