Triethylamine → 9-bromo-1-chloro-N-[(1-methyl-1H-pyrazol-3-yl)methyl]benzo[c]-1,6-naphthyridin-6-amine

HRID 2192969Notes

Reaction equation

[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[C:6](Cl)=[N:7][C:8]3[C:13]([C:4]=2[CH:3]=1)=[C:12]([Cl:14])[N:11]=[CH:10][CH:9]=3.[CH3:18][N:19]1[CH:23]=[CH:22][C:21]([CH2:24][NH2:25])=[N:20]1.CCN(CC)CC>CC#N.CCOC(C)=O>[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[C:6]([NH:25][CH2:24][C:21]3[CH:22]=[CH:23][N:19]([CH3:18])[N:20]=3)=[N:7][C:8]3[C:13]([C:4]=2[CH:3]=1)=[C:12]([Cl:14])[N:11]=[CH:10][CH:9]=3

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 9-bromo-1,6-dichloro-benzo[c][1,6]naphthyridine (0.10 g, 0.31 mMol) in anhydrous CH3CN (4.0 mL) was added C-(1-methyl-1H-pyrazol-3-yl)-methylamine (0.040 g 0.36 mMol) and anhydrous Et3N (0.22 mL, 1.6 mMol). The reaction mixture was heated in a sealed tube at 120° C. After 3 hours the solvent was removed and the solid obtained was re-dissolved in EtOAc (10 mL). The EtOAc layer was washed with water (2×5 mL), brine (1×10 mL), and dried over MgSO4. The filtrate was concentrated and the resulting residue was purified using preparative HPLC to afford 9-bromo-1-chloro-N-[(1-methyl-1H-pyrazol-3-yl)methyl]benzo[c]-1,6-naphthyridin-6-amine. 1H NMR (400 MHz, DMSO-d6) 11.34 (br d, 1H), 10.11 (d, 1H), 8.61 (t, 1H), 8.32 (d, 1H), 7.75-7.73 (dd, 1H), 7.55 (d, 1H), 7.37 (t, 1H), 6.40 (d, 1H), 6.18 (d, 1H), 4.74 (d, 2H), 3.77 (s, 3H). LRMS calculated for C17H14BrClN5 [M+H]+, 404.0; found 403.9.

Workup

customAfter 3 hours the solvent was removed
customthe solid obtained
washThe EtOAc layer was washed with water (2×5 mL), brine (1×10 mL)
dry with materialdried over MgSO4
concentrationThe filtrate was concentrated
customthe resulting residue was purified

Sources & evidence

ORD record: ord-c0e1bb76d52c4dd088ae7e359f879bc7
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329722B2

Reaction notes

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