Acetonitrile → HCID 178476920, compound
Reaction equation
[N+](C1C=CC(O[C:11](=[O:38])[O:12][CH2:13][C:14]2[N:15](CC3C=CN=CC=3)[C:16]([S:22][C:23]3[CH:28]=[C:27]([Cl:29])[CH:26]=[C:25]([Cl:30])[CH:24]=3)=[C:17]([CH:19]([CH3:21])[CH3:20])[N:18]=2)=CC=1)([O-])=O.[CH2:39]([O:41][P:42]([CH2:47][NH2:48])(=[O:46])[O:43][CH2:44][CH3:45])[CH3:40].C([N:52]([CH:55]([CH3:57])C)[CH2:53][CH3:54])(C)C.[CH3:58][C:59]#N>>[CH2:39]([O:41][P:42]([CH2:47][NH:48][C:11]([O:12][CH:13]([C:14]1[NH:15][C:16]([S:22][C:23]2[CH:24]=[C:25]([Cl:30])[CH:26]=[C:27]([Cl:29])[CH:28]=2)=[C:17]([CH:19]([CH3:20])[CH3:21])[N:18]=1)[CH2:58][C:59]1[CH:54]=[CH:53][N:52]=[CH:55][CH:57]=1)=[O:38])(=[O:46])[O:43][CH2:44][CH3:45])[CH3:40]Participants
Procedure
To a solution of carbonate 16 (14 mg, 0.024 mmol) in CH3CN (2 mL) was added diethyl(aminomethyl)phosphonate (10 mg, 0.037 mmol) and diisopropylethylamine (8 μL, 0.048 mmol). See Scheme 18 (FIG. 20). After the reaction mixture was stirred for 16 h at room temperature, the mixture was concentrated under reduced pressure. The residue was purified by preparative thin layer chromatography (eluting 5% MeOH/CH2Cl2) to give {[5-(3,5-dichloro-phenylsulfanyl)-4-isopropyl-1-pyridin-4-ylmethyl-1H-imidazol-2-ylmethoxycarbonylamino]-methyl}-phosphonic acid diethyl ester 17 (13 mg, 90%) as a pale yellow oil. 1H NMR (300 MHz, CDCl3) δ 8.44 (d, 2H), 7.04 (t, 1H), 6.78 (d, 2H), 6.68 (d, 2H), 5.25 (s, 2H), 5.19 (s, 2H), 4.98 (bt, 1H), 4.11 (dq, 4H), 3.49 (ABq, 2H), 3.17 (dq, 1H), 1.30 (m, 12H). 31P NMR (300 MHz, CDCl3) δ 21.9.
Workup
- concentrationthe mixture was concentrated under reduced pressure
- customThe residue was purified by preparative thin layer chromatography (eluting 5% MeOH/CH2Cl2)
Sources & evidence
- ORD record
- ord-ab2f75b08789425ebc2e7b6477cf388d
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07462608B2
Reaction notes
Loading…