Acetonitrile → {3-[5-(3,5-dichloro-phenylsulfanyl)-4-isopropyl-1-pyridin-4-ylmethyl-1H-imidazol-2-ylmethoxycarbonylamino]-propyl}-phosphonic acid diethyl ester

HRID 2374218Notes

Reaction equation

HRID 2374218 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][CH2:49][NH2:50])(=[O:46])[O:43][CH2:44][CH3:45])[CH3:40].C([N:54]([CH:57]([CH3:59])C)[CH2:55][CH3:56])(C)C.[CH3:60][C:61]#N>>[CH2:44]([O:43][P:42]([CH2:47][CH2:48][CH2:49][NH:50][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)[CH2:60][C:61]1[CH:56]=[CH:55][N:54]=[CH:57][CH:59]=1)=[O:38])(=[O:46])[O:41][CH2:39][CH3:40])[CH3:45]

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 78113Diethyl (3-aminopropyl)phosphonateHCID 81531DiisopropylethylamineHCID 59853468HCID 59853468, compound

Product 1

HCID 178476907{3-[5-(3,5-dichloro-phenylsulfanyl)-4-isopropyl-1-pyridin-4-ylmethyl-1H-imidazol-2-ylmethoxycarbonylamino]-propyl}-phosphonic acid diethyl esterYield 79%

Procedure

To a solution of carbonate 16 (15 mg, 0.026 mmol) in CH3CN (2 mL) was added diethyl(aminopropyl)phosphonate (16 mg, 0.052 mmol) and diisopropylethylamine (11 μL, 0.065 mmol). 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 {3-[5-(3,5-dichloro-phenylsulfanyl)-4-isopropyl-1-pyridin-4-ylmethyl-1H-imidazol-2-ylmethoxycarbonylamino]-propyl}-phosphonic acid diethyl ester 23 (13 mg, 79%) as a pale yellow oil. 1H NMR (300 MHz, CDCl3) δ 8.44 (d, 2H), 7.04 (t, 1H), 6.80 (d, 2H), 6.68 (d, 2H), 5.26 (s, 2H), 5.18 (s, 2H), 5.08 (bt, 1H), 4.08 (m, 4H), 3.15 (m, 3H), 1.72 (m, 4H), 1.31 (m, 12H). 31P NMR (300 MHz, CDCl3) δ 31.5

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customThe residue was purified by preparative thin layer chromatography (eluting 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-0b272be067204ce5b5075545b42cd8a5
Source dataset
uspto-grants-2008_12
Patent number
US07462608B2

Reaction notes

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