Triethylamine → HCID 58955142, compound

HRID 1992518Notes

Reaction equation

HRID 1992518 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[N:13]1[CH2:17][CH2:16][CH:15]([OH:18])[CH2:14]1.C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[N:13]1[CH2:17][CH2:16][CH:15]([O:18][S:27]([CH3:26])(=[O:29])=[O:28])[CH2:14]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58955133HCID 58955133, compound

Product 1

HCID 58955142HCID 58955142, compoundYield 69.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1-(6-Methoxy-[1,5]naphthyridin-4-yl)-pyrrolidin-3-ol (7.67 g, 31.3 mmole), triethylamine (8.73 mL, 63 mmole) and catalytic amount of 4-dimethylaminopyridine dissolved in DCM (100 mL) and cooled to 0° C. The solution was degassed with argon. Methanesulfonyl chloride (2.9 mL, 37.6 mmole) was added dropwise over 30 minutes. The reaction was stirred under argon for 30 minutes at 0° C. and then stirred at room temperature for 1 h. The reaction mixture was concentrated in vacuo. The residue was purified on column chromatography (silica, 1-5% MeOH in chloroform). The solvent was removed in vacuo to afford the title compound as a white solid (7.0 g, 69%): LC-MS (ES) m/z 324 (M+H)+.

Workup

  1. customThe solution was degassed with argon
  2. stirringstirred at room temperature for 1 h
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customThe residue was purified on column chromatography (silica, 1-5% MeOH in chloroform)
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-a6b2338fdda449b48913410c9fc5518d
Source dataset
uspto-grants-2010_01
Patent number
US07648984B2

Reaction notes

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