Triethylamine → 1-{[(3-Nitro[1,5]naphthyridin-4-yl)amino]methyl}cyclohexanol

HRID 1363577

반응식

HRID 1363577 반응식
C(N(CC)CC)C.Cl[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][N:17]=2)[N:12]=[CH:11][C:10]=1[N+:19]([O-:21])=[O:20].Cl.[NH2:23][CH2:24][C:25]1([OH:31])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>ClCCl.Cl.NCC1(O)CCCCC1>[N+:19]([C:10]1[CH:11]=[N:12][C:13]2[C:18]([C:9]=1[NH:23][CH2:24][C:25]1([OH:31])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)=[N:17][CH:16]=[CH:15][CH:14]=2)([O-:21])=[O:20]

참가 물질

6

반응물 3

HCID 8471Triethylamine2회HCID 3084332Cyclohexanol, 1-(aminomethyl)-, hydrochloride (1:1)HCID 131227874-Chloro-3-nitro-1,5-naphthyridine

생성물 1

HCID 574578211-{[(3-Nitro[1,5]naphthyridin-4-yl)amino]methyl}cyclohexanol수율 100%

시약·촉매·용매 2

HCID 3084332Cyclohexanol, 1-(aminomethyl)-, hydrochloride (1:1)촉매HCID 6344Dichloromethane용매

실험 절차

Triethylamine (8.38 mL, 60.1 mmol) was added over 10 min to a stirred mixture of 4-chloro-3-nitro-1,5-naphthyridine (6.00 g, 28.6 mmol) and 1-aminomethyl-1-cyclohexanol hydrochloride (5.00 g, 30.1 mmol) in dichloromethane (115 mL) at 0° C. The solution was allowed to warm to rt and more 1-aminomethyl-1-cyclohexanol hydrochloride (0.2 g) was added. The solution was stirred overnight and more triethylamine (0.5 mL) was added. After 30 min, the solution was partitioned between saturated aqueous sodium bicarbonate (100 mL) and chloroform (200 mL). The aqueous layer was extracted with chloroform (3×200 mL). The combined organic extracts were washed with saturated aqueous sodium bicarbonate (2×100 mL) and brine (80 mL), dried over MgSO4, filtered, concentrated under reduced pressure, and dried under vacuum to afford 1-{[(3-nitro[1,5]naphthyridin-4-yl)amino]methyl}cyclohexanol as a yellow solid (8.65 g, 100%).

후처리

  1. waitAfter 30 min
  2. customthe solution was partitioned between saturated aqueous sodium bicarbonate (100 mL) and chloroform (200 mL)
  3. extractionThe aqueous layer was extracted with chloroform (3×200 mL)
  4. washThe combined organic extracts were washed with saturated aqueous sodium bicarbonate (2×100 mL) and brine (80 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customdried under vacuum

출처 및 근거

ORD 기록
ord-68d6562ce530417e9b265a8fc48d9707
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07884207B2

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