5-((E)-3-Dimethylamino-acryloyl)-1H-pyrrole-3-carboxylic acid ethyl ester → 5-{2-[2-Methoxy-4-(4-methyl-piperazin-1-yl)-phenylamino]-pyrimidin-4-yl}-1H-pyrrole-3-carboxylic acid ethyl ester

HRID 1619086Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11](=O)/[CH:12]=[CH:13]/N(C)C)[NH:8][CH:7]=1)=[O:5])[CH3:2].[CH3:18][O:19][C:20]1[CH:25]=[C:24]([N:26]2[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]2)[CH:23]=[CH:22][C:21]=1[NH:33][C:34]([NH2:36])=[NH:35].C(O)C>O>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[CH:12]=[CH:13][N:36]=[C:34]([NH:33][C:21]3[CH:22]=[CH:23][C:24]([N:26]4[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]4)=[CH:25][C:20]=3[O:19][CH3:18])[N:35]=2)[NH:8][CH:7]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 110 °C

Procedure

To a suspension of 5-((E)-3-Dimethylamino-acryloyl)-1H-pyrrole-3-carboxylic acid ethyl ester (1.7 g, 7.20 mmol) in 30 mL of ethanol N-[2-Methoxy-4-(4-methyl-piperazin-1-yl)-phenyl]-guanidine (1.9 g, 7.20 mmol) was added. The mixture was heated to 110° C. overnight. The resulting mixture was cooled at room temperature and diluted with water (70 mL). The solid was isolated by filtration, washed with 10 mL of water, dried in a vacuum oven at 40° C. affording to give 1.8 g (57% yield) of the title compound.

Workup

additionwas added
temperatureThe resulting mixture was cooled at room temperature
customThe solid was isolated by filtration
washwashed with 10 mL of water
customdried in a vacuum oven at 40° C.
customaffording

Sources & evidence

ORD record: ord-8ebac3d87205442da5938724a3b303d1
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772280B2

Reaction notes

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