Dichloromethane → N-(sec-butyl)-4-chloro-3-[3-{(1-(2-hydroxyphenyl)-1-methylethyl]amino}-2-oxopyrazin-1(2H)-yl]benzamide

HRID 337173Notes

Reaction equation

C([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]([NH:18][C:19]1[C:20](=[O:38])[N:21]([C:25]2[CH:26]=[C:27]([CH:34]=[CH:35][C:36]=2[Cl:37])[C:28]([NH:30][CH:31]2[CH2:33][CH2:32]2)=[O:29])[CH:22]=[CH:23][N:24]=1)([CH3:17])[CH3:16])C1C=CC=CC=1.B(Br)(Br)Br.[CH2:43](Cl)Cl>O>[CH:31]([NH:30][C:28](=[O:29])[C:27]1[CH:34]=[CH:35][C:36]([Cl:37])=[C:25]([N:21]2[CH:22]=[CH:23][N:24]=[C:19]([NH:18][C:15]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[OH:8])([CH3:17])[CH3:16])[C:20]2=[O:38])[CH:26]=1)([CH2:33][CH3:32])[CH3:43]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 3-[3-({1-[2-(benzyloxy)phenyl]-1-methylethyl}amino)-2-oxopyrazin-1(2H)-yl]-4-chloro-N-cyclopropylbenzamide (Example 330g, 2.23 g) dissolved in DCM (30 mL) was treated with boron tribromide (8.43 mL of a 1M solution in DCM) at 0° C. under nitrogen. The resulting mixture was stirred at 0° C. for 1 h. The reaction mixture was diluted with water (200 mL), and extracted with dichloromethane (250 mL). The organic was dried (MgSO4), filtered and evaporated to afford crude product. The crude product was triturated with diethyl ether (50 mL) to afford the subtitle compound (1.760 g).

Workup

extractionextracted with dichloromethane (250 mL)
dry with materialThe organic was dried (MgSO4)
filtrationfiltered
customevaporated
customto afford crude product
customThe crude product was triturated with diethyl ether (50 mL)

Sources & evidence

ORD record: ord-f17b71feab764badbf043d980742ccff
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889692B2

Reaction notes

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