Ethanolamine → HCID 117701715, compound

HRID 1507451Notes

Reaction equation

HRID 1507451 reaction equation
[CH2:1]([O:8][C:9]1[C:18]([C:19]([OH:21])=O)=[C:17]2[C:12]([C:13](=[O:33])[C:14]([CH3:32])=[C:15]([CH:22]3[CH2:27][CH2:26][N:25]([C:28](=[O:31])[CH2:29][CH3:30])[CH2:24][CH2:23]3)[O:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.C(N(CC)CC)C.[NH2:45][CH2:46][CH2:47][OH:48]>ClCCl.O.CN(C)C=O>[CH2:1]([O:8][C:9]1[C:18]([C:19]([NH:45][CH2:46][CH2:47][OH:48])=[O:21])=[C:17]2[C:12]([C:13](=[O:33])[C:14]([CH3:32])=[C:15]([CH:22]3[CH2:27][CH2:26][N:25]([C:28](=[O:31])[CH2:29][CH3:30])[CH2:24][CH2:23]3)[O:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 700EthanolamineHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 117701563HCID 117701563, compound

Product 1

HCID 117701715HCID 117701715, compoundYield 66.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-(benzyloxy)-3-methyl-4-oxo-2-(1-propanoylpiperidin-4-yl)-4H-chromene-8-carboxylic acid (200 mg, 0.44 mmol) obtained in Example 35-1 in dichloromethane (4 mL), thionyl chloride (97 μL, 1.33 mmol) was added dropwise under cooling with ice. Then, a catalytic amount of dimethylformamide was added dropwise thereto, and the mixture was brought back to room temperature and stirred for 15 hours. The reaction solution was concentrated under reduced pressure, and then the residue was subjected to azeotropy with toluene (2 mL). Dichloromethane (4 mL) was added to the obtained residue. Triethylamine (93 μL, 0.67 mmol) and 2-aminoethanol (53 μL, 0.89 mmol) were added dropwise thereto under cooling with ice, and then the mixture was brought back to room temperature and stirred for 8 hours. Water was added to the reaction solution, followed by extraction with dichloromethane. Then, the organic layer was dried over sodium sulfate. The desiccant was filtered off, and then the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform/methanol=100/0→95/5) to obtain 144 mg of the title compound (yield: 66%).

Workup

  1. temperatureunder cooling with ice
  2. customwas brought back to room temperature
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. additionDichloromethane (4 mL) was added to the obtained residue
  5. temperatureunder cooling with ice
  6. customwas brought back to room temperature
  7. stirringstirred for 8 hours
  8. extractionfollowed by extraction with dichloromethane
  9. dry with materialThen, the organic layer was dried over sodium sulfate
  10. filtrationThe desiccant was filtered off
  11. concentrationthe filtrate was concentrated under reduced pressure
  12. customThe obtained residue was purified by silica gel column chromatography (chloroform/methanol=100/0→95/5)

Sources & evidence

ORD record
ord-f6579ec23827491fa5b0f45aa17088a6
Source dataset
uspto-grants-2015_12
Patent number
US09221811B2

Reaction notes

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