Cyclopropylamine → 3-[3-({1-[2-(Benzyloxy)phenyl]-1-methylethyl}amino)-2-oxopyrazin-1(2H)-yl]-4-chloro-N-cyclopropylbenzamide

HRID 2070852Notes

Reaction equation

CO[C:3](=[O:36])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[C:6]([N:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH:17][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)([CH3:20])[CH3:19])[C:12]2=[O:35])[CH:5]=1.[CH:37]1([NH2:40])[CH2:39][CH2:38]1.C([Mg]Cl)(C)C>C1COCC1.[Cl-].[NH4+]>[CH2:28]([O:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:18]([NH:17][C:13]1[C:12](=[O:35])[N:11]([C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=2[Cl:10])[C:3]([NH:40][CH:37]2[CH2:39][CH2:38]2)=[O:36])[CH:16]=[CH:15][N:14]=1)([CH3:20])[CH3:19])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of methyl-3-[3-({1-[2-(benzyloxy)phenyl]-1-methylethyl}amino)-2-oxopyrazin-1(2H)-yl]-4-chlorobenzoate (Example 330f, 2.23 g) dissolved in THF (30 mL) was treated with cyclopropylamine (2.261 mL) and 2.0M Isopropylmagnesium chloride (11.06 mL) under nitrogen. The resulting solution was stirred at 20° C. for 2 h. The reaction mixture was diluted with aqueous ammonium chloride (150 mL), and extracted with dichloromethane (250 mL). The organic was dried (MgSO4), filtered and evaporated to afford the subtitle compound (2.40 g).

Workup

extractionextracted with dichloromethane (250 mL)
dry with materialThe organic was dried (MgSO4)
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-e7d815bc327647cf8ca3d65b41ee7f6b
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299246B2

Reaction notes

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