Dimethyl Sulfoxide → HCID 178527294, compound

HRID 1523751Notes

Reaction equation

HRID 1523751 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[N:18]=[CH:19][N:20](S(C3C=CC=CC=3Br)(=O)=O)[CH:21]=2)[CH2:13][CH2:12]1)(=[O:10])=[O:9].CS(C)=O.[Li+].[OH-]>CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[CH2:12][CH2:13][CH:14]([C:17]2[N:18]=[CH:19][NH:20][CH:21]=2)[CH2:15][CH2:16]1)(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 679Dimethyl Sulfoxide2×HCID 3939Lithium HydroxideHCID 90312974HCID 90312974, compound

Product 1

HCID 178527294HCID 178527294, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 20 mL vial containing 1-[(2-bromophenyl)sulfonyl]-4-{1-[(2-bromophenyl)-sulfonyl]-1H-imidazol-4-yl}piperidine (884 mg, 1.50 mmol) were added a stirbar and DMSO (10 mL). Once the DMSO solution was homogeneous, LiOH (3 mL, 1.0 M) was added slowly. After 30 min the reaction mixture was diluted with EtOAc, washed with water (×4) and brine (×1), dried over MgSO4, filtered and concentrated to dryness to give the title compound (522 mg, 94%). MS (ESI): mass calcd. for C14H16BrN3O2S 369.01 m/z found 370.0 [M+H]+; 1H NMR (600 MHz, CDCl3) δ 8.08 (dd, J=7.9, 1.7, 1H), 7.72 (dd, J=7.8, 1.3, 1H), 7.62 (s, 1H), 7.45-7.41 (m, 1H), 7.40-7.35 (m, 1H), 6.76 (s, 1H), 3.88 (d, J=12.8, 1H), 2.90 (m, 2H), 2.76-2.69 (m, 1H), 2.09-2.01 (m, 2H), 1.77-1.67 (m, 2H).

Workup

  1. washwashed with water (×4) and brine (×1)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-57ed6550fbac405ba0733aa3f5be3cc9
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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