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

HRID 337115Notes

Reaction equation

HRID 337115 reaction equation
C([Mg]Cl)(C)C.[CH:6]1([NH2:9])[CH2:8][CH2:7]1.C[O:11][C:12](=O)[C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]([N:20]2[CH:25]=[CH:24][N:23]=[C:22]([NH:26][C:27]3([C:30]4[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:31]=4[OH:37])[CH2:29][CH2:28]3)[C:21]2=[O:38])[CH:14]=1.Cl>C1COCC1.O>[CH:6]1([NH:9][C:12](=[O:11])[C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]([N:20]3[CH:25]=[CH:24][N:23]=[C:22]([NH:26][C:27]4([C:30]5[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:31]=5[OH:37])[CH2:29][CH2:28]4)[C:21]3=[O:38])[CH:14]=2)[CH2:8][CH2:7]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 69828CyclopropylamineHCID 666905583-[3-[[1-(5-fluoro-2-hydroxyphenyl)cyclopropyl]amino]-2-oxo-1(2H)-pyrazinyl]-4-methyl-benzoic acid methyl esterHCID 178418918HCID 178418918, compound

Product 1

HCID 66689006N-cyclopropyl-3-[3-[[1-(5-fluoro-2-hydroxyphenyl)cyclopropyl]amino]-2-oxo-1(2H)-pyrazinyl]-4-methyl-benzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Isopropylmagnesium chloride (5.86 mL of a 2M solution in THF) was added over 20 min to a solution of cyclopropylamine (2.066 mL) and 3-[3-[[1-(5-fluoro-2-hydroxyphenyl)cyclopropyl]amino]-2-oxo-1(2H)-pyrazinyl]-4-methyl-benzoic acid methyl ester (Example 278c, 1.2 g) in THF (200 mL) at room temperature under nitrogen. The reaction mixture was stirred for 1 h. Water and 2M HCl were cautiously added and the aqueous layer extracted with dichloromethane (3×200 mL), dried (MgSO4) and the solvent removed to give the subtitle compound (1.22 g)

Workup

  1. extractionthe aqueous layer extracted with dichloromethane (3×200 mL)
  2. dry with materialdried (MgSO4)
  3. customthe solvent removed

Sources & evidence

ORD record
ord-a3124ff97df24f84965f0a8292d35d3f
Source dataset
uspto-grants-2014_11
Patent number
US08889692B2

Reaction notes

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