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Hydrochloric Acid → HCID 178434340, Verbindung

HRID 1038832
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1038832
C([NH:4][CH2:5][CH:6]1[CH2:10][CH2:9][N:8]([C:11]2[C:12]3[O:37][CH:36]=[CH:35][C:13]=3[N:14]=[C:15]([NH:17][C:18]3[CH:26]=[C:25]4[C:21]([C:22]([CH3:34])=[N:23][N:24]4C(OC(C)(C)C)=O)=[CH:20][CH:19]=3)[N:16]=2)[CH2:7]1)(=O)C.Cl.NCC1CCN(C(OC(C)(C)C)=O)C1.C(Cl)(=O)C.ClC1N=C(Cl)C2OC=CC=2N=1.Cl>CO>[NH2:4][CH2:5][CH:6]1[CH2:10][CH2:9][N:8]([C:11]2[C:12]3[O:37][CH:36]=[CH:35][C:13]=3[N:14]=[C:15]([NH:17][C:18]3[CH:26]=[C:25]4[C:21]([C:22]([CH3:34])=[N:23][NH:24]4)=[CH:20][CH:19]=3)[N:16]=2)[CH2:7]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 45072187tert-Butyl 3-(aminomethyl)pyrrolidine-1-carboxylate hydrochlorideHCID 457899682,4-Dichlorofuro[3,2-D]pyrimidineHCID 67130041HCID 67130041, Verbindung

Produkt 1

HCID 178434340
HCID 178434340, Verbindung
Ausbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of tert-butyl 6-(4-(3-(acetamidomethyl)pyrrolidin-1-yl)furo[3,2-d]pyrimidin-2-ylamino)-3-methyl-1H-indazole-1-carboxylate (0.57 g, 1.1 mmol, prepared using E.1 from tert-butyl 3-(aminomethyl)pyrrolidine-1-carboxylate hydrochloride [Astatech] with acetyl chloride, C, A with 2,4-dichlorofuro[3,2-d]pyrimidine [ArkPharm] and B with Example #3, Step B) in MeOH (12 mL) was added concentrated HCl (12 mL). The mixture was stirred for about 32 h at about 90° C. The mixture was cooled to rt, and a white precipitate formed that was collected by vacuum filtration and washed with water. The solid was dissolved in hot aqueous 1 M HCl and the suspension was filtered while hot. To the filtrate was added aqueous NH4OH to reach a pH˜9, and the resulting precipitate was collected to give 4-(3-(aminomethyl)pyrrolidin-1-yl)-N-(3-methyl-1H-indazol-6-yl)furo[3,2-d]pyrimidin-2-amine (0.27 g, 61%): LC/MS (Table 2, Method h) Rt=1.61 min; MS m/z: 364 (M+H)+. Syk IC50=A

Aufarbeitung

  1. temperatureThe mixture was cooled to rt
  2. customa white precipitate formed
  3. filtrationthat was collected by vacuum filtration
  4. washwashed with water
  5. dissolutionThe solid was dissolved in hot aqueous 1 M HCl
  6. filtrationthe suspension was filtered while hot
  7. additionTo the filtrate was added aqueous NH4OH
  8. customthe resulting precipitate was collected

Quellen und Nachweise

ORD-Eintrag
ord-c2b96bd7d9d049508eee901b9dcc75f3
Quelldatensatz
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08551981B2

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