Triethylamine → HCID 69673091, compound

HRID 705361Notes

Reaction equation

HRID 705361 reaction equation
Cl.[CH:2]1([C:5]2[CH:10]=[CH:9][N:8]=[CH:7][C:6]=2[NH2:11])[CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21].CO.C(Cl)Cl>C(Cl)Cl>[CH:2]1([C:5]2[CH:10]=[CH:9][N:8]=[CH:7][C:6]=2[N:11]([S:20]([CH3:19])(=[O:22])=[O:21])[S:20]([CH3:19])(=[O:22])=[O:21])[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 21226129Dichloromethane methanolHCID 67981736HCID 67981736, compound

Product 1

HCID 69673091HCID 69673091, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of 4-cyclopropylpyridin-3-amine hydrochloride (297 mg, 1.741 mmol) in anhydrous CH2Cl2 (8.5 mL) was cooled to 0° C. and treated with triethylamine (0.849 mL, 6.09 mmol) and methanesulfonyl chloride (0.298 mL, 3.83 mmol). The mixture was stirred at 0° C. for 1 hour, then at room temperature for 1 hour. TLC (SiO2, 5% methanol/CH2Cl2; used sample of free base 10036010-0967 as starting material reference) showed the reaction was complete. The mixture was diluted with CH2Cl2 (50 mL), washed with saturated aqueous NaHCO3 (25 mL), dried over anhydrous Na2SO4, filtered, and concentrated by rotary evaporation to give a tan solid. The solid was purified by SiO2 flash chromatography (3.8 cm×10 cm) eluting with 3% methanol/CH2Cl2 to afford the product as a white solid (403 mg).

Workup

  1. waitat room temperature for 1 hour
  2. washwashed with saturated aqueous NaHCO3 (25 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation
  6. customto give a tan solid
  7. customThe solid was purified by SiO2 flash chromatography (3.8 cm×10 cm)
  8. washeluting with 3% methanol/CH2Cl2

Sources & evidence

ORD record
ord-70e9d92f1f3246f496786700823fc819
Source dataset
uspto-grants-2015_11
Patent number
US09173887B2

Reaction notes

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