HCID 86655129, compound → HCID 67308199, compound

HRID 455157Notes

Reaction equation

HRID 455157 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][N:11]3[C:16]=2[CH2:17][C:18]2[CH:23]=[C:22](Cl)[N:21]=[CH:20][N:19]=2)=[CH:4][CH:3]=1>CN(C)CCN.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][N:11]3[C:16]=2[CH2:17][C:18]2[N:19]=[CH:20][N:21]=[C:22]([NH:9][CH2:8][CH2:16][N:11]([CH3:12])[CH3:10])[CH:23]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 86655129HCID 86655129, compound

Product 1

HCID 67308199HCID 67308199, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 66053N,N-DimethylethylenediamineSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 100 mg of 2-(4-chlorophenyl)-3-((6-chloropyrimidin-4-yl)methyl)imidazo[1,2-a]pyridine (0.282 mmol, 1 eq) in 1 mL of N,N-dimethylethane-1,2-diamine (excess) in a sealed tube was heated to 95° C. for 2 h. The solution was then diluted with EtOAc, washed with water, dried on MgSO4, filtered and concentrated. The crude was purified by silica gel chromatography (MeOH:NH4OH (95:5)/EtOAc, 0 to 15%). The product was finally washed with ether (33 mg, 29%) m/e+=407 (M+H+). 1H-NMR (400 MHz, CDCl3, δ): 8.55 (s, 1H), 7.90 (d, 1H, D, J=6.6 Hz), 7.73 (d, 2H, D, J=8.4 Hz), 7.67 (d, 1H, D, J=9.2 Hz), 7.42 (d, 2H, D, J=8.8 Hz), 7.25 (t, 1H, D, J=7.7 Hz), 6.81 (t, 1H, D, 7.7 Hz), 5.86 (s, 1H), 4.38 (s, 2H), 2.43 (m, 2H), 2.17 (s, 6H).

Workup

  1. washwashed with water
  2. customdried on MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude was purified by silica gel chromatography (MeOH:NH4OH (95:5)/EtOAc, 0 to 15%)
  6. washThe product was finally washed with ether (33 mg, 29%) m/e+=407 (M+H+)

Sources & evidence

ORD record
ord-2111d378d35a49f59bfc4a095539f3c4
Source dataset
uspto-grants-2013_07
Patent number
US08497278B2

Reaction notes

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