4-Toluenesulfonyl chloride → 2-(2-{4-amino-2-(2-methoxyethyl)-1-[3-(2-oxopyrrolidin-1-yl)propyl]-1H-imidazo[4,5-c]quinolin-8-yl}ethyl)-1H-isoindole-1,3(2H)dione

HRID 244870Notes

Reaction equation

HRID 244870 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[N:6]([CH2:31][CH2:32][CH2:33][N:34]2[CH2:38][CH2:37][CH2:36][C:35]2=[O:39])[C:7]2[C:16]3[CH:15]=[C:14]([CH2:17][CH2:18][N:19]4[C:27](=[O:28])[C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[C:20]4=[O:29])[CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:30]=1.ClC1C=C(C=CC=1)C(OO)=O.[OH-].[NH4+:52].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>ClCCl>[NH2:52][C:9]1[C:8]2[N:30]=[C:5]([CH2:4][CH2:3][O:2][CH3:1])[N:6]([CH2:31][CH2:32][CH2:33][N:34]3[CH2:38][CH2:37][CH2:36][C:35]3=[O:39])[C:7]=2[C:16]2[CH:15]=[C:14]([CH2:17][CH2:18][N:19]3[C:20](=[O:29])[C:21]4[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:27]3=[O:28])[CH:13]=[CH:12][C:11]=2[N:10]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 690772482-(2-{2-(2-methoxyethyl)-1-[3-(2-oxo-pyrrolidin-1-yl)propyl]-1H-imidazo[4,5-c]quinolin-8-yl}ethyl)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 690766432-(2-{4-amino-2-(2-methoxyethyl)-1-[3-(2-oxopyrrolidin-1-yl)propyl]-1H-imidazo[4,5-c]quinolin-8-yl}ethyl)-1H-isoindole-1,3(2H)dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(2-{2-(2-Methoxyethyl)-1-[3-(2-oxo-pyrrolidin-1-yl)propyl]-1H-imidazo[4,5-c]quinolin-8-yl}ethyl)-1H-isoindole-1,3(2H)-dione (2.1 g, 3.8 mmol) in dichloromethane (75 mL) was combined with 3-chloroperoxybenzoic acid (60% pure, 2.0 g, 7.5 mmol) and the reaction was stirred for 18 hours. Concentrated ammonium hydroxide (40 mL) was added and the mixture was vigorously stirred for an additional 10 minutes. p-Toluenesulfonyl chloride (791 mg, 4.12 mmol) was added and the mixture was stirred for an additional 1 hour. The fractions were separated and aqueous fraction was extracted with chloroform (10×35 mL). The combined organic fractions were sequentially dried (MgSO4), filtered, and concentrated to provide 2.2 g of 2-(2-{4-amino-2-(2-methoxyethyl)-1-[3-(2-oxopyrrolidin-1-yl)propyl]-1H-imidazo[4,5-c]quinolin-8-yl}ethyl)-1H-isoindole-1,3(2H)dione as an off-white foam. MS (APCI) m/z 541 (M+H)+.

Workup

  1. stirringthe mixture was vigorously stirred for an additional 10 minutes
  2. stirringthe mixture was stirred for an additional 1 hour
  3. customThe fractions were separated
  4. extractionaqueous fraction was extracted with chloroform (10×35 mL)
  5. dry with materialThe combined organic fractions were sequentially dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-cb39c0c6d94e4c90a1e2d082cee7173e
Source dataset
uspto-grants-2014_02
Patent number
US08658666B2

Reaction notes

Loading…