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 1190294Notes

Reaction equation

HRID 1190294 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-d47a4a88519047b3b233094be4440c72
Source dataset
uspto-grants-2014_03
Patent number
US08673952B2

Reaction notes

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