Pyridine → Water TFA acetonitrile

HRID 1162853Notes

Reaction equation

HRID 1162853 reaction equation
[OH:1][C:2]([C:4]([F:7])([F:6])[F:5])=[O:3].[F:8][C:9]1[CH:36]=[CH:35][C:12]([CH2:13][N:14]2[CH2:33][CH2:32][N:17]3[C:18](=[O:31])[N:19]([CH2:24][CH:25]4[CH2:30][O:29][CH2:28][CH2:27][NH:26]4)[C:20](=[O:23])[C:21]([OH:22])=[C:16]3[C:15]2=[O:34])=[CH:11][CH:10]=1.N1C=CC=CC=1.[C:43](OC(=O)C)(=[O:45])[CH3:44]>C(Cl)Cl>[OH2:1].[C:13](#[N:14])[CH3:12].[C:2]([OH:3])([C:4]([F:7])([F:6])[F:5])=[O:1].[C:43]([N:26]1[CH2:27][CH2:28][O:29][CH2:30][CH:25]1[CH2:24][N:19]1[C:20](=[O:23])[C:21]([OH:22])=[C:16]2[C:15](=[O:34])[N:14]([CH2:13][C:12]3[CH:11]=[CH:10][C:9]([F:8])=[CH:36][CH:35]=3)[CH2:33][CH2:32][N:17]2[C:18]1=[O:31])(=[O:45])[CH3:44]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 131728411HCID 131728411, compound

Product 2

HCID 22145617Water TFA acetonitrileHCID 54692422HCID 54692422, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2-(4-fluorobenzyl)-9-hydroxy-7-(morpholin-3-ylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,6,8(7H)-trione mono TFA salt (72 mg, 0.14 mmol, Example 17) dissolved in dry methylene chloride (1 mL) was added pyridine (13 μL, 0.17 mmol) and acetic anhydride (28 mg, 0.28 mmol). The reaction was stirred overnight at room temperature. The reaction was purified by prep HPLC using a C18 stationary phase and a water/acetonitrile/TFA gradient to obtain the title compound as a white powder after lyophilization from dioxane. High Resolution FT-ICR C21H23FN4O6+H=447.1677; calculated 447.1675.

Workup

  1. customThe reaction was purified by prep HPLC

Sources & evidence

ORD record
ord-0395448c8eb54b888deebfc23bd9e76f
Source dataset
uspto-grants-2010_10
Patent number
US07820680B2

Reaction notes

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