Hydrochloric Acid → [7-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-(2-methyl-benzoxazol-5-yl)-amine

HRID 1262089Notes

Reaction equation

HRID 1262089 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](OS(C(F)(F)F)(=O)=O)=[N:16]2)=[CH:11][CH:10]=1.[CH3:26][C:27]1[O:28][C:29]2[CH:35]=[CH:34][C:33]([NH2:36])=[CH:32][C:30]=2[N:31]=1.Cl.C(N(CC)C(C)C)(C)C.COCC(O)C>>[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:36][C:33]3[CH:34]=[CH:35][C:29]4[O:28][C:27]([CH3:26])=[N:31][C:30]=4[CH:32]=3)=[N:16]2)=[CH:11][CH:10]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 79001-Methoxy-2-propanolHCID 81531DiisopropylethylamineHCID 7379202-Methyl-1,3-benzoxazol-5-amineHCID 86661678Trifluoro-methanesulfonic acid 7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl ester

Product 1

HCID 46852670[7-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-(2-methyl-benzoxazol-5-yl)-amine

Procedure

The Title compound was prepared in the following manner: A mixture of Trifluoro-methanesulfonic acid 7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl ester (100 mg, 0.3 mmol), 2-Methyl-benzoxazol-5-ylamine; hydrochloride (100 mg, 0.5 mmol), N,N-Diisopropylethylamine (2 mL, 10 mmol), and 1-Methoxy-2-propanol (0.3 mL, 3 mmol) were heated at 80° C. overnight. The reaction was concentrated, filtered and placed onto the Gilson. The pure fractions were lyophilized to give a yellow solid (30 mg, 20%). LCMS (E/I+) 372 (M+H). NMR 1H (DMSO-d6)-9.5 (s, 1H), 9.0 (s, 1H), 8.2 (s, 1H), 7.78 (d, 1H, J=7.80 Hz), 7.45-7.54 (m, 3H), 7.23 (d, 1H, J=8.26), 7.12 (t, 1H, J=7.51 Hz), 6.92-6.96 (m, 2H), 3.84 (s, 3H), 2.58 (s, 3H).

Workup

  1. concentrationThe reaction was concentrated
  2. filtrationfiltered

Sources & evidence

ORD record
ord-a7916ee23e93444baad1f16ec50c2bd2
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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