Sodium Chloride → HCID 178509115, compound

HRID 1959849Notes

Reaction equation

HRID 1959849 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([CH:7]2[CH2:12][CH2:11][N:10](C(=O)C)[CH2:9][CH2:8]2)[C:3]=1[C:16]1[S:17][C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=1.[OH-].[Na+].[Na+].[Cl-]>Cl>[NH3:1].[S:17]1[C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=[C:16]1[C:3]1[C:4]([CH:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]2)=[N:5][NH:6][C:2]=1[NH2:1]

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 178473791HCID 178473791, compound

Product 2

HCID 222AmmoniaYield 1%HCID 178509115HCID 178509115, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of the above prepared 1-[4-(5-amino-4-benzothiazol-2-yl-1H-pyrazol-3-yl)-piperidin-1-yl]-ethanone (54 mg, 0.158 mmol) in 6N HCl (10 mL) was refluxed for 6 hrs and was allowed to cool to room temperature overnight. The resulting mixture was poured over crushed ice (20 mL) and the solution was adjusted to neutral pH using a 10% NaOH solution. The resulting solution was saturated with NaCl and was extracted with ethyl acetate (10×50 mL). The combined extracts were washed once with brine, dried over anhydrous sodium sulfate, filtered and evaporated. The resulting crude product was purified by flash column chromatography eluting with CH2Cl2:MeOH=20:1 with 1% ammonia to yield 15 mg (32%) of the title compound. MS (m/z, ES+): 300.14 (M+1, 100%).

Workup

  1. temperaturewas refluxed for 6 hrs
  2. additionThe resulting mixture was poured
  3. extractionwas extracted with ethyl acetate (10×50 mL)
  4. washThe combined extracts were washed once with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe resulting crude product was purified by flash column chromatography
  9. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-93d483078ef74bef9738f89f9218e97b
Source dataset
uspto-grants-2013_04
Patent number
US08410272B2

Reaction notes

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