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

HRID 1929374Notes

Reaction equation

HRID 1929374 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-f212d000ca7040d9ba6d89cac5765b55
Source dataset
uspto-grants-2012_05
Patent number
US08188071B2

Reaction notes

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