4-Methylmorpholine → HCID 42641937, compound

HRID 2266746Notes

Reaction equation

HRID 2266746 reaction equation
C1(CN2C([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]([OH:15])=O)=CC=N2)CC1.[CH3:26][C:27]1[N:28]=[CH:29][C:30]([CH2:33][NH2:34])=[N:31][CH:32]=1.CCN=C=N[CH2:40][CH2:41][CH2:42][N:43]([CH3:45])C.C1C=CC2N(O)N=[N:52][C:50]=2C=1.[CH3:56]N1CCOCC1>ClCCl>[CH:41]([C:42]1[N:43]([C:10]2[CH:11]=[C:12]([CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=3)[CH:18]=2)[C:13]([NH:34][CH2:33][C:30]2[CH:29]=[N:28][C:27]([CH3:26])=[CH:32][N:31]=2)=[O:15])[CH:45]=[CH:50][N:52]=1)([CH3:40])[CH3:56]

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 42641937HCID 42641937, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(2-Cyclopropylmethyl-2H-pyrazol-3-yl)-5-(5-methyl-pyridin-2-yl)-benzoic acid (0.234 g, 0.55 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 3-(2-isopropyl-imidazol-1-yl)-N-(5-methyl-pyrazin-2-ylmethyl)-5-(5-methyl-pyridin-2-yl)-benzamide, MS (M+H)=427.

Workup

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

Sources & evidence

ORD record
ord-b3314de8e7c44f928c9d0bd3629b4377
Source dataset
uspto-grants-2010_12
Patent number
US07858654B2

Reaction notes

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