Diisopropylethylamine → HCID 67243364, compound

HRID 2421922Notes

Reaction equation

HRID 2421922 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[C:7]1=[O:14].[C:15]([C:19]1[N:24]=[C:23]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:22]=[C:21]([CH2:31][CH2:32][CH3:33])[N:20]=1)([CH3:18])([CH3:17])[CH3:16].[Br-].[Na+].C(N(C(C)C)C(C)C)C.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.O.CN1CCCC1=O>[C:15]([C:19]1[N:24]=[C:23]([N:25]2[CH2:30][CH2:29][N:28]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]3[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[C:7]3=[O:14])[CH2:27][CH2:26]2)[CH:22]=[C:21]([CH2:31][CH2:32][CH3:33])[N:20]=1)([CH3:18])([CH3:17])[CH3:16]

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 253881Sodium BromideHCID 516892Sodium BicarbonateHCID 22349857HCID 22349857, compoundHCID 592346471-(4-Chlorobutyl)-3-methoxy-1H-pyridin-2-one

Product 1

HCID 67243364HCID 67243364, compoundYield 58.4%

Reagents, catalysts & solvents 2

HCID 13387N-methyl-2-pyrrolidoneSolventHCID 22728543Water ethylacetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1-(4-chlorobutyl)-3-methoxy-1H-pyridin-2-one (0.93 mmol, 0.20 g) from Example 5.1, 2-tert-butyl-4-piperazin-1-yl-6-propylpyrimidine (0.93 mmol, 0.24 g; prepared as described in DE 19735410), sodium bromide (4.64 mmol, 0.48 g), ethyldiisopropylamine (9.09 mmol, 1.17 g) and N-methylpyrrolidinone (0.5 ml) was heated at 120° C. for 6 hours. The resulting suspension was filtered with suction and the filtrate was concentrated. The residue obtained in this way was taken up in ethyl acetate/water. The aqueous mixture was adjusted to pH 5.5 with sodium bicarbonate and the aqueous mixture was extracted several times with diethyl ether. The organic phase was then dried, the desiccant was removed by filtration, and the organic phase was concentrated under reduced pressure. Chromatography of the residue on silica gel (eluent: CH2Cl2/CH3OH (0-2%) afforded 0.24 g of the title compound.

Workup

  1. filtrationThe resulting suspension was filtered with suction
  2. concentrationthe filtrate was concentrated
  3. customThe residue obtained in this way
  4. extractionthe aqueous mixture was extracted several times with diethyl ether
  5. customThe organic phase was then dried
  6. customthe desiccant was removed by filtration
  7. concentrationthe organic phase was concentrated under reduced pressure

Sources & evidence

ORD record
ord-52763a820e1b4e8d83697f49536ce0a7
Source dataset
uspto-grants-2011_06
Patent number
US07960386B2

Reaction notes

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