Acetoxyacetyl chloride → 2-({7-Benzyloxy-4-[(2-hydroxy-2-methylpropyl)amino]quinolin-3-yl}amino)-2-oxoethyl acetate hydrochloride

HRID 598296Notes

Reaction equation

HRID 598296 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][C:14]([CH3:17])([OH:16])[CH3:15])=[CH:9][CH:8]=[C:7]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:6]=2.[C:26]([O:29][CH2:30][C:31]([Cl:33])=[O:32])(=[O:28])[CH3:27]>C(#N)C>[ClH:33].[C:26]([O:29][CH2:30][C:31]([NH:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][C:14]([OH:16])([CH3:17])[CH3:15])=[CH:9][CH:8]=[C:7]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:6]=2)=[O:32])(=[O:28])[CH3:27]

Participants

4

Reactant 2

HCID 26297Acetoxyacetyl chlorideHCID 67050960HCID 67050960, compound

Product 1

HCID 670510132-({7-Benzyloxy-4-[(2-hydroxy-2-methylpropyl)amino]quinolin-3-yl}amino)-2-oxoethyl acetate hydrochlorideYield 91.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

Under a nitrogen atmosphere, a mixture of 1-{[3-amino-7-(benzyloxy)quinolin-4-yl]amino}-2-methylpropan-2-ol (45.0 g, 0.133 mol) and acetonitrile (180 mL) was heated to 40° C. Acetoxyacetyl chloride (21.8 g, 0.160 mol) was added to the resulting gray suspension over a period of 15 minutes while maintaining the temperature at 55±5° C. during the addition. Following the addition, a precipitate formed, and the reaction was heated at 55° C. for 15 minutes. The reaction mixture was then cooled to ˜0° C., and the product was isolated by filtration, washed sequentially with a small amount of acetonitrile and acetone, and dried under vacuum at 50° C. to provide 57.6 g of 2-({7-benzyloxy-4-[(2-hydroxy-2-methylpropyl)amino]quinolin-3-yl}amino)-2-oxoethyl acetate hydrochloride.

Workup

  1. temperaturewhile maintaining the temperature at 55±5° C.
  2. additionduring the addition
  3. additionthe addition
  4. customa precipitate formed
  5. temperaturethe reaction was heated at 55° C. for 15 minutes
  6. temperatureThe reaction mixture was then cooled to ˜0° C.
  7. customthe product was isolated by filtration
  8. washwashed sequentially with a small amount of acetonitrile and acetone
  9. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-f3d4826ab08e4643aa418253108e2d02
Source dataset
uspto-grants-2011_03
Patent number
US07897597B2

Reaction notes

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