Triethylamine → N-Isopropyl-1-[3-(3-hydroxy-3-phenylbut-1-ynyl)phenyl]-1,4-dihydro [1,8]naphthyridin-4-one-3-carboxamide

HRID 351735

반응식

HRID 351735 반응식
[CH:1]([NH:4][C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:9]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20](Br)[CH:19]=2)[CH:8]=1)=[O:6])([CH3:3])[CH3:2].[C:25]1([C:31]([OH:35])([C:33]#[CH:34])[CH3:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(N(CC)CC)C>CN(C=O)C.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].Cl[Pd]Cl.[Cu]I>[CH:1]([NH:4][C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:9]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:34]#[C:33][C:31]([OH:35])([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH3:32])[CH:19]=2)[CH:8]=1)=[O:6])([CH3:3])[CH3:2]

참가 물질

8

반응물 3

HCID 8471TriethylamineHCID 920983-Hydroxy-3-phenyl-1-butyneHCID 129913181-(3-bromophenyl)-N-isopropyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide

생성물 1

HCID 10161154N-Isopropyl-1-[3-(3-hydroxy-3-phenylbut-1-ynyl)phenyl]-1,4-dihydro [1,8]naphthyridin-4-one-3-carboxamide

시약·촉매·용매 4

HCID 24290Palladium Chloride촉매HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 6228Dimethylformamide용매

반응 조건

온도
85 °C

실험 절차

A mixture of N-isopropyl-1-(3-bromophenyl)-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxamide from Step 4 of EXAMPLE 1, 2-phenyl-3-butyn-2-ol (2 eq), triethylamine (1.66 eq), bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.05 eq), and copper(I) iodide (5 mg/mmol) in DMF (20 ml/mmol) was heated at 85° C. for 18 hours. After cooling to room temperature, the resulting mixture was quenched with saturated aqueous ammonium chloride solution and partitioned between ethyl acetate and water. The crude product from the organic phase was chromatographed on silica gel eluting with 20% ether in methylene chloride. The purified product was stirred in ether at room temperature for 3 hours and filtered to afford the title compound as a white solid.

후처리

  1. temperatureAfter cooling to room temperature
  2. customthe resulting mixture was quenched with saturated aqueous ammonium chloride solution
  3. custompartitioned between ethyl acetate and water
  4. customThe crude product from the organic phase was chromatographed on silica gel eluting with 20% ether in methylene chloride
  5. filtrationfiltered

출처 및 근거

ORD 기록
ord-dd67d90dc91049d59b4870fc9e136467
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06743802B2

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