Bromotrimethylsilane → HCID 178445784, compound

HRID 2404107Notes

Reaction equation

HRID 2404107 reaction equation
C([O:3][P:4]([CH2:9][CH2:10][NH:11][CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([O:23][CH:24]3[CH2:29][CH2:28][CH:27]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:26][CH2:25]3)[CH:19]=2)[CH:14]=1)(=[O:8])[O:5]CC)C.Br[Si](C)(C)C>C(#N)C>[C:30]([C@H:27]1[CH2:26][CH2:25][C@H:24]([O:23][C:18]2[CH:19]=[C:20]3[C:15](=[CH:16][CH:17]=2)[CH:14]=[C:13]([CH2:12][NH:11][CH2:10][CH2:9][P:4](=[O:3])([OH:8])[OH:5])[CH:22]=[CH:21]3)[CH2:29][CH2:28]1)([CH3:33])([CH3:31])[CH3:32]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 86668415HCID 86668415, compound

Product 1

HCID 178445784HCID 178445784, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (2-{[6-(4-tert-butyl-cyclohexyloxy)-naphthalen-2-ylmethyl]-amino}-ethyl)-phosphonic acid diethyl ester (65.00 mg, 0.14 mmol) in acetonitrile (1 mL) was added bromotrimethylsilane (1 mL, 7.58 mmol). The reaction was then stirred at 50° C. overnight. After the solvent was concentrated, the residue was purified with HPLC (acetonitrile-water, 15-85%) to give white precipitate (33 mg, yield: 58). ESI-MS: 420.2 (M+H)+; 1H NMR (400 MHz, DMSO) δ=7.81-7.91 (m, 3H), 7.51 (dd, 1H), 7.41 (d, 1H), 7.19 (dd, 1H), 4.40 (m, 1H), 4.31 (s, 2H), 3.12 (m, 2H), 2.21 (d, 2H), 1.97 (m, 2H), 1.82 (d, 2H), 1.36 (q, 2H), 1.22 (q, 2H), 1.08 (m, 1H), 0.88 (s, 9H).

Workup

  1. concentrationAfter the solvent was concentrated
  2. customthe residue was purified with HPLC (acetonitrile-water, 15-85%)
  3. customto give white precipitate (33 mg, yield: 58)

Sources & evidence

ORD record
ord-968d3ff06c934b558ae85d2535e0a508
Source dataset
uspto-grants-2014_08
Patent number
US08802659B2

Reaction notes

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