Water → N4-(3-butoxypropyl)-3-nitro[1,5]naphthyridin-4-amine

HRID 47495Notes

Reaction equation

HRID 47495 reaction equation
[CH2:1]([O:5][CH2:6][CH2:7][CH2:8][NH2:9])[CH2:2][CH2:3][CH3:4].Cl[C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][N:19]=2)[N:14]=[CH:13][C:12]=1[N+:21]([O-:23])=[O:22].C(N(CC)CC)C.O>ClCCl>[CH2:1]([O:5][CH2:6][CH2:7][CH2:8][NH:9][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][N:19]=2)[N:14]=[CH:13][C:12]=1[N+:21]([O-:23])=[O:22])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 854611-Propanamine, 3-butoxy-HCID 131227874-Chloro-3-nitro-1,5-naphthyridine

Product 1

HCID 53664451N4-(3-butoxypropyl)-3-nitro[1,5]naphthyridin-4-amineYield 79.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under a nitrogen atmosphere, 3-butoxypropylamine (4.0 mL, 26 mmol) was added dropwise over a period of 10 minutes to a solution of 4-chloro-3-nitro[1,5]naphthyridine (4.6 g, 22 mmol) and triethylamine (4.6 mL, 33 mmol) in dichloromethane (150 mL). The reaction mixture was maintained at ambient temperature overnight. Water (100 mL) was added and the phases were separated. The aqueous phase was extracted with dichloromethane (100 mL). The organic fractions were combined, dried over magnesium sulfate, filtered and then concentrated under vacuum to provide a yellow oil. The oil was purified by flash chromatography (silica gel eluting with 1:1 ethyl acetate:hexanes) to provide 5.3 g of N4-(3-butoxypropyl)-3-nitro[1,5]naphthyridin-4-amine as a colorless oil. 1H NMR (300 MHz, CDCl3): δ10.08 (broad s, 1H), 9.38 (broad s, 1H), 8.78 (m, 1H), 8.22 (dd, J=8.4,1.6 Hz, 1H), 7.64 (dd, J=8.4,4.1 Hz, 1H), 4.57 (broad s, 2H), 3.63 (t, J=5.8 Hz, 2H), 3.46 (t, J=6.7 Hz, 2H), 2.10-2.03 (m, 2H), 1.65-1.55 (m, 2H), 1.44-1.32 (m, 2H), (t, J=7.3 Hz, 3H); MS (EI): m/e 304.1535 (304.1535 calc'd for C15H20N4O3).

Workup

  1. customthe phases were separated
  2. extractionThe aqueous phase was extracted with dichloromethane (100 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customto provide a yellow oil
  7. customThe oil was purified by flash chromatography (silica gel eluting with 1:1 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-139649b501d34383a5cb87fe6ebd650b
Source dataset
uspto-grants-2004_03
Patent number
US06699878B2

Reaction notes

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