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Triethylamine → HCID 58531420, compound

HRID 1889698
Notes
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Reaction equation

HRID 1889698 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:22]=[CH:23][CH:24]=2)[CH2:10][NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[OH:34][C:35]1[C:40]([Cl:41])=[CH:39][C:38]([Cl:42])=[CH:37][C:36]=1[S:43](Cl)(=[O:45])=[O:44]>C(Cl)Cl>[Cl:41][C:40]1[C:35]([OH:34])=[C:36]([S:43]([N:11]([CH2:10][C:9]2[CH:22]=[CH:23][CH:24]=[C:7]([O:6][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:26][CH:25]=3)[CH:8]=2)[CH2:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)(=[O:45])=[O:44])[CH:37]=[C:38]([Cl:42])[CH:39]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 900783,5-Dichloro-2-hydroxybenzenesulphonyl chlorideHCID 66616601HCID 66616601, compound

Product 1

HCID 58531420HCID 58531420, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of N-(3-(4-fluorophenoxy)benzyl)-4-phenylbutan-1-amine (100 mg, 28.6 mmol, 1.0 eq) in DCM (5 mL), was added triethylamine (86 mg, 85 mmol, 3 eq) followed by 2-hydroxy-3,5-dichlorobenzenesulfonyl chloride (75 mg, 28.6 mmol, 1.0 eq). The reaction mixture was stirred at ambient temperature for 4 h before being diluted with DCM (100 mL) and washed with water. The organic layer was dried over anhydrous Na2SO4 and evaporated under reduced pressure. The residue was purified by preparative HPLC to afford the title compound (45 mg, 28%); 1H NMR (400 MHz, CD3OD) δ 7.67-7.66 (d, 1H), 7.58-7.57 (d, 1H), 7.30-7.26 (t, 1H), 7.23-7.20 (t, 2H), 7.15-7.00 (m, 6H), 6.97-6.94 (m, 2H), 6.88-6.84 (m, 2H), 4.47 (s, 2H), 3.26-3.22 (t, 2H), 2.46-2.43 (t, 2H), 1.42-1.34 (m, 4H). MS (ESI): 574.0 (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 residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-9b6847f02a0a4741b956d905d5a41296
Source dataset
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08501992B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes