2-Methylpiperazine → (3-Methyl-piperazin-1-yl)-(4H-thieno[3,2-b]pyrrol-5-yl)-methanone

HRID 1990715Notes

Reaction equation

HRID 1990715 reaction equation
[S:1]1[C:8]2[CH:7]=[C:6]([C:9]([OH:11])=O)[NH:5][C:4]=2[CH:3]=[CH:2]1.[CH3:12][CH:13]1[CH2:18][NH:17][CH2:16][CH2:15][NH:14]1>>[CH3:12][CH:13]1[NH:14][CH2:15][CH2:16][N:17]([C:9]([C:6]2[NH:5][C:4]3[CH:3]=[CH:2][S:1][C:8]=3[CH:7]=2)=[O:11])[CH2:18]1

Participants

3

Reactant 2

HCID 660572-MethylpiperazineHCID 49612544H-thieno(3,2-b)pyrrole-5-carboxylic acid

Product 1

HCID 24737903(3-Methyl-piperazin-1-yl)-(4H-thieno[3,2-b]pyrrol-5-yl)-methanoneYield 78%

Procedure

4H-Thieno[3,2-b]pyrrole-5-carboxylic acid (50 mg, 0.30 mmol) was coupled with 2-methylpiperazine according to Procedure D to provide the title compound (58 mg, 78%) as an off-white solid. TLC (silica, 10% MeOH/CH2Cl2): Rf=0.15. MS (electrospray): exact mass calculated for C12H15N3OS, 249.09; m/z found, 250.1 [M+H]+. 1H NMR (CD3OD, 400 MHz): 7.33 (d, J=5.3 Hz, 1H), 6.98 (d, J=5.3 Hz, 1H), 6.88 (s, 1H), 4.62-4.56 (m, 2H), 3.50-3.20 (m, 5H), 1.36 (d, J=6.6 Hz, 3H).

Sources & evidence

ORD record
ord-2a842f00f20d45cabcd4cc8aa9aa67c4
Source dataset
uspto-grants-2010_01
Patent number
US07645758B2

Reaction notes

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