Hydrochloric Acid → HCID 178422599, compound

HRID 872359Notes

Reaction equation

HRID 872359 reaction equation
C(OC([N:8]1[C:12]([C:13]2[CH:14]=[CH:15][C:16]3[N:17]([C:19]([C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)=[C:20]([C:22]4[CH:27]=[CH:26][C:25]([C:28]5([NH:32]C(OC(C)(C)C)=O)[CH2:31][CH2:30][CH2:29]5)=[CH:24][CH:23]=4)[N:21]=3)[CH:18]=2)=[CH:11][C:10]([CH3:46])=[N:9]1)=O)(C)(C)C.Cl.[OH-].[Na+]>C(Cl)Cl.CO>[CH3:46][C:10]1[CH:11]=[C:12]([C:13]2[CH:14]=[CH:15][C:16]3[N:17]([C:19]([C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)=[C:20]([C:22]4[CH:23]=[CH:24][C:25]([C:28]5([NH2:32])[CH2:29][CH2:30][CH2:31]5)=[CH:26][CH:27]=4)[N:21]=3)[CH:18]=2)[NH:8][N:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 666655825-{2-[4-(1-Tert-butoxycarbonylamino-cyclobutyl)-phenyl]-3-phenyl-imidazo[1,2-a]pyridin-6-yl}-3-methyl-pyrazole-1-carboxylic acid tert-butyl ester

Product 1

HCID 178422599HCID 178422599, compoundYield 18.7%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The crude product from Step 1 (79 mg) was dissolved in DCM/MeOH (2 mL/1 mL) and treated with HCl (4 M soln in dioxane, 0.96 mL). The reaction was stirred for 2 hours before it was poured onto ice, made alkaline with dilute aqueous sodium hydroxide solution (2M) and extracted with DCM. The organic phase was washed with brine, dried and concentrated in vacuo. Purification was achieved by chromatography on silica gel to give the title compound (10 mg).

Workup

  1. additionwas poured onto ice
  2. extractionextracted with DCM
  3. washThe organic phase was washed with brine
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customPurification

Sources & evidence

ORD record
ord-4b79bd4d4d3a4d049abc5b1220e55d5c
Source dataset
uspto-grants-2015_03
Patent number
US08975265B2

Reaction notes

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