Trimethylsilyl iodide → HCID 178523840, compound

HRID 1497327Notes

Reaction equation

HRID 1497327 reaction equation
[OH:1][C@@H:2]1[C@@H:7]([NH:8][C:9]([C:11]2[CH:20]=[C:19]([CH2:21][C:22]3[CH:23]=[N:24][C:25]([O:28]C)=[CH:26][CH:27]=3)[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]=2)=[O:10])[CH2:6][CH2:5][O:4][CH2:3]1.C[Si](I)(C)C>C(Cl)Cl>[OH:28][C:25]1[N:24]=[CH:23][C:22]([CH2:21][C:19]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]=[C:11]([C:9]([NH:8][C@H:7]3[CH2:6][CH2:5][O:4][CH2:3][C@@H:2]3[OH:1])=[O:10])[CH:20]=2)=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 53307628HCID 53307628, compound

Product 1

HCID 178523840HCID 178523840, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of N-[(3R,4S)-3-Hydroxytetrahydro-2H-pyran-4-yl]-4-[(6-methoxypyridin-3-yl)methyl]quinoline-2-carboxamide (0.15 g, 0.38 mmol) in CH2Cl2 was added trimethylsilyl iodide (0.15 mL, 1.1 mmol). The reaction mixture was heated to 50° C. for 16 h and cooled to room temperature and concentrated. The resultant residue was subjected to silica gel chromatography eluting with 0-15% methanol in methylene chloride to afford 4-[(6-hydroxypyridin-3-yl)methyl]-N-[(3R,4S)-3-hydroxytetrahydro-2H-pyran-4-yl]quinoline-2-carboxamide (L1) that gave a mass ion (ES+) of 380.4 for M+H+.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated
  3. washeluting with 0-15% methanol in methylene chloride

Sources & evidence

ORD record
ord-9029c5a627dc4999b15d980882fe61bd
Source dataset
uspto-grants-2015_12
Patent number
US09199939B2

Reaction notes

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