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

HRID 1988744Notes

Reaction equation

HRID 1988744 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].N1[CH:18]=[CH:17]C=CC=1.CN(C=[O:23])C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[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:17](=[O:23])[CH3:18]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 223799826-Propyl-pyridine-3,4-diamine hydrochloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 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, AC20 (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 saturated 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. additionNext, AC20 (0.104 mL, 1.1 mmol) is added
  2. extractionextracted thrice with CH2Cl2
  3. dry with materialThe combined extracts are dried over K2CO3
  4. concentrationconcentrated to 114 mg of crude N-(4-amino-6-propyl-pyridin-3-yl)-acetamide, which
  5. customwas used without further purification

Sources & evidence

ORD record
ord-ae24178d7ee3457b96436ee3855d2a67
Source dataset
uspto-grants-2010_01
Patent number
US07642267B2

Reaction notes

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