Ethanol → (5-Methyl-biphenyl-2-yl)-(7-propyl-[1,8]naphthyridin-4-yl)-amine

HRID 2197982Notes

Reaction equation

HRID 2197982 reaction equation
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:12][CH2:13][CH3:14])=[N:7]2.C(O)C.[CH3:18][C:19]1[CH:20]=[CH:21][C:22]([NH2:31])=[C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:24]=1>>[CH3:18][C:19]1[CH:20]=[CH:21][C:22]([NH:31][C:2]2[C:3]3[C:8](=[N:7][C:6]([CH2:12][CH2:13][CH3:14])=[CH:5][CH:4]=3)[N:9]=[CH:10][CH:11]=2)=[C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:24]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 47121654-Methyl-2-phenylanilineHCID 441401765-Chloro-2-propyl-[1,8]naphthyridine2×

Product 1

HCID 68461607(5-Methyl-biphenyl-2-yl)-(7-propyl-[1,8]naphthyridin-4-yl)-amine

Conditions

Temperature
100 °C

Procedure

The product from Example 2g as a 4.1M solution in ethanol (0.10 mL, 0.40 mmol) was reacted with the product from Example 219c (0.0724 g, 0.40 mmol) for 66 h at 100° C. following the procedure from Example 1g. Consumption of starting material required a second addition of the product from Example 2g (0.03 mL, 0.12 mmol) and continued heating at 100° C. (19 h). The crude title compound was purified by HPLC with TFA providing the product as a trifluoroacetic acid salt (0.060 g, 32%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 0.95 (t, J=7.35 Hz, 3H) 1.70-1.89 (m, 2H) 2.46 (s, 3H) 2.88-3.00 (m, 2H) 6.28 (d, J=6.99 Hz, 1H) 7.11-7.53 (m, 8H) 7.76 (d, J=8.82 Hz, 1H) 8.30 (d, J=6.99 Hz, 1H) 8.91 (d, J=8.82 Hz, 1H) 10.98 (s, 1H); MS (ESI+) m/z 354.2 (M+H)+.

Workup

  1. customConsumption of starting material
  2. customThe crude title compound was purified by HPLC with TFA providing the product as a trifluoroacetic acid salt (0.060 g, 32%)

Sources & evidence

ORD record
ord-44cd4ad42ac64c639838af8bc28df24c
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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