Acetonitrile → HCID 178476909, 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][CH2:48][NH2:49])(=[O:46])[O:43][CH2:44][CH3:45])[CH3:40].C([N:53]([CH:56]([CH3:58])C)[CH2:54][CH3:55])(C)C.[CH3:59][C:60]#N>>[CH2:44]([O:43][P:42]([CH2:47][CH2:48][NH:49][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)[CH2:59][C:60]1[CH:55]=[CH:54][N:53]=[CH:56][CH:58]=1)=[O:38])(=[O:46])[O:41][CH2:39][CH3:40])[CH3:45]Participants
Procedure
To a solution of carbonate 16 (82 mg, 0.143 mmol) in CH3CN (5 mL) was added diethyl(aminoethyl)phosphonate (58 mg, 0.214 mmol) and diisopropylethylamine (0.05 mL, 0.286 mmol). See Scheme 20 (FIG. 22). After the reaction mixture was stirred for 16 h at room temperature, the mixture was concentrated under reduced pressure. The residue was chromatographed on silica gel (eluting 5-7.5% MeOH/CH2Cl2) to give {2-[5-(3,5-Dichloro-phenylsulfanyl)-4-isopropyl-1-pyridin-4-ylmethyl-1H-imidazol-2-ylmethoxycarbonylamino]-ethyl}-phosphonic acid diethyl ester 18 (79 mg, 90%) as a pale yellow oil. 1H NMR (300 MHz, CDCl3) δ 8.43 (d, 2H), 7.02 (s, 1H), 6.77 (d, 2H), 6.67 (s, 2H), 5.32 (t, 1H), 5.24 (s, 2H), 5.16 (s, 2H), 4.08 (m, 4H), 3.35 (m, 2H), 3.15 (m, 1H), 1.86 (m, 2H), 1.30 (m, 6H), 1.29 (s, 6H). 31P NMR (300 MHz, CDCl3) δ 31.5.
Workup
- concentrationthe mixture was concentrated under reduced pressure
- customThe residue was chromatographed on silica gel (eluting 5-7.5% MeOH/CH2Cl2)
Sources & evidence
- ORD record
- ord-01c5317e95504611bef20819a0153f70
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07462608B2
Reaction notes
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