4-Aminopyridine → Tert-butyl 4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(4-(3-pyridin-4-ylureido)phenyl)-1,3,5-triazin-2-yl)piperazine-1-carboxylate

HRID 2094577Notes

Reaction equation

HRID 2094577 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([N:14]3[CH2:20][CH:19]4[O:21][CH:16]([CH2:17][CH2:18]4)[CH2:15]3)[N:11]=[C:10]([N:22]3[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]3)[N:9]=2)=[CH:4][CH:3]=1.ClC(Cl)(O[C:39](=[O:45])OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.[NH2:54][C:55]1[CH:60]=[CH:59][N:58]=[CH:57][CH:56]=1>O1CCCC1>[CH:16]12[O:21][CH:19]([CH2:18][CH2:17]1)[CH2:20][N:14]([C:12]1[N:13]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][C:39]([NH:54][C:55]4[CH:60]=[CH:59][N:58]=[CH:57][CH:56]=4)=[O:45])=[CH:3][CH:4]=3)[N:9]=[C:10]([N:22]3[CH2:23][CH2:24][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:26][CH2:27]3)[N:11]=1)[CH2:15]2

Participants

6

Reactant 4

HCID 17274-AminopyridineHCID 8471TriethylamineHCID 94429TriphosgeneHCID 67021837Tert-butyl 4-(4-(4-aminophenyl)-6-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1,3,5-triazin-2-yl)piperazine-1-carboxylate

Product 1

HCID 44548641Tert-butyl 4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(4-(3-pyridin-4-ylureido)phenyl)-1,3,5-triazin-2-yl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Crude tert-butyl 4-(4-(4-aminophenyl)-6-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1,3,5-triazin-2-yl)piperazine-1-carboxylate (approx. 1.4 mmol) was dissolved in tetrahydrofuran (20 mL) and then treated sequentially with triphosgene (0.30 g, 1.0 mmol) and triethylamine (2 mL). After 5 minutes, the mixture was treated with a solution of 4-aminopyridine (0.53 g, 5.6 mmol) in tetrahydrofuran. The mixture was concentrated under reduced pressure to give crude tert-butyl 4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(4-(3-pyridin-4-ylureido)phenyl)-1,3,5-triazin-2-yl)piperazine-1-carboxylate, a sample of which was purified by reversed phase HPLC to give a pure title compound.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customto give crude tert-butyl 4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(4-(3-pyridin-4-ylureido)phenyl)-1,3,5-triazin-2-yl)piperazine-1-carboxylate
  3. customa sample of which was purified by reversed phase HPLC

Sources & evidence

ORD record
ord-dbd95c7cea9640b2ae07574297e37207
Source dataset
uspto-grants-2013_05
Patent number
US08445486B2

Reaction notes

Loading…