Chloroform methanol → [1-(5-Amino-pyridin-2-yl)-1-methyl-ethyl]carbamic acid tert-butyl ester

HRID 55885Notes

Reaction equation

HRID 55885 reaction equation
[C:1]([O:5][C:6](=[O:32])[NH:7][C:8]([C:11]1[CH:16]=[CH:15][C:14]([N:17](CC2C=CC=CC=2)CC2C=CC=CC=2)=[CH:13][N:12]=1)([CH3:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2].CO.C(Cl)(Cl)Cl>CO.[OH-].[OH-].[Pd+2]>[C:1]([O:5][C:6](=[O:32])[NH:7][C:8]([C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][N:12]=1)([CH3:10])[CH3:9])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 21584188Chloroform methanolHCID 90356826[1-(5-Dibenzylamino-pyridin-2-yl)-1-methyl-ethyl]carbamic acid tert-butyl ester

Product 1

HCID 90369770[1-(5-Amino-pyridin-2-yl)-1-methyl-ethyl]carbamic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 42 (700 mg, 1.6 mmol) in methanol (30 mL) was added 20% Pd(OH)2 (1.25 g) and hydrogenated at 50 psi for 16 h. The reaction mixture was filtered through a pad of Celite and the filtrate was evaporated. The crude compound was purified by silica gel column chromatography (100-200 mesh, eluting with 5% MeOH/CHCl3) to obtain A4-13 (250 mg, 61%) as a white solid. Rf: 0.3 (10% MeOH/CHCl3), (m/z): 252 [MH]+; 1H NMR (400 MHz, DMSO-d6): δ 7.81 (1H, d, J=2.8 Hz), 7.08 (1H, d, J=8.4 Hz), 6.99 (1H, br s), 6.89 (1H, dd, J=2.4, 8.4 Hz), 5.11 (2H, br s), 1.45 (6H, s), 1.34 (9H, s).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. customthe filtrate was evaporated
  3. customThe crude compound was purified by silica gel column chromatography (100-200 mesh, eluting with 5% MeOH/CHCl3)
  4. customto obtain A4-13 (250 mg, 61%) as a white solid

Sources & evidence

ORD record
ord-a66f70b9cb0143e6b3e2c7d1889c3514
Source dataset
uspto-grants-2016_09
Patent number
US09433622B2

Reaction notes

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