2-Fluoropyridine → HCID 136504481, compound

HRID 1507510Notes

Reaction equation

HRID 1507510 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:15](=[O:16])[NH:14][C:13]([CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[N:12][C:11]=1[NH:23][C@@H:24]1[CH2:29][CH2:28][CH2:27][N:26]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:25]1.F[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:15](=[O:16])[NH:14][C:13]([CH:17]2[CH2:18][CH2:19][N:20]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=3)[CH2:21][CH2:22]2)=[N:12][C:11]=1[NH:23][C@@H:24]1[CH2:29][CH2:28][CH2:27][N:26]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:25]1

Participants

5

Reactant 3

HCID 97462-FluoropyridineHCID 11430Potassium CarbonateHCID 136504489HCID 136504489, compound

Product 1

HCID 136504481HCID 136504481, compoundYield 41.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Into a 25-mL round-bottom flask, was placed a solution of tert-butyl (3R)-3-[[5-(1,3-benzothiazol-2-yl)-6-oxo-2-(piperidin-4-yl)-1,6-dihydropyrimidin-4-yl]amino]piperidine-1-carboxylate (150 mg, 0.29 mmol, 1.00 equiv) in N,N-dimethylformamide (5 mL) and 2-fluoropyridine (114 mg, 1.17 mmol, 4.00 equiv). This was followed by the addition of potassium carbonate (81 mg, 0.59 mmol, 2.00 equiv). The resulting solution was stirred for 24 h at 100° C. The solids were filtered out. The resulting mixture was concentrated under reduced pressure. The residue was purified through a silica gel column with dichloromethane/methanol (50:1-20:1) to afford 70 mg of tert-butyl (3R)-3-[[5-(1,3-benzothiazol-2-yl)-6-oxo-2-[1-(pyridin-2-yl)piperidin-4-yl]-1,6-dihydropyrimidin-4-yl]amino]piperidine-1-carboxylate as a light yellow solid.

Workup

  1. customInto a 25-mL round-bottom flask, was placed
  2. filtrationThe solids were filtered out
  3. concentrationThe resulting mixture was concentrated under reduced pressure
  4. customThe residue was purified through a silica gel column with dichloromethane/methanol (50:1-20:1)

Sources & evidence

ORD record
ord-3d10145ac3ee40a9b8b42cd2b5102243
Source dataset
uspto-grants-2015_12
Patent number
US09221809B2

Reaction notes

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