Tributylphosphine → HCID 58398388, compound

HRID 1879413Notes

Reaction equation

HRID 1879413 reaction equation
[F:1][C@@H:2]([CH3:24])[CH2:3][N:4]([C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][C:22]=1[OH:23])[CH2:19][CH2:18][CH2:17]2)[S:5]([C:8]1[S:9][CH:10]=[C:11]([CH3:13])[N:12]=1)(=[O:7])=[O:6].C(P(CCCC)CCCC)CCC.O[CH2:39][C:40]1[CH:41]=[CH:42][C:43]([C:46]([O:48][CH2:49][CH3:50])=[O:47])=[N:44][CH:45]=1.N(/C(N1CCCCC1)=O)=N\C(N1CCCCC1)=O>C1COCC1>[F:1][C@@H:2]([CH3:24])[CH2:3][N:4]([S:5]([C:8]1[S:9][CH:10]=[C:11]([CH3:13])[N:12]=1)(=[O:7])=[O:6])[C:14]1[CH:15]=[C:16]2[C:20]([CH2:19][CH2:18][CH2:17]2)=[CH:21][C:22]=1[O:23][CH2:39][C:40]1[CH:41]=[CH:42][C:43]([C:46]([O:48][CH2:49][CH3:50])=[O:47])=[N:44][CH:45]=1

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 5702657diazenedicarboxylic acid bis(N,N-piperidide)HCID 13518564Ethyl 5-(hydroxymethyl)pyridine-2-carboxylateHCID 58398469N-[(2S)-2-fluoropropyl]-N-(6-hydroxy-2,3-dihydro-1H-inden-5-yl)-4-methyl-1,3-thiazole-2-sulfonamide

Product 1

HCID 58398388HCID 58398388, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

133 mg of N-[(2S)-2-fluoropropyl]-N-(6-hydroxy-2,3-dihydro-1H-inden-5-yl)-4-methyl-1,3-thiazole-2-sulfonamide, 94.4 mg of tributylphosphine, and 71.5 mg of ethyl 5-(hydroxymethyl)pyridine-2-carboxylate were dissolved in 1.33 mL of THF, and 118 mg of 1,1′-[(E)-diazene-1,2-diyldicarbonyl]dipiperidine was added thereto, followed by stirring overnight at room temperature. After the insoluble materials were removed by filtration, the solvent was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=80:20) to obtain 116 mg of ethyl 5-{[(6-{[(2S)-2-fluoropropyl][(4-methyl-1,3-thiazol-2-yl)sulfonyl]amino}-2,3-dihydro-1H-inden-5-yl)oxy]methyl}pyridine-2-carboxylate.

Workup

  1. customAfter the insoluble materials were removed by filtration
  2. concentrationthe solvent was concentrated under reduced pressure
  3. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=80:20)

Sources & evidence

ORD record
ord-4b90824504ac4b23bb65fa8237d162ed
Source dataset
uspto-grants-2012_11
Patent number
US08314240B2

Reaction notes

Loading…