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

HRID 1351581Notes

Reaction equation

HRID 1351581 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-24e10756614f4403948af73e3e78f27e
Source dataset
uspto-grants-2007_05
Patent number
US07217716B2

Reaction notes

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