Triethylamine → HCID 71601388, compound

HRID 2284384Notes

Reaction equation

HRID 2284384 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]([CH3:19])[CH2:10][C:11](=O)[CH2:12][C:13]([O:15]CC)=O)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[Cl-].[CH2:21]([NH:28][NH2:29])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C>CCO>[CH2:21]([N:28]1[C:13](=[O:15])[CH:12]=[C:11]([CH2:10][N:9]([C:4]2[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=2)[CH3:19])[NH:29]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 23004627HCID 23004627, compoundHCID 57382355HCID 57382355, compound

Product 1

HCID 71601388HCID 71601388, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 4-((3,5-dichlorophenyl)(methyl)amino)-3-oxobutanoate (304 mg, 1.0 mmol) and benzyl hydrazine chloride (388 mg, 2.0 mmol) in EtOH (5 mL) was added anhydrous triethylamine (570 uL, 4.0 mmol). The resulting solution was stirred at room temperature overnight. After evaporating the volatiles, the residue was purified on a silica gel column, eluting with a mixture of MeOH and dichloromethane (1% to 2% MeOH) to afford the product as a pale yellow solid (320 mg, 88%). The solid was then recrystallized in dichloromethane/hexane to give the product as a white solid. 1H NMR (DMSO-d6, 500 MHz): δ=11.00 (br s, 1H), 7.28 (t, J=7.0 Hz, 2H), 7.23 (d, J=7.0 Hz, 1H), 7.11 (d, J=7.0 Hz, 2H), 6.74 (d, J=1.5 Hz, 2H), 6.69 (s, 1H), 5.12 (s, 1H), 5.01 (s, 2H), 4.33 (s, 2H), 2.98 (s, 2H); 13C NMR (DMSO-d6, 125 MHz): δ=152.7, 151.0, 146.8, 138.0, 134.4X2, 128.4X2, 127.1, 127.0X2, 114.4, 110.6X2, 84.6, 50.3, 49.2, 38.9 ppm; MS (ESI): m/z 284.0 [M+H]+; CHN calculated for C18H17Cl2N3O: C, 59.68; H, 4.73; N, 11.60. found: C, 59.79; H, 4.68; N, 11.48.

Workup

  1. customAfter evaporating the volatiles
  2. customthe residue was purified on a silica gel column
  3. washeluting with a mixture of MeOH and dichloromethane (1% to 2% MeOH)

Sources & evidence

ORD record
ord-92e3fe59dacb426cb656da5ca75306d1
Source dataset
uspto-grants-2015_09
Patent number
US09145424B2

Reaction notes

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