Ammonium Chloride → 4-Benzothiazol-2-YL-N3-(2-ethylaminoethyl)-1H-pyrazole-3,5-diamine

HRID 57246Notes

Reaction equation

HRID 57246 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([NH:7][CH2:8][CH2:9][NH:10][C:11](=O)[CH3:12])[C:3]=1[C:14]1[S:15][C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[N:18]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[NH4+]>C1COCC1>[S:15]1[C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[N:18]=[C:14]1[C:3]1[C:4]([NH:7][CH2:8][CH2:9][NH:10][CH2:11][CH3:12])=[N:5][NH:6][C:2]=1[NH2:1]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 66768089N-[2-(5-amino-4-benzothiazol-2-yl-1H-pyrazol-3-ylamino)ethyl]acetamide

Product 1

HCID 667680044-Benzothiazol-2-YL-N3-(2-ethylaminoethyl)-1H-pyrazole-3,5-diamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-[2-(5-Amino-4-benzothiazol-2-yl-1H-pyrazol-3-ylamino)ethyl]acetamide (80 mg, 0.25 mmol) and lithium aluminum hydride (92 mg) were refluxed in anhydrous THF (10 mL) for 3 hrs. The resulting mixture was poured into a saturated ammonium chloride solution (50 mL). The aqueous phase was extracted with ethyl acetate (3×50 mL). The combined extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated to yield 54 mg of crude product. The crude product was purified by flash column chromatography eluting with CH2Cl2:MeOH=5:1 with 0.5% NH3. The title compound was isolated in a yield of 36 mg (48%). MS (m/z, ES+): 303.1 (M+1, 100%).

Workup

  1. extractionThe aqueous phase was extracted with ethyl acetate (3×50 mL)
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customto yield 54 mg of crude product
  7. customThe crude product was purified by flash column chromatography
  8. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-5414aab2f53f4c0b8ebc89b95dca23bf
Source dataset
uspto-grants-2016_09
Patent number
US09434720B2

Reaction notes

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