N,N,N',N'-Tetramethylethylenediamine → 2-[(5S)-3-(6-Cyanopyridin-3-yl)-2-oxo-5-(propan-2-yl)imidazolidin-1-yl]-N-[3-(trifluoromethyl)phenyl]acetamide

HRID 2401284Notes

Reaction equation

HRID 2401284 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.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[CH3:73][N:74](C)CCN(C)C>CN(C=O)C.[C-]#N.[Zn+2].[C-]#N.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]>[C:73]([C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:12][C@H:11]([CH:13]([CH3:14])[CH3:15])[N:10]([CH2:16][C:17]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:27])([F:29])[F:28])[CH:21]=3)=[O:18])[C:9]2=[O:30])=[CH:4][CH:3]=1)#[N:74]

Participants

7

Reactant 3

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86705191HCID 86705191, compound

Product 1

HCID 867051902-[(5S)-3-(6-Cyanopyridin-3-yl)-2-oxo-5-(propan-2-yl)imidazolidin-1-yl]-N-[3-(trifluoromethyl)phenyl]acetamide

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst2×HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent

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 (150 mg), zinc cyanide (91 mg), Pd2(dba)3 (8.5 mg), Xantphos (11 mg), and N,N,N′,N′-tetramethylethylenediamine (14 μL) in DMF (2 mL) was stirred under irradiation with microwave at 180° C. for 30 min. Additional zinc cyanide (91 mg) was added thereto, and the resulting mixture was stirred under the same condition for 30 min. NH silica gel was added thereto, the mixture was stirred, followed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by preparative HPLC to afford the title compound (47 mg).

Workup

  1. additionNH silica gel was added
  2. stirringthe mixture was stirred
  3. filtrationfollowed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-6f2612134ae34eff86681ce0d3c70f23
Source dataset
uspto-grants-2014_08
Patent number
US08796272B2

Reaction notes

Loading…