Acetic Acid → HCID 178482592, compound

HRID 2391011Notes

Reaction equation

HRID 2391011 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:3]=1[C:4]([NH:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([CH:13]=O)[CH2:9][CH2:8]1)=[O:5].C(O)(=O)C(O)=O.[CH3:26][NH:27][CH2:28][C:29]1[NH:33][N:32]=[C:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:30]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:3]=1[C:4]([NH:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([CH2:13][N:27]([CH3:26])[CH2:28][C:29]2[NH:33][N:32]=[C:31]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH:30]=2)[CH2:9][CH2:8]1)=[O:5]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 50944344HCID 50944344, compoundHCID 178520979HCID 178520979, compound

Product 1

HCID 178482592HCID 178482592, compoundYield 39.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 25 mL round-bottomed flask is added trans-2,5-dichloro-N-(4-formylcyclohexyl)benzamide (200 mg, 0.666 mmol) and N-methyl-1-(3-phenyl-1H-pyrazol-5-yl)methanamine oxalate (277 mg, 0.999 mmol) in DCM (15 mL) to give a colorless solution. Acetic acid (0.153 mL, 2.67 mmol) and sodium triacetoxyborohydride (424 mg, 1.999 mmol) are added and the mixture stirred at room temp for 90 minutes. 1M sodium hydroxide solution (4 mL) is added and the mixture is stirred at room temp for 10 minutes. The mixture is passed through a phase separator and evaporated to give a colourless oil. The crude mixture is re-dissolved in the minimum amount of DCM and applied to a pre-packed 12 g silica gel column and eluted with 0-100% EtOAc/isohexane over 6 minutes then 100% EtOAc for 8 minutes. Pure product is recovered as a colourless oil. The oil is dissolved in the minimum amount of DCM and triturated/sonicated with 9:1 isohexane/EtOAc to give a colourless solid 124 mg, [MH+ 471.30].

Workup

  1. customto give a colorless solution
  2. stirringthe mixture is stirred at room temp for 10 minutes
  3. customevaporated
  4. customto give a colourless oil
  5. washeluted with 0-100% EtOAc/isohexane over 6 minutes
  6. wait100% EtOAc for 8 minutes
  7. customPure product is recovered as a colourless oil
  8. dissolutionThe oil is dissolved in the minimum amount of DCM
  9. customtriturated/sonicated with 9:1 isohexane/EtOAc

Sources & evidence

ORD record
ord-a63e7fe9f19446a7aedafc06a4733e0f
Source dataset
uspto-grants-2012_09
Patent number
US08273900B2

Reaction notes

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