NBD-Cl → 4-Dodecyl-N-(5-(5-(methyl(7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)amino)pentyl)-1,3,4-thiadiazol-2-yl)benzenesulfonamide

HRID 631082

반응식

HRID 631082 반응식
Cl[C:2]1[C:10]2[C:6](=[N:7][O:8][N:9]=2)[C:5]([N+:11]([O-:13])=[O:12])=[CH:4][CH:3]=1.[CH2:14]([C:26]1[CH:31]=[CH:30][C:29]([S:32]([NH:35][C:36]2[S:37][C:38]([CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][NH:46][CH3:47])=[N:39][N:40]=2)(=[O:34])=[O:33])=[CH:28][CH:27]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].C([O-])(O)=O.[Na+]>CO>[CH2:14]([C:26]1[CH:27]=[CH:28][C:29]([S:32]([NH:35][C:36]2[S:37][C:38]([CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][N:46]([CH3:47])[C:2]3[C:10]4[C:6](=[N:7][O:8][N:9]=4)[C:5]([N+:11]([O-:13])=[O:12])=[CH:4][CH:3]=3)=[N:39][N:40]=2)(=[O:33])=[O:34])=[CH:30][CH:31]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

참가 물질

5

반응물 3

HCID 25043NBD-ClHCID 516892Sodium BicarbonateHCID 583025024-dodecyl-N-(5-(5-(methylamino)pentyl)-1,3,4-thiadiazol-2-yl)benzenesulfonamide

생성물 1

HCID 583026394-Dodecyl-N-(5-(5-(methyl(7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)amino)pentyl)-1,3,4-thiadiazol-2-yl)benzenesulfonamide수율 53%

시약·촉매·용매 1

HCID 887Methanol용매2회

반응 조건

온도
40 °C

실험 절차

4-Chloro-7-nitro-2,1,3-benzoxadiazole (NBD-Cl) (18 mg, 0.085 mmol) was dissolved in methanol (1 mL). After the addition of 4-dodecyl-N-(5-(5-(methylamino)pentyl)-1,3,4-thiadiazol-2-yl)benzenesulfonamide (43 mg, 0.085 mmol) and NaHCO3 (7 mg, 0.085 mmol) in methanol (2 mL), the solution was stirred for 2 h at 40° C. The reaction mixture was evaporated to dryness under reduced pressure and the residue was chromatographed on silica gel 60 (70-230 mesh) eluted with CH2Cl2:MeOH 49:1. Product 137 was obtained in 53% yield (30 mg, 0.045 mmol), mp 102-104° C. 1H NMR (300 MHz, CDCl3) δ 0.87 (t, 3, J=7.2 Hz), 1.25 (m, 18), 1.51-1.57 (m, 4), 1.79-1.85 (m, 4), 2.63 (t, 2, J=6.6 Hz), 2.84 (t, 2, J=7.5 Hz), 3.45 (s, 3), 4.14 (s, 2), 6.11 (d, 1, J=9.3 Hz), 7.27 (d, 2, J=8.1 Hz), 7.79 (d, 2, J=8.4 Hz), 8.44 (d, 1, J=9.0 Hz); 13C NMR (75 MHz, CDCl3) δ 14.1, 22.6, 25.7, 27.7, 29.2, 29.3, 29.4, 29.5, 29.6, 30.4, 31.1, 31.9, 35.9, 55.6, 101.2, 126.5, 128.9, 135.4, 138.3, 145.3, 148.5, 154.7, 158.3, 163.8, 167.9; HRMS (ESI+, m/z) calculated for C32H46N7O5S2 672.3002. observed 672.2996 (M+H)+.

후처리

  1. customThe reaction mixture was evaporated to dryness under reduced pressure
  2. customthe residue was chromatographed on silica gel 60 (70-230 mesh)
  3. washeluted with CH2Cl2:MeOH 49:1

출처 및 근거

ORD 기록
ord-9f3b0e4c3c8f41de8aa2b6a6f7320b02
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09320734B2

연결된 노트

불러오는 중…