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Citric Acid → (4-aminopyridin-2-yl)[1-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-1H-pyrrolo[3,2-c]pyridin-3-yl]methanone

HRID 1753039
Notes
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Reaction equation

HRID 1753039 reaction equation
[Si:1]([O:8][CH2:9][C:10]([N:13]1[C:21]2[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2[C:15]([C:22]([C:24]2[CH:29]=[C:28]([N:30]=C(C3C=CC=CC=3)C3C=CC=CC=3)[CH:27]=[CH:26][N:25]=2)=[O:23])=[CH:14]1)([CH3:12])[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[NH2:30][C:28]1[CH:27]=[CH:26][N:25]=[C:24]([C:22]([C:15]2[C:16]3[CH:17]=[N:18][CH:19]=[CH:20][C:21]=3[N:13]([C:10]([CH3:12])([CH3:11])[CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3])[CH:14]=2)=[O:23])[CH:29]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 311Citric AcidHCID 11430Potassium CarbonateHCID 90093197[1-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-1H-pyrrolo[3,2-c]pyridin-3-yl]{4-[(diphenylmethylene)amino]pyridin-2-yl}methanone

Product 1

HCID 90093653(4-aminopyridin-2-yl)[1-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-1H-pyrrolo[3,2-c]pyridin-3-yl]methanoneYield 70.3%

Reagents, catalysts & solvents

1
HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [1-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-1H-pyrrolo[3,2-c]pyridin-3-yl]{4-[(diphenylmethylene)amino]pyridin-2-yl}methanone (Preparation 35, 1.4 g, 2.38 mmol) in THF (3 mL) was added a 1M solution of citric acid (2.5 g, 11.9 mmol) and the reaction was stirred at room temperature for 4 hours. A 10% aqueous solution of potassium carbonate was added carefully, and the mixture extracted into EtOAc (3×50 mL). The organic layers were combined, dried over MgSO4 and concentrated in vacuo. To the residue was added DCM and a solid precipitated that was filtered and dried. The mother liquors were purified using silica gel column chromatography eluting with 100% heptanes to 100% EtOAc to 5% MeOH in EtOAc to afford further material. The solids were combined to afford the title compound (70%, 710 mg).

Workup

  1. extractionthe mixture extracted into EtOAc (3×50 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. additionTo the residue was added DCM
  5. customa solid precipitated that
  6. filtrationwas filtered
  7. customdried
  8. customThe mother liquors were purified
  9. washeluting with 100% heptanes to 100% EtOAc to 5% MeOH in EtOAc
  10. customto afford further material

Sources & evidence

ORD record
ord-f70afb55b33843668ea2fa7d904a9314
Source dataset
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09163021B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes