1-Methyl-1H-benzimidazol-6-amine → [7-(4-Methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-(3-methyl-3H-benzimidazol-5-yl)-amine

HRID 1262364Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1262364
CS([C:4]1[N:9]=[CH:8][C:7]2=[CH:10][CH:11]=[C:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=3)[N:6]2[N:5]=1)=O.[CH3:23][N:24]1[C:28]2[CH:29]=[C:30]([NH2:33])[CH:31]=[CH:32][C:27]=2[N:26]=[CH:25]1>>[CH3:22][S:19]([C:16]1[CH:17]=[CH:18][C:13]([C:12]2[N:6]3[C:7]([CH:8]=[N:9][C:4]([NH:33][C:30]4[CH:31]=[CH:32][C:27]5[N:26]=[CH:25][N:24]([CH3:23])[C:28]=5[CH:29]=4)=[N:5]3)=[CH:10][CH:11]=2)=[CH:14][CH:15]=1)(=[O:21])=[O:20]

Komponenten

3

Edukt 2

HCID 136802831-Methyl-1H-benzimidazol-6-amineHCID 66711046HCID 66711046, Verbindung

Produkt 1

HCID 66712281[7-(4-Methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-(3-methyl-3H-benzimidazol-5-yl)-amine

Versuchsvorschrift

Following the synthetic and purification procedures described in Example 1293d, 2-methanesulfinyl-7-(4-methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazine (75 mg, 0.22 mmol) was coupled with 3-methyl-3H-benzimidazol-5-ylamine (57 mg, 0.38 mmol) at 105° C. for 86 h to afford the title compound. Yield of TFA salt: 12 mg (10%) of brown powder. LC/MS: 419 (M+H); HPLC: 95% pure, RT=2.21 min; mp: lyophilyte; 1H NMR: (DMSO, δ) 10.11 (s, 1H), 9.33 (s, 1H), 9.14 (s, 1H), 8.43 (d, J=8.6, 2H), 8.40 (s, 1H), 8.11 (d, J=8.6, 2H), 7.81 (d, J=9.0, 1H), 7.70 (d, J=9.0, 1H), 7.34 (d, J=4.9, 1H), 7.08 (d, J=4.9, 1H), 3.85 (s, 3H), 3.30 (s, 3H).

Aufarbeitung

  1. custompurification procedures

Quellen und Nachweise

ORD-Eintrag
ord-274c85c100e44ee697681a5310d75f21
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08471005B2

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