Triethylamine → 1-[2-(2-Chlorophenyl)-3-iodopyrazolo[1,5-a]pyrimidin-7-yl]-4-ethylaminopiperidine-4-carboxylic Acid Amide

HRID 348026Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 348026
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]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:26]([NH:28][C:29]1([C:35]([NH2:37])=[O:36])[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)[CH3:27]>C(O)C.C(Cl)Cl>[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]=[CH:4][CH:3]=[C:2]([N:32]3[CH2:31][CH2:30][C:29]([NH:28][CH2:26][CH3:27])([C:35]([NH2:37])=[O:36])[CH2:34][CH2:33]3)[N:7]2[N:8]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 965734-(Ethylamino)piperidine-4-carboxamideHCID 21083717HCID 21083717, Verbindung

Produkt 1

HCID 588013111-[2-(2-Chlorophenyl)-3-iodopyrazolo[1,5-a]pyrimidin-7-yl]-4-ethylaminopiperidine-4-carboxylic Acid AmideAusbeute 86,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21584144Dichloromethane ethanolLösungsmittel

Versuchsvorschrift

To a solution of 7-chloro-2-(2-chlorophenyl)-3-iodopyrazolo[1,5-a]pyrimidine (I-1A-1d; 80 mg, 0.21 mmol) and triethylamine (44 μl, 0.32 mmol) in 1:1 ethanol/methylene chloride (2 ml) was added 4-ethylaminopiperidine-4-carboxylic acid amide (I-1A-1g; 40 mg, 0.23 mmol). A colorless precipitate formed after several minutes and the mixture was stirred overnight. The solid precipitate was isolated by vacuum filtration, washed with ethanol and ether, and then dried, in vacuo, to afford product I-1A-1h as an off-white solid (95 mg, 86%): +APcI MS (M+1) 525.4; 1H NMR (400 MHz, CD3OD) δ 8.27 (d, J=5.4 Hz, 1H), 7.55 (d, J=7.5 Hz, 1H), 7.48–7.39 (m, 3H), 6.45 (d, J=5.6 Hz, 1H), 4.14–3.96 (m, 2H), 3.92–3.84 (m, 2H), 2.50 (q, J=7.1 Hz, 2H), 2.23–2.15 (m, 2H), 1.85–1.77 (m, 2H), 1.16 (t, J=7.1 Hz, 3H).

Aufarbeitung

  1. customA colorless precipitate formed after several minutes
  2. customThe solid precipitate was isolated by vacuum filtration
  3. washwashed with ethanol and ether
  4. customdried, in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e39ffc333d784b1fb85888f75b243bf4
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176210B2

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