Methanol → N-(2-{[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]oxy}ethyl)-3-mercaptopropanamide

HRID 1845729ノート

反応式

HRID 1845729 の反応式
[NH2:1][CH2:2][CH2:3][O:4][N:5]1[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:18])[C:8]=2[N:7]=[C:6]1[CH2:19][O:20][CH2:21][CH3:22].C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[S:30][CH2:31][CH2:32][C:33](ON2C(=O)CCC2=O)=[O:34])C=CC=CC=1.CO>ClCCl>[NH2:18][C:9]1[C:8]2[N:7]=[C:6]([CH2:19][O:20][CH2:21][CH3:22])[N:5]([O:4][CH2:3][CH2:2][NH:1][C:33](=[O:34])[CH2:32][CH2:31][SH:30])[C:17]=2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1

参加物

5

反応物 3

HCID 887MethanolHCID 179354262,5-Dioxopyrrolidin-1-yl 3-(tritylthio)propanoateHCID 689307621-(2-aminoethoxy)-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-4-amine

生成物 1

HCID 57568678N-(2-{[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]oxy}ethyl)-3-mercaptopropanamide収率 46.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

A solution of 1-(2-aminoethoxy)-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-4-amine (30 mg, 0.10 mmol) and succinimido 3-(triphenylmethylthio)propanoate (54 mg, 0.12 mmol) in dichloromethane (1 mL) was stirred for 24 hours at room temperature. Methanol (1 mL) was added and stirring was continued for another 5 days. The mixture was filtered and the filtrate was concentrated. The residue was dissolved in dichloromethane (2 mL) and triethylsilane (0.16 mL) and cooled to 0° C. Trifluoroacetic acid (0.4 mL) was added. The solution was stirred for 30 min; then it was concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel (gradient elution with a solution of 2% ammonium hydroxide in methanol and chloroform) to provide 18.2 mg of N-(2-{[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]oxy}ethyl)-3-mercaptopropanamide as a solid. HRMS (ESI) calcd for C18H24N5O3S+H 390.1600, found 390.1579.

後処理

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in dichloromethane (2 mL)
  4. additionTrifluoroacetic acid (0.4 mL) was added
  5. stirringThe solution was stirred for 30 min
  6. concentrationthen it was concentrated under reduced pressure
  7. customThe crude product was purified 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-72f9f92e5e62455bb08f7114b9d61087
出典データセット
uspto-grants-2015_02
特許番号
US08951528B2

反応ノート

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