Triethylamine → HCID 45088569, compound

HRID 1170020Notes

Reaction equation

HRID 1170020 reaction equation
FC1C=CC([N+]([O-])=O)=C(C=1)N.[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.CN1C(=O)CCC1>C(Cl)Cl>[CH3:22][N:20]([CH2:19][C@@H:16]1[O:15][CH2:14][C@@H:13]([CH3:12])[NH:18][CH2:17]1)[CH3:21]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 13387N-methyl-2-pyrrolidoneHCID 753995-Fluoro-2-nitroanilineHCID 45088570HCID 45088570, compound

Product 1

HCID 45088569HCID 45088569, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 5-fluoro-2-nitroaniline (1.1 equivalents), [((2S,5R)-5-methylmorpholin-2-yl)methyl]dimethylamine (1 equivalent), triethylamine (3 equivalents), and NMP was heated at 140° C. for 48 hours in a sealed high pressure vessel. The reaction mixture was cooled to 25° C. and dissolved in CH2Cl2. The solution was washed with water (2×) and dried (Na2SO4). Purification via chromatography on silicagel (10% MeOH in dichloromethane), afforded the desired product as a dark yellow foam. LC/MS m/z 295.2 (MH+) Rt 1.86 minutes.

Workup

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

Sources & evidence

ORD record
ord-b095761b7d374ebdb1d2304cace7e63b
Source dataset
uspto-grants-2010_11
Patent number
US07825132B2

Reaction notes

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