Water → HCID 66958477, compound

HRID 599424Notes

Reaction equation

HRID 599424 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].Cl[C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][N:22]=2)[N:17]=[CH:16][C:15]=1[N+:24]([O-:26])=[O:25].C(N(CC)CC)C.O>ClCCl>[N+:24]([C:15]1[CH:16]=[N:17][C:18]2[C:23]([C:14]=1[NH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:9])([CH3:11])[CH3:10])=[N:22][CH:21]=[CH:20][CH:19]=2)([O-:26])=[O:25]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 131227874-Chloro-3-nitro-1,5-naphthyridine

Product 1

HCID 66958477HCID 66958477, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of tert-butyl 3-aminopropylcarbamate (15.7 g, 90.2 mmol) in dichloromethane (50 mL) was added dropwise over 30 minutes to a solution of 4-chloro-3-nitro[1,5]naphthyridine (18.0 g, 85.9 mmol) and triethylamine (15.6 mL, 112 mmol) in dichloromethane (235 mL) at room temperature. The reaction mixture was stirred for 2.5 hours and then concentrated under reduced pressure to afford an orange solid. Water (300 mL) was added and the mixture was stirred for 1 hour. The solid was isolated by filtration, washed with water (3×50 mL), and dried under vacuum at 70° C. to afford 29.5 g of tert-butyl 3-[(3-nitro[1,5]naphthyridin-4-yl)amino]propylcarbamate as a yellow solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto afford an orange solid
  3. stirringthe mixture was stirred for 1 hour
  4. customThe solid was isolated by filtration
  5. washwashed with water (3×50 mL)
  6. customdried under vacuum at 70° C.

Sources & evidence

ORD record
ord-9e5aae426bd04e76bcb8cb2139fd5e91
Source dataset
uspto-grants-2011_03
Patent number
US07897767B2

Reaction notes

Loading…