5-Aminobenzimidazole → HCID 66712588, compound

HRID 1262368Notes

Reaction equation

HRID 1262368 reaction equation
CS([C:4]1[N:9]=[CH:8][C:7]2=[CH:10][CH:11]=[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][CH3:20])[N:6]2[N:5]=1)=O.[N:21]1[C:25]2[CH:26]=[CH:27][C:28]([NH2:30])=[CH:29][C:24]=2[NH:23][CH:22]=1>>[N:21]1[C:25]2[CH:26]=[CH:27][C:28]([NH:30][C:4]3[N:9]=[CH:8][C:7]4=[CH:10][CH:11]=[C:12]([C:13]5[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=5[O:19][CH3:20])[N:6]4[N:5]=3)=[CH:29][C:24]=2[NH:23][CH:22]=1

Participants

3

Reactant 2

HCID 136235-AminobenzimidazoleHCID 667107912-Methanesulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 66712588HCID 66712588, compound

Procedure

Following the synthetic and purification procedures described in Example 1293d, 2-methanesulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine (75.4 mg, 0.262 mmol) was coupled to 3H-benzimidazol-5-ylamine (60.0 mg, 0.45 mmol) at 105° C. for 86 h to afford the title compound. Yield of TFA salt: 62 mg (50%) of brown powder. LC/MS: 357 (M+H); HPLC: 95% pure, RT=2.38 min; 1H NMR: (DMSO, δ) 9.77 (s, 1H), 9.38 (s, 1H), 9.02 (s, 1H), 8.04 (s, 1H), 7.93 (d, J=9.2, 1H), 7.85 (d, J=7.5, 1H), 7.65 (d, J=9.2, 1H), 7.47 (t, J=8.2, 1H), 7.25 (d, J=8.2, 1H), 7.17 (t, J=7.5, 1H), 7.01 (d, J=4.8, 1H), 6.98 (d, J=4.8, 1H), 3.81 (s, 3H)-benzimidazole NH presumably underwent rapid exchange with residual water.

Workup

  1. custompurification procedures

Sources & evidence

ORD record
ord-458e296ea3134f798c22d61ce2cfdfd1
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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