Nitrogen → HCID 86650889, compound

HRID 2064974Notes

Reaction equation

HRID 2064974 reaction equation
N#N.[CH3:3][C:4]1([C:9]2[CH:10]=[C:11]([CH2:15][OH:16])[CH:12]=[N:13][CH:14]=2)[O:8][CH2:7][CH2:6][O:5]1.CCN(CC)CC.[S:24](Cl)([CH3:27])(=[O:26])=[O:25]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:3][C:4]1([C:9]2[CH:10]=[C:11]([CH2:15][O:16][S:24]([CH3:27])(=[O:26])=[O:25])[CH:12]=[N:13][CH:14]=2)[O:5][CH2:6][CH2:7][O:8]1

Participants

7

Reactant 4

HCID 947NitrogenHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66928806HCID 66928806, compound

Product 1

HCID 86650889HCID 86650889, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of [5-(2-methyl-[1,3]dioxolan-2-yl)-pyridin-3-yl]-methanol (195 mg, 1.00 mmol) in dry CH2Cl2 (5.0 mL) was treated at 0° C. with Et3N (0.18 mL, 1.29 mmol) followed by DMAP (12 mg, 0.10 mmol) and Ms-Cl (0.10 mL, 1.26 mmol). After stirring at 0° C. for 2 h, the reaction mixture was quenched with water (10 mL), extracted with CH2Cl2 (10 mL) and the combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a pale yellow oil. LC-MS-conditions 02: tR=0.66 min; [M+H]+=274.27.

Workup

  1. customthe reaction mixture was quenched with water (10 mL)
  2. extractionextracted with CH2Cl2 (10 mL)
  3. dry with materialextracts were dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-4b7002845dc2460cb04a43a01283820e
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

Loading…