Hydrochloric Acid → 8,8-Dimethyl-6-(3-morpholin-4-yl-phenyl)-5,6,7,8-tetrahydro-[1,5]naphthyridine-2-carboxylic acid

HRID 2408131Notes

Reaction equation

[CH3:1][C:2]1([CH3:26])[C:11]2[N:10]=C(C#N)[CH:8]=[CH:7][C:6]=2[NH:5][CH:4]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[CH:15]=2)[CH2:3]1.[OH-:27].[Na+].Cl.[CH2:30]([OH:32])[CH3:31]>O>[CH3:1][C:2]1([CH3:26])[C:11]2[N:10]=[C:31]([C:30]([OH:27])=[O:32])[CH:8]=[CH:7][C:6]=2[NH:5][CH:4]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[CH:15]=2)[CH2:3]1

Participants

Conditions

Temperature: 90 °C

Procedure

To a stirred mixture solution of 8,8-dimethyl-6-(3-morpholin-4-yl-phenyl)-5,6,7,8-tetrahydro-[1,5]naphthyridine-2-carbonitrile (698.0 mg, 2.0 mmol) in ethanol (10.0 mL) was added 50% sodium hydroxide in water (8.5 mL). The reaction mixture was stirred at 90° C. for 6 h. The mixture was neutralized with a 3 N aqueous hydrochloric acid solution and extracted with ethyl acetate (2×100 mL), washed with water, dried over anhydrous sodium sulfate and then concentrated in vacuo to afford 8,8-dimethyl-6-(3-morpholin-4-yl-phenyl)-5,6,7,8-tetrahydro-[1,5]naphthyridine-2-carboxylic acid (660.6 mg, 90%) as a light white solid which was used for next step without further purification: MS (ESI) M+1=368.1.

Workup

extractionextracted with ethyl acetate (2×100 mL)
washwashed with water
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-9c4b2c6f3c614c4eb95dfb52712bf86a
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809369B2

Reaction notes

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