Diisopropylethylamine → (1-isopropyl-5-{8-[1-(2-methanesulfonyl-ethyl)-azetidin-3-yl]-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-2-yl}-1H-[1,2,4]triazol-3-yl)-carbamic acid benzyl ester

HRID 707835Notes

Reaction equation

HRID 707835 reaction equation
[CH:1]([N:4]1[C:8]([C:9]2[S:10][C:11]3[CH2:12][CH2:13][O:14][C:15]4[CH:22]=[C:21]([CH:23]5[CH2:26][N:25]([CH2:27][CH2:28][S:29]([CH3:32])(=[O:31])=[O:30])[CH2:24]5)[CH:20]=[CH:19][C:16]=4[C:17]=3[N:18]=2)=[N:7][CH:6]=[N:5]1)([CH3:3])[CH3:2].[OH:33][C:34](C(F)(F)F)=[O:35].N1C[CH:42]([C:44]2[CH:65]=[CH:64][C:47]3C4N=C(C5N(C(C)C)N=CN=5)SC=4CCO[C:46]=3[CH:45]=2)C1.C([N:69](C(C)C)CC)(C)C>C(Cl)Cl.O>[CH2:42]([O:33][C:34](=[O:35])[NH:69][C:6]1[N:7]=[C:8]([C:9]2[S:10][C:11]3[CH2:12][CH2:13][O:14][C:15]4[CH:22]=[C:21]([CH:23]5[CH2:24][N:25]([CH2:27][CH2:28][S:29]([CH3:32])(=[O:30])=[O:31])[CH2:26]5)[CH:20]=[CH:19][C:16]=4[C:17]=3[N:18]=2)[N:4]([CH:1]([CH3:3])[CH3:2])[N:5]=1)[C:44]1[CH:65]=[CH:64][CH:47]=[CH:46][CH:45]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 582040292-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-8-[1-(2-methanesulfonyl-ethyl)-azetidin-3-yl]-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azuleneHCID 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 58204177(1-isopropyl-5-{8-[1-(2-methanesulfonyl-ethyl)-azetidin-3-yl]-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-2-yl}-1H-[1,2,4]triazol-3-yl)-carbamic acid benzyl esterYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by a similar procedure to 2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-8-[1-(2-methanesulfonyl-ethyl)-azetidin-3-yl]-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene using 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 235 HCl salt and diisopropylethylamine. The reaction mixture was diluted with DCM and water. The organic phase dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography (SiO2, 0-4% MeOH in DCM) to give (1-Isopropyl-5-{8-[1-(2-methanesulfonyl-ethyl)-azetidin-3-yl]-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-2-yl}-1H-[1,2,4]triazol-3-yl)-carbamic acid benzyl ester (157 mg, 73%). LCMS: RT=3.04 min, [M+H]+=623

Workup

  1. dry with materialThe organic phase dried (Na2SO4)
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by flash chromatography (SiO2, 0-4% MeOH in DCM)

Sources & evidence

ORD record
ord-f21ac54b763048e6b73a182af6acd58c
Source dataset
uspto-grants-2015_11
Patent number
US09175009B2

Reaction notes

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