2-Nitrophenol → HCID 10133802, compound

HRID 1272035Notes

Reaction equation

HRID 1272035 reaction equation
[N+](C1C=CC=CC=1O)([O-])=O.[CH3:11][O:12][C:13]1[CH:25]=[CH:24][C:16]([C:17]([CH2:19][CH2:20][C:21]([OH:23])=O)=[O:18])=[CH:15][C:14]=1[F:26].CC(C)N=C=NC(C)C.[N:36]1[CH:41]=[CH:40][C:39]([N:42]2[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]2)=[CH:38][CH:37]=1>ClCC(Cl)C.CN(C=O)C.C(N(CC)CC)C>[F:26][C:14]1[CH:15]=[C:16]([C:17](=[O:18])[CH2:19][CH2:20][C:21]([N:45]2[CH2:46][CH2:47][N:42]([C:39]3[CH:40]=[CH:41][N:36]=[CH:37][CH:38]=3)[CH2:43][CH2:44]2)=[O:23])[CH:24]=[CH:25][C:13]=1[O:12][CH3:11]

Participants

8

Reactant 4

HCID 69472-NitrophenolHCID 12734DiisopropylcarbodiimideHCID 676713-(3-Fluoro-4-methoxybenzoyl)propionic acidHCID 705171-(4-Pyridyl)piperazine

Product 1

HCID 10133802HCID 10133802, compoundYield 718.3%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 65641,2-DichloropropaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

To the polymeric nitrophenol (1.5 g, approx. 1 mmol) was added a solution of 3-(4-methoxy-3-fluorobenzoyl)propionic acid (1.66 g, 7.34 mmol) in a mixture of 1,2-dichloropropane (15 ml) and DMF (6 ml), followed by the addition of DIC (0.78 ml, 5.01 mmol). The mixture was shaken at room temperature for 13 hours, filtered, and the polymer was extensively washed with DCM, DMF, and 1,2-dichloropropane. To the polymer was added 1,2-dichloropropane (5 ml), a solution of 1-(4-pyridyl)piperazine (116 mg, 0.71 mmol) in 1,2-dichloropropane (10 ml), and triethylamine (0.2 ml). The resulting mixture was shaken at room temperature for 21 hours, filtered, and the polymer was carefully washed with DCM and methanol. The combined filtrates were concentrated to yield the crude product as an oil (0.38 g). Crystallization from acetonitrile (2 ml) at −20° C. yielded 0.19 g (5.1 mmol, 72%) of the title compound as almost colourless solid.

Workup

  1. filtrationfiltered
  2. washthe polymer was extensively washed with DCM, DMF, and 1,2-dichloropropane
  3. additionTo the polymer was added 1,2-dichloropropane (5 ml)
  4. stirringThe resulting mixture was shaken at room temperature for 21 hours
  5. filtrationfiltered
  6. washthe polymer was carefully washed with DCM and methanol
  7. concentrationThe combined filtrates were concentrated
  8. customto yield the crude product as an oil (0.38 g)
  9. customCrystallization from acetonitrile (2 ml) at −20° C.

Sources & evidence

ORD record
ord-1f5f074e7d7d47c2a3273200454902ae
Source dataset
uspto-grants-2007_04
Patent number
US07208497B2

Reaction notes

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