Water → HCID 69264825, compound

HRID 1007847Notes

Reaction equation

HRID 1007847 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([Cl:21])[CH:14]=2)=[N:9][C:8](Cl)=[CH:7][N:6]=1)=[O:4].[OH:23][CH2:24][CH:25]1[CH2:29][CH2:28][CH2:27][NH:26]1.C(N(CC)CC)C.O>O1CCCC1>[CH3:1][O:2][C:3]([C:5]1[C:10]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([Cl:21])[CH:14]=2)=[N:9][C:8]([N:26]2[CH2:27][CH2:28][CH2:29][C@H:25]2[CH2:24][OH:23])=[CH:7][N:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 90908Prolinol2×HCID 22665590HCID 22665590, compound

Product 1

HCID 69264825HCID 69264825, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-methoxycarbonyl-3-(3-chloro-4-methoxybenzylamino)-5-chloropyrazine (150 mg), 2-hydroxymethylpyrrolidine (88.6 mg), and triethylamine (0.12 ml) in tetrahydrofuran (5 ml) is stirred at room temperature for 4 hours, and the mixture is heated at 50° C. for 2 hours. To the mixture is added 2-hydroxymethylpyrrolidine (44.3 mg), and the mixture is stirred at 50° C. for one hour. After cooling, water is added to the reaction mixture, and the mixture is extracted with ethyl acetate. The extract is washed with water and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting yellow oil is purified by silica gel column chromatography (solvent; chloroform:hexane=1:1) to give (S)-2-methoxycarbonyl-3-(3-chloro-4-methoxybenzylamino)-5-(2-hydroxymethyl-1-pyrrolidinyl)-pyrazine (123 mg) as pale yellow powder, MS (m/z): 407 (MH+).

Workup

  1. temperaturethe mixture is heated at 50° C. for 2 hours
  2. stirringthe mixture is stirred at 50° C. for one hour
  3. temperatureAfter cooling
  4. extractionthe mixture is extracted with ethyl acetate
  5. washThe extract is washed with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting yellow oil is purified by silica gel column chromatography (solvent; chloroform:hexane=1:1)

Sources & evidence

ORD record
ord-7b5f25850c3b4df0b102805c7e1df113
Source dataset
uspto-grants-2004_09
Patent number
US06797709B2

Reaction notes

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