Lithium hydroxide, monohydrate → 2-(2-(3-(Methyl(2-morpholinoethyl)carbamoyl)benzamido)-5-(piperidin-1-yl)phenyl)isonicotinic acid

HRID 1408081Notes

Reaction equation

HRID 1408081 reaction equation
[CH3:1][N:2]([CH2:36][CH2:37][N:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1)[C:3]([C:5]1[CH:6]=[C:7]([CH:33]=[CH:34][CH:35]=1)[C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:13][C:12]=1[C:23]1[CH:24]=[C:25]([CH:30]=[CH:31][N:32]=1)[C:26]([O:28]C)=[O:27])=[O:9])=[O:4].O.[OH-].[Li+]>O1CCOCC1.O>[CH3:1][N:2]([CH2:36][CH2:37][N:38]1[CH2:39][CH2:40][O:41][CH2:42][CH2:43]1)[C:3]([C:5]1[CH:6]=[C:7]([CH:33]=[CH:34][CH:35]=1)[C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]2)=[CH:13][C:12]=1[C:23]1[CH:24]=[C:25]([CH:30]=[CH:31][N:32]=1)[C:26]([OH:28])=[O:27])=[O:9])=[O:4]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 66588050Methyl 2-(2-(3-(methyl(2-morpholinoethyl)carbamoyl)benzamido)-5-(piperidin-1-yl)phenyl)isonicotinate

Product 1

HCID 665880492-(2-(3-(Methyl(2-morpholinoethyl)carbamoyl)benzamido)-5-(piperidin-1-yl)phenyl)isonicotinic acidYield 124.2%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A solution of 231 mg of methyl 2-(2-(3-(methyl(2-morpholinoethyl)carbamoyl)benzamido)-5-(piperidin-1-yl)phenyl)isonicotinate in 9 mL of 2:1 dioxane/water was treated with 33 mg of lithium hydroxide hydrate. After stirring for 1 h the solvent was evaporated and the residue was partitioned between dichloromethane and 3 N hydrochloric acid. The aqueous phase was evaporated to give the product as 280 mg of a yellow solid.

Workup

  1. customwas evaporated
  2. customthe residue was partitioned between dichloromethane and 3 N hydrochloric acid
  3. customThe aqueous phase was evaporated

Sources & evidence

ORD record
ord-0e8c29440e444e98955de68012c53956
Source dataset
uspto-grants-2014_12
Patent number
US08916569B2

Reaction notes

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