5-Amino-2-hydroxybenzimidazole → 5-[7-(6-Methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-1,3-dihydro-benzimidazol-2-one

HRID 1262371Notes

Reaction equation

HRID 1262371 reaction equation
CS([C:4]1[N:9]=[CH:8][C:7]2=[CH:10][CH:11]=[C:12]([C:13]3[CH:14]=[N:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=3)[N:6]2[N:5]=1)=O.[NH2:21][C:22]1[CH:31]=[CH:30][C:25]2[NH:26][C:27](=[O:29])[NH:28][C:24]=2[CH:23]=1>>[CH3:20][O:19][C:16]1[N:15]=[CH:14][C:13]([C:12]2[N:6]3[C:7]([CH:8]=[N:9][C:4]([NH:21][C:22]4[CH:31]=[CH:30][C:25]5[NH:26][C:27](=[O:29])[NH:28][C:24]=5[CH:23]=4)=[N:5]3)=[CH:10][CH:11]=2)=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 667655-Amino-2-hydroxybenzimidazoleHCID 667108472-Methanesulfinyl-7-(6-methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 667124815-[7-(6-Methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-1,3-dihydro-benzimidazol-2-one

Procedure

Following the synthetic and purification procedures described in Example 1293d, 2-methanesulfinyl-7-(6-methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazine (60 mg, 0.2 mmol) was coupled with 5-amino-1,3-dihydro-benzimidazol-2-one (54 mg, 0.36 mmol) at 105° C. for 86 h to afford the title compound. Yield of TFA salt: 43 mg (44%) of tan powder. LC/MS: 374 (M+H); HPLC: 97% pure, RT=2.20 min; 1H NMR: (DMSO, δ) 10.49 (s, 1H), 10.39 (s, 1H), 9.20 (s, 1H), 8.88 (s, 1H), 8.83 (s, 1H), 8.47 (dd, J=8.4, 2.5, 1H), 7.25 (d, J=8.4, 1H), 7.21 (s, 1H), 7.10 (d, J=4.8, 1H), 6.95 (d, J=8.8, 1H), 6.87 (d, J=4.8, 1H), 6.79 (d, J=8.4, 1H), 3.86 (s, 3H).

Workup

  1. custompurification procedures

Sources & evidence

ORD record
ord-23b985e30ff940108414ded12fc141f5
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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