Hydrochloric Acid → N-Cyclopropyl-3-(3-(1-(2-hydroxyphenyl)cyclopropylamino)-2-oxopyrazin-1(2H)-yl)-4-methylbenzamide

HRID 2070736Notes

Reaction equation

HRID 2070736 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[OH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1([NH:15][C:16]2[C:17](=[O:33])[N:18]([C:22]3[CH:23]=[C:24]([CH:29]=[CH:30][C:31]=3[CH3:32])[C:25](OC)=[O:26])[CH:19]=[CH:20][N:21]=2)[CH2:14][CH2:13]1.C([Mg]Cl)(C)C.Cl>C1COCC1.O>[CH:1]1([NH:4][C:25](=[O:26])[C:24]2[CH:29]=[CH:30][C:31]([CH3:32])=[C:22]([N:18]3[CH:19]=[CH:20][N:21]=[C:16]([NH:15][C:12]4([C:7]5[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=5[OH:5])[CH2:14][CH2:13]4)[C:17]3=[O:33])[CH:23]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 69828CyclopropylamineHCID 66689475Methyl 3-(3-(1-(2-hydroxyphenyl)cyclopropylamino)-2-oxopyrazin-1(2H)-yl)-4-methylbenzoateHCID 178418918HCID 178418918, compound2×

Product 1

HCID 66688774N-Cyclopropyl-3-(3-(1-(2-hydroxyphenyl)cyclopropylamino)-2-oxopyrazin-1(2H)-yl)-4-methylbenzamideYield 97.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To cyclopropylamine (0.60 mL, 8.46 mmol) and Methyl 3-(3-(1-(2-hydroxyphenyl)cyclopropylamino)-2-oxopyrazin-1(2H)-yl)-4-methylbenzoate (Example 167c, 0.331 g) in THF (5 mL) at rt was added isopropylmagnesium chloride (0.85 mL of a 2M solution in THF) dropwise. The reaction was stirred for 1 h and then further isopropylmagnesium chloride (0.85 mL of 2M solution in THF) was added and the reaction stirred for 16 h. Water and 2M aqueous HCl were cautiously added and the aqueous layer extracted with dichloromethane (2×). The combined organics were dried (Na2SO4) and the solvent removed in vacuo to give the subtitle product as a yellow solid (0.342 g).

Workup

  1. stirringthe reaction stirred for 16 h
  2. extractionthe aqueous layer extracted with dichloromethane (2×)
  3. dry with materialThe combined organics were dried (Na2SO4)
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-75353ab86dee407db5846aa47280ca86
Source dataset
uspto-grants-2012_10
Patent number
US08299246B2

Reaction notes

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