Acetone → 4-[(2-Cyanopropan-2-yl)amino]-2-fluoro-N-methylbenzamide

HRID 515798Notes

Reaction equation

HRID 515798 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][CH3:9])=[O:7])=[C:4]([F:12])[CH:3]=1.[Si]([C:17]#[N:18])(C)(C)C.[Si](OS(C(F)(F)F)(=O)=O)(C)(C)C.[CH3:31][C:32]([CH3:34])=O>C(Cl)Cl>[C:17]([C:32]([NH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][CH3:9])=[O:7])=[C:4]([F:12])[CH:3]=1)([CH3:34])[CH3:31])#[N:18]

Participants

6

Reactant 4

HCID 180AcetoneHCID 65367Trimethylsilyl triflateHCID 82115Trimethylsilyl cyanideHCID 441395214-Amino-2-fluoro-N-methylbenzamide

Product 1

HCID 592965474-[(2-Cyanopropan-2-yl)amino]-2-fluoro-N-methylbenzamideYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-amino-2-fluoro-N-methylbenzamide (2 g, 11.9 mmol), TMSCN (2.2 mL, 17.9 mmol), TMSOTf (0.1 mL, 0.6 mmol), and acetone (10 mL, 140 mmol) in DCM (20 mL) was stirred at room temperature overnight. The white solid was filtered, washed with a small amount of DCM, and dried to afford 1.12 g of 4-((2-cyanopropan-2-yl)amino)-2-fluoro-N-methylbenzamide as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 7.79 (t, 1H), 7.56 (t, 1H), 6.88 (s, 1H), 6.67 (dd, 1H), 6.54 (dd, 1H), 2.75 (d, 3H), 1.67 (s, 6H).

Workup

  1. filtrationThe white solid was filtered
  2. washwashed with a small amount of DCM
  3. customdried

Sources & evidence

ORD record
ord-d9cc09fa78ed43669f81b39b6b08c6bf
Source dataset
uspto-grants-2015_08
Patent number
US09108944B2

Reaction notes

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