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

HRID 869809Notes

Reaction equation

HRID 869809 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]=[C:17]([N:19]2[CH:24]=[CH:23][N:22]=[C:21]([NH:25][C:26]3([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[OH:35])[CH2:28][CH2:27]3)[C:20]2=[O:36])[C:16]([CH3:37])=[C:15]([F:38])[CH:14]=1.Cl>C1COCC1.O>[CH:6]1([NH:9][C:12](=[O:11])[C:13]2[CH:18]=[C:17]([N:19]3[CH:24]=[CH:23][N:22]=[C:21]([NH:25][C:26]4([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=5[OH:35])[CH2:28][CH2:27]4)[C:20]3=[O:36])[C:16]([CH3:37])=[C:15]([F:38])[CH:14]=2)[CH2:8][CH2:7]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 69828CyclopropylamineHCID 666898943-fluoro-5-[3-[[1-(2-hydroxyphenyl)cyclopropyl]amino]-2-oxo-1(2H)-pyrazinyl]-4-methyl-benzoic acid methyl esterHCID 178418918HCID 178418918, compound

Product 1

HCID 66690808N-Cyclopropyl-3-fluoro-5-[3-[[1-(2-hydroxyphenyl)cyclopropyl]amino]-2-oxo-1(2H)-pyrazinyl]-4-methyl-benzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Isopropylmagnesium chloride (30.1 ml of a 2M solution in THF) was added over 20 min to a solution of cyclopropylamine (10.61 mL) and 3-fluoro-5-[3-[[1-(2-hydroxyphenyl)cyclopropyl]amino]-2-oxo-1(2H)-pyrazinyl]-4-methyl-benzoic acid methyl ester (Preparation 1j, 6.16 g) in tetrahydrofuran (200 mL) and the reaction stirred at room temperature under nitrogen for 1 h. Water (100 mL) and 2M HCl (200 mL) were cautiously added and the aqueous layer extracted with dichloromethane (3×200 mL) and the combined organic extracts dried (MgSO4) and the solvent removed to give the subtitle compound (5.00 g).

Workup

  1. extractionthe aqueous layer extracted with dichloromethane (3×200 mL)
  2. dry with materialthe combined organic extracts dried (MgSO4)
  3. customthe solvent removed

Sources & evidence

ORD record
ord-66602b48bbdb4bee9cc0934b6933bf58
Source dataset
uspto-grants-2015_03
Patent number
US08969350B2

Reaction notes

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