Pyridine → N-(4-amino-6-propyl-pyridin-3-yl)-acetamide

HRID 895559Notes

Reaction equation

HRID 895559 reaction equation
Cl.[CH2:2]([C:5]1[N:10]=[CH:9][C:8]([NH2:11])=[C:7]([NH2:12])[CH:6]=1)[CH2:3][CH3:4].N1C=CC=CC=1.[CH3:19][C:20](OC(C)=O)=[O:21].C([O-])(O)=O.[Na+]>C(Cl)Cl.CN(C=O)C>[NH2:12][C:7]1[CH:6]=[C:5]([CH2:2][CH2:3][CH3:4])[N:10]=[CH:9][C:8]=1[NH:11][C:20](=[O:21])[CH3:19]

Participants

7

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 223799826-Propyl-pyridine-3,4-diamine hydrochloride

Product 1

HCID 22380205N-(4-amino-6-propyl-pyridin-3-yl)-acetamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 6-propyl-pyridine-3,4-diamine hydrochloride (prepared from ethyl butyrylacetate as described in Example 28, steps 1-9) (187 mg, 1.00 mmol) in CH2Cl2 (4 mL) at 0° C. under N2 is added pyridine (0.24 mL, 3.00 mmol) followed by DMF (2 mL) (for solubility). Next, Ac2O (0.104 mL, 1.1 mmol) is added. The reaction mixture is stirred for 3 h while slowly warming to rt. It is then poured into saturatedd aq NaHCO3 and extracted thrice with CH2Cl2. The combined extracts are dried over K2CO3 and concentrated to 114 mg of crude N-(4-amino-6-propyl-pyridin-3-yl)-acetamide, which was used without further purification. 1H NMR (CDCl3, 300 MHz) δ 8.73 (br, 1H), 8.00 (s, 1H), 8.43 (s, 1H), 4.63 (br, 2H), 2.54 (m, 2H), 2.13 (s, 3H), 1.63 (sextet, J=7.2 Hz, 2H), 0.89 (t, J=7.2 Hz, 3H) ppm. Electrospray MS: m/z 194 [M+1].

Workup

  1. extractionextracted thrice with CH2Cl2
  2. dry with materialThe combined extracts are dried over K2CO3
  3. concentrationconcentrated to 114 mg of crude N-(4-amino-6-propyl-pyridin-3-yl)-acetamide, which
  4. customwas used without further purification

Sources & evidence

ORD record
ord-bb41bab62dc747af98ae678711294b97
Source dataset
uspto-grants-2005_07
Patent number
US06916819B2

Reaction notes

Loading…