Dichloromethane → 3,5-Dichloro-N-(4-fluorobenzyl)-N-(4-((4-fluorobenzylamino)methyl)benzyl)-2-hydroxybenzenesulfonamide

HRID 1889667Notes

Reaction equation

HRID 1889667 reaction equation
[NH2:1][CH2:2][C:3]1[CH:30]=[CH:29][C:6]([CH2:7][N:8]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[S:9]([C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[C:14]([Cl:19])[C:13]=2[OH:20])(=[O:11])=[O:10])=[CH:5][CH:4]=1.C(Cl)Cl.[F:34][C:35]1[CH:42]=[CH:41][C:38]([CH:39]=O)=[CH:37][CH:36]=1.[BH4-].[Na+]>C(O)(C)C>[Cl:19][C:14]1[C:13]([OH:20])=[C:12]([S:9]([N:8]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[CH2:7][C:6]2[CH:5]=[CH:4][C:3]([CH2:2][NH:1][CH2:39][C:38]3[CH:41]=[CH:42][C:35]([F:34])=[CH:36][CH:37]=3)=[CH:30][CH:29]=2)(=[O:11])=[O:10])[CH:17]=[C:16]([Cl:18])[CH:15]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 680234-FluorobenzaldehydeHCID 4311764Sodium borohydrideHCID 58531430N-(4-(Aminomethyl)benzyl)-3,5-dichloro-N-(4-fluorobenzyl)-2-hydroxybenzenesulfonamide

Product 1

HCID 585314183,5-Dichloro-N-(4-fluorobenzyl)-N-(4-((4-fluorobenzylamino)methyl)benzyl)-2-hydroxybenzenesulfonamideYield 57%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of N-(4-(aminomethyl)benzyl)-3,5-dichloro-N-(4-fluorobenzyl)-2-hydroxybenzenesulfonamide (235 mg, 0.50 mmol) in a mixed solvent (10 mL of CH2Cl2 and 2 mL of i-propanol) at rt was added 4-fluorobenzaldehyde (62 mg, 0.50 mmol). The reaction mixture was stirred at rt overnight. The next morning, sodium borohydride (37 mg, 1.00 mmol) was added, and the mixture was stirred at rt for 2 h. The reaction mixture was quenched by adding 3 mL of MeOH and 3 ml of saturated aq NaHCO3. The reaction mixture was extracted with EtOAc (3×50 mL). The combined organic extracts were dried, concentrated and purified by prep HPLC to give the title compound (164 mg, 57%) as a white solid. MS (ESI): 577.0 (M+H)+.

Workup

  1. stirringthe mixture was stirred at rt for 2 h
  2. customThe reaction mixture was quenched
  3. additionby adding 3 mL of MeOH and 3 ml of saturated aq NaHCO3
  4. extractionThe reaction mixture was extracted with EtOAc (3×50 mL)
  5. customThe combined organic extracts were dried
  6. concentrationconcentrated
  7. custompurified by prep HPLC

Sources & evidence

ORD record
ord-d411041a04ed4ca0bb7f576347a039da
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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