O-Methylhydroxylamine hydrochloride → HCID 86663243, compound

HRID 337053Notes

Reaction equation

HRID 337053 reaction equation
C([Mg]Cl)(C)C.[CH3:6][C:7]1[CH:16]=[CH:15][C:10]([C:11](OC)=[O:12])=[CH:9][C:8]=1[N:17]1[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C@@H:24]([C:33]2[C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH:36]=[CH:35][CH:34]=2)[C@@H:25]([CH3:32])[CH2:26][N:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)[C:18]1=[O:43].Cl.[CH3:45][O:46][NH2:47]>O1CCCC1>[CH3:45][O:46][NH:47][C:11](=[O:12])[C:10]1[CH:15]=[CH:16][C:7]([CH3:6])=[C:8]([N:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C@@H:24]([C:33]3[C:42]4[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=4)[CH:36]=[CH:35][CH:34]=3)[C@@H:25]([CH3:32])[CH2:26][N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)[C:18]2=[O:43])[CH:9]=1

Participants

5

Reactant 3

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 86663244HCID 86663244, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 86663243HCID 86663243, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of iso-propylmagnesium chloride (2M in diethyl ether, 1.2 mL) was added dropwise to a stirred mixture of 4-methyl-3-[3-[[(1R,2S)-2-methyl-1-(1-naphthalenyl)-3-(1-pyrrolidinyl)propyl]amino]-2-oxo-1(2H)-pyrazinyl]-benzoic acid, methyl ester (Example 158b, 90 mg), O-methylhydroxylamine hydrochloride (65 mg) and tetrahydrofuran (2 mL) at room temperature. After 15 min the reaction was quenched with sat. aqueous NH4Cl and extracted into ethyl acetate. The organic phase was dried (Na2SO4), filtered and concentrated in vacuo. Purification by preparative HPLC (Gemini column, 0.1% ammonia:acetonitrile eluent) afforded the title compound as a solid (65 mg).

Workup

  1. customAfter 15 min the reaction was quenched with sat. aqueous NH4Cl
  2. extractionextracted into ethyl acetate
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by preparative HPLC (Gemini column, 0.1% ammonia:acetonitrile eluent)

Sources & evidence

ORD record
ord-e9d1cb27e8444a18b46b5382352bad40
Source dataset
uspto-grants-2014_11
Patent number
US08889692B2

Reaction notes

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