3-Pyridinemethanol → N-{4-[2-Amino-6-(3-pyridylmethyloxy)-3,5-dicyano-4-pyridinyl]phenyl}-acetamide

HRID 2264526Notes

Reaction equation

HRID 2264526 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:19])[CH3:18])=[CH:12][CH:11]=2)[C:5]([C:20]#[N:21])=[C:4](SC2C=CC=CC=2)[N:3]=1.CC(C)([O-])C.[K+].[N:35]1[CH:40]=[CH:39][CH:38]=[C:37]([CH2:41][OH:42])[CH:36]=1>>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:11]=[CH:12][C:13]([NH:16][C:17](=[O:19])[CH3:18])=[CH:14][CH:15]=2)[C:5]([C:20]#[N:21])=[C:4]([O:42][CH2:41][C:37]2[CH:36]=[N:35][CH:40]=[CH:39][CH:38]=2)[N:3]=1

Participants

4

Reactant 3

HCID 75103-PyridinemethanolHCID 12016387N-{4-[2-Amino-3,5-dicyano-6-(phenylsulphanyl)-4-pyridinyl]phenyl}acetamideHCID 23665647Potassium tert-butoxide

Product 1

HCID 10110557N-{4-[2-Amino-6-(3-pyridylmethyloxy)-3,5-dicyano-4-pyridinyl]phenyl}-acetamide

Conditions

Temperature
60 °C

Procedure

115 mg (0.3 mmol) of N-{4-[2-amino-3,5-dicyano-6-(phenylsulfanyl)-4-pyridinyl]phenyl}acetamide [prepared analogously to Kambe et al., Synthesis, 531-533 (1981)] are, together with 50 mg (0.45 mmol) of potassium tert-butoxide, dissolved/suspended in 1.12 g (=1 ml, 10.3 mmol) of 3-pyridylmethyl alcohol, and the mixture is stirred at 60° C. for 2 h. The precipitate is filtered off with suction and suspended in a mixture of water and ethanol, and 0.3 ml of 5N acetic acid is added. After filtration, the product is purified by preparative HPLC on reversed-phase silica gel (gradient: water/acetonitrile 95:510:90 in 38 minutes).

Workup

  1. filtrationThe precipitate is filtered off with suction
  2. additionsuspended in a mixture of water and ethanol, and 0.3 ml of 5N acetic acid
  3. additionis added
  4. filtrationAfter filtration
  5. customthe product is purified by preparative HPLC on reversed-phase silica gel (gradient: water/acetonitrile 95:510:90 in 38 minutes)

Sources & evidence

ORD record
ord-bbeeb56fd1c24351a97650ab4242ec90
Source dataset
uspto-grants-2010_12
Patent number
US07855219B2

Reaction notes

Loading…