1-Ethenesulfonyl-3,3-difluoro-azetidine → 8-{1-[2-(3,3-Difluoro-azetidine-1-sulfonyl)-ethyl]-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

HRID 708197Notes

Reaction equation

HRID 708197 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.[CH:34]([S:36]([N:39]1[CH2:42][C:41]([F:44])([F:43])[CH2:40]1)(=[O:38])=[O:37])=[CH2:35]>>[F:44][C:41]1([F:43])[CH2:40][N:39]([S:36]([CH2:34][CH2:35][N:8]2[CH2:11][CH:10]([C:12]3[CH:33]=[CH:32][C:15]4[C:16]5[N:17]=[C:18]([C:24]6[N:25]([CH:29]([CH3:31])[CH3:30])[N:26]=[CH:27][N:28]=6)[S:19][C:20]=5[CH2:21][CH2:22][O:23][C:14]=4[CH:13]=3)[CH2:9]2)(=[O:37])=[O:38])[CH2:42]1

Participants

3

Reactant 2

HCID 582041541-Ethenesulfonyl-3,3-difluoro-azetidineHCID 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 582042758-{1-[2-(3,3-Difluoro-azetidine-1-sulfonyl)-ethyl]-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

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 1-ethenesulfonyl-3,3-difluoro-azetidine were reacted to give 454 isolated as a white solid (139 mg, 84%). LCMS: RT=8.30 min, [M+H]+=551. 1H NMR δ (ppm) (CDCl3): 8.32 (1H, d, J=8.18 Hz), 7.89 (1H, s), 7.08 (1H, dd, J=8.21, 1.87 Hz), 6.97 (1H, d, J=1.84 Hz), 5.93-5.83 (1H, m), 4.38 (2H, t, J=5.05 Hz), 4.31 (4H, t, J=12.10 Hz), 3.76 (2H, t, J=6.86 Hz), 3.75-3.63 (1H, m), 3.43-3.36 (2H, m), 3.23 (2H, t, J=6.61 Hz), 3.11 (2H, t, J=7.01 Hz), 2.92 (2H, t, J=7.00 Hz), 1.60 (6H, d, J=6.63 Hz)

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-af46f08d71384b049600d39a94c1ea10
Source dataset
uspto-grants-2015_11
Patent number
US09175009B2

Reaction notes

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