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 8416

反応式

HRID 8416 の反応式
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]

参加物

6

反応物 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

生成物 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]propane収率 69%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9d76751d333c489db5273cd46d72fe74
出典データセット
uspto-grants-2006_08
特許番号
US07087752B2

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