Phosgene → HCID 22337589, compound

HRID 586074Notes

Reaction equation

HRID 586074 reaction equation
[CH3:1][N:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([NH2:11])[C:5]=2[CH:4]=[N:3]1.[C:12](Cl)(Cl)=[O:13].[Cl:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][NH2:22])=[CH:19][CH:18]=1>C1(C)C=CC=CC=1>[Cl:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][NH:22][C:12]([NH:11][C:6]2[CH:7]=[CH:8][CH:9]=[C:10]3[C:5]=2[CH:4]=[N:3][N:2]3[CH3:1])=[O:13])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 660364-ChlorobenzylamineHCID 1538381H-Indazol-4-amine, 1-methyl-

Product 1

HCID 22337589HCID 22337589, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-Methyl-1H-indazol-4-amine (1.00 g, 6.8 mmol) in toluene (225 mL) was treated with phosgene (20% in toluene, 7 ml, 13.2 mmol). The mixture was heated at reflux for 3 hours, cooled, and the solvent removed under reduced pressure. The residue was taken in diethyl ether (100 ml) and triethyl amine (6 ml), and filtered. The filtrate was treated with 4-chlorobenzylamine (963 mg, 6.8 mmol). After stirring at ambient temperature for 16 hours, the solvent was reduced to half volume under reduced pressure, filtered, and the filter cake washed with diethyl ether:hexanes (1:1) to provide the title compound. The title compound was treated with HCl/ethanol and evaporated to dryness to provide the hydrochloride. 1H NMR (DMSO-d6) δ 9.25 (s, 1H), 8.25 (s, 1H), 7.68 (d, 1H), 7.39 (m, 5H), 7.24 (t, 1H), 7.13 (d, 1H), 4.34 (s, 2H), 3.99 (s, 3H); MS (ESI) m/z 315 (M+H)+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 hours
  3. temperaturecooled
  4. customthe solvent removed under reduced pressure
  5. filtrationtriethyl amine (6 ml), and filtered
  6. filtrationfiltered
  7. washthe filter cake washed with diethyl ether:hexanes (1:1)

Sources & evidence

ORD record
ord-4eebb30375914cf2b2346e62fb2cd00e
Source dataset
uspto-grants-2005_08
Patent number
US06933311B2

Reaction notes

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