Chloroacetyl chloride → HCID 69146822, compound

HRID 2218253Notes

Reaction equation

HRID 2218253 reaction equation
[NH2:1][C:2]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[CH:7]=[C:6]([C:26]2[CH:31]=[CH:30][C:29]([N:32]([CH3:34])[CH3:33])=[C:28]([NH2:35])[CH:27]=2)[C:3]=1[C:4]#[N:5].[Cl:36][CH2:37][C:38](Cl)=[O:39]>C1COCC1>[NH2:1][C:2]1[C:3]([C:4]#[N:5])=[C:6]([C:26]2[CH:31]=[CH:30][C:29]([N:32]([CH3:34])[CH3:33])=[C:28]([NH:35][C:38](=[O:39])[CH2:37][Cl:36])[CH:27]=2)[CH:7]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[N:9]=1

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 69148880HCID 69148880, compound2×

Product 1

HCID 69146822HCID 69146822, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.), stirred solution of 2-amino-4-[3-amino-4-(dimethylamino)phenyl]-6-{2-[(4-methoxybenzyl)-oxy]phenyl}nicotinonitrile (starting compound 4, 0.500 g, 1.724 mmol) in THF (7 mL) under an argon atmosphere was added chloroacetyl chloride (0.121 g, 1.074 mmol). The mixture was stirred at 0° C. for 15 minutes and then partitioned between ethyl acetate and saturated aqueous NaHCO3. The separated organic phase was washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was suspended in ethyl acetate and ethanol. The resulting solid was collected by filtration, washed with ethanol, and dried under reduced pressure to give N-[5-(2-amino-3-cyano-6-{2-[(4-methoxybenzyl)oxy]-phenyl}-4-pyridinyl)-2-(dimethylamino)phenyl]-2-chloroacetamide as a yellow solid. (0.410 g, yield 70%)

Workup

  1. custompartitioned between ethyl acetate and saturated aqueous NaHCO3
  2. washThe separated organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. filtrationThe resulting solid was collected by filtration
  7. washwashed with ethanol
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-0c6038b9face4468bac42803d5937c31
Source dataset
uspto-grants-2008_08
Patent number
US07410986B2

Reaction notes

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