3,5-Dichlorophenyl isocyanate → N-(3,5-Dichlorophenyl)-2-(4-isopropyl-1,8-naphthyridin-2-yl)hydrazinecarboxamide

HRID 1892261Notes

Reaction equation

HRID 1892261 reaction equation
[NH:1]([C:3]1[CH:12]=[C:11]([CH:13]([CH3:15])[CH3:14])[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1)[NH2:2].[Cl:16][C:17]1[CH:18]=[C:19]([N:24]=[C:25]=[O:26])[CH:20]=[C:21]([Cl:23])[CH:22]=1>>[Cl:16][C:17]1[CH:18]=[C:19]([NH:24][C:25]([NH:2][NH:1][C:3]2[CH:12]=[C:11]([CH:13]([CH3:15])[CH3:14])[C:10]3[C:5](=[N:6][CH:7]=[CH:8][CH:9]=3)[N:4]=2)=[O:26])[CH:20]=[C:21]([Cl:23])[CH:22]=1

Participants

3

Reactant 2

HCID 944603,5-Dichlorophenyl isocyanateHCID 670830372-Hydrazinyl-4-isopropyl-1,8-naphthyridine

Product 1

HCID 52912016N-(3,5-Dichlorophenyl)-2-(4-isopropyl-1,8-naphthyridin-2-yl)hydrazinecarboxamide

Procedure

A 100 mg (0.5 mmol) sample of 2-hydrazinyl-4-isopropyl-1,8-naphthyridine and 94 mg (1.0 eq) of 3,5-dichlorophenyl isocyanate were reacted as outlined in Scheme 1 above to give the desired title compound. Spectroscopic data: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.23 (d, J=6.74 Hz, 6 H) 3.56 (d, J=6.74 Hz, 1 H) 6.82 (s, 1 H) 7.04 (t, J=1.76 Hz, 1 H) 7.23 (dd, J=8.20, 4.40 Hz, 1 H) 7.59 (br. s., 2 H) 8.31 (d, J=1.47 Hz, 1 H) 8.54 (br. s., 1 H) 8.66 (d, J=1.17 Hz, 1 H) 8.99 (br. s., 1 H) 9.25 (br. s., 1 H).

Sources & evidence

ORD record
ord-8dcb91d716b14257a9fc3f2f7f74563a
Source dataset
uspto-grants-2013_08
Patent number
US08507682B2

Reaction notes

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