5-Aminobenzimidazole → HCID 66712689, compound

HRID 1262362Notes

Reaction equation

HRID 1262362 reaction equation
[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].[N:27]1[C:31]2[CH:32]=[CH:33][C:34]([NH2:36])=[CH:35][C:30]=2[NH:29][CH:28]=1>>[N:27]1[C:31]2[CH:32]=[CH:33][C:34]([NH:36][C:21]3[N:20]=[CH:19][C:18]4=[CH:17][CH:16]=[C:15]([C:11]5[CH:10]=[C:9]([S:6]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])(=[O:8])=[O:7])[CH:14]=[CH:13][CH:12]=5)[N:23]4[N:22]=3)=[CH:35][C:30]=2[NH:29][CH:28]=1

Participants

3

Reactant 2

HCID 136235-AminobenzimidazoleHCID 66711063N-tert-Butyl-3-(2-methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-benzenesulfonamide

Product 1

HCID 66712689HCID 66712689, compound

Procedure

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 3H-benzimidazol-5-ylamine (60 mg, 0.45 mmol) at 105° C. for 120 h to afford the title compound. Yield of TFA salt: 24 mg (16%) of brown powder; LC/MS: 462 (M+H); HPLC: 97% pure, RT=2.65 min; 1H NMR: (DMSO, δ) 9.91 (s, 1H), 9.40 (s, 1H), 9.11 (s, 1H), 8.59 (s, 1H), 8.42 (d, J=8.0, 1H), 8.09 (s, 1H), 8.01 (d, J=8.0, 1H), 7.85 (m, 2H), 7.77 (t, J=7.7, 1H), 7.65 (s, 1H), 7.28 (d, J=4.9, 1H), 7.06 (d, J=4.9, 1H), 1.10 (s, 9H)— benzimidazole NH presumably underwent rapid exchange with residual water.

Workup

  1. custompurification procedures

Sources & evidence

ORD record
ord-22d6c9a1a9984306ac24ae5b2e0334d7
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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