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 982596

Reaction equation

HRID 982596 reaction equation
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]

Participants

6

Reactant 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

Product 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]propaneYield 69%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

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-1,3,5triazin-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 14.50 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) δ8.11 (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) δ165.54, 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.

Workup

  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

Sources & evidence

ORD record
ord-0c350b05eac94eed9b4c3dad5c114b0b
Source dataset
uspto-grants-2005_03
Patent number
US06860928B2

Linked notes

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