1-(2-Hydroxyethyl)piperazine → HCID 10225806, compound

HRID 1822840Notes

Reaction equation

HRID 1822840 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.CCOC(/N=N/C(OCC)=O)=O.[CH2:41]([C:43]1[CH:65]=[CH:64][CH:63]=[CH:62][C:44]=1[NH:45][C:46]1[C:55]2[C:50](=[CH:51][C:52](O)=[C:53]([O:56][CH3:57])[CH:54]=2)[N:49]=[CH:48][C:47]=1[C:59]([NH2:61])=[O:60])[CH3:42]>C(Cl)Cl.C1COCC1>[CH2:41]([C:43]1[CH:65]=[CH:64][CH:63]=[CH:62][C:44]=1[NH:45][C:46]1[C:55]2[C:50](=[CH:51][C:52]([O:20][CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)=[C:53]([O:56][CH3:57])[CH:54]=2)[N:49]=[CH:48][C:47]=1[C:59]([NH2:61])=[O:60])[CH3:42]

Participants

7

Reactant 4

HCID 76771-(2-Hydroxyethyl)piperazineHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 135788285HCID 135788285, compound

Product 1

HCID 10225806HCID 10225806, compoundYield 50.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Triphenylphosphine (0.12 g, 0.44 mmol) and 1-(2-hydroxyethyl)piperazine (25 μl, 0.22 mmol) was dissloved in CH2Cl2 and THF at −15° C. and stirred for 30 min. DEAD (70 μl, 0.44 mmol) was added dropwise at −15° C. 4-(2-ethylanilino)-7-hydroxy-6-methoxy-3-quinolinecarboxamide (0.50 g, 0.15 mmol) was suspended in THF and then added to the reaction. The reaction was stirred over night, allowing the temperature rise to ˜10° C. The solvent was removed under reduced pressure and the product was purified using preparative HPLC affording 34 mg (24%) of a clear oil.

Workup

  1. additionadded to the reaction
  2. customto ˜10° C
  3. customThe solvent was removed under reduced pressure
  4. customthe product was purified

Sources & evidence

ORD record
ord-56184d12e0604e1f9f5c9d862cfe4287
Source dataset
uspto-grants-2006_05
Patent number
US07037925B2

Reaction notes

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