Ammonium formate → HCID 67513904, compound

HRID 473889Notes

Reaction equation

HRID 473889 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([N:10]2[CH2:16][C:15]3[CH:17]=[C:18]([C:21]4[CH:22]=[C:23]([N+:28]([O-])=O)[C:24]([NH2:27])=[N:25][CH:26]=4)[CH:19]=[CH:20][C:14]=3[O:13][CH2:12][CH2:11]2)=[O:9])[CH2:4][CH2:3]1.C([O-])=O.[NH4+]>[Pd].C(O)C>[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([N:10]2[CH2:16][C:15]3[CH:17]=[C:18]([C:21]4[CH:22]=[C:23]([NH2:28])[C:24]([NH2:27])=[N:25][CH:26]=4)[CH:19]=[CH:20][C:14]=3[O:13][CH2:12][CH2:11]2)=[O:9])[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 67515434HCID 67515434, compound

Product 1

HCID 67513904HCID 67513904, compoundYield 73.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a slurry of 5-{-4-[(4-methylpiperidin-1-yl)carbonyl]-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl}-3-nitropyridin-2-amine (1.0 g, 2.4 mmol), 10% Pd—C (0.1 g) and ethanol (15 mL) was added ammonium formate (1.5 g, 24 mmol) portionwise over 1 hour. The reaction mixture was stirred for an additional hour and the catalyst was removed by filtration. Concentration of the filtrate followed by purification by silica gel column chromatography (0-5% methanol in dichloromethane) provided 5-{4-[(4-methylpiperidin-1-yl)carbonyl]-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl}pyridine-2,3-diamine (0.67 g, 72% yield) as a pale yellow foam. MS (EI) for C21H27N5O2: 382 (MH+)

Workup

  1. customthe catalyst was removed by filtration
  2. customConcentration of the filtrate followed by purification by silica gel column chromatography (0-5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-e7b03806202a435bb7e9a562227def12
Source dataset
uspto-grants-2014_01
Patent number
US08637499B2

Reaction notes

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