4-Methylmorpholine → HCID 57770619, compound

HRID 2091824Notes

Reaction equation

HRID 2091824 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9]([C:10]3[CH:11]=[C:12]([CH:16]=[C:17]([C:19]4[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=4)[CH:18]=3)[C:13](O)=[O:14])=[CH:8][CH:7]=[N:6]2)[CH2:3][CH2:2]1.[CH3:26][C:27]1[N:28]=[CH:29][C:30]([CH2:33][NH2:34])=[N:31][CH:32]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>ClCCl>[CH:1]1([CH2:4][N:5]2[C:9]([C:10]3[CH:11]=[C:12]([CH:16]=[C:17]([C:19]4[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=4)[CH:18]=3)[C:13]([NH:34][CH2:33][C:30]3[CH:29]=[N:28][C:27]([CH3:26])=[CH:32][N:31]=3)=[O:14])=[CH:8][CH:7]=[N:6]2)[CH2:3][CH2:2]1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 27564962-(Aminomethyl)-5-methylpyrazineHCID 57770667HCID 57770667, compound

Product 1

HCID 57770619HCID 57770619, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(2-Cyclopropylmethyl-2H-pyrazol-3-yl)-5-(5-methyl-pyridin-2-yl)-benzoic acid (0.120 g, 0.36 mmol), C-(5-methyl-pyrazin-2-yl)-methylamine (0.044 g, 0.36 mmol), EDCI (0.103 g, 0.54 mmol), HOBt (0.073 g, 0.54 mmol), and NMM (0.183 g, 1.80 mmol) were added to 7 mL of dichloromethane. The reaction mixture was stirred for 48 hours at room temperature, then concentrated under reduced pressure. The residue was purified via flash chromatography (5:1 EtOAc/hexanes) to give 0.14 g of 3-(2-cyclopropylmethyl-2H-pyrazol-3-yl)-N-(5-methyl-pyrazin-2-ylmethyl)-5-(5-methyl-pyridin-2-yl)-benzamide, MS (M+H)=439.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified via flash chromatography (5:1 EtOAc/hexanes)

Sources & evidence

ORD record
ord-99567e0dc76e4e3c9b71226a1f06ccbb
Source dataset
uspto-grants-2013_05
Patent number
US08440673B2

Reaction notes

Loading…