Water → HCID 89648267, compound

HRID 1399801Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 6-chloro-N-(2,3-dichlorobenzyl)-3-nitropyridin-2-amine (3.37 g, 10.1 mmol), morpholine (2.64 g, 30.3 mmol) and K2CO3 (2.09 g, 15.15 mmol) in DMF (50 mL) was stirred at 80° C. for 1 h. The reaction was cooled to room temperature and poured into water (300 mL). It was extracted with EtOAc (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 (3.7 g, 96%); LC/MS: MS (ES+) m/e 383 (MH+); 1H NMR (300 MHz, DMSO-d6) δ ppm 3.54 (s, 4H), 3.56 (s, 4H), 4.81 (d, J=5.7 Hz, 2H), 6.33 (d, J=9.6 Hz, 1H), 7.27-7.34 (m, 2H), 7.53 (dd, J=2.1, 6.9 Hz, 1H), 8.12 (d, J=9.6 Hz, 1H), 9.33 (t, J=6.3 Hz, 1H).

Workup

temperatureThe reaction was cooled to room temperature
extractionIt was extracted with EtOAc (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-d4411a26b8924da39abd63569d192ac3
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906910B2

Reaction notes

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