Dimethylamine → HCID 67092627, compound

HRID 2074103Notes

Reaction equation

HRID 2074103 reaction equation
[F:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][C:7]2[N:11]([CH2:12][C:13]3[O:17][N:16]=[C:15]([C:18]([O:20]CC)=O)[N:14]=3)[N:10]=[C:9]([C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)[CH:8]=2)=[CH:4][CH:3]=1.[CH3:31][NH:32][CH3:33].C(O)(=O)/C=C\C(O)=O>CCO.CCOC(C)=O>[F:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][C:7]2[N:11]([CH2:12][C:13]3[O:17][N:16]=[C:15]([C:18]([N:32]([CH3:33])[CH3:31])=[O:20])[N:14]=3)[N:10]=[C:9]([C:23]3[CH:24]=[CH:25][N:26]=[CH:27][CH:28]=3)[CH:8]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 674DimethylamineHCID 444266Maleic AcidHCID 67092034HCID 67092034, compound

Product 1

HCID 67092627HCID 67092627, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a suspension of ethyl 5-{[5-(4-fluorobenzyl)-3-pyridin-4-yl-1H-pyrazol-1-yl]methyl}-1,2,4-oxadiazole-3-carboxylate (73 mg, 0.18 mmol) in EtOH (3 ml) was added dimethylamine (2 M in MeOH, 4 mL) and the mixture was stirred overnight at room temperature. The solvent was removed and the residue was purified by flash chromatography (2:98 MeOH/CH2Cl2) to give a clear oil. This was taken up in EtOAc (5 ml) and a solution of maleic acid (15 mg, 0.13 mmol) in EtOAc (2 mL) was added to the solution. The resulting salt suspension was stirred for 30 min , filtered and dried overnight to give the title compound (57 mg, 89 %) as an off white solid. 1H NMR (400 MHz, DMSO-D6) δ ppm 8.62 (d, 2 H), 7.82 (d, 2 H), 7.26-7.35 (m, 2 H), 7.12 (t, 2 H,) 6.82 (s, 1 H), 6.00 (s, 2 H), 4.18 (s, 2 H), 3.03 (s, 3 H), 2.95 (s, 3 H); m/z (APCI+) for C21H19N6O2F 407.1 (M+H)+.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by flash chromatography (2:98 MeOH/CH2Cl2)
  3. customto give a clear oil
  4. stirringThe resulting salt suspension was stirred for 30 min
  5. filtrationfiltered
  6. customdried overnight

Sources & evidence

ORD record
ord-1f6c13c13b6346f9959f5210b1af78bb
Source dataset
uspto-grants-2011_04
Patent number
US07919488B2

Reaction notes

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