Citric Acid → HCID 68359760, compound

HRID 2075292Notes

Reaction equation

HRID 2075292 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6]([C:8]1[C:17]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:16]2[C:11]([CH:12]=[C:13]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[CH:14]=[N:15]2)=[C:10](I)[N:9]=1)=[O:7].[CH3:35][O:36][CH2:37]/[CH:38]=[CH:39]/B1OC(C)(C)C(C)(C)O1.C(=O)([O-])[O-].[K+].[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O.C(OCC)(=O)C.CN(C)C=O>[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6]([C:8]1[C:17]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:16]2[C:11]([CH:12]=[C:13]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[CH:14]=[N:15]2)=[C:10]([CH:39]=[CH:38][CH2:37][O:36][CH3:35])[N:9]=1)=[O:7]

Participants

8

Reactant 4

HCID 311Citric AcidHCID 11430Potassium CarbonateHCID 162174432-[(1E)-3-methoxyprop-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 59696213HCID 59696213, compound

Product 1

HCID 68359760HCID 68359760, compoundYield 52.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To Compound 10 (286 mg, 0.5 mmol) and tetrakistriphenyl phosphine palladium (30 mg, 0.026 mmol) was added a dimethylformamide (4 ml) solution of 2-((E)-3-methoxy-propenyl)-4,4,5,5-tetramethyl[1,3,2]dioxaborolane (142 mg, 0.65 mmol), followed by an aqueous solution of 2 moles of potassium carbonate (0.66 ml, 1.32 mmol), and after vacuum deaeration under stirring at room temperature, and replacement with nitrogen, the reaction was heated under stirring in an oil bath at 100° C. After 3 hours, to the reaction mixture were added and dissolved ethyl acetate and water, and was added 10% citric acid (8 ml), and then the mixture was shaken for separation, washed twice with water, dried over sodium sulfate, and subjected to distillation under reduced pressure. The residue was subjected to high flash column chromatography (toluene:acetone (4:1)), and the obtained residue (170 mg) was crystallized from diisopropyl ether, to give 8-benzyloxy-3-(4-fluorobenzyl)-5-(3-methoxypropenyl)[1,6]naphthyridine-7-carboxylic acid (2-methoxyethyl)amide b-11 (135 mg) in 52.3% yield.

Workup

  1. temperaturereplacement with nitrogen, the reaction was heated
  2. stirringunder stirring in an oil bath at 100° C
  3. additionto the reaction mixture were added
  4. stirringthe mixture was shaken for separation
  5. washwashed twice with water
  6. dry with materialdried over sodium sulfate
  7. distillationsubjected to distillation under reduced pressure
  8. customthe obtained residue (170 mg) was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-81ff5db133b24e618667d3f3e6a16650
Source dataset
uspto-grants-2011_04
Patent number
US07919623B2

Reaction notes

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