Diisopropylethylamine → Ammonium Hydroxide

HRID 1027887Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1027887
FC(F)(F)C(O)=[O:4].[CH2:8]([N:15]1[CH2:23][CH2:22][CH2:21][C:17]2([CH2:20][NH:19][CH2:18]2)[CH2:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CC1C=CC(S(O[C:35]2[C:36]3[CH2:46][CH2:45][CH2:44][C:43]4[CH:47]=[CH:48][CH:49]=[CH:50][C:42]=4[C:37]=3[N:38]=[C:39]([NH2:41])[N:40]=2)(=O)=O)=CC=1.C(N(CC)C(C)C)(C)C>COCCO.C(Cl)Cl>[OH-:4].[NH4+:15].[CH2:8]([N:15]1[CH2:23][CH2:22][CH2:21][C:17]2([CH2:20][N:19]([C:35]3[C:36]4[CH2:46][CH2:45][CH2:44][C:43]5[CH:47]=[CH:48][CH:49]=[CH:50][C:42]=5[C:37]=4[N:38]=[C:39]([NH2:41])[N:40]=3)[CH2:18]2)[CH2:16]1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Komponenten

7

Edukt 3

HCID 81531DiisopropylethylamineHCID 251291732-amino-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidin-4-yl 4-methylbenzenesulfonateHCID 692261806-Benzyl-2,6-diazaspiro[3.5]nonane 2,2,2-trifluoroacetate

Produkt 2

HCID 14923Ammonium HydroxideHCID 692254774-(6-benzyl-2,6-diazaspiro[3.5]non-2-yl)-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidin-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 80192-MethoxyethanolLösungsmittel

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

The product from Example 77A was mixed with the product from Example 59C (135 mg, 0.35 mmol) in 2-methoxyethanol (1.2 mL) and N,N-diisopropylethylamine (0.74 mL, 1.74 mmol), then heated at 115° C. overnight, then cooled, diluted with CH2Cl2, and washed with 1 M NaOH. The aqueous layer was extracted with CH2Cl2. The combined organic extracts were dried (MgSO4), filtered, concentrated and purified by chromatography on silica gel, eluting with a gradient of 1:0 to 1:2 CH2Cl2:[10% (9:1 MeOH:saturated aqueous ammonium hydroxide)] to provide the title compound. MS (M+H)+ m/z 426.

Aufarbeitung

  1. temperaturecooled
  2. washwashed with 1 M NaOH
  3. extractionThe aqueous layer was extracted with CH2Cl2
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by chromatography on silica gel
  8. washeluting with a gradient of 1:0 to 1:2 CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-206b34b43679486d8a4bbe477d93800d
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08735411B2

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