Dichloromethane → 4-(2-(5-fluoro-6-methoxypyridin-3-ylamino)-5-(piperazin-1-ylmethyl)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine

HRID 1811817Notes

Reaction equation

HRID 1811817 reaction equation
[CH3:1][O:2][C:3]1[CH:56]=[CH:55][C:6]([CH2:7][N:8]([CH2:46][C:47]2[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[CH:49][CH:48]=2)[C:9]2[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([C:16]3[CH:17]=[C:18]([CH2:32][N:33]4[CH2:38][CH2:37][N:36](C(OC(C)(C)C)=O)[CH2:35][CH2:34]4)[CH:19]=[N:20][C:21]=3[NH:22][C:23]3[CH:24]=[N:25][C:26]([O:30][CH3:31])=[C:27]([F:29])[CH:28]=3)[N:10]=2)=[CH:5][CH:4]=1.ClCCl.FC(F)(F)C(O)=O>>[F:29][C:27]1[CH:28]=[C:23]([NH:22][C:21]2[C:16]([C:11]3[N:12]=[C:13]([CH3:15])[N:14]=[C:9]([N:8]([CH2:7][C:6]4[CH:55]=[CH:56][C:3]([O:2][CH3:1])=[CH:4][CH:5]=4)[CH2:46][C:47]4[CH:48]=[CH:49][C:50]([O:53][CH3:54])=[CH:51][CH:52]=4)[N:10]=3)=[CH:17][C:18]([CH2:32][N:33]3[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]3)=[CH:19][N:20]=2)[CH:24]=[N:25][C:26]=1[O:30][CH3:31]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 66600044Tert-butyl 4-((5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)methyl)piperazine-1-carboxylate

Product 1

HCID 665999414-(2-(5-fluoro-6-methoxypyridin-3-ylamino)-5-(piperazin-1-ylmethyl)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amineYield 92%

Procedure

A solution of tert-butyl 4-((5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)methyl)piperazine-1-carboxylate (25 g, 32.6 mmol) in dichloromethane (150 mL, 32.6 mmol) and trifluoroacetic acid (150 mL, 2019 mmol) was stirred at room temperature for 1 h. The solution was concentrated and the residue was dissolved in DCM and carefully neutralized with saturated aqueous NaHCO3. The aqueous layer was extracted with DCM and the organic extracts were dried over Na2SO4, filtered and concentrated in vacuo to give 4-(2-(5-fluoro-6-methoxypyridin-3-ylamino)-5-(piperazin-1-ylmethyl)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (20 g, 30.0 mmol, 92% yield). The crude product was taken on to the next step without purification.

Workup

  1. concentrationThe solution was concentrated
  2. dissolutionthe residue was dissolved in DCM
  3. extractionThe aqueous layer was extracted with DCM
  4. dry with materialthe organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-285542cfa23641e5a1c4178b722686e6
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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