Hydrochloric Acid → HCID 71281193, compound

HRID 1497895Notes

Reaction equation

HRID 1497895 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]3[N:14]([C:16]([C:19]([O:21]C)=[O:20])=[CH:17][N:18]=3)[CH:15]=2)[CH2:4][CH2:3]1.[Li+].[OH-].Cl>C1COCC1.CO>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]3[N:14]([C:16]([C:19]([OH:21])=[O:20])=[CH:17][N:18]=3)[CH:15]=2)[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 71281048HCID 71281048, compound

Product 1

HCID 71281193HCID 71281193, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a stirring solution of methyl 6-(2-(4-methylpiperazin-1-yl)ethyl)imidazo[1,2-a]pyridine-3-carboxylate (113) (215 mg, 0.68 mmol) in THF:MeOH (4:1, 4 mL) was added 2N LiOH (3 mL). The reaction was heated at 60° C. for 45 minutes. The pH was adjusted between 4-5 with 1N HCl and concentrated. The crude product was purified by preparative HPLC to affod 6-(2-(4-methylpiperazin-1-yl)ethyl)imidazo[1,2-a]pyridine-3-carboxylic acid (114). 1H NMR (400 MHz, d6-DMSO) δ 9.25 (s, 1H), 8.35 (s, 1H), 7.83 (d, J=9.2 Hz, 1H), 7.61 (dd, J=1.6, 9.2 Hz, 1H), 4.65-4.19 (m, 8H), 3.49-3.30 (m, 2H), 3.04-2.99 (m, 2H), 2.81 (s, 3H). MS m/z 316.1 (M+1)+.

Workup

  1. concentrationconcentrated
  2. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-bbad68edeebd48878b5a519346a67116
Source dataset
uspto-grants-2015_12
Patent number
US09199981B2

Reaction notes

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