4-methyl-5-(oxiran-2-yl)isobenzofuran-1(3H)-one → 6-({4-[2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}methyl)-1,6,7,8-tetrahydro-3H-indeno[4,5-c]furan-3-one

HRID 1187110Notes

Reaction equation

HRID 1187110 reaction equation
[N:1]1([CH2:7][CH:8]2[C:12]3[CH:13]=[CH:14][C:15]4[C:19](=[O:20])[O:18][CH2:17][C:16]=4[C:11]=3[CH2:10][CH2:9]2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH3:21][C:22]1[C:30]2[CH2:29][O:28][C:27](=[O:31])[C:26]=2[CH:25]=[CH:24][C:23]=1[CH:32]1[CH2:34][O:33]1>CCO>[OH:33][CH:32]([C:23]1[CH:24]=[CH:25][C:26]2[C:27](=[O:31])[O:28][CH2:29][C:30]=2[C:22]=1[CH3:21])[CH2:34][N:4]1[CH2:5][CH2:6][N:1]([CH2:7][CH:8]2[C:12]3[CH:13]=[CH:14][C:15]4[C:19](=[O:20])[O:18][CH2:17][C:16]=4[C:11]=3[CH2:10][CH2:9]2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 552705554-methyl-5-(oxiran-2-yl)isobenzofuran-1(3H)-oneHCID 595686516-(Piperazin-1-ylmethyl)-1,6,7,8-tetrahydro-3H-indeno[4,5-c]furan-3-one

Product 1

HCID 498047756-({4-[2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}methyl)-1,6,7,8-tetrahydro-3H-indeno[4,5-c]furan-3-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

6-(Piperazin-1-ylmethyl)-1,6,7,8-tetrahydro-3H-indeno[4,5-c]furan-3-one (40 mg, 0.15 mmol) and 4-methyl-5-oxiran-2-yl-2-benzofuran-1(3H)-one (55 mg, 0.29 mmol), were added to a 5 mL microwave tube containing a stir bar; to the mixture was added EtOH (2.5 mL). The tube was capped, degassed and purged with N2. It was then placed in a microwave reactor and heated at 150° C. for 30 min; LC indicated formation of the desired product. The solution was concentrated to dryness, dissolved in MeOH (3.5 mL), filtered and was then subjected to purification by mass-directed HPLC to give 6-({4-[2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}methyl)-1,6,7,8-tetrahydro-3H-indeno[4,5-c]furan-3-one. LC-MS (IE, m/z): 463 [M+1]+.

Workup

  1. additioncontaining a stir bar
  2. customThe tube was capped
  3. customdegassed
  4. custompurged with N2
  5. customIt was then placed in a microwave reactor
  6. concentrationThe solution was concentrated to dryness
  7. dissolutiondissolved in MeOH (3.5 mL)
  8. filtrationfiltered
  9. customwas then subjected to purification by mass-directed HPLC

Sources & evidence

ORD record
ord-ce1b8504b51e45f4b3121e2ce471a935
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

Loading…