Acetic Acid → HCID 86705035, compound
Reaction equation
F[P-](F)(F)(F)(F)F.[CH2:8](C1N=NN(O[P+](N(C)C)(N(C)C)N(C)C)C=1)[C:9]1C=CC=CC=1.[Cl:31][C:32]1[CH:37]=[CH:36][C:35]([C@:38]([N:46]2[C:54]3[C:49](=[C:50]([NH:55][S:56]([CH3:59])(=[O:58])=[O:57])[CH:51]=[CH:52][CH:53]=3)[CH:48]=[CH:47]2)([CH2:44][CH3:45])/[C:39](=[N:42]\[H])/[NH:40][OH:41])=[CH:34][CH:33]=1.[C:60](O)(=O)C.C(N(CC)C(C)C)(C)C>C(#N)C.O>[CH3:60][CH2:59][S:56]([NH:55][C:50]1[CH:51]=[CH:52][CH:53]=[C:54]2[C:49]=1[CH:48]=[CH:47][N:46]2[C@:38]([C:35]1[CH:36]=[CH:37][C:32]([Cl:31])=[CH:33][CH:34]=1)([C:39]1[N:42]=[C:8]([CH3:9])[O:41][N:40]=1)[CH2:44][CH3:45])(=[O:58])=[O:57]Participants
7
Procedure
(Benzyltriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (37 mg, 0.083 mmol) was added to a mixture of 5b (35 mg, 0.083 mmol), acetic acid (4.8 μL, 0.083 mmol) and N,N-diisopropylethylamine (29 μL, 0.166 mmol) in acetonitrile (1.50 mL). The resulting mixture was stirred at rt for 30 sec, then heated in a microwave reactor at 150° C. for 20 min. After cooling to rt, the reaction mixture was diluted with water, and the mixture was purified by preparative reversed phase HPLC on YMC Pack Pro C18 stationary phase (CH3CN/H2O as eluent, 0.05% TFA as modifier), followed by lyophilization of the purified fractions to afford the title compound 57. m/z (ES) 445 (MH)+; IP=A rating
Workup
- temperatureheated in a microwave reactor at 150° C. for 20 min
- temperatureAfter cooling to rt
- customthe mixture was purified by preparative reversed phase HPLC on YMC Pack Pro C18 stationary phase (CH3CN/H2O as eluent, 0.05% TFA as modifier)
Sources & evidence
- ORD record
- ord-974b20f529024b8ebc080f77458109e7
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09403807B2
Reaction notes
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