Hydrochloric Acid → 3-[5-Bromo-3-[[1-methyl-1-[2-(phenylmethoxy)phenyl]ethyl]amino]-2-oxo-1(2H)-pyrazinyl]-N-cyclopropyl-5-fluoro-4-methyl-benzamide

HRID 1697324Notes

Reaction equation

[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[Br:5][C:6]1[N:7]=[C:8]([NH:26][C:27]([CH3:43])([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH3:28])[C:9](=[O:25])[N:10]([C:12]2[CH:13]=[C:14]([CH:20]=[C:21]([F:24])[C:22]=2[CH3:23])[C:15](OCC)=[O:16])[CH:11]=1.C([Mg]Cl)(C)C.Cl>C1COCC1>[Br:5][C:6]1[N:7]=[C:8]([NH:26][C:27]([CH3:43])([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[O:35][CH2:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH3:28])[C:9](=[O:25])[N:10]([C:12]2[CH:13]=[C:14]([CH:20]=[C:21]([F:24])[C:22]=2[CH3:23])[C:15]([NH:4][CH:1]2[CH2:3][CH2:2]2)=[O:16])[CH:11]=1

Participants

Conditions

Temperature: 75 °C

Procedure

Cyclopropylamine (1.86 mL) was added to 3-[5-bromo-3-[[1-methyl-1-[2-(phenylmethoxy)phenyl]ethyl]amino]-2-oxo-1(2H)-pyrazinyl]-5-fluoro-4-methyl-benzoic acid, ethyl ester (Example 169e, 1.6 g) in THF (24 mL) under nitrogen at room temperature and isopropylmagnesium chloride (5.28 mL of a 2M solution in THF) was then added dropwise over 10 min. The resulting solution was stirred at 75° C. for 16 h. After cooling to room temperature, the solution was acidified with 2M HCl and extracted into dichloromethane. The organic fractions were concentrated in vacuo to give the subtitle compound (0.7 g).

Workup

temperatureAfter cooling to room temperature
extractionextracted into dichloromethane
concentrationThe organic fractions were concentrated in vacuo

Sources & evidence

ORD record: ord-887aadaf2bd74eadb420a0d7f52ae5ad
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163905B2

Reaction notes

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