Dimethylamine → 2-[(5S)-3-[6-(Dimethylamino)pyridin-3-yl]-2-oxo-5-(propan-2-yl)imidazolidin-1-yl]-N-[3-(trifluoromethyl)phenyl]acetamide

HRID 2401285Notes

Reaction equation

HRID 2401285 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:12][C@H:11]([CH:13]([CH3:15])[CH3:14])[N:10]([CH2:16][C:17]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)=[O:18])[C:9]2=[O:30])=[CH:4][CH:3]=1.[CH3:31][NH:32][CH3:33].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[K+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[CH3:31][N:32]([CH3:33])[C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:12][C@H:11]([CH:13]([CH3:15])[CH3:14])[N:10]([CH2:16][C:17]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)=[O:18])[C:9]2=[O:30])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 674DimethylamineHCID 634876Binap, (A+-)-HCID 23665647Potassium tert-butoxideHCID 86705191HCID 86705191, compound

Product 1

HCID 867051922-[(5S)-3-[6-(Dimethylamino)pyridin-3-yl]-2-oxo-5-(propan-2-yl)imidazolidin-1-yl]-N-[3-(trifluoromethyl)phenyl]acetamide

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of 2-[(5S)-3-(6-bromopyridin-3-yl)-2-oxo-5-(propan-2-yl)imidazolidin-1-yl]-N-[3-(trifluoromethyl)phenyl]acetamide (250 mg) and dimethyl amine (2M solution in THF, 1.3 mL), Pd2(dba)3 (24 mg), BINAP (32 mg), and potassium tert-butoxide (87 mg) in toluene (5 mL) was stirred at 120° C. for 2 hr. Water was added thereto, the mixture was extracted with chloroform, and the organic layer was concentrated under reduced pressure. The residue was purified by preparative HPLC and PTLC (hexane/ethyl acetate=1:1) to afford the title compound (34 mg).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. concentrationthe organic layer was concentrated under reduced pressure
  3. customThe residue was purified by preparative HPLC and PTLC (hexane/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-cc904d5e71694f9a8b1a854bdbd9293a
Source dataset
uspto-grants-2014_08
Patent number
US08796272B2

Reaction notes

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