Ethyl Acetate → 5-{[(1-Aminocyclohexyl)methyl]amino}-6-ethyl-3-{[3-(methylsulfonyl)phenyl]amino}pyrazine-2-carboxamide

HRID 869268Notes

Reaction equation

Cl[C:2]1[N:3]=[C:4]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([S:20]([CH3:23])(=[O:22])=[O:21])[CH:15]=2)[C:5]([C:10]([NH2:12])=[O:11])=[N:6][C:7]=1[CH2:8][CH3:9].[NH2:24][CH2:25][C:26]1([NH2:32])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.CN1C(=O)CCC1.C(OCC)(=O)C>O>[NH2:32][C:26]1([CH2:25][NH:24][C:2]2[N:3]=[C:4]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([S:20]([CH3:23])(=[O:22])=[O:21])[CH:15]=3)[C:5]([C:10]([NH2:12])=[O:11])=[N:6][C:7]=2[CH2:8][CH3:9])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of 5-chloro-6-ethyl-3-{[3-(methylsulfonyl)phenyl]amino}pyrazine-2-carboxamide (Preparation Example 353) (150 mg), 1-(aminomethyl)cyclohexaneamine (163 mg) and NMP (1 mL) was heated at 180° C. for 20 minutes using a microwave reaction system. The reaction liquid was cooled, and ethyl acetate and water were added and stirred for 30 minutes. Thereafter, the precipitated powder was collected by filtration. This powder was heated with ethanol-water (1:1) and washed to give 5-{[(1-aminocyclohexyl)methyl]amino}-6-ethyl-3-{[3-(methylsulfonyl)phenyl]amino}pyrazine-2-carboxamide (112 mg) as a white solid.

Workup

customa microwave reaction system
customThe reaction liquid
temperaturewas cooled
filtrationThereafter, the precipitated powder was collected by filtration
temperatureThis powder was heated with ethanol-water (1:1)
washwashed

Sources & evidence

ORD record: ord-c13fa5b3628040a1ac1bebae7bb831a6
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969336B2

Reaction notes

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