1,2-Dichloroethane → HCID 57554627, compound

HRID 1511884Notes

Reaction equation

[CH2:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].C(Cl)CCl.C1C=C2N=NN(O)C2=CC=1.O.O/[N:30]=[C:31](\[NH2:50])/[C:32]1[CH:37]=[CH:36][C:35]([C@H:38]2[CH2:49][CH2:48][C:40]3([NH:44][C:43](=[O:45])[N:42]([CH3:46])[C:41]3=[O:47])[CH2:39]2)=[CH:34][CH:33]=1>CN(C=O)C>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:9]2[O:11][N:30]=[C:31]([C:32]3[CH:33]=[CH:34][C:35]([C@H:38]4[CH2:49][CH2:48][C:40]5([NH:44][C:43](=[O:45])[N:42]([CH3:46])[C:41]5=[O:47])[CH2:39]4)=[CH:36][CH:37]=3)[N:50]=2)=[CH:12][CH:13]=1)[CH:2]([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 140 °C

Procedure

A solution of 4-isobutylbenzoic acid (0.130 g, 0.728 mmol), EDC (0.139 g, 0.728 mmol) and HOBt hydrate (0.111 g, 0.728 mmol) in DMF (1.0 ml) was stirred at ambient temperature for 1-1.5 hours. To the mixture was added (Z)-N′-hydroxy-4-{(7S)-3-methyl-2,4-dioxo-1,3-diazaspiro[4.4]nonan-7-yl}benzimidamide (0.200 g, 0.662 mmol) as solution in 1.0 ml DMF at ambient temperature. The resulting mixture was heated to about 140° C. for additional 2 hours. Solvent was removed in vacuo. The crude product was purified on a Prep HPLC system using 20-99% 50 mM NH4OAc buffer in acetonitrile at 81 mL/min to afford (7S)-7-(4-(5-(4-isobutylphenyl)-1,2,4-oxadiazol-3-yl)phenyl)-3-methyl-1,3-diazaspiro[4.4]nonane-2,4-dione (0.062 g, 0.139 mmol) as light brown solid.

Workup

customSolvent was removed in vacuo
customThe crude product was purified on a Prep HPLC system

Sources & evidence

ORD record: ord-79899c124ea14178becc0536396429df
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217027B2

Reaction notes

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