Hydrochloric Acid → HCID 10075644, compound

HRID 1293476Notes

Reaction equation

HRID 1293476 reaction equation
[F:1][C:2]1[CH:36]=[CH:35][C:5]([CH2:6][N:7]2[C:19]3[C:18]([O:20][CH3:21])=[CH:17][CH:16]=[C:15]([C:22](OC4C=CC([N+]([O-])=O)=CC=4)=[O:23])[C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[C:11]([Cl:34])[CH:12]=3)=[CH:4][CH:3]=1.[Cl:37][C:38]1[CH:39]=[N:40][CH:41]=[C:42]([Cl:45])[C:43]=1[NH2:44].[H-].[Na+].Cl>CN(C=O)C.O>[Cl:37][C:38]1[CH:39]=[N:40][CH:41]=[C:42]([Cl:45])[C:43]=1[NH:44][C:22]([C:15]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([Cl:34])[CH:12]=3)[N:7]([CH2:6][C:5]3[CH:35]=[CH:36][C:2]([F:1])=[CH:3][CH:4]=3)[C:19]=2[C:18]([O:20][CH3:21])=[CH:17][CH:16]=1)=[O:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 898884-Amino-3,5-dichloropyridineHCID 69280117HCID 69280117, compound

Product 1

HCID 10075644HCID 10075644, compoundYield 169.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-Nitrophenyl 9-(4-fluoro benzyl)-6-chloro-1-methoxy-4-carbazole carboxylate (170 mg, 0.4276 mmoles) in dry DMF (6 ml) under nitrogen atmosphere, 3,5-dichloro-4-amino pyridine (69.7 mg, 0.1116 mmoles) was added followed by sodium hydride (60% suspension, 37.0 mg, 0.8553 mmoles) and the reaction mixture was stirred at room temperature for two hours. 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 and dried under vacuum to give 100 mg of the title compound as an off white solid, m. p: 249-250° C.

Workup

  1. additionIce pieces were added to the reaction mixture
  2. filtrationThe precipitated product was filtered
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-2ab064dfdee1438d9ed93b87c62d080d
Source dataset
uspto-grants-2007_07
Patent number
US07238725B2

Reaction notes

Loading…