1,1'-Thiocarbonyldi-2(1H)-pyridone → 3-(5-isothiocyanato-2-methylphenyl)-1,7-dimethyl-1,6-naphthyridin-2(1H)-one

HRID 2061160Notes

Reaction equation

HRID 2061160 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:21])=[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]([CH3:18])[CH:12]=3)[CH:7]=1.[C:22](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:23]>C(Cl)Cl>[N:1]([C:2]1[CH:3]=[CH:4][C:5]([CH3:21])=[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]([CH3:18])[CH:12]=3)[CH:7]=1)=[C:22]=[S:23]

Participants

4

Reactant 2

HCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 592123103-(5-amino-2-methylphenyl)-1,7-dimethyl-1,6-naphthyridin-2(1H)-one

Product 1

HCID 583690043-(5-isothiocyanato-2-methylphenyl)-1,7-dimethyl-1,6-naphthyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(5-amino-2-methylphenyl)-1,7-dimethyl-1,6-naphthyridin-2(1H)-one 15 (280 mg, 1 mmol) in DCM (5 mL) was added 1,1′-thiocarbonyldipyridin-2(1H)-one (233 mg, 1 mmol) at rt. The solvent was removed in vacuo after 1 h. The crude white solid of 3-(5-isothiocyanato-2-methylphenyl)-1,7-dimethyl-1,6-naphthyridin-2(1H)-one 19 was used without further purification. 1H NMR (400 MHz, CDCl3) δ 8.64 (s, 1H), 7.18 (d, J=8.0 Hz, 1H), 7.09 (dd, J=2.4, 8.0 Hz, 1H), 7.05 (d, J=2 Hz, 1H), 7.04 (s, 1H), 3.66 (s, 3H), 2.64 (s, 3H), 2.16 (s, 3H). MS m/z 322.2 (M+1).

Workup

  1. customThe solvent was removed in vacuo after 1 h
  2. customThe crude white solid of 3-(5-isothiocyanato-2-methylphenyl)-1,7-dimethyl-1,6-naphthyridin-2(1H)-one 19 was used without further purification

Sources & evidence

ORD record
ord-731e49857f9b4d66b4b7fbcb0d38d9eb
Source dataset
uspto-grants-2012_10
Patent number
US08278452B2

Reaction notes

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