Sodium Hydroxide → 6-(2,3-Di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)hexanoic acid

HRID 517899Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of ethyl 6-(2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)hexanoate (step 1)(2.8 g, 6.12 mmol) in MeOH (50 ml) was treated with 1M sodium hydroxide (9.18 ml, 18.36 mmol) and the resulting white suspension was heated at 50° C. for 2 hours. The mixture was allowed to cool to room temperature and concentrated under reduced pressure. The residue was diluted with water, acidified (pH 4, 2N HCl) and extracted with DCM (×3). The combined organic extracts were dried (MgSO4) and concentrated under reduced pressure to afford an oil which crystallized to yield the titled compound as an off-white solid;

Workup

temperatureto cool to room temperature
concentrationconcentrated under reduced pressure
additionThe residue was diluted with water
extractionextracted with DCM (×3)
dry with materialThe combined organic extracts were dried (MgSO4)
concentrationconcentrated under reduced pressure
customto afford an oil which
customcrystallized

Sources & evidence

ORD record: ord-13545f872721442d8e4513308968022a
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115129B2

Reaction notes

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