HCID 59568679, compound → HCID 59568718, compound

HRID 1474385Notes

Reaction equation

HRID 1474385 reaction equation
Br[CH2:2][C:3]([C:5]1[C:14]([CH3:15])=[CH:13][C:8]2[C:9](=[O:12])[O:10][CH2:11][C:7]=2[C:6]=1[CH3:16])=[O:4].[Cl-].[OH:18][C@H:19]([C:27]1[CH:36]=[CH:35][C:30]2[C:31](=[O:34])[O:32][CH2:33][C:29]=2[C:28]=1[CH3:37])[CH2:20][NH+:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>C1COCC1>[OH:18][C@H:19]([C:27]1[CH:36]=[CH:35][C:30]2[C:31](=[O:34])[O:32][CH2:33][C:29]=2[C:28]=1[CH3:37])[CH2:20][N:21]1[CH2:26][CH2:25][N:24]([CH2:2][C:3]([C:5]2[C:14]([CH3:15])=[CH:13][C:8]3[C:9](=[O:12])[O:10][CH2:11][C:7]=3[C:6]=2[CH3:16])=[O:4])[CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 59568679HCID 59568679, compoundHCID 68432653HCID 68432653, compound

Product 1

HCID 59568718HCID 59568718, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a 5 ml microwave tube were added 5-(bromoacetyl)-4,6-dimethyl-2-benzofuran-1(3H)-one (0.220 g, 0.777 mmol), 1-[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-ium chloride (0.215 g, 0.777 mmol), and a stir bar; the mixture was dissolved in THF (2 mL). The tube was capped, degassed and purged with N2. The tube was then placed in an oil bath and heated at 50° C. for 12 h; LC indicated formation of the desired product. The solution was concentrated to dryness, dissolved in MeOH (3.6 mL), filtered and was then subjected to purification by mass-directed HPLC to give 5-({4-[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}acetyl)-4,6-dimethyl-2-benzofuran-1(3H)-one. LC-MS (IE, m/z): 479 [M+1]+.

Workup

  1. customThe tube was capped
  2. customdegassed
  3. custompurged with N2
  4. customThe tube was then placed in an oil bath
  5. concentrationThe solution was concentrated to dryness
  6. dissolutiondissolved in MeOH (3.6 mL)
  7. filtrationfiltered
  8. customwas then subjected to purification by mass-directed HPLC

Sources & evidence

ORD record
ord-6641be9d86714905ae56ae63a370ea90
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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