1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-Chloro-(1-hydroxy-cycloheptylmethyl)-5-(5-methyl-1H-pyrazol-3-yl)-benzamide

HRID 1988373Notes

Reaction equation

HRID 1988373 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[CH:15]=[C:14]([CH3:16])[NH:13][N:12]=2)=[CH:7][C:3]=1[C:4]([OH:6])=O.O[N:18]1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.Cl.N[CH2:40][C:41]1([OH:48])[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]1>CN(C=O)C>[Cl:1][C:2]1[C:10]([CH2:40][C:41]2([OH:48])[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]2)=[CH:9][C:8]([C:11]2[CH:15]=[C:14]([CH3:16])[NH:13][N:12]=2)=[CH:7][C:3]=1[C:4]([NH2:18])=[O:6]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 184386471-(Aminomethyl)cycloheptanol hydrochlorideHCID 184386602-chloro-5-(5-methyl-1H-pyrazol-3-yl)benzoic acid

Product 1

HCID 690553682-Chloro-(1-hydroxy-cycloheptylmethyl)-5-(5-methyl-1H-pyrazol-3-yl)-benzamideYield 26.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-chloro-5-(5-methyl-1H-pyrazol-3-yl)-benzoic acid (100 mg, 0.422 mmol) in DMF (10 mL) was added 1-hydroxybenzotriazole (85 mg, 0.63 mmol), polystyrene supported 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (1.24 g, 1.27 mmol) and 1-aminomethyl-cycloheptanol hydrochloride (113.4 mg, 0.633 mmol). The mixture was stirred at room temperature for 15 minutes, then polystyrene supported N,N-dimethylaminopyridine (0.64 g, 0.93 mmol) was added and the mixture was stirred at room temperature for 16 h. The mixture was filtered through a glass frit, and the residue was washed thoroughly with methanol. The filtrate was concentrated to dryness in vacuo. The residue was purified by reverse phase chromatography to afford the title compound as a white solid (40 mg). LC/MS (M/z): 362.5 (M+1).

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at room temperature for 16 h
  3. filtrationThe mixture was filtered through a glass frit
  4. washthe residue was washed thoroughly with methanol
  5. concentrationThe filtrate was concentrated to dryness in vacuo
  6. customThe residue was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-a5f3f25d0a094dceaddfb8ddf91ae2d4
Source dataset
uspto-grants-2009_06
Patent number
US07553972B2

Reaction notes

Loading…