Diisopropylethylamine → HCID 86690469, compound

HRID 1026746Notes

Reaction equation

HRID 1026746 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]([OH:9])=O)[N:4]=[CH:3]1.C[NH3+].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[Br:52][C:53]1[CH:58]=[C:57]([CH2:59][NH:60][CH:61]2[CH2:64][CH2:63][CH2:62]2)[CH:56]=[CH:55][N:54]=1>CN(C)C=O.C(Cl)(Cl)Cl>[Br:52][C:53]1[CH:58]=[C:57]([CH2:59][N:60]([CH:61]2[CH2:62][CH2:63][CH2:64]2)[C:7]([C:5]2[N:4]=[CH:3][N:2]([CH3:1])[CH:6]=2)=[O:9])[CH:56]=[CH:55][N:54]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 5415091-methyl-1H-imidazole-4-carboxylic acidHCID 866211442-(1H-7-Azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate MethanaminiumHCID 86690470HCID 86690470, compound

Product 1

HCID 86690469HCID 86690469, compoundYield 175.7%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

After a solution of methyl-1H-imidazole-4-carboxylic acid (300 mg), 2-(1H-7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate methanaminium (HATU) (1.27 g) and diisopropylethylamine (431 mg) in dimethylformamide (7 mL) was stirred at room temperature for 15 min, N-[(2-bromopyridin-4-yl)methyl]cyclobutanamine (574 mg) was added thereto and the mixture was stirred at room temperature overnight. The reaction mixture 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. After the desiccant was filtered off, the solvent was distilled off under reduced pressure. The resulting residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=80:20-50:50) to afford the title compound (1.46 g).

Workup

  1. washwashed with saturated aqueous sodium hydrogen carbonate solution
  2. extractionAfter extraction with chloroform
  3. dry with materialthe organic phase was dried over anhydrous magnesium sulfate
  4. filtrationAfter the desiccant was filtered off
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe resulting residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=80:20-50:50)

Sources & evidence

ORD record
ord-b4ad1496af274f848304984ed83956cf
Source dataset
uspto-grants-2014_05
Patent number
US08729271B2

Reaction notes

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