5-Diethylaminomethyl-4-methyl-thiophene-2-carboxylic acid → HCID 136377329, compound

HRID 1685782Notes

Reaction equation

HRID 1685782 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].[OH:16][C:17]1[C:26]([CH3:27])=[CH:25][C:20]([C:21]([NH:23]O)=[NH:22])=[CH:19][C:18]=1[CH2:28][CH2:29][CH3:30]>>[CH2:4]([N:3]([CH2:6][C:7]1[S:11][C:10]([C:12]2[O:14][N:23]=[C:21]([C:20]3[CH:19]=[C:18]([CH2:28][CH2:29][CH3:30])[C:17]([OH:16])=[C:26]([CH3:27])[CH:25]=3)[N:22]=2)=[CH:9][C:8]=1[CH3:15])[CH2:1][CH3:2])[CH3:5]

Participants

3

Reactant 2

HCID 672654805-Diethylaminomethyl-4-methyl-thiophene-2-carboxylic acidHCID 178439252HCID 178439252, compound

Product 1

HCID 136377329HCID 136377329, compoundYield 42.8%

Procedure

The title compound (20 mg) is prepared starting from 5-diethylaminomethyl-4-methyl-thiophene-2-carboxylic acid (30 mg, 130 μmol) and 4,N-dihydroxy-3-propyl-5-methyl-benzamidine (24 mg, 117 μmol) according to Method A; LC-MS: tR=0.64 min; [M+1]+=400.22; 1H NMR (D6-DMSO): δ0.94 (t, J=7.3 Hz, 3H), 1.03 (t, J=7.0 Hz, 6H), 1.53-1.64 (m, 2H), 2.22 (s, 3H), 2.26 (s, 2H), 2.57 (q, J=7.0 Hz, 4H), 2.61-2.66 (m, 2H), 3.73 (s, 2H), 7.59-7.62 (m, 1H), 7.62-7.65 (m, 1H), 7.78 (s, 1H), 8.88 (s br, 1H).

Sources & evidence

ORD record
ord-3e71d9d8e0544757a8061462ce0a042e
Source dataset
uspto-grants-2012_04
Patent number
US08148410B2

Reaction notes

Loading…