Hydrochloric Acid → HCID 21906387, compound

HRID 1883008Notes

Reaction equation

HRID 1883008 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:31])[C:10]2[CH:15]=[CH:14][C:13]([C:16]([O:18]C)=[O:17])=[CH:12][C:11]=2[NH:20][CH2:21][CH:22]2[CH2:27][CH2:26][N:25]([CH:28]([CH3:30])[CH3:29])[CH2:24][CH2:23]2)=[N:6][CH:7]=1.O1CCCC1.[OH-].[Li+].Cl>O>[ClH:1].[C:16]([C:13]1[CH:14]=[CH:15][C:10]([C:9]([NH:8][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=2)=[O:31])=[C:11]([NH:20][CH2:21][CH:22]2[CH2:27][CH2:26][N:25]([CH:28]([CH3:30])[CH3:29])[CH2:24][CH2:23]2)[CH:12]=1)([OH:18])=[O:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 21906267HCID 21906267, compound

Product 1

HCID 21906387HCID 21906387, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of N-(5-chloropyridin-2-yl)-2-(1-isopropylpiperidin-4-ylmethylamino)-4-methoxycarbonylbenzamide (100 mg, 0.225 mmol) in 4:1 tetrahydrofuran:water (2.5 mL) was treated with lithium hydroxide (20 mg, 0.90 mmol). After 17 h, the pH of the mixture was adjusted to 2-3 by addition of 1 N HCl. The mixture was then concentrated and the residue purified by RPHPLC affording 32 mg (30%) of the title compound as a hydrochloride salt.

Workup

  1. concentrationThe mixture was then concentrated
  2. customthe residue purified by RPHPLC

Sources & evidence

ORD record
ord-e2e6540610db4c72aacc708199464677
Source dataset
uspto-grants-2004_07
Patent number
US06759414B2

Reaction notes

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