2-Ethylaniline → HCID 58949875, compound

HRID 1641300Notes

Reaction equation

HRID 1641300 reaction equation
[CH2:1]([N:8]1[CH2:26][CH2:25][C:11]2([N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)[C:14](=[O:23])[CH2:13][C:12]2=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:39]([C:41]1[CH:47]=[CH:46][CH:45]=[CH:44][C:42]=1[NH2:43])[CH3:40]>C1(C)C=CC=CC=1.CCOC(C)=O>[CH2:1]([N:8]1[CH2:26][CH2:25][C:11]2([N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)[C:14](=[O:23])[CH:13]=[C:12]2[NH:43][C:42]2[CH:44]=[CH:45][CH:46]=[CH:47][C:41]=2[CH2:39][CH3:40])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 113572-EthylanilineHCID 521998p-Toluenesulfonic acid monohydrateHCID 59252699HCID 59252699, compound

Product 1

HCID 58949875HCID 58949875, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 100 mg (0.28 mmol) 8-benzyl-1-(3-fluorophenyl)-1,8-diazaspiro[4.5]decane-2,4-dione in 0.71 mL dry toluene was added 70 mg (0.37 mmol)p-toluenesulfonic acid monohydrate and 61 μL (0.50 mmol) 2-ethylaniline. The reaction was heated to reflux for 18 h and then diluted with EtOAc, washed with 1N NaOH, dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was purified on silica gel with 20-60% EtOAc/hexanes to afford title example 8-benzyl-4-[(2-ethylphenyl)amino]-1-(3-fluorophenyl)-1,8-diazaspiro[4.5]dec-3-en-2-one as a tan foam. 1H NMR (CD3OD, 400 MHz) δ 7.43 (q, J=7.38 Hz, 1H), 7.32 (m, 1H), 7.24 (m, 6H), 7.16 (m, 3H), 7.08 (m, 2H), 4.55 (s, 1H), 3.41 (s, 2H), 2.80 (m, 2H), 2.64 (q, J=7.51 Hz, 2H), 2.38 (m, 2H), 2.19 (m, 2H), 2.10 (dt, J=11.5 and 3.85 Hz, 2H), 1.18 (t, J=7.51 Hz, 3H); LC/MS [M+H]=456.1.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 18 h
  3. washwashed with 1N NaOH
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified on silica gel with 20-60% EtOAc/hexanes

Sources & evidence

ORD record
ord-b0e47b4a7065472c9f8074ddfc8f9598
Source dataset
uspto-grants-2012_02
Patent number
US08114887B2

Reaction notes

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