Cyclopentanone → HCID 22235945, compound

HRID 1744145Notes

Reaction equation

HRID 1744145 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([S:15][CH:16]([CH2:23][CH:24]([CH3:26])[CH3:25])[C:17]([NH:19][CH2:20][C:21]#[N:22])=[O:18])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[C:27]1(=O)[CH2:31]C[CH2:29][CH2:28]1.C([BH3-])#N.[Na+].[O-]S([O-])(=O)=O.[Mg+2].C([O-])(O)=O.[Na+]>>[C:21]([CH2:20][NH:19][C:17](=[O:18])[CH:16]([S:15][C:12]1[CH:13]=[CH:14][C:9]([C:6]2[CH:7]=[CH:8][C:3]([CH2:2][N:1]3[CH2:29][CH2:28][CH2:27][CH2:31]3)=[CH:4][CH:5]=2)=[CH:10][CH:11]=1)[CH2:23][CH:24]([CH3:26])[CH3:25])#[N:22]

Participants

6

Reactant 5

HCID 8452CyclopentanoneHCID 24083Sulfuric acid magnesium salt (1:1)HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 22236104HCID 22236104, compound

Product 1

HCID 22235945HCID 22235945, compound

Procedure

2-{[4′-(Aminomethyl)-1,1′-biphenyl-4-yl]thio}-N-(cyanomethyl)-4-methylpentanamide (120 mg, 0.33 mmol) was mixed with cyclopentanone (234 μL, 2.64 mmol), sodium cyanoborohydride (25 mg, 0.40 mmol) and MgSO4 (200 mg) and stirred for 18 h. Aqueous sat. NaHCO3 was added, the product was extracted with EtOAc (3×), dried over MgSO4, concentrated in vacuo, and purified by flash chromatography (100% EtOAc to 2% methanol/EtOAc) to afford N-(cyanomethyl)-4-methyl-2-{[4′-(pyrrolidin-1-ylmethyl)-1,1′-biphenyl4-yl]thio}pentanamide. MS (+APCI): 436.3 [M+1]+.

Workup

  1. extractionthe product was extracted with EtOAc (3×)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography (100% EtOAc to 2% methanol/EtOAc)

Sources & evidence

ORD record
ord-672999fb4aea43baa8b55beb53ec20d9
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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