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}-2-methyl-propionitrile → 2-{4-[2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-yl]-piperidin-1-yl}-2-methyl-propionitrile
Reaction equation
C(N1C(C2SC3CCO[C:15]4C=C(C5CN(C(C)(C)C#N)C5)C=[CH:19][C:16]=4[C:17]=3[N:18]=2)=NC=N1)(C)C.OC(C(F)(F)F)=O.[CH:39]([N:42]1[C:46]([C:47]2[S:48][C:49]3[CH2:50][CH2:51][O:52][C:53]4[CH:60]=[C:59]([CH:61]5[CH2:66][CH2:65][NH:64][CH2:63][CH2:62]5)[CH:58]=[CH:57][C:54]=4[C:55]=3[N:56]=2)=[N:45][CH:44]=[N:43]1)([CH3:41])[CH3:40]>>[CH:39]([N:42]1[C:46]([C:47]2[S:48][C:49]3[CH2:50][CH2:51][O:52][C:53]4[CH:60]=[C:59]([CH:61]5[CH2:66][CH2:65][N:64]([C:16]([CH3:19])([CH3:15])[C:17]#[N:18])[CH2:63][CH2:62]5)[CH:58]=[CH:57][C:54]=4[C:55]=3[N:56]=2)=[N:45][CH:44]=[N:43]1)([CH3:41])[CH3:40]Participants
3
Reactant 2
Product 1
Procedure
The title compound was prepared by a similar procedure to 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}-2-methyl-propionitrile using 2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-8-piperidin-4-yl-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene TFA salt to give 2-{4-[2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-yl]-piperidin-1-yl}-2-methyl-propionitrile isolated as an orange oil (346 mg) as a roughly 1:1 mixture with 2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-8-piperidin-4-yl-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene and was used without further purification. LCMS: RT=4.71 min, [M+H]+=463
Sources & evidence
- ORD record
- ord-2c71d416b524484f9295a5b325b3d8fa
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09175009B2
Reaction notes
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