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 1845725Notes

Reaction equation

HRID 1845725 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a53da8b2c16a4fa1b59d6bc8c96f7a23
Source dataset
uspto-grants-2015_02
Patent number
US08951528B2

Reaction notes

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