Formic Acid → N-(4-methoxyphenyl)-4-methyl-2-((pyridin-3-yloxy)methyl)piperazine-1-carboxamide dihydrochloride

N-(4-methoxyphenyl)-2-((pyridin-3-yloxy)methyl)piperazine-1-carboxamide dihydrochloride (prepared as described in Example 10) (123 mg, 0.295 mmol), was dissolved in formaldehyde (37% aqueous solution, 1 mL) and formic acid (1 mL) and heated to 60° C. After 16 h, the reaction mixture was brought to pH 12 with 1 N NaOH in water and was extracted with CH2Cl2 (3×10 mL). The combined organics were dried over Na2SO4, filtered, and concentrated under reduced pressure. The material was purified by HPLC (5 to 30% MeCN/0.1% TFA in H2O/0.1% TFA gradient). The desired fractions were concentrated under reduced pressure, dissolved in MeOH (1 mL) and treated with 4M HCl in 1,4-dioxane. The mixture was concentrated under reduced pressure, yielding 16.2 mg (13%) of the desired product as an off-white solid. LC-MS: RT=3.59 min, [M+H]+=357.1.

1. extractionwas extracted with CH2Cl2 (3×10 mL)
2. dry with materialThe combined organics were dried over Na2SO4
3. filtrationfiltered
4. concentrationconcentrated under reduced pressure
5. customThe material was purified by HPLC (5 to 30% MeCN/0.1% TFA in H2O/0.1% TFA gradient)
6. concentrationThe desired fractions were concentrated under reduced pressure
7. dissolutiondissolved in MeOH (1 mL)
8. additiontreated with 4M HCl in 1,4-dioxane
9. concentrationThe mixture was concentrated under reduced pressure

ORDレコード

ord-1c13f51b04b349e9897c0de08d39be8e

出典データセット

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07943622B2