Potassium Carbonate → HCID 86640099, compound

HRID 555349Notes

Reaction equation

HRID 555349 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9](=[O:33])/[C:10](/[CH2:21][O:22][C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=[CH:25][CH:24]=2)=[CH:11]/[C:12]2[CH:20]=[CH:19][C:15]([C:16](O)=[O:17])=[CH:14][CH:13]=2)[CH2:4][CH2:3]1.Cl.C(N=C=NCCCN(C)C)C.[O:46]1[CH2:51][CH2:50][CH2:49][CH2:48][CH:47]1[O:52][NH2:53].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(N(CC)CC)C>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9](=[O:33])/[C:10](/[CH2:21][O:22][C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=[CH:25][CH:24]=2)=[CH:11]/[C:12]2[CH:13]=[CH:14][C:15]([C:16]([NH:53][O:52][CH:47]3[CH2:48][CH2:49][CH2:50][CH2:51][O:46]3)=[O:17])=[CH:19][CH:20]=2)[CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 66986854HCID 66986854, compound

Product 1

HCID 86640099HCID 86640099, compoundYield 80.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

(E)-4-(3-(1-Methylpiperidin-4-ylamino)-2-((naphthalen-1-yloxy)-methyl)-3-oxo-prop-1-enyl)benzoic acid (339 mg, 0.56 mM) obtained in Example (1-1-2) was dissolved in dimethylformamide (4 ml) and cooled to 0° C. To the resulting mixture, triethylamine (0.16 ml, 1.14 mM), N-hydroxy-6-trifluorobenzotriazole (FOBt; 171 mg, 0.84 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide.hydrochloride (EDC.HCl; 190 mg, 0.99 mmol) and tetrahydro-2H-pyran-2-yloxyamine (THPONH2; 107 mg, 0.91 mmol) were added at 0° C. and the resulting mixture was stirred at room temperature for 12 hrs. To the mixture, 10% potassium carbonate solution (20 ml) was added thereto. Then, the resultant was extracted with ethyl acetate (20 ml, 15 ml×2). The organic layer was separated, washed with brine (20 ml) and dried over anhydrous sodium sulfate, followed by removing the solvent under reduced pressure. The residue thus obtained was subjected to a silica gel column chromatography to obtain 333 mg of the title compound as a white solid (yield 80%).

Workup

  1. extractionThen, the resultant was extracted with ethyl acetate (20 ml, 15 ml×2)
  2. customThe organic layer was separated
  3. washwashed with brine (20 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customby removing the solvent under reduced pressure
  6. customThe residue thus obtained

Sources & evidence

ORD record
ord-ba4cfdde3f2345bfaeaddf72ae19de72
Source dataset
uspto-grants-2011_11
Patent number
US08053435B2

Reaction notes

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