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

HRID 218205노트

반응식

HRID 218205 반응식
[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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

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 μL, 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.

후처리

  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

출처 및 근거

ORD 기록
ord-c54174d4ad51466ba1517bc4efb2bf52
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198309B2

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