C-(5-methylfuran-2-yl)-C-(3-methyloxetan-3-yl)methylamine → HCID 71525973, compound

HRID 1528209Notes

Reaction equation

HRID 1528209 reaction equation
[F:1][C:2]1[C:18]([NH:19][C:20]2[C:23](=O)[C:22](=[O:25])[C:21]=2[O:26]C)=[CH:17][CH:16]=[C:15]([F:28])[C:3]=1[C:4]([N:6]1[CH2:10][CH2:9][CH2:8][C@H:7]1[C:11]([O:13][CH3:14])=[O:12])=[O:5].[CH3:29][C:30]1[O:34][C:33]([CH:35]([NH2:41])[C:36]2([CH3:40])[CH2:39][O:38][CH2:37]2)=[CH:32][CH:31]=1>CO>[F:1][C:2]1[C:18]([NH:19][C:20]2[C:21](=[O:26])[C:22](=[O:25])[C:23]=2[NH:41][CH:35]([C:33]2[O:34][C:30]([CH3:29])=[CH:31][CH:32]=2)[C:36]2([CH3:40])[CH2:37][O:38][CH2:39]2)=[CH:17][CH:16]=[C:15]([F:28])[C:3]=1[C:4]([N:6]1[CH2:10][CH2:9][CH2:8][C@H:7]1[C:11]([O:13][CH3:14])=[O:12])=[O:5]

Participants

4

Reactant 2

HCID 89525357C-(5-methylfuran-2-yl)-C-(3-methyloxetan-3-yl)methylamineHCID 89534509HCID 89534509, compound

Product 1

HCID 71525973HCID 71525973, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 500 mg (1.27 mmol) of methyl (S)-1-[2,6-difluoro-3-(2-methoxy-3,4-dioxocyclobut-1-enylamino)benzoyl]-pyrrolidine-2-carboxylate and 344 mg (1.90 mmol, 1.5 eq) of C-(5-methylfuran-2-yl)-C-(3-methyloxetan-3-yl)methylamine in 25 ml of methanol was heated at 60° C. and was then stirred at ambient temperature overnight. The reaction medium was concentrated. The residue was taken up with 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. 0.64 g of methyl (S)-1-[2,6-difluoro-3-(2-{[(5-methylfuran-2-yl)-(3-methyloxetan-3-yl)methyl]amino}-3,4-dioxocyclobut-1-enylamino)benzoyl]pyrrolidine-2-carboxylate was obtained. Yield=93%, Mp=122° 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-d5db4ab54bf4460fbeb8cb9c8eef650b
Source dataset
uspto-grants-2015_07
Patent number
US09090596B2

Reaction notes

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