Pyridine → 3-(Acetylamino)-4-(2-methylpiperidin-1-yl)benzoic acid

HRID 219819Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[CH3:17])[C:5]([OH:7])=[O:6].N1C=CC=CC=1.[C:24](Cl)(=[O:26])[CH3:25]>C(Cl)Cl>[C:24]([NH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[CH3:17])[C:5]([OH:7])=[O:6])(=[O:26])[CH3:25]

Participants

Conditions

Temperature: 40 °C

Procedure

To a suspension of 3-amino-4-(2-methylpiperidin-1-yl)benzoic acid obtained in step 2 (100 mg; 0.43 mmol) in pyridine (69.04 μL, 0.85 mmol) and DCM (4 mL), was added acetyl chloride (36.42 μL; 0.51 mmol). The reaction mixture was then stirred at 40° C. for 5 h after which solvents were evaporated under vacuum, solid residue was triturated with ethylacetate and re-evaporated. Finally, water was added to the reaction mixture which was sonicated, filtered, dried under vacuum to give the title compound as a white solid (95 mg, 81%). 1H NMR (DMSO-d6, 300 MHz) δ 12.76 (bs, 1H), 8.97 (s, 1H), 8.66 (s, 1H), 7.64 (dd, J=8.2, 2.1 Hz, 1H), 7.29 (d, J=8.2 Hz, 1H), 3.07-3.01 (m, 1H), 2.86-2.82 (m, 1H), 2.57-2.51 (m, 1H), 2.15 (s, 3H), 1.82-1.77 (m, 4H), 1.47-1.42 (m, 2H), 0.78 (d, J=6 Hz, 3H). LC/MS (Method B): 277.2 (M+H)+. HPLC (Method A) Rt 1.77 min (purity: 91.3%).

Workup

customwere evaporated under vacuum, solid residue
customwas triturated with ethylacetate
customre-evaporated
additionFinally, water was added to the reaction mixture which
customwas sonicated
filtrationfiltered
customdried under vacuum

Sources & evidence

ORD record: ord-01e54dffcdf14d99b68e602162c905cd
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202865B2

Reaction notes

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