Diisopropylethylamine → HCID 58531471, compound

HRID 1889720Notes

Reaction equation

HRID 1889720 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][S:19][CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:13]=2)=[CH:4][CH:3]=1.[Cl:28][C:29]1[C:30]([OH:40])=[C:31]([S:36](Cl)(=[O:38])=[O:37])[CH:32]=[C:33]([Cl:35])[CH:34]=1.C(N(CC)C(C)C)(C)C>C1COCC1>[Cl:28][C:29]1[C:30]([OH:40])=[C:31]([S:36]([N:10]([CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][S:19][CH2:20][CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:13]=2)(=[O:38])=[O:37])[CH:32]=[C:33]([Cl:35])[CH:34]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 900783,5-Dichloro-2-hydroxybenzenesulphonyl chlorideHCID 66616515HCID 66616515, compound

Product 1

HCID 58531471HCID 58531471, compoundYield 44.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-fluorophenyl)-N-(3-(phenethylthiomethyl)benzyl)ethanamine (70 mg, 0.184 mmol) in THF (3 mL) were added 3,5-dichloro-2-hydroxybenzenesulfonyl chloride (63 mg, 0.24 mmol) and N,N-diisopropylethylamine (0.1 mL, 0.55 mmol). The resulting reaction mixture was stirred at it for 1.5 h. The reaction mixture was concentrated and the residue was dissolved in MeOH. The mixture was purified by preparative HPLC. Fractions containing the desired product were combined, concentrated in vacuo and lyophilized to give the title compound (50 mg, 44%) as a white solid. 1H NMR (CDCl3) δ 9.15 (s, 1H), 7.55 (d, J=4.0 Hz, 1H), 7.45 (d, J=4.0 Hz, 1H), 7.34-7.15 (m, 9H), 6.98-6.89 (m, 4H), 4.40 (s, 2H), 3.70 (s, 2H), 3.35 (t, J=8.0 Hz, 2H), 2.86 (t, J=4.0 Hz, 2H), 2.69-2.63 (m, 4H). MS (ESI): 602.0 (M−H)−.

Workup

  1. customThe resulting reaction mixture
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe residue was dissolved in MeOH
  4. customThe mixture was purified by preparative HPLC
  5. additionFractions containing the desired product
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aef54fc1208647259ea4bb9752417c50
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

Loading…