Hydrochloric Acid → HCID 10436859, compound

HRID 1293483Notes

Reaction equation

HRID 1293483 reaction equation
[CH2:1]([N:8]1[C:20]2[C:19]([O:21][CH2:22][CH3:23])=[CH:18][CH:17]=[C:16]([C:24]([O:26]C3C=CC([N+]([O-])=O)=CC=3)=O)[C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[C:12]([Cl:36])[CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[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>[Cl:37][C:38]1[CH:39]=[N:40][CH:41]=[C:42]([Cl:45])[C:43]=1[NH:44][C:24]([C:16]1[C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([Cl:36])[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][CH2:22][CH3:23])=[CH:18][CH:17]=1)=[O:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 898884-Amino-3,5-dichloropyridineHCID 69280714HCID 69280714, compound

Product 1

HCID 10436859HCID 10436859, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-nitrophenyl 9-benzyl-6-chloro-1-ethoxy-9H-4-carbazolecarboxylate (31 mg, 0.062 mmoles) and 3,5 dichloro-4-aminopyridine (10.1 mg, 0.062 mmoles) in dry DMF (3 ml), under N2 atmosphere, 60% sodium hydride (5.40 mg, 0.124 mmoles) was added at 25° C. and the reaction mixture was stirred overnight. The reaction mixture was poured into ice-cold water and neutralized with 1N HCl. The compound was extracted with chloroform (3×10 ml), combined the organic layers and washed with water (3×10 ml) and with brine (10 ml). The organic layer was dried over anhydrous sodium sulphate and concentrated to give 22.5 mg of the title compound as an off-white crystalline solid. m. p: 221-223° C.

Workup

  1. extractionThe compound was extracted with chloroform (3×10 ml)
  2. washwashed with water (3×10 ml) and with brine (10 ml)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-be68ee22e83540d1b037432d50c15ad4
Source dataset
uspto-grants-2007_07
Patent number
US07238725B2

Reaction notes

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