Methylhydrazine → 3-cyclopropyl-[1,2,4]oxadiazol-5-ylmethyl-N,N-dimethyl-formamidine

HRID 351824

Reaction equation

[CH:1]1([C:4]2[N:8]=[C:7]([CH2:9]N3C(=O)C4=CC=CC=C4C3=O)[O:6][N:5]=2)[CH2:3][CH2:2]1.C1C=C2C(N(CC(O)=O)C(=O)C2=CC=1)=O.C1(C(=NO)N)CC1.CNN.[NH2:46][CH2:47][N:48]1[CH2:52]ON=[C:49]1C1CC1>CN(C=O)C.C(N1C=CN=C1)(N1C=CN=C1)=O.ClCCCl>[CH:1]1([C:4]2[N:8]=[C:7]([CH2:9][C:47]([N:48]([CH3:52])[CH3:49])=[NH:46])[O:6][N:5]=2)[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 130 °C

Procedure

Scheme 3 describes the preparation of known starting materials. The processes for preparation of these compounds are also known or may be carried out in analogous manner to known methods. For example, N-[(3-cyclopropyl-1,2,4-oxadiazol-5-yl)methyl]phthalimide is prepared by reaction of N-phthaloylglycine in DMF and 1,1′carbonyldiimidazole, and followed by the addition of cyclopropanecarboxamidoxime. The obtained N-[(3-cyclopropyl-1,2,4-oxadiazol-5-yl)methyl]phthalimide is then dissolved in 1,2-dichloroethane and N-methylhydrazine is added. The obtained 4-(aminomethyl)-3-cyclopropyl-1,2,4-oxadiazole is then treated with N,N-dimethylformaldehyde diethyl acetal and heated at about 130° C. and the desired starting material (E/Z)-N′-(3-cyclopropyl-[1,2,4]oxadiazol-5-ylmethyl-N,N-dimethyl-formamidine is obtained.

Workup

customthe preparation
customThe processes for preparation of these compounds

Sources & evidence

ORD record: ord-72e9f2e9c5ca4a129d217bbf2e0400c1
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06743789B2

Linked notes

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