Hydrochloric Acid → 5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid [2-(4-methoxyphenyl)-2-oxoethyl]amide

HRID 751701Notes

Reaction equation

HRID 751701 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([CH2:15][NH:16][C:17]([C:19]3[NH:28][C:22]4=[CH:23][N:24]=[C:25]([Cl:27])[CH:26]=[C:21]4[CH:20]=3)=[O:18])OCC[O:11]2)=[CH:6][CH:5]=1>CC(C)=O>[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10](=[O:11])[CH2:15][NH:16][C:17]([C:19]2[NH:28][C:22]3=[CH:23][N:24]=[C:25]([Cl:27])[CH:26]=[C:21]3[CH:20]=2)=[O:18])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59753533CID 59753533

Product 1

HCID 111987015-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid [2-(4-methoxyphenyl)-2-oxoethyl]amide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Aqueous hydrochloric acid (2.1 mL, 2M) was added to a solution of 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid [2-(4-methoxyphenyl)[1,3]dioxolan-2-ylmethyl]amide (Preparation 49, 160 mg, 0.41 mmol) in acetone (20 mL). The mixture was heated under reflux for 90 min then allowed to cool to rt. The suspension was filtered then washed with acetone and air dried, to give the title compound as a pale yellow solid. δH (d6 DMSO): 3.86 (3H, s), 4.79 (2H, d), 7.08 (2H, d), 7.23 (1H, s), 7.77 (1H, s), 8.03 (2H, d), 8.58 (1H, s), 9.14 (1H, t), 12.31 (1H, br s). m/z (ES+)=344 [M+H]+; RT=3.34 min.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 90 min
  3. filtrationThe suspension was filtered
  4. washthen washed with acetone and air
  5. customdried

Sources & evidence

ORD record
ord-ad8502aae9414927ac93c036b50d08ac
Source dataset
uspto-grants-2008_07
Patent number
US07405210B2

Reaction notes

Loading…