Sodium Hydroxide → 7-(6-oxo-2,3-dip-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoic acid

HRID 517882Notes

Reaction equation

[O:1]=[C:2]1[N:25]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34]CC)=[O:33])[C:6]2=[N:7][C:8]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=3)=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=3)[N:10]=[C:5]2[CH2:4][CH2:3]1.[OH-].[Na+]>CO>[O:1]=[C:2]1[N:25]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([OH:34])=[O:33])[C:6]2=[N:7][C:8]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=3)=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=3)[N:10]=[C:5]2[CH2:4][CH2:3]1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of ethyl 7-(6-oxo-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate (step 1) (2.0 g, 4.12 mmol) in MeOH (40 ml) was treated with 1M sodium hydroxide (12.36 ml, 12.36 mmol) and the resulting solution was stirred at 50° C. for 1 hour. The solution was allowed to cool to room temperature and concentrated under reduced pressure. The residue was diluted with water, acidified (pH ˜2 with 1N HCl) and the resulting suspension was extracted with DCM (×3). The combined organic extracts were dried (MgSO4) and evaporated under reduced pressure to afford the titled compound as a white solid;

Workup

temperatureto cool to room temperature
concentrationconcentrated under reduced pressure
additionThe residue was diluted with water
extractionthe resulting suspension was extracted with DCM (×3)
dry with materialThe combined organic extracts were dried (MgSO4)
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-8dce60a25f2d426187ec61d45fbec02d
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115129B2

Reaction notes

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