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

HRID 2401285노트

반응식

HRID 2401285 반응식
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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 1140Toluene용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-cc904d5e71694f9a8b1a854bdbd9293a
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08796272B2

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