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

HRID 2070724노트

반응식

HRID 2070724 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
120 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-41bb6d6a6c0b46079d3b58f17f9a098f
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299246B2

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