1-methyl-1H-indazol-6-amine → [7-(3-Cyclopropylmethanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-(1-methyl-1H-indazol-6-yl)-amine

HRID 1262378

Reaktionsgleichung

Reaktionsgleichung von HRID 1262378
[CH:1]1([CH2:4][S:5]([C:8]2[CH:9]=[C:10]([C:14]3[N:22]4[C:17]([CH:18]=[N:19][C:20](SC)=[N:21]4)=[CH:16][CH:15]=3)[CH:11]=[CH:12][CH:13]=2)(=[O:7])=[O:6])[CH2:3][CH2:2]1.[CH3:25][N:26]1[C:34]2[C:29](=[CH:30][CH:31]=[C:32]([NH2:35])[CH:33]=2)[CH:28]=[N:27]1>>[CH:1]1([CH2:4][S:5]([C:8]2[CH:9]=[C:10]([C:14]3[N:22]4[C:17]([CH:18]=[N:19][C:20]([NH:35][C:32]5[CH:33]=[C:34]6[C:29]([CH:28]=[N:27][N:26]6[CH3:25])=[CH:30][CH:31]=5)=[N:21]4)=[CH:16][CH:15]=3)[CH:11]=[CH:12][CH:13]=2)(=[O:7])=[O:6])[CH2:3][CH2:2]1

Komponenten

3

Edukt 2

HCID 8404331-methyl-1H-indazol-6-amineHCID 667121477-(3-Cyclopropylmethanesulfonyl-phenyl)-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine

Produkt 1

HCID 66711379[7-(3-Cyclopropylmethanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-(1-methyl-1H-indazol-6-yl)-amine

Versuchsvorschrift

Following the synthetic and purification procedures described in Example 1293d, 7-(3-cyclopropylmethanesulfonyl-phenyl)-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine (75 mg, 0.20 mmol) was coupled with 1-methyl-1H-indazol-6-ylamine (50.0 mg, 0.340 mmol) at 105° C. for 168 h to afford the titled compound. Yield of TFA salt: 11 mg (10%) of brown powder; LC/MS: 459 (M+H); HPLC: 97% pure, RT=3.29 min; 1H NMR: (DMSO, δ) 9.74 (s, 1H), 9.10 (s, 1H), 8.58 (d, J=7.7, 1H), 8.32 (s, 1H), 8.00 (s, 1H), 7.84 (d, J=7.9, 1H), 7.82 (s, 1H), 7.78 (t, J=7.9, 1H), 7.56 (d, J=8.7, 1H), 7.23 (d, J=8.7, 1H), 7.20 (d, J=4.9, 1H), 6.95 (d, J=4.9, 1H), 3.69 (s, 3H), 3.22 (d, J=7.3, 2H), 0.78 (m, 1H), 0.33 (m, 2H), −0.01 (m, 2H).

Aufarbeitung

  1. custompurification procedures

Quellen und Nachweise

ORD-Eintrag
ord-4ca5feaf21e74b54b4cd119a56413bb6
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08471005B2

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