Benzylamine → HCID 53629116, compound

HRID 1896367Notes

Reaction equation

HRID 1896367 reaction equation
[O:1]=[C:2]1[CH2:6][CH:5]([CH2:7][CH2:8][CH3:9])[CH2:4][N:3]1[CH2:10][C:11]1[N:15]([CH2:16][C:17]([OH:19])=O)[CH:14]=[N:13][CH:12]=1.C(N(CC)CC)C.[CH2:27]([NH2:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[CH2:27]([NH:34][C:17](=[O:19])[CH2:16][N:15]1[C:11]([CH2:10][N:3]2[CH2:4][CH:5]([CH2:7][CH2:8][CH3:9])[CH2:6][C:2]2=[O:1])=[CH:12][N:13]=[CH:14]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 7504Benzylamine2×HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 57743028HCID 57743028, compound

Product 1

HCID 53629116HCID 53629116, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a 10 ml, three necked flask fitted with a magnetic stirrer, under inert atmosphere, {5-[(2-oxo-4-propylpyrrolidin-1-yl)methyl]-1H-imidazol-1-yl}acetic acid x50 (0.1 g, 0.33 mmol) is dissolved in DMF (1 ml). Triethylamine (0.1 ml, 0.66 mmol), benzylamine (37 μl, 0.33 mmol) and TBTU (0.16 g, 0.33 mmol) are added and the mixture is stirred for 0.5 h at room temperature. An additional amount of benzylamine (0.0165 mmol) is added and stirring is continued overnight. The solvent is evaporated and the residue is purified by chromatography on silicagel (AcOEt/MeOH/NH4OH: 90/9/1 (v/v/v)). The product is treated with a methanolic solution of HCl and the obtained solid is recrystallized from acetonitrile to afford N-benzyl-2-{5-[(2-oxo-4-propylpyrrolidin-1-yl)methyl]-1H-imidazol-1-yl}acetamide 124.

Workup

  1. stirringstirring
  2. waitis continued overnight
  3. customThe solvent is evaporated
  4. customthe residue is purified by chromatography on silicagel (AcOEt/MeOH/NH4OH: 90/9/1 (v/v/v))
  5. additionThe product is treated with a methanolic solution of HCl
  6. customthe obtained solid is recrystallized from acetonitrile

Sources & evidence

ORD record
ord-104fa6bb934b4449a4ddc106d48783e4
Source dataset
uspto-grants-2013_08
Patent number
US08518943B2

Reaction notes

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