3-Methylbenzoic acid → 1H-Pyrrolo[2,3-b]pyridine-5-carboxamide

HRID 1360195Notes

Reaction equation

HRID 1360195 reaction equation
CC1C=C(C=CC=1)C(O)=[O:6].O[N:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=N1.[CH3:21][N:22]1CCC[C:23]1=O>>[NH:14]1[C:21]2=[N:22][CH:23]=[C:17]([C:16]([NH2:12])=[O:6])[CH:18]=[C:19]2[CH:20]=[CH:15]1

Participants

4

Reactant 3

HCID 74183-Methylbenzoic acidHCID 13387N-methyl-2-pyrrolidoneHCID 757711-Hydroxybenzotriazole

Product 1

HCID 457903211H-Pyrrolo[2,3-b]pyridine-5-carboxamide

Conditions

Temperature
50 °C

Procedure

To a solution of 3-methylbenzoic acid (22.4 mg) in 1-methyl-2-pyrrolidone (0.6 ml) were added 4-[(3-exo-8-azabicyclo[3.2.1]oct-3-yl)amino]-1H-pyrrolo[2,3-b]pyridine-5-carboxamide (42.8 mg) and 1-hydroxybenzotriazole (22.3 mg) Furthermore, 1M 1-ethyl-3-(3-dimethylaminopropyl)-1-carbodiimide/1-methyl-2-pyrrolidone solution (0.225 ml) was added, and the mixture was stirred for 4 hours at 50° C. After being cooled, the reaction solution was directly purified by preparative HPLC system (10 mM-NH4HCO3+NH3 (pH=9.2):CH3CN=98:2 to 30:70). The active fraction was concentrated and dried to hardness to obtain 4-{[(3-exo)-8-(3-methylbenzoyl)-8-azabicyclo[3.2.1]oct-3-yl)amino]}-1H-pyrrolo[2,3-b]pyridine-5-carboxamide (34.8 mg) as a solid.

Workup

  1. temperatureAfter being cooled
  2. customthe reaction solution was directly purified by preparative HPLC system (10 mM-NH4HCO3+NH3 (pH=9.2):CH3CN=98:2 to 30:70)
  3. concentrationThe active fraction was concentrated
  4. customdried to hardness

Sources & evidence

ORD record
ord-20ccbe97513f492f8b5fa5d9d91f3674
Source dataset
uspto-grants-2011_02
Patent number
US07879844B2

Reaction notes

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