Diisopropyl azodicarboxylate → Cyclopropyl-[2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulen-8-yloxy]-acetic acid methyl ester

HRID 1629546Notes

Reaction equation

HRID 1629546 reaction equation
[CH:1]([N:4]1[C:8]([C:9]2[N:10]=[C:11]3[C:17]4[CH:18]=[CH:19][C:20]([OH:22])=[CH:21][C:16]=4[O:15][CH2:14][CH2:13][N:12]3[CH:23]=2)=[N:7][CH:6]=[N:5]1)([CH3:3])[CH3:2].[CH3:24][O:25][C:26](=[O:32])[CH:27]([CH:29]1[CH2:31][CH2:30]1)O.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCOCC1>[CH3:24][O:25][C:26](=[O:32])[CH:27]([CH:29]1[CH2:31][CH2:30]1)[O:22][C:20]1[CH:19]=[CH:18][C:17]2[C:11]3[N:12]([CH2:13][CH2:14][O:15][C:16]=2[CH:21]=1)[CH:23]=[C:9]([C:8]1[N:4]([CH:1]([CH3:3])[CH3:2])[N:5]=[CH:6][N:7]=1)[N:10]=3

Participants

5

Reactant 3

HCID 5363146Diisopropyl azodicarboxylateHCID 11073449Methyl cyclopropyl(hydroxy)acetateHCID 1360309202-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulen-8-ol

Product 1

HCID 58204945Cyclopropyl-[2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulen-8-yloxy]-acetic acid methyl esterYield 25.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulen-8-ol 490 (0.20 g, 0.64 mmol), cyclopropyl-hydroxy-acetic acid methyl ester (0.253 g, 1.28 mmol), triphenylphopshine (0.205 g, 1.28 mmol) and DIAD (252 μL, 1.28 mmol) in dioxane (6 mL) was stirred at RT for 18 h then concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 0 to 10% methanol in TBME) to give Cyclopropyl-[2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulen-8-yloxy]-acetic acid methyl ester (0.068 g, 25%). LCMS: RT=3.43 min, [M+H]+=424.

Workup

  1. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-e79961f55ff74bbaa956f19d29c5af25
Source dataset
uspto-grants-2014_07
Patent number
US08785626B2

Reaction notes

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