Cyclopropanecarbonyl chloride → 3-(1-cyano-1-methylethyl)-N-[3-({2-[(cyclopropylcarbonyl)amino]-7-nitro-1,3-benzothiazol-6-yl}oxy)phenyl]benzamide

HRID 455217Notes

Reaction equation

HRID 455217 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:10]([N+:11]([O-:13])=[O:12])=[C:9]([O:14][C:15]3[CH:16]=[C:17]([NH:21][C:22](=[O:34])[C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([C:32]#[N:33])([CH3:31])[CH3:30])[CH:24]=4)[CH:18]=[CH:19][CH:20]=3)[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH:35]1([C:38](Cl)=[O:39])[CH2:37][CH2:36]1>N1C=CC=CC=1>[C:32]([C:29]([C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][CH:26]=1)[C:22]([NH:21][C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([O:14][C:9]2[CH:8]=[CH:7][C:5]3[N:6]=[C:2]([NH:1][C:38]([CH:35]4[CH2:37][CH2:36]4)=[O:39])[S:3][C:4]=3[C:10]=2[N+:11]([O-:13])=[O:12])[CH:16]=1)=[O:34])([CH3:30])[CH3:31])#[N:33]

Participants

4

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 86644697N-{3-[(2-amino-7-nitro-1,3-benzothiazol-6-yl)oxy]phenyl}-3-(1-cyano-1-methylethyl)benzamide

Product 1

HCID 594544843-(1-cyano-1-methylethyl)-N-[3-({2-[(cyclopropylcarbonyl)amino]-7-nitro-1,3-benzothiazol-6-yl}oxy)phenyl]benzamideYield 79.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of N-{3-[(2-amino-7-nitro-1,3-benzothiazol-6-yl)oxy]phenyl}-3-(1-cyano-1-methylethyl)benzamide (3.0 g, 6.33 mmol) in pyridine (30 mL) was added cyclopropanecarbonyl chloride (1.15 ml, 12.7 mmol) at 4° C., and the mixture was stirred at room temperature for 4 hr. The reaction mixture was concentrated under reduced pressure. The obtained residue was diluted with ethyl acetate (300 mL)/tetrahydrofuran (30 mL), washed successively with 5% aqueous sodium hydrogen carbonate solution (200 mL) and saturated brine (200 mL), and dried over anhydrous sodium sulfate. Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (ethyl acetate/n-hexane=30/70→100/0), and the obtained solution was concentrated under reduced pressure. The residue was recrystallized from ethyl acetate/n-hexane to give the title compound (2.71 g, 79%) as a yellow powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionThe obtained residue was diluted with ethyl acetate (300 mL)/tetrahydrofuran (30 mL)
  3. washwashed successively with 5% aqueous sodium hydrogen carbonate solution (200 mL) and saturated brine (200 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationInsoluble material was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe obtained residue was purified by basic silica gel column chromatography (ethyl acetate/n-hexane=30/70→100/0)
  8. concentrationthe obtained solution was concentrated under reduced pressure
  9. customThe residue was recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-ff1d9e1b4a294c428ca0b77eba619b4f
Source dataset
uspto-grants-2013_07
Patent number
US08497274B2

Reaction notes

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