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

HRID 2410579Notes

Reaction equation

HRID 2410579 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.[C:65]([NH:68][CH2:69][CH2:70][NH2:71])(=[O:67])[CH3:66]>CN(C=O)C.CCOCC>[C:65]([NH:68][CH2:69][CH2:70][NH:71][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)(=[O:67])[CH3:66]

Participants

7

Reactant 4

HCID 66082N-(2-aminoethyl)acetamideHCID 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 66678479N-[2-(acetylamino)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 of crude (3-{5-[2-(methoxymethyl)-2′-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)acetic acid (preparation described in Example 24, Step 1, 308 mg; 0.74 mmol) in DMF (6 mL) at 0° C. was added DIEA (267 4, 1.5 mmol) and HATU (282 mg; 0.74 mmol). After 10 min, a solution of N-acetylethylenediamine (75 mg, 0.74 mmol) in DMF (2 mL) was added and the reaction mixture was stirred at RT overnight. Et2O was added and the mixture was washed with water. The organic phase was dried over MgSO4, filtered and concentrated in vacuo. The crude was purified by preparative HPLC affording the title compound as a white fluffy solid. LC/MS (Method B): 499.3 (M+H)+. HPLC (Method A) Rt 4.89 min (Purity: 100.0%).

Workup

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

Sources & evidence

ORD record
ord-954c5cf54a2e47e29a128c68d531b304
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

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