Hydrochloric Acid → (S)-Ethyl (N-{[5-({3-[(3-methyl-2-furoyl)amino]phenyl}ethynyl)pyridin-3-yl]carbonyl}-S-phenylsulfonimidoyl)acetate

HRID 391604Notes

Reaction equation

HRID 391604 reaction equation
[C:1]1([S@@:7]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])(=[NH:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:16][C:17]1[CH:21]=[CH:20][O:19][C:18]=1[C:22]([NH:24][C:25]1[CH:26]=[C:27]([C:31]#[C:32][C:33]2[CH:34]=[N:35][CH:36]=[C:37]([CH:41]=2)[C:38](O)=[O:39])[CH:28]=[CH:29][CH:30]=1)=[O:23].Cl.CN(C)CCCN=C=NCC.Cl>CN(C=O)C.CN(C)C1C=CN=CC=1>[CH3:16][C:17]1[CH:21]=[CH:20][O:19][C:18]=1[C:22]([NH:24][C:25]1[CH:26]=[C:27]([C:31]#[C:32][C:33]2[CH:41]=[C:37]([C:38]([N:9]=[S@:7]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[O:8])=[O:39])[CH:36]=[N:35][CH:34]=2)[CH:28]=[CH:29][CH:30]=1)=[O:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 576578475-((3-(3-Methylfuran-2-carboxamido)phenyl)ethynyl)nicotinic acidHCID 57657864(S)-Ethyl (S-phenylsulfonimidoyl)acetate

Product 1

HCID 57657941(S)-Ethyl (N-{[5-({3-[(3-methyl-2-furoyl)amino]phenyl}ethynyl)pyridin-3-yl]carbonyl}-S-phenylsulfonimidoyl)acetateYield 43.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl (S)-(S-phenylsulfonimidoyl)acetate (139 mg, 0.61 mmol) in anhydrous DMF (3 mL) at room temperature was added 5-{3-[(3-Methyl-furan-2-carbonyl)-amino]-phenylethynyl}-nicotinic acid (233 mg), catalytic amount of 4-(dimethylamino)pyridine, and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (141 mg). The reaction mixture was stirred at room temperature for 30 min. The reaction was then poured into aqueous HCl (0.5%) and extracted with EtOAc. After the aqueous layer was separated, solid sodium chloride was added and the resulting aqueous mixture was extracted again with EtOAc. The organic layers were combined, washed with brine (1×), saturated aqueous NaHCO3 (1×), then brine (1×), and finally dried with sodium sulfate. The upper solution was decanted, concentrated, and the yellow oily residue was subject to a column chromatography (silica gel, gradient elution EtOAc-Hex from 1:5 to 1:1.5) to give the title compound as a white foam (147 mg, 43%).

Workup

  1. extractionextracted with EtOAc
  2. customAfter the aqueous layer was separated
  3. additionsolid sodium chloride was added
  4. extractionthe resulting aqueous mixture was extracted again with EtOAc
  5. washwashed with brine (1×), saturated aqueous NaHCO3 (1×)
  6. dry with materialbrine (1×), and finally dried with sodium sulfate
  7. customThe upper solution was decanted
  8. concentrationconcentrated
  9. washthe yellow oily residue was subject to a column chromatography (silica gel, gradient elution EtOAc-Hex from 1:5 to 1:1.5)

Sources & evidence

ORD record
ord-56458d06ae5647dbac5b196748d49a0a
Source dataset
uspto-grants-2013_02
Patent number
US08383825B2

Reaction notes

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