Acetyl chloride → HCID 11996395, compound

HRID 655862Notes

Reaction equation

HRID 655862 reaction equation
[N:1]1[CH:5]=[C:4]([C:6]2[CH:7]=[C:8]([N:12]3[C:16]4=[N:17][CH:18]=[N:19][C:20]([NH2:21])=[C:15]4[CH:14]=[N:13]3)[CH:9]=[CH:10][CH:11]=2)[NH:3][CH:2]=1.[H-].[Na+].[C:24](Cl)(=[O:26])[CH3:25]>CN(C=O)C>[NH2:21][C:20]1[N:19]=[CH:18][N:17]=[C:16]2[N:12]([C:8]3[CH:7]=[C:6]([C:4]4[N:3]=[CH:2][N:1]([C:24](=[O:26])[CH3:25])[CH:5]=4)[CH:11]=[CH:10][CH:9]=3)[N:13]=[CH:14][C:15]=12

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 11995686HCID 11995686, compound

Product 1

HCID 11996395HCID 11996395, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Title compound 6A, 1-[3-(3H-Imidazol-4-yl)-phenyl]-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine (30 mg, 1.0 eq, 0.11 mmol) was dissolved in DMF (2 ml) and to this was added sodium hydride as a 60% dispersion in oil (5 mg, 1.1 eq, 0.12 mmol), the mixture was then stirred under an inert atmosphere for 20 minutes. To this was added acetyl chloride (7.7 μl, 1.1 eq, 0.12 mmol) the reaction was the stirred for 18 hours and allowed to warm to room temperature. Solvent was then remove in vacuo. The resultant residue was purified using mass-directed preparative HPLC to yield the compound as an off white solid (2.1 mg, 0.0007 mmol, 6%). LCMS: [M+H]+=320, Rt=1.32 min, 87% purity.

Workup

  1. stirringstirred for 18 hours
  2. customSolvent was then remove in vacuo
  3. customThe resultant residue was purified

Sources & evidence

ORD record
ord-0cd1125001174f2d916507f97b27a970
Source dataset
uspto-grants-2011_12
Patent number
US08071607B2

Reaction notes

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