4-Aminopyridine → HCID 44548481, compound

HRID 2094570Notes

Reaction equation

HRID 2094570 reaction equation
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[CH3:13][N:14]1[CH:19]2[CH2:20][CH2:21][CH:15]1[CH2:16][CH:17]([O:22][C:23]1[N:28]=[C:27]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)[N:26]=[C:25]([C:35]3[CH:40]=[CH:39][C:38]([NH2:41])=[CH:37][CH:36]=3)[N:24]=1)[CH2:18]2.[NH2:42][C:43]1[CH:48]=[CH:47][N:46]=[CH:45][CH:44]=1.CCN(CC)CC>C(Cl)Cl>[CH3:13][N:14]1[CH:15]2[CH2:21][CH2:20][CH:19]1[CH2:18][CH:17]([O:22][C:23]1[N:28]=[C:27]([N:29]3[CH2:30][CH2:31][O:32][CH2:33][CH2:34]3)[N:26]=[C:25]([C:35]3[CH:36]=[CH:37][C:38]([NH:41][C:5]([NH:42][C:43]4[CH:48]=[CH:47][N:46]=[CH:45][CH:44]=4)=[O:11])=[CH:39][CH:40]=3)[N:24]=1)[CH2:16]2

Participants

6

Reactant 4

HCID 17274-AminopyridineHCID 8471TriethylamineHCID 94429TriphosgeneHCID 67021927HCID 67021927, compound

Product 1

HCID 44548481HCID 44548481, compoundYield 27.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of triphosgene (60 mg, 0.20 mmol) in CH2Cl2 (3 mL) was added 4-[4-(8-Methyl-8-aza-bicyclo[3.2.1]oct-3-yloxy)-6-morpholin-4-yl-[1,3,5]triazin-2-yl]-phenylamine (100 mg, 0.25 mmol) at 25° C. The reaction mixture was stirred for 15 min and 4-aminopyridine (70 mg, 0.75 mmol) and NEt3 (346 μL, 2.5 mmol) were added and the reaction mixture was stirred for additional 1 hr. The solvents were removed and the crude mixture was purified by semi-prep-HPLC (NH3-method) to give 1-{4-[4-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yloxy)-6-morpholin-4-yl-[1,3,5]triazin-2-yl]-phenyl}-3-pyridin-4-yl-urea (28 mg, 22% yield); MS (ESI)m/z 517.

Workup

  1. stirringthe reaction mixture was stirred for additional 1 hr
  2. customThe solvents were removed
  3. customthe crude mixture was purified by semi-prep-HPLC (NH3-method)

Sources & evidence

ORD record
ord-cb1108cf2b7b4400b6b3641873d0f0c2
Source dataset
uspto-grants-2013_05
Patent number
US08445486B2

Reaction notes

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