Methanol → 1,3-bis(4-[N-(2,4-bis(N-octylamino)-1,3,5-triazin-6-yl)amino]phenoxy)-2,2-bis[(4-[N-(2,4-bis(N-octylamino)-1,3,5-triazin-6-yl)amino]phenoxy)methyl]propane

HRID 1372550

반응식

HRID 1372550 반응식
Cl[C:2]1[N:7]=[C:6](Cl)[N:5]=[C:4]([NH:9][C:10]2[CH:69]=[CH:68][C:13]([O:14][CH2:15][C:16]([CH2:51][O:52][C:53]3[CH:58]=[CH:57][C:56]([NH:59][C:60]4[N:65]=[C:64](Cl)[N:63]=[C:62](Cl)[N:61]=4)=[CH:55][CH:54]=3)([CH2:34][O:35][C:36]3[CH:41]=[CH:40][C:39]([NH:42][C:43]4[N:48]=[C:47](Cl)[N:46]=[C:45](Cl)[N:44]=4)=[CH:38][CH:37]=3)[CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([NH:25][C:26]4[N:31]=[C:30](Cl)[N:29]=[C:28](Cl)[N:27]=4)=[CH:21][CH:20]=3)=[CH:12][CH:11]=2)[N:3]=1.[CH2:70]([NH2:78])[CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH3:77].[OH-].[Na+].CO>O1CCOCC1>[CH2:70]([NH:78][C:2]1[N:7]=[C:6]([NH:78][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH3:77])[N:5]=[C:4]([NH:9][C:10]2[CH:69]=[CH:68][C:13]([O:14][CH2:15][C:16]([CH2:51][O:52][C:53]3[CH:58]=[CH:57][C:56]([NH:59][C:60]4[N:65]=[C:64]([NH:78][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH3:77])[N:63]=[C:62]([NH:78][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH3:77])[N:61]=4)=[CH:55][CH:54]=3)([CH2:34][O:35][C:36]3[CH:41]=[CH:40][C:39]([NH:42][C:43]4[N:48]=[C:47]([NH:78][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH3:77])[N:46]=[C:45]([NH:78][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH3:77])[N:44]=4)=[CH:38][CH:37]=3)[CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([NH:25][C:26]4[N:31]=[C:30]([NH:78][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH3:77])[N:29]=[C:28]([NH:78][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH3:77])[N:27]=4)=[CH:21][CH:20]=3)=[CH:12][CH:11]=2)[N:3]=1)[CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH3:77]

참가 물질

6

반응물 4

HCID 887MethanolHCID 8143OctylamineHCID 14798Sodium HydroxideHCID 220154391,3-bis(4-[N-(2,4-dichloro-1,3,5-triazin-6-yl)amino]phenoxy)-2,2-bis[(4-[N-(2,4-dichloro-1,3,5-triazin-6-yl)amino]phenoxy)methyl]propane

생성물 1

HCID 220154331,3-bis(4-[N-(2,4-bis(N-octylamino)-1,3,5-triazin-6-yl)amino]phenoxy)-2,2-bis[(4-[N-(2,4-bis(N-octylamino)-1,3,5-triazin-6-yl)amino]phenoxy)methyl]propane수율 69%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

A mixture of 1,3-bis(4-[N-(2,4-dichloro-1,3,5-triazin-6-yl)amino]phenoxy)-2,2-bis[(4-[N-(2,4-dichloro-1,3,5-triazin-6-yl)amino]phenoxy)methyl]propane (3.88 grams, 3.55 mmol; prepared as described in Part D of this Example) and octylamine (11.7 milliliters, 71.0 mmol; obtained from Aldrich Chemical Co.) in dioxane (30 milliliters) was heated at reflux for 3 hours. The mixture was then cooled and added to 400 milliliters of a solution of 1 Normal NaOH and methanol (1:1 (v/v)). The resulting white solid was filtered off and dissolved in tetrahydrofuran. This solution was filtered over silica gel, and the volatiles were removed under reduced pressure. The residue was triturated in methanol and then dried under vacuum to afford pure 1,3-bis(4-[N-(2,4-bis(N-octylamino)-1,3,5-triazin-6-yl)amino]phenoxy)-2,2-bis[(4-[N-(2,4-bis(N-octylamino)—1,3,5-triazin-6-yl)amino]phenoxy)methyl]propane (4.50 grams, 2.45 mmol, 69 percent yield) as white powder: softening point 94–96° C.; IR (KBr) 3434, 3274, 2925, 2854, 1579, 1506, 1421, 1367, 1226, 1030, 810 cm−1; 1H NMR (400 MHz, DMSO-d6, 373° K.) δ 8.11 (s, 4H), 7.60 (d, 8H, 3J=8.9 Hz), 6.84 (d, 8H, 3J=8.9 Hz), 6.12 (s, 8H), 4.25 (s, 8H), 3.26 (td, 16H, 3Jt=6.6 Hz, 3Jd=6.6 Hz), 1.53 (m, 16H), 1.29 (m, 80H), 0.86 (t, 24H, 3J=7.1 Hz); 13C NMR (100 MHz, DMSO-d6, 373° K) δ 165.54, 163.77, 153.31, 133.96, 120.76, 114.27, 67.15, 44.47, 39.61, 30.56, 28.87, 28.14, 27.96, 25.90, 21.29, 13.00; MS (FAB, 3-nitrobenzyl alcohol) m/e 1834.6; Anal. Calcd for C105H172N24O4: C, 68.74; H, 9.45; N, 18.32. Found: C, 68.31; H, 9.58; N, 18.34.

후처리

  1. customprepared
  2. temperaturewas heated
  3. temperatureat reflux for 3 hours
  4. temperatureThe mixture was then cooled
  5. filtrationThe resulting white solid was filtered off
  6. dissolutiondissolved in tetrahydrofuran
  7. filtrationThis solution was filtered over silica gel
  8. customthe volatiles were removed under reduced pressure
  9. customThe residue was triturated in methanol
  10. customdried under vacuum

출처 및 근거

ORD 기록
ord-542667c905134d46837d063e79362a76
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07157601B2

연결된 노트

불러오는 중…