Triethylamine → N4-(3-isopropoxypropyl)-3-nitro[1,5]naphthyridin-4-amine

HRID 2057021Notes

Reaction equation

HRID 2057021 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].C(N(CC)CC)C.[CH:22]([O:25][CH2:26][CH2:27][CH2:28][NH2:29])([CH3:24])[CH3:23]>ClCCl>[CH:22]([O:25][CH2:26][CH2:27][CH2:28][NH:29][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 761943-IsopropoxypropylamineHCID 131227874-Chloro-3-nitro-1,5-naphthyridine

Product 1

HCID 54329107N4-(3-isopropoxypropyl)-3-nitro[1,5]naphthyridin-4-amineYield 84.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Chloro-3-nitro[1,5]naphthyridine (4.1 g), dichloromethane (150 mL), triethylamine (4.1 mL, 29.5 mmol), and 3-isopropoxypropylamine (3.3 mL, 23.8 mmol) were combined. The reaction mixture was maintained at ambient temperature overnight and then quenched with water (100 mL). The phases were separated. The aqueous phase was extracted with dichloromethane (100 mL). The organic phases 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 4.8 g of N4-(3-isopropoxypropyl)-3-nitro[1,5]naphthyridin-4-amine as a yellow powder, m.p. 62.5-63.5° C. Analysis: Calculated for C14H18N4O3: % C, 57.92; % H, 6.25; % N, 19.30; Found: % C, 57.96; % H, 6.19; % N, 19.51. 1H NMR (300 MHz, CDCl3): δ 10.08 (broad s, 1H), 9.38 (broad s, 1H), 8.78 (m, 1H), 8.21 (dd, J=8.4,1.6 Hz, 1H), 7.64 (dd, J=8.4, 4.1 Hz, 1H), 4.57 (broad s, 2H), 3.65-3.57 (m, 3H), 2.05 (t, J=5.6 Hz, 2H), 1.19 (d, J=6.0 Hz, 6H); MS (EI): m/e 290.1366 (290.1378 calc'd for C14H18N4O3).

Workup

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

Sources & evidence

ORD record
ord-b8d0b1f9de0d492cb58311774fbd0764
Source dataset
uspto-grants-2008_02
Patent number
US07335773B2

Reaction notes

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