Benzylamine → HCID 70873880, compound

HRID 2208829Notes

Reaction equation

HRID 2208829 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[C:3]=1[CH2:10][NH:11][C:12](=[O:24])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15](F)[C:14]=1[C:20]([F:23])([F:22])[F:21].[CH2:25]([NH2:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[CH2:25]([NH:32][C:15]1[C:14]([C:20]([F:23])([F:22])[F:21])=[C:13]([CH:18]=[CH:17][CH:16]=1)[C:12]([NH:11][CH2:10][C:3]1[C:4](=[O:9])[NH:5][C:6]([CH3:8])=[CH:7][C:2]=1[CH3:1])=[O:24])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 70873922HCID 70873922, compound

Product 1

HCID 70873880HCID 70873880, compoundYield 31.1%

Conditions

Temperature
210 °C

Procedure

A suspension of N-[(4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl]-3-fluoro-2-(trifluoro methyl)benzamide (0.80 g, 2.34 mmol) in benzylamine (2.6 ml, 23.4 mmol) was heated in a microwave reactor at 210° C. for 4 h. After cooling distilled water (20 ml) was added to the slurry and 2M HCl was added until the suspension was at pH5. and the mixture was extracted using EtOAc (3×50 ml). The combined organics were washed with pH5 HCl solution (2×50 ml), brine (30 ml), dried using Na2SO4 filtered and evaporated. The resultant oil was purified using a 50 g Isolute silica column eluting with a gradient of 0% to 5% MeOH in DCM to afford the title compound as an off-white solid (313 mg, 29%). LC-MS 94%, m/z=430.2, 1H NMR (500 MHz, Acetone-d6) δ 7.41-7.16 (m, 8H), 6.69 (d, J=8.5 Hz, 1H), 6.50 (d, J=7.4 Hz, 1H), 5.87 (s, 1H), 5.84 (s, 1H), 4.53 (d, J=5.7 Hz, 2H), 4.35 (d, J=5.6 Hz, 2H), 2.28, (d, J=4.0 Hz, 3H), 2.21 (s, 3H).

Workup

  1. temperatureAfter cooling
  2. distillationdistilled water (20 ml)
  3. additionwas added to the slurry and 2M HCl
  4. additionwas added until the suspension
  5. extractionand the mixture was extracted
  6. washThe combined organics were washed with pH5 HCl solution (2×50 ml), brine (30 ml)
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customThe resultant oil was purified
  11. washeluting with a gradient of 0% to 5% MeOH in DCM

Sources & evidence

ORD record
ord-45e31b2f2f944c7bb3d7f568568ce44a
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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