HCID 59485644, compound → HCID 59485721, compound

HRID 1972215Notes

Reaction equation

HRID 1972215 reaction equation
[Cl:1][C:2]1[CH:54]=[CH:53][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([N:13]3[C@@H:17]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=4)[CH2:16][N:15]([CH2:28][CH2:29][S:30]([N:33](CC4C=CC(OC)=CC=4)CC4C=CC(OC)=CC=4)(=[O:32])=[O:31])[C:14]3=[O:52])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1>C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([N:13]3[C@@H:17]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:25])[F:26])[CH:19]=4)[CH2:16][N:15]([CH2:28][CH2:29][S:30]([NH2:33])(=[O:32])=[O:31])[C:14]3=[O:52])=[CH:11][CH:12]=2)=[CH:53][CH:54]=1

Participants

3

Reactant 1

HCID 59485644HCID 59485644, compound

Product 1

HCID 59485721HCID 59485721, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of (S)-2-(3-(4-(4-chlorophenoxy)phenyl)-2-oxo-4-(3-(trifluoromethyl)-phenyl)imidazolidin-1-yl)-N,N-bis(4-methoxybenzyl)ethanesulfonamide (2.2 g, 2.82 mmol) in TFA (30 mL) is stirred at room temperature for 14 h. Excess of TFA is removed under vacuum. The residue is treated with saturated NaHCO3 aqueous solution (30 mL) and extracted with EtOAc (3×50 mL). The combined organic layer is washed with brine and dried (MgSO4). After removing the drying agent, the solution is concentrated and purified by flash column chromatography (silica gel, EtOAc/hexane 0%˜90%) to provide the desired product (S)-2-(3-(4-(4-chlorophenoxy)phenyl)-2-oxo-4-(3-(trifluoromethyl)phenyl)-imidazolidin-1-yl)ethanesulfonamide as white solid (1.2 g, 83%). 1H NMR (CDCl3, 400 MHz) δ 7.55˜7.62 (m, 3H), 7.48 (t, 1H), 7.24 (d, 2H), 7.22 (d, 2H), 6.85 (m, 4H), 5.47 (s, 2H), 5.28 (dd, 1H), 3.90˜4.03 (m, 3H), 3.40 (dd, 1H), 3.28˜3.35 (m, 2H); HPLC-MS calculated for C24H21ClF3N3O4S (M+H+) 540.1, found 540.1.

Workup

  1. customExcess of TFA is removed under vacuum
  2. additionThe residue is treated with saturated NaHCO3 aqueous solution (30 mL)
  3. extractionextracted with EtOAc (3×50 mL)
  4. washThe combined organic layer is washed with brine
  5. dry with materialdried (MgSO4)
  6. customAfter removing the drying agent
  7. concentrationthe solution is concentrated
  8. custompurified by flash column chromatography (silica gel, EtOAc/hexane 0%˜90%)

Sources & evidence

ORD record
ord-ba80a0af185e45138648b357db1b812f
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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