Ammonium Hydroxide → Tert-butyl 4-(6-(2-amino-5-methylnicotinoyl)pyridin-2-yl)-1,4-diazepane-1-carboxylate

HRID 401485Notes

Reaction equation

HRID 401485 reaction equation
F[C:2]1[N:29]=[CH:28][C:27]([CH3:30])=[CH:26][C:3]=1[C:4]([C:6]1[N:11]=[C:10]([N:12]2[CH2:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14][CH2:13]2)[CH:9]=[CH:8][CH:7]=1)=[O:5].[OH-].[NH4+:32]>>[NH2:32][C:2]1[N:29]=[CH:28][C:27]([CH3:30])=[CH:26][C:3]=1[C:4]([C:6]1[N:11]=[C:10]([N:12]2[CH2:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14][CH2:13]2)[CH:9]=[CH:8][CH:7]=1)=[O:5]

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 57690501Tert-butyl 4-(6-(2-fluoro-5-methylnicotinoyl)pyridin-2-yl)-1,4-diazepane-1-carboxylate

Product 1

HCID 57690635Tert-butyl 4-(6-(2-amino-5-methylnicotinoyl)pyridin-2-yl)-1,4-diazepane-1-carboxylateYield 18%

Conditions

Temperature
110 °C

Procedure

A microwave vial was charged with tert-butyl 4-(6-(2-fluoro-5-methylnicotinoyl)pyridin-2-yl)-1,4-diazepane-1-carboxylate (280 mg, 0.68 mmol) and a saturated aqueous solution of ammonium hydroxide (1.5 ml). The reaction mixture was heated under microwave irradiation at 110° C. for 30 minutes. The mixture was cooled down to room temperature and evaporated to dryness. The residue was purified on silica gel by flash column chromatography to afford the title compound as an orange solid (49 mg, 18% yield).

Workup

  1. temperatureThe mixture was cooled down to room temperature
  2. customevaporated to dryness
  3. customThe residue was purified on silica gel by flash column chromatography

Sources & evidence

ORD record
ord-b3222dfcbb7a468bae6daf41829847d9
Source dataset
uspto-grants-2014_06
Patent number
US08741931B2

Reaction notes

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