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Sodium Hydroxide → 2-[4-(1-Tert-butoxycarbonylamino-cyclobutyl)-phenyl]-3-phenyl-imidazo[1,2-a]pyridine-7-carboxylic acid

HRID 872331
Notes
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Reaction equation

HRID 872331 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]2[C:11]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]4([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:23][CH2:22][CH2:21]4)=[CH:16][CH:15]=3)[N:13]=[C:7]2[CH:6]=1)=[O:4].[OH-].[Na+]>CO.O>[C:28]([O:27][C:25]([NH:24][C:20]1([C:17]2[CH:16]=[CH:15][C:14]([C:12]3[N:13]=[C:7]4[CH:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:10]=[CH:9][N:8]4[C:11]=3[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:19][CH:18]=2)[CH2:21][CH2:22][CH2:23]1)=[O:26])([CH3:31])([CH3:29])[CH3:30]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 666656142-[4-(1-Tert-butoxycarbonylamino-cyclobutyl)-phenyl]-3-phenyl-imidazo[1,2-a]pyridine-7-carboxylic acid methyl ester

Product 1

HCID 666649662-[4-(1-Tert-butoxycarbonylamino-cyclobutyl)-phenyl]-3-phenyl-imidazo[1,2-a]pyridine-7-carboxylic acidYield 107.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent
HCID 962
Water
Solvent

Procedure

A solution of 2-[4-(1-tert-butoxycarbonylamino-cyclobutyl)-phenyl]-3-phenyl-imidazo[1,2-a]pyridine-7-carboxylic acid methyl ester (2.30 g, 4.60 mmol) in MeOH (77 mL) was added a solution of NaOH (3.7 g, 9.24 mmol, 2.0 equiv) in water (15 mL). The resulting mixture was stirred at room temperature for 12 h. The resulting clear solution was concentrated under pressure. The remaining material was treated with water (50 mL), made acidic with an aqueous 2N HCl solution, and extracted with a 4:1 CH2Cl2/isopropanol solution (4×25 mL). The combined organic phases were dried (Na2SO4 anh) and concentrated under reduced pressure to give 2-[4-(1-tert-butoxycarbonylamino-cyclobutyl)-phenyl]-3-phenyl-imidazo[1,2-a]pyridine-7-carboxylic acid (2.4 g, 107%):

Workup

  1. concentrationThe resulting clear solution was concentrated under pressure
  2. additionThe remaining material was treated with water (50 mL)
  3. extractionextracted with a 4:1 CH2Cl2/isopropanol solution (4×25 mL)
  4. dry with materialThe combined organic phases were dried (Na2SO4 anh)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5156078fa0da48178911b2c5235542ce
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08975265B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes