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

HRID 1693447Notes

Reaction equation

HRID 1693447 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-9c4dd7ac36ee4840b5ce9b824a385694
Source dataset
uspto-grants-2012_04
Patent number
US08158622B2

Reaction notes

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