HCID 11179187, compound → HCID 11430644, compound

HRID 2374951Notes

Reaction equation

HRID 2374951 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][NH:11]C(=O)C)=[CH:5][C:4]=1[NH:15][C:16]1[N:21]=[CH:20][C:19]2=[C:22]([CH3:35])[N:23]=[C:24]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=3)[N:18]2[N:17]=1>Cl>[NH2:11][CH2:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([NH:15][C:16]2[N:21]=[CH:20][C:19]3=[C:22]([CH3:35])[N:23]=[C:24]([C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=4)[N:18]3[N:17]=2)[CH:5]=1

Participants

3

Reactant 1

HCID 11179187HCID 11179187, compound

Product 1

HCID 11430644HCID 11430644, compoundYield 17.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of N-{2-[4-methoxy-3-({5-methyl-7-[3-(trifluoromethyl)phenyl]-imidazo[5,1-f][1,2,4]triazin-2-yl}amino)phenyl]ethyl}acetamide (Example 52) (0.050 g, 0.17 mmol) in dilute HCl(aq) (1N, 15 mL) was heated to reflux for 5 h. Neutralization with NaOH(aq) (1N) and extraction into EtOAc followed by concentration and preparative HPLC gave N-[5-(2-aminoethyl)-2-methoxyphenyl]-5-methyl-7-[3-(trifluoromethyl)-phenyl]imidazo[5,1-f][1,2,4]triazin-2-amine (0.013 g) as a yellow solid. 1H NMR (Acetone-d6): δ9.17 (s, 1H), 9.08 (d, J=8.1 Hz, 1H), 8.64 (s, 1H), 8.33-8.30 (m, 1H), 8.13 (s, 1H), 7.97-7.90 (m, 1H), 7.80-7.77 (m, 1H), 7.02-6.95 (m, 2H), 3.96 (s, 3H), 3.48 (t, J=7.4 Hz, 2H), 2.95 (t, J=7.4 Hz, 2H), 2.60 (s, 3H). MS m/z 443 (M+1).

Workup

  1. temperatureto reflux for 5 h
  2. extractionNeutralization with NaOH(aq) (1N) and extraction into EtOAc
  3. concentrationfollowed by concentration and preparative HPLC

Sources & evidence

ORD record
ord-82dab7042401489cb1b0aa97cafb3ccb
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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