4-Aminopyridine → HCID 44514774, compound

HRID 1513405Notes

Reaction equation

HRID 1513405 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:11]=[C:10]([NH:20][CH:21]3[CH2:24][N:23]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:22]3)[N:9]=2)=[CH:4][CH:3]=1.ClC(Cl)(O[C:36](=[O:42])OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.[NH2:51][C:52]1[CH:57]=[CH:56][N:55]=[CH:54][CH:53]=1>C(Cl)Cl>[N:14]1([C:12]2[N:13]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][C:36](=[O:42])[NH:51][C:52]4[CH:57]=[CH:56][N:55]=[CH:54][CH:53]=4)=[CH:3][CH:4]=3)[N:9]=[C:10]([NH:20][CH:21]3[CH2:24][N:23]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:22]3)[N:11]=2)[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 17274-AminopyridineHCID 8471TriethylamineHCID 94429TriphosgeneHCID 67021834HCID 67021834, compound

Product 1

HCID 44514774HCID 44514774, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 3-{[4-(4-aminophenyl)-6-morpholin-4-yl-1,3,5-triazin-2-yl]amino}azetidine-1-carboxylate (200 mg, 0.47 mmol) in DCM (100 ml) at 0° C., triphosgene (300 mg) and triethylamine (3 ml) was added slowly. The reaction mixture was stirred for 15 minutes and 4-aminopyridine (200 mg. 2.1 mmol) was added. The reaction mixture was stirred at room temperature for 24 hours and concentrated. It was quenched with cold water and the separated solid was filtered and washed with water. It was dried and purified by Gilson HPLC. Yield 100 mg (40%); (M+H) 548.6

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 24 hours
  2. concentrationconcentrated
  3. customIt was quenched with cold water
  4. filtrationthe separated solid was filtered
  5. washwashed with water
  6. customIt was dried
  7. custompurified by Gilson HPLC

Sources & evidence

ORD record
ord-2d919a084ffb4c3f8d1a6984dc93e127
Source dataset
uspto-grants-2012_07
Patent number
US08217036B2

Reaction notes

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