Hydrochloric Acid → 4-Amino-2-[(2-{[7-(2,4-dichlorophenyl)imidazo[1,2-c]pyrimidin-5-yl]amino}ethyl)amino]-1,3-thiazole-5-carbonitrile

HRID 2389825Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2389825
Cl[C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[CH:5]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[Cl:18])[N:3]=1.FC(F)(F)C(O)=O.[NH2:26][C:27]1[N:28]=[C:29]([NH:34][CH2:35][CH2:36][NH2:37])[S:30][C:31]=1[C:32]#[N:33].CCN(C(C)C)C(C)C.Cl>O.CS(C)=O>[NH2:26][C:27]1[N:28]=[C:29]([NH:34][CH2:35][CH2:36][NH:37][C:2]2[N:7]3[CH:8]=[CH:9][N:10]=[C:6]3[CH:5]=[C:4]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=3[Cl:18])[N:3]=2)[S:30][C:31]=1[C:32]#[N:33]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 59312932HCID 59312932, VerbindungHCID 86635024HCID 86635024, Verbindung

Produkt 1

HCID 593130724-Amino-2-[(2-{[7-(2,4-dichlorophenyl)imidazo[1,2-c]pyrimidin-5-yl]amino}ethyl)amino]-1,3-thiazole-5-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

214.27 mg (0.72 mmol) of chloropyrimidine (Example 6A) are introduced into 28 ml of dry DMSO, 320 mg (1.08 mmol) of 4-amino-2-[(2-aminoethyl)amino]-1,3-thiazole-5-carbonitrile trifluoroacetate (Example 20A) and 742 mg (5.74 mmol) of DIPEA are added, and the mixture is heated at 120° C. under argon for 16 h. Water is added, and the mixture is neutralized with 1N hydrochloric acid and extracted three times with ethyl acetate. The combined organic phases are freed of solvent, and the residue is purified by preparative HPLC. 48.4 mg (14% of theory) of the product are obtained as a solid.

Aufarbeitung

  1. additionare added
  2. extractionextracted three times with ethyl acetate
  3. customthe residue is purified by preparative HPLC
  4. custom48.4 mg (14% of theory) of the product are obtained as a solid

Quellen und Nachweise

ORD-Eintrag
ord-61332eb598214544bfce6b7e5be78ba7
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08273752B2

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