Thionyl Chloride → tert-Butyl 5-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-1,3-dihydro-2H-isoindole-2-carboxylate

HRID 1425036Notes

Reaction equation

HRID 1425036 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:9]([OH:11])=O)[NH:5][C:6]=1[CH2:7][CH3:8].S(Cl)(Cl)=O.[NH2:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[CH2:22][N:21]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:20]2>N1C=CC=CC=1>[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:16][C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[CH2:22][N:21]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:20]3)=[O:11])[NH:5][C:6]=1[CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 22591361tert-butyl 5-amino-2,3-dihydro-1H-isoindole-2-carboxylateHCID 675489294-chloro-5-ethyl-1H-imidazole-2-carboxylic acid

Product 1

HCID 67549798tert-Butyl 5-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-1,3-dihydro-2H-isoindole-2-carboxylateYield 64%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The same operation as in Example (91c) was performed using 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid (410 mg, 2.36 mmol), thionyl chloride (5 mL), tert-butyl 5-amino-1,3-dihydro-2H-isoindole-2-carboxylate (described in Andronati, S. A.; Krys'ko, A. A.; Chugunov, B. M.; Kabanova, T. A.; Artemenko, A. G.; Russ. J. Org. Chem., 42, 8, 2006, 1174-1182, 0.94 g, 4 mmol) and pyridine (5 mL), to obtain 619 mg of the title compound as a white solid (64%).

Sources & evidence

ORD record
ord-274d9d009e4a4f21bc9b9d383184193c
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

Loading…