Triethylamine → HCID 178447235, compound

HRID 2105503Notes

Reaction equation

HRID 2105503 reaction equation
[C:1](Cl)(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5].[NH2:8][C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1[OH:19])=[N:16][CH:15]=[CH:14][CH:13]=2.C(N(CC)CC)C>ClCCl>[OH:19][C:18]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][N:16]=2)[N:11]=[CH:10][C:9]=1[NH:8][C:1](=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61186Valeryl chlorideHCID 178508000HCID 178508000, compound

Product 1

HCID 178447235HCID 178447235, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of valeryl chloride (4.4 mL, 37 mmol) in dichloromethane (25 mL) was added dropwise to a stirred suspension of 3-amino[1,5]naphthyridin-4-ol (5.0 g, 31 mmol) and triethylamine (6.6 mL, 47 mmol) in dichloromethane (100 mL), and the reaction was stirred for three days at room temperature. An analysis by LC/MS indicated the reaction was complete after 1.5 hours. The volatiles were removed under reduced pressure, and the residue was stirred with water (100 mL) for 15 minutes. The resulting solid was isolated by filtration and washed with water (100 mL) and diethyl ether (4×50 mL) to provide 5.35 g of N-(4-hydroxy[1,5]naphthyridin-3-yl)pentanamide.

Workup

  1. waitwas complete after 1.5 hours
  2. customThe volatiles were removed under reduced pressure
  3. stirringthe residue was stirred with water (100 mL) for 15 minutes
  4. customThe resulting solid was isolated by filtration
  5. washwashed with water (100 mL) and diethyl ether (4×50 mL)

Sources & evidence

ORD record
ord-0147b2228e474596b3fbc1ed37daf79a
Source dataset
uspto-grants-2009_08
Patent number
US07579359B2

Reaction notes

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