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Triethylamine → (R)-(4-(1-chloropyrido[3,4-d]pyridazin-4-yl)-3-methylpiperazin-1-yl)(4,4-difluorocyclohexyl)methanone

HRID 1514388
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1514388
[F:1][C:2]1([F:11])[CH2:7][CH2:6][CH:5]([C:8]([OH:10])=O)[CH2:4][CH2:3]1.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1.C(N(CC)CC)C.[Cl:34][C:35]1[N:40]=[N:39][C:38]([N:41]2[CH2:46][CH2:45][NH:44][CH2:43][C@H:42]2[CH3:47])=[C:37]2[CH:48]=[N:49][CH:50]=[CH:51][C:36]=12>CN(C=O)C>[Cl:34][C:35]1[N:40]=[N:39][C:38]([N:41]2[CH2:46][CH2:45][N:44]([C:8]([CH:5]3[CH2:4][CH2:3][C:2]([F:1])([F:11])[CH2:7][CH2:6]3)=[O:10])[CH2:43][C@H:42]2[CH3:47])=[C:37]2[CH:48]=[N:49][CH:50]=[CH:51][C:36]=12
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 27791364,4-Difluorocyclohexanecarboxylic acidHCID 57657623(R)-1-chloro-4-(2-methylpiperazin-1-yl)pyrido[3,4-d]pyridazine

Produkt 1

HCID 57657597(R)-(4-(1-chloropyrido[3,4-d]pyridazin-4-yl)-3-methylpiperazin-1-yl)(4,4-difluorocyclohexyl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

4,4-difluorocyclohexanecarboxylic acid (277 mg, 169 mmol) and bis(2-oxo-3-oxazolidinyl)phosphinic chloride (411 mg, 1.61 mmol) were stirred in DMF (3 ml) and triethylamine (0.4 ml) for 2 minutes. The solution was added to (R)-1-chloro-4-(2-methylpiperazin-1-yl)pyrido[3,4-d]pyridazine 59 (387 mg, 1.47 mmol) and washed in with an additional 1 ml DMF. The reaction was heated at 55° C. for 1.5 hours and then stirred at RT for 17 hours. The reaction was added to saturated NaHCO3 (80 ml) and extracted three times with dichloromethane (50 ml). The combined organics were dried (MgSO4) and evaporated to give a yellow solid. The residue was chromatographed over silica with a gradient of hexane and 0-100% ethyl acetate to give (R)-(4-(1-chloropyrido[3,4-d]pyridazin-4-yl)-3-methylpiperazin-1-yl)(4,4-difluorocyclohexyl)methanone 60 as a yellow solid, 236 mg. LC/MS m/z=410 (M+H+).

Aufarbeitung

  1. washwashed in with an additional 1 ml DMF
  2. additionThe reaction was added to saturated NaHCO3 (80 ml)
  3. extractionextracted three times with dichloromethane (50 ml)
  4. dry with materialThe combined organics were dried (MgSO4)
  5. customevaporated
  6. customto give a yellow solid
  7. customThe residue was chromatographed over silica with a gradient of hexane and 0-100% ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-3b739176d1b6499d86485bc8ba11eb19
Quelldatensatz
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08222251B2

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