Potassium Carbonate → HCID 178443482, compound

HRID 1947267Notes

Reaction equation

HRID 1947267 reaction equation
Cl.Cl.[CH:3]1([NH:9][C:10]2[C:14]3([CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[N:13]([C:20]3[CH:25]=[CH:24][C:23]([I:26])=[CH:22][CH:21]=3)[C:12](=[O:27])[N:11]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.C(N(C(C)C)CC)(C)C.C(=O)([O-])[O-].[K+].[K+].I[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH:51]=[CH2:52]>CN(C=O)C.C(OCC)(=O)C>[CH:3]1([NH:9][C:10]2[C:14]3([CH2:15][CH2:16][N:17]([CH2:52][CH2:51][CH2:50][CH2:49][CH2:48][CH2:47][CH2:46][CH:45]=[CH2:44])[CH2:18][CH2:19]3)[N:13]([C:20]3[CH:21]=[CH:22][C:23]([I:26])=[CH:24][CH:25]=3)[C:12](=[O:27])[N:11]=2)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 22499309HCID 22499309, compoundHCID 178478873HCID 178478873, compound

Product 1

HCID 178443482HCID 178443482, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(cyclohexylamino)-1-(4-iodophenyl)-1,3,8-triazaspiro[4.5]dec-3-en-2-one dihydrochloride (400 mg, 0.76 mmol, intermediate II.1.c.1) in DMF (6 mL) was added diisopropylethylamine (0.333 mL, 1.9 mmol) and the reaction mixture was stirred at rt for 10 min. Potassium carbonate (210 mg, 1.52 mmol) and 9-iodononene (230 mg, 0.91 mmol, prepared from 9-hydroxynonene, iodine, triphenylphosphine and imidazole) were added. The reaction mixture was stirred at 100° C., sealed, for 1 h. The reaction mixture was diluted with ethyl acetate, washed with water. The organic layer was concentrated in vacuo and the residue was purified by reverse phase preparative HPLC (5- 95% MeCN/H2O containing 0.1% TFA, C18). The desired fractions were basified with aqueous NaHCO3, extracted with EtOAc, washed with brine, dried over sodium sulfate and concentrated in vacuo to provide the desired compound as a light brown solid. LRMS (M+1)=577.

Workup

  1. stirringThe reaction mixture was stirred at 100° C.
  2. customsealed, for 1 h
  3. washwashed with water
  4. concentrationThe organic layer was concentrated in vacuo
  5. customthe residue was purified by reverse phase preparative HPLC (5- 95% MeCN/H2O containing 0.1% TFA
  6. extractionextracted with EtOAc
  7. washwashed with brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-da17767dbcbe4bc3bc8e7e8180a323bd
Source dataset
uspto-grants-2013_03
Patent number
US08399473B2

Reaction notes

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