Dicyclohexylcarbodiimide → [5-(3-benzofuran-2-yl-phenyl)-1,4-dimethyl-1H-pyrazol-3-yl]-[4-(2-hydroxy-ethyl)-[1,4]diazepan-1-yl]-methanone

HRID 1011903

Reaction equation

HRID 1011903 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[N:20]([CH3:21])[N:19]=[C:18]([C:22]([OH:24])=O)[C:17]=1[CH3:25].[N:26]1([CH2:33][CH2:34][OH:35])[CH2:32][CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[N:20]([CH3:21])[N:19]=[C:18]([C:22]([N:29]2[CH2:30][CH2:31][CH2:32][N:26]([CH2:33][CH2:34][OH:35])[CH2:27][CH2:28]2)=[O:24])[C:17]=1[CH3:25]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 27365502-(1,4-Diazepan-1-yl)ethan-1-olHCID 673142975-(3-benzofuran-2-yl-phenyl)-1,4-dimethyl-1H-pyrazole-3-carboxylic acid

Product 1

HCID 67314874[5-(3-benzofuran-2-yl-phenyl)-1,4-dimethyl-1H-pyrazol-3-yl]-[4-(2-hydroxy-ethyl)-[1,4]diazepan-1-yl]-methanoneYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 0.060 g (0.18 mmol) of 5-(3-benzofuran-2-yl-phenyl)-1,4-dimethyl-1H-pyrazole-3-carboxylic acid in 2 ml of CH2Cl2 was added 0.031 g (0.22 mmol) of 2-(1,4-diazepan-1-yl)ethan-1-ol, diluted in 1.7 ml of CH2Cl2. This solution was treated at 0° C. with 0.048 g (0.23 mmol) of DCC. The reaction was allowed to warm up over night to RT, then partitioned between aqueous saturated NaHCO3/EtOAc (3×). The organic phases were washed with aqueous saturated NaHCO3, dried (Na2SO4) and evaporated. The residue was suspended in EtOAc and filtered to remove the DCC urea. Purification by flash chromatography (SiO2—NH2, n-heptane/EtOAc 1:4) gave 0.033 g (39%) of [5-(3-benzofuran-2-yl-phenyl)-1,4-dimethyl-1H-pyrazol-3-yl]-[4-(2-hydroxy-ethyl)-[1,4]diazepan-1-yl]-methanone as white oil. MS: 459.3 (MH+).

Workup

  1. custompartitioned between aqueous saturated NaHCO3/EtOAc (3×)
  2. washThe organic phases were washed with aqueous saturated NaHCO3
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. filtrationfiltered
  6. customto remove the DCC urea
  7. customPurification by flash chromatography (SiO2—NH2, n-heptane/EtOAc 1:4)

Sources & evidence

ORD record
ord-e741a131714d448195f6d2f35319d480
Source dataset
uspto-grants-2011_07
Patent number
US07977358B2

Linked notes

Loading…