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

HRID 2373302Notes

Reaction equation

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]

Participants

Conditions

Temperature: 100 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-fd25c92bbddb44259e2c1fadeb063ba9
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07459468B2

Reaction notes

Loading…