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Cyclopropylamine → N-Cyclopropyl-4-methyl-3-[3-[[[2-(methylthio)phenyl]methyl]amino]-2-oxo-1(2H)-pyrazinyl]-benzamide

HRID 337044
ノート
印刷プレビュー

反応式

HRID 337044 の反応式
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=O)=[CH:4][C:3]=1[N:12]1[CH:17]=[CH:16][N:15]=[C:14](OC2C=CC=CC=2)[C:13]1=[O:25].[CH3:26][S:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH2:34][NH2:35].[CH:36]1([NH2:39])[CH2:38][CH2:37]1.C1([Mg]Br)CCCC1>O1CCCC1>[CH:36]1([NH:39][C:6](=[O:8])[C:5]2[CH:10]=[CH:11][C:2]([CH3:1])=[C:3]([N:12]3[CH:17]=[CH:16][N:15]=[C:14]([NH:35][CH2:34][C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=4[S:27][CH3:26])[C:13]3=[O:25])[CH:4]=2)[CH2:38][CH2:37]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 69828CyclopropylamineHCID 27369812-(Methylthio)benzylamineHCID 866632394-Methyl-3-(2-oxo-3-phenoxy-1(2H)-pyrazinyl)-benzoic acid, methyl esterHCID 178419650HCID 178419650、化合物

生成物 1

HCID 66686300N-Cyclopropyl-4-methyl-3-[3-[[[2-(methylthio)phenyl]methyl]amino]-2-oxo-1(2H)-pyrazinyl]-benzamide

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

反応条件

温度
120 °C

実験手順

A mixture of 4-methyl-3-(2-oxo-3-phenoxy-2H-pyrazin-1-yl)-benzoic acid, methyl ester (Example 128a, 111 mg), 2-(methylthio)-benzenemethanamine (100 mg) and tetrahydrofuran (1 mL) was heated within a microwave for 5 h at 120° C. before being cooled to room temperature. Cyclopropylamine (0.2 mL) was added followed by addition of cyclopentylmagnesium bromide (2M in diethyl ether, 0.8 mL). The mixture was stirred for 10 min., quenched with sat. NH4Cl and extracted into ethyl acetate. The organic phase was concentrated in vacuo. Purification by preparative HPLC (Gemini column, 0.1% ammonia:acetonitrile eluent) afforded the title compound as a solid (39 mg).

後処理

  1. temperaturebefore being cooled to room temperature
  2. customquenched with sat. NH4Cl
  3. extractionextracted into ethyl acetate
  4. concentrationThe organic phase was concentrated in vacuo
  5. customPurification by preparative HPLC (Gemini column, 0.1% ammonia:acetonitrile eluent)

出典と根拠

ORDレコード
ord-c25f112a054e4f8a8e90ad4b9bef77e6
出典データセット
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08889692B2

反応ノート

読み込み中…

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