Citric Acid → HCID 71280629, compound

HRID 1497879Notes

Reaction equation

HRID 1497879 reaction equation
[C:1]([O:5][C:6](=[O:23])[CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]2[N:13]([C:15]([C:18]([O:20]CC)=[O:19])=[CH:16][N:17]=2)[CH:14]=1)([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CO>[C:1]([O:5][C:6](=[O:23])[CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]2[N:13]([C:15]([C:18]([OH:20])=[O:19])=[CH:16][N:17]=2)[CH:14]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 3939Lithium HydroxideHCID 71280911HCID 71280911, compound

Product 1

HCID 71280629HCID 71280629, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A stirring mixture of ethyl 6-(3-tert-butoxy-3-oxopropyl)imidazo[1,2-a]pyridine-3-carboxylate (71) (400 mg, 1.26 mmol) and 2N LiOH (1 mL) in THF:MeOH (4:1, 4 mL) was heated at 60° C. for 30 minutes. The reaction was cooled to room temperature and the pH was adjusted between 3-5 with 10% citric acid. The solvent was partially reduced. The resulting solid was collected by vacuum filtration and washed with excess water. Crude 6-(3-(tert-butoxy)-3-oxopropyl)imidazo[1,2-a]pyridine-3-carboxylic acid (72) was dried and used in the next step without further purification. 1H NMR (400 MHz, d6-DMSO) δ 9.11 (s, 1 H), 8.20 (s, 1 H), 7.72 (dd, J=0.8, 9.2 Hz, 1 H), 7.50 (dd, J=1.6, 9.2 Hz, 1 H), 2.91 (t, J=6.8 Hz, 2 H), 2.60 (t, J=7.2, 2 H), 1.33 (s, 9 H). MS m/z 291.13 (M+1)+.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationThe resulting solid was collected by vacuum filtration
  3. washwashed with excess water
  4. dry with materialCrude 6-(3-(tert-butoxy)-3-oxopropyl)imidazo[1,2-a]pyridine-3-carboxylic acid (72) was dried
  5. customused in the next step without further purification

Sources & evidence

ORD record
ord-abc06dec739c4a56991460e26978c898
Source dataset
uspto-grants-2015_12
Patent number
US09199981B2

Reaction notes

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