Tetrafluoro-m-phenylenediamine dihydrochloride → {6-[7-(6-Methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-1H-benzoimidazol-2-yl}-methanol

HRID 1262230Notes

Reaction equation

HRID 1262230 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[N:17]3[C:12]([CH:13]=[N:14][C:15](OS(C(F)(F)F)(=O)=O)=[N:16]3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[NH2:26][C:27]1[CH:28]=[CH:29][C:30]2[N:34]=[C:33]([CH2:35][OH:36])[NH:32][C:31]=2[CH:37]=1.C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[N:17]3[C:12]([CH:13]=[N:14][C:15]([NH:26][C:27]4[CH:28]=[CH:29][C:30]5[N:34]=[C:33]([CH2:35][OH:36])[NH:32][C:31]=5[CH:37]=4)=[N:16]3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 838521(5-Amino-1H-benzo[d]imidazol-2-yl)methanolHCID 86661684Trifluoro-methanesulfonic acid 7-(6-methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl ester

Product 1

HCID 66712662{6-[7-(6-Methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-1H-benzoimidazol-2-yl}-methanol

Procedure

{6-[7-(6-Methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-1H-benzoimidazol-2-yl}-methanol was prepared from trifluoro-methanesulfonic acid 7-(6-methoxy-pyridin-3-yl)-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 (35 mg, 34%). m.p.=182-187° C.; LCMS (m/e) 388 (M+H); 1H-NMR (d6-DMSO, 400 MHz) δ 12.16 (bs, 1H), 9.36 (s, 1H), 8.97 (s, 1H), 8.92 (s, 1H), 8.60 (dd, 1H, J=1.8 and 8.7 Hz), 7.87 (bs, 1H), 7.50-7.35 (m, 2H), 7.18 (d, 1H, J=4.6 Hz), 6.99 (d, 1H, J=8.7 Hz), 6.94 (d, 1H, J=4.6 Hz), 5.63 (bs, 1H), 4.66 (s, 2H), 3.93 (s, 3H).

Sources & evidence

ORD record
ord-848c66f671de430c859d47b2609137cb
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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