Triphenylphosphine → HCID 59743158, compound

HRID 1366800Notes

Reaction equation

C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([OH:23])(=[S:22])[CH3:21].[Cl:24][C:25]1[CH:30]=[C:29]([CH3:31])[C:28]([NH:32][C:33]([C:35]2[N:36]([C:44]3[C:49]([Cl:50])=[CH:48][CH:47]=[CH:46][N:45]=3)[N:37]=[C:38]([C:40]([F:43])([F:42])[F:41])[CH:39]=2)=[O:34])=[C:27]([C:51](=[O:57])[NH:52][CH2:53][CH:54](O)[CH3:55])[CH:26]=1>C1COCC1>[Cl:24][C:25]1[CH:30]=[C:29]([CH3:31])[C:28]([NH:32][C:33]([C:35]2[N:36]([C:44]3[C:49]([Cl:50])=[CH:48][CH:47]=[CH:46][N:45]=3)[N:37]=[C:38]([C:40]([F:41])([F:43])[F:42])[CH:39]=2)=[O:34])=[C:27]([CH:26]=1)[C:51]([NH:52][CH2:53][CH:54]([S:22][C:20](=[O:23])[CH3:21])[CH3:55])=[O:57]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2.55 g (9.7 mmol) triphenylphosphine in 250 ml THF is added at a temperature of 0° C. 2.25 g (9.7 mmol) diterbutylazodicarboxylate in 25 ml THF. The solution is stirred for 1 hour at a temperature of 0° C. Then 0.35 ml (4.85 mmol) thioacetic acid is added and a white suspension is formed immediately. After that, a solution of 2.5 g (4.85 mmol) 2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid [4-chloro-2-(2-hydroxy-propylcarbamoyl)-6-methyl-phenyl]-amide in 30 ml THF is slowly added at a temperature of 0° C. The solution is stirred for 1 hour at a temperature of 0° C., and then 15 hours at 25° C., and then evaporated. The residue is submitted to flash-chromatography (ethyl acetate 1, hexane 2) to give 2.45 g (88%) white crystals (m.p. 137-139° C.).

Workup

customa white suspension is formed immediately
stirringThe solution is stirred for 1 hour at a temperature of 0° C.
custom15 hours at 25° C., and then evaporated

Sources & evidence

ORD record: ord-824116a346f049c6862836e3fa0e2444
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07893092B2

Reaction notes

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