Triethylamine → 1-[7-(2-Chlorophenyl)-8-iodo-2-methylpyrazolo[1,5-a][1,3,5]triazin-4-yl]-4-ethylaminopiperidine-4-carboxylic Acid Amide

HRID 2054388Notes

Reaction equation

HRID 2054388 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:18])[C:10]([I:11])=[C:6]2[N:5]=[C:4]([CH3:19])[N:3]=1.C(N(CC)CC)C.[CH2:27]([NH:29][C:30]1([C:36]([NH2:38])=[O:37])[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)[CH3:28]>O1CCCC1>[Cl:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:9]1[C:10]([I:11])=[C:6]2[N:5]=[C:4]([CH3:19])[N:3]=[C:2]([N:33]3[CH2:32][CH2:31][C:30]([NH:29][CH2:27][CH3:28])([C:36]([NH2:38])=[O:37])[CH2:35][CH2:34]3)[N:7]2[N:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 965734-(Ethylamino)piperidine-4-carboxamideHCID 596556974-Chloro-7-(2-chlorophenyl)-8-iodo-2-methylpyrazolo[1,5-a][1,3,5]triazine

Product 1

HCID 596557211-[7-(2-Chlorophenyl)-8-iodo-2-methylpyrazolo[1,5-a][1,3,5]triazin-4-yl]-4-ethylaminopiperidine-4-carboxylic Acid AmideYield 134.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-chloro-7-(2-chlorophenyl)-8-iodo-2-methylpyrazolo[1,5-a][1,3,5]triazine (I-1A-1e; 28 mg, 0.069 mmol) and triethylamine (14 μl, 0.10 mmol) in tetrahydrofuran (1 ml) was added 4-ethylaminopiperidine-4-carboxylic acid amide (I-1A-1h; 13 mg, 0.076 mmol) and the mixture was stirred overnight. The mixture was extracted from water with ethyl acetate, the combined organic layers were washed with brine, dried (MgSO4), filtered through a 0.45 μm filter disk, and then concentrated, in vacuo, to afford the crude product (50 mg). Purification on a Chromatotron using 0-20-30% acetonitrile in methylene chloride as eluant afforded product I-1A-1i (20 mg, 54%): +APcI MS (M+1) 540.8; 1H NMR (400 MHz, CD2Cl2) δ 7.54 (d, J=7.9 Hz, 1H), 7.47-7.38 (m, 3H), 4.83-4.65 (br m, 2H), 4.20-4.05 (br m, 2H), 2.55 (q, J=7.1 Hz, 2H), 2.50 (s, 3H), 2.26-1.98 (m, 2H), 1.78-1.75 (m, 2H), 1.10 (t, J=7.1 Hz, 3H).

Workup

  1. extractionThe mixture was extracted from water with ethyl acetate
  2. washthe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered through a 0.45 μm
  5. filtrationfilter disk
  6. concentrationconcentrated, in vacuo

Sources & evidence

ORD record
ord-110ee514a12d4b7aa941b75f4b1ef537
Source dataset
uspto-grants-2008_02
Patent number
US07329658B2

Reaction notes

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