Hydrochloric Acid → HCID 178493385, compound

HRID 1056824Notes

Reaction equation

HRID 1056824 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:6]=[CH:5][C:4]=1[CH:17]=[CH:18][C:19](=[O:24])[CH2:20][C:21](=[O:23])[CH3:22].[B]=O.[NH:27]1[C:31]2[CH:32]=[CH:33][C:34]([CH:36]=O)=[CH:35][C:30]=2[N:29]=[N:28]1.B(OC(C)C)(OC(C)C)OC(C)C.N1CCCCC1.Cl.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.[Cl-].[Na+].O>[NH:27]1[C:31]2[CH:32]=[CH:33][C:34](/[CH:36]=[CH:22]/[C:21](=[O:23])[CH2:20][C:19](=[O:24])/[CH:18]=[CH:17]/[C:4]3[CH:5]=[CH:6][C:7]([O:9][CH2:10][C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=4)=[CH:8][C:3]=3[O:2][CH3:1])=[CH:35][C:30]=2[N:29]=[N:28]1

Participants

10

Reactant 7

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 21531Triisopropyl borateHCID 516892Sodium BicarbonateHCID 6327189Boron monoxideHCID 86713227HCID 86713227, compoundHCID 178519382HCID 178519382, compound

Product 1

HCID 178493385HCID 178493385, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent2×HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
70 °C

Procedure

In a 20 mL reaction vessel were placed 44.3 mg (136 μmol) of 6-[2-methoxy-4-(2-pyridylmethoxy)phenyl]hex-5-ene-2,4-dione and 13.2 mg (0.190 mmol) of boron oxide and they were dissolved in 0.88 mL of ethyl acetate. To the mixture under stirring at 70° C., 20 mg (0.14 mmol) of 1H-benzotriazole-5-carboxaldehyde and 62 μL (0.27 mmol) of triisopropyl borate were sequentially added. After the mixture was stirred at the same temperature for 1 hour, a solution of 2.7 μL (27 μmol) of piperidine in ethyl acetate (0.135 mL) was added and the mixture was further stirred for 1 hour. To the reaction mixture was added a 1:1 solution (0.4 mL) of 1 N hydrochloric acid and saturated brine at room temperature and the mixture was stirred for 5 minutes to 1 hour (further, the mixture was neutralized with a saturated sodium bicarbonate aqueous solution as needed). The resulting organic phase was directly subjected to purification by silica gel column chromatography (hexane/ethyl acetate or methylene chloride/methanol) to give 5.9 mg (10% yield) of the title compound as an orange powder.

Workup

  1. customIn a 20 mL reaction vessel
  2. stirringAfter the mixture was stirred at the same temperature for 1 hour
  3. stirringthe mixture was further stirred for 1 hour
  4. stirringthe mixture was stirred for 5 minutes to 1 hour (further, the mixture
  5. customThe resulting organic phase was directly subjected to purification by silica gel column chromatography (hexane/ethyl acetate or methylene chloride/methanol)

Sources & evidence

ORD record
ord-2fc6feadd2314604bac2d9fbee78835e
Source dataset
uspto-grants-2016_07
Patent number
US09399635B2

Reaction notes

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