Sodium Iodide → HCID 117840179, compound

HRID 1477733Notes

Reaction equation

HRID 1477733 reaction equation
[CH3:1][C:2]1[N:7]([CH2:8][C:9]2[S:10][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:13]=2)[C:6](=[O:18])[N:5]=[C:4]([N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[N:3]=1.[C:25]12([C:35](=[O:38])[CH2:36]Br)[CH2:34][CH:29]3[CH2:30][CH:31]([CH2:33][CH:27]([CH2:28]3)[CH2:26]1)[CH2:32]2.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].C(=O)(O)[O-].[Na+]>C(#N)C>[C:25]12([C:35](=[O:38])[CH2:36][N:22]3[CH2:23][CH2:24][N:19]([C:4]4[N:3]=[C:2]([CH3:1])[N:7]([CH2:8][C:9]5[S:10][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:13]=5)[C:6](=[O:18])[N:5]=4)[CH2:20][CH2:21]3)[CH2:32][CH:31]3[CH2:30][CH:29]([CH2:28][CH:27]([CH2:33]3)[CH2:26]1)[CH2:34]2

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 197820Bromomethyl tricyclo[3.3.1.13,7]dec-1-yl ketoneHCID 516892Sodium BicarbonateHCID 117839606HCID 117839606, compound

Product 1

HCID 117840179HCID 117840179, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To an acetonitrile solution (4.0 mL) of 6-methyl-4-(piperazin-1-yl)-1-{[5-(trifluoromethyl)thiophen-2-yl]methyl}-1,3,5-triazin-2(1H)-one (28.7 mg, 80.0 μmol) synthesized in Reference Synthesis Example 351, 1-(adamantan-1-yl)-2-bromoethanone (23.1 mg, 90.0 μmol), potassium carbonate (13.8 mg, 100 μmol), and sodium iodide (15.0 mg, 100 μmol) were added and the resultant mixture was stirred at room temperature for 1 day. After the completion of the reaction, to the reaction solution, saturated sodium bicarbonate aqueous solution was added and extraction with ethyl acetate from the reaction solution was performed. The organic layer was concentrated under reduced pressure and the resultant residue was purified by silica gel column chromatography (chloroform/methanol=10/0→9/1) to obtain the title compound (20.8 mg, yield: 49%).

Workup

  1. additionwere added
  2. customAfter the completion of the reaction
  3. extractionextraction with ethyl acetate from the reaction solution
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customthe resultant residue was purified by silica gel column chromatography (chloroform/methanol=10/0→9/1)

Sources & evidence

ORD record
ord-19bd21bf6f6d4ec58f6fb216287763ee
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

Loading…