p-Toluenesulfonic acid monohydrate → HCID 178463361, compound

HRID 81205Notes

Reaction equation

HRID 81205 reaction equation
CC1C=CC(S(O)(=O)=O)=CC=1.O.[NH2:13][C:14]1[C:15]([Cl:29])=[N:16][C:17]([Cl:28])=[CH:18][C:19]=1[NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24].[CH3:30][C@H:31]1[CH2:36][CH2:35][C@H:34]([C:37](=O)[CH3:38])[CH2:33][CH2:32]1>C1(C)C=CC=CC=1>[Cl:29][C:15]1[C:14]([N:13]=[C:37]([C@H:34]2[CH2:35][CH2:36][C@H:31]([CH3:30])[CH2:32][CH2:33]2)[CH3:38])=[C:19]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[CH:18]=[C:17]([Cl:28])[N:16]=1

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 86724467Tert-butyl (3-amino-2,6-dichloropyridin-4-yl)carbamate2×HCID 178468157HCID 178468157, compound

Product 1

HCID 178463361HCID 178463361, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

p-TsOH.H2O (3.4 g, 0.018 mol) was added to a mixture of tert-butyl (3-amino-2,6-dichloropyridin-4-yl)carbamate (85 g, 0.306 mol) and 1-(trans-4-methylcyclohexyl)ethanone (64 g, 0.46 mol) in toluene (1.3 L). The mixture was heated to reflux with a Dean-Stark trap for 14 h. TLC (petroleum/ethyl acetate=5:1) showed about ⅔ of tert-butyl (3-amino-2,6-dichloropyridin-4-yl)carbamate was consumed. The solvent was removed under reduced pressure. The residue was purified by column chromatography (petroleum ether) to give crude tert-butyl (2,6-dichloro-3-((1-(trans-4-methylcyclohexyl)ethylidene)amino)pyridin-4-yl)carbamate.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux with a Dean-Stark trap for 14 h
  3. customwas consumed
  4. customThe solvent was removed under reduced pressure
  5. customThe residue was purified by column chromatography (petroleum ether)

Sources & evidence

ORD record
ord-0f84ed1e7117488e9f18b4d36029a976
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

Loading…