Trimethylamine → HCID 71478170, compound

HRID 527167Notes

Reaction equation

HRID 527167 reaction equation
[OH:1][C:2]12[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14](=[O:21])[C:3]1([NH:22][C:23](=[O:25])[CH3:24])[C:4]1[C:9]([O:10]2)=[CH:8][C:7]([CH:11]([CH3:13])[CH3:12])=[CH:6][CH:5]=1.[CH3:26][N:27]([CH3:29])[CH3:28].C1C[O:33]CC1>>[C:23]([NH:22][C:3]1([C:4]2[CH:5]=[CH:6][C:7]([CH:11]([CH3:12])[CH3:13])=[CH:8][C:9]=2[O:10][C:26](=[O:33])[N:27]([CH3:29])[CH3:28])[C:14](=[O:21])[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:2]1=[O:1])(=[O:25])[CH3:24]

Participants

4

Reactant 3

HCID 1146TrimethylamineHCID 8028TetrahydrofuranHCID 86716885HCID 86716885, compound

Product 1

HCID 71478170HCID 71478170, compoundYield 43%

Procedure

N-(4b-hydroxy-7-isopropyl-10-oxo-4b,10-dihydro-5-oxa-indeno[2,1-a]inden-9b-yl)-acetamide (0.50 g, 1.48 mmol) was dissolved in anhydrous THF (15 ml). This solution was added with Dimethyl-carbamylchrolide (0.23 g, 2.22 mmol), Trimethylamine (0.17 g, 1.77 mmol). The reaction mixture was heated for 24 hrs under reflux. After concentrating in a vacuum to remove THF, and the remainder was diluted with Ethylacetate and washed with Bicarbonate sodium aqueous solution many times. After drying and filtrating, the organic layer was purified using column chromatography (ethylacetate:hexane=1:1) to afford the title compound (0.26 g, 43%).

Workup

  1. temperatureThe reaction mixture was heated for 24 hrs
  2. temperatureunder reflux
  3. concentrationAfter concentrating in a vacuum
  4. customto remove THF
  5. additionthe remainder was diluted with Ethylacetate
  6. washwashed with Bicarbonate sodium aqueous solution many times
  7. customAfter drying
  8. filtrationfiltrating
  9. customthe organic layer was purified

Sources & evidence

ORD record
ord-5d807be4572a47cd8783d43be961656a
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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