N,N-dimethylethene-1-sulfonamide → 2-{3-[2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-yl]-azetidin-1-yl}-ethanesulfonic acid dimethylamide

HRID 708184Notes

Reaction equation

HRID 708184 reaction equation
OC(C(F)(F)F)=O.[NH:8]1[CH2:11][CH:10]([C:12]2[CH:33]=[CH:32][C:15]3[C:16]4[N:17]=[C:18]([C:24]5[N:25]([CH:29]([CH3:31])[CH3:30])[N:26]=[CH:27][N:28]=5)[S:19][C:20]=4[CH2:21][CH2:22][O:23][C:14]=3[CH:13]=2)[CH2:9]1.[CH3:34][N:35]([CH3:41])[S:36]([CH:39]=[CH2:40])(=[O:38])=[O:37]>>[CH3:34][N:35]([CH3:41])[S:36]([CH2:39][CH2:40][N:8]1[CH2:11][CH:10]([C:12]2[CH:33]=[CH:32][C:15]3[C:16]4[N:17]=[C:18]([C:24]5[N:25]([CH:29]([CH3:31])[CH3:30])[N:26]=[CH:27][N:28]=5)[S:19][C:20]=4[CH2:21][CH2:22][O:23][C:14]=3[CH:13]=2)[CH2:9]1)(=[O:38])=[O:37]

Participants

3

Reactant 2

HCID 19037148N,N-dimethylethene-1-sulfonamideHCID 866523168-azetidin-3-yl-2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene TFA salt

Product 1

HCID 582038192-{3-[2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-yl]-azetidin-1-yl}-ethanesulfonic acid dimethylamideYield 75%

Procedure

Following the procedure for 320, 8-azetidin-3-yl-2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene TFA salt 235 and ethenesulfonic acid dimethylamide were reacted. The reaction mixture was concentrated in vacuo and the residue partitioned between DCM and water. The organic phase was washed with water followed by brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography (SiO2, 2% MeOH in DCM) to give 443 as a beige solid (117 mg, 75%). LCMS: RT=7.69 min, [M+H]+=503. 1H NMR δ (ppm) (CDCl3): 8.31 (1H, d, J=8.17 Hz), 7.89 (1H, s), 7.08 (1H, dd, J=8.21, 1.86 Hz), 6.99-6.96 (1H, m), 5.92-5.83 (1H, m), 4.38 (2H, t, J=5.05 Hz), 3.77 (2H, t, J=6.90 Hz), 3.74-3.64 (1H, m), 3.39 (2H, t, J=5.06 Hz), 3.23 (2H, t, J=6.67 Hz), 3.00-2.92 (4H, m), 2.87 (6H, s), 1.60 (6H, d, J=6.64 Hz)

Workup

  1. customwere reacted
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue partitioned between DCM and water
  4. washThe organic phase was washed with water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (SiO2, 2% MeOH in DCM)

Sources & evidence

ORD record
ord-5d53130c2eee44d18e1303ca217eccf9
Source dataset
uspto-grants-2015_11
Patent number
US09175009B2

Reaction notes

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