2,4-Difluorobenzylamine → HCID 22051191, compound

HRID 1867082Notes

Reaction equation

HRID 1867082 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][N:6]1[CH:11]=[CH:10][C:9](O)=[CH:8][C:7]1=[O:13].[F:17][C:18]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:19]=1[CH2:20][NH2:21]>>[F:17][C:18]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:19]=1[CH2:20][NH:21][C:9]1[CH:10]=[CH:11][N:6]([CH2:5][C:4]2[CH:14]=[CH:15][CH:16]=[C:2]([F:1])[CH:3]=2)[C:7](=[O:13])[CH:8]=1

Participants

3

Reactant 2

HCID 27332442,4-DifluorobenzylamineHCID 54724162HCID 54724162, compound

Product 1

HCID 22051191HCID 22051191, compound

Procedure

The product from Step 2 (0.5 g, 2.28 mmol) and 2,4-difluoro benzylamine (4 mL, 33.6 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 (95:5 ethyl acetate:methanol). The final compound was isolated as a light yellow solid (0.16 g, 36%). 1H NMR (400 MHz, CD3OD) δ 7.33 (m, 3H), 7.03 (d, J=8 Hz, 1H), 6.96 (m, 3H), 6.95 (m, 1H), 5.97 (dd, J=3.2 and 8.0 Hz, 1H), 5.48 (d, J=2.56 Hz, 1H), 5.02 (s, 2H), 4.33 (s, 2H) ppm. 19F NMR (400 MHz, CD3OD) δ −113.88 (1F), −115.33 (1F), −116.78 (1F) ppm. ES-HRMS m/z 345.1221 (M+H calcd for C19H17F3N2O requires 345.1209).

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 (95:5 ethyl acetate:methanol)

Sources & evidence

ORD record
ord-35f4a892fe22426a832dd7449f64e591
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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