Water → HCID 89647619, compound

HRID 1399797Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][CH:11]=2)[C:5]([N+:20]([O-:22])=[O:21])=[CH:4][CH:3]=1.[NH:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[O:26]1[CH2:27][CH2:28][N:23]([C:2]2[N:7]=[C:6]([NH:8][CH2:9][C:10]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH:13]=[CH:12][CH:11]=3)[C:5]([N+:20]([O-:22])=[O:21])=[CH:4][CH:3]=2)[CH2:24][CH2:25]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 6-chloro-N-(naphthalen-1-ylmethyl)-3-nitropyridin-2-amine (3.21 g, 10.2 mmol), morpholine (2.66 g, 30.6 mmol) and K2CO3 (2.11 g, 15.3 mmol) in DMF (50 mL) was stirred at 80° C. for 1 h. It was cooled to room temperature and poured into water (300 mL). It was extracted with EA (300 mL×2). The combined organic layers were washed with brine (300 mL×3), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel eluted with EtOAc/Pet ether=1/1 to afford the desired product as a yellow solid (3.56 g, 96%); LC/MS: MS (ES+) m/e 365 (MH+); 1H NMR (300 MHz, DMSO-d6) δ ppm 3.53 (t, J=4.2 Hz, 4H), 3.60 (t, J=4.2 Hz, 4H), 5.19 (d, J=5.7 Hz, 2H), 6.33 (d, J=9.6 Hz, 1H), 7.44-7.61 (m, 4H), 7.85 (d, J=7.5 Hz, 1H), 7.97 (d, J=7.5 Hz, 1H), 8.12 (d, J=9.6 Hz, 1H), 8.21 (d, J=7.5 Hz, 1H), 9.25 (t, J=5.7 Hz, 1H).

Workup

temperatureIt was cooled to room temperature
extractionIt was extracted with EA (300 mL×2)
washThe combined organic layers were washed with brine (300 mL×3)
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by chromatography on silica gel
washeluted with EtOAc/Pet ether=1/1

Sources & evidence

ORD record: ord-973a8a46d130456db739b8252d6e640c
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906910B2

Reaction notes

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