tert-Butoxy bis(dimethylamino)methane → 1,1-Dimethylethyl [2-[3-(dimethylamino)-2-fluoroacryloyl]-5-fluoro-6-(methyloxy)-3-pyridinyl]carbamate

HRID 15132Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:5]([C:10](=[O:13])[CH2:11][F:12])=[N:6][C:7]=1[O:8][CH3:9].[CH3:22][N:23]([CH:25](N(C)C)OC(C)(C)C)[CH3:24]>C1(C)C=CC=CC=1>[CH3:22][N:23]([CH3:25])[CH:24]=[C:11]([F:12])[C:10]([C:5]1[C:4]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[CH:3][C:2]([F:1])=[C:7]([O:8][CH3:9])[N:6]=1)=[O:13]

Participants

Conditions

Temperature: 40 °C

Procedure

A solution of 1,1-dimethylethyl [5-fluoro-2-(fluoroacetyl)-6-(methyloxy)-3-pyridinyl]carbamate (3.72 g, 12.32 mmol) in dry toluene (20 ml) was treated with {(dimethylamino)[(1,1-dimethylethyl)oxy]methyl}dimethylamine (Bredereck's reagent) (3.05 ml, 14.78 mmol) and heated at 40° C. for 2 hours. The mixture was evaporated and the residue triturated with 3×200 ml hexane and the remaining solid dried in vacuo to afford the product (2.15 g, 49%).

Workup

customThe mixture was evaporated
customthe residue triturated with 3×200 ml hexane
customthe remaining solid dried in vacuo

Sources & evidence

ORD record: ord-087edd2ce0ff4baa9e4675e2e81deb28
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732460B2

Reaction notes

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