Pyridine → HCID 86596421, compound

HRID 131611Notes

Reaction equation

HRID 131611 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]([NH2:24])[CH:21]=3)[N:16]([CH3:25])[C:15]=2C(OC)=C[CH:12]=1)=[O:10].N1C=CC=C[CH:30]=1.[C:35](Cl)(=[O:37])[CH3:36].C1C[O:42][CH2:41][CH2:40]1>>[CH3:30][O:37][C:35]1[C:15]2[N:16]([CH3:25])[C:17]3[C:22](=[CH:21][C:20]([NH:24][C:41](=[O:42])[CH3:40])=[CH:19][CH:18]=3)[C:23]=2[C:11]([C:9]([NH2:8])=[O:10])=[CH:12][CH:36]=1

Participants

5

Reactant 4

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 8028Tetrahydrofuran2×HCID 21105725HCID 21105725, compound

Product 1

HCID 86596421HCID 86596421, compound

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 acetyl chloride 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-acetamido-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-6672ad105a484de5a8a5e4e91f8452ad
Source dataset
uspto-grants-2008_06
Patent number
US07384962B2

Reaction notes

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