Cyclopropanecarbonyl chloride → 3-(1-cyanocyclopropyl)-N-[3-({2-[(cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}oxy)-4-methylphenyl]benzamide

HRID 1800445Notes

Reaction equation

HRID 1800445 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:19][C:20](=[O:32])[C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]4([C:30]#[N:31])[CH2:29][CH2:28]4)[CH:22]=3)[CH:15]=[CH:16][C:17]=1[CH3:18])[N:5]=2.[CH:33]1([C:36](Cl)=[O:37])[CH2:35][CH2:34]1.C(=O)([O-])O.[Na+]>N1C=CC=CC=1>[C:30]([C:27]1([C:23]2[CH:22]=[C:21]([CH:26]=[CH:25][CH:24]=2)[C:20]([NH:19][C:14]2[CH:15]=[CH:16][C:17]([CH3:18])=[C:12]([O:11][C:6]3[N:5]=[C:4]4[S:3][C:2]([NH:1][C:36]([CH:33]5[CH2:35][CH2:34]5)=[O:37])=[N:10][C:9]4=[CH:8][CH:7]=3)[CH:13]=2)=[O:32])[CH2:29][CH2:28]1)#[N:31]

Participants

5

Reactant 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 516892Sodium BicarbonateHCID 86645997HCID 86645997, compound

Product 1

HCID 595070113-(1-cyanocyclopropyl)-N-[3-({2-[(cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}oxy)-4-methylphenyl]benzamideYield 61%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of N-{3-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-4-methylphenyl}-3-(1-cyanocyclopropyl)benzamide (200 mg, 0.452 mmol) in pyridine (5 mL) was added cyclopropanecarbonyl chloride (77.8 μL, 1.13 mmol), and the mixture was stirred at room temperature for 30 min. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtrated. The solvent was evaporated under reduced pressure, and the residue was precipitated with tetrahydrofuran to give the title compound (140 mg, 61%) as a white powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltrated
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was precipitated with tetrahydrofuran

Sources & evidence

ORD record
ord-13c135255d6543708e564713e996372c
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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