Dimethylamine → 4-tert-Butyl-N-[4-chloro-2-(5-dimethylaminomethyl-[1,2,3]triazol-1-yl)-phenyl]-benzenesulfonamide

HRID 1480912Notes

Reaction equation

HRID 1480912 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[N:22]2[C:26]([CH:27](OCC)OCC)=[CH:25][N:24]=[N:23]2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CC(OC(C)=O)=O.[N:41]1[CH:46]=CC=C[CH:42]=1.CNC.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CCOCC>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[N:22]2[C:26]([CH2:27][N:41]([CH3:46])[CH3:42])=[CH:25][N:24]=[N:23]2)(=[O:12])=[O:13])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 22348678Acetic anhydride pyridineHCID 594281314-tert-butyl-N-[4-chloro-2-(5-diethoxymethyl-[1,2,3]triazol-1-yl)-phenyl]-benzenesulfonamide

Product 1

HCID 594281344-tert-Butyl-N-[4-chloro-2-(5-dimethylaminomethyl-[1,2,3]triazol-1-yl)-phenyl]-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A 30 mL scintillation vial was charged with 4-tert-butyl-N-[4-chloro-2-(5-diethoxymethyl-[1,2,3]triazol-1-yl)-phenyl]-benzenesulfonamide (synthesized according to general procedure Q, 1.0 g, 2.0 mmol) and Ac2O/pyridine (1:2 v/v, 6 mL), and stirred at room temperature for 4 hours. The reaction mixture was subsequently diluted with Et2O and washed with 1 M HCl, saturated NaHCO3, and brine. The combined organics were then dried over Na2SO4 and concentrated in vacuo. The resultant product (35 mg, 0.075 mmol) and dimethyl amine (80 L, 2.0 M in THF) were combined in a 4 mL scintillation vial and stirred for 30 minutes. NaBH(OAc)3 (32 mg, 0.17 mmol) was then added and the reaction was stirred for 12 hours at room temperature. The reaction mixture was subsequently diluted with Et2O, washed with 1 M HCl, and the combined organics were purified by preparative TLC to generate 4-tert-butyl-N-[4-chloro-2-(5-dimethylaminomethyl-[1,2,3]triazol-1-yl)-phenyl]-benzenesulfonamide: MS (ES) M+H expected 448.2, found 448.4.

Workup

  1. washwashed with 1 M HCl, saturated NaHCO3, and brine
  2. dry with materialThe combined organics were then dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. stirringstirred for 30 minutes
  5. stirringthe reaction was stirred for 12 hours at room temperature
  6. washwashed with 1 M HCl
  7. customthe combined organics were purified by preparative TLC

Sources & evidence

ORD record
ord-c1af3d02579f4aa7826c46bc988a9c88
Source dataset
uspto-grants-2016_08
Patent number
US09409909B2

Reaction notes

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