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

HRID 1697304

Reaction equation

[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

Participants

Conditions

Temperature: 120 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-e922688b4a1a402684b60605e642fc35
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163905B2

Linked notes

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