Methanol → HCID 69702067, compound

HRID 925189Notes

Reaction equation

HRID 925189 reaction equation
C(OC([N:6]1[CH2:19][CH2:18][C:10]2[C:11]3[CH2:12][CH2:13][CH2:14][C:15]=3[CH:16]=[CH:17][C:9]=2[CH2:8][CH2:7]1)=O)C.[Si](I)(C)(C)C.CO>C(Cl)(Cl)Cl>[CH2:12]1[C:11]2[C:10]3[CH2:18][CH2:19][NH:6][CH2:7][CH2:8][C:9]=3[CH:17]=[CH:16][C:15]=2[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 887MethanolHCID 85247Trimethylsilyl iodideHCID 90272380HCID 90272380, compound

Product 1

HCID 69702067HCID 69702067, compoundYield 63.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

Into a glass vial, the product from step (a) (0.126 mmol) in CHCl3 (3 ml) was placed. To this stirred solution, TMSI (172 μL, 1.26 mmol) was added. The reaction mixture was heated to 60° C. for 3 h. The reaction mixture was allowed to cool to room temperature and methanol (1 ml) was added to quench. The solvent was evaporated in vacuo to give the crude product as a yellow residue. The crude product was purified by semi-prep RP-HPLC to give the title compound as light yellow oil (15 mg). Recovered as acetate salt: 1H NMR (CDCl3) δ 7.18 (bs, 2H), 7.02 (d, J=7.2 Hz, 1H), 6.92 (d, J=7.2 Hz, 1H), 3.15-3.05 (m, 8H), 2.94-2.84 (m, 4H), 2.12-2.02 (m, 2H) 1.98 (s, 3H); MS: ESI (positive): 188 (M+H).

Workup

  1. temperatureto cool to room temperature
  2. customto quench
  3. customThe solvent was evaporated in vacuo
  4. customto give the crude product as a yellow residue
  5. customThe crude product was purified by semi-prep RP-HPLC

Sources & evidence

ORD record
ord-dbfc0af1a8214606943703dea21f3989
Source dataset
uspto-grants-2016_03
Patent number
US09284277B2

Reaction notes

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