Triethylamine → HCID 58650614, compound

HRID 1830006Notes

Reaction equation

HRID 1830006 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].[CH3:12][C@@H:13]1[NH:18][CH2:17][C@@H:16]([CH2:19][N:20]([CH3:22])[CH3:21])[O:15][CH2:14]1.C(N(CC)CC)C.CN1CCCC1=O>C(Cl)Cl>[NH2:7][C:6]1[CH:8]=[C:2]([N:18]2[C@@H:13]([CH3:12])[CH2:14][O:15][C@H:16]([CH2:19][N:20]([CH3:21])[CH3:22])[CH2:17]2)[CH:3]=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 13387N-methyl-2-pyrrolidoneHCID 753995-Fluoro-2-nitroanilineHCID 58650608HCID 58650608, compound

Product 1

HCID 58650614HCID 58650614, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 5-fluoro-2-nitroaniline (1.1 equivalents), [((2S,5S)-5-methylmorpholin-2-yl)methyl]dimethylamine (1 equivalent), triethylamine (3 equivalents), and N-methylpyrrolidinone was heated at 140° C. for 48 hours in a sealed high pressure vessel. The reaction mixture was then cooled to 25° C. and dissolved in CH2Cl2. The solution was washed with water (×2) and dried over Na2SO4. Purification via chromatography on silica gel (10% MeOH in dichloromethane) afforded the desired product as a dark yellow foam. LC/MS (m/z) 295.2 (MH+) Rt 1.55 minutes.

Workup

  1. temperatureThe reaction mixture was then cooled to 25° C.
  2. washThe solution was washed with water (×2)
  3. dry with materialdried over Na2SO4
  4. customPurification via chromatography on silica gel (10% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-0a5a3bfdb8654bb886d8b1abb7ca6a13
Source dataset
uspto-grants-2006_06
Patent number
US07064215B2

Reaction notes

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