Triethylamine → HCID 58531504, compound

HRID 1889706Notes

Reaction equation

HRID 1889706 reaction equation
[F:1][C:2]1[CH:31]=[CH:30][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:27]=[CH:28][CH:29]=2)[CH2:10][NH:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[OH:39][C:40]1[C:45]([Cl:46])=[CH:44][C:43]([Cl:47])=[CH:42][C:41]=1[S:48](Cl)(=[O:50])=[O:49]>C(Cl)Cl>[Cl:46][C:45]1[C:40]([OH:39])=[C:41]([S:48]([N:11]([CH2:10][C:9]2[CH:27]=[CH:28][CH:29]=[C:7]([O:6][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:31][CH:30]=3)[CH:8]=2)[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:15][CH:14]=2)(=[O:50])=[O:49])[CH:42]=[C:43]([Cl:47])[CH:44]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 900783,5-Dichloro-2-hydroxybenzenesulphonyl chlorideHCID 66616606HCID 66616606, compound

Product 1

HCID 58531504HCID 58531504, compoundYield 16.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of N-(3-(4-fluorophenoxy)benzyl)-1-(4-octylphenyl)methanamine (100 mg, 0.238 mmol, 1.0 eq) in DCM (10 mL) was added triethylamine (72 mg, 0.72 mmol, 3.0 eq) followed by 2-hydroxy-3,5-dichlorobenzenesulfonyl chloride (62 mg, 0.238 mmol, 1.0 eq). After stirring at ambient temperature for 4 h, the reaction mixture was diluted with 100 mL DCM and washed with water. The organic layer was dried over anhydrous Na2SO4 and evaporated under reduced pressure. The crude residue was purified by preparative HPLC to afford the title compound (25 mg, 16%). 1H NMR (400 MHz, CD3OD) δ 7.64-7.63 (d, 1H), 7.55-7.54 (d, 1H), 7.21 (m, 1H), 7.19-7.11 (m, 2H), 7.09-7.02 (m, 4H), 6.95-6.91 (m, 2H), 6.88-6.86 (d, 1H), 6.80-6.78 (d, 1H), 6.68 (s, 1H), 4.43-4.40 (d, 4H), 3.35-3.30 (m, 6H), 2.55-2.51 (t, 2H), 1.57-1.56 (t, 3H), 1.3 (s, 10H), 0.87-0.91 (t, 3H). MS (ESI): 644.0 (M−H)−.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. customevaporated under reduced pressure
  4. customThe crude residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-2aea952238454fa1bc2e2743a19dd7ff
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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