Bromotrimethylsilane → HCID 66966014, compound

HRID 1515046Notes

Reaction equation

HRID 1515046 reaction equation
C([O:3][P:4]([CH2:9][CH2:10][C:11]1[CH:16]=[C:15]([CH3:17])[C:14]([C:18]2[NH:22][C:21]3[CH:23]=[C:24]([C:27](=[O:39])[NH:28][C:29]4[CH:38]=[CH:37][C:36]5[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=5)[N:30]=4)[CH:25]=[CH:26][C:20]=3[N:19]=2)=[C:13]([CH3:40])[CH:12]=1)(=[O:8])[O:5]CC)C.C[Si](Br)(C)C>C(Cl)Cl>[CH3:40][C:13]1[CH:12]=[C:11]([CH2:10][CH2:9][P:4](=[O:3])([OH:8])[OH:5])[CH:16]=[C:15]([CH3:17])[C:14]=1[C:18]1[NH:22][C:21]2[CH:23]=[C:24]([C:27](=[O:39])[NH:28][C:29]3[CH:38]=[CH:37][C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:30]=3)[CH:25]=[CH:26][C:20]=2[N:19]=1

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 86651278HCID 86651278, compound

Product 1

HCID 66966014HCID 66966014, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-{3,5-dimethyl-4-[6-(quinolin-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-phenyl}-ethyl)-phosphonic acid diethyl ester (270 mg, 0.49 mmol) in CH2Cl2 (10 mL) was added TMSBr (0.64 ml, 4.9 mmol) and the solution was stirred at ambient temperature overnight. The solvent was removed under reduced pressure and the residue was purified by HPLC to give (2-{3,5-dimethyl-4-[6-(quinolin-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-phenyl}-ethyl)-phosphonic acid as a white solid. 1H NMR (Methanol-d4, 400 MHz): δ 8.45 (m, 3H), 8.08 (dd, 1H), 7.94 (m, 2H), 7.81 (dd, 1H), 7.77 (m, 1H), 7.56 (m, 1H), 7.13 (s, 2H), 2.95 (m, 2H), 2.18 (s, 6H), 2.01 (m, 2H). MS (m/z) 501.1 (M+1): Retention time: 1.12 min (Method 10).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-a8f005c9dbb14eac9dd3931a2d252390
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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