Pyridine → N-(3-{[2-(acetylamino)-7-cyano-1,3-benzothiazol-6-yl]oxy}phenyl)-2-chloro-3-(1-cyano-1-methylethyl)benzamide

HRID 455178Notes

Reaction equation

HRID 455178 reaction equation
[Cl:1][C:2]1[C:34]([C:35]([C:38]#[N:39])([CH3:37])[CH3:36])=[CH:33][CH:32]=[CH:31][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][C:14]2[CH:28]=[CH:27][C:17]3[N:18]=[C:19]([NH:21][C:22]([CH:24]4CC4)=[O:23])[S:20][C:16]=3[C:15]=2[C:29]#[N:30])[CH:8]=1)=[O:5].N1C=CC=CC=1.C(Cl)(=O)C>O1CCCC1>[C:22]([NH:21][C:19]1[S:20][C:16]2[C:15]([C:29]#[N:30])=[C:14]([O:13][C:9]3[CH:8]=[C:7]([NH:6][C:4](=[O:5])[C:3]4[CH:31]=[CH:32][CH:33]=[C:34]([C:35]([C:38]#[N:39])([CH3:37])[CH3:36])[C:2]=4[Cl:1])[CH:12]=[CH:11][CH:10]=3)[CH:28]=[CH:27][C:17]=2[N:18]=1)(=[O:23])[CH3:24]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 462223542-chloro-N-[3-({7-cyano-2-[(cyclopropylcarbonyl)amino]-1,3-benzothiazol-6-yl}oxy)phenyl]-3-(1-cyano-1-methylethyl)benzamide

Product 1

HCID 59454509N-(3-{[2-(acetylamino)-7-cyano-1,3-benzothiazol-6-yl]oxy}phenyl)-2-chloro-3-(1-cyano-1-methylethyl)benzamideYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-{3-[(2-amino-7-cyano-1,3-benzothiazol-6-yl)oxy]phenyl}-2,2,2-trifluoroacetamide (8.0 g, 21.1 mmol) produced in Example 3 (iv) in tetrahydrofuran (100 mL) were added pyridine (20 mL, 250 mmol) and acetyl chloride (1.8 mL, 25.3 mmol), and the mixture was stirred at room temperature for 2 hr. Insoluble material was filtered off, and the filtrate was diluted with ethyl acetate (500 mL). The obtained solution was washed successively with 5% aqueous sodium hydrogen carbonate solution (300 mL) and saturated brine (300 mL), and dried over anhydrous sodium sulfate. Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (6.43 g, 72%) as a white powder.

Workup

  1. filtrationInsoluble material was filtered off
  2. additionthe filtrate was diluted with ethyl acetate (500 mL)
  3. washThe obtained solution was washed successively with 5% aqueous sodium hydrogen carbonate solution (300 mL) and saturated brine (300 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationInsoluble material was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-062281f5b3824889be5443f4662eab1d
Source dataset
uspto-grants-2013_07
Patent number
US08497274B2

Reaction notes

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