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Trifluoroacetic acid → [5-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-1-(4-methoxy-benzyl)-1H-pyrazol-3-yl]-(4-fluoro-benzyl)-amine

HRID 509996
Notes
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Reaction equation

HRID 509996 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([CH:11]([C:13]3[N:14]([CH2:27][C:28]4[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=4)[N:15]=[C:16]([NH:18][CH2:19][C:20]4[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=4)[CH:17]=3)O)=[CH:9][N:8]([Si](C(C)C)(C(C)C)C(C)C)[C:5]2=[N:6][CH:7]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([CH2:11][C:13]3[N:14]([CH2:27][C:28]4[CH:29]=[CH:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=4)[N:15]=[C:16]([NH:18][CH2:19][C:20]4[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=4)[CH:17]=3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 58259145(5-chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-[5-(4-fluoro-benzylamino)-2-(4-methoxy-benzyl)-2H-pyrazol-3-yl]-methanol

Product 1

HCID 58259346[5-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-1-(4-methoxy-benzyl)-1H-pyrazol-3-yl]-(4-fluoro-benzyl)-amine

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

In a quartz vial, (5-chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-[5-(4-fluoro-benzylamino)-2-(4-methoxy-benzyl)-2H-pyrazol-3-yl]-methanol (148, 0.328 g, 0.506 mmol) was combined with 20 mL of dichloromethane, triethylsilane (0.4 mL, 2.0 mmol) was added, followed by trifluoroacetic acid (0.2 mL, 2.0 mmol). The reaction was stirred overnight at room temperature, then concentrated under vacuum and ethyl acetate was added. This was washed with 1 M aqueous potassium carbonate and brine, dried with sodium sulfate, and purified by silica gel column chromatography, eluting with 2-20% methanol in dichloromethane. Appropriate fractions were combined and concentrated under vacuum, and the solid further washed with ethyl acetate and hexane to provide the desired compound. 1H NMR was consistent with compound structure.

Workup

  1. additionwas added
  2. concentrationconcentrated under vacuum and ethyl acetate
  3. additionwas added
  4. washThis was washed with 1 M aqueous potassium carbonate and brine
  5. dry with materialdried with sodium sulfate
  6. custompurified by silica gel column chromatography
  7. washeluting with 2-20% methanol in dichloromethane
  8. concentrationconcentrated under vacuum
  9. washthe solid further washed with ethyl acetate and hexane

Sources & evidence

ORD record
ord-8e913f4e8b5e4a5cb2e6bd0807df7cc2
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09096593B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes