4-Aminopyridine → (S)-4-(tert-butoxycarbonylamino)-N-(4-pyridyl)thiochromane-7-carboxamide

HRID 585741Notes

Reaction equation

HRID 585741 reaction equation
C(#N)C.[C:4]([O:8][C:9]([NH:11][C@@H:12]1[C:21]2[C:16](=[CH:17][C:18]([C:22]([OH:24])=O)=[CH:19][CH:20]=2)[S:15][CH2:14][CH2:13]1)=[O:10])([CH3:7])([CH3:6])[CH3:5].[NH2:25][C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1.[I-].ClC1C=CC=C[N+]=1C>O.C(N(CC)CC)C>[C:4]([O:8][C:9]([NH:11][C@@H:12]1[C:21]2[C:16](=[CH:17][C:18]([C:22]([NH:25][C:26]3[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=3)=[O:24])=[CH:19][CH:20]=2)[S:15][CH2:14][CH2:13]1)=[O:10])([CH3:5])([CH3:6])[CH3:7]

Participants

7

Reactant 4

HCID 17274-AminopyridineHCID 6342AcetonitrileHCID 1670692-Chloro-1-methylpyridinium iodideHCID 59089455(S)-4-(tert-butoxycarbonylamino)thiochromane-7-carboxylic acid

Product 1

HCID 59089483(S)-4-(tert-butoxycarbonylamino)-N-(4-pyridyl)thiochromane-7-carboxamideYield 67.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

To an acetonitrile (75 ml) solution of (S)-4-(tert-butoxycarbonylamino)thiochromane-7-carboxylic acid (1.00 g) and 4-aminopyridine (335 mg) were added triethylamine (1.35 ml) and 2-chloro-1-methylpyridinium iodide (991 mg), and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture and extracted with ethyl acetate. The obtained organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent of this solution was evaporated and purified by silica gel column chromatography (chloroform-methanol) to give the objective (S)-4-(tert-butoxycarbonylamino)-N-(4-pyridyl)thiochromane-7-carboxamide (845 mg) as pale yellow crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe obtained organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent of this solution was evaporated
  5. custompurified by silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-2f55b9d7148b432cbac97c5a6e1d5dc2
Source dataset
uspto-grants-2005_08
Patent number
US06933305B2

Reaction notes

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