Chloroacetyl chloride → N-[3-({2-[(chloroacetyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}oxy)-4-cyanophenyl]-3-(1-cyano-1-methylethyl)benzamide

HRID 1800492Notes

Reaction equation

HRID 1800492 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:9]([N:10]=1)=[CH:8][CH:7]=[C:6]([O:11][C:12]1[CH:13]=[C:14]([NH:20][C:21](=[O:33])[C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([C:31]#[N:32])([CH3:30])[CH3:29])[CH:23]=3)[CH:15]=[CH:16][C:17]=1[C:18]#[N:19])[N:5]=2.[Cl:34][CH2:35][C:36](Cl)=[O:37]>CN(C)C=O.C(OCC)(=O)C>[Cl:34][CH2:35][C:36]([NH:1][C:2]1[S:3][C:4]2[C:9]([N:10]=1)=[CH:8][CH:7]=[C:6]([O:11][C:12]1[CH:13]=[C:14]([NH:20][C:21](=[O:33])[C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([C:31]#[N:32])([CH3:29])[CH3:30])[CH:23]=3)[CH:15]=[CH:16][C:17]=1[C:18]#[N:19])[N:5]=2)=[O:37]

Participants

5

Reactant 2

HCID 6577Chloroacetyl chloride2×HCID 86646007N-{3-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-4-cyanophenyl}-3-(1-cyano-1-methylethyl)benzamide

Product 1

HCID 86646008N-[3-({2-[(chloroacetyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}oxy)-4-cyanophenyl]-3-(1-cyano-1-methylethyl)benzamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-{3-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-4-cyanophenyl}-3-(1-cyano-1-methylethyl)benzamide (150 mg, 0.330 mmol) produced in Example C43(vi) in N,N-dimethylformamide (3.0 mL) was added chloroacetyl chloride (42 μL, 0.528 mmol), and the mixture was stirred at room temperature for 4 hr. Chloroacetyl chloride (21 μL, 0.264 mmol) was further added, and the mixture was stirred at room temperature for 12 hr. The reaction mixture was diluted with ethyl acetate (100 mL), washed with 5% aqueous sodium hydrogen carbonate solution (100 mL) and saturated brine (100 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give N-[3-({2-[(chloroacetyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}oxy)-4-cyanophenyl]-3-(1-cyano-1-methylethyl)benzamide as a colorless solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 12 hr
  2. washwashed with 5% aqueous sodium hydrogen carbonate solution (100 mL) and saturated brine (100 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe insoluble material was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b07112063c874a448060711f247c7585
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

Loading…