Acetic Anhydride → HCID 25065894, compound

HRID 42211Notes

Reaction equation

HRID 42211 reaction equation
[CH2:1]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([N:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[CH:26][N:25]=3)[CH2:20][CH2:19]2)=[N:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].[CH3:34][C:35](OC(C)=O)=[O:36]>CCO.Cl[Ni]Cl>[CH2:1]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([N:18]2[CH2:23][CH2:22][N:21]([C:24]3[N:25]=[CH:26][C:27]([CH2:28][NH:29][C:35](=[O:36])[CH3:34])=[CH:30][CH:31]=3)[CH2:20][CH2:19]2)=[N:10][N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 4311764Sodium borohydrideHCID 250665186-[4-[4-(Phenylmethyl)-1-phthalazinyl]-1-piperazinyl]-3-pyridinecarbonitrile

Product 1

HCID 25065894HCID 25065894, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 24385Nickel DichlorideCatalystHCID 702EthanolSolvent

Procedure

In a 100 ml, round-bottom flask equipped with a stir bar, 6-[4-(4-Benzyl-phthalazin-1-yl)-piperazin-1-yl]-nicotinonitrile (150 mg, 0.362 mmol) is dissolved in anhydrous EtOH (7 mL) followed by the addition of NiCl2 (0.398 mmol). NaBH4 (0.723 mmol) is added in portions and the reaction is stirred for 2 h under a N2 atmosphere. The septum is removed and Ac2O (1.08 mmol) is added. The reaction is capped again and stirred for one additional hour. LC/MS shows full conversion to the acylated product. The reaction is filtered through a Celite pad and rinsed with 50 ml of MeOH. The final compound is purified by preparative HPLC using a C-18 column and propanol as the modifier (85 mg, 52% yield).

Workup

  1. customIn a 100 ml, round-bottom flask equipped with a stir bar
  2. customThe septum is removed
  3. customThe reaction is capped again
  4. stirringstirred for one additional hour
  5. filtrationThe reaction is filtered through a Celite pad
  6. washrinsed with 50 ml of MeOH
  7. customThe final compound is purified by preparative HPLC

Sources & evidence

ORD record
ord-77962e20c9fa428fa704765a63fae635
Source dataset
uspto-grants-2013_09
Patent number
US08536168B2

Reaction notes

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