Dimethylformamide → 2-(Benzo[1,3]dioxol-5-yloxy)-N-[4-(1-methyl-1-methylcarbamoyl-ethyl)-benzyl]-nicotinamide

HRID 1297599Notes

Reaction equation

HRID 1297599 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([O:10][C:11]3[C:16]([C:17]([NH:19][CH2:20][C:21]4[CH:26]=[CH:25][C:24]([C:27]([CH3:32])([CH3:31])[C:28](O)=[O:29])=[CH:23][CH:22]=4)=[O:18])=[CH:15][CH:14]=[CH:13][N:12]=3)=[CH:9][C:4]=2[O:3][CH2:2]1.[CH3:33][N:34](C)C=O.C(Cl)(=O)C(Cl)=O>ClCCl>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([O:10][C:11]3[N:12]=[CH:13][CH:14]=[CH:15][C:16]=3[C:17]([NH:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]([CH3:32])([C:28](=[O:29])[NH:34][CH3:33])[CH3:31])=[CH:23][CH:22]=3)=[O:18])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 98242372-[4-({[2-(Benzo[1,3]dioxol-5-yloxy)-pyridine-3-carbonyl]-amino}-methyl)-phenyl]-2-methyl-propionic acid

Product 1

HCID 101146022-(Benzo[1,3]dioxol-5-yloxy)-N-[4-(1-methyl-1-methylcarbamoyl-ethyl)-benzyl]-nicotinamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-[4-({[2-(Benzo[1,3]dioxol-5-yloxy)-pyridine-3-carbonyl]-amino}-methyl)-phenyl]-2-methyl-propionic acid (1.00 g) was suspended in anhydrous dichloromethane (20 mL). Anhydrous dimethylformamide (0.02 mL) was added to the suspension, followed by oxalyl chloride (0.391 mL). A 5 mL portion of this 1.15 M solution was transferred to a flame-dried, nitrogen purged round bottom flask. Anhydrous monomethyl amine gas was bubbled in for 5-10 min. The resulting white precipitate was washed with hot dichloromethane, and further purified by silica gel chromatography (ethyl acetate) to yield the title compound (0.127 g).

Workup

  1. customAnhydrous monomethyl amine gas was bubbled in for 5-10 min
  2. washThe resulting white precipitate was washed with hot dichloromethane
  3. customfurther purified by silica gel chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-a25ce743feac4ad4bc8654a4cbb76d44
Source dataset
uspto-grants-2007_07
Patent number
US07250518B2

Reaction notes

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