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 2037077Notes

Reaction equation

HRID 2037077 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-54aea61ff53543ae94cd527bbd3e230f
Source dataset
uspto-grants-2013_11
Patent number
US08575159B2

Reaction notes

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