Triethylamine → HCID 11547733, Verbindung

HRID 2264585Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2264585
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[CH2:13]([N:15]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]2[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=2)[CH2:17][CH2:16]1)[CH3:14].CCN(CC)CC.[Cl:36][C:37]1[N:42]=[CH:41][N:40]=[C:39]([O:43][C:44]2[CH:45]=[C:46]3[C:50](=[CH:51][CH:52]=2)[NH:49][CH2:48][CH2:47]3)[CH:38]=1>C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+].O.CCOC(C)=O>[CH2:13]([N:15]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([NH:26][C:2]([N:49]3[C:50]4[C:46](=[CH:45][C:44]([O:43][C:39]5[CH:38]=[C:37]([Cl:36])[N:42]=[CH:41][N:40]=5)=[CH:52][CH:51]=4)[CH2:47][CH2:48]3)=[O:4])=[CH:27][CH:28]=2)[CH2:17][CH2:16]1)[CH3:14]

Komponenten

9

Edukt 4

HCID 8471Triethylamine2×HCID 94429TriphosgeneHCID 10849964-[(4-Ethylpiperazin-1-yl)methyl]anilineHCID 858916285-(6-Chloro-pyrimidin-4-yloxy)-2,3-dihydro-indole

Produkt 1

HCID 11547733HCID 11547733, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel3×HCID 8857Ethyl AcetateLösungsmittelHCID 10340Sodium CarbonateLösungsmittel

Versuchsvorschrift

104 mg (0.35 mMol) triphosgene are dissolved in 13 ml ice-cooled CH2Cl2. Then a solution of 230 mg (1.05 mMol) 4-(4-ethylpiperazin-1-ylmethyl)-aniline and 209 μl (1.50 mMol) Et3N in 6 ml CH2Cl2 is added during 8 min. After 3 additional minutes, the mixture is warmed up to rt by a water bath and then a solution of 1.0 mMol 5-(6-chloro-pyrimidin-4-yloxy)-2,3-dihydro-1H-indole (Step 14.1) and 139 μl (1.00 mMol) Et3N in 6 ml CH2Cl2 is added during 8 min. After 2 h at rt, the mixture is diluted with sat. Na2CO3 solution/water 1:1 and EtOAc, the aqueous phase separated off and extracted twice with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated. Crystallization from DIPE gives the title compound: MS: [M+1]+=493/495; TLC(CH2Cl2/MeOH/NH3conc. 90:10:1): Rf=0.24; HPLC: AtRet=10.5.

Aufarbeitung

  1. customthe aqueous phase separated off
  2. extractionextracted twice with EtOAc
  3. washThe organic layers are washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customCrystallization from DIPE

Quellen und Nachweise

ORD-Eintrag
ord-e0d9f1ccb0ff467b8c8c1212df34eb08
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07855215B2

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