Triethylamine → HCID 178522415, Verbindung

HRID 2064623Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2064623
FC(F)[O:3][C:4]1[CH:26]=[CH:25][C:7]2NC(C3C(NC(N4CCCCC4)=O)=CNN=3)=NC=2C=1.[NH:28]1[C:39]2[C:31](=[CH:32][C:33]3[CH2:34][CH2:35][CH2:36][C:37]=3[CH:38]=2)[N:30]=[C:29]1[C:40]1[C:44]([NH2:45])=[CH:43][NH:42][N:41]=1.C(N(CC)CC)C.C1(C(Cl)=O)CC1.[OH-].[K+].[Cl-].[NH4+]>O1CCCC1>[NH:30]1[C:31]2[C:39](=[CH:38][C:37]3[CH2:36][CH2:35][CH2:34][C:33]=3[CH:32]=2)[N:28]=[C:29]1[C:40]1[C:44]([NH:45][C:4]([CH:26]2[CH2:7][CH2:25]2)=[O:3])=[CH:43][NH:42][N:41]=1

Komponenten

8

Edukt 6

HCID 8471TriethylamineHCID 14797Potassium HydroxideHCID 25517Ammonium ChlorideHCID 77637Cyclopropanecarbonyl chlorideHCID 178508051HCID 178508051, VerbindungHCID 178522444HCID 178522444, Verbindung

Produkt 1

HCID 178522415HCID 178522415, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

By proceeding in a similar manner to Example 258(a) above but (i) treating a solution of 3-(1,5,6,7-tetrahydro-1,3-diaza-s-indacen-2-yl)-1H-pyrazol-4-ylamine [310 mg, Example 256(b)] and triethylamine (4 eq) in tetrahydrofuran (15 mL) with cyclopropanecarbonyl chloride (4 eq), (ii) stirring the reaction mixture at 60° C. for 2 hours, (iii) treating the resulting bis-acylated product with methanolic potassium hydroxide (20 mL, 10.05 g KOH) at 40° C. for 1 hour followed by treatment with aqueous ammonium chloride (200 mL), (iii) extracting this mixture three times with ethyl acetate (100 mL), (iv) evaporating the combined extracts and (v) chromatographing the residue on silica gel (ethyl acetate/gradient of 50-0% heptane) there was prepared cyclopropanecarboxylic acid [3-(1,5,6,7-tetrahydro-1,3-diaza-s-indacen-2-yl)-1H-pyrazol-4-yl]amide (50 mg) as a yellow solid. LC-MS (Method E) RT=2.05 minutes, 308 (M+H)+.

Aufarbeitung

  1. extractionextracting this mixture three times with ethyl acetate (100 mL), (iv)
  2. customevaporating the combined extracts and (v) chromatographing the residue on silica gel (ethyl acetate/gradient of 50-0% heptane) there
  3. customwas prepared cyclopropanecarboxylic acid [3-(1,5,6,7-tetrahydro-1,3-diaza-s-indacen-2-yl)-1H-pyrazol-4-yl]amide (50 mg) as a yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-700ab96b803142cc9a16ff22c6550e8f
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288425B2

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