Sulfuric Acid → 7-(4-fluorophenyl)-N2-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)-N4-methyl-6,7-dihydro-5H-cyclopenta(d)pyrimidine-2,4-diamine

HRID 475892

Reaktionsgleichung

Reaktionsgleichung von HRID 475892
Cl[C:2]1[N:3]=[C:4]([NH:18][CH3:19])[C:5]2[CH2:10][CH2:9][CH:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[C:6]=2[N:7]=1.[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH:26]=[CH:27][C:28]=1[N:29]1[CH:33]=[N:32][C:31]([CH3:34])=[N:30]1)[NH2:25].OS(O)(=O)=O.C([O-])(O)=O.[Na+]>CN1CCCC1=O.O>[F:17][C:14]1[CH:15]=[CH:16][C:11]([CH:8]2[C:6]3[N:7]=[C:2]([NH:25][C:24]4[CH:26]=[CH:27][C:28]([N:29]5[CH:33]=[N:32][C:31]([CH3:34])=[N:30]5)=[C:22]([O:21][CH3:20])[CH:23]=4)[N:3]=[C:4]([NH:18][CH3:19])[C:5]=3[CH2:10][CH2:9]2)=[CH:12][CH:13]=1

Komponenten

7

Edukt 4

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 580758122-chloro-7-(4-fluorophenyl)-N-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-amineHCID 595778183-Methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)aniline

Produkt 1

HCID 580753177-(4-fluorophenyl)-N2-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)-N4-methyl-6,7-dihydro-5H-cyclopenta(d)pyrimidine-2,4-diamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 2-chloro-7-(4-fluorophenyl)-N-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-amine (Preparation Hh) (141.2 mg, 0.508 mmol) and 3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)aniline (Preparation D) (208 mg, 1.017 mmol) in N-Methyl-2-pyrrolidinone (4067 μL) was added H2SO4 (43.4 μL, 0.813 mmol). The solution was heated to 100° C. When the reaction was complete, water and NaHCO3 were added. After extraction into CH2Cl2, the organic extracts were dried over MgSO4, filtered, and concentrated in vacuo. Applied the residue to SG and eluted with a EtOAc/Hex gradient, which yielded 7-(4-fluorophenyl)-N2-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)-N4-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine-2,4-diamine (Example 44).

Aufarbeitung

  1. extractionAfter extraction into CH2Cl2
  2. dry with materialthe organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. washApplied the residue to SG and eluted with a EtOAc/Hex gradient, which

Quellen und Nachweise

ORD-Eintrag
ord-703d6d2a1ddb42ef9b8fab5727535276
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637525B2

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