Triethylamine → HCID 44595537, compound

HRID 1889711Notes

Reaction equation

HRID 1889711 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][NH:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[C:9]=2[O:24][CH3:25])=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:33][C:34]1[C:35]([OH:45])=[C:36]([S:41](Cl)(=[O:43])=[O:42])[CH:37]=[C:38]([Cl:40])[CH:39]=1>C(Cl)Cl>[Cl:33][C:34]1[C:35]([OH:45])=[C:36]([S:41]([N:15]([CH2:14][C:10]2[C:9]([O:24][CH3:25])=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH:13]=[CH:12][CH:11]=2)[CH2:16][C:17]2[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=2)(=[O:43])=[O:42])[CH:37]=[C:38]([Cl:40])[CH:39]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 900783,5-Dichloro-2-hydroxybenzenesulphonyl chlorideHCID 58531406HCID 58531406, compound

Product 1

HCID 44595537HCID 44595537, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1-(4′-chloro-2-methoxybiphenyl-3-yl)-N-(4-fluorobenzyl)methanamine (590 mg, 1.684 mmol, 1.0 eq) in dry DCM under nitrogen at 0° C. and treated slowly with triethylamine (492 mg, 4.8 mmol, 3 eq). The reaction mixture was stirred for 10 minutes and treated with a solution of 3,5-dichloro-2-hydroxybenzene-1-sulfonyl chloride (527 mg, 2.018 mmol, 1.2 eq) dissolved in DCM. The resulting mixture was stirred for 12 h at ambient temperature and concentrated under reduced pressure. The residue was further diluted with water and extracted with ethyl acetate. The organic layer was dried under anhydrous Na2SO4 and concentrated. The residue was purified by flash column chromatography on silica gel (60-120) eluting with 15-20% ethyl acetate/hexane to afford the title compound (0.400 g, 50%). 1H NMR (400 MHz, DMSO-d6) δ 3.32 (s, 3H), 4.52-4.53 (d, 4H), 7.04-7.08 (m, 3H), 7.17-7.24 (m, 4H), 7.43-7.52 (m, 5H), 7.77 (s, 1H). MS (ESI): 577.8 (M−H)−.

Workup

  1. stirringThe resulting mixture was stirred for 12 h at ambient temperature
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was further diluted with water
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was dried under anhydrous Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography on silica gel (60-120)
  8. washeluting with 15-20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-26b5f9a47d774808aea186a5b679c809
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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