HCID 68705514, compound → HCID 68711908, compound

HRID 1809657Notes

Reaction equation

HRID 1809657 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][S:5][C:6]1[CH:7]=[C:8]([O:31][C:32]2[C:33]([CH3:38])=[N:34][CH:35]=[CH:36][CH:37]=2)[C:9]([NH:12][C:13]2[S:17][N:16]=[C:15]([CH:18]3[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]3)[N:14]=2)=[N:10][CH:11]=1>C(O)(C(F)(F)F)=O>[CH3:1][O:2][CH2:3][CH2:4][S:5][C:6]1[CH:7]=[C:8]([O:31][C:32]2[C:33]([CH3:38])=[N:34][CH:35]=[CH:36][CH:37]=2)[C:9]([NH:12][C:13]2[S:17][N:16]=[C:15]([CH:18]3[CH2:19][CH2:20][NH:21][CH2:22][CH2:23]3)[N:14]=2)=[N:10][CH:11]=1

Participants

3

Reactant 1

HCID 68705514HCID 68705514, compound

Product 1

HCID 68711908HCID 68711908, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A flask was charged with tert-butyl 4-(5-(5-(2-methoxyethylthio)-3-(2-methylpyridin-3-yloxy)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)piperidine-1-carboxylate (376 mg, 0.673 mmol) in TFA (5 mL), and the reaction was stirred for 15 minutes. The reaction mixture was concentrated and redissolved in 10% methanol in dichloromethane. Saturated sodium bicarbonate was added. The mixture was filtered, and the organic layer was separated, dried, filtered to provide N-(5-(2-methoxyethylthio)-3-(2-methylpyridin-3-yloxy)pyridin-2-yl)-3-(piperidin-4-yl)-1,2,4-thiadiazol-5-amine (298 mg, 0.650 mmol, 96.6% yield).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionredissolved in 10% methanol in dichloromethane
  3. additionSaturated sodium bicarbonate was added
  4. filtrationThe mixture was filtered
  5. customthe organic layer was separated
  6. customdried
  7. filtrationfiltered

Sources & evidence

ORD record
ord-f2af3fba9719415ba40bfba9b47565dc
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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