Hydrochloric Acid → HCID 58905490, compound

HRID 1293477Notes

Reaction equation

HRID 1293477 reaction equation
[CH3:1][O:2][C:3]1[CH:37]=[CH:36][C:6]([CH2:7][N:8]2[C:20]3[C:19]([O:21][CH3:22])=[CH:18][CH:17]=[C:16]([C:23](OC4C=CC([N+]([O-])=O)=CC=4)=[O:24])[C:15]=3[C:14]3[C:9]2=[CH:10][CH:11]=[C:12]([Cl:35])[CH:13]=3)=[CH:5][CH:4]=1.[Cl:38][C:39]1[CH:40]=[N:41][CH:42]=[C:43]([Cl:46])[C:44]=1[NH2:45].[H-].[Na+].Cl>CN(C=O)C.O>[Cl:38][C:39]1[CH:40]=[N:41][CH:42]=[C:43]([Cl:46])[C:44]=1[NH:45][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]([CH2:7][C:6]3[CH:36]=[CH:37][C:3]([O:2][CH3:1])=[CH:4][CH:5]=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 69280695HCID 69280695, compound

Product 1

HCID 58905490HCID 58905490, compoundYield 47.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-Nitrophenyl 9-(4-methoxy benzyl)-6-chloro-1-methoxy-4-carbazole carboxylate (95 mg, 0.232 mmoles) in dry DMF (5 ml) under nitrogen atmosphere, 3,5-dichloro-4-amino pyridine (37.8 mg, 0.232 mmoles) was added followed by sodium hydride (60% suspension, 20.0 mg, 0.464 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 60 mg of the title compound as an off white solid, m. p: 257-258° 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-75eceb60c7a44820844668f4ce578659
Source dataset
uspto-grants-2007_07
Patent number
US07238725B2

Reaction notes

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