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

HRID 1697317Notes

Reaction equation

HRID 1697317 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-cb4188957f5d45958b19f5104e19a265
Source dataset
uspto-grants-2012_04
Patent number
US08163905B2

Reaction notes

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