Cyanogen Bromide → HCID 86626303, compound

HRID 1097595Notes

Reaction equation

[NH2:1][C:2]1[C:3]([Cl:25])=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:9][CH:8]=[CH:7][CH:6]=2.[N:26]#[C:27]Br>C(O)C>[NH2:26][C:27]1[N:12]([CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[C:3]([Cl:25])[C:2]=2[N:1]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A solution of tert-butyl 4-[(3-amino-2-chloroquinolin-4-yl)amino]butylcarbamate (Nanba et al, U.S. Pat. No. 6,069,149, Example 14, 9.5 g, 26 mmol) in ethanol (100 mL) was heated to 110° C.; cyanogen bromide (2.98 g, 28.6 mmol) was added. The reaction was stirred for three hours at 110° C., and an analysis by LC/MS indicated the presence of starting material. Additional cyanogen bromide (0.55 equivalent) was added, and the reaction was stirred for three days at 110° C. and allowed to cool to room temperature. Most of the solvent was removed under reduced pressure, and 2 N aqueous sodium hydroxide (500 mL) was added. The mixture was stirred for 30 minutes, and ethyl acetate (400 mL) was added. A precipitate formed and was isolated by filtration to provide 7.188 g of tert-butyl 4-(2-amino-4-chloro-1H-imidazo[4,5-c]quinolin-1-yl)butylcarbamate as a cream-colored solid.

Workup

stirringthe reaction was stirred for three days at 110° C.
temperatureto cool to room temperature
customMost of the solvent was removed under reduced pressure, and 2 N aqueous sodium hydroxide (500 mL)
additionwas added
stirringThe mixture was stirred for 30 minutes
additionethyl acetate (400 mL) was added
customA precipitate formed
customwas isolated by filtration

Sources & evidence

ORD record: ord-d53cfca97b764de9bfd178146f6f9877
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143270B2

Reaction notes

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