3,5-Dichlorophenyl isocyanate → HCID 52912015, compound

HRID 1892255Notes

Reaction equation

HRID 1892255 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-c44b31e945a1477090099026f1e1a56b
Source dataset
uspto-grants-2013_08
Patent number
US08507682B2

Reaction notes

Loading…