Isobutylamine → HCID 58789345, compound

HRID 1175623Notes

Reaction equation

HRID 1175623 reaction equation
[CH3:1][C:2]([C:7]1[O:11][N:10]=[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:8]=1)([CH3:6])[C:3]([OH:5])=O.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[CH2:40]([NH2:44])[CH:41]([CH3:43])[CH3:42]>C(Cl)Cl>[CH2:40]([NH:44][C:3](=[O:5])[C:2]([CH3:1])([C:7]1[O:11][N:10]=[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:8]=1)[CH3:6])[CH:41]([CH3:43])[CH3:42]

Participants

6

Reactant 4

HCID 6558IsobutylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68776367HCID 68776367, compound

Product 1

HCID 58789345HCID 58789345, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methyl-2-(3-phenyl-1,2,4-oxadiazol-5-yl)propanoic acid (example 41a) (307 mg, 1.32 mmol) in CH2Cl2 (10 mL) were added HOBt (196 mg, 1.45 mmol), EDCI.HCl (278 mg, 1.45 mmol) and isobutylamine (146 μL, 1.45 mmol). The reaction was stirred at room temperature under N2 for 18 h. Upon completion, the reaction was concentrated and purified by flash-chromatography (0-75% EtOAc in Hexane) to yield N-isobutyl-2-methyl-2-(3-phenyl-1,2,4-oxadiazol-5-yl)propanamide (198 mg, 52%) as a white solid. 1H NMR (500 MHz, DMSO-d6): δ 0.81-0.83 (d, 6H, J=6.7 Hz), 1.66 (s, 6H), 1.70-1.80 (sept, 1H, J=6.7 Hz), 2.89-2.92 (t, 2H, J=6.4 Hz), 7.56-7.61 (m, 3H), 7.92-7.95 (t, 1H, J=5.6 Hz), 8.01-8.03 (m, 2H). MS(M+H, 288).

Workup

  1. concentrationUpon completion, the reaction was concentrated
  2. custompurified by flash-chromatography (0-75% EtOAc in Hexane)

Sources & evidence

ORD record
ord-5e7cd2cad3784ad9a76146f023187e10
Source dataset
uspto-grants-2010_11
Patent number
US07842324B2

Reaction notes

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