Ethylamine → HCID 67028967, compound

HRID 455073Notes

Reaction equation

HRID 455073 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]([CH2:8][C:9]2[N:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]3=[N:11][C:10]=2[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[C:4](=[O:25])[N:3]=1.[CH2:26]([NH2:28])[CH3:27]>C(O)C>[Cl:24][C:21]1[CH:20]=[CH:19][C:18]([C:10]2[N:11]=[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]3[C:9]=2[CH2:8][N:5]2[CH:6]=[CH:7][C:2]([NH:28][CH2:26][CH3:27])=[N:3][C:4]2=[O:25])=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 6341EthylamineHCID 58337018HCID 58337018, compound

Product 1

HCID 67028967HCID 67028967, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 4-chloro-1-((2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)methyl)pyrimidin-2(1H)-one (50 mg, 0.13 mmol) and ethylamine (30 μl) in ethanol (2 ml) in a sealed tube was heated at 70° C. for 4 hours. Excess reagent was evaporated under reduced pressure. Crude product was dissolved in CH2Cl2 (10 mL) was washed with water, sat. NaHCO3 and brine, dried and evaporated. The crude product was purified by silica gel chromatography. M/e+ 380 for C20H19ClN5O (M+H)+; 1H-NMR (400 MHz, CDCl3) δ 8.42 (d, J=6.6 Hz, 1H), 7.68 (d, J=8.4 Hz, 2H), 7.64 (d, J=9.1 Hz, 1H), 7.47 (d, J=8.4 Hz, 2H), 7.29 (d, J=7.7 Hz, 1H), 6.87 (t, J=6.9 Hz, 1H), 6.65 (d, J=7.3 Hz, 1H), 5.37 (d, J=7.3 Hz, 2H), 4.97 (s, 1H), 3.51 (m, 2H), 3.18 (s, 1H), 1.18 (t, J=7.3 Hz, 3H) ppm.

Workup

  1. customExcess reagent was evaporated under reduced pressure
  2. dissolutionCrude product was dissolved in CH2Cl2 (10 mL)
  3. washwas washed with water, sat. NaHCO3 and brine
  4. customdried
  5. customevaporated
  6. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-07106d619ce645e2b83d43f807f362fb
Source dataset
uspto-grants-2013_07
Patent number
US08497278B2

Reaction notes

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