Triphenylphosphine → HCID 10137059, compound

HRID 1822839Notes

Reaction equation

HRID 1822839 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:20][N:21]([CH3:26])[CH2:22][CH2:23][CH2:24][OH:25].CCOC(/N=N/C(OCC)=O)=O.[CH2:39]([C:41]1[CH:63]=[CH:62][CH:61]=[CH:60][C:42]=1[NH:43][C:44]1[C:53]2[C:48](=[CH:49][C:50]([O:55][CH3:56])=[C:51](O)[CH:52]=2)[N:47]=[CH:46][C:45]=1[C:57]([NH2:59])=[O:58])[CH3:40]>C(Cl)Cl.C1COCC1>[CH3:20][N:21]([CH3:26])[CH2:22][CH2:23][CH2:24][O:25][C:51]1[CH:52]=[C:53]2[C:48](=[CH:49][C:50]=1[O:55][CH3:56])[N:47]=[CH:46][C:45]([C:57]([NH2:59])=[O:58])=[C:44]2[NH:43][C:42]1[CH:60]=[CH:61][CH:62]=[CH:63][C:41]=1[CH2:39][CH3:40]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 766463-(Dimethylamino)-1-propanolHCID 5462977Diethyl azodicarboxylateHCID 22170327HCID 22170327, compound

Product 1

HCID 10137059HCID 10137059, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Polymer-bound Triphenylphosphine (0.15 g, 0.44 mmol) and 3-dimethylamino-1-propanol (26 μl, 0.22 mmol) was suspended and 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)-6-hydroxy-7-methoxy-3-quinolinecarboxamide (50 mg, 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 polymer was filtered off and the filtrate concentrated in vacuo. The product was purified using preparative HPLC according 15 mg (24%) of white crystals.

Workup

  1. additionadded to the reaction
  2. customto ˜10° C
  3. filtrationThe polymer was filtered off
  4. concentrationthe filtrate concentrated in vacuo
  5. customThe product was purified

Sources & evidence

ORD record
ord-5345b481562d4ab6b03680404d268b14
Source dataset
uspto-grants-2006_05
Patent number
US07037925B2

Reaction notes

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