Dimethylformamide → HCID 178453050, compound

HRID 415476Notes

Reaction equation

HRID 415476 reaction equation
CN([CH:4]=[O:5])C.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:18][C:19]1[C:20]([Cl:46])=[N:21][C:22]2[C:27]([C:28]=1[NH:29][CH2:30][C:31]1[CH:32]=[C:33]([CH:43]=[CH:44][CH:45]=1)[CH2:34][NH:35][C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[CH:26][CH:25]=[CH:24][CH:23]=2>N1C=CC=CC=1>[Cl:46][C:20]1[C:19]2[N:18]=[C:4]([OH:5])[N:29]([CH2:30][C:31]3[CH:32]=[C:33]([CH:43]=[CH:44][CH:45]=3)[CH2:34][NH:35][C:36](=[O:42])[O:37][C:38]([CH3:40])([CH3:41])[CH3:39])[C:28]=2[C:27]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[N:21]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 682631,1'-CarbonyldiimidazoleHCID 86633723Tert-butyl 3-{[(3-amino-2-chloroquinolin-4-yl)amino]methyl}benzylcarbamate

Product 1

HCID 178453050HCID 178453050, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

DMF (150 mL), pyridine (10 mL), and 1,1′-carbonyldiimidazole (16.7 g, 103 mmol) were added to tert-butyl 3-{[(3-amino-2-chloroquinolin-4-yl)amino]methyl}benzylcarbamate (17.03 g, 41.24 mmol), and the reaction was heated at 80° C. overnight and allowed to cool. The volatiles were removed under reduced pressure. The residue was mixed with ethyl acetate, collected by filtration, and dried under vacuum for two hours to provide 12.06 g of tert-butyl 3-[(4-chloro-2-hydroxy-1H-imidazo[4,5-c]quinolin-1-yl)methyl]benzylcarbamate as a white solid.

Workup

  1. temperatureto cool
  2. customThe volatiles were removed under reduced pressure
  3. additionThe residue was mixed with ethyl acetate
  4. filtrationcollected by filtration
  5. customdried under vacuum for two hours

Sources & evidence

ORD record
ord-a5a7c448e5a647c0a818e3881d761fc6
Source dataset
uspto-grants-2012_01
Patent number
US08088790B2

Reaction notes

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