1-((1,1-DIMETHYLETHOXY)CARBONYL)-4-(3-((1-METHYLETHYL)AMINO)-2-PYRIDYL)PIPERAZINE synthesis

6synthesis methods

Product Name:1-((1,1-DIMETHYLETHOXY)CARBONYL)-4-(3-((1-METHYLETHYL)AMINO)-2-PYRIDYL)PIPERAZINE
CAS Number:136818-14-9
Molecular formula:C17H28N4O2
Molecular Weight:320.43

3-Amino-2-[4-butoxycarbonyl(piperazino)]pyridine

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1-((1,1-DIMETHYLETHOXY)CARBONYL)-4-(3-((1-METHYLETHYL)AMINO)-2-PYRIDYL)PIPERAZINE

136818-14-9
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Yield:136818-14-9 100%

Reaction Conditions:

Stage #1: 1-[1,1-dimethylethoxycarbonyl]-4-[3-amino-2-pyridinyl]piperazine;acetonewith acetic acid in 1,2-dichloro-ethane at 20; for 0.166667 h;
Stage #2: with sodium tris(acetoxy)borohydride in 1,2-dichloro-ethane at 20; for 64 h;

Steps:

1 Synthesis of mPEGn-O-Delavirdine Conjugates

3-amino-2-(Boc-piperazine)pyridine 7 (3.813 g, about 11.16 mmol, crude) was dissolved in dichloroethane (75 mL).
Acetone (1.7 mL, 23.12 mmol) was added, followed by an addition of HOAc (1.0 mL, 17.45 mmol) at room temperature.
After about 10 min, NaBH(OAc)₃ (7.46 g, 33.44 mmol) was added.
An additional amount of dichloroethane (25 mL) was added.
The resulting mixture was stirred at room temperature for 64 h.
5% aqueous NaHCO₃ was added to quench the reaction.
The organic phase was separated and the aqueous phase was extracted with dichloromethane (2*50 mL).
The combined organic solution was washed with brine, dried over anhydrous Na₂SO₄, concentrated.
The residue was purified via flash column chromatography over silica gel with 5-35% ethyl acetate in hexane to afford the product as solid in quantitative yield. ¹H-NMR (CDCl₃): 7.673 (dd, J=5.0 Hz and 1.5 Hz, 1 H, Ar-H), 6.904 (dd, J=8.0 Hz and 5.0 Hz, 1 H, Ar-H), 6.812 (dd, J=8.0 Hz and 1.5 Hz, 1 H, Ar-H), 4.150 (d, J=7.5 Hz, 1 H, NH), 3.569-3.517 (m, 5 H, 2CH₂ and CH), 2.997 (t, J=5.0 Hz, 4 H, 2 CH₂), 1.477 (s, 9 H, 3 CH₃), 1.23 (d, J=6.0 Hz, 6 H, 2 CH₃).
(ref.
Romero D. L. et al. J. Med. Chem. 37, 999-1014, 1994.)
Synthesis of 2-piperazinyl-3-(isopropylamino)pyridine 8: