Trifluoroacetic acid methylene chloride → {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}-acetic acid TFA salt
Reaction equation
[OH:1][C:2]([C:4]([F:7])([F:6])[F:5])=[O:3].[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.[C:34]([OH:40])([C:36](F)(F)F)=[O:35].C(Cl)Cl>>[OH:3][C:2]([C:4]([F:7])([F:6])[F:5])=[O:1].[CH:29]([N:25]1[C:24]([C:18]2[S:19][C:20]3[CH2:21][CH2:22][O:23][C:14]4[CH:13]=[C:12]([CH:10]5[CH2:11][N:8]([CH2:36][C:34]([OH:40])=[O:35])[CH2:9]5)[CH:33]=[CH:32][C:15]=4[C:16]=3[N:17]=2)=[N:28][CH:27]=[N:26]1)([CH3:31])[CH3:30]Participants
Reactant 2
Product 1
Procedure
Following a similar procedure to 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 using {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}-acetic acid tert-butyl ester and TFA:DCM (1:2), {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}-acetic acid TFA salt was isolated as a white solid (75 mg, 90%). 1H NMR δ (ppm) (DMSO-d6): 8.35 (1H, d, J=8.20 Hz), 8.11 (1H, d, J=0.75 Hz), 7.29 (1H, d, J=8.33 Hz), 7.21 (1H, s), 5.85-5.77 (1H, m), 4.48-4.39 (2H, m), 4.41-4.35 (2H, m), 4.36-4.22 (3H, m), 3.48-3.42 (2H, m), 1.55 (6H, d, J=6.59 Hz) plus 2 protons obscured by the water peak and 2 exchangeable protons not observed.
Sources & evidence
- ORD record
- ord-aaecee6d0fb745238bc783a2a704a6ee
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09175009B2
Reaction notes
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