Toluene → 1,1-dimethylethyl N-[2-(2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethyl]carbamate

HRID 2120832Notes

Reaction equation

HRID 2120832 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[N:9][CH:8]=[CH:7][CH:6]=2.[C:23](OC)(OC)(OC)[CH2:24][CH2:25][CH2:26][CH3:27].C1(C)C=CC=CC=1>C1(C)C(C)=CC=CC=1>[CH2:24]([C:23]1[N:12]([CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:21])[CH3:20])[C:11]2[C:10]3[N:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=1)[CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 1140TolueneHCID 83755Trimethyl orthovalerate2×HCID 22172710tert-butyl N-{2-[(3-amino[1,5]naphthyridin-4-yl)amino]ethyl}carbamate

Product 1

HCID 221727461,1-dimethylethyl N-[2-(2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethyl]carbamateYield 47.4%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

1,1-Dimethylethyl N-{2-[(3-amino[1,5]naphthyridin-4-yl)amino]ethyl}carbamate 0.6 g, 2 mmol), trimethyl orthovalerate (0.35 g, 2.1 mmol), and toluene (25 mL) were combined and heated at reflux for 2 hours. Additional trimethyl orthovalerate (1 eq.) was added and the reaction mixture was heated at reflux overnight. Xylene was added and the toluene was distilled off. The reaction was heated at reflux for an additional 8 hours. The bulk of the xylene was distilled off leaving a volume of about 5 mL. The reaction mixture was allowed to cool. The resulting precipitate was isolated by filtration, washed with heptane and dried to provide 0.35 g of 1,1-dimethylethyl N-[2-(2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethyl]carbamate as an ivory powder, m.p. 198-199° C. Analysis: Calculated for C20H27N5O2: %C, 65.01; %H, 7.36; %N, 18.95. Found: %C, 64.75; %N, 7.57; %N, 19.09.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. temperaturethe reaction mixture was heated
  4. temperatureat reflux overnight
  5. distillationthe toluene was distilled off
  6. temperatureThe reaction was heated
  7. temperatureat reflux for an additional 8 hours
  8. distillationThe bulk of the xylene was distilled off
  9. customleaving a volume of about 5 mL
  10. temperatureto cool
  11. customThe resulting precipitate was isolated by filtration
  12. washwashed with heptane
  13. customdried

Sources & evidence

ORD record
ord-3be1489517524dceb1c6a9d453322000
Source dataset
uspto-grants-2004_02
Patent number
US06693113B2

Reaction notes

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