Potassium Carbonate → HCID 66818499, compound

HRID 1024690Notes

Reaction equation

HRID 1024690 reaction equation
C([O-])([O-])=O.[K+].[K+].C(N(CC)C(C)C)(C)C.[C:16]([O:20][C:21](=[O:27])[NH:22][CH2:23][CH2:24][CH2:25]Br)([CH3:19])([CH3:18])[CH3:17].[C:28]([C:30]1[CH:60]=[CH:59][C:33]([O:34][C:35]2[N:49]=[C:48]([O:50][C:51]3[CH:56]=[CH:55][C:54]([C:57]#[N:58])=[CH:53][CH:52]=3)[CH:47]=[CH:46][C:36]=2[C:37]([NH:39][CH:40]2[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]2)=[O:38])=[CH:32][CH:31]=1)#[N:29]>CN(C=O)C>[C:16]([O:20][C:21](=[O:27])[NH:22][CH2:23][CH2:24][CH2:25][N:43]1[CH2:44][CH2:45][CH:40]([NH:39][C:37]([C:36]2[C:35]([O:34][C:33]3[CH:32]=[CH:31][C:30]([C:28]#[N:29])=[CH:60][CH:59]=3)=[N:49][C:48]([O:50][C:51]3[CH:56]=[CH:55][C:54]([C:57]#[N:58])=[CH:53][CH:52]=3)=[CH:47][CH:46]=2)=[O:38])[CH2:41][CH2:42]1)([CH3:19])([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 4460490tert-butyl N-(3-bromopropyl)carbamateHCID 66818735HCID 66818735, compound

Product 1

HCID 66818499HCID 66818499, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
45 °C

Procedure

0.117 g (0.85 mmol) of K2CO3 and N,N-diisopropylethylamine 0.072 g (0.56 mmol) followed by 0.201 g (0.85 mmol) of (3-bromo-propyl)-carbamic acid tert-butyl ester, dissolved in 5 ml of DMF, were added to a stirred solution of 0.373 g (0.85 mmol) of 2,6-bis-(4-cyano phenoxy)-N-piperidine-4-yl nicotinamide, dissolved in 5 ml of DMF over a period of 15 min at 20° C. Reaction mixture was allowed to attain RT and heated to 45° C. for 2 h. The reaction mixture was concentrated under reduced pressure to remove the solvent. The residue was partitioned between water (150 ml) and ethyl acetate (150 ml). The organic phase was washed with 1 M Na2CO3 and saturated brine solution, and dried over sodium sulphate. The solution was concentrated and the oily residue was purified by column chromatography using hexane-ethyl acetate (10:2) to afford 0.45 g of the required product. Percentage purity (LCMS): 72.5%, (M+1)=596.2+1.

Workup

  1. customReaction mixture
  2. customto attain RT
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customto remove the solvent
  5. customThe residue was partitioned between water (150 ml) and ethyl acetate (150 ml)
  6. washThe organic phase was washed with 1 M Na2CO3 and saturated brine solution
  7. dry with materialdried over sodium sulphate
  8. concentrationThe solution was concentrated
  9. customthe oily residue was purified by column chromatography

Sources & evidence

ORD record
ord-4f3070a833954303bd767c06683b71df
Source dataset
uspto-grants-2014_05
Patent number
US08722930B2

Reaction notes

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