Acetone → Ammonia

HRID 729530Notes

Reaction equation

HRID 729530 reaction equation
[CH:1]12[CH2:7][CH:4]([NH:5][CH2:6]1)[CH2:3][N:2]2[C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][CH:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH3:25])[CH:18]=2)[N:9]=1.[CH3:32][C:33]([CH3:35])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)(Cl)Cl.C(Cl)Cl>[NH3:2].[CH:33]([N:5]1[CH2:6][C@@H:1]2[CH2:7][C@H:4]1[CH2:3][N:2]2[C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C@H:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH3:25])[CH:18]=2)[N:9]=1)([CH3:35])[CH3:32]

Participants

7

Reactant 3

HCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 68907408HCID 68907408, compound

Product 2

HCID 222AmmoniaYield 5%HCID 68909850HCID 68909850, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of {4-[3-(2,5-diaza-bicyclo[2.2.1]hept-2-yl)-indazol-1-yl]-pyridin-2-yl}-(1-phenyl-ethyl)-amine (0.03 g, 0.074 mmol) in chloroform (1 mL) were added acetone (0.5 mL) and sodium triacetoxyborohydride (0.039 g, 0.18 mmol) and the solution was stirred at 70° C. for 1 h. After cooling to room temperature, the reaction was diluted with methylene chloride and washed with saturated sodium bicarbonate. The aqueous layer was back-extracted with methylene chloride (2×). The combined organic extracts were dried (K2CO3), filtered, and concentrated in vacuo. Flash chromatography with 1%, 3%, and 5% 2M NH3 in MeOH/CHCl3 gave the title compound as an off-white glass. MS (ES+): 453.3 [M+H]+, 451.4 [M−H]−.

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with saturated sodium bicarbonate
  3. extractionThe aqueous layer was back-extracted with methylene chloride (2×)
  4. dry with materialThe combined organic extracts were dried (K2CO3)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9347e77d1b87492b9b1932c5823f7125
Source dataset
uspto-grants-2009_09
Patent number
US07582631B2

Reaction notes

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