1,2-Dichloroethane → HCID 67459030, compound

HRID 1804467Notes

Reaction equation

[CH:1]1([C:4]2[C:5]([C:15]([OH:17])=O)=[N:6][O:7][C:8]=2[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:3][CH2:2]1.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.C(Cl)CCl.O/[N:42]=[C:43](/[C:45]1[CH:62]=[CH:61][C:48]([CH2:49][N:50]2[CH2:53][CH:52]([C:54]([O:56][C:57]([CH3:60])([CH3:59])[CH3:58])=[O:55])[CH2:51]2)=[CH:47][CH:46]=1)\[NH2:44]>C(#N)C>[CH:1]1([C:4]2[C:5]([C:15]3[O:17][N:44]=[C:43]([C:45]4[CH:46]=[CH:47][C:48]([CH2:49][N:50]5[CH2:51][CH:52]([C:54]([O:56][C:57]([CH3:58])([CH3:60])[CH3:59])=[O:55])[CH2:53]5)=[CH:61][CH:62]=4)[N:42]=3)=[N:6][O:7][C:8]=2[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-cyclopropyl-5-phenylisoxazole-3-carboxylic acid (22 mg, 0.096 mmol), HOBt (26.5 mg, 0.173 mmol), and diisopropylethylamine (0.067 mL, 0.384 mmol) in acetonitrile (1 mL) was added EDC (43.2 mg, 0.226 mmol) and (Z)-tert-butyl 1-(4-(N′-hydroxycarbamimidoyl)benzyl)azetidine-3-carboxylate (Int.1, 29.3 mg, 0.096 mmol). The reaction mixture was stirred at 80° C. for 2 h. The reaction mixture was concentrated, and the residue was purified by preparative HPLC to give tert-butyl 1-(4-(5-(4-cyclopropyl-5-phenylisoxazol-3-yl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylate.

Workup

concentrationThe reaction mixture was concentrated
customthe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-27226305fc14453097cfe8daca3d1cf8
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354398B2

Reaction notes

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