Sodium Hydroxide → 5-[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]pentanamide

HRID 2366706노트

반응식

HRID 2366706 반응식
[NH2:1]C1C=NC2C(C=1NCCCCC(OCC)=O)=CC=CC=2.C(OCC(Cl)=O)C.[CH2:29]([O:31][CH2:32][C:33]1[N:34]([CH2:46][CH2:47][CH2:48][CH2:49][C:50](OCC)=[O:51])[C:35]2[C:44]3[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=3[N:38]=[CH:37][C:36]=2[N:45]=1)[CH3:30].C([O-])(=O)C.[NH4+].[OH-].[Na+]>>[CH2:29]([O:31][CH2:32][C:33]1[N:34]([CH2:46][CH2:47][CH2:48][CH2:49][C:50]([NH2:1])=[O:51])[C:35]2[C:44]3[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=3[N:38]=[CH:37][C:36]=2[N:45]=1)[CH3:30]

참가 물질

6

반응물 5

HCID 14798Sodium HydroxideHCID 84189Ethoxyacetyl chlorideHCID 517165Ammonium AcetateHCID 57447068Ethyl 5-(3-aminoquinolin-4-ylamino)pentanoateHCID 57447091Ethyl 5-(2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)pentanoate

생성물 1

HCID 574470925-[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]pentanamide

반응 조건

온도
110 °C

실험 절차

Ethyl 5-(3-aminoquinolin-4-ylamino)pentanoate, prepared in Parts A and B of Example 34, was treated as described in Part A of Example 36. Ethoxyacetyl chloride was used instead of methoxypropionyl chloride. Ethyl 5-(2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)pentanoate (6.0 g, 17 mmol) and ammonium acetate (15 g) were sealed in a high-pressure vessel and heated for four days at 110° C. and then allowed to cool to ambient temperature. Aqueous sodium hydroxide (10%) was added, and the mixture was then extracted with dichloromethane (3×). The product crystallized from the dichloromethane and was collected in two crops to provide 2.64 g of 5-[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]pentanamide as an off-white solid, mp 157-158° C.

후처리

  1. additionwas treated
  2. temperatureto cool to ambient temperature
  3. extractionthe mixture was then extracted with dichloromethane (3×)
  4. customThe product crystallized from the dichloromethane
  5. customwas collected in two crops

출처 및 근거

ORD 기록
ord-fd480d040bde401587d2a14048ee60f1
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08697873B2

반응 노트

불러오는 중…