Triethylamine → 4-[(3-Nitro[1,5]naphthyridin-4-ylamino)methyl]tetrahydropyran-4-ol

HRID 1363590Notes

Reaction equation

HRID 1363590 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.[NH2:22][CH2:23][C:24]1([OH:30])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1>ClCCl>[N+:12]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[NH:22][CH2:23][C:24]1([OH:30])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)=[N:10][CH:9]=[CH:8][CH:7]=2)([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 131227874-Chloro-3-nitro-1,5-naphthyridineHCID 436087544-(Aminomethyl)oxan-4-ol

Product 1

HCID 669191374-[(3-Nitro[1,5]naphthyridin-4-ylamino)methyl]tetrahydropyran-4-olYield 93.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-chloro-3-nitro[1,5]naphthyridine (16.6 g, 79.0 mmol) in dichloromethane (250 mL) and triethylamine (14.3 mL, 102.7 mmol) was cooled to 4° C. A solution of 4-aminomethyltetrahydropyran-4-ol (11.4 g, 86.9 mmol) in dichloromethane (70 mL) was added dropwise over a period of 30 minutes. The reaction mixture was allowed to stir at ambient temperature over the weekend and then it was concentrated under reduced pressure. The residue was stirred with water (300 mL). The resulting solid was isolated by filtration, rinsed with water, and dried in a vacuum oven at 50° C. for 4 hours to provide 22.53 g of 4-[(3-nitro[1,5]naphthyridin-4-ylamino)methyl]tetrahydropyran-4-ol.

Workup

  1. concentrationit was concentrated under reduced pressure
  2. stirringThe residue was stirred with water (300 mL)
  3. customThe resulting solid was isolated by filtration
  4. washrinsed with water
  5. customdried in a vacuum oven at 50° C. for 4 hours

Sources & evidence

ORD record
ord-faf5ca604fec4eb2874b32885d083b46
Source dataset
uspto-grants-2011_02
Patent number
US07884207B2

Reaction notes

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