Triethylamine → HCID 59497152, compound

HRID 389061Notes

Reaction equation

HRID 389061 reaction equation
C(N(CC)CC)C.[OH:8][N:9]1[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]2[C:10]1=[O:19].Cl.Cl[CH2:22][C:23]1[S:24][C:25]2[C:34]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[N:28]=[C:27]([NH2:35])[C:26]=2[N:36]=1>CN(C)C=O>[NH2:35][C:27]1[C:26]2[N:36]=[C:23]([CH2:22][O:8][N:9]3[C:10](=[O:19])[C:11]4[C:12](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]3=[O:14])[S:24][C:25]=2[C:34]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[N:28]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10665N-HydroxyphthalimideHCID 67542708HCID 67542708, compound

Product 1

HCID 59497152HCID 59497152, compoundYield 49.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triethylamine (7.3 mL, 52 mmol) was added to a solution of N-hydroxyphthalimide (3.42 g, 21.0 mmol) in N,N-dimethylformamide (DMF) (50 mL). 2-(Chloromethyl)[1,3]thiazolo[4,5-c]quinolin-4-amine hydrochloride (5.0 g, 18 mmol) was added to the resulting deep red solution, and the reaction was stirred overnight at ambient temperature. A precipitate formed and was isolated by filtration, washed with dichloromethane, and dried in a vacuum oven to provide 3.34 g of 2-[(4-amino[1,3]thiazolo[4,5-c]quinolin-2-yl)methoxy]-1H-isoindole-1,3(2H)-dione as a tan solid. The filtrate was concentrated under reduced pressure, and the residue was mixed with dichloromethane, filtered, washed with dichloromethane, and dried in a vacuum oven overnight to provide an additional 2.06 g of product.

Workup

  1. customA precipitate formed
  2. customwas isolated by filtration
  3. washwashed with dichloromethane
  4. customdried in a vacuum oven

Sources & evidence

ORD record
ord-0b7fb9c610174c97b9243cd5c2b8419e
Source dataset
uspto-grants-2013_02
Patent number
US08378102B2

Reaction notes

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