4,5,6,7-Tetrahydro-4,7-ethano-2-benzofuran-1,3-dione → HCID 73442651, compound

HRID 530685Notes

Reaction equation

HRID 530685 reaction equation
[NH2:1][C:2]1[S:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[C:4]([CH3:11])[C:3]=1[C:12]1[S:13][CH:14]=[C:15]([CH3:17])[N:16]=1.[CH:18]12[CH2:25][CH2:24][CH:21]([CH2:22][CH2:23]1)[C:20]1[C:26]([O:28][C:29](=[O:30])[C:19]2=1)=[O:27]>CC#N.CN(C1C=CN=CC=1)C>[CH3:10][O:9][C:7]([C:5]1[S:6][C:2]([NH:1][C:29]([C:19]2[CH:18]3[CH2:25][CH2:24][CH:21]([C:20]=2[C:26]([OH:28])=[O:27])[CH2:22][CH2:23]3)=[O:30])=[C:3]([C:12]2[S:13][CH:14]=[C:15]([CH3:17])[N:16]=2)[C:4]=1[CH3:11])=[O:8]

Participants

5

Reactant 2

HCID 149673334,5,6,7-Tetrahydro-4,7-ethano-2-benzofuran-1,3-dioneHCID 90046339HCID 90046339, compound

Product 1

HCID 73442651HCID 73442651, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

To the solution of methyl 5-amino-3-methyl-4-(4-methylthiazol-2-yl)thiophene-2-carboxylate (61 mg, 227 μmol, Int1.2) in CH3CN (7 mL) were added DMAP (55.5 mg, 455 μmol) and bicyclo[2.2.2]oct-2-ene-2,3-dicarboxylic anhydride (40.5 mg, 227 μmol, CAS RN 151813-29-5). After stirring at RT for 3 h, the reaction mixture was stirred at 65° C. overnight. The reaction mixture was extracted with EtOAc and 1M aqueous HCl, the organic layer was dried over Na2SO4, filtered and evaporated. The compound was purified by silica gel chromatography using a mixture of CH2Cl2:MeOH (20:1 v/v) as eluant. Brown solid. MS (ESI): m/z=447.1 [M+H]+.

Workup

  1. stirringthe reaction mixture was stirred at 65° C. overnight
  2. extractionThe reaction mixture was extracted with EtOAc and 1M aqueous HCl
  3. dry with materialthe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe compound was purified by silica gel chromatography
  7. additiona mixture of CH2Cl2:MeOH (20:1 v/v) as eluant

Sources & evidence

ORD record
ord-bd04a03624144fba92ccf870f21a9e83
Source dataset
uspto-grants-2016_05
Patent number
US09353102B2

Reaction notes

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