Acetyl chloride → HCID 59485887, compound

HRID 1972294Notes

Reaction equation

HRID 1972294 reaction equation
[Cl:1][C:2]1[CH:36]=[CH:35][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]([NH2:33])(=[O:32])=[O:31])[C:14]3=[O:34])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[C:37](Cl)(=[O:39])[CH3:38].C(N(CC)CC)C.[OH-].[Na+]>C(Cl)Cl.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]([NH:33][C:37](=[O:39])[CH3:38])(=[O:32])=[O:31])[C:14]3=[O:34])=[CH:11][CH:12]=2)=[CH:35][CH:36]=1

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 59485721HCID 59485721, compound

Product 1

HCID 59485887HCID 59485887, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-2-[3-[4-(4-chloro-phenoxy)-phenyl]-2-oxo-4-(3-trifluoromethyl-phenyl)-imidazolidin-1-yl]ethanesulfonic acid amide (20 mg, 0.037 mmol) and acetyl chloride (6 mg, 0.076 mmol) in anhydrous CH2Cl2 (1 mL) is added triethylamine (7.7 mg, 0.076 mmol). The mixture is stirred at room temperature for 14 h and is then concentrated to dryness. The residue is dissolved in EtOH and treated with NaOH (0.074 mmol, 1 M aqueous solution) for 1 h. The mixture is then treated with water (3 mL) and extracted with EtOAc (3×3 mL). The combined organic layers are concentrated and purified by flash column chromatography to provide the title compound as a white solid. 1H NMR (CDCl3, 400 MHz) δ 7.56 (m, 3H), 7.48 (m, 1H), 7.24 (d, J=8.8 Hz, 2H), 7.20 (d, J=8.8 Hz, 2H), 6.86 (d, J=9.2 Hz, 2H), 6.85 (d, J=8.8 Hz, 2H), 5.26 (dd, J=9.2, 6.8 Hz, 1H), 4.00 (t, J=9.2 Hz, 1H), 3.75-3.90 (m, 2H), 3.55-3.65 (m, 2H), 3.36 (dd, J=8.8, 6.8 Hz, 1H), 2.17 (s, 3H); HPLC-MS calculated for C26H23ClF3N3O5S (M+H+) 582.1, found 582.1.

Workup

  1. concentrationis then concentrated to dryness
  2. dissolutionThe residue is dissolved in EtOH
  3. extractionextracted with EtOAc (3×3 mL)
  4. concentrationThe combined organic layers are concentrated
  5. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-b72ab69b6d4c4d2d894d790aef587676
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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