Triethylamine → HCID 58833652, 화합물

HRID 2203507노트

반응식

HRID 2203507 반응식
Cl.[C:2](Cl)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1.[NH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:17]=[CH:18][C:19]2[C:20]3[N:29]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:28]([CH2:34][CH2:35][CH3:36])=[N:27][C:21]=3[C:22]([NH2:26])=[N:23][C:24]=2[CH:25]=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[NH2:26][C:22]1[C:21]2[N:27]=[C:28]([CH2:34][CH2:35][CH3:36])[N:29]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:20]=2[C:19]2[CH:18]=[CH:17][C:16]([O:15][CH2:14][CH2:13][CH2:12][NH:11][C:2](=[O:9])[C:3]3[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=3)=[CH:25][C:24]=2[N:23]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 516892Sodium BicarbonateHCID 588337127-(3-aminopropoxy)-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine

생성물 1

HCID 58833652HCID 58833652, 화합물수율 52.2%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

Nicotinoyl chloride hydrochloride (0.23 g, 1.29 mmol) was added in one portion to a solution of 7-(3-aminopropoxy)-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine (0.460 g, 1.29 mmol) and triethylamine (0.383 mL, 2.75 mmol) in chloroform (15 mL), and the reaction was stirred for 16 hours. The reaction mixture was poured into saturated aqueous sodium bicarbonate and stirred for 30 minutes. The aqueous layer was separated and extracted with chloroform. The combined organic fractions were washed sequentially with water and brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting pale yellow oil was triturated with acetonitrile, which was removed under reduced pressure. The resulting solid was recrystallized from acetonitrile to yield 0.310 g of N-{3-[4-amino-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-7-yloxy]propyl}nicotinamide as off-white, granular crystals, mp 172-174° C.

후처리

  1. stirringstirred for 30 minutes
  2. customThe aqueous layer was separated
  3. extractionextracted with chloroform
  4. washThe combined organic fractions were washed sequentially with water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting pale yellow oil was triturated with acetonitrile, which
  9. customwas removed under reduced pressure
  10. customThe resulting solid was recrystallized from acetonitrile

출처 및 근거

ORD 기록
ord-45c75f099f07446bbdaec0c7012e1d60
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365567B2

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