Formamidine acetate → HCID 51353438, compound

HRID 1408561Notes

Reaction equation

HRID 1408561 reaction equation
[CH:1]1([C:4]2[N:8]([C:9]3[N:14]=[CH:13][C:12]([NH:15][C:16](=[O:25])[C:17](=[CH:21][N:22](C)[CH3:23])[C:18](=O)[CH3:19])=[CH:11][N:10]=3)[N:7]=[C:6]([C:26]([F:29])([F:28])[F:27])[CH:5]=2)[CH2:3][CH2:2]1.C(O)(=O)C.C(N)=[NH:35].CC[O-].[Na+]>C(O)C>[CH:1]1([C:4]2[N:8]([C:9]3[N:10]=[CH:11][C:12]([NH:15][C:16]([C:17]4[C:18]([CH3:19])=[N:35][CH:23]=[N:22][CH:21]=4)=[O:25])=[CH:13][N:14]=3)[N:7]=[C:6]([C:26]([F:27])([F:28])[F:29])[CH:5]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 160693Formamidine acetateHCID 2723922Sodium ethoxideHCID 86652979HCID 86652979, compound

Product 1

HCID 51353438HCID 51353438, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-{2-[5-cyclopropyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]pyrimidin-5-yl}-2-[(dimethylamino)methylene]-3-oxobutanamide (0.3 g, 0.78 mmol) and formamidine acetate (98 mg, 0.94 mmol) were dissolved in ethanol and added NaOEt (60 mg, 0.94 mmol). The above mixture was refluxed for 3 h. 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 (1:1) as eluent to obtain the title compound (12 mg) as a brown solid. M.P.: 201-203° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 11.29 (s, 1H), 9.26 (s, 2H), 9.19 (s, 1H), 8.99 (s, 1H), 6.68 (s, 1H), 2.64 (s, 3H), 2.55-2.49 (m, 1H), 1.02-0.94 (m, 2H), 0.83-0.75 (m, 2H). MS (m/z): 389.93 [M+H]+.

Workup

  1. temperatureThe above mixture was refluxed for 3 h
  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-160684e6506a4aaabe42e83aa5958a8a
Source dataset
uspto-grants-2014_12
Patent number
US08921364B2

Reaction notes

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