Dichloromethane → N-{3-[(4-amino-2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)amino]propyl}-3-mercaptopropanamide

HRID 1845719노트

반응식

HRID 1845719 반응식
Cl.[NH2:2][CH2:3][CH2:4][CH2:5][NH:6][N:7]1[C:19]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=[C:11]([NH2:20])[C:10]=2[N:9]=[C:8]1[CH3:21].C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[S:29][CH2:30][CH2:31][C:32](ON2C(=O)CCC2=O)=[O:33])C=CC=CC=1.C(N(CC)CC)C.ClCCl>CO>[NH2:20][C:11]1[C:10]2[N:9]=[C:8]([CH3:21])[N:7]([NH:6][CH2:5][CH2:4][CH2:3][NH:2][C:32](=[O:33])[CH2:31][CH2:30][SH:29])[C:19]=2[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:12]=1

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 179354262,5-Dioxopyrrolidin-1-yl 3-(tritylthio)propanoateHCID 86626929N1-(3-aminopropyl)-2-methyl-1H-imidazo[4,5-c]quinoline-1,4-diamine hydrochloride

생성물 1

HCID 57568669N-{3-[(4-amino-2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)amino]propyl}-3-mercaptopropanamide

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A mixture of N1-(3-aminopropyl)-2-methyl-1H-imidazo[4,5-c]quinoline-1,4-diamine hydrochloride (1.00 g, 3.26 mmol), succinimido 3-(triphenylmethylthio)propanoate (A. Bray et. al. Aust. J. Chem. 1990, 43, 629-634; 2.22 g, 4.89 mmol), triethylamine (0.45 mL, 3.26 mmol), dichloromethane (33 mL), and methanol (15 mL) was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure and the residue was purified by flash chromatography on silica gel (gradient elution with a solution of 2% ammonium hydroxide in methanol and chloroform). The purified compound was treated with trifluoroacetic acid (3 mL) and triethylsilane (2 mL) in dichloromethane (30 mL) at room temperature overnight. More trifluoroacetic acid was added and after an additional day the reaction was complete. The reaction 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) to yield 327 mg of N-{3-[(4-amino-2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)amino]propyl}-3-mercaptopropanamide. MS (ESI) m/z 359 (M+H)+.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by flash chromatography on silica gel (
  3. washgradient elution with a solution of 2% ammonium hydroxide in methanol and chloroform)
  4. additionThe purified compound was treated with trifluoroacetic acid (3 mL) and triethylsilane (2 mL) in dichloromethane (30 mL) at room temperature overnight
  5. additionMore trifluoroacetic acid was added and after an additional day the reaction
  6. concentrationThe reaction mixture was concentrated under reduced pressure
  7. custompurified by flash chromatography on silica gel (
  8. washgradient elution with a solution of 2% ammonium hydroxide in methanol and chloroform)

출처 및 근거

ORD 기록
ord-1f25219a32614524821707a7c932a533
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08951528B2

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