Hydrochloric Acid → 4-(2-(3,5-Dimethoxyphenethyl)-5H-pyrrolo[2,3-b]pyrazin-6-yl)picolinic acid

HRID 1052294Notes

Reaction equation

[OH-:1].[K+].[OH2:3].[CH3:4][O:5][C:6]1[CH:7]=[C:8]([CH2:14][CH2:15][C:16]2[N:17]=[C:18]3[CH:24]=[C:23]([C:25]4[CH:30]=[CH:29][N:28]=[C:27]([C:31]#N)[CH:26]=4)[N:22](S(C4C=CC=CC=4)(=O)=O)[C:19]3=[N:20][CH:21]=2)[CH:9]=[C:10]([O:12][CH3:13])[CH:11]=1.Cl>C1COCC1>[CH3:13][O:12][C:10]1[CH:9]=[C:8]([CH:7]=[C:6]([O:5][CH3:4])[CH:11]=1)[CH2:14][CH2:15][C:16]1[N:17]=[C:18]2[CH:24]=[C:23]([C:25]3[CH:30]=[CH:29][N:28]=[C:27]([C:31]([OH:3])=[O:1])[CH:26]=3)[NH:22][C:19]2=[N:20][CH:21]=1

Participants

Conditions

Temperature: 90 °C

Procedure

6.0 M Potassium hydroxide in water (0.2 mL, 1 mmol) was added to a solution of 4-[2-[2-(3,5-dimethoxyphenyl)ethyl]-5-(phenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazin-6-yl]pyridine-2-carbonitrile (50.0 mg, 0.0951 mmol) in THF (0.5 mL) and then the reaction was stirred at 90° C. for 5 hours. The mixture was then acidified to pH=2 by adding conc. HCl and then the solvent was removed to provide the desired crude product which was used in the next step directly. LCMS calculated for C22H21N4O4(M+H)+: m/z=405.2. Found 405.2.

Workup

customthe solvent was removed

Sources & evidence

ORD record: ord-3badbe06acf04809b99a9dca9afc8101
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388185B2

Reaction notes

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