Ethylamine hydrochloride → HCID 58153406, compound

HRID 1894658Notes

Reaction equation

HRID 1894658 reaction equation
Cl.[CH2:2]([NH2:4])[CH3:3].CCN(C(C)C)C(C)C.CO[CH:16]=[N:17][C:18]1[C:19]([CH3:32])=[N:20][C:21]([O:25][CH2:26][CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30])=[C:22]([Br:24])[CH:23]=1>ClCCl>[Br:24][C:22]1[CH:23]=[C:18]([NH:17][CH:16]=[N:4][CH2:2][CH3:3])[C:19]([CH3:32])=[N:20][C:21]=1[O:25][CH2:26][CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30]

Participants

5

Reactant 3

HCID 11198Ethylamine hydrochlorideHCID 81531DiisopropylethylamineHCID 58153374HCID 58153374, compound

Product 1

HCID 58153406HCID 58153406, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 50 ml single-necked round-bottomed flask, 540 mg of N-[5-Bromo-2-methyl-6-(4-methyl-pentyloxy)-pyridin-3-yl]-formimidic acid methyl ester is dissolved in 6.60 ml of dry dichloromethane. Under stirring at an ambient temperature, 214 mg of ethylamine hydrochloride along with 0.45 ml of Hünig's base are added. Stirring is continued at room temperature for 20 hours. Then, the volatiles are removed in vacuo at 50 oC. After purification on silica gel (eluent: heptane/ethyl acetate 8:1 (v:v) with 5% triethylamine) to give 530 mg of the title compound in the form of a brown oil.

Workup

  1. stirringStirring
  2. customThen, the volatiles are removed in vacuo at 50 oC
  3. customAfter purification on silica gel (eluent: heptane/ethyl acetate 8:1 (v:v) with 5% triethylamine)

Sources & evidence

ORD record
ord-b021ed3e8e994822ad7a803b0f641596
Source dataset
uspto-grants-2013_08
Patent number
US08513286B2

Reaction notes

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