Dimethylformamide → tert-Butyl 2-(3-(2,5-Dimethyl-1H-pyrrol-1-yl)-5-(methoxy(methyl)carbamoyl)-1H-pyrazol-1-yl)ethylcarbamate

HRID 1022134Notes

Reaction equation

[CH3:1][C:2]1[N:3]([C:8]2[CH:12]=[C:11]([C:13]([N:15]([O:17][CH3:18])[CH3:16])=[O:14])[NH:10][N:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.Cl[CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26].C([O-])([O-])=O.[Na+].[Na+].CN(C=O)C>O>[CH3:1][C:2]1[N:3]([C:8]2[CH:12]=[C:11]([C:13](=[O:14])[N:15]([O:17][CH3:18])[CH3:16])[N:10]([CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[N:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A 250-mL round-bottomed flask equipped with a magnetic stirrer was charged with 287c (10.4 g, 1.0 eq., 41.9 mmol), tert-butyl 2-chloroethylcarbamate (37.7 g, 5.0 eq., 210.0 mmol), Na2CO3 (22.3 g, 5.0 eq., 210.0 mmol), and DMF (100 mL). The reaction mixture was stirred at 110° C. overnight. After cooling to room temperature, the resulting mixture was poured into water (200 mL) and extracted with ethyl acetate (3×100 mL). The combined organic layer was concentrated under reduced pressure. The resulting residue was purified by silica-gel column chromatography eluting with ethyl acetate to afford 287d (10.8 g, 66%) as yellow oil. MS-ESI: [M+H]+ 392.0

Workup

customA 250-mL round-bottomed flask equipped with a magnetic stirrer
temperatureAfter cooling to room temperature
extractionextracted with ethyl acetate (3×100 mL)
concentrationThe combined organic layer was concentrated under reduced pressure
customThe resulting residue was purified by silica-gel column chromatography
washeluting with ethyl acetate

Sources & evidence

ORD record: ord-c074c26eb7de4ace8e466aaa7411eb5c
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08716274B2

Reaction notes

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