5-Amino-2-hydroxybenzimidazole → N-tert-Butyl-3-[2-(2-oxo-2,3-dihydro-1H-benzimidazol-5-ylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-benzenesulfonamide

HRID 1262361Notes

Reaction equation

HRID 1262361 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].[NH2:27][C:28]1[CH:37]=[CH:36][C:31]2[NH:32][C:33](=[O:35])[NH:34][C:30]=2[CH:29]=1>>[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]([NH:27][C:28]4[CH:37]=[CH:36][C:31]5[NH:32][C:33](=[O:35])[NH:34][C:30]=5[CH:29]=4)=[N:22]3)=[CH:17][CH:16]=2)[CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 667655-Amino-2-hydroxybenzimidazoleHCID 66711063N-tert-Butyl-3-(2-methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-benzenesulfonamide

Product 1

HCID 66712018N-tert-Butyl-3-[2-(2-oxo-2,3-dihydro-1H-benzimidazol-5-ylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-benzenesulfonamide

Procedure

Following the synthetic and purification procedures described in Example 1293d, a 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 5-amino-1,3-dihydro-benzimidazol-2-one (67 mg, 0.45 mmol) at 105° C. for 72 h to afford the title compound. Yield of TFA salt: 82 mg (52%) of brown powder; LC/MS: 478 (M+H); HPLC: 97% pure, RT=2.83 min; 1H NMR: (DMSO, δ) 10.46 (s, 1H), 10.42 (s, 1H), 9.34 (s, 1H), 9.00 (s, 1H), 8.52 (s, 1H), 8.44 (d, J=8.0, 1H), 7.84 (d, J=8.3, 1H), 7.73 (appt, J=8.0, 1H), 7.63 (s, 1H), 7.47 (dd, J=8.1, 1.8, 1H), 7.23 (s, 1H), 7.19 (d, J=5.0, 1H), 6.98 (d, J=3.6, 1H), 6.93 (d, J=8.3, 1H), 1.11 (s, 9H).

Workup

  1. custompurification procedures

Sources & evidence

ORD record
ord-2b6f6a4c3f3049c6938ba7e724828ceb
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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