Bromotrimethylsilane → (3-{3,5-Dimethyl-4-[6-(quinolin-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-phenyl}-propyl)-phosphonic acid monoethyl ester

HRID 1515050Notes

Reaction equation

HRID 1515050 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[C:16]([CH3:18])[C:15]([C:19]2[NH:23][C:22]3[CH:24]=[C:25]([C:28](=[O:40])[NH:29][C:30]4[CH:39]=[CH:38][C:37]5[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=5)[N:31]=4)[CH:26]=[CH:27][C:21]=3[N:20]=2)=[C:14]([CH3:41])[CH:13]=1)(=[O:8])[O:5]CC)[CH3:2].C[Si](Br)(C)C>C(Cl)Cl>[CH2:1]([O:3][P:4]([CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[C:16]([CH3:18])[C:15]([C:19]2[NH:23][C:22]3[CH:24]=[C:25]([C:28](=[O:40])[NH:29][C:30]4[CH:39]=[CH:38][C:37]5[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=5)[N:31]=4)[CH:26]=[CH:27][C:21]=3[N:20]=2)=[C:14]([CH3:41])[CH:13]=1)(=[O:5])[OH:8])[CH3:2]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 86651280(3-{3,5-Dimethyl-4-[6-(quinolin-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-phenyl}-propyl)-phosphonic acid diethyl ester

Product 1

HCID 86651281(3-{3,5-Dimethyl-4-[6-(quinolin-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-phenyl}-propyl)-phosphonic acid monoethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-{3,5-dimethyl-4-[6-(quinolin-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-phenyl}-propyl)-phosphonic acid diethyl ester (40 mg, 0.07 mmol) in CH2Cl2 (5 mL) was added TMSBr (0.045 mL, 0.35 mol). The solution was stirred at ambient temperature until monohydrolysis occurred (5 h). The solvent was removed under reduced pressure and the residue was purified by HPLC to give the title compound as a white solid. 1H NMR (Methanol-d4, 400 MHz): δ 8.41 (m, 3H), 8.08 (dd, 1H), 7.94 (dd, 2H), 7.81 (d, 1H), 7.77 (m, 1H), 7.56 (m, 1H), 7.10 (s, 2H), 3.97 (m, 2H), 2.75 (t, 2H), 2.18 (s, 6H), 1.97 (m, 2H), 1.68 (m, 2H), 1.29 (t, 3H). MS (m/z) 543.2 (M+1); Retention time: 1.17 min (method 10).

Workup

  1. custom(5 h)
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-9ffec97287be4d77a0878799732ec6df
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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