Diisopropylethylamine → HCID 59276353, compound

HRID 2070901Notes

Reaction equation

HRID 2070901 reaction equation
Br[C:2]1[N:18]=[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([CH2:10][N:11]3[CH2:16][CH2:15][NH:14][C:13](=[O:17])[CH2:12]3)[N:4]2[N:3]=1.[CH3:19]S(OS(C)(=O)=O)(=O)=O.BrC1N=C2C=CC=C([CH2:37][OH:38])N2N=1.[CH:40]([N:43]([CH2:47][CH3:48])[CH:44]([CH3:46])C)([CH3:42])C.[NH:49]1[CH2:54][CH2:53][NH:52]CC1=O>CN(C)C=O>[OH:38][CH:37]1[CH2:46][CH2:44][N:43]([C:40]2[N:49]=[CH:54][C:53]([NH:52][C:2]3[N:18]=[C:5]4[CH:6]=[CH:7][CH:8]=[C:9]([CH2:10][N:11]5[CH2:16][CH2:15][NH:14][C:13](=[O:17])[CH2:12]5)[N:4]4[N:3]=3)=[CH:19][CH:42]=2)[CH2:47][CH2:48]1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 81560Methanesulfonic anhydride2×HCID 231360Piperazin-2-oneHCID 59276171HCID 59276171, compoundHCID 68585877HCID 68585877, compound

Product 1

HCID 59276353HCID 59276353, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-((2-Bromo-[1,2,4]triazolo[1,5-a]pyridin-5-yl)methyl)piperazin-2-one. Methanesulfonic anhydride (0.083 g, 0.479 mmol) was added to a stirred solution of (2-bromo-[1,2,4]triazolo[1,5-a]pyridin-5-yl)methanol (0.095 g, 0.417 mmol) and N,N-diisopropylethylamine (0.218 mL, 1.250 mmol) in N,N-dimethylformamide (2.5 mL). The resulting clear yellow solution was capped and stirred at room temperature. After 40 min more methanesulfonic anhydride (18 mg, 0.103 mmol) was added. The resulting clear yellow solution was capped and stirred at room temperature for an additional 30 min. piperazin-2-one (0.092 g, 0.916 mmol) was added and the resulting clear yellow solution was sealed and stirred at 50° C. for 3.5 h. The resulting mixture was purified using flash chromatography (Biotage) (0-15% methanol in dichloromethane) to give the desired product (0.121 g, 0.390 mmol, 94% yield) as a white solid with some yellow impurity. 1H NMR (400 MHz, DMSO-d6) δ (ppm) 7.84 (br s, 1H), 7.72-7.80 (m, 2H), 7.26-7.34 (m, 1H), 4.08 (s, 2H), 3.18-3.26 (m, 2H), 3.16 (s, 2H), 2.69-2.79 (m, 2H); MS (ESI) m/z 310.0 [M]+, 311.8 [M+2]+.

Workup

  1. customThe resulting clear yellow solution was capped
  2. customThe resulting clear yellow solution was capped
  3. additionwas added
  4. customthe resulting clear yellow solution was sealed
  5. stirringstirred at 50° C. for 3.5 h
  6. customThe resulting mixture was purified

Sources & evidence

ORD record
ord-2438ca3099ea4c8887c6469726ceb59b
Source dataset
uspto-grants-2012_10
Patent number
US08299056B2

Reaction notes

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