4-Aminopyridine → HCID 58905492, compound

HRID 1293480Notes

Reaction equation

HRID 1293480 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][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)=[O:23])[C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[NH2:31][C:32]1[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl.CN(C=O)C>[N:35]1[CH:36]=[CH:37][C:32]([NH:31][C:22]([C:15]2[C:14]3[C:13]4[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=4)[N:7]([CH2:6][C:5]4[CH:25]=[CH:26][C:2]([F:1])=[CH:3][CH:4]=4)[C:19]=3[C:18]([O:20][CH3:21])=[CH:17][CH:16]=2)=[O:23])=[CH:33][CH:34]=1

Participants

7

Reactant 4

HCID 17274-AminopyridineHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 69280107HCID 69280107, compound

Product 1

HCID 58905492HCID 58905492, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6212ChloroformSolvent2×

Procedure

To a suspension of 9-(4-fluoro benzyl)-1-methoxy 9H-4-carbazole carboxylicacid (100 mg, 0.286 mmoles) in dry chloroform (15 ml), thionyl chloride (0.063 ml, 0.86 mmoles) was added followed by 2 drops of dry DMF and the reaction mixture was sired under nitrogen atmosphere for two hours. Solvent and the excess thionyl chloride were evaporated from the reaction mixture and dried under vacuum. To this residue, dry chloroform (15 ml) was added followed by 4-aminopyridine (27 mg, 0.286 mmoles) and triethylamine (0.06 ml, 0.43 mmoles) were added and the reaction mixture was stirred under nitrogen atmosphere for 17 hours. The reaction mixture was diluted with chloroform (30 ml) and washed with water (2×10 ml). The organic layer was washed with brine (20 ml), dried over Na2SO4 and concentrated to give 45 mg of the title product as pale yellow solid, m.p: 230-232° C.

Workup

  1. additionwas added
  2. customSolvent and the excess thionyl chloride were evaporated from the reaction mixture
  3. customdried under vacuum
  4. additionTo this residue, dry chloroform (15 ml) was added
  5. additionwere added
  6. washwashed with water (2×10 ml)
  7. washThe organic layer was washed with brine (20 ml)
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-45b94b17e188493a9a3f4a91510c768e
Source dataset
uspto-grants-2007_07
Patent number
US07238725B2

Reaction notes

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