Potassium Iodide → 2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-9-{1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-azetidin-3-yl}-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene

HRID 1849006Notes

Reaction equation

HRID 1849006 reaction equation
C(N1C(C2SC3CCOC4C=C(C5CN([CH2:27][CH2:28][O:29][CH:30]6[CH2:35][CH2:34][CH2:33][CH2:32][O:31]6)C5)C=CC=4C=3N=2)=NC=N1)(C)C.[NH:36]1[CH2:39][CH:38]([C:40]2[CH:41]=[CH:42][C:43]3[O:52][CH2:51][CH2:50][C:49]4[S:48][C:47]([C:53]5[N:54]([CH:58]([CH3:60])[CH3:59])[N:55]=[CH:56][N:57]=5)=[N:46][C:45]=4[C:44]=3[CH:61]=2)[CH2:37]1.[I-].[K+]>>[CH:58]([N:54]1[C:53]([C:47]2[S:48][C:49]3[CH2:50][CH2:51][O:52][C:43]4[CH:42]=[CH:41][C:40]([CH:38]5[CH2:39][N:36]([CH2:27][CH2:28][O:29][CH:30]6[CH2:35][CH2:34][CH2:33][CH2:32][O:31]6)[CH2:37]5)=[CH:61][C:44]=4[C:45]=3[N:46]=2)=[N:57][CH:56]=[N:55]1)([CH3:59])[CH3:60]

Participants

4

Reactant 3

HCID 4875Potassium IodideHCID 582040952-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-8-{1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-azetidin-3-yl}-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azuleneHCID 670505299-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

Product 1

HCID 582039862-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-9-{1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-azetidin-3-yl}-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azuleneYield 45%

Procedure

The title compound (110 mg, 45%) was prepared by a similar method to 2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-8-{1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-azetidin-3-yl}-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene using 9-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 instead of 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 adding potassium iodide (0.2 eq.) to the reaction mixture. LCMS: RT=3.57 min, [M+H]+=496

Sources & evidence

ORD record
ord-77e59ad33ffd4e32afcf1299d940cc55
Source dataset
uspto-grants-2015_02
Patent number
US08952043B2

Reaction notes

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