Triethylamine → HCID 59589525, compound

HRID 1054356Notes

Reaction equation

HRID 1054356 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[N:24]=[C:9]2[CH:10]=[CH:11][CH:12]=[C:13]([C:14]3[CH:23]=[CH:22][C:17]4[O:18][CH2:19][CH2:20][O:21][C:16]=4[CH:15]=3)[N:8]2[N:7]=1)=[O:4].C(N(CC)CC)C.[CH3:32][N:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1>ClCCl>[O:18]1[C:17]2[CH:22]=[CH:23][C:14]([C:13]3[N:8]4[N:7]=[C:6]([NH:5][C:3](=[O:4])[CH2:2][N:36]5[CH2:37][CH2:38][N:33]([CH3:32])[CH2:34][CH2:35]5)[N:24]=[C:9]4[CH:10]=[CH:11][CH:12]=3)=[CH:15][C:16]=2[O:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 59590109HCID 59590109, compound

Product 1

HCID 59589525HCID 59589525, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-chloro—N-[5-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-acetamide (0.1 g, 0.29 mmol) in dichloromethane (2 mL), triethylamine (0.061 mL, 0.43 mmol) and N-methylpiperazine (0.036 mL, 0.32 mmol) were added successively and the mixture was stirred overnight. The solvent was removed under reduced pressure and the crude then purified by prep LCMS. LCMS Method: 2, RT=2.19 min, MI=409 [M+1], NMR 1H (DMSO): 2.29 (s, 3H), 2.48-2.50 (m, 4H), 2.53-2.58 (m, 4H), 3.25 (brs, 2H), 4.33 (brs, 4H), 7.03 (d, 1H), 7.25 (dd, 1H), 7.47 (dd, 1H), 7.62-7.71 (m, 3H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude then purified by prep LCMS

Sources & evidence

ORD record
ord-4010879e486141e2b41b25213316ffb4
Source dataset
uspto-grants-2016_07
Patent number
US09394301B2

Reaction notes

Loading…