Cyclopropylamine → 2-(4-Amino-phenyl)-6-cyclopropylamino-7-fluoro-2H-isoquinolin-1-one

HRID 1593047Notes

Reaction equation

HRID 1593047 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]([C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=3)[C:9]2=[O:12])=[CH:4][C:3]=1OS(C(F)(F)F)(=O)=O.[CH:30]1([NH2:33])[CH2:32][CH2:31]1>>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]([N:8]2[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][C:2]([F:1])=[C:3]([NH:33][CH:30]4[CH2:32][CH2:31]4)[CH:4]=3)[C:9]2=[O:12])=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 69828CyclopropylamineHCID 58998446Trifluoromethanesulfonic acid 7-fluoro-2-(4-nitro-phenyl)-1-oxo-1,2-dihydro-isoquinolin-6-yl ester

Product 1

HCID 589984302-(4-Amino-phenyl)-6-cyclopropylamino-7-fluoro-2H-isoquinolin-1-one

Procedure

An analogous C—N coupling procedure to that described in Example 7 was performed on trifluoro-methanesulfonic acid 7-fluoro-2-(4-nitro-phenyl)-1-oxo-1,2-dihydro-isoquinolin-6-yl ester (Example 6) using cyclopropylamine as the nucleophile. Reduction of the nitro group was effected using the procedure outlined in Example 9. ES-MS (M+H)+=310.

Sources & evidence

ORD record
ord-3e223fbcb8e84e298cbbc30a1cf91ba4
Source dataset
uspto-grants-2007_11
Patent number
US07294635B2

Reaction notes

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