Hydrochloric Acid → 6-(3-Cyanopropyl)imidazo[1,2-a]pyridine-3-carboxylic acid

HRID 570303Notes

Reaction equation

[C:1]([CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([C:12]([C:15]([O:17]CC)=[O:16])=[CH:13][N:14]=2)[CH:11]=1)#[N:2].[Li+].[OH-].Cl>C1COCC1.CO>[C:1]([CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([C:12]([C:15]([OH:17])=[O:16])=[CH:13][N:14]=2)[CH:11]=1)#[N:2]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirring solution of ethyl 6-(3-cyanopropyl)imidazo[1,2-a]pyridine-3-carboxylate (24w) (375 mg, 1.46 mmol) in THF:MeOH (4:1, 5 mL) was added 2N LiOH (500 μL). The reaction was heated at 50° C. for 45 minutes then cooled to room temperature and the pH was adjusted between 3-4 with 1N HCl. The solvent was partially concentrated and the remaining aqueous was lyophilized to yield 6-(3-cyanopropyl)imidazo[1,2-a]pyridine-3-carboxylic acid (25). 1H NMR (400 MHz, d6-DMSO) δ 9.21-9.19 (m, 1 H), 8.45 (s, 1 H), 7.85 (dd, J=0.8, 9.2 Hz, 1 H), 7.70 (dd, J=1.6, 9.2 Hz, 1 H), 2.82 (t, J=7.2 Hz, 2 H), 2.55 (t, J=7.2 Hz, 2 H), 1.97-1.90 (m, 2 H). MS m/z 230.3 (M+1)+.

Workup

temperaturethen cooled to room temperature
concentrationThe solvent was partially concentrated

Sources & evidence

ORD record: ord-35d98c07fa7e412782a570258f210a4b
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023839B2

Reaction notes

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