3,5-Dichlorophenyl isocyanate → HCID 52912015, compound

HRID 2368680Notes

Reaction equation

HRID 2368680 reaction equation
[NH:1]([C:3]1[CH:12]=[C:11]([CH3:13])[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1)[NH2:2].[Cl:14][C:15]1[CH:16]=[C:17]([N:22]=[C:23]=[O:24])[CH:18]=[C:19]([Cl:21])[CH:20]=1>C(Cl)Cl>[Cl:14][C:15]1[CH:16]=[C:17]([NH:22][C:23]([NH:2][NH:1][C:3]2[CH:12]=[C:11]([CH3:13])[C:10]3[C:5](=[N:6][CH:7]=[CH:8][CH:9]=3)[N:4]=2)=[O:24])[CH:18]=[C:19]([Cl:21])[CH:20]=1

Participants

4

Reactant 2

HCID 944603,5-Dichlorophenyl isocyanateHCID 23008691HCID 23008691, compound

Product 1

HCID 52912015HCID 52912015, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-hydrazinyl-4-methyl-1,8-naphthyridine prepared above (84 mg, 0.482 mmol) in CH2Cl2 was added 3,5-dichlorophenyl isocyanate (91 mg, 1.0 eq). The resulting mixture was stirred at room temperature overnight. The resulting precipitate was filtered off and washed with EtOAc to give the desired title compound. Spectroscopic data: 1H NMR (300 MHz, DMSO-d6) δ ppm 2.51 (s, 3 H) 6.78 (s, 1 H) 7.05 (t, J=1.90 Hz, 1 H) 7.23 (dd, J=7.91, 4.40 Hz, 1 H) 7.61 (br. s., 2 H) 8.22 (dd, J=8.06, 1.90 Hz, 1 H) 8.57 (br. s., 1 H) 8.68 (dd, J=4.40, 1.76 Hz, 1 H) 8.98 (s, 1 H) 9.22 (br. s., 1 H).

Workup

  1. filtrationThe resulting precipitate was filtered off
  2. washwashed with EtOAc

Sources & evidence

ORD record
ord-58214235ddc141968304c7536bd52a70
Source dataset
uspto-grants-2014_04
Patent number
US08703797B2

Reaction notes

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