Acetoxyacetyl chloride → HCID 86626697, compound

HRID 81882Notes

Reaction equation

HRID 81882 reaction equation
[NH2:1][C:2]1[C:3]([Cl:25])=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][C:14]([NH:17][C:18](=[O:24])[O:19]C(C)(C)C)([CH3:16])[CH3:15])=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:26]([O:29][CH2:30][C:31](Cl)=[O:32])(=[O:28])[CH3:27]>C(#N)C>[ClH:25].[C:26]([O:29][CH2:30][C:31]([NH:1][C:2]1[C:3]([Cl:25])=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][C:14]([NH:17][C:18](=[O:24])[OH:19])([CH3:15])[CH3:16])=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:32])(=[O:28])[CH3:27]

Participants

4

Reactant 2

HCID 26297Acetoxyacetyl chlorideHCID 86626699HCID 86626699, compound

Product 1

HCID 86626697HCID 86626697, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
5 °C

Procedure

The solution of tert-butyl N-{2-[(3-amino-2-chloroquinolin-4-yl)amino]-1,1-dimethylethyl}carbamate in acetonitrile from Part C was cooled to 5° C. using an ice bath. A solution of acetoxyacetyl chloride (4.8 g, 35.1 mmol) in acetonitrile (20 mL) was added dropwise at a rate such that the temperature of the reaction mixture was maintained at 5° C. After the addition was complete the ice bath was removed and the reaction mixture was allowed to stir at ambient temperature for 5 hours. The reaction mixture was concentrated under reduced pressure to provide 16.7 g of N-{2-[(3-acetoxyacetylamino-2-chloroquinolin-4-yl)amino]-1,1-dimethylethyl}carbamate hydrochloride as a yellow powder.

Workup

  1. additionAfter the addition
  2. customwas removed
  3. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-be9758223451408bbcf820993d77e7c0
Source dataset
uspto-grants-2014_09
Patent number
US08846710B2

Reaction notes

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