Ethoxyacetyl chloride → HCID 69506831, compound

HRID 2366742Notes

Reaction equation

HRID 2366742 reaction equation
[CH2:1]([O:3][CH2:4][C:5]([Cl:7])=[O:6])[CH3:2].[NH2:8][C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1[NH:19][CH2:20][C:21]1([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)=[CH:16][CH:15]=[CH:14][CH:13]=2>C(#N)C>[ClH:7].[CH2:1]([O:3][CH2:4][C:5]([NH:8][C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1[NH:19][CH2:20][C:21]1([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:6])[CH3:2]

Participants

4

Reactant 2

HCID 84189Ethoxyacetyl chlorideHCID 69506811HCID 69506811, compound

Product 1

HCID 69506831HCID 69506831, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of ethoxyacetyl chloride (3.95 g, 32.3 mmol) in acetonitrile (10 mL) was added to a solution of ethyl 1-{[(3-aminoquinolin-4-yl)amino]methyl}cyclohexanecarboxylate (9.60 g, 29.3 mmol) in acetonitrile (200 mL), and the resulting mixture was stirred for five hours at ambient temperature. A precipitate was present and was isolated by filtration, washed with cold acetonitrile, and dried overnight under vacuum to provide 10.18 g of ethyl 1-[({3-[(ethoxyacetyl)amino]quinolin-4-yl}amino)methyl]cyclohexanecarboxylate hydrochloride.

Workup

  1. customwas isolated by filtration
  2. washwashed with cold acetonitrile
  3. customdried overnight under vacuum

Sources & evidence

ORD record
ord-9d907cda1fd747d786d693f27e7dae15
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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