2,5-Dioxopyrrolidin-1-yl 3-(tritylthio)propanoate → N-[(4-Amino-1-benzyl-1H-imidazo[4,5-c]quinolin-2-yl)methyl]-3-mercaptopropanamide

HRID 1845725노트

반응식

HRID 1845725 반응식
[NH2:1][CH2:2][C:3]1[N:4]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:5]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]=[C:7]([NH2:15])[C:6]=2[N:16]=1.C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[S:31][CH2:32][CH2:33][C:34](ON2C(=O)CCC2=O)=[O:35])C=CC=CC=1>ClCCl>[NH2:15][C:7]1[C:6]2[N:16]=[C:3]([CH2:2][NH:1][C:34](=[O:35])[CH2:33][CH2:32][SH:31])[N:4]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:5]=2[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:8]=1

참가 물질

4

반응물 2

HCID 179354262,5-Dioxopyrrolidin-1-yl 3-(tritylthio)propanoateHCID 574299812-(aminomethyl)-1-benzyl-1H-imidazo[4,5-c]quinolin-4-amine

생성물 1

HCID 57568667N-[(4-Amino-1-benzyl-1H-imidazo[4,5-c]quinolin-2-yl)methyl]-3-mercaptopropanamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of 2-(aminomethyl)-1-benzyl-1H-imidazo[4,5-c]quinolin-4-amine (1.0 g, 3.3 mmol) and succinimido 3-(triphenylmethylthio)propanoate (2.2 g, 4.9 mmol) in dichloromethane (33 mL) was stirred overnight at room temperature. The reaction mixture was warmed and the solvent was removed under reduced pressure. Dichloromethane (30 mL) and trifluoroacetic acid (3 mL) were added and the mixture was stirred over the weekend. Additional trifluoroacetic acid was added. After 4 hours, the mixture was concentrated under reduced pressure and purified by flash chromatography on silica gel (gradient elution with a solution of 2% ammonium hydroxide in methanol and chloroform) followed by crystallization from ethyl acetate/acetonitrile. HRMS (ESI) calcd for C21H21N5OS+H 392.1545, found 392.1534.

후처리

  1. temperatureThe reaction mixture was warmed
  2. customthe solvent was removed under reduced pressure
  3. additionDichloromethane (30 mL) and trifluoroacetic acid (3 mL) were added
  4. stirringthe mixture was stirred over the weekend
  5. additionAdditional trifluoroacetic acid was added
  6. waitAfter 4 hours
  7. concentrationthe mixture was concentrated under reduced pressure
  8. custompurified by flash chromatography on silica gel (
  9. washgradient elution with a solution of 2% ammonium hydroxide in methanol and chloroform)
  10. customfollowed by crystallization from ethyl acetate/acetonitrile

출처 및 근거

ORD 기록
ord-a53da8b2c16a4fa1b59d6bc8c96f7a23
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08951528B2

반응 노트

불러오는 중…