1-Hydroxybenzotriazole → HCID 67460053, compound

HRID 554093Notes

Reaction equation

HRID 554093 reaction equation
[CH3:1][C:2](=[CH2:13])[CH2:3][N:4]1[C:11](=[O:12])[CH2:10][CH2:9][C@H:5]1[C:6]([OH:8])=O.ON1C2C=CC=CC=2N=N1.[Cl:24][C:25]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=1[CH2:32][NH2:33].Cl.CN(C)CCCN=C=NCC>ClCCl>[Cl:24][C:25]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=1[CH2:32][NH:33][C:6](=[O:8])[C@@H:5]1[CH2:9][CH2:10][C:11](=[O:12])[N:4]1[CH2:3][C:2]([CH3:1])=[CH2:13]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 1399092-Chloro-4-fluorobenzylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67462825HCID 67462825, compound

Product 1

HCID 67460053HCID 67460053, compoundYield 13.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Crude 1-(2-methyl-2-propen-1-yl)-5-oxoproline (˜0.075 g, ˜0.41 mmol, prepared as described below) was dissolved in dichloromethane (5 ml) and to this was added 1-Hydroxybenzotriazole (0.061 g, 0.45 mmol), [(2-chloro-4-fluorophenyl)methyl]amine (0.068 g, 0.43 mmol), and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.087 g, 0.45 mmol). The mixture was then stirred at room temperature for 24 hrs. The mixture was diluted with more dichloromethane then washed sequentially with 2M aqueous hydrogen chloride and saturated aqueous sodium hydrogen carbonate. The organic layer was filtered through a phase separator and evaporated to give a brown residue which was purified by mass-directed automated HPLC to give pure N-[(2-chloro-4-fluorophenyl)methyl]-1-(2-methyl-2-propen-1-yl)-5-oxoprolinamide (0.018 g) as a white solid. LC/MS [M+H]+=325.1, retention time=2.40 minutes.

Workup

  1. washthen washed sequentially with 2M aqueous hydrogen chloride and saturated aqueous sodium hydrogen carbonate
  2. filtrationThe organic layer was filtered through a phase separator
  3. customevaporated
  4. customto give a brown residue which
  5. customwas purified

Sources & evidence

ORD record
ord-68100797a1b14198b942ea1d804f4504
Source dataset
uspto-grants-2011_11
Patent number
US08048907B2

Reaction notes

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