Piperazine → Piperazin-1-yl-(4H-thieno[3,2-b]pyrrol-5-yl)-methanone

HRID 1765313Notes

Reaction equation

HRID 1765313 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.[NH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1>>[N:12]1([C:9]([C:6]2[NH:5][C:4]3[CH:3]=[CH:2][S:1][C:8]=3[CH:7]=2)=[O:11])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1

Participants

3

Reactant 2

HCID 4837PiperazineHCID 49612544H-thieno(3,2-b)pyrrole-5-carboxylic acid

Product 1

HCID 24737755Piperazin-1-yl-(4H-thieno[3,2-b]pyrrol-5-yl)-methanoneYield 35%

Procedure

4H-Thieno[3,2-b]pyrrole-5-carboxylic acid (50 mg, 0.30 mmol) was coupled with piperazine according to Procedure D to provide the title compound (25 mg, 35%) as an off-white solid. TLC (silica, 10% MeOH/CH2Cl2): Rf=0.15. MS (electrospray): exact mass calculated for C11H13N3OS, 235.08; m/z found, 236.1 [M+H]+. 1H NMR (CD3OD, 400 MHz): 7.33 (d, J=5.3 Hz, 1H), 6.98 (dd, J=5.2, 0.7 Hz, 1H), 6.89 (d, J=0.6 Hz, 1H), 4.08 (t, J=5.3 Hz, 4H), 3.50-3.20 (m, 4H).

Sources & evidence

ORD record
ord-de5cbc3d717543059ba5a0d298cad23f
Source dataset
uspto-grants-2007_06
Patent number
US07226938B2

Reaction notes

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