Triethylamine → N,N-bis(4-methoxybenzyl)-4-(2-(6-methoxypyridin-3-ylamino)-5-(1-(3-(methylsulfonyl)azetidin-1-yl)ethyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine

HRID 1621890Notes

Reaction equation

HRID 1621890 reaction equation
C(N(CC)CC)C.[CH3:8][S:9]([CH:12]1[CH2:15][NH:14][CH2:13]1)(=[O:11])=[O:10].CS(O[CH:21]([C:23]1[CH:24]=[N:25][C:26]([NH:55][C:56]2[CH:57]=[N:58][C:59]([O:62][CH3:63])=[CH:60][CH:61]=2)=[C:27]([C:29]2[N:34]=[C:33]([N:35]([CH2:45][C:46]3[CH:51]=[CH:50][C:49]([O:52][CH3:53])=[CH:48][CH:47]=3)[CH2:36][C:37]3[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=3)[N:32]=[C:31]([CH3:54])[N:30]=2)[CH:28]=1)[CH3:22])(=O)=O>C(Cl)Cl>[CH3:53][O:52][C:49]1[CH:48]=[CH:47][C:46]([CH2:45][N:35]([CH2:36][C:37]2[CH:38]=[CH:39][C:40]([O:43][CH3:44])=[CH:41][CH:42]=2)[C:33]2[N:34]=[C:29]([C:27]3[C:26]([NH:55][C:56]4[CH:57]=[N:58][C:59]([O:62][CH3:63])=[CH:60][CH:61]=4)=[N:25][CH:24]=[C:23]([CH:21]([N:14]4[CH2:15][CH:12]([S:9]([CH3:8])(=[O:11])=[O:10])[CH2:13]4)[CH3:22])[CH:28]=3)[N:30]=[C:31]([CH3:54])[N:32]=2)=[CH:51][CH:50]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 529112743-(Methylsulfonyl)azetidineHCID 86647071HCID 86647071, compound

Product 1

HCID 66600253N,N-bis(4-methoxybenzyl)-4-(2-(6-methoxypyridin-3-ylamino)-5-(1-(3-(methylsulfonyl)azetidin-1-yl)ethyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amineYield 35.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

Triethylamine (0.327 mL, 2.345 mmol) and 3-(methylsulfonyl)azetidine (PharmaBlock, Carrboro, N.C.; 241 mg, 1.786 mmol) were sequentially added to a solution of 1-(5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)ethyl methanesulfonate (375 mg, 0.558 mmol) in CH2Cl2 (5.5 mL) and the resulting mixture was stirred at 25° C. for 21 h. The reaction mixture was then concentrated in vacuo and chromatographically purified (silica gel, 0 to 100% (10% MeOH-EtOAc)/hexanes) to furnish N,N-bis(4-methoxybenzyl)-4-(2-(6-methoxypyridin-3-ylamino)-5-(1-(3-(methylsulfonyl)azetidin-1-yl)ethyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (141.0 mg, 0.198 mmol, 35.5% yield) as a yellow oil. m/z (ESI, +ve) 711.3 (M+H)+.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customchromatographically purified (silica gel, 0 to 100% (10% MeOH-EtOAc)/hexanes)

Sources & evidence

ORD record
ord-95bf8fc200ac4328a76b8e36f5b40ea7
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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