Dimethylformamide → methyl N-[(3-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)acetyl]-N-methylglycinate

HRID 2410584Notes

Reaction equation

HRID 2410584 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8](C2ON=C(C3C=C(CC(O)=O)C=CC=3)N=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)[CH:35]([CH3:37])[CH3:36].CN([C:44]([O:48][N:49]1N=N[C:51]2[CH:52]=[CH:53][CH:54]=[N:55][C:50]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[CH3:66][O:67][C:68](=[O:72])CNC.[CH3:73][N:74]([CH:76]=[O:77])[CH3:75]>CCOC(C)=O>[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:44]2[O:48][N:49]=[C:50]([C:51]3[CH:52]=[C:53]([CH2:54][C:76]([N:74]([CH3:75])[CH2:73][C:68]([O:67][CH3:66])=[O:72])=[O:77])[CH:36]=[CH:35][CH:37]=3)[N:55]=2)[CH:7]=[CH:6][C:5]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH3:31]

Participants

7

Reactant 5

HCID 6228Dimethylformamide2×HCID 81531DiisopropylethylamineHCID 83544Glycine, N-methyl-, methyl ester, hydrochloride (1:1)HCID 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 66678412methyl N-[(3-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)acetyl]-N-methylglycinate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

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, 209 mg, 0.48 mmol) in DMF (2 mL) at 0° C. was added DIEA (252 μL, 1.5 mmol) and HATU (183 mg, 0.48 mmol). After 10 min, a solution of sarcosine methyl ester hydrochloride (74 mg, 0.53 mmol) in DMF (1 mL) was added and the reaction mixture stirred at RT overnight. EtOAc was added and the mixture was washed with water. The organic phase was then dried over MgSO4, filtered and concentrated in vacuo affording the title compound. LC/MS (Method B): 500.2 (M+H)+. HPLC (Method A) Rt 5.73 min (Purity: 98.9%).

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

Sources & evidence

ORD record
ord-0651ec2d62214cbea4fdc8425a2ae5bc
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

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