Sodium Carbonate → tert-butyl {2-[{2-[3-(2-fluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]ethyl}(methyl)amino]ethyl}methylcarbamate

HRID 1818810노트

반응식

HRID 1818810 반응식
Br[CH2:2][CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])[S:5]1(=[O:21])=[O:20].[CH3:22][N:23]([CH2:31][CH2:32][NH:33][CH3:34])[C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[F:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[N:6]1[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:4]([CH2:3][CH2:2][N:33]([CH3:34])[CH2:32][CH2:31][N:23]([CH3:22])[C:24](=[O:30])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[S:5]1(=[O:21])=[O:20]

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 14403871tert-Butyl methyl(2-(methylamino)ethyl)carbamateHCID 68711997HCID 68711997, 화합물

생성물 1

HCID 86621288tert-butyl {2-[{2-[3-(2-fluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]ethyl}(methyl)amino]ethyl}methylcarbamate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
125 °C

실험 절차

A mixture of 1-(2-bromoethyl)-3-(2-fluorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide (171 mg, 0.461 mmol), tert-butyl methyl[2-(methylamino)ethyl]carbamate (695 mg, 3.69 mmol, 8 equiv.), sodium carbonate (489 mg, 4.61 mmol, 10 equiv.) and N,N-dimethylformamide (5 mL) was sealed and heated at 125° C. for 5 h. After cooling, the reaction mixture was partitioned between ethyl acetate (40 mL) and water (40 mL). The organic layer was washed with brine, dried (anhydrous sodium sulfate), and concentrated. The crude liquid was pre-adsorbed onto Florisil and purified via Isco flash column chromatography (12-g redisep silica gel column, 15-70% ethyl acetate/hexane) to give tert-butyl {2-[{2-[3-(2-fluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]ethyl}(methyl)amino]ethyl}methylcarbamate as a viscous, colorless liquid. Yield: 142 mg (64%). MS (ESI) m/z 479.0 ([M+H]+). HRMS: calcd for C23H31FN4O4S+H+, 479.2123; found (ESI, [M+H]+), 479.2129. HPLC purity 96.6% at 210-370 nm, 9.0 min.; Xterra RP18, 3.5 u, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN+MeOH) for 10 min, hold 4 min.

후처리

  1. customwas sealed
  2. temperatureAfter cooling
  3. customthe reaction mixture was partitioned between ethyl acetate (40 mL) and water (40 mL)
  4. washThe organic layer was washed with brine
  5. dry with materialdried (anhydrous sodium sulfate)
  6. concentrationconcentrated
  7. custompurified via Isco flash column chromatography (12-g redisep silica gel column, 15-70% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-bae0199e3fbc421c993ef6f376dd56a8
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07601722B2

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