Dichloromethane → HCID 67135236, compound

HRID 1631020Notes

Reaction equation

HRID 1631020 reaction equation
[OH-].[Na+].[CH3:3][O:4][CH2:5][C:6]1[CH:11]=[C:10]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[CH:19][C:20]([C:23]([O:25]C)=[O:24])=[N:21][CH:22]=3)[N:13]=2)[CH:9]=[CH:8][C:7]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH3:33].C(Cl)[Cl:35]>CO>[ClH:35].[CH3:3][O:4][CH2:5][C:6]1[CH:11]=[C:10]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[CH:19][C:20]([C:23]([OH:25])=[O:24])=[N:21][CH:22]=3)[N:13]=2)[CH:9]=[CH:8][C:7]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH3:33]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 46909103HCID 46909103, compound

Product 1

HCID 67135236HCID 67135236, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 5N aqueous solution of NaOH (0.77 mL, 3.9 mmol) was added into a solution of methyl 5-{5-[2-(methoxymethyl)-2′-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}pyridine-2-carboxylate (400 mg, 0.96 mmol) in MeOH (6 mL). The resulting mixture was stirred at RT for 1.5 hours. The reaction mixture was diluted with DCM and washed with a 1N aqueous solution of HCl (3×). The organic layer was dried (MgSO4) and the solvents were removed under reduced pressure. The residue was taken up with Et2O and an excess of a 1N solution of HCl in Et2O was added. The precipitate was filtered off and dried under reduced pressure to give the title compound as a white powder (370 mg, 88%). HPLC (Method A), Rt: 5.0 min (purity: 94.7%). UPLC/MS, M+(ESI): 402.4. 1H NMR (DMSO-d6, 300 MHz) δ 9.38 (d, J=2.1 Hz, 1H), 8.66 (dd, J=8.2, 2.1 Hz, 1H), 8.34 (d, J=1.8 Hz, 1H), 8.27 (d, J=8.2 Hz, 1H), 8.19 (dd, J=7.9, 1.8 Hz, 1H), 7.44 (d, J=7.9 Hz, 1H), 7.36 (m, 2H), 7.29 (m, 1H), 7.15 (d, J=7.0 Hz, 1H), 4.23 (d, J=12.7 Hz, 1H), 4.16 (d, J=12.7 Hz, 1H), 3.25 (s, 3H), 2.04 (s, 3H).

Workup

  1. washwashed with a 1N aqueous solution of HCl (3×)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customthe solvents were removed under reduced pressure
  4. additionan excess of a 1N solution of HCl in Et2O was added
  5. filtrationThe precipitate was filtered off
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-2d9ac37246114839a071c8a6550a05f0
Source dataset
uspto-grants-2014_07
Patent number
US08791142B2

Reaction notes

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