Trifluoroacetic acid methylene chloride → 1-[3-(4-Amino-7-piperidin-4-yl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-phenyl]-3-(3,5-dichloro-phenyl)-urea

HRID 916787

Reaktionsgleichung

Reaktionsgleichung von HRID 916787
C(O)(C(F)(F)F)=O.C(Cl)Cl.C(OC([N:18]1[CH2:23][CH2:22][CH:21]([N:24]2[C:28]3[N:29]=[CH:30][N:31]=[C:32]([NH2:33])[C:27]=3[C:26]([C:34](=[O:53])[C:35]3[CH:40]=[CH:39][CH:38]=[C:37]([NH:41][C:42]([NH:44][C:45]4[CH:50]=[C:49]([Cl:51])[CH:48]=[C:47]([Cl:52])[CH:46]=4)=[O:43])[CH:36]=3)=[CH:25]2)[CH2:20][CH2:19]1)=O)(C)(C)C>C(Cl)Cl>[NH2:33][C:32]1[C:27]2[C:26]([C:34]([C:35]3[CH:36]=[C:37]([NH:41][C:42]([NH:44][C:45]4[CH:50]=[C:49]([Cl:51])[CH:48]=[C:47]([Cl:52])[CH:46]=4)=[O:43])[CH:38]=[CH:39][CH:40]=3)=[O:53])=[CH:25][N:24]([CH:21]3[CH2:20][CH2:19][NH:18][CH2:23][CH2:22]3)[C:28]=2[N:29]=[CH:30][N:31]=1

Komponenten

4

Edukt 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 672191604-(4-Amino-5-{3-[3-(3,5-dichloro-phenyl)-ureido]-benzoyl}-pyrrolo[2,3-d]pyrimidin-7-yl)-piperidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 672198621-[3-(4-Amino-7-piperidin-4-yl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-phenyl]-3-(3,5-dichloro-phenyl)-ureaAusbeute 95,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of TFA/CH2Cl2 (0.49 mL/3.5 mL) was added to a solution of 4-(4-amino-5-{3-[3-(3,5-dichloro-phenyl)-ureido]-benzoyl}-pyrrolo[2,3-d]pyrimidin-7-yl)-piperidine-1-carboxylic acid tert-butyl ester (0.2 g, 0.32 mmol) in CH2Cl2 (1 mL) at 0 C. The reaction mixture was warmed to room temperature, stirred for 12 h, and concentrated in vacuo. The crude reaction mixture was quenched with H2O (5 mL) and Na2CO3 (5 mL) and extracted with CH2Cl2 (4×5 mL). The combined organic extracts were dried (MgSO4), filtered, and concentrated in vacuo to provide the title compound as a yellow solid (0.16 g, 93%). MS: 525.5 (MH+); HPLC Rf: 5.35 min. (HPLC method 4); HPLC purity: 84%.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. customThe crude reaction mixture
  3. customwas quenched with H2O (5 mL) and Na2CO3 (5 mL)
  4. extractionextracted with CH2Cl2 (4×5 mL)
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d8ca7405ea6f4f99bbe217c03b7512c4
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07271262B2

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