Hydrochloric Acid → 5-(1-Isopropyl-piperidin-4-yloxy)-1H-pyrrolo[2,3-b]pyridine-2-carboxylic Acid Hydrochloride

HRID 1437708Notes

Reaction equation

HRID 1437708 reaction equation
CC[O:3][C:4]([C:6]1[N:24](C(OC(C)(C)C)=O)[C:9]2=[N:10][CH:11]=[C:12]([O:14][CH:15]3[CH2:20][CH2:19][N:18]([CH:21]([CH3:23])[CH3:22])[CH2:17][CH2:16]3)[CH:13]=[C:8]2[CH:7]=1)=[O:5].[ClH:32]>O1CCOCC1>[ClH:32].[CH:21]([N:18]1[CH2:19][CH2:20][CH:15]([O:14][C:12]2[CH:13]=[C:8]3[CH:7]=[C:6]([C:4]([OH:5])=[O:3])[NH:24][C:9]3=[N:10][CH:11]=2)[CH2:16][CH2:17]1)([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 684233285-(1-Isopropyl-piperidin-4-yloxy)-pyrrolo[2,3-b]pyridine-1,2-dicarboxylic Acid 1-tert-butyl Ester 2-ethyl Ester

Product 1

HCID 684239235-(1-Isopropyl-piperidin-4-yloxy)-1H-pyrrolo[2,3-b]pyridine-2-carboxylic Acid HydrochlorideYield 98%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The solution of 0.24 g (0.56 mmol) 5-(1-isopropyl-piperidin-4-yloxy)-pyrrolo[2,3-b]pyridine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester in 1.2 ml dioxan is treated with 0.56 ml concentrated hydrochloric acid and stirred for 16 hours under reflux. The volatile components were removed at a rotary evaporator and the residue was dried under high vacuum to give 0.19 g (98%) of the product as a brown foam which was pure enough for the next step without further purification.

Workup

  1. temperatureunder reflux
  2. customThe volatile components were removed at a rotary evaporator
  3. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-aa59c26166c64c53b5fb6f1fabd61393
Source dataset
uspto-grants-2009_11
Patent number
US07622466B2

Reaction notes

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