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

HRID 455229Notes

Reaction equation

HRID 455229 reaction equation
[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:37]=[CH:38][CH:39]=1)[C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]2[CH:33]=[CH:32][C:22]3[N:23]=[C:24]([NH:26][C:27]([CH:29]4[CH2:31][CH2:30]4)=[O:28])[S:25][C:21]=3[C:20]=2[N+:34]([O-])=O)[CH:13]=1)=[O:10])([CH3:5])[CH3:4])#[N:2].CO>CN1CCCC1=O.[C].[Pd]>[NH2:34][C:20]1[C:21]2[S:25][C:24]([NH:26][C:27]([CH:29]3[CH2:31][CH2:30]3)=[O:28])=[N:23][C:22]=2[CH:32]=[CH:33][C:19]=1[O:18][C:14]1[CH:13]=[C:12]([NH:11][C:9](=[O:10])[C:8]2[CH:37]=[CH:38][CH:39]=[C:6]([C:3]([C:1]#[N:2])([CH3:5])[CH3:4])[CH:7]=2)[CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 594544843-(1-cyano-1-methylethyl)-N-[3-({2-[(cyclopropylcarbonyl)amino]-7-nitro-1,3-benzothiazol-6-yl}oxy)phenyl]benzamide

Product 1

HCID 59454488N-[3-({7-amino-2-[(cyclopropylcarbonyl)amino]-1,3-benzothiazol-6-yl}oxy)phenyl]-3-(1-cyano-1-methylethyl)benzamideYield 37%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 3-(1-cyano-1-methylethyl)-N-[3-({2-[(cyclopropylcarbonyl)amino]-7-nitro-1,3-benzothiazol-6-yl}oxy)phenyl]benzamide (2.5 g, 4.62 mmol) produced in Example 37(iii) in 1-methylpyrrolidin-2-one (20 ml)/methanol (50 mL) was added 10% palladium-carbon (250 mg), and the mixture was stirred at room temperature for 24 hr under a hydrogen atmosphere (3 atm). Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was diluted with ethyl acetate (200 mL), washed successively with water (200 mL), 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 to give the title compound (870 mg, 37%) as a pale-yellow powder.

Workup

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

Sources & evidence

ORD record
ord-09d3ec438f0e448cb40f3d24a9af4180
Source dataset
uspto-grants-2013_07
Patent number
US08497274B2

Reaction notes

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