Ethylamine → HCID 178464584, compound

HRID 1290219Notes

Reaction equation

HRID 1290219 reaction equation
[NH2:1][CH2:2][C:3]([N:5]([C:7]1[C:8]([Cl:27])=[C:9]([C:23]([Cl:26])=[CH:24][CH:25]=1)[CH2:10][O:11][C:12]1[C:13]2[N:14]([C:18]([Br:22])=[C:19]([CH3:21])[N:20]=2)[CH:15]=[CH:16][CH:17]=1)[CH3:6])=[O:4].CS[C:30](SC)=[N:31][C:32]#[N:33].[CH2:36]([NH2:38])[CH3:37]>CN(C)C=O.O>[Br:22][C:18]1[N:14]2[CH:15]=[CH:16][CH:17]=[C:12]([O:11][CH2:10][C:9]3[C:23]([Cl:26])=[CH:24][CH:25]=[C:7]([N:5]([C:3](=[O:4])[CH2:2][NH:1][C:30]([NH:38][CH2:36][CH3:37])=[N:31][C:32]#[N:33])[CH3:6])[C:8]=3[Cl:27])[C:13]2=[N:20][C:19]=1[CH3:21]

Participants

6

Reactant 3

HCID 6341EthylamineHCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 10790603HCID 10790603, compound

Product 1

HCID 178464584HCID 178464584, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 8-[3-(N-glycyl-N-methylamino)-2,6-dichlorobenzyloxy]-3-bromo-2-methylimidazo[1,2-a]pyridine (300 mg) and dimethyl cyanodithioiminocarbonate (93 mg) in dimethylformamide (3 ml) was heated at 700° C. for 1 hour. After cooling the reacting mixture, to the mixture was added 70% solution of ethylamine in water (0.57 ml) and the mixture was heated at 60° C. for 2 hours. To this mixture was added water (3 ml) in an ice-water bath. The precipitates were collected by vacuum filtration and washed with ethyl acetate to give 3-bromo-8-[3-[N-[(2-cyano-3-ethylguanidino)acetyl]-N-methylamino]-2,6-dichlorobenzyloxy]-2-methylimidazo[1,2-a]pyridine (278 mg) as colorless crystals.

Workup

  1. temperatureAfter cooling the reacting mixture
  2. filtrationThe precipitates were collected by vacuum filtration
  3. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-f9492616a1d9458d8787b04d05e71b1e
Source dataset
uspto-grants-1998_05
Patent number
US05750699

Reaction notes

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