1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → [4-(2-diethylamino-ethyl)-piperazin-1-yl]-[4-methyl-1-(4-methylbenzyl)-3-p-tolyl-1H-pyrrol-2-yl]-methanone

HRID 2427410Notes

Reaction equation

CCN=C=NCCCN(C)C.C1C=NC2N(O)N=NC=2C=1.[CH3:22][C:23]1[C:24]([C:39]2[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][CH:40]=2)=[C:25]([C:36](O)=[O:37])[N:26]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=2)[CH:27]=1.[CH2:46]([N:48]([CH2:57][CH3:58])[CH2:49][CH2:50][N:51]1[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]1)[CH3:47]>C(Cl)Cl>[CH2:57]([N:48]([CH2:46][CH3:47])[CH2:49][CH2:50][N:51]1[CH2:52][CH2:53][N:54]([C:36]([C:25]2[N:26]([CH2:28][C:29]3[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=3)[CH:27]=[C:23]([CH3:22])[C:24]=2[C:39]2[CH:40]=[CH:41][C:42]([CH3:45])=[CH:43][CH:44]=2)=[O:37])[CH2:55][CH2:56]1)[CH3:58]

Participants

Conditions

Temperature: 0 °C

Procedure

EDCI (166 mg, 0.87 mmol) and HOAt (11 mg, 0.08 mmol) were added at 0° C. to a reaction mixture of 4-methyl-1-(4-methylbenzyl)-3-p-tolyl-1H-pyrrole-2-carboxylic acid (252 mg, 0.79 mmol) and 1-(2-diethylaminoethyl)-piperazine (146 mg, 0.79 mmol) in DCM (5 mL) and the reaction mixture was stirred for 30 min at 0° C. and overnight at RT. After removal of the solvent, purification proceeded by means of column chromatography and the desired product [4-(2-diethylamino-ethyl)-piperazin-1-yl]-[4-methyl-1-(4-methylbenzyl)-3-p-tolyl-1H-pyrrol-2-yl]-methanone (148 mg, 38% of theoretical) was obtained.

Workup

customAfter removal of the solvent, purification

Sources & evidence

ORD record: ord-c58e698f80a14adcb0050da2757fdec5
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968591B2

Reaction notes

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