C-(5-methylfuran-2-yl)-C-(3-methyloxetan-3-yl)methylamine → HCID 71525794, compound

HRID 1528201Notes

Reaction equation

HRID 1528201 reaction equation
[CH3:1][C:2]1[O:6][C:5]([CH:7]([NH2:13])[C:8]2([CH3:12])[CH2:11][O:10][CH2:9]2)=[CH:4][CH:3]=1.C([O:16][C:17]1[C:18](=[O:33])[C:19](=O)[C:20]=1[NH:21][C:22]1[C:30]2[NH:29][C:28](=[O:31])[NH:27][C:26]=2[CH:25]=[CH:24][CH:23]=1)C>>[CH3:1][C:2]1[O:6][C:5]([CH:7]([NH:13][C:19]2[C:18](=[O:33])[C:17](=[O:16])[C:20]=2[NH:21][C:22]2[C:30]3[NH:29][C:28](=[O:31])[NH:27][C:26]=3[CH:25]=[CH:24][CH:23]=2)[C:8]2([CH3:12])[CH2:9][O:10][CH2:11]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 89525357C-(5-methylfuran-2-yl)-C-(3-methyloxetan-3-yl)methylamineHCID 89526128HCID 89526128, compound

Product 1

HCID 71525794HCID 71525794, compoundYield 18%

Conditions

Temperature
65 °C

Procedure

0.33 g of C-(5-methylfuran-2-yl)-C-(3-methyloxetan-3-yl)methylamine (1.80 mmol, 1.2 eq) was added to a solution of 0.41 g of 3-ethoxy-4-(2-oxo-2,3-dihydro-1H-benzoimidazol-4-ylamino)cyclobut-3-ene-1,2-dione (1.50 mmol, 1 eq). The reaction medium was heated at 65° C. for 18 hours. The methanol was evaporated off and the residue was chromatographed on silica gel, eluent 95/5 dichloromethane/methanol with 0.1% of triethylamine. The product remains stuck on the silica. The paste obtained was crystallized from diethyl ether, filtered and dried under vacuum at 40° C. 0.11 g of 3-{[(5-methylfuran-2-yl)-(3-methyloxetan-3-yl)methyl]amino}-4-(2-oxo-2,3-dihydro-1H-benzoimidazol-4-ylamino)cyclobut-3-ene-1,2-dione was obtained. Yield=18%. HPLC 94.8%, ES− [407].

Workup

  1. customThe methanol was evaporated off
  2. customthe residue was chromatographed on silica gel, eluent 95/5 dichloromethane/methanol with 0.1% of triethylamine
  3. customThe paste obtained
  4. customwas crystallized from diethyl ether
  5. filtrationfiltered
  6. customdried under vacuum at 40° C

Sources & evidence

ORD record
ord-cb5c058579004792a21f3a657c425917
Source dataset
uspto-grants-2015_07
Patent number
US09090596B2

Reaction notes

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