Sodium Bicarbonate → HCID 58451280, compound

HRID 2366769Notes

Reaction equation

HRID 2366769 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:8]([CH3:24])[C:9]2[N:14]=[C:13]3[S:15][C:16]([NH:18][C:19]([CH:21]4[CH2:23][CH2:22]4)=[O:20])=[N:17][C:12]3=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([N:32]=[C:33]=[O:34])=[CH:28][C:27]=1[C:35]([F:38])([F:37])[F:36].C(=O)([O-])O.[Na+]>CN(C)C=O>[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([NH:32][C:33]([NH:1][C:2]2[CH:3]=[C:4]([N:8]([CH3:24])[C:9]3[N:14]=[C:13]4[S:15][C:16]([NH:18][C:19]([CH:21]5[CH2:22][CH2:23]5)=[O:20])=[N:17][C:12]4=[CH:11][CH:10]=3)[CH:5]=[CH:6][CH:7]=2)=[O:34])=[CH:28][C:27]=1[C:35]([F:36])([F:37])[F:38]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 27332651-Chloro-4-isocyanato-2-(trifluoromethyl) benzeneHCID 86657968HCID 86657968, compound

Product 1

HCID 58451280HCID 58451280, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-{5-[(3-aminophenyl)(methyl)amino][1,3]thiazolo[5,4-b]pyridin-2-yl}cyclopropanecarboxamide (100 mg, 0.295 mmol) produced in Example 8(x) in N,N-dimethylformamide (1.0 mL) was added 1-chloro-4-isocyanato-2-(trifluoromethyl)benzene (78.4 mg, 0.354 mmol), and the mixture was stirred at room temperature for 1 hr. Aqueous sodium hydrogen carbonate solution (20 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate (50 mL). The organic layer was washed with saturated brine (20 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The precipitate was collected by filtration and recrystallized from hexane/tetrahydrofuran to give the title compound (118 mg, 72%) as a colorless powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (50 mL)
  2. washThe organic layer was washed with saturated brine (20 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. filtrationThe precipitate was collected by filtration
  6. customrecrystallized from hexane/tetrahydrofuran

Sources & evidence

ORD record
ord-ec1a3022a9e94b88a52cf832acb6a83c
Source dataset
uspto-grants-2014_04
Patent number
US08697874B2

Reaction notes

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