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

HRID 1845719ノート

反応式

HRID 1845719 の反応式
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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-1f25219a32614524821707a7c932a533
出典データセット
uspto-grants-2015_02
特許番号
US08951528B2

反応ノート

読み込み中…