Dimethylamine → N3,N3-dimethylbenzo[f][1,7]naphthyridine-3,5-diamine

HRID 1259078Notes

Reaction equation

HRID 1259078 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([NH2:16])[N:6]=[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]3=2)[N:3]=1.[CH3:17][NH:18][CH3:19]>>[CH3:17][N:18]([CH3:19])[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([NH2:16])[N:6]=[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]3=2)[N:3]=1

Participants

3

Reactant 2

HCID 674DimethylamineHCID 582136303-Chlorobenzo[f][1,7]naphthyridin-5-amine

Product 1

HCID 58213580N3,N3-dimethylbenzo[f][1,7]naphthyridine-3,5-diamine

Conditions

Temperature
100 °C

Procedure

A solution of 3-chlorobenzo[f][1,7]naphthyridin-5-amine (Example 20) (1.0 eq.) was dissolved in 40% aqueous dimethylamine (0.26 M) and heated in a microwave reactor at 100° C. for 30 minutes. The reaction mixture was concentrated en vacuo, and the residue was purified by a COMBIFLASH® system (ISCO) using 0-90% ethyl acetate in hexane to give N3,N3-dimethylbenzo[f][1,7]naphthyridine-3,5-diamine. 1H NMR (methanol d-4): δ 8.63 (d, 1H), 8.20 (d, 1H), 7.55 (d, 1H), 7.41-7.45 (dd, 1H), 7.29-7.33 (dd, 1H), 7.27 (d, 1H), 3.26 (s, 6H). LRMS [M+H]=239.1

Workup

  1. concentrationThe reaction mixture was concentrated en vacuo
  2. customthe residue was purified by a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-719d2639f5c34d38a91c55b26c9609d0
Source dataset
uspto-grants-2013_06
Patent number
US08466167B2

Reaction notes

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