Sodium Hydroxide → HCID 50995179, compound

HRID 1399621Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of sodium hydroxide 5N (1 mL) was added to a mixture of methyl 2-(2-(4-benzamidopiperidin-1-yl)-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate (0.049 g; 0.0979 mmol) in methanol (1.5 mL). The mixture was heated in a sealed tube at 100° C. for 18 h and then concentrated under reduced pressure. The residue was dissolved in water and the pH of the solution was adjusted between 3 and 4 by addition of a solution of hydrochloric acid 6N. The precipitate was collected by filtration and was purified by preparative HPLC (HPLC method 4) furnished 0.024 g (51%) of the title compound as a white solid.

Workup

concentrationconcentrated under reduced pressure
dissolutionThe residue was dissolved in water
additionthe pH of the solution was adjusted between 3 and 4 by addition of a solution of hydrochloric acid 6N
filtrationThe precipitate was collected by filtration
customwas purified by preparative HPLC (HPLC method 4)

Sources & evidence

ORD record: ord-7f0a46cfedac4744ac63afd5f9651cb4
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906906B2

Reaction notes

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