Trifluoroacetic acid → Trifluoroacetic acid

HRID 1157413Notes

Reaction equation

HRID 1157413 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[CH:16]=[C:15]([O:17][CH2:18][C:19]3[C:27]4[C:22](=[N:23][C:24]([NH:28]CC5C=CC(OC)=CC=5)=[CH:25][CH:26]=4)[NH:21][N:20]=3)[CH:14]=[CH:13][C:12]=2[Cl:38])[CH:9]=1)[C:5]#[N:6].[C:39]([OH:45])([C:41]([F:44])([F:43])[F:42])=[O:40]>>[NH2:28][C:24]1[N:23]=[C:22]2[NH:21][N:20]=[C:19]([CH2:18][O:17][C:15]3[CH:14]=[CH:13][C:12]([Cl:38])=[C:11]([CH:16]=3)[O:10][C:8]3[CH:7]=[C:4]([CH:3]=[C:2]([Cl:1])[CH:9]=3)[C:5]#[N:6])[C:27]2=[CH:26][CH:25]=1.[C:39]([OH:45])([C:41]([F:44])([F:43])[F:42])=[O:40]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178490932HCID 178490932, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 178509958HCID 178509958, compound

Conditions

Temperature
60 °C

Procedure

3-chloro-5-[2-chloro-5-({6-[(4-methoxybenzyl)amino]-1H-pyrazolo[3,4-b]pyridin-3-yl}methoxy)phenoxy]benzonitrile (37-8) was dissolved in 6 mL of TFA and heated to 60° C. for 7 hours until reaction was complete as determined by LC/MS analysis. After removal of all volatile material the crude residue was purified via prep HPLC (20%-70% acetonitrile in H2O: C18 Phenomenex Gemini) and lyophilzed from dioxane to yield the title compound in the form of a TFA salt. H1 NMR (CD3OD): 5.40 (s 2H), 6.58 (d, 1H), 6.96 (d, 1H), 7.04 (d, 1H), 7.16 (s, 1H), 7.18 (s, 1H), 7.58 (d, 1H), 7.52 (s, 1H), 8.10 (bs, 1H).

Workup

  1. customAfter removal of all volatile material the crude residue
  2. customwas purified via prep HPLC (20%-70% acetonitrile in H2O: C18 Phenomenex Gemini)

Sources & evidence

ORD record
ord-43d984bd8fa543158c2e68799370c7ae
Source dataset
uspto-grants-2010_10
Patent number
US07807684B2

Reaction notes

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