Benzyl mercaptan → HCID 66685983, compound

HRID 2070717Notes

Reaction equation

HRID 2070717 reaction equation
[CH:1]([Mg]Cl)([CH3:3])[CH3:2].[CH:6]1([NH:9][C:10](=[O:32])[C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([N:18]3[CH:23]=[CH:22][N:21]=[C:20](OC4C=CC=CC=4)[C:19]3=[O:31])[CH:12]=2)[CH2:8][CH2:7]1.C1C=CC(C[SH:40])=CC=1.[NH4+].[Cl-].O1C[CH2:46][CH2:45][CH2:44]1>O>[CH:6]1([NH:9][C:10](=[O:32])[C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([N:18]3[CH:23]=[CH:22][N:21]=[C:20]([S:40][C:1]4[CH:3]=[CH:46][CH:45]=[CH:44][CH:2]=4)[C:19]3=[O:31])[CH:12]=2)[CH2:7][CH2:8]1

Participants

7

Reactant 5

HCID 7509Benzyl mercaptanHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 66686295HCID 66686295, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 66685983HCID 66685983, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of iso-propylmagnesium chloride (2M in tetrahydrofuran, 0.5 mL) was added to a stirred mixture of N-cyclopropyl-4-methyl-3-(2-oxo-3-phenoxy-1(2H)-pyrazinyl)-benzamide (Example 116, 45 mg), benzylthiol (0.2 mL) and tetrahydrofuran (0.5 mL) and the mixture was stirred at room temperature for 36 h. Solid NH4Cl and water were added and the mixture extracted into ethyl acetate. The organic phase was dried (Na2SO4) and concentrated in vacuo. Purification by preparative HPLC (Gemini column, 0.1% ammonia: acetonitrile eluent) afforded the title compound as a solid (8 mg).

Workup

  1. extractionthe mixture extracted into ethyl acetate
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customPurification by preparative HPLC (Gemini column, 0.1% ammonia: acetonitrile eluent)

Sources & evidence

ORD record
ord-504efb4a637d4d388267009f04ae292e
Source dataset
uspto-grants-2012_10
Patent number
US08299246B2

Reaction notes

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