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

HRID 1262231Notes

Reaction equation

HRID 1262231 reaction equation
[N:1]1([S:6]([C:9]2[CH:10]=[C:11]([C:15]3[N:23]4[C:18]([CH:19]=[N:20][C:21](O)=[N:22]4)=[CH:17][CH:16]=3)[CH:12]=[CH:13][CH:14]=2)(=[O:8])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:25][C:26]1[CH:27]=[CH:28][C:29]2[N:33]=[C:32]([CH2:34][OH:35])[NH:31][C:30]=2[CH:36]=1.C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>>[N:1]1([S:6]([C:9]2[CH:10]=[C:11]([C:15]3[N:23]4[C:18]([CH:19]=[N:20][C:21]([NH:25][C:26]5[CH:27]=[CH:28][C:29]6[N:33]=[C:32]([CH2:34][OH:35])[NH:31][C:30]=6[CH:36]=5)=[N:22]4)=[CH:17][CH:16]=3)[CH:12]=[CH:13][CH:14]=2)(=[O:7])=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 3

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 838521(5-Amino-1H-benzo[d]imidazol-2-yl)methanolHCID 1785273247-[3-(Pyrrolidine-1-sulfonyl)-phenyl]-pyrrolo[2,1-f][1,2,4]triazin-2-ol

Product 1

HCID 66712657(6-{7-[3-(Pyrrolidine-1-sulfonyl)-phenyl]-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino}-1H-benzoimidazol-2-yl)-methanol

Procedure

(6-{7-[3-(Pyrrolidine-1-sulfonyl)-phenyl]-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino}-1H-benzoimidazol-2-yl)-methanol was prepared from 7-[3-(pyrrolidine-1-sulfonyl)-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 foam (57 mg, 40%). LCMS (m/e) 490 (M+H); 1H-NMR (d6-DMSO, 400 MHz) δ 12.23-12.01 (m, 1H), 9.47-9.35 (m, 1H), 9.05-8.99 (m, 1H), 8.77-8.61 (m, 1H), 8.35-8.26 (m, 1H), 7.91-7.70 (m, 3H), 7.62-7.37 (m, 2H), 7.32-7.24 (m, 1H), 7.01-6.94 (m, 1H), 5.67-5.58 (m, 1H), 4.70-4.62 (m, 2H), 3.22-3.12 (m, 4H), 1.69-1.60 (m, 4H).

Sources & evidence

ORD record
ord-9133aa93bada42cda61ab228af562cbd
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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