Pyridine → (6-(1-((3,4-Difluorobenzyl)-methyl-amino)-ethylideneamino)-2-hydroxyindan-1-yl)-carbamic acid tert-butyl ester

HRID 2053721Notes

Reaction equation

HRID 2053721 reaction equation
FC(F)(F)S(OC)(=O)=O.[F:10][C:11]1[CH:12]=[C:13]([CH:20]=[CH:21][C:22]=1[F:23])[CH2:14][N:15]([CH3:19])[C:16](=S)[CH3:17].[C:24]([O:28][C:29](=[O:42])[NH:30][CH:31]1[C:39]2[C:34](=[CH:35][CH:36]=[C:37]([NH2:40])[CH:38]=2)[CH2:33][CH:32]1[OH:41])([CH3:27])([CH3:26])[CH3:25].N1C=CC=CC=1>C(Cl)Cl>[C:24]([O:28][C:29](=[O:42])[NH:30][CH:31]1[C:39]2[C:34](=[CH:35][CH:36]=[C:37]([N:40]=[C:16]([N:15]([CH2:14][C:13]3[CH:20]=[CH:21][C:22]([F:23])=[C:11]([F:10])[CH:12]=3)[CH3:19])[CH3:17])[CH:38]=2)[CH2:33][CH:32]1[OH:41])([CH3:27])([CH3:25])[CH3:26]

Participants

6

Reactant 4

HCID 1049PyridineHCID 9526Methyl triflateHCID 22001648(6-Amino-2-hydroxyindan-1-yl)carbamic acid tert-butyl esterHCID 86217852N-(3,4-difluorobenzyl)-N-methylthioacetamide

Product 1

HCID 69221258(6-(1-((3,4-Difluorobenzyl)-methyl-amino)-ethylideneamino)-2-hydroxyindan-1-yl)-carbamic acid tert-butyl esterYield 298.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add methyl trifluoromethanesulfonate (0.750 g, 3.49 mmol) to a solution of N-(3,4-difluorobenzyl)-N-methylthioacetamide (0.145 g, 0.736 mmol) in 10 mL of CH2Cl2 at room temperature. Stir the mixture for 30 minutes and remove the solvent under reduced pressure. Then add (6-amino-2-hydroxyindan-1-yl)-carbamic acid t-butyl ester (0.78 g, 2.97 mmol) followed by 5 mL of pyridine. The resulting mixture is stirred for 12 h. After pyridine is evaporated, the residue is purified by column chromatograph (silica gel, 3% MeOH in CH2Cl2) to give 0.98 g of (6-(1-((3,4-difluorobenzyl)-methyl-amino)-ethylideneamino)-2-hydroxyindan-1-yl)-carbamic acid tert-butyl ester as a white solid: MS 446 (MH+).

Workup

  1. customremove the solvent under reduced pressure
  2. stirringThe resulting mixture is stirred for 12 h
  3. customAfter pyridine is evaporated
  4. customthe residue is purified by column chromatograph (silica gel, 3% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-31a765798f6843d3aa987bc814756e15
Source dataset
uspto-grants-2008_02
Patent number
US07326731B2

Reaction notes

Loading…