Isopropanol → HCID 59843110, compound

HRID 1878743Notes

Reaction equation

HRID 1878743 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[C:9](=[O:10])[CH:8]=[CH:7][C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:5]1.Cl[C:18]1[CH:19]=[CH:20][N:21]=[C:22]2[C:27]=1N=[CH:25][C:24]([O:28][CH3:29])=[CH:23]2.[CH3:30]C(O)C>>[CH3:29][O:28][C:24]1[CH:23]=[C:22]2[C:27]([C:18]([NH:1][CH2:2][CH2:3][N:4]3[C:9](=[O:10])[CH:8]=[CH:7][C:6]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)=[N:5]3)=[CH:19][CH:20]=[N:21]2)=[CH:30][CH:25]=1

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 129026032-(2-aminoethyl)-6-phenylpyridazin-3(2H)-oneHCID 594273408-Chloro-3-methoxy-1,5-naphthyridine

Product 1

HCID 59843110HCID 59843110, compound

Conditions

Temperature
150 °C

Procedure

A mixture of 2-(2-aminoethyl)-6-phenylpyridazin-3(2H)-one (60 mg, 743 μmol) and 8-chloro-3-methoxy-1,5-naphthyridine (55 mg, 282 μmol) in iPrOH (2 mL) was heated to 150° C. for 15 min under microwave. The mixture was filtered and the filtrate was chromatographed on silica with 2-5% (2N NH3-MeOH) in CH2Cl2 to give the product as a white solid (60 mg). MS (ESI pos. ion) calc'd for C21H19N5O2: 373.1; found 374.2 (MH+). 1H NMR (400 MHz, Chloroform-d) δ ppm 3.81-3.89 (m, 2 H) 3.92 (d, J=1.37 Hz, 3 H) 4.64 (t, J=5.48 Hz, 2 H) 6.54 (dd, 1 H) 7.03 (dd, J=9.78, 1.57 Hz, 1 H) 7.10 (s, 1 H) 7.39-7.48 (m, 4 H) 7.66 (dd, J=9.59, 1.56 Hz, 1 H) 7.70-7.79 (m, 2 H) 8.38 (t, 1 H) 8.46 (dd, 1 H).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was chromatographed on silica with 2-5% (2N NH3-MeOH) in CH2Cl2

Sources & evidence

ORD record
ord-435cad99c1874d4d8f25b9ebd7ae9aff
Source dataset
uspto-grants-2012_11
Patent number
US08314087B2

Reaction notes

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