5-Aminobenzimidazole → HCID 131730669, compound

HRID 1262223Notes

Reaction equation

[C:1]([SiH2:5][O:6][C:7]([CH3:25])([CH3:24])[C:8]1[CH:9]=[C:10]([C:14]2[N:22]3[C:17]([CH:18]=[N:19][C:20](O)=[N:21]3)=[CH:16][CH:15]=2)[CH:11]=[CH:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].[N:26]1[C:30]2[CH:31]=[CH:32][C:33]([NH2:35])=[CH:34][C:29]=2[NH:28][CH:27]=1>>[N:26]1[C:30]2[CH:31]=[CH:32][C:33]([NH:35][C:20]3[N:19]=[CH:18][C:17]4=[CH:16][CH:15]=[C:14]([C:10]5[CH:11]=[CH:12][CH:13]=[C:8]([C:7]([CH3:25])([CH3:24])[O:6][SiH2:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH:9]=5)[N:22]4[N:21]=3)=[CH:34][C:29]=2[NH:28][CH:27]=1

Participants

Reactant 2

HCID 136235-Aminobenzimidazole

HCID 178455422HCID 178455422, compound

Product 1

HCID 131730669HCID 131730669, compound

Procedure

(3H-Benzoimidazol-5-yl)-{7-[3-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-pyrrolo[2,1-f][1,2,4]triazin-2-yl}-amine was prepared from 7-[3-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-pyrrolo[2,1-f][1,2,4]triazin-2-ol and 3H-benzimidazol-5-ylamine in an analogous manner to Example 1052a. Product isolated as an orange solid (129 mg, 81%). m.p.=70-75° C.; LCMS (m/e) 471 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 11.20-10.10 (m, 1H), 8.73 (s, 1H), 8.67-8.39 (m, 2H), 7.97 (s, 1H), 7.86-7.62 (m, 2H), 7.51-7.42 (m, 1H), 7.32 (d, 1H, J=7.5 Hz), 7.09-6.92 (m, 3H), 6.86 (d, 1H, J=4.7 Hz), 4.97 (s, 2H), 0.96 (s, 9H), 0.16 (s, 6H).

Sources & evidence

ORD record: ord-3f8c7d9815674e40b8bc94089cae7be6
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08471005B2

Reaction notes

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