Acetyl chloride → HCID 22172706, compound

HRID 989118Notes

Reaction equation

HRID 989118 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[C:15]2[N:16]=[C:17]([CH2:22][CH2:23][CH2:24][CH3:25])[N:18]([CH2:19][CH2:20][NH2:21])[C:14]=2[C:13]2[N:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:7]=1>ClCCl>[NH2:5][C:6]1[C:15]2[N:16]=[C:17]([CH2:22][CH2:23][CH2:24][CH3:25])[N:18]([CH2:19][CH2:20][NH:21][C:1](=[O:3])[CH3:2])[C:14]=2[C:13]2[N:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:7]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 219460272-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethaneamine

Product 1

HCID 22172706HCID 22172706, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under a nitrogen atmosphere, acetyl chloride (50 μL, 0.7 mmole) in dichloromethane (25 mL) was added dropwise to a cooled (ice bath) solution of 2-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethaneamine (0.2 g, 0.7 mmol) in dichloromethane (50 mL). After the addition was complete, the reaction mixture was allowed to warm to ambient temperature. After 30 minutes thin layer chromatography indicated that the reaction was complete. The reaction mixture was washed with 10% sodium hydroxide, water and brine; dried; and concentrated under vacuum to provide 0.25 g of crude product. This material was purified by column chromatography (silica gel eluting with dichloromethane) to provide 0.2 g of a solid. This solid was recrystallized from acetonitrile (30 mL) to provide 0.18 g of N′-[2-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethyl]acetamide as a white powder, m.p.228-230° C. Analysis: Calculated for C17H22N6O: %C, 62.56; %H, 6.79; %N, 25.75; Found: %C, 62.50; %H, 6.59; %N, 26.04. HRMS (EI) calcd for C22H26N6O2 (M+) 326.1855, found 326.1846

Workup

  1. additionAfter the addition
  2. washThe reaction mixture was washed with 10% sodium hydroxide, water and brine
  3. customdried
  4. concentrationand concentrated under vacuum
  5. customto provide 0.25 g of crude product
  6. customThis material was purified by column chromatography (silica gel eluting with dichloromethane)

Sources & evidence

ORD record
ord-a96b5819ae694d85a265f07505ccbc12
Source dataset
uspto-grants-2003_10
Patent number
US06638944B2

Reaction notes

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