Triethylamine → HCID 58531490, compound

HRID 1889627Notes

Reaction equation

HRID 1889627 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9](Cl)(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[Cl:13][C:14]1[C:15]([OH:54])=[C:16]([S:21]([N:24]([CH2:46][C:47]2[CH:52]=[CH:51][C:50]([F:53])=[CH:49][CH:48]=2)[CH2:25][C:26]2[CH:31]=[C:30]([CH2:32][NH:33][CH2:34][CH:35]([CH3:37])[CH3:36])[CH:29]=[C:28]([O:38][C:39]3[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=3)[CH:27]=2)(=[O:23])=[O:22])[CH:17]=[C:18]([Cl:20])[CH:19]=1.CCN(CC)CC>C(Cl)Cl.C([O-])(O)=O.[Na+]>[Cl:13][C:14]1[C:15]([OH:54])=[C:16]([S:21]([N:24]([CH2:25][C:26]2[CH:27]=[C:28]([O:38][C:39]3[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=3)[CH:29]=[C:30]([CH2:32][N:33]([CH2:34][CH:35]([CH3:37])[CH3:36])[S:9]([C:4]3[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=3)(=[O:11])=[O:10])[CH:31]=2)[CH2:46][C:47]2[CH:48]=[CH:49][C:50]([F:53])=[CH:51][CH:52]=2)(=[O:23])=[O:22])[CH:17]=[C:18]([Cl:20])[CH:19]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 5223883,5-Dichlorobenzenesulfonyl chlorideHCID 58531576HCID 58531576, compound

Product 1

HCID 58531490HCID 58531490, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 3,5-dichlorobenzenesulfonyl chloride (27.0 mg, 0.11 mmol) in CH2Cl2 (3 mL) was added 3,5-dichloro-N-(4-fluorobenzyl)-N-(3-(4-fluorophenoxy)-5-((isobutylamino)methyl)benzyl)-2-hydroxybenzenesulfonamide (70 mg, 0.11 mmol, 80% purity), followed by the addition of Et3N (0.09 mL, 0.66 mmol). The reaction mixture was stirred at rt for 1 h. The reaction mixture was diluted with CH2Cl2 and saturated NaHCO3 solution. The organic layer was concentrated. To the residue was added 1 N NaOH/MeOH/THF. The resulting mixture was left for 2 h. The mixture was concentrated and the residue was diluted with CH2Cl2 and water. The organic layer was concentrated. The residue was dissolved in MODEL and purified by preparative HPLC. Fractions containing the desired product were combined, concentrated, and lyophilized to give a white solid (35 mg, 38%). 1H NMR (CD3OD): δ 7.67-7.63 (m, 4H), 7.57 (d, J=2.8 Hz, 1H), 7.14-7.04 (m, 4H), 6.91 (t, J=8.8 Hz, 2H), 6.87-6.83 (m, 2H), 6.70 (s, 1H), 6.63 (s, 1H), 6.56 (s, 1H), 4.40 (s, 2H), 4.32 (s, 2H), 4.21 (s, 2H), 2.91 (d, J=7.6 Hz, 2H), 1.65 (m, 1H), 0.74 (d, J=6.4 Hz, 6H); MS (ESI): (M−H)−=843.0.

Workup

  1. concentrationThe organic layer was concentrated
  2. additionTo the residue was added 1 N NaOH/MeOH/THF
  3. waitThe resulting mixture was left for 2 h
  4. concentrationThe mixture was concentrated
  5. additionthe residue was diluted with CH2Cl2 and water
  6. concentrationThe organic layer was concentrated
  7. dissolutionThe residue was dissolved in MODEL
  8. custompurified by preparative HPLC
  9. additionFractions containing the desired product
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-98a9e43db6b74a67803c4e9c263026b0
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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