Diethyl Pyrocarbonate → 2-[(4-chlorophenyl)sulfonyl-methyl-amino]-N-[[2-[4-(trifluoromethoxy)phenyl]-4-pyridyl]methyl]prop-2-enamide

HRID 1479813Notes

Reaction equation

HRID 1479813 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH3:17])[C:12](=[CH2:16])[C:13]([OH:15])=O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.CCOC(OC(OCC)=O)=O.[F:29][C:30]([F:47])([F:46])[O:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]2[CH:43]=[C:42]([CH2:44][NH2:45])[CH:41]=[CH:40][N:39]=2)=[CH:34][CH:33]=1>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([CH3:17])[C:12](=[CH2:16])[C:13]([NH:45][CH2:44][C:42]2[CH:41]=[CH:40][N:39]=[C:38]([C:35]3[CH:34]=[CH:33][C:32]([O:31][C:30]([F:47])([F:29])[F:46])=[CH:37][CH:36]=3)[CH:43]=2)=[O:15])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 3051Diethyl PyrocarbonateHCID 68759664[2-[4-(Trifluoromethoxy)phenyl]-4-pyridyl]methanamineHCID 1317365842-[(4-Chlorophenyl)sulfonyl-methyl-amino]prop-2-enoic acid

Product 1

HCID 903841752-[(4-chlorophenyl)sulfonyl-methyl-amino]-N-[[2-[4-(trifluoromethoxy)phenyl]-4-pyridyl]methyl]prop-2-enamideYield 18%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of acid 4C (0.50 g, 1.8 mmol) in THF (30 mL) was added with DEPC (0.35 mL, 1.3 mol eq) and the mixture stirred at room temperature several minutes. Then [2-[4-(trifluoromethoxy)phenyl]-4-pyridyl]methanamine 21B (0.53 g, 1.1 mol eq) and a catalytic amount of TEA were added, then the reaction mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure, the residue was suspended in EtOAc and washed with water and brine. The separated organic phase was dried over an. Na2SO4 and evaporated under reduced pressure. The residue was purified by flash chromatography (7:3 EtOAc:Petroleum ether) to afford a pale yellow viscous oil (0.17 g). Yield=18%, 1HNMR (DMSO, 200 MHz) δ 2.98 (s, 3H), 4.22 (d, 2H), 5.08 (s, 1H), 5.85 (s, 1H), 7.4 (m, 3H), 7.65 (dd, 4H, J=8), 7.95 (s, 1H), 8.2 (d, 2H), 8.58 (d, 1H), 8.95 (t, 1H); [M+1] 525.93 (C23H19ClF3N3O4S requires 525.07).

Workup

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. customThe solvent was removed under reduced pressure
  3. washwashed with water and brine
  4. customThe separated organic phase was dried over an
  5. customNa2SO4 and evaporated under reduced pressure
  6. customThe residue was purified by flash chromatography (7:3 EtOAc:Petroleum ether)

Sources & evidence

ORD record
ord-0dbdb680285d427a91d2b4f847eb3577
Source dataset
uspto-grants-2016_08
Patent number
US09409864B2

Reaction notes

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