HCID 86624473, compound → HCID 178509923, compound

HRID 505534Notes

Reaction equation

HRID 505534 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:8][C:9]([F:14])([F:13])[C:10]([OH:12])=[O:11].[Cl:15][C:16]1[CH:17]=[C:18]([CH:21]=[C:22]([O:24][C:25]2[C:33]3[N:32]=[CH:31][N:30]([CH2:34][C:35]4[C:43]5[C:38](=[N:39][C:40]([NH:44]CC6C=CC(OC)=CC=6)=[CH:41][CH:42]=5)[N:37](CC5C=CC(OC)=CC=5)[N:36]=4)[C:29]=3[CH:28]=[CH:27][C:26]=2[Cl:63])[CH:23]=1)[C:19]#[N:20]>FC(F)(F)C(O)=O>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:8][C:9]([F:14])([F:13])[C:10]([OH:12])=[O:11].[NH2:44][C:40]1[N:39]=[C:38]2[NH:37][N:36]=[C:35]([CH2:34][N:30]3[C:29]4[CH:28]=[CH:27][C:26]([Cl:63])=[C:25]([O:24][C:22]5[CH:21]=[C:18]([CH:17]=[C:16]([Cl:15])[CH:23]=5)[C:19]#[N:20])[C:33]=4[N:32]=[CH:31]3)[C:43]2=[CH:42][CH:41]=1

Participants

3

Reactant 1

HCID 86624473HCID 86624473, compound

Product 1

HCID 178509923HCID 178509923, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 3-chloro-5-{[5-chloro-1-({1-(4-methoxybenzyl)-6-[(4-methoxybenzyl)amino]-1H-pyrazolo[3,4-b]pyridin-3-yl}methyl)-1H-benzimidazol-4-yl]oxy}benzonitrile bis(trifluoroacetate) (39 mg, 0.042 mmol) in trifluoroacetic acid (2 mL) was heated to 70° C. for 4 hours. After this time, the solvent was removed in vacuo and the residue was purified on a Luna column (10μ, C18, 250×21.2 cm) eluting with 5-95% ACN/water with 0.1% TFA) to give the desired compound.

Workup

  1. customAfter this time, the solvent was removed in vacuo
  2. customthe residue was purified on a Luna column (10μ, C18, 250×21.2 cm)
  3. washeluting with 5-95% ACN/water with 0.1% TFA)

Sources & evidence

ORD record
ord-e810b3adbd3d43058714611544fe9bbd
Source dataset
uspto-grants-2010_08
Patent number
US07781454B2

Reaction notes

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