Pyridine → HCID 86596424, compound

HRID 746451Notes

Reaction equation

HRID 746451 reaction equation
ClC1C=NC=C(Cl)C=1[NH:8][C:9]([C:11]1[C:23]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20](N)[CH:21]=3)[N:16]([CH3:25])[C:15]=2[C:14]([O:26][CH3:27])=[CH:13][CH:12]=1)=[O:10].[N:29]1C=C[CH:32]=[CH:31][CH:30]=1.C(Cl)(=[O:38])CC>C1COCC1>[CH3:27][O:26][C:14]1[C:15]2[N:16]([CH3:25])[C:17]3[C:22](=[CH:21][C:20]([NH:29][C:30](=[O:38])[CH2:31][CH3:32])=[CH:19][CH:18]=3)[C:23]=2[C:11]([C:9]([NH2:8])=[O:10])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 62324Propionyl chlorideHCID 21105725HCID 21105725, compound

Product 1

HCID 86596424HCID 86596424, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N-(3,5-dichloropyrid-4-yl)-1-methoxy-9-methyl-6-amino-9H-4-carbazolecarboxamide (75 mg, 0.00018 mol) was suspended in THF (5 ml) and added with pyridine (28 mg, 0.00036 mol) and stirred at room temperature for 10 minutes. The solution obtained, was added with a solution of propionyl chloride (24 mg, 0.00027) in dry THF (5 ml). The reaction mixture was stirred for 1 hr. THF was evaporated and the solid was washed with water to get crude solid which was column chromatographed using 10% methanol in chloroform to give N-3,5-dichloropyrid-4-yl)-1-methoxy-9-methyl-6-propionamido-9H-4-carbazolecarboxamide (20 mg), mp>250° C.

Workup

  1. customThe solution obtained
  2. stirringThe reaction mixture was stirred for 1 hr
  3. customTHF was evaporated
  4. washthe solid was washed with water
  5. customto get crude solid which
  6. customchromatographed

Sources & evidence

ORD record
ord-da88fe6034a44365af395bd547f4167e
Source dataset
uspto-grants-2008_07
Patent number
US07393846B2

Reaction notes

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