6-(Morpholino)pyridin-3-amine → HCID 11503141, compound

HRID 729273Notes

Reaction equation

HRID 729273 reaction equation
[C:1]([N:5]1[C:9](=[O:10])[C:8](Cl)=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:6]1(=[O:19])=[O:18])([CH3:4])([CH3:3])[CH3:2].[N:20]1([C:26]2[N:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=2)[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1>CC#N>[C:1]([N:5]1[C:9](=[O:10])[C:8]([NH:32][C:29]2[CH:30]=[N:31][C:26]([N:20]3[CH2:21][CH2:22][O:23][CH2:24][CH2:25]3)=[CH:27][CH:28]=2)=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:6]1(=[O:19])=[O:18])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 1040596-(Morpholino)pyridin-3-amineHCID 672426272-tert-Butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide

Product 1

HCID 11503141HCID 11503141, compoundYield 17.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-tert-butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide (0.150 g, 0.50 mmol), 6-morpholin-4-ylpyridin-3-amine (0.108 g, 0.60 mmol) and TEA (0.06 mL, 0.60 mmol) in MeCN (2 mL) was heated at 140° C. for 1 h in a microwave reactor. The mixture was evaporated and the residue was purified by silica gel column chromatography using a 3:1 mixture of EtOAc and petroleum ether as eluant, to give the title compound (0.038 g, 17%) as a solid; 1H NMR (500 MHz, CDCl3): δ 7.81 (d, 1H), 7.24-7.1.5 (m, 1H), 7.14-7.10 (m, 4H), 6.94 (s, 1H), 6.72 (dd, 1H), 6.12 (d, 1H), 3.75 (t, 4H), 3.33 (t, 4H), 1.77 (s, 9H); 13C NMR (125 MHz, CDCl3): δ 159.9, 157.5, 142.9, 131.6, 131.9, 130.0, 129.1, 128.3, 124.7, 124.2, 110.2, 105.9, 66.7, 62.1, 46.1, 27.9; Mass Spectrum: M+H+ 443.

Workup

  1. customThe mixture was evaporated
  2. customthe residue was purified by silica gel column chromatography
  3. additiona 3:1 mixture of EtOAc and petroleum ether as eluant

Sources & evidence

ORD record
ord-35973e9abfbf433baf87f1140f5ce752
Source dataset
uspto-grants-2009_09
Patent number
US07582629B2

Reaction notes

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