Dichloromethane → N-[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-yl]4'-cyanobiphenyl-4-sulfonamide

HRID 2374462Notes

Reaction equation

HRID 2374462 reaction equation
ClCCl.[Si:4]([O:11][CH2:12][C:13]1[N:18]=[C:17]([NH2:19])[CH:16]=[CH:15][CH:14]=1)([C:7]([CH3:10])([CH3:9])[CH3:8])([CH3:6])[CH3:5].[C:20]([C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=2)=[CH:24][CH:23]=1)#[N:21]>N1C=CC=CC=1>[Si:4]([O:11][CH2:12][C:13]1[N:18]=[C:17]([NH:19][S:34]([C:31]2[CH:30]=[CH:29][C:28]([C:25]3[CH:26]=[CH:27][C:22]([C:20]#[N:21])=[CH:23][CH:24]=3)=[CH:33][CH:32]=2)(=[O:36])=[O:35])[CH:16]=[CH:15][CH:14]=1)([C:7]([CH3:10])([CH3:9])[CH3:8])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 211322306-({[Tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amineHCID 233602874-(4-Cyanophenyl)benzenesulfonyl chloride

Product 1

HCID 58838520N-[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-yl]4'-cyanobiphenyl-4-sulfonamideYield 76%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of dichloromethane (3 mL) was added 6-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine (0.15 g, 0.63 mmol), 4′-cyanobiphenyl4-sulfonyl chloride (0.18 g, 0.63 mmol) and pyridine (1.0 mL). The mixture was stirred for 3 hours then was washed with saturated sodium bicarbonate (2×30 mL) and aqueous hydrochloric acid (2×30 mL, 0.1 N). The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. Purification was done using silica gel chromatography eluting with hexane: ethyl acetate (1:1) and combined fractions were concentrated to afford the above-titled intermediate as a white solid (0.21 g, 76%). HPLC: Rt4.236 min. (81% area). 1H NMR (400 MHz, CDCl3), δ: 7.89 (d, J=8.3 Hz, 2H), 7.60 (d, J=8.3 Hz, 2H), 7.52-7.49 (m, 4H), 7.43 (t, J=7.6 Hz, 1H), 6.87 (d, J=8.6 Hz, 1H), 6.59 (d, J=7.3Hz, 1H), 6.22 (d, J=8.0 Hz, 1H), 4.55 (s, 2H), 0.82 (s, 9H), 0.05 (s, 6H); LRMS (ESI): m/z: 480.1.

Workup

  1. washthen was washed with saturated sodium bicarbonate (2×30 mL) and aqueous hydrochloric acid (2×30 mL, 0.1 N)
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification
  6. washeluting with hexane: ethyl acetate (1:1)
  7. concentrationwere concentrated

Sources & evidence

ORD record
ord-221203798f354c61aa7e4cf94d6fed85
Source dataset
uspto-grants-2008_12
Patent number
US07462634B2

Reaction notes

Loading…