Bicarbonate Ion → HCID 49803891, compound

HRID 1187099Notes

Reaction equation

HRID 1187099 reaction equation
[O:1]=[C:2]1[C:14]2[C:5](=[C:6]3[C:11](=[CH:12][CH:13]=2)[CH:10]([CH2:15]OS(C2C=CC(C)=CC=2)(=O)=O)[O:9][CH2:8][CH2:7]3)[CH2:4][O:3]1.C(=O)(O)[O-].[Cl-].[OH:32][CH:33]([C:41]1[CH:50]=[CH:49][C:44]2[C:45](=[O:48])[O:46][CH2:47][C:43]=2[C:42]=1[CH3:51])[CH2:34][NH+:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1>C(#N)C>[OH:32][CH:33]([C:41]1[CH:50]=[CH:49][C:44]2[C:45](=[O:48])[O:46][CH2:47][C:43]=2[C:42]=1[CH3:51])[CH2:34][N:35]1[CH2:40][CH2:39][N:38]([CH2:15][CH:10]2[C:11]3[C:6](=[C:5]4[CH2:4][O:3][C:2](=[O:1])[C:14]4=[CH:13][CH:12]=3)[CH2:7][CH2:8][O:9]2)[CH2:37][CH2:36]1

Participants

5

Reactant 3

HCID 769Bicarbonate IonHCID 66647325HCID 66647325, compoundHCID 86647318HCID 86647318, compound

Product 1

HCID 49803891HCID 49803891, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

To a 5 mL microwave tube were added (3-oxo-3,6,8,9-tetrahydro-1H-furo[3,4-f]isochromen-6-yl)methyl-4-methylbenzenesulfonate (50 mg, 0.13 mmol), the free base generated by aqueous bicarbonate wash of 1-[2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-ium chloride (55 mg, 0.20 mmol), and a stir bar; the mixture was dissolved in acetonitrile (2.5 mL). The tube was capped, degassed and purged with N2. The tube was then placed in a microwave reactor and heated at 120° C. for 1 h; 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 mass-directed HPLC for purification to give 6-({4-[2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}methyl)-8,9-dihydro-1H-furo[3,4-f]isochromen-3(6H)-one, as a mixture of isomers which could be partially separated under the purification conditions. LC-MS (IE, m/z): 478 [M+1]+.

Workup

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

Sources & evidence

ORD record
ord-2bf7b3ec90de499f98021f15e2895bb0
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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