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

HRID 2401285ノート

反応式

HRID 2401285 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.[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 1140Toluene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 (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).

後処理

  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)

出典と根拠

ORDレコード
ord-cc904d5e71694f9a8b1a854bdbd9293a
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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