Hydrochloric Acid → HCID 66666011, compound

HRID 872314Notes

Reaction equation

HRID 872314 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[N:9]([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]=2)[CH:10]=1)=[O:4].[OH-].[Na+].Cl>C(O)(C)(C)C.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:8]4[CH:7]=[CH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:10][N:9]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]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66665070HCID 66665070, compound

Product 1

HCID 66666011HCID 66666011, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
70 °C

Procedure

2-[4-(1-tert-butoxycarbonylamino-cyclobutyl)-phenyl]-3-phenyl-imidazo[1,2-a]pyridine-6-carboxylic acid methyl ester (0.76 g) was suspended in tert-butanol (19.2 mL) and treated with dilute aqueous sodium hydroxide solution (1M, 6.1 mL). The mixture was heated to 70° C. for 3.5 h. On cooling the reaction was diluted with water and the pH adjusted to 5 with dilute aqueous hydrochloric acid. The resulting emulsion was extracted with ethyl acetate and the organic extract washed with brine, dried and concentrated in vacuo to give the crude title compound which was used without further purification.

Workup

  1. temperatureOn cooling the reaction
  2. extractionThe resulting emulsion was extracted with ethyl acetate
  3. extractionthe organic extract
  4. washwashed with brine
  5. customdried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cd8fc20aae61415ca6caa09339220d13
Source dataset
uspto-grants-2015_03
Patent number
US08975265B2

Reaction notes

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