(3-Amino-6-(5-quinolyl)pyrazin-2-yl)[(4-methoxyphenyl)methyl]amine → 5-(Quinolin-5-YL)-1H-imidazo[4,5-B]pyrazin-2(3H)-one

HRID 388088Notes

Reaction equation

[N:1]1[C:10]2[C:5](=[C:6]([C:11]3[N:12]=[C:13]([NH2:18])[C:14]([NH2:17])=[N:15][CH:16]=3)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.NC1C(NCC2C=C[C:41]([O:44]C)=CC=2)=NC(C2C=CC=C3C=2C=CC=N3)=CN=1>FC(F)(F)C(O)=O.ClCCl.C1(S)C=CC=CC=1>[N:1]1[C:10]2[C:5](=[C:6]([C:11]3[N:12]=[C:13]4[NH:18][C:41](=[O:44])[NH:17][C:14]4=[N:15][CH:16]=3)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 70 °C

Procedure

5-(5-Quinolyl)pyrazine-2,3-diamine. (3-Amino-6-(5-quinolyl)pyrazin-2-yl)[(4-methoxy phenyl)methyl]amine (see Example 1.B) (0.210 g, 0.588 mmol) was dissolved in trifluoroacetic acid/dichloromethane (2 mL:2 mL) with PS-thiophenol as a scavenger. The solution was heated to 70° C. in a sealed tube for two hours and then concentrated under reduced pressure and diluted with methanol. The methanol/product solution was filtered through a Phenomenex Strata-X-C solid phase extraction column to remove TFA. Additional water was added to the eluted compound to induce precipitation. The precipitate was filtered and dried under vacuum to afford the title compound (0.080 g, 57% yield). MS (ESI) m/z 238.1 [M+1]+.

Workup

concentrationconcentrated under reduced pressure
additiondiluted with methanol
filtrationThe methanol/product solution was filtered through a Phenomenex Strata-X-C solid phase extraction column
customto remove TFA
additionAdditional water was added to the eluted compound
customprecipitation
filtrationThe precipitate was filtered
customdried under vacuum

Sources & evidence

ORD record: ord-28929697d25242f9a895cf667eabe9e4
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372976B2

Reaction notes

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