Pyridine → HCID 86685865, compound
Reaction equation
[O:1]=[C:2]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=1)[CH2:3][C:4]([OH:6])=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.ClC(Cl)(Cl)C#N.[NH2:44][C:45]([C:57]1[CH:62]=[CH:61][C:60]([O:63][CH2:64][CH2:65][CH2:66][C:67]([F:70])([F:69])[F:68])=[CH:59][CH:58]=1)([CH3:56])[CH2:46][C:47]([C:49]1[CH:54]=[CH:53][C:52]([CH3:55])=[CH:51][CH:50]=1)=[O:48].N1C=CC=CC=1>C(Cl)Cl>[O:48]=[C:47]([C:49]1[CH:54]=[CH:53][C:52]([CH3:55])=[CH:51][CH:50]=1)[CH2:46][C:45]([NH:44][C:4](=[O:6])[CH2:3][C:2]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=1)=[O:1])([C:57]1[CH:58]=[CH:59][C:60]([O:63][CH2:64][CH2:65][CH2:66][C:67]([F:68])([F:69])[F:70])=[CH:61][CH:62]=1)[CH3:56]Participants
7
Procedure
To a solution of Intermediate 11F (41.6 mg, 0.158 mmol) in anhydrous CH2Cl2 (0.6 mL) was added PPh3 (124 mg, 0.474 mmol) followed by dropwise addition of trichloroacetonitrile (27.4 mg, 0.19 mmol). The reaction was stirred at rt for 3 h. To the freshly prepared acid chloride was added a solution of Intermediate 11E (20 mg, 0.053 mmol) in anhydrous CH2Cl2 (0.3 mL) followed by pyridine (19 mL, 0.237 mmol). The mixture was stirred at rt overnight. The solvent was removed in vacuo. The product was purified by preparative HPLC (MeOH/H2O/TFA) to yield Intermediate 11G (11 mg, 33%) as a brown solid. LCMS Anal. Calc'd for C31H30F6N2O5 624.57, found [M+H] 625.4.
Workup
- stirringThe mixture was stirred at rt overnight
- customThe solvent was removed in vacuo
- customThe product was purified by preparative HPLC (MeOH/H2O/TFA)
Sources & evidence
- ORD record
- ord-65d080c6c46c4460b07834e735b71bc5
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08791091B2
Reaction notes
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