1-methyl-1H-imidazole-4-carboxylic acid → HCID 86690471, compound

HRID 1026747Notes

Reaction equation

HRID 1026747 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]([OH:9])=O)[N:4]=[CH:3]1.[Br:10][C:11]1[CH:12]=[C:13]([CH:20]=[CH:21][C:22]=1[F:23])[CH2:14][NH:15][CH:16]1[CH2:19][CH2:18][CH2:17]1.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1>CO>[Br:10][C:11]1[CH:12]=[C:13]([CH:20]=[CH:21][C:22]=1[F:23])[CH2:14][N:15]([CH:16]1[CH2:17][CH2:18][CH2:19]1)[C:7]([C:5]1[N:4]=[CH:3][N:2]([CH3:1])[CH:6]=1)=[O:9]

Participants

5

Reactant 3

HCID 5415091-methyl-1H-imidazole-4-carboxylic acidHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 62414728HCID 62414728, compound

Product 1

HCID 86690471HCID 86690471, compoundYield 13.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl-1H-imidazole-4-carboxylic acid (1.17 g), N-(3-bromo-4-fluorobenzyl)cyclobutanamine (2.40 g) and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) (3.09 g) in methanol (25 mL) was stirred at room temperature for 4 hr. After the reaction mixture was concentrated under reduced pressure, the resulting residue was diluted with chloroform and washed with saturated aqueous sodium hydrogen carbonate solution. After extraction with chloroform, the organic phase was dried over anhydrous magnesium sulfate. The desiccant was filtered off and the solvent was then distilled off under reduced pressure. The resulting residue was purified by column chromatography (silica gel cartridge, chloroform:methanol=98:2-92:8) to afford the title compound (469 mg).

Workup

  1. concentrationAfter the reaction mixture was concentrated under reduced pressure
  2. additionthe resulting residue was diluted with chloroform
  3. washwashed with saturated aqueous sodium hydrogen carbonate solution
  4. extractionAfter extraction with chloroform
  5. dry with materialthe organic phase was dried over anhydrous magnesium sulfate
  6. filtrationThe desiccant was filtered off
  7. distillationthe solvent was then distilled off under reduced pressure
  8. customThe resulting residue was purified by column chromatography (silica gel cartridge, chloroform:methanol=98:2-92:8)

Sources & evidence

ORD record
ord-2365441e0a7a4f39bda17575ca01b5fc
Source dataset
uspto-grants-2014_05
Patent number
US08729271B2

Reaction notes

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