Ammonium Hydroxide → Tert-butyl 4-(1-(2-aminonicotinoyl)isoquinolin-3-yl)piperazine-carboxylate

HRID 401503Notes

Reaction equation

HRID 401503 reaction equation
F[C:2]1[N:32]=[CH:31][CH:30]=[CH:29][C:3]=1[C:4]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]([N:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)[N:7]=1)=[O:5].[OH-].[NH4+:34]>>[NH2:34][C:2]1[N:32]=[CH:31][CH:30]=[CH:29][C:3]=1[C:4]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]([N:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)[N:7]=1)=[O:5]

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 57690626HCID 57690626, compound

Product 1

HCID 57690535Tert-butyl 4-(1-(2-aminonicotinoyl)isoquinolin-3-yl)piperazine-carboxylateYield 76%

Conditions

Temperature
120 °C

Procedure

A microwave vial was charged with tert-butyl 4-(1-(2-fluoronicotinoyl)isoquinolin-3-yl)piperazine-1-carboxylate (8 mg, 0.018 mmol) and a saturated aqueous solution of ammonium hydroxide (3 ml). The reaction mixture was heated under microwave irradiation at 120° C. for 30 minutes. The mixture was cooled down to room temperature, partitioned between ethyl acetate and water. The organic phase was dried over magnesium sulfate, filtered and evaporated to dryness. The residue was purified on silica gel by flash column chromatography to afford the title compound as a yellow solid (6 mg, 76% yield).

Workup

  1. temperatureThe mixture was cooled down to room temperature
  2. custompartitioned between ethyl acetate and water
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was purified on silica gel by flash column chromatography

Sources & evidence

ORD record
ord-dac077a46e4645519993e3eea3377b40
Source dataset
uspto-grants-2014_06
Patent number
US08741931B2

Reaction notes

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