Hydrochloric Acid → ethyl 4-amino-5-[4-(1H-benzimidazol-2-ylamino)phenyl]pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate

HRID 2197535Notes

Reaction equation

HRID 2197535 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8]([C:16]3[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=3)[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1.Cl[C:24]1[NH:25][C:26]2[CH:32]=[CH:31][CH:30]=[CH:29][C:27]=2[N:28]=1.Cl>C(O)CCC.CN(C=O)C.O1CCOCC1>[NH2:1][C:2]1[C:7]2=[C:8]([C:16]3[CH:17]=[CH:18][C:19]([NH:22][C:24]4[NH:28][C:27]5[CH:29]=[CH:30][CH:31]=[CH:32][C:26]=5[N:25]=4)=[CH:20][CH:21]=3)[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 785722-ChlorobenzimidazoleHCID 57758198Ethyl 4-amino-5-(4-aminophenyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate

Product 1

HCID 16223286ethyl 4-amino-5-[4-(1H-benzimidazol-2-ylamino)phenyl]pyrrolo[2,1-f][1,2,4]triazine-6-carboxylateYield 20.2%

Reagents, catalysts & solvents 3

HCID 2631-ButanolSolventHCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of ethyl 4-amino-5-(4-aminophenyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate (50.0 mg, 0.17 mmol) and 2-chlorobenzimidazole (30.2 mg, 0.17 mmol) in n-butanol (5 mL) and DMF (1 mL) were heated (90° C.) overnight in the presence of a trace amount of 4 M hydrogen chloride in dioxane. After cooling, the solution was concentrated under reduced pressure and the residue was purified by HPLC to afford the desired product (14.2 mg, 19%). 1H-NMR (300 MHz, DMSO-d6) 8.09 (s, 1H), 8.05 (br s, 1H), 7.89 (s, 1H), 7.79-7.85 (m, 2H), 7.24-7.34 (m, 4H), 6.89-6.99 (m, 2H), 5.14 (br, s, 1H), 4.06 (q, J=7.1 Hz, 2H), 1.09 (t, J=7.1 Hz, 3H); ES-MS m/z 414.3 (MH)+; HPLC RT (Method A) 2.57 min.

Workup

  1. temperatureAfter cooling
  2. concentrationthe solution was concentrated under reduced pressure
  3. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-660bf3b3da3749bca54d08b8623b0431
Source dataset
uspto-grants-2012_12
Patent number
US08338594B2

Reaction notes

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