3,4-Diethoxybenzoic acid → HCID 4342325, compound

HRID 1891445Notes

Reaction equation

[NH2:1][C:2]1[S:6]C(C2C=CC(F)=C(C=2)C#N)=[N:4][N:3]=1.[CH2:16]([O:18][C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][C:27]=1[O:28][CH2:29][CH3:30])[C:22](O)=O)[CH3:17]>>[CH2:16]([O:18][C:19]1[CH:20]=[C:21]([C:22]2[S:6][C:2]([NH2:1])=[N:3][N:4]=2)[CH:25]=[CH:26][C:27]=1[O:28][CH2:29][CH3:30])[CH3:17]

Participants

Reactant 2

HCID 794173,4-Diethoxybenzoic acid

HCID 58367173HCID 58367173, compound

Product 1

HCID 4342325HCID 4342325, compound

Procedure

5-(3,4-Diethoxyphenyl)-1,3,4-thiadiazol-2-amine TDZ INT-2 was synthesized in a similar manner as 5-(5-amino-1,3,4-thiadiazol-2-yl)-2-fluorobenzonitrile TDZ INT-1 using 3,4-diethoxybenzoic acid. LCMS-ESI (m/z) calculated for C12H15N3O2S: 265.3; found 266.1. [M+H]+, tR=2.58 min. 1H NMR (400 MHz, DMSO) δ 7.45-7.31 (m, 1H), 7.23 (dd, J=8.3, 2.1 Hz, 1H), 7.06 (d, J=8.4 Hz, 1H), 4.31-3.94 (m, 4H), 3.4 (s, 2H), 1.42 (qd, J=6.8, 3.3 Hz, 6H).

Sources & evidence

ORD record: ord-0b18afa3063f4b4aab0a4f4dfbc188b9
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507538B2

Reaction notes

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