Tetrafluoro-m-phenylenediamine dihydrochloride → N-{2-[2-(2-Hydroxymethyl-3H-benzoimidazol-5-ylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-phenyl}-N-methyl-methanesulfonamide

HRID 1262232Notes

Reaction equation

HRID 1262232 reaction equation
[CH3:1][S:2]([N:5]([CH3:29])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[N:20]2[C:15]([CH:16]=[N:17][C:18](OS(C(F)(F)F)(=O)=O)=[N:19]2)=[CH:14][CH:13]=1)(=[O:4])=[O:3].[NH2:30][C:31]1[CH:32]=[CH:33][C:34]2[N:38]=[C:37]([CH2:39][OH:40])[NH:36][C:35]=2[CH:41]=1.C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>>[OH:40][CH2:39][C:37]1[NH:36][C:35]2[CH:41]=[C:31]([NH:30][C:18]3[N:17]=[CH:16][C:15]4=[CH:14][CH:13]=[C:12]([C:7]5[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=5[N:5]([CH3:29])[S:2]([CH3:1])(=[O:4])=[O:3])[N:20]4[N:19]=3)[CH:32]=[CH:33][C:34]=2[N:38]=1

Participants

4

Reactant 3

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 838521(5-Amino-1H-benzo[d]imidazol-2-yl)methanolHCID 86661681Trifluoro-methanesulfonic acid 7-[2-(methanesulfonyl-methyl-amino)-phenyl]-pyrrolo[2,1-f][1,2,4]triazin-2-yl ester

Product 1

HCID 66711438N-{2-[2-(2-Hydroxymethyl-3H-benzoimidazol-5-ylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-phenyl}-N-methyl-methanesulfonamide

Procedure

N-{2-[2-(2-Hydroxymethyl-3H-benzoimidazol-5-ylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-phenyl}-N-methyl-methanesulfonamide was prepared from trifluoro-methanesulfonic acid 7-[2-(methanesulfonyl-methyl-amino)-phenyl]-pyrrolo[2,1-f][1,2,4]triazin-2-yl ester and (6-amino-1H-benzoimidazol-2-yl)-methanol; dihydrochloride in an analogous manner to Example 1061. Product isolated as a yellow solid (32 mg, 31%). m.p.=250-256° C.; LCMS (m/e) 464 (M+H); 1H-NMR (d6-DMSO, 400 MHz) δ 12.5-12.01 (m, 1H), 9.28-9.21 (m, 1H), 8.98-8.92 (m, 1H), 8.12-8.00 (m, 1H), 7.94-7.89 (m, 0.5H), 7.68-7.60 (m, 2H), 7.60-7.31 (m, 3H), 7.27-7.21 (m, 0.5H), 7.01-6.95 (m, 1H), 6.95-6.89 (m, 1H), 5.65-5.54 (m, 1H), 4.67-4.60 (m, 2H), 3.09-3.03 (m, 3H), 2.92-2.86 (m, 3H).

Sources & evidence

ORD record
ord-bc97bb41d70b4d2abdf80d718a8ab884
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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