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

HRID 636621Notes

Reaction equation

HRID 636621 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-c9a1fcfa509a4abdbc94e3bee8023533
Source dataset
uspto-grants-2001_02
Patent number
US06194425B1

Reaction notes

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