Formamidine acetate → HCID 51352545, compound

HRID 1408558Notes

Reaction equation

HRID 1408558 reaction equation
[CH:1]1([C:4]2[N:8]([C:9]3[C:14]([F:15])=[CH:13][C:12]([NH:16][C:17](=[O:26])[C:18](=[CH:22][N:23]([CH3:25])C)[C:19](=O)[CH3:20])=[CH:11][C:10]=3[F:27])[N:7]=[C:6]([C:28]([F:31])([F:30])[F:29])[CH:5]=2)[CH2:3][CH2:2]1.C(O)(=O)C.C(N)=[NH:37].CC[O-].[Na+]>C(O)C>[CH:1]1([C:4]2[N:8]([C:9]3[C:14]([F:15])=[CH:13][C:12]([NH:16][C:17]([C:18]4[C:19]([CH3:20])=[N:37][CH:25]=[N:23][CH:22]=4)=[O:26])=[CH:11][C:10]=3[F:27])[N:7]=[C:6]([C:28]([F:30])([F:29])[F:31])[CH:5]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 160693Formamidine acetateHCID 2723922Sodium ethoxideHCID 86652978HCID 86652978, compound

Product 1

HCID 51352545HCID 51352545, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-{4-[5-cyclopropyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-3,5-difluorophenyl}-2-[(dimethylamino)methylene]-3-oxobutanamide (700 mg, 1.6 mmol) and formamidine acetate (282 mg, 2.7 mmol) were dissolved in ethanol and added NaOEt (120 mg, 3.4 mmol). The above mixture was refluxed for 3 hr. Ethanol was removed on rotavapour and worked up (H2O/AcOEt) to obtain the crude. Crude was purified by column on 60-120 mesh silica gel using AcOEt and Petether (35:65) as eluent to obtain the title compound (34 mg) as a pale-yellow solid. M.P.: 147-150° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 11.25 (s, 1H), 9.18 (s, 1H), 8.96 (s, 1H), 7.73 (d, J 9.9, 2H), 6.69 (s, 1H), 2.61 (s, 3H), 1.65-1.56 (m, 1H), 0.95-0.86 (m, 2H), 0.80-0.72 (m, 2H). MS (m/z): 424.09 [M+H]+.

Workup

  1. temperatureThe above mixture was refluxed for 3 hr
  2. customEthanol was removed on rotavapour
  3. customto obtain the crude
  4. customCrude was purified by column on 60-120 mesh silica gel

Sources & evidence

ORD record
ord-9f15460eec2f4c15b8eea1e37a1d1c03
Source dataset
uspto-grants-2014_12
Patent number
US08921364B2

Reaction notes

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