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

HRID 401480Notes

Reaction equation

HRID 401480 reaction equation
F[C:2]1[N:33]=[CH:32][CH:31]=[CH:30][C:3]=1[C:4]([C:6]1[N:7]=[C:8]([N:16]2[CH2:22][CH2:21][CH2:20][N:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:18][CH2:17]2)[C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:5].[OH-].[NH4+:35]>>[NH2:35][C:2]1[N:33]=[CH:32][CH:31]=[CH:30][C:3]=1[C:4]([C:6]1[N:7]=[C:8]([N:16]2[CH2:22][CH2:21][CH2:20][N:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:18][CH2:17]2)[C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:5]

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 57690632Tert-butyl 4-(3-(2-fluoronicotinoyl)isoquinolin-1-yl)-1,4-diazepane-1-carboxylate

Product 1

HCID 57690466Tert-butyl 4-(3-(2-aminonicotinoyl)isoquinolin-1-yl)-1,4-diazepane-1-carboxylateYield 24%

Conditions

Temperature
110 °C

Procedure

A microwave vial was charged with tert-butyl 4-(3-(2-fluoronicotinoyl)isoquinolin-1-yl)-1,4-diazepane-1-carboxylate (78 mg, 0.17 mmol) and a saturated aqueous solution of ammonium hydroxide (2 ml). The reaction mixture was heated under microwave irradiation at 110° C. for 25 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 (18 mg, 24% 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-21387fc97f5241b793908fa502070111
Source dataset
uspto-grants-2014_06
Patent number
US08741931B2

Reaction notes

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