Furfurylamine → HCID 118414927, compound

HRID 1054311Notes

Reaction equation

HRID 1054311 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:5]2[C:10]([CH3:11])=[N:9][N:8]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:15][CH:14]=3)[C:6]=2[N:7]=1.[NH2:31][CH2:32][C:33]1[O:34][CH:35]=[CH:36][CH:37]=1.CC(O)C>O>[O:34]1[CH:35]=[CH:36][CH:37]=[C:33]1[CH2:32][NH:31][C:2]1[CH:3]=[C:4]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:5]2[C:10]([CH3:11])=[N:9][N:8]([CH2:12][C:13]3[CH:14]=[CH:15][C:16]([O:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:17][CH:18]=3)[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 3438FurfurylamineHCID 3776IsopropanolHCID 118414928HCID 118414928, compound

Product 1

HCID 118414927HCID 118414927, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

(see, e.g., WO2013039988A1). A pressure vessel was charged with 50 (119 mg, 0.28 mmol), 2-aminomethylfuran (0.12 mL, 1.36 mmol) and iPrOH (4 mL). The vessel was sealed and the reaction mixture was heated at 100° C. overnight. An additional 1 mL (11.3 mmol) of amine was added and the mixture was heated at 150° C. overnight. The reaction mixture was diluted with H2O (10 mL) and extracted with EtOAc (15 mL×2). Combined organic layers were washed with brine, dried (Na2SO4) and concentrated under reduced pressure. Crude was subjected to flash column chromatography on silica gel to provide the title compound (40 mg, 30%) as an orange oil. 1H NMR (400 MHz, CDCl3) δ 7.36-7.24 (m, 5H), 7.07 (t, J=7.3 Hz, 1H), 6.97 (d, J=8.2 Hz, 2H), 6.91 (d, J=8.2 Hz, 2H), 6.80 (s, 1H), 6.30 (s, 1H), 6.22 (s, 1H), 5.47 (s, 2H), 5.14 (t, J=5.4 Hz, 1H), 4.68 (d, J=5.5 Hz, 2H), 4.43 (q, J=7.1 Hz, 2H), 2.58 (s, 3H), 1.42 (t, J=7.1 Hz, 3H). 13C NMR (100 MHz, CDCl3) δ 165.83, 157.16, 156.86, 156.51, 152.16, 152.06, 141.97, 141.27, 134.71, 132.57, 129.67, 129.44, 123.17, 118.82, 110.40, 107.27, 106.91, 104.45, 61.66, 49.53, 38.75, 16.15, 14.23. ESI MS: m/z 483.1 (M+H)+.

Workup

  1. customThe vessel was sealed
  2. temperaturethe mixture was heated at 150° C. overnight
  3. extractionextracted with EtOAc (15 mL×2)
  4. washCombined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3719a112f21349018fe5718728fec15e
Source dataset
uspto-grants-2016_07
Patent number
US09394303B2

Reaction notes

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