3-Ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylic acid → 4-[5-(3-Ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-[1,3,4]oxadiazol-2-yl]-2,6-dimethyl-pyridine

HRID 2366133Notes

Reaction equation

HRID 2366133 reaction equation
[CH2:1]([C:3]1[S:7][C:6]([C:8]([OH:10])=O)=[C:5]2[CH2:11][CH2:12][C:13]([CH3:16])([CH3:15])[CH2:14][C:4]=12)[CH3:2].Cl.[CH3:18][C:19]1[CH:20]=[C:21]([CH:26]=[C:27]([CH3:29])[N:28]=1)[C:22]([NH:24][NH2:25])=O>>[CH2:1]([C:3]1[S:7][C:6]([C:8]2[O:10][C:22]([C:21]3[CH:26]=[C:27]([CH3:29])[N:28]=[C:19]([CH3:18])[CH:20]=3)=[N:24][N:25]=2)=[C:5]2[CH2:11][CH2:12][C:13]([CH3:16])([CH3:15])[CH2:14][C:4]=12)[CH3:2]

Participants

3

Reactant 2

HCID 574374183-Ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylic acidHCID 670271882,6-Dimethyl-isonicotinic acid hydrazide hydrochloride

Product 1

HCID 248757424-[5-(3-Ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-[1,3,4]oxadiazol-2-yl]-2,6-dimethyl-pyridine

Procedure

4-[5-(3-Ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-[1,3,4]oxadiazol-2-yl]-2,6-dimethyl-pyridine is synthesized from 3-ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylic acid and 2,6-dimethyl-isonicotinic acid hydrazide hydrochloride in analogy to Example 9; LC-MS: tR=0.93 min, [M+1]=368.44; 1H NMR (CD3OD): δ 7.66 (s, 2 H), 3.09 (t, J=6.7 Hz, 2 H), 2.80 (q, J=7.6 Hz, 2 H), 2.60 (s, 6 H), 2.39 (s, 2 H), 1.67 (t, J=6.7 Hz, 2 H), 1.29 (t, J=7.6 Hz, 3 H), 1.03 (s, 6 H).

Sources & evidence

ORD record
ord-4c41b99b4a974e828f90cbc7a4795f24
Source dataset
uspto-grants-2014_04
Patent number
US08697732B2

Reaction notes

Loading…