5-Amino-2-hydroxybenzimidazole → HCID 46851203, compound

HRID 1262366Notes

Reaction equation

HRID 1262366 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][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=3)[N:6]2[N:5]=1)=O.[NH2:23][C:24]1[CH:33]=[CH:32][C:27]2[NH:28][C:29](=[O:31])[NH:30][C:26]=2[CH:25]=1>>[CH3:22][S:19]([C:16]1[CH:17]=[CH:18][C:13]([C:12]2[N:6]3[C:7]([CH:8]=[N:9][C:4]([NH:23][C:24]4[CH:33]=[CH:32][C:27]5[NH:28][C:29](=[O:31])[NH:30][C:26]=5[CH:25]=4)=[N:5]3)=[CH:10][CH:11]=2)=[CH:14][CH:15]=1)(=[O:21])=[O:20]

Participants

3

Reactant 2

HCID 667655-Amino-2-hydroxybenzimidazoleHCID 667110462-(Methylsulfinyl)-7-(4-(methylsulfonyl)phenyl)pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 46851203HCID 46851203, compound

Procedure

Following the synthetic and purification procedures described in Example 1293d, 2-methanesulfinyl-7-(4-methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazine (75 mg, 0.22 mmol) was coupled with 5-amino-1,3-dihydro-benzimidazol-2-one (57 mg, 0.38 mmol) at 105° C. for 86 h to afford the title compound. Yield of TFA salt: 79 mg (67%) of brown powder. LC/MS: 421 (M+H); HPLC: 97% pure, RT=2.32 min; 1H NMR: (DMSO, δ) 10.65 (s, 1H), 10.48 (s, 1H), 9.38 (s, 1H), 9.02 (s, 1H), 8.49 (d, J=8.6, 2H), 8.04 (d, J=8.6, 2H), 7.35 (m, 2H), 7.29 (s, 1H), 6.98 (d, J=4.8, 1H), 6.91 (d, J=8.6, 1H), 3.27 (s, 3H).

Workup

  1. custompurification procedures

Sources & evidence

ORD record
ord-6a2f9ea898c24240953914737f959c6a
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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