N,N-Dimethylethylenediamine → N-[2-(dimethylamino)ethyl]-2-(3-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)acetamide

HRID 2410582Notes

Reaction equation

HRID 2410582 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:16]=[C:17]([CH2:21][C:22]([OH:24])=O)[CH:18]=[CH:19][CH:20]=3)[N:11]=2)[CH:7]=[CH:6][C:5]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH3:31].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:65][N:66]([CH3:70])[CH2:67][CH2:68][NH2:69]>CN(C=O)C.CCOCC>[CH3:65][N:66]([CH3:70])[CH2:67][CH2:68][NH:69][C:22](=[O:24])[CH2:21][C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([C:12]2[N:11]=[C:10]([C:8]3[CH:7]=[CH:6][C:5]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[CH3:31])=[C:4]([CH2:3][O:2][CH3:1])[CH:9]=3)[O:14][N:13]=2)[CH:16]=1

Participants

7

Reactant 4

HCID 66053N,N-DimethylethylenediamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66678441HCID 66678441, compound

Product 1

HCID 58066289N-[2-(dimethylamino)ethyl]-2-(3-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)acetamide

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution (3-{5-[2-(methoxymethyl)-2′-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)acetic acid (preparation described in Example 24 Step 1, 100 mg, 0.24 mmol) in DMF (2 mL) at 0° C., was added DIEA (126 4, 0.72 mmol) and HATU (92 mg, 0.24 mmol). After 10 min, a solution of 2-dimethylaminoethylamine (21 mg, 0.24 mmol) in DMF (2 mL) was added and the reaction mixture stirred at RT overnight. Et2O was added and the mixture was washed with water. The organic phase was then dried over MgSO4, filtered and concentrated in vacuo. The crude was purified by preparative HPLC affording the title compound as a colorless oil. LC/MS (Method B): 485.0 (M+H)+. HPLC (Method A) Rt 4.59 min (Purity: 91.3%).

Workup

  1. washthe mixture was washed with water
  2. dry with materialThe organic phase was then dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude was purified by preparative HPLC

Sources & evidence

ORD record
ord-af199ef7cac5418da61bbf1e2a3a1765
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

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