Lithium Hydroxide → 7-(1-(Tert-butoxycarbonyl)piperidin-4-yl)imidazo[1,2-a]pyridine-3-carboxylic acid

HRID 1497888Notes

Reaction equation

HRID 1497888 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][N:17]3[C:20]([C:23]([O:25]CC)=[O:24])=[CH:21][N:22]=[C:16]3[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-].[NH4+].[Cl-]>C1COCC1.CO.O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[CH:19]=[CH:18][N:17]3[C:20]([C:23]([OH:25])=[O:24])=[CH:21][N:22]=[C:16]3[CH:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 25517Ammonium ChlorideHCID 71281180Ethyl 7-(1-(tert-butoxycarbonyl)piperidin-4-yl)imidazo[1,2-a]pyridine-3-carboxylate

Product 1

HCID 712808857-(1-(Tert-butoxycarbonyl)piperidin-4-yl)imidazo[1,2-a]pyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a stirring suspension of ethyl 7-(1-(tert-butoxycarbonyl)piperidin-4-yl)imidazo[1,2-a]pyridine-3-carboxylate (90) (84 mg, 0.23 mmol) in THF:MeOH:H2O (3:2:1, 1 mL) was added 6N LiOH (0.13 mL). The reaction was stirred at room temperature for 2.5 hours then neutralized with NH4Cl and concentrated to afford 7-(1-(tert-butoxycarbonyl)piperidin-4-yl)imidazo[1,2-a]pyridine-3-carboxylic acid (91) which was immediately used without purification. MS (m/z) 346.1 (M+1)+.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-7bb9c06ce9094c48a2b84f68f7cc8b60
Source dataset
uspto-grants-2015_12
Patent number
US09199981B2

Reaction notes

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