Acetic Acid → HCID 68868291, compound

HRID 730002Notes

Reaction equation

HRID 730002 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[N:13]([CH3:14])[C:12]([C:15]2[N:20]=[C:19]3[N:21]([CH2:29][CH:30]([CH3:32])[CH3:31])[C:22]([N:24]=CN(C)C)=[N:23][C:18]3=[CH:17][CH:16]=2)=[C:11]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[N:10]=1.C(O)(=O)C.Cl.[OH-].[Na+]>O.C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[N:13]([CH3:14])[C:12]([C:15]2[N:20]=[C:19]3[N:21]([CH2:29][CH:30]([CH3:32])[CH3:31])[C:22]([NH2:24])=[N:23][C:18]3=[CH:17][CH:16]=2)=[C:11]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[N:10]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68993390HCID 68993390, compound

Product 1

HCID 68868291HCID 68868291, compoundYield 0.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Heat N′-{5-[2-(2,6-difluorophenyl)-3-methyl-5-phenyl-3H-imidazol-4-yl]-3-isobutyl-3H-imidazo[4,5-b]pyridin-2-yl}-N,N-dimethylformamidine (0.02 g, 0.04 mol) in 1:1 glacial acetic acid:concentrated HCl (0.6 mL) at 100° C. for 30 min. Cool to RT. Add CH2Cl2 and water, neutralize with 5N NaOH to about pH=7 with rapid stirring. Extract the aqueous phase 3× with CH2Cl2, combine organic layers, wash with saturated aqueous NaCl and dry over Na2SO4. Filter and concentrate to give the title compound (0.02 g).

Workup

  1. extractionExtract the aqueous phase 3× with CH2Cl2
  2. washwash with saturated aqueous NaCl
  3. dry with materialdry over Na2SO4
  4. filtrationFilter
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-e9549f92cd454cb195aada46e03e6ae1
Source dataset
uspto-grants-2009_09
Patent number
US07582652B2

Reaction notes

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