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

HRID 44740

反応式

HRID 44740 の反応式
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]

参加物

6

反応物 3

HCID 8471Triethylamine2 回HCID 3084332Cyclohexanol, 1-(aminomethyl)-, hydrochloride (1:1)HCID 131227874-Chloro-3-nitro-1,5-naphthyridine

生成物 1

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

試薬・触媒・溶媒 2

HCID 3084332Cyclohexanol, 1-(aminomethyl)-, hydrochloride (1:1)触媒HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-262719eb40b84e888b1c691da79c1d6b
出典データセット
uspto-grants-2013_09
特許番号
US08541438B2

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