6-Phenoxy-3-pyridinamine → 4-Chloro-N1-(6-phenoxy-pyridin-3-yl)-N3-(1H-pyrrolo[2,3-b]pyridin-5-yl)-isophthalamide

HRID 564018Notes

Reaction equation

HRID 564018 reaction equation
[O:1]([C:8]1[N:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][C:17]=1[C:25](=[O:36])[NH:26][C:27]1[CH:28]=[C:29]2[CH:35]=[CH:34][NH:33][C:30]2=[N:31][CH:32]=1>C(Cl)Cl>[Cl:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([NH:14][C:11]2[CH:12]=[N:13][C:8]([O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:9][CH:10]=2)=[O:21])=[CH:18][C:17]=1[C:25]([NH:26][C:27]1[CH:28]=[C:29]2[CH:35]=[CH:34][NH:33][C:30]2=[N:31][CH:32]=1)=[O:36]

Participants

4

Reactant 2

HCID 2128566-Phenoxy-3-pyridinamineHCID 866372554-chloro-3-(1H-pyrrolo[2,3-b]pyridin-5-ylcarbamoyl)-benzoyl chloride

Product 1

HCID 248120204-Chloro-N1-(6-phenoxy-pyridin-3-yl)-N3-(1H-pyrrolo[2,3-b]pyridin-5-yl)-isophthalamideYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Phenoxy-pyridin-3-ylamine (0.078 g, 0.42 mmol) was added to a solution of 4-chloro-3-(1H-pyrrolo[2,3-b]pyridin-5-ylcarbamoyl)-benzoyl chloride in DCM (5 ml) and the reaction stirred at room temperature for 2 hours. The solvent was removed under reduced pressure and the crude product triturated with acetonitrile:water (1:1, 10 ml). The solid was filtered to afford 4-Chloro-N1-(6-phenoxy-pyridin-3-yl)-N3-(1H-pyrrolo[2,3-b]pyridin-5-yl)-isophthalamide as the hydrochloride salt, 0.086 g, (37% yield) over two steps.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude product triturated with acetonitrile:water (1:1, 10 ml)
  3. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-314470b9bba3483e960fc1ec9abd4302
Source dataset
uspto-grants-2011_11
Patent number
US08067599B2

Reaction notes

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