Water → N-cyclopropyl-3-{3-[2-(2-hydroxyphenyl)pyrrolidin-1-yl]-2-oxo-3,4-dihydropyrazin-1(2H)-yl]-4-methylbenzamide

HRID 337158Notes

Reaction equation

HRID 337158 reaction equation
[CH:1]1([NH:4][C:5](=[O:33])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([N:13]3[CH:18]=[CH:17][N:16]=[C:15]([N:19]4[CH2:23][CH2:22][CH2:21][CH:20]4[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[O:30]C)[C:14]3=[O:32])[CH:7]=2)[CH2:3][CH2:2]1.B(Br)(Br)Br.O>C(Cl)Cl>[CH:1]1([NH:4][C:5](=[O:33])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([N:13]3[CH:18]=[CH:17][NH:16][CH:15]([N:19]4[CH2:23][CH2:22][CH2:21][CH:20]4[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[OH:30])[C:14]3=[O:32])[CH:7]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromide2×HCID 66689260N-cyclopropyl-3-(3-(2-(2-methoxyphenyl)pyrrolidin-1-yl)-2-oxopyrazin-1(2H)-yl)-4-methylbenzamide

Product 1

HCID 66689880N-cyclopropyl-3-{3-[2-(2-hydroxyphenyl)pyrrolidin-1-yl]-2-oxo-3,4-dihydropyrazin-1(2H)-yl]-4-methylbenzamideYield 81.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To N-cyclopropyl-3-(3-(2-(2-methoxyphenyl)pyrrolidin-1-yl)-2-oxopyrazin-1(2H)-yl)-4-methylbenzamide (Example 97, 0.993 g) in DCM (10 mL) was added boron tribromide (4.47 mL of a 1M solution in DCM) at 0° C. and the reaction stirred for 3 h. Further Boron tribromide (4.47 mL of a 1M solution in DCM) was added and the reaction stirred for 3 h. Ice was added followed by water and the aqueous layer extracted with DCM then EtOAc. The aqueous layer was neutralised to pH 7 and extracted with DCM then EtOAc and all the combined organics dried (Na2SO4) and the solvent removed to give the subtitle compound as a solid (0.786 g).

Workup

  1. stirringthe reaction stirred for 3 h
  2. additionIce was added
  3. extractionthe aqueous layer extracted with DCM
  4. extractionextracted with DCM
  5. dry with materialEtOAc and all the combined organics dried (Na2SO4)
  6. customthe solvent removed

Sources & evidence

ORD record
ord-caed0fb7211349fc944c688160406a8f
Source dataset
uspto-grants-2014_11
Patent number
US08889692B2

Reaction notes

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