Triphenylphosphine → 3-{2-[4-(4-Chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-6-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-3H-benzooxazol-2-one

HRID 1710655Notes

Reaction equation

C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O.[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([N:39]2[CH2:44][CH2:43][N:42]([C:45](=[O:58])[CH2:46][N:47]3[C:51]4[CH:52]=[CH:53][C:54]([OH:56])=[CH:55][C:50]=4[O:49][C:48]3=[O:57])[CH2:41][CH2:40]2)=[CH:35][C:34]=1[O:59][CH3:60].[O:61]1[CH2:66][CH2:65][CH2:64][CH2:63][CH:62]1[O:67][CH2:68][CH2:69]O>C1COCC1>[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([N:39]2[CH2:40][CH2:41][N:42]([C:45](=[O:58])[CH2:46][N:47]3[C:51]4[CH:52]=[CH:53][C:54]([O:56][CH2:69][CH2:68][O:67][CH:62]5[CH2:63][CH2:64][CH2:65][CH2:66][O:61]5)=[CH:55][C:50]=4[O:49][C:48]3=[O:57])[CH2:43][CH2:44]2)=[CH:35][C:34]=1[O:59][CH3:60]

Participants

Conditions

Temperature: 85 °C

Procedure

To a mixture of PPh3 (70 mg, 0.27 mmol, 1.1 eq), and DEAD (40 mg, 0.23 mmol, 1 eq) in THF (0.5 ml), was added 3-{2-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-6-hydroxy-3H-benzooxazol-2-one (54) (100 mg, 0.24 mmol, 1 eq) in THF (1 ml). The reaction mixture immediately turned clear and was heated to 85° C. 2-(Tetrahydro-pyran-2-yloxy)-ethanol (38.5 mg, 0.27 mmol, 1.1 eq), was then added to the reaction solution, and stirred for 3 hours at rt. The isolated crude product was purified with HPLC to provide 3-{2-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-6-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-3H-benzooxazol-2-one (55).

Workup

customThe isolated crude product
customwas purified with HPLC

Sources & evidence

ORD record: ord-7bf78f3bf94d40b19efda7382456a918
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790726B2

Reaction notes

Loading…