Ammonia → HCID 46909104, compound

HRID 1631021Notes

Reaction equation

HRID 1631021 reaction equation
Cl.[CH3:2][O:3][CH2:4][C:5]1[CH:10]=[C:9]([C:11]2[O:15][N:14]=[C:13]([C:16]3[CH:17]=[CH:18][C:19]([C:22]([OH:24])=O)=[N:20][CH:21]=3)[N:12]=2)[CH:8]=[CH:7][C:6]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH3:31].C(Cl)(=O)C(Cl)=O.[NH3:38].O1CCOCC1>C(Cl)Cl.CN(C=O)C>[CH3:2][O:3][CH2:4][C:5]1[CH:10]=[C:9]([C:11]2[O:15][N:14]=[C:13]([C:16]3[CH:17]=[CH:18][C:19]([C:22]([NH2:38])=[O:24])=[N:20][CH:21]=3)[N:12]=2)[CH:8]=[CH:7][C:6]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH3:31]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 312751,4-DioxaneHCID 65578Oxalyl chlorideHCID 67135236HCID 67135236, compound

Product 1

HCID 46909104HCID 46909104, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-{5-[2-(methoxymethyl)-2′-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}pyridine-2-carboxylic acid hydrochloride (100 mg, 0.23 mmol) in anhydrous DCM (5 mL) was added oxalyl chloride (0.058 mL, 0.69 mmol) and DMF (1 drop). The resulting mixture was stirred at RT for 1 hour. The reaction mixture was concentrated under reduced pressure. The residue was taken up with anhydrous THF (2 mL) and a 0.5N solution of ammonia in dioxane (4.5 mL, 2.25 mmol) was added. The mixture was stirred at RT for 1 hour, and then concentrated under reduced pressure. The residue was taken up with Et2O. The precipitate was filtered off, washed with Et2O and dried under reduced pressure to give the title compound as a beige powder (88 mg, 96%). HPLC (Method A), Rt: 4.7 min (purity: 95.4%). UPLC/MS, M+(ESI): 401.2. 1H NMR (CD3OD, 300 MHz) δ 9.41 (dd, J=2.1, 0.9 Hz, 1H), 8.71 (dd, J=8.2, 2.1 Hz, 1H), 8.44 (d, J=1.8 Hz, 1H), 8.31 (dd, J=8.2, 0.9 Hz, 1H), 8.24 (dd, J=7.9, 1.8 Hz, 1H), 7.41 (d, J=7.9 Hz, 1H), 7.34 (m, 2H), 7.28 (m, 1H), 7.13 (d, J=7.1 Hz, 1H), 4.24 (s, 2H), 3.32 (s, 3H), 2.09 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. stirringThe mixture was stirred at RT for 1 hour
  3. concentrationconcentrated under reduced pressure
  4. filtrationThe precipitate was filtered off
  5. washwashed with Et2O
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-302344ca5b0f48149ddd961a729af52c
Source dataset
uspto-grants-2014_07
Patent number
US08791142B2

Reaction notes

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