Methylamine → HCID 67052456, compound

HRID 705478Notes

Reaction equation

HRID 705478 reaction equation
[N:1]1[CH:6]=[CH:5][C:4](/[CH:7]=[CH:8]/[C:9](=[O:18])/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[CH:3][CH:2]=1.[CH3:19][NH2:20]>CN(C=O)C>[CH3:19][N:20]1[CH:7]([C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)[CH2:8][C:9](=[O:18])[CH2:10][CH:11]1[C:12]1[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 15941757HCID 15941757, compound

Product 1

HCID 67052456HCID 67052456, compoundYield 48.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of (1E,4E)-1,5-di(pyridin-4-yl)penta-1,4-dien-3-one (1 g, 3.2 mmol) in DMF (10 mL) was treated with N-methylamine (40% in H2O, 2.8 mL, 32 mmol) at 0° C. The solution was warmed up to ambient temperature and stirred for 6 h at RT. The reaction mixture was poured into ice-water and the resulting precipitate was filtered. The aqueous solution was extracted with DCM and the combined organic layers were dried with MgSO4, filtered and evaporated in vacuo. The crude product was purified by flash-chromatography (CH2Cl2/MeOH 9:1) to obtain NW-B591 as a bright yellow solid (417 mg, 48%) (note: mixture of cis/trans isomers in a ratio of 4:1). mp: 103-106° C. 1H NMR (300 MHz, CDCl3) δ (ppm): 8.65 (dd, 4J=4.5 Hz, 3J=1.5 Hz, 4 H, HAr), 7.42 (dd, 3J=4.5 Hz, 4J=1.6 Hz, 4 H, HAr), 3.51 (dd, 3J=12.0 Hz, J=3.2 Hz, 2 H, CH2), 2.82-2.68 (m, 2 H, CH), 2.57-2.46 (m, 2 H, CH2), 1.89 (s, 3 H, CH3). Signals of the minor isomer: 8.65-8.60 (m, 4 H, HAr), 7.25 (dd, 3J=4.7 Hz, 4J=1.5 Hz, 4 H, HAr), 4.13 (t, 3J=6.0 Hz, 2 H, CH), 2.96-2.86 (m, 2 H, CH2), 2.86 (ddd, J=7.9, J=6.0 Hz, J=1.2 Hz, 2 H, CH2), 2.19 (s, 3 H, CH3). 13C NMR (75 MHz, CDCl3) δ (ppm): 204.3 (C), 151.6 (C), 150.4 (CH), 122.2 (CH), 68.9 (CH), 49.6 (CH2), 41.1 (CH3).

Workup

  1. filtrationthe resulting precipitate was filtered
  2. extractionThe aqueous solution was extracted with DCM
  3. dry with materialthe combined organic layers were dried with MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe crude product was purified by flash-chromatography (CH2Cl2/MeOH 9:1)

Sources & evidence

ORD record
ord-e9a8edbc9d914b5ebf925a5e0a1347dc
Source dataset
uspto-grants-2015_11
Patent number
US09174960B2

Reaction notes

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