Hydrochloric Acid → HCID 68582637, compound

HRID 2235558Notes

Reaction equation

HRID 2235558 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([NH:9][C:10]2[N:14]([CH3:15])[C:13]3[C:16]([N:20]([C:27]4[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=4)[CH2:21][C:22]([O:24]CC)=O)=[CH:17][CH:18]=[CH:19][C:12]=3[N:11]=2)=[C:4]([O:35][CH3:36])[CH:3]=1.[OH-].[Na+].Cl.[CH2:40]([NH:42][CH2:43][CH3:44])[CH3:41].C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>CO.O.CN(C)C=O>[ClH:1].[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([NH:9][C:10]2[N:14]([CH3:15])[C:13]3[C:16]([N:20]([C:27]4[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=4)[CH2:21][C:22]([N:42]([CH2:43][CH3:44])[CH2:40][CH3:41])=[O:24])=[CH:17][CH:18]=[CH:19][C:12]=3[N:11]=2)=[C:4]([O:35][CH3:36])[CH:3]=1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 8021DiethylamineHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58896524HCID 58896524, compound

Product 1

HCID 68582637HCID 68582637, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl N-[2-[(4-chloro-2-methoxy-6-methylphenyl)amino]-1-methyl-1H-benzimidazol-7-yl]-N-(4-methoxyphenyl)glycinate (20 mg, 0.039 mmol) in methanol (0.5 ml) was added 1N sodium hydroxide (0.5 ml). The mixture was stirred at room temperature for 1.5 h, then neutralized with 1N hydrochloric acid (0.5 ml) and concentrated to dryness. To a mixture of the residue, diethylamine (0.0081 ml, 0.079 mmol) and N,N-dimethylformamide (3 ml) were added triethylamine (0.011 ml, 0.079 mmol) and O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (22.4 mg, 0.079 mmol). The mixture was stirred at room temperature for 1.5 h. The mixture was diluted with water (20 ml) and extracted with ethyl acetate (30 ml). The extract was washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was flash chromatographed eluting with a 20% acetone/hexanes) to give the crude product. The crude product was purified by reverse phase HPLC (acetonitrile containing 0.1 trifluoroacetic acid/water containing 0.1% trifluoroacetic acid). The eluent was concentrated in vacuo and the residue was dissolved in methanol (2 ml) before 2M hydrogen chloride in diethylether (2 ml) was added. The mixture was concentrated in vacuo to give 9.6 mg (46%) of the title as a powder.

Workup

  1. concentrationconcentrated to dryness
  2. stirringThe mixture was stirred at room temperature for 1.5 h
  3. extractionextracted with ethyl acetate (30 ml)
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customchromatographed
  8. washeluting with a 20% acetone/hexanes)

Sources & evidence

ORD record
ord-2949338d5f714527a4de907a1a499ba0
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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