Hydrochloric Acid → HCID 58905484, compound

HRID 1293475Notes

Reaction equation

HRID 1293475 reaction equation
[CH2:1]([N:8]1[C:20]2[C:19]([O:21][CH3:22])=[CH:18][CH:17]=[C:16]([C:23](OC3C=CC([N+]([O-])=O)=CC=3)=[O:24])[C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[C:12]([Cl:35])[CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:36][C:37]1[CH:38]=[N:39][CH:40]=[C:41]([Cl:44])[C:42]=1[NH2:43].[H-].[Na+].Cl>CN(C=O)C.O>[Cl:36][C:37]1[CH:38]=[N:39][CH:40]=[C:41]([Cl:44])[C:42]=1[NH:43][C:23]([C:16]1[C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([Cl:35])[CH:13]=3)[N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:20]=2[C:19]([O:21][CH3:22])=[CH:18][CH:17]=1)=[O:24]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 898884-Amino-3,5-dichloropyridineHCID 69284365HCID 69284365, compound

Product 1

HCID 58905484HCID 58905484, compoundYield 46.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-Nitrophenyl 9-benzyl-6-chloro-1-methoxy-4-carbazole carboxylate (124 mg, 0.255 mmoles) in dry DMF (3 ml) under nitrogen atmosphere, 3,5-dichloro-4-amino pyridine (41.5 mg, 0.255 mmoles) was added followed by sodium hydride (60% suspension, 16.7 mg, 0.382 mmoles) and the reaction mixture was stirred at room temperature for one hour. Ice pieces were added to the reaction mixture, diluted with water (15 ml) and neutralized with 1N HCl. The precipitated product was filtered, washed with water, dried and purified by column chromatography to give 60 mg of the title compound as an off white solid, m. p: 210-213° C.

Workup

  1. additionIce pieces were added to the reaction mixture
  2. filtrationThe precipitated product was filtered
  3. washwashed with water
  4. customdried
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-6b4e7644c9d243d2be85418d20a1b489
Source dataset
uspto-grants-2007_07
Patent number
US07238725B2

Reaction notes

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