Ammonium Chloride → HCID 86657968, compound

HRID 2366766Notes

Reaction equation

HRID 2366766 reaction equation
[CH3:1][N:2]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([NH:24]C(=O)C(F)(F)F)[CH:19]=1)[C:3]1[N:8]=[C:7]2[S:9][C:10]([NH:12][C:13]([CH:15]3[CH2:17][CH2:16]3)=[O:14])=[N:11][C:6]2=[CH:5][CH:4]=1.[Cl-].[NH4+]>O1CCCC1.CO.[OH-].[Na+]>[NH2:24][C:20]1[CH:19]=[C:18]([N:2]([CH3:1])[C:3]2[N:8]=[C:7]3[S:9][C:10]([NH:12][C:13]([CH:15]4[CH2:16][CH2:17]4)=[O:14])=[N:11][C:6]3=[CH:5][CH:4]=2)[CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 86657967HCID 86657967, compound

Product 1

HCID 86657968HCID 86657968, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

N-[5-(Methyl{3-[(trifluoroacetyl)amino]phenyl}amino)[1,3]thiazolo[5,4-b]pyridin-2-yl]cyclopropanecarboxamide (748 mg, 1.72 mmol) was dissolved in tetrahydrofuran (22.5 mL)/methanol (7.5 mL), 2N aqueous sodium hydroxide solution (7.5 mL) was added, and the mixture was stirred at room temperature for 19 hr. Aqueous ammonium chloride 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 residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20→0/100) to give the title compound (542 mg, 93%) as a colorless powder.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate (50 mL)
  3. washThe organic layer was washed with saturated brine (20 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20→0/100)

Sources & evidence

ORD record
ord-4b784e6da55540d4b3355f38d9a2300b
Source dataset
uspto-grants-2014_04
Patent number
US08697874B2

Reaction notes

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