Diisopropylethylamine → 1-[7-(2-Chlorophenyl)-8-(4-chlorophenyl)-2-methylpyrazolo[1,5-a][1,3,5]triazin-4-yl]-3-isopropylaminoazetidine-3-carboxylic Acid Amide

HRID 2054415Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2054415
Cl.[CH:2]([NH:5][C:6]1([C:10]([NH2:12])=[O:11])[CH2:9][NH:8][CH2:7]1)([CH3:4])[CH3:3].Cl[C:14]1[N:19]2[N:20]=[C:21]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[Cl:36])[C:22]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)=[C:18]2[N:17]=[C:16]([CH3:37])[N:15]=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[Cl:36][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[C:21]1[C:22]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)=[C:18]2[N:17]=[C:16]([CH3:37])[N:15]=[C:14]([N:8]3[CH2:9][C:6]([NH:5][CH:2]([CH3:4])[CH3:3])([C:10]([NH2:12])=[O:11])[CH2:7]3)[N:19]2[N:20]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 467351463-(Isopropylamino)azetidine-3-carboxamide hydrochlorideHCID 59655729HCID 59655729, Verbindung

Produkt 1

HCID 113067861-[7-(2-Chlorophenyl)-8-(4-chlorophenyl)-2-methylpyrazolo[1,5-a][1,3,5]triazin-4-yl]-3-isopropylaminoazetidine-3-carboxylic Acid Amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of 3-isopropylaminoazetidine-3-carboxylic acid amide hydrochloride salt (I-3A-1c; 72 mg, 0.361 mmol) and 4-chloro-7-(2-chlorophenyl)-8-(4-chlorophenyl)-2-methylpyrazolo[1,5-a][1,3,5]triazine (I-2A-1b; 102 mg, 0.261 mmol) in methylene chloride (1.3 ml) was added diisopropylethylamine (0.16 ml, 0.91 mmol), dropwise. After stirring for 90 minutes, the reaction was extracted from saturated aqueous NaHCO3 with methylene chloride. The combined extracts were dried (MgSO4), concentrated, in vacuo, and then purified on a Biotage™ Flash 12M column using 0-5% methanol in methylene chloride as eluant. The resultant solid was triturated from methanol and then dried, in vacuo, to afford 3A-1 (104 mg, 78%) as a colorless solid: +ESI MS (M+1) 510.1; 1H NMR (400 MHz, CD2Cl2) δ 7.47-7.34 (m, 6H), 7.21 (d, J=8.7 Hz, 2H), 6.96 (br s, 1H), 5.42 (br s, 1H), 5.22 (br m, 1H), 4.73 (br m, 2H), 4.18 (br m, 1H), 3.11 (septuplet, J=6.2 Hz, 1H), 2.48 (s, 3H), 1.06 (d, J=6.2 Hz, 6H).

Aufarbeitung

  1. extractionthe reaction was extracted from saturated aqueous NaHCO3 with methylene chloride
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. concentrationconcentrated, in vacuo
  4. custompurified on a Biotage™ Flash 12M column
  5. customThe resultant solid was triturated from methanol
  6. customdried, in vacuo
  7. customto afford 3A-1 (104 mg, 78%) as a colorless solid

Quellen und Nachweise

ORD-Eintrag
ord-7e69445fa70b4f41a4754b487ba84fad
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07329658B2

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