Methylamine → 4-Chloro-N-cyclopropyl-3-[3-[(1-methyl-1-{2-[2-(methylamino)ethoxy]phenyl}ethyl)amino]-2-oxopyrazin-1(2H)-yl]benzamide

HRID 2070855Notes

Reaction equation

[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([C:6]([NH:8][CH:9]2[CH2:11][CH2:10]2)=[O:7])=[CH:4][C:3]=1[N:14]1[CH:19]=[CH:18][N:17]=[C:16]([NH:20][C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[O:30][CH2:31][CH2:32]Cl)([CH3:23])[CH3:22])[C:15]1=[O:34].[CH3:35][NH2:36]>C(#N)C>[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([C:6]([NH:8][CH:9]2[CH2:11][CH2:10]2)=[O:7])=[CH:4][C:3]=1[N:14]1[CH:19]=[CH:18][N:17]=[C:16]([NH:20][C:21]([CH3:22])([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[O:30][CH2:31][CH2:32][NH:36][CH3:35])[CH3:23])[C:15]1=[O:34]

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 4-chloro-3-[3-({1-[2-(2-chloroethoxy)phenyl]-1-methylethyl}amino)-2-oxopyrazin-1(2H)-yl]-N-cyclopropylbenzamide (Example 3301, 0.22 g) dissolved in acetonitrile (3 mL) was treated with 40% aqueous methylamine (0.380 mL). The resulting mixture was stirred at 100° C. for 16 h in a sealed tube. The reaction mixture was filtered and purified by preparative HPLC (Phenominex Gemini column using a 95-5% gradient of aqueous 0.2% ammonia in acetonitrile as eluent). The fractions containing the desired compound were evaporated to afford the title compound (0.087 g).

Workup

filtrationThe reaction mixture was filtered
custompurified by preparative HPLC (Phenominex Gemini column
additionThe fractions containing the desired compound
customwere evaporated

Sources & evidence

ORD record: ord-fb8d9c046d8c423ea03d7a80620e167b
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299246B2

Reaction notes

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