HCID 58736381, compound → HCID 71525424, compound

HRID 1528183Notes

Reaction equation

HRID 1528183 reaction equation
[OH:1][C:2]1[C:7]([NH:8][C:9]2[C:12](=[O:13])[C:11](=[O:14])[C:10]=2OC)=[CH:6][CH:5]=[CH:4][C:3]=1[S:17]([N:20]([CH3:22])[CH3:21])(=[O:19])=[O:18].[CH3:23][C:24]1[O:28][C:27]([CH:29]([NH2:35])[C:30]2([CH3:34])[CH2:33][O:32][CH2:31]2)=[CH:26][CH:25]=1>CO>[OH:1][C:2]1[C:7]([NH:8][C:9]2[C:12](=[O:13])[C:11](=[O:14])[C:10]=2[NH:35][CH:29]([C:27]2[O:28][C:24]([CH3:23])=[CH:25][CH:26]=2)[C:30]2([CH3:34])[CH2:31][O:32][CH2:33]2)=[CH:6][CH:5]=[CH:4][C:3]=1[S:17]([N:20]([CH3:22])[CH3:21])(=[O:19])=[O:18]

Participants

4

Reactant 2

HCID 58736381HCID 58736381, compoundHCID 89525357C-(5-methylfuran-2-yl)-C-(3-methyloxetan-3-yl)methylamine

Product 1

HCID 71525424HCID 71525424, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 284 mg (0.87 mmol, 1 eq) of 2-hydroxy-3-(2-methoxy-3,4-dioxocyclobut-1-enylamino)-N,N-dimethylbenzenesulfonamide and 318 mg (1.75 mmol) of C-(5-methylfuran-2-yl)-C-(3-methyloxetan-3-yl)methylamine in 20 ml of methanol was heated at 50° C. for 3 days. The reaction medium was concentrated. The residue was taken up in ethyl acetate and was washed twice with a 1 M aqueous sodium dihydrogen phosphate solution. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated. 0.29 g of product was obtained in the form of an ochre solid. Yield=70%, HPLC=98.68%, Mp=123° C.

Workup

  1. concentrationThe reaction medium was concentrated
  2. washwas washed twice with a 1 M aqueous sodium dihydrogen phosphate solution
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-54e8a16d5c28489f8b356f14ac3217ab
Source dataset
uspto-grants-2015_07
Patent number
US09090596B2

Reaction notes

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