Methanol → 1-{3-[(4-aminopyrrolo[2,1-f][1,2,4]triazin-5-yl)carbonyl]phenyl}-3-(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)urea

HRID 2108358Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2108358
[NH2:1][C:2]1[C:7]2=[C:8]([C:12]([C:14]3[CH:15]=[C:16]([NH:20][C:21]([NH:23][C:24]4[N:28]([CH3:29])[N:27]=[C:26]([CH:30]5[CH2:32][CH2:31]5)[CH:25]=4)=[O:22])[CH:17]=[CH:18][CH:19]=3)=[O:13])[CH:9]=[C:10](Br)[N:6]2[N:5]=[CH:4][N:3]=1.CO>CCOC(C)=O.[Pd]>[NH2:1][C:2]1[C:7]2=[C:8]([C:12]([C:14]3[CH:15]=[C:16]([NH:20][C:21]([NH:23][C:24]4[N:28]([CH3:29])[N:27]=[C:26]([CH:30]5[CH2:32][CH2:31]5)[CH:25]=4)=[O:22])[CH:17]=[CH:18][CH:19]=3)=[O:13])[CH:9]=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1

Komponenten

5

Edukt 2

HCID 887MethanolHCID 167397611-{3-[(4-amino-7-bromopyrrolo[2,1-f][1,2,4]triazin-5-yl)carbonyl]phenyl}-3-(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)urea

Produkt 1

HCID 576294761-{3-[(4-aminopyrrolo[2,1-f][1,2,4]triazin-5-yl)carbonyl]phenyl}-3-(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)urea

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The above crude 99A was dissolved in EtOAc (20 mL) and MeOH (20 mL) and treated with 10% Pd/C. The reaction mixture was stirred under a hydrogen atmosphere for 4.5 hours and then filtered to remove the catalyst. The filtrate was concentrated and the resulting solid was collected by filtration, rinsed with EtOAc and dried to give the desired product (23 mg). Compound 99B had an analytical HPLC retention time=2.433 min. (Chromolith SpeedROD column 4.6×50 mm, 10%-90% aqueous methanol over 4 minutes containing 0.1% TFA, 4 ml/min, monitoring at 220 nm) and a LC/MS M++1=417+.

Aufarbeitung

  1. filtrationfiltered
  2. customto remove the catalyst
  3. concentrationThe filtrate was concentrated
  4. filtrationthe resulting solid was collected by filtration
  5. washrinsed with EtOAc
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-36660a6ed9bf474389d37f85a23ad5fc
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07514435B2

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