5-Diethylaminomethyl-4-methyl-thiophene-2-carboxylic acid → 2-Chloro-4-[5-(5-diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenylamine

HRID 1685777Notes

Reaction equation

HRID 1685777 reaction equation
[CH2:1]([N:3]([CH2:6][C:7]1[S:11][C:10]([C:12]([OH:14])=O)=[CH:9][C:8]=1[CH3:15])[CH2:4][CH3:5])[CH3:2].[NH2:16][C:17]1[C:26]([CH3:27])=[CH:25][C:20]([C:21]([NH:23]O)=[NH:22])=[CH:19][C:18]=1[Cl:28]>>[Cl:28][C:18]1[CH:19]=[C:20]([C:21]2[N:23]=[C:12]([C:10]3[S:11][C:7]([CH2:6][N:3]([CH2:1][CH3:2])[CH2:4][CH3:5])=[C:8]([CH3:15])[CH:9]=3)[O:14][N:22]=2)[CH:25]=[C:26]([CH3:27])[C:17]=1[NH2:16]

Participants

3

Reactant 2

HCID 672654805-Diethylaminomethyl-4-methyl-thiophene-2-carboxylic acidHCID 178426663HCID 178426663, compound

Product 1

HCID 672658962-Chloro-4-[5-(5-diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenylamineYield 11.6%

Procedure

The title compound (20 mg) is prepared starting from 5-diethylaminomethyl-4-methyl-thiophene-2-carboxylic acid (100 mg, 440 μmol) and 4-amino-3-chloro-N-hydroxy-5-methyl-benzamidine (97 mg, 484 μmol) according to Method A; LC-MS: tR=0.61 min; [M+1]+=391.08; 1H NMR (CDCl3): δ1.11 (t, J=7.0 Hz, 6H), 2.25 (s, 3H), 2.29 (s, 3H), 2.57-2.70 (m, 4H), 3.72 (s, 2H), 7.65 (s, 1H), 7.78 (s, 1H), 7.98 (d, J=1.5 Hz, 1H).

Sources & evidence

ORD record
ord-f4e2c5d1b8f4484e9e2d9061f60187cc
Source dataset
uspto-grants-2012_04
Patent number
US08148410B2

Reaction notes

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