Lithium Hydroxide → 7-(3-(Pyridin-4-yl)-2-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoic acid

HRID 406231Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[N:12]=[C:11]3[N:13]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25]CC)=[O:24])[CH2:14][CH2:15][CH2:16][C:10]3=[N:9][C:8]=2[C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=2)=[CH:3][CH:2]=1.[Li+].[OH-]>C1COCC1.O>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[N:12]=[C:11]3[N:13]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[CH2:14][CH2:15][CH2:16][C:10]3=[N:9][C:8]=2[C:28]2[CH:29]=[CH:30][C:31]([CH3:34])=[CH:32][CH:33]=2)=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of ethyl 7-(3-(pyridin-4-yl)-2-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate (step 2) (15 mg, 0.033 mmol) in THF (2 ml) and water (1 ml) was treated with LiOH (7.83 mg, 0.327 mmol) and stirred at 70° C. for 4 hours. The mixture was cooled to room temperature and concentrated under vacuum. The residue was acidified (1N HCl, pH ˜5) and extracted with DCM (×3). The combined extracts were washed with brine, dried (MgSO4) and evaporated under vacuum to a yellow gum which was triturated with ether and dried under vacuum at 40° C. for 2.5 hours to afford the title compound;

Workup

temperatureThe mixture was cooled to room temperature
concentrationconcentrated under vacuum
extractionextracted with DCM (×3)
washThe combined extracts were washed with brine
dry with materialdried (MgSO4)
customevaporated under vacuum to a yellow gum which
customwas triturated with ether
customdried under vacuum at 40° C. for 2.5 hours

Sources & evidence

ORD record: ord-e15cecb6228545439072aa931432d9fa
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754085B2

Reaction notes

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