Aniline → HCID 178515311, compound

HRID 2253301Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[C:12](=[O:14])[NH:11][C:10](=[O:15])[CH2:9]2)([O-])=O.[NH2:16][C:17]1C=CC=CC=1>>[NH:1]1[C:4]2[C:13]3[C:12](=[O:14])[NH:11][C:10](=[O:15])[CH2:9][C:8]=3[CH:7]=[CH:6][C:5]=2[N:16]=[CH:17]1

Participants

Reactant 2

HCID 6115Aniline

HCID 20385007HCID 20385007, compound

Product 1

HCID 178515311HCID 178515311, compound

Procedure

The general synthesis described in Scheme 1 is similar to the one described in U.S. Pat. No. 4,176,184. Briefly, reduction of 8-nitroisoquinoline-1,3(2H,4H)-dione 1(i) (prepared according to the procedure described in DE 3410168) to the corresponding aniline 1(ii) followed by acylation with acyl chloride and cyclization of the resulting amide gave 1H-imidazol[4,5-h]isoquinoline-7,9(6H,8H)-dione 1 (iii). Alkylation of 1(iii) with 1-bromo-3-chloropropane gave 1(iv), which reacted with a primary amine to give 1(v). If necessary, the transformation of R1a and R3a to R1 and R3 by methods known to the skilled in the art (including, but not limited to, removal of protective group, alkylation, oxidation and reduction) gave the compounds of formula (I) or (Ia).

Workup

customThe general synthesis

Sources & evidence

ORD record: ord-08b18194aeed4a13968d7aa48bd0751e
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07323567B2

Reaction notes

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