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

HRID 1262228Notes

Reaction equation

HRID 1262228 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:17]2[C:12]([CH:13]=[N:14][C:15](O)=[N:16]2)=[CH:11][CH:10]=1.[NH2:19][C:20]1[CH:21]=[CH:22][C:23]2[N:27]=[C:26]([CH2:28][OH:29])[NH:25][C:24]=2[CH:30]=1.C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:17]2[C:12]([CH:13]=[N:14][C:15]([NH:19][C:20]3[CH:21]=[CH:22][C:23]4[N:27]=[C:26]([CH2:28][OH:29])[NH:25][C:24]=4[CH:30]=3)=[N:16]2)=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 838521(5-Amino-1H-benzo[d]imidazol-2-yl)methanolHCID 1784892767-(2-Methoxyphenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ol

Product 1

HCID 66712292{6-[7-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-1H-benzoimidazol-2-yl}-methanol

Procedure

{6-[7-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-1H-benzoimidazol-2-yl}-methanol was prepared from 7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ol and (6-amino-1H-benzoimidazol-2-yl)-methanol; dihydrochloride in an analogous manner to Example 1052a. Product isolated as a yellow solid (55 mg, 46%). m.p.=239-243° C.; LCMS (m/e) 387 (M+H); 1H-NMR (d6-DMSO, 400 MHz) δ 12.05 (bs, 1H), 9.23 (s, 1H), 8.93 (s, 1H), 8.15-7.42 (m, 2H), 7.87 (d, 1H, J=7.2 Hz), 7.50-7.40 (m, 1H), 7.40-7.22 (m, 1H), 7.22 (d, 1H, J=8.3 Hz), 7.19-7.07 (m, 1H), 6.99-6.85 (m, 2H), 5.60 (bs, 1H), 4.64 (s, 2H), 3.83 (s, 3H).

Sources & evidence

ORD record
ord-4869209ecd2b4049aa20d30884ffbc36
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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