Dimethylformamide → 1-(6-Bromopyrid-2-yl)-1-methyl-3-heptylurea

HRID 1864554Notes

Reaction equation

HRID 1864554 reaction equation
[Br:1][C:2]1[N:7]=C(NC)[CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.ClC(OC1C=CC([N+]([O-])=O)=CC=1)=O.[CH2:32]([NH2:39])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38].[CH3:40][N:41]([CH3:44])[CH:42]=[O:43]>>[Br:1][C:2]1[N:7]=[C:40]([N:41]([CH3:44])[C:42]([NH:39][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])=[O:43])[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 81271-HeptanamineHCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 134703156-bromo-N-methylpyridin-2-amine

Product 1

HCID 860188681-(6-Bromopyrid-2-yl)-1-methyl-3-heptylureaYield 80%

Conditions

Temperature
130 °C

Procedure

1 g (5.35 mmol) of (6-bromopyrid-2-yl)-N-methylamine, 1 ml of diisopropylethylamine and 1.6 g (8 mmol) of 4-nitrophenyl chloroformate are heated at 130° C. for 15 minutes by microwave. 1.2 ml (8 mmol) of heptylamine and 7 ml of dimethylformamide are added and the reaction medium is heated at 130° C. for a further 5 minutes. The residue obtained is purified by thin-layer chromatography on silica eluted with a 70/30 heptane/ethyl acetate mixture. 1.4 g (80%) of 1-(6-bromopyrid-2-yl)-3-heptyl-1-methylurea are obtained in the form of a yellow solid.

Workup

  1. customThe residue obtained
  2. customis purified by thin-layer chromatography on silica
  3. washeluted with a 70/30 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-2628403b490f436dac85e63b8b6ce108
Source dataset
uspto-grants-2009_12
Patent number
US07625914B2

Reaction notes

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