Diisopropylethylamine → HCID 59276173, compound

HRID 2070898Notes

Reaction equation

HRID 2070898 reaction equation
C(OC([N:8]([C:26](OC(C)(C)C)=O)[C:9]1[N:25]=[C:12]2[CH:13]=[CH:14][CH:15]=[C:16]([CH2:17][N:18]3[CH2:23][CH2:22][NH:21][C:20](=[O:24])[CH2:19]3)[N:11]2[N:10]=1)=O)(C)(C)C.CS(OS(C)(=O)=O)(=O)=O.C(OC(N(C(OC(C)(C)C)=O)[C:50]1[N:60]=[C:53]2[CH:54]=[CH:55][CH:56]=[C:57](CO)[N:52]2N=1)=O)(C)(C)C.C(N(CC)C(C)C)(C)C.N1CCNCC1=O>ClCCl>[NH:52]1[C:53]2=[N:60][CH:50]=[C:26]([NH:8][C:9]3[N:25]=[C:12]4[CH:13]=[CH:14][CH:15]=[C:16]([CH2:17][N:18]5[CH2:23][CH2:22][NH:21][C:20](=[O:24])[CH2:19]5)[N:11]4[N:10]=3)[CH:54]=[C:55]2[CH:56]=[CH:57]1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 81560Methanesulfonic anhydrideHCID 231360Piperazin-2-oneHCID 68586804HCID 68586804, compoundHCID 68588828HCID 68588828, compound

Product 1

HCID 59276173HCID 59276173, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N,N-Di-tert-butoxycarbonyl-5-((3-oxopiperazinyl)methyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine. Methanesulfonic anhydride (0.374 g, 2.147 mmol) was added to a stirred solution of N,N-di-tert-butoxycarbonyl-5-hydroxymethyl-[1,2,4]triazolo[1,5-a]pyridin-2-amine (0.652 g, 1.789 mmol) and N,N-diisopropylethylamine (0.935 mL, 5.37 mmol) in dichloromethane (15 mL). The resulting light yellow solution was stirred at room temperature under nitrogen for 30 min and then piperazin-2-one (0.269 g, 2.68 mmol) was added. The resulting mixture was stirred and heated at 50° C. under a reflux condenser under nitrogen for 5.5 h. The resulting mixture was purified using flash chromatography (Biotage) (0-10% methanol in dichloromethane) to give the desired product (0.764 g, 1.711 mmol, 96% yield) as a white foam-solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm) 7.71-7.83 (m, 3H), 7.31 (dd, J=1.37, 6.83 Hz, 1H), 4.08 (s, 2H), 3.17-3.23 (m, 2H), 3.14 (s, 2H), 2.74 (t, J=5.47 Hz, 2H), 1.40 (s, 18H); MS (ESI) m/z 447.3 [M+1]+.

Workup

  1. stirringThe resulting mixture was stirred
  2. temperatureheated at 50° C. under a reflux condenser under nitrogen for 5.5 h
  3. customThe resulting mixture was purified

Sources & evidence

ORD record
ord-6c3077ac9d874a0ca76e1e3e359cfdc3
Source dataset
uspto-grants-2012_10
Patent number
US08299056B2

Reaction notes

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