9-oxo-9H-pyrrolo[1,2-a]indole-5-carboxylic acid (4-aminopyridin-3-yl)amide → HCID 67072884, compound

HRID 1925572

Reaction equation

HRID 1925572 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:19]=1[N:18]1[CH:20]=[CH:21][CH:22]=[C:17]1[C:16]2=[O:23])=O>C(O)(=O)C>[N:1]1[C:2]2[CH:7]=[CH:6][N:5]=[CH:4][C:3]=2[NH:8][C:9]=1[C:11]1[C:19]2[N:18]3[CH:20]=[CH:21][CH:22]=[C:17]3[C:16](=[O:23])[C:15]=2[CH:14]=[CH:13][CH:12]=1

Participants

3

Reactant 1

HCID 672993589-oxo-9H-pyrrolo[1,2-a]indole-5-carboxylic acid (4-aminopyridin-3-yl)amide

Product 1

HCID 67072884HCID 67072884, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
200 °C

Procedure

In a 20 ml microwave reactor, a mixture of 256 mg of 9-oxo-9H-pyrrolo[1,2-a]indole-5-carboxylic acid (4-aminopyridin-3-yl)amide obtained according to the preceding stage, in 20 ml of glacial acetic acid, is heated at 200° C. for 30 minutes. The reaction medium is filtered through clarcel, washing being carried out with glacial acetic acid. The filtrate is evaporated to dryness under vacuum and the residue is taken up twice with toluene and each time re-evaporated to dryness under vacuum. The solid is triturated from isopropyl ether, filtered, and dried under vacuum at 40° C. overnight. 111 mg of 5-(3H-imidazo[4,5-c]pyridin-2-yl)pyrrolo[1,2-a]indol-9-one are obtained in the form of a solid, the characteristics of which are the following:

Workup

  1. customobtained
  2. filtrationThe reaction medium is filtered through clarcel
  3. washwashing
  4. customThe filtrate is evaporated to dryness under vacuum
  5. customeach time re-evaporated to dryness under vacuum
  6. customThe solid is triturated from isopropyl ether
  7. filtrationfiltered
  8. customdried under vacuum at 40° C. overnight

Sources & evidence

ORD record
ord-cd8eeddff9144481bd321ffc907f4d29
Source dataset
uspto-grants-2012_05
Patent number
US08178687B2

Linked notes

Loading…