4-Aminopyridine → HCID 44514774, compound

HRID 404419Notes

Reaction equation

HRID 404419 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-53dced68ba474cd6abc6883c71d970de
Source dataset
uspto-grants-2014_06
Patent number
US08748421B2

Reaction notes

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