2,4-Dimethylaniline → HCID 71134799, compound

HRID 1912108Notes

Reaction equation

HRID 1912108 reaction equation
[CH:1]1([C:4]2[N:8]([CH:9]3[CH2:12][CH:11]([CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:10]3)[N:7]=[N:6][C:5]=2[CH:17]([CH2:26][C:27]([O-:29])=O)[CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:3][CH2:2]1.[CH3:30][C:31]1[CH:36]=[C:35]([CH3:37])[CH:34]=[CH:33][C:32]=1[NH2:38].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.C(=O)(O)[O-].[Na+]>O.CN(C=O)C>[CH:1]1([C:4]2[N:8]([CH:9]3[CH2:10][CH:11]([CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:12]3)[N:7]=[N:6][C:5]=2[CH:17]([CH2:26][C:27](=[O:29])[NH:38][C:32]2[CH:33]=[CH:34][C:35]([CH3:37])=[CH:36][C:31]=2[CH3:30])[CH2:18][C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[CH2:2][CH2:3]1

Participants

8

Reactant 5

HCID 72502,4-DimethylanilineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86675059HCID 86675059, compound

Product 1

HCID 71134799HCID 71134799, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Mono-tert-butyl 3-[5-cyclopropyl-1-(3-isobutylcyclobutyl)-1H-[1,2,3]triazol-4-yl]glutarate (106 mg), 2,4-dimethylphenylamine (0.0356 mL) and DMF (1 mL) were mixed. To the mixture were added HOBt.H2O (48.2 mg) and WSC.HCl (60.3 mg) at ice temperature. After stirring at RT overnight, saturated aqueous sodium bicarbonate was added to the reaction mixture at ice temperature. The mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, then dried over sodium sulfate. The sodium sulfate was filtered off and the filtrate was concentrated in vacuo. The resultant residue was purified by preparative chromatography (Eluent: ethyl acetate/hexane=1/2) to give the title compound (105 mg).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationThe sodium sulfate was filtered off
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe resultant residue was purified by preparative chromatography (Eluent: ethyl acetate/hexane=1/2)

Sources & evidence

ORD record
ord-01701c4430924f18ba80cf175440e79a
Source dataset
uspto-grants-2013_12
Patent number
US08604069B2

Reaction notes

Loading…