Hydrochloric Acid → HCID 10255164, compound

HRID 1293478Notes

Reaction equation

HRID 1293478 reaction equation
[F:1][C:2]1[CH:35]=[CH:34][C:5]([CH2:6][N:7]2[C:19]3[C:18]([O:20][CH3:21])=[CH:17][CH:16]=[C:15]([C:22]([O:24]C4C=CC([N+]([O-])=O)=CC=4)=O)[C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)=[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:22]([C:15]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]([CH2:6][C:5]3[CH:34]=[CH:35][C:2]([F:1])=[CH:3][CH:4]=3)[C:19]=2[C:18]([O:20][CH3:21])=[CH:17][CH:16]=1)=[O:24]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 898884-Amino-3,5-dichloropyridineHCID 69282263HCID 69282263, compound

Product 1

HCID 10255164HCID 10255164, compoundYield 28.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-Nitrophenyl 9-(4-fluoro benzyl)-1-methoxy-9H-4-carbazole carboxylate (50 mg, 0.106 mmoles) in dry DMF (4 ml) under nitrogen atmosphere, 3,5dichloro-4-amino pyridine (17.34 mg, 0.106 mmoles) was added followed by sodium hydride (60% suspension, 8.5 mg, 0.212 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 15 mg of the title compound as an off white solid, m.p: 222-225° 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-16cc12fd0bec4e0cbdeeb044b2bb7bd1
Source dataset
uspto-grants-2007_07
Patent number
US07238725B2

Reaction notes

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