Pyridine → HCID 86685890, compound
Reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:20]([CH2:27][C:28]([OH:30])=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.ClC(Cl)(Cl)C#N.[NH2:37][C@@:38]([C:53]1[CH:58]=[CH:57][C:56]([O:59][CH2:60][CH2:61][CH2:62][C:63]([F:66])([F:65])[F:64])=[CH:55][CH:54]=1)([C:49]([F:52])([F:51])[F:50])[CH2:39][C:40]([C:42]1[CH:47]=[CH:46][C:45]([CH3:48])=[CH:44][CH:43]=1)=[O:41].N1C=CC=CC=1>C(Cl)Cl>[O:20]([CH2:27][C:28]([NH:37][C@:38]([C:53]1[CH:58]=[CH:57][C:56]([O:59][CH2:60][CH2:61][CH2:62][C:63]([F:64])([F:65])[F:66])=[CH:55][CH:54]=1)([CH2:39][C:40](=[O:41])[C:42]1[CH:43]=[CH:44][C:45]([CH3:48])=[CH:46][CH:47]=1)[C:49]([F:52])([F:51])[F:50])=[O:30])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
To a mixture of triphenylphosphine (138 mg, 0.318 mmol) in dry DCM (0.8 mL) was added 2-phenoxyacetic acid (26 mg, 0.173 mmol), followed by trichloroacetonitrile (30 mg, 0.208 mmol). The mixture was stirred at rt for 2.5 h. To the mixture was added a solution of Intermediate 2F, isomer 2 (30 mg, 0.069 mmol) in dry DCM (0.5 mL) followed by pyridine (17 μL, 0.208 mmol). The reaction was stirred at rt overnight. The mixture was concentrated and purified by preparative HPLC (MeOH/H2O/TFA) to yield the desired product (27 mg, 69%) as a brown oil. LCMS Anal. Calc'd for C29H27F6NO4 567.18, found [M+H] 568.3.
Workup
- stirringThe reaction was stirred at rt overnight
- concentrationThe mixture was concentrated
- custompurified by preparative HPLC (MeOH/H2O/TFA)
Sources & evidence
- ORD record
- ord-eea8db4d142f4237996c100e1579492b
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08791091B2
Reaction notes
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