Hydrochloric Acid → HCID 68608115, compound

HRID 1991141Notes

Reaction equation

HRID 1991141 reaction equation
[CH3:1][N:2]1[CH2:6][C:5]([C:7]2[C:15]3[C:10](=[N:11][CH:12]=[C:13]([CH2:16][CH:17]4[CH2:22][CH2:21][C:20](=[O:23])[CH2:19][CH2:18]4)[CH:14]=3)[N:9](COCC[Si](C)(C)C)[CH:8]=2)=[CH:4][NH:3]1.Cl>CCO>[CH3:1][N:2]1[CH2:6][C:5]([C:7]2[C:15]3[C:10](=[N:11][CH:12]=[C:13]([CH2:16][CH:17]4[CH2:22][CH2:21][C:20](=[O:23])[CH2:19][CH2:18]4)[CH:14]=3)[NH:9][CH:8]=2)=[CH:4][NH:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68610704HCID 68610704, compound

Product 1

HCID 68608115HCID 68608115, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 88 (19 mg, 42 μmol) in EtOH (1 mL) was added 10% aq. HCl (1 mL) and the reaction mixture heated to reflux (bath temperature 90° C.) for 18 h. The solution was then concentrated and the residue purified by preparative LCMS (column LUNA 10 μ C18(2) 00G-4253-V0 250×50 mm) using water—acetonitrile (0.1% AcOH) as eluent (in gradient; flow 80 mL/min) to afford 91 (8 mg, 26 μmol, 62%) as a white powder. 1H NMR (400 MHz, CDCl3) δ 1.49-1.63 (m, 2H), 2.04-2.19 (m, 3H), 2.31-2.50 (m, 4H), 2.92 (d, J=6.9 Hz, 2H), 4.06 (s, 3H), 7.67 (s, 1H), 7.68 (s, 1H), 7.85 (s, 1H), 8.24 (s, 1H), 8.38 (s, 1H), 12.35 (br s, 1H). MS (CI) m/z 309 (MH+).

Workup

  1. temperaturethe reaction mixture heated
  2. concentrationThe solution was then concentrated
  3. customthe residue purified by preparative LCMS (column LUNA 10 μ C18(2) 00G-4253-V0 250×50 mm)

Sources & evidence

ORD record
ord-e6fbfde08e914516bf19e0a58eb98d58
Source dataset
uspto-grants-2010_01
Patent number
US07645769B2

Reaction notes

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