Water → HCID 86641100, compound

HRID 1809605Notes

Reaction equation

HRID 1809605 reaction equation
[O:1]([C:8]1[C:9]([NH:21][C:22]2[S:23][CH:24]=[C:25]([CH:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)[N:26]=2)=[N:10][CH:11]=[C:12]([S:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:33]([O:37][C:38]([N-:40][S:41](N1C=CC(=[N+](C)C)C=C1)(=[O:43])=[O:42])=[O:39])([CH3:36])([CH3:35])[CH3:34].O>ClCCl>[O:1]([C:8]1[C:9]([NH:21][C:22]2[S:23][CH:24]=[C:25]([CH:27]3[CH2:32][CH2:31][N:30]([S:41]([NH:40][C:38](=[O:39])[O:37][C:33]([CH3:35])([CH3:34])[CH3:36])(=[O:42])=[O:43])[CH2:29][CH2:28]3)[N:26]=2)=[N:10][CH:11]=[C:12]([S:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 86641101HCID 86641101, compoundHCID 178482962HCID 178482962, compound

Product 1

HCID 86641100HCID 86641100, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Phenoxy-N-(4-(piperidin-4-yl)thiazol-2-yl)-5-(pyridin-2-ylthio)pyridin-2-amine (0.075 g, 0.162 mmol) and N-(tert-butoxycarbonyl)-N-[4-(dimethylazaniumylidene)-1,4-dihydropyridin-1-ylsulfonyl]azanide (0.0490 g, 0.162 mmol) were dissolved in dichloromethane (2 mL) and stirred at ambient temperature for 18 hours. Water was added and the reaction mixture was extracted with dichloromethane. The organic layer was dried, filtered and concentrated. The crude material was purified by silica gel chromatography (25-50% ethyl acetate in hexanes) provided tert-butyl 4(2-(3-phenoxy-5-(pyridin-2-ylthio)pyridin-2-ylamino)thiazol-4-yl)piperidin-1-ylsulfonylcarbamate (0.0785 g, 75.4% yield).

Workup

  1. extractionthe reaction mixture was extracted with dichloromethane
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was purified by silica gel chromatography (25-50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-c12ec50cb8dc486db18bfeba34e71db6
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

Loading…