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Potassium Carbonate → ((S)-4-Bromo-9-cyclopropylmethyl-8-oxo-3,6,7,8,9,10-hexahydro-2,3,9-triaza-cyclohept[e]inden-7-yl)-acetic acid methyl ester

HRID 132232
Notes
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Reaction equation

HRID 132232 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:13][C@@H:14]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[C:15]([O:17]C)=O)[C:5]([CH2:11]Cl)=[C:6]2[C:10]=1[NH:9][N:8]=[CH:7]2.C(=O)([O-])[O-].[K+].[K+].[NH2:30][CH2:31][CH:32]1[CH2:34][CH2:33]1>C(#N)C>[CH3:23][O:22][C:20](=[O:21])[CH2:19][C@H:14]1[C:15](=[O:17])[N:30]([CH2:31][CH:32]2[CH2:34][CH2:33]2)[CH2:11][C:5]2[C:6]3[CH:7]=[N:8][NH:9][C:10]=3[C:2]([Br:1])=[CH:3][C:4]=2[CH2:13]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 75646CyclopropanemethanamineHCID 59732029(S)-dimethyl 2-((7-bromo-4-(chloromethyl)-1H-indazol-5-yl)methyl)succinate

Product 1

HCID 59731925((S)-4-Bromo-9-cyclopropylmethyl-8-oxo-3,6,7,8,9,10-hexahydro-2,3,9-triaza-cyclohept[e]inden-7-yl)-acetic acid methyl esterYield 64%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Procedure

(S)-dimethyl 2-((7-bromo-4-(chloromethyl)-1H-indazol-5-yl)methyl)succinate (630 mg, 1.6 mmol) was dissolved in acetonitrile (5 mL). Potassium carbonate (560 mg, 4.1 mmol) was added to the mixture followed by (aminomethyl)cyclopropane (700 μL, 8.1 mmol). Mixture was heated to reflux and held with stirring for 1.5 hours. Mixture was cooled to room temperature. Mixture was filtered. Filtrate was concentrated by roto-vap. Residue was dissolved in a mixture of toluene (10 mL) and acetic acid (1 mL). Mixture was heated to reflux and held with stirring for 18 hours. Mixture was concentrated by roto-vap. Silica gel chromatography (ethyl acetate-hexanes) afforded the title compound as tan solid in 64% yield. MS m/e (M+H)+=406.0, 408.0.

Workup

  1. temperatureMixture was heated
  2. temperatureto reflux
  3. filtrationMixture was filtered
  4. concentrationFiltrate was concentrated by roto-vap
  5. dissolutionResidue was dissolved in a mixture of toluene (10 mL) and acetic acid (1 mL)
  6. temperatureMixture was heated
  7. temperatureto reflux
  8. stirringwith stirring for 18 hours
  9. concentrationMixture was concentrated by roto-vap

Sources & evidence

ORD record
ord-1017319e35cd48cf95b0e377efda8c67
Source dataset
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07384930B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes