2,4-Difluorobenzylamine → HCID 22050838, compound

HRID 1867083Notes

Reaction equation

HRID 1867083 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]([CH3:15])=[CH:13][C:12](O)=[CH:11][C:10]1=[O:17].[F:18][C:19]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:20]=1[CH2:21][NH2:22]>>[F:18][C:19]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:20]=1[CH2:21][NH:22][C:12]1[CH:13]=[C:14]([CH3:15])[N:9]([C:3]2[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=2[F:8])[C:10](=[O:17])[CH:11]=1

Participants

3

Reactant 2

HCID 27332442,4-DifluorobenzylamineHCID 54724198HCID 54724198, compound

Product 1

HCID 22050838HCID 22050838, compound

Procedure

1-(2,6-difluorophenyl)-4-hydroxy-6-methylpyridin-2(1H)-one (0.3 g, 1.26 mmol) and 2,4-difluoro benzylamine (1 mL, 8.4 mmol) were combined in a nitrogen flushed culture tube. The tube was capped and heated at 180 C for 24 h. The excess amine was distilled in vacuo and the residue was chromatographed on silica (1:1 hexanes:ethyl acetate). The compound was approximately 50% pure and was carried on without further purification (0.633 g). 1H NMR (400 MHz, CD3OD) δ 7.53 (m, 1H), 7.41 (m, 1H), 7.16 (t, J=8.8 Hz, 2H), 6.93 (m, 2H), 6.00 (s, 1H), 5.42 (s, 1H), 5.42 (s, 1H), 4.37 (s, 2H), 1.93 (s, 3H) ppm. LC/MS, tr=4.65 minutes (5 to 95% acetonitrile/water over 8 minutes at 1 ml/min with detection 254 nm, at 50° C.). ES-MS m/z 363 (M+H).

Workup

  1. customThe tube was capped
  2. temperatureheated at 180 C for 24 h
  3. distillationThe excess amine was distilled in vacuo
  4. customthe residue was chromatographed on silica (1:1 hexanes:ethyl acetate)
  5. customwas carried on without further purification (0.633 g)
  6. customLC/MS, tr=4.65 minutes (5 to 95% acetonitrile/water over 8 minutes at 1 ml/min with detection 254 nm, at 50° C.)

Sources & evidence

ORD record
ord-74df5c6cb87e4a6fb4648d724f2c0ce6
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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