1-Methyl-1H-benzimidazol-6-amine → N-tert-Butyl-3-[2-(3-methyl-3H-benzimidazol-5-ylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-benzenesulfonamide

HRID 1262363

Reaktionsgleichung

Reaktionsgleichung von HRID 1262363
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[N:23]3[C:18]([CH:19]=[N:20][C:21](S(C)=O)=[N:22]3)=[CH:17][CH:16]=2)[CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:27][N:28]1[C:32]2[CH:33]=[C:34]([NH2:37])[CH:35]=[CH:36][C:31]=2[N:30]=[CH:29]1>>[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[N:23]3[C:18]([CH:19]=[N:20][C:21]([NH:37][C:34]4[CH:35]=[CH:36][C:31]5[N:30]=[CH:29][N:28]([CH3:27])[C:32]=5[CH:33]=4)=[N:22]3)=[CH:17][CH:16]=2)[CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

3

Edukt 2

HCID 136802831-Methyl-1H-benzimidazol-6-amineHCID 66711063HCID 66711063, Verbindung

Produkt 1

HCID 66711227N-tert-Butyl-3-[2-(3-methyl-3H-benzimidazol-5-ylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-benzenesulfonamide

Versuchsvorschrift

Following the synthetic and purification procedures described in Example 1293d, N-tert-butyl-3-(2-methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-benzenesulfonamide (103 mg, 0.262 mmol) was coupled with 3-methyl-3H-benzimidazol-5-ylamine (66 mg, 0.45 mmol) at 105° C. for 120 h to afford the title compound. Yield of TFA salt: 78 mg (50%) of brown powder; LC/MS: 476 (M+H); HPLC: 97% pure, RT=2.64 min; 1H NMR: (DMSO, δ) 10.04 (s, 1H), 9.38 (s, 1H), 9.12 (s, 1H), 8.49 (s, 1H), 8.41 (d, J=8.0, 1H), 8.31 (s, 1H), 7.87 (d, J=8.0, 1H), 7.79 (m, 3H), 7.61 (s, 1H), 7.24 (d, J=4.9, 1H), 7.07 (d, J=4.9, 1H), 3.81 (s, 3H), 1.08 (s, 9H).

Aufarbeitung

  1. custompurification procedures

Quellen und Nachweise

ORD-Eintrag
ord-31d9118a815340759b20d02484880c61
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08471005B2

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