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 2401284ノート

反応式

HRID 2401284 の反応式
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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 11186Zinc cyanide (Zn(CN)2)触媒2 回HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6f2612134ae34eff86681ce0d3c70f23
出典データセット
uspto-grants-2014_08
特許番号
US08796272B2

反応ノート

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