4-Aminopyridine → 1-(4-(4-(3-Oxa-8-azabicyclo(3.2.1)octan-8-yl)-6-morpholino-1,3,5-triazin-2-yl)phenyl)-3-(pyridin-4-yl)urea

HRID 1513413Notes

Reaction equation

HRID 1513413 reaction equation
[N:1]1([C:7]2[N:12]=[C:11]([N:13]3[CH:18]4[CH2:19][CH2:20][CH:14]3[CH2:15][O:16][CH2:17]4)[N:10]=[C:9]([C:21]3[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=3)[N:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.CCN(CC)CC.ClC(Cl)(O[C:39](=[O:45])OC(Cl)(Cl)Cl)Cl.[NH2:47][C:48]1[CH:53]=[CH:52][N:51]=[CH:50][CH:49]=1>C(Cl)(Cl)Cl>[N:1]1([C:7]2[N:12]=[C:11]([N:13]3[CH:14]4[CH2:20][CH2:19][CH:18]3[CH2:17][O:16][CH2:15]4)[N:10]=[C:9]([C:21]3[CH:27]=[CH:26][C:24]([NH:25][C:39]([NH:47][C:48]4[CH:53]=[CH:52][N:51]=[CH:50][CH:49]=4)=[O:45])=[CH:23][CH:22]=3)[N:8]=2)[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 17274-AminopyridineHCID 8471TriethylamineHCID 94429TriphosgeneHCID 670216444-[4-Morpholin-4-yl-6-(3-oxa-8-azabicyclo[3.2.1]oct-8-yl)-1,3,5-triazin-2-yl]aniline

Product 1

HCID 469472641-(4-(4-(3-Oxa-8-azabicyclo(3.2.1)octan-8-yl)-6-morpholino-1,3,5-triazin-2-yl)phenyl)-3-(pyridin-4-yl)ureaYield 30%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 4-[4-morpholin-4-yl-6-(3-oxa-8-azabicyclo[3.2.1]oct-8-yl)-1,3,5-triazin-2-yl]aniline (22 mg, 0.06 mmol) in CHCl3 (1 mL) were added Et3N (25 mL, 0.18 mmol) and triphosgene (18 mg, 0.06 mmol). The mixture was stirred at room temperature for 15 min and 4-aminopyridine (17 mg, 0.18 mmol) was added. The mixture was stirred at room temperature overnight. The solvent was removed, and the residue was subjected to HPLC separation to give the title compound as off-white solid (1TFA salt, 8.8 mg, 24% yield). MS (ESI) m/z 489.2.

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. customThe solvent was removed
  3. customthe residue was subjected to HPLC separation

Sources & evidence

ORD record
ord-32afabe06b144b4fbdf3a85505db6ff1
Source dataset
uspto-grants-2012_07
Patent number
US08217036B2

Reaction notes

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