Dimethylformamide → {4-[(3-Methoxy-pyrazin-2-ylamino)-methyl]-piperidin-1-yl}-((1R,2R)-2-phenyl-cyclopropyl)-methanone

HRID 1827219Notes

Reaction equation

HRID 1827219 reaction equation
[CH3:1][O:2][C:3]1[C:4]([NH:9][CH2:10][CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[N:5][CH:6]=[CH:7][N:8]=1.ON1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2N=N1.Cl.C(N=C=N[CH2:33][CH2:34][CH2:35]N(C)C)C.CN([CH:42]=[O:43])C>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[C:4]([NH:9][CH2:10][CH:11]2[CH2:16][CH2:15][N:14]([C:42]([C@@H:35]3[CH2:34][C@H:33]3[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:43])[CH2:13][CH2:12]2)=[N:5][CH:6]=[CH:7][N:8]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 221357494-[(3-Methoxy-pyrazin-2-ylamino)-methyl]-piperidine

Product 1

HCID 58635337{4-[(3-Methoxy-pyrazin-2-ylamino)-methyl]-piperidin-1-yl}-((1R,2R)-2-phenyl-cyclopropyl)-methanone

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-[(3-methoxy-pyrazin-2-ylamino)-methyl]-piperidine (0.093 g, 0.00042 mol), 1-hydroxybenzotriazole (0.078 g, 0.0005 mol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.097 g, 0.0005 mole) and (1R,2R)-2-phenylcyclopropropanecarboxylic acid (T. Riley et al., J. Med. Chem., 15, 1187, 1972) (0.072 g, 0.00044 mol) in DMF (2 mL) were stirred at rt for 18 h. The reaction was diluted with ethyl acetate (30 mL), washed with 10% aqueous sodium bicarbonate (20 mL) followed by brine (10 mL), concentrated in vacuo and chromatographed on silica using 50–100% ethyl acetate/hexane. Crystallization from ether/hexane gave the title compound. M.S.(M+1): 367.

Workup

  1. washwashed with 10% aqueous sodium bicarbonate (20 mL)
  2. concentrationconcentrated in vacuo
  3. customchromatographed on silica using 50–100% ethyl acetate/hexane
  4. customCrystallization from ether/hexane

Sources & evidence

ORD record
ord-25a805e58c79490ebb2e85033407a5bd
Source dataset
uspto-grants-2006_05
Patent number
US07053089B2

Reaction notes

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