Formic Acid → 4'-[(5-Hydroxy-4-hydroxymethyl-6-methyl-pyridin-3-ylmethyl)-amino]-biphenyl-2-sulfonic acid tert-butylamide

HRID 2373302Notizen

Reaktionsgleichung

C(O)=O.[C:4]([NH:8][S:9]([C:12]1[C:13]([C:18]2[CH:23]=[CH:22][C:21]([NH:24][CH2:25][C:26]3[CH:31]=[N:30][C:29]([CH3:32])=[C:28]4[O:33]C(C)(C)[O:35][CH2:36][C:27]=34)=[CH:20][CH:19]=2)=[CH:14][CH:15]=[CH:16][CH:17]=1)(=[O:11])=[O:10])([CH3:7])([CH3:6])[CH3:5]>O>[C:4]([NH:8][S:9]([C:12]1[C:13]([C:18]2[CH:19]=[CH:20][C:21]([NH:24][CH2:25][C:26]3[CH:31]=[N:30][C:29]([CH3:32])=[C:28]([OH:33])[C:27]=3[CH2:36][OH:35])=[CH:22][CH:23]=2)=[CH:14][CH:15]=[CH:16][CH:17]=1)(=[O:11])=[O:10])([CH3:7])([CH3:6])[CH3:5]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

To a solution of 10% formic acid in water (50 mL) was added 3-[(2,2,8-trimethyl-4H-[1,3] dioxino [4,5-c]pyridin-5-ylmethyl)-amino]-benzonitrile (1) (336 mg, 0.7 mmol) and the reaction mixture was heated at 100° C. under nitrogen atmosphere. The reaction mixture was then concentrated to dryness. The resulting pale yellow solid was dissolved in small amount of dichloromethane and diethyl ether was added to induce precipitation of a yellow solid. The 4′-[(5-hydroxy-4-hydroxymethyl-6-methyl-pyridin-3-ylmethyl)-amino]-biphenyl-2-sulfonic acid tert-butylamide (2) (215 mg, 70% yield) was collected by filtration as a pale yellow solid.

Aufarbeitung

concentrationThe reaction mixture was then concentrated to dryness
dissolutionThe resulting pale yellow solid was dissolved in small amount of dichloromethane and diethyl ether
additionwas added
customprecipitation of a yellow solid

Quellen und Nachweise

ORD-Eintrag: ord-fd25c92bbddb44259e2c1fadeb063ba9
Quelldatensatz: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07459468B2

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