Ethanesulfonyl chloride → HCID 49819734, compound

HRID 1623563Notes

Reaction equation

HRID 1623563 reaction equation
[CH2:1]([S:3](Cl)(=[O:5])=[O:4])[CH3:2].[NH2:7][C:8]1[CH:9]=[C:10]([C:14]2[CH:24]=[CH:23][C:17]3[N:18]([CH3:22])[C:19](=[O:21])[S:20][C:16]=3[CH:15]=2)[CH:11]=[N:12][CH:13]=1>N1C=CC=CC=1>[CH3:22][N:18]1[C:17]2[CH:23]=[CH:24][C:14]([C:10]3[CH:9]=[C:8]([NH:7][S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])[CH:13]=[N:12][CH:11]=3)=[CH:15][C:16]=2[S:20][C:19]1=[O:21]

Participants

4

Reactant 2

HCID 11667Ethanesulfonyl chlorideHCID 49819733HCID 49819733, compound

Product 1

HCID 49819734HCID 49819734, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

General sulfonylation procedure: EtSO2Cl (51.4 mg, 0.4 mmol) was added dropwise to a solution of 6-(5-aminopyridin-3-yl)-3-methylbenzo[d]thiazol-2(3H)-one (Example 50: 28 mg, 0.1 mmol) in pyridine (2 mL) at 0° C. The resulting mixture was slowly warmed up to room temperature and stirred for additional 3 hrs at this temperature. After concentration, the residue was purified by flash column (MeOH/CH2Cl2, v/v, 1-3%) and yielded yellow solid (20 mg), MS (ESI) m/z 350.4 (M±H)+. 1H NMR (400 MHz, MeOD) δ ppm 1.35 (t, J=7.4 Hz, 3H), 3.22 (q, J=7.4 Hz, 2H), 3.51 (q, 3H), 7.38 (d, J=8 Hz, 1H), 7.68 (d, J=8 Hz, 1H), 7.87 (s, 1H), 7.95 (s, 1H), 8.40 (s, 1H), 8.58 (s, 1H).

Workup

  1. concentrationAfter concentration
  2. customthe residue was purified by flash column (MeOH/CH2Cl2, v/v, 1-3%)

Sources & evidence

ORD record
ord-36550489306a416fb0f397eed680ed3d
Source dataset
uspto-grants-2014_07
Patent number
US08778972B2

Reaction notes

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