Chloroacetyl chloride → HCID 66958446, 화합물

HRID 1364061노트

반응식

HRID 1364061 반응식
C(N(CC)CC)C.[NH2:8][C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1[NH:19][CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:16][CH:15]=[C:14]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH:13]=2.[Cl:38][CH2:39][C:40](Cl)=O>ClCCl>[CH2:31]([O:30][C:14]1[CH:15]=[CH:16][C:17]2[C:18]3[N:19]([CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:40]([CH2:39][Cl:38])=[N:8][C:9]=3[CH:10]=[N:11][C:12]=2[CH:13]=1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

참가 물질

5

반응물 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 66958391Tert-butyl 2-[(3-amino-7-benzyloxyquinolin-4-yl)amino]ethylcarbamate

생성물 1

HCID 66958446HCID 66958446, 화합물수율 15.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Triethylamine (24.0 mL, 172.58 mmol) was added to a solution of tert-butyl 2-[(3-amino-7-benzyloxyquinolin-4-yl)amino]ethylcarbamate (35.25 g, 86.29 mmol) in dichloromethane (400 mL), and the reaction was stirred at ambient temperature. Chloroacetyl chloride (6.87 mL, 86.29 mmol) was quickly added at ambient temperature, and the reaction was stirred for 10 minutes. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in ethanol (500 mL) and stirred for two days at ambient temperature. The mixture was concentrated under reduced pressure and the residue was recrystallized from dichloromethane to afford 6.23 g of tert-butyl 2-[7-benzyloxy-2-(chloromethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethylcarbamate. The mother liquor was divided into two portions which were separately purified by normal phase prep HPLC on silica gel (eluting with 2 N ammonia in methanol/chloroform in a 33-minute gradient from 0:100 to 5:95) and combined to provide an additional 24.21 g of product.

후처리

  1. stirringthe reaction was stirred for 10 minutes
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in ethanol (500 mL)
  4. stirringstirred for two days at ambient temperature
  5. concentrationThe mixture was concentrated under reduced pressure
  6. customthe residue was recrystallized from dichloromethane

출처 및 근거

ORD 기록
ord-0404af802274443c97aee294602fcbb5
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07888349B2

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