HCID 14390490, compound → 2-(4-Chloro-2-pyridinyl)3H-imidazo[4,5-b]pyridine-3-acetic acid ethyl ester

HRID 2351632Notes

Reaction equation

HRID 2351632 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][NH:6][C:7]1[C:12]([NH:13][C:14]([C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][N:17]=2)=O)=[CH:11][CH:10]=[CH:9][N:8]=1)[CH3:2]>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][N:6]1[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:12]2[N:13]=[C:14]1[C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][N:17]=1)[CH3:2]

Participants

3

Reactant 1

HCID 14390490HCID 14390490, compound

Product 1

HCID 156171842-(4-Chloro-2-pyridinyl)3H-imidazo[4,5-b]pyridine-3-acetic acid ethyl esterYield 21%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The cyclization was effected by heating 12.3 g (0.037 mole) of N-[3-[[(4-chloro-2-pyridinyl)carbonyl]amino]-2-pyridinyl]glycine ethyl ester at 200°-210° C. (oil bath) for 15 minutes. The dark residue was dissolved in methylene chloride and filtered. The filtrate was treated with Florisil®, filtered, and evaporated to an oil, which crystallized upon standing. The solid was crystallized from methanol-water, washed with 50% aqueous methanol, and dried under high vacuum at 50° C. overnight to give 2.44 g (21%) of title compound, mp 99°-101° C.

Workup

  1. filtrationfiltered
  2. additionThe filtrate was treated with Florisil®
  3. filtrationfiltered
  4. customevaporated to an oil, which
  5. customcrystallized
  6. customThe solid was crystallized from methanol-water
  7. washwashed with 50% aqueous methanol
  8. customdried under high vacuum at 50° C. overnight

Sources & evidence

ORD record
ord-3bbea7aec97b4ae990195f1e2406a859
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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