Ethanol → (7-Propyl-[1,8]naphthyridin-4-yl)-(4-trifluoromethyl-biphenyl-2-yl)-amine

HRID 2197980Notes

Reaction equation

HRID 2197980 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.[F:18][C:19]([F:34])([F:33])[C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:22]([NH2:32])[CH:21]=1>>[CH2:12]([C:6]1[N:7]=[C:8]2[C:3]([C:2]([NH:32][C:22]3[CH:21]=[C:20]([C:19]([F:18])([F:33])[F:34])[CH:25]=[CH:24][C:23]=3[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[CH:11][CH:10]=[N:9]2)=[CH:4][CH:5]=1)[CH2:13][CH3:14]

Participants

4

Reactant 3

HCID 702EthanolHCID 117365264-(Trifluoromethyl)[1,1′-biphenyl]-2-amineHCID 441401765-Chloro-2-propyl-[1,8]naphthyridine2×

Product 1

HCID 68459221(7-Propyl-[1,8]naphthyridin-4-yl)-(4-trifluoromethyl-biphenyl-2-yl)-amine

Conditions

Temperature
100 °C

Procedure

The product from Example 2g as a 3.15M solution in ethanol (0.078 mL, 0.24 mmol) was reacted with the product from Example 218b (0.057 g, 0.24 mmol) for 64 h at 100° C. following the procedure from Example 1g. Consumption of starting material required periodic addition of the product from Example 2g (0.103 mL, 0.32 mmol) in all, and continued heating at 100° C. (70 hrs.). The crude title compound was purified by HPLC with TFA providing the product as a trifluoroacetic acid salt (0.0058 g, 5%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 0.96 (t, J=7.35 Hz, 3H) 1.73-1.92 (m, 2H) 2.90-3.02 (m, 2H) 6.37 (d, J=6.99 Hz, 1H) 7.32 (d, J=7.72 Hz, 3H) 7.48 (dd, J=7.91, 1.65 Hz, 2H) 7.80 (d, J=8.82 Hz, 1H) 7.86 (d, J=8.09 Hz, 1H) 7.94-8.03 (m, 2H) 8.35 (d, J=6.99 Hz, 1H) 8.91 (d, J=8.82 Hz, 1H); MS (ESI+) m/z 408.1 (M+H)+; (ESI−) m/z 406.2 (M−H)−.

Workup

  1. customConsumption of starting material required
  2. customThe crude title compound was purified by HPLC with TFA providing the product as a trifluoroacetic acid salt (0.0058 g, 5%)

Sources & evidence

ORD record
ord-62b6c0f5b9894e109c559a5c47cbae43
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

Loading…