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

HRID 47501

반응식

HRID 47501 반응식
[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]

참가 물질

5

반응물 3

HCID 1140TolueneHCID 83755Trimethyl orthovalerate2회HCID 22172710tert-butyl N-{2-[(3-amino[1,5]naphthyridin-4-yl)amino]ethyl}carbamate

생성물 1

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

시약·촉매·용매 1

HCID 7237O-Xylene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6164fabd14e74fd497dd1b6b195a606e
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699878B2

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