Triethylamine → HCID 59589525, compound

HRID 1971543Notes

Reaction equation

HRID 1971543 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-05c00c503f1849f1aa5df423fc0f9739
Source dataset
uspto-grants-2013_04
Patent number
US08431596B2

Reaction notes

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