Methanesulfonyl chloride → HCID 59541865, compound

HRID 2388310Notes

Reaction equation

HRID 2388310 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]3[C:16]([NH2:17])=[CH:15][CH:14]=[CH:13][N:12]=3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>ClCCl.N1C=CC=CC=1>[O:4]1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]3[C:16]([NH:17][S:19]([CH3:18])(=[O:21])=[O:20])=[CH:15][CH:14]=[CH:13][N:12]=3)[CH2:7][CH2:6]2)[O:1][CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 66750762HCID 66750762, compound

Product 1

HCID 59541865HCID 59541865, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

2-(1,4-Dioxa-spiro[4.5]dec-8-yl)-pyridin-3-ylamine (0.141 g, 0.603 mmol, prepared as described in Example 3: Steps A-B from 3-amino-2-bromopyridine) was dissolved in anhydrous dichloromethane (10 mL) under Ar, treated with methanesulfonyl chloride (0.155 mL, 1.48 mmol), a few drops of anhydrous pyridine, and stirred at ambient temperature for 24 h. The reaction was quenched with saturated aqueous NaHCO3, the aqueous layer extracted thrice with dichloromethane, and the combined organic layers washed with brine, dried over Na2SO4, filtered, and the filtrate concentrated in vacuo giving the title compound as a very hygroscopic yellow solid. ESI-MS (m/z): Calcd. For C14H20N2O4S: 312. found: 313 (M+H)

Workup

  1. customThe reaction was quenched with saturated aqueous NaHCO3
  2. extractionthe aqueous layer extracted thrice with dichloromethane
  3. washthe combined organic layers washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-20786ead312847ed99ea71195345dc99
Source dataset
uspto-grants-2012_09
Patent number
US08269015B2

Reaction notes

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