Ethanesulfonyl chloride → n-(1-(5-(3-Chloro-4-cyanophenyl)pyridin-3-yl)cyclopropyl)ethanesulfonamide

HRID 391329Notes

Reaction equation

HRID 391329 reaction equation
[NH2:1][C:2]1([C:5]2[CH:6]=[C:7]([C:11]3[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[C:13]([Cl:19])[CH:12]=3)[CH:8]=[N:9][CH:10]=2)[CH2:4][CH2:3]1.[CH2:20]([S:22](Cl)(=[O:24])=[O:23])[CH3:21]>C(Cl)Cl>[Cl:19][C:13]1[CH:12]=[C:11]([C:7]2[CH:6]=[C:5]([C:2]3([NH:1][S:22]([CH2:20][CH3:21])(=[O:24])=[O:23])[CH2:3][CH2:4]3)[CH:10]=[N:9][CH:8]=2)[CH:18]=[CH:17][C:14]=1[C:15]#[N:16]

Participants

4

Reactant 2

HCID 11667Ethanesulfonyl chlorideHCID 595784184-(5-(1-Aminocyclopropyl)pyridin-3-yl)-2-chlorobenzonitrile

Product 1

HCID 49821054n-(1-(5-(3-Chloro-4-cyanophenyl)pyridin-3-yl)cyclopropyl)ethanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(5-(1-aminocyclopropyl)pyridin-3-yl)-2-chlorobenzonitrile (70 mg, 0.26 mmol) in DCM (3 mL) at room temperature was added TEA (0.109 mL, 0.779 mmol) and EtSO2Cl (74 μL, 0.779 mmol) dropwise, and the mixture was stirred at room temperature for 1 h. The mixture was concentrated in vacuo, re-dissolved in DMF (3 mL) and filtered. The filtrate was purified by Xbridge Phenyl followed by Xbridge C18 eluting with 20-80% ACN-water gradient to give N-(1-(5-(3-chloro-4-cyanophenyl)pyridin-3-yl)cyclopropyl)ethanesulfonamide. HRMS: (ESI) m/z 362.0712 [(M+H)+ Calcd for C17H96ClN3O2S 362.0725]. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.28 (t, J=7.3 Hz, 3H), 1.32-1.38 (m, 2H), 1.49-1.54 (m, 2H), 2.90 (q, J=7.4 Hz, 2H), 7.60 (dd, J=8.1, 1.8 Hz, 1H), 7.74 (d, J=1.8 Hz, 1H), 7.79 (d, J=8.1 Hz, 1H), 8.01 (t, J=2.3 Hz, 1H), 8.67 (d, J=2.3 Hz, 1H), 8.72 (d, J=2.3 Hz, 1H).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionre-dissolved in DMF (3 mL)
  3. filtrationfiltered
  4. customThe filtrate was purified by Xbridge Phenyl
  5. washC18 eluting with 20-80% ACN-water gradient

Sources & evidence

ORD record
ord-7f9b3cdcdc864dc08d6ef48ad3cbb43c
Source dataset
uspto-grants-2013_02
Patent number
US08383827B2

Reaction notes

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