Sodium hydride → HCID 58156513, compound

HRID 628830Notes

Reaction equation

HRID 628830 reaction equation
CN(C)[C:3]([CH3:17])=[CH:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1)=O.C([O:23][C:24](=[O:34])[C:25]1[CH:30]=[CH:29][C:28]([C:31](=[NH:33])[NH2:32])=[CH:27][CH:26]=1)(C)(C)C.C(OC(=O)C1C=CC=C(C(=N)N)C=1)(C)(C)C.[H-].[Na+]>C(O)C>[CH3:17][C:3]1[CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:14])([F:15])[F:16])=[CH:9][CH:8]=2)[N:32]=[C:31]([C:28]2[CH:27]=[CH:26][C:25]([C:24]([OH:23])=[O:34])=[CH:30][CH:29]=2)[N:33]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 57094593HCID 57094593, compoundHCID 692346333-Dimethylamino-1-(4-trifluoromethyl-phenyl)-but-2-en-1-oneHCID 69234794HCID 69234794, compound

Product 1

HCID 58156513HCID 58156513, compoundYield 2.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Part B. To a mixture of 3-dimethylamino-1-(4-trifluoromethyl-phenyl)-but-2-en-1-one (290.1 mg, 1.13 mmol), 4-carbamimidoyl-benzoic acid tert-butyl ester (220.3 mg, 1.00 mmol, prepared by the same manner as 3-carbamimidoyl-benzoic acid tert-butyl ester) and sodium hydride (79.9 mg, 2.00 mmol, 60% in hexanes) is added dry ethanol (5.0 mL). The resulting mixture is stirred at refluxing for 14 h until complete consumption of the starting material is determined by TLC. The solvent is removed, and the residue is neutralized with 1N HCl until pH <7 to precipitate a white solid, which is collected by filtration followed by washing with water and ethyl ether/hexanes (1:1). The obtained solid is further purified by flash column chromatography, eluting with methanol/methylene chloride (1:40), to give the title product (10.7 mg, 2.7% yield), m.p. 272-275° C. 1H NMR (300 MHz, CDCl3+2 drops DMSO-d6): δ 8.54 (2H, d, J=8.3 Hz), 8.23 (2H, d, J=8.6 Hz), 8.09 (2H, d, J=8.3 Hz), 7.71 (2H, d, J=8.6 Hz), 7.48 (1H, s), 2.61 (3H, s). MS (ES+): m/e 359.27.

Workup

  1. temperatureat refluxing for 14 h until complete consumption of the starting material
  2. customThe solvent is removed
  3. customto precipitate a white solid, which
  4. filtrationis collected by filtration
  5. washby washing with water and ethyl ether/hexanes (1:1)
  6. customThe obtained solid is further purified by flash column chromatography
  7. washeluting with methanol/methylene chloride (1:40)

Sources & evidence

ORD record
ord-33fc167f10964985bef97ace4419f9de
Source dataset
uspto-grants-2016_04
Patent number
US09315467B2

Reaction notes

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