Water → HCID 69298125, compound

HRID 1430441Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:21])=[C:6]([C:8]2[C:9](=[O:20])[N:10]([CH3:19])[C:11]3[C:16]([CH:17]=2)=[CH:15][N:14]=[C:13](Cl)[CH:12]=3)[CH:7]=1.[CH3:22][O:23][C:24]1[CH:32]=[CH:31][C:27]([CH2:28]CN)=[CH:26][CH:25]=1.C1CCN2[C:36](=[N:37]CCC2)CC1.O>CN1C(=O)CCC1>[CH3:22][O:23][C:24]1[CH:25]=[CH:26][C:27]([CH2:28][N:37]([CH3:36])[C:13]2[CH:12]=[C:11]3[C:16]([CH:17]=[C:8]([C:6]4[CH:7]=[C:2]([NH2:1])[CH:3]=[CH:4][C:5]=4[Cl:21])[C:9](=[O:20])[N:10]3[CH3:19])=[CH:15][N:14]=2)=[CH:31][CH:32]=1

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of 3-(5-amino-2-chlorophenyl)-7-chloro-1-methyl-1,6-naphthyridin-2(1H)-one (5 g, 15.67 mmol), 4-methoxybenzylmethylamine (3.6 g, 23.5 mmol) and DBU (3.7 g, 23.5 mmol) in NMP (80 mL) was heated at 180° C. under N2 for 4 h. The reaction was cooled to RT and poured into water (600 mL). The precipitate was collected by filtration and dried in vacuo to give 7-((4-methoxybenzyl)(methyl)amino)-3-(5-amino-2-chlorophenyl)-1-methyl-1,6-naphthyridin-2(1H)-one (6.5 g, 95% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.46 (s, 1H), 7.68 (s, 1H), 7.16 (d, J=8.8 Hz, 2H), 7.06 (d, J=8.4 Hz, 1H), 6.85 (d, J=8.8 Hz, 2H), 6.54-6.51 (m, 2H), 6.29 (s, 1H), 5.23 (s, 2H), 4.85 (s, 2H), 3.69 (s, 3H), 3.51 (s, 3H), 3.07 (s, 3H).

Workup

temperatureThe reaction was cooled to RT
filtrationThe precipitate was collected by filtration
customdried in vacuo

Sources & evidence

ORD record: ord-97f45348894c4ac8b4ba3dec81d88cbf
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940756B2

Reaction notes

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