Ethyl Acetate → 3-{[2-(azetidin-1-ylcarbonyl)pyrimidin-5-yl]oxy}-5-[(1-methylethyl)oxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide

HRID 1011714ノート

反応式

HRID 1011714 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([CH:14]=[C:15]([O:17][CH:18]([CH3:20])[CH3:19])[CH:16]=1)[C:5]([NH:7][C:8]1[CH:12]=[CH:11][N:10]([CH3:13])[N:9]=1)=[O:6].[N:21]1([C:25]([C:27]2[N:32]=[CH:31][C:30](Br)=[CH:29][N:28]=2)=[O:26])[CH2:24][CH2:23][CH2:22]1.C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>CC(N(C)C)=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]Br.O>[N:21]1([C:25]([C:27]2[N:28]=[CH:29][C:30]([O:1][C:2]3[CH:3]=[C:4]([CH:14]=[C:15]([O:17][CH:18]([CH3:20])[CH3:19])[CH:16]=3)[C:5]([NH:7][C:8]3[CH:12]=[CH:11][N:10]([CH3:13])[N:9]=3)=[O:6])=[CH:31][N:32]=2)=[O:26])[CH2:24][CH2:23][CH2:22]1

参加物

8

反応物 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 536296392-(Azetidin-1-ylcarbonyl)-5-bromopyrimidineHCID 591271833-hydroxy-5-isopropoxy-N-(1-methyl-1H-pyrazol-3-yl)benzamide

生成物 1

HCID 536295393-{[2-(azetidin-1-ylcarbonyl)pyrimidin-5-yl]oxy}-5-[(1-methylethyl)oxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide収率 50.1%

試薬・触媒・溶媒 3

HCID 11251615Bromotris(triphenylphosphine)copper(I)触媒HCID 962Water溶媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
160 °C

実験手順

A mixture of 3-hydroxy-5-[(1-methylethyl)oxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide (250 mg, 0.91 mmol), 2-(azetidin-1-ylcarbonyl)-5-bromopyrimidine (242 mg, 1.0 mmol), cesium carbonate (886 mg, 2.72 mmol) and bromotris(triphenylphosphine)copper(I) (423 mg, 0.45 mmol) in DMA (5 mL) was stirred in a ‘Biotage initiator Microwave’ at 160° C. for 4 hours. The mixture was added to ethyl acetate (50 mL) and water (50 mL), the organic layer washed with brine (50 mL), dried (MgSO4), filtered and the solvent removed in vacuo to give a brown oil. The residue was chromatographed on silica, eluting with a gradient of 0-10% methanol in ethyl acetate, to give the desired compound (199 mg).

後処理

  1. washthe organic layer washed with brine (50 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customthe solvent removed in vacuo
  5. customto give a brown oil
  6. customThe residue was chromatographed on silica
  7. washeluting with a gradient of 0-10% methanol in ethyl acetate

出典と根拠

ORDレコード
ord-281b6afa924141fab22dde8d030bbdad
出典データセット
uspto-grants-2011_07
特許番号
US07977328B2

反応ノート

読み込み中…