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

HRID 337172Notes

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-ae0bb0d2a33d4095a113c4b7cabab74e
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889692B2

Reaction notes

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