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Triethylamine → 3-{5-[(1S,4S)-2-oxa-5-azabicyclo[2.2.1]hept-5-ylmethyl]-1H-tetrazol-1-yl}-5-(trifluoromethyl)benzonitrile

HRID 517786
Notes
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Reaction equation

HRID 517786 reaction equation
[C@H:1]12[CH2:26][C@H:4]([N:5]([CH2:7][C:8]3[N:12]([C:13]4[CH:14]=[C:15]([CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=4)[C:16]([NH2:18])=O)[N:11]=[N:10][N:9]=3)[CH2:6]1)[CH2:3][O:2]2.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>ClCCl>[C@H:1]12[CH2:26][C@H:4]([N:5]([CH2:7][C:8]3[N:12]([C:13]4[CH:14]=[C:15]([CH:19]=[C:20]([C:22]([F:23])([F:25])[F:24])[CH:21]=4)[C:16]#[N:18])[N:11]=[N:10][N:9]=3)[CH2:6]1)[CH2:3][O:2]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydride2×HCID 66656200HCID 66656200, compound2×

Product 1

HCID 866919003-{5-[(1S,4S)-2-oxa-5-azabicyclo[2.2.1]hept-5-ylmethyl]-1H-tetrazol-1-yl}-5-(trifluoromethyl)benzonitrileYield 37.8%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

To a solution of 3-{5-[(1S,4S)-2-oxa-5-azabicyclo[2.2.1]hept-5-ylmethyl]-1H-tetrazol-1-yl}-5-(trifluoromethyl)benzamide (Intermediate 32, 100 mg, 0.272 mmol) and triethylamine (0.076 ml, 0.543 mmol) in dichloromethane (5 ml) was added trifluoroacetic anhydride (0.038 ml, 0.272 mmol). The reaction was stirred at room temperature for 4 hours before the addition of trifluoroacetic anhydride (0.038 ml, 0.272 mmol). The reaction was stirred at room temperature for a further three hours. The reaction was partitioned between DCM (5 mL) and water (5 mL). The organic layer was collected via a hydrophobic frit and the solvent removed. The residue was purified by silica chromatography (Biotage SP4, eluting a gradient from 20-80% EtOAc in iso-hexane). The compound was further purified by high pH MDAP to yield the title compound as a white solid (36 mg)

Workup

  1. customThe reaction was partitioned between DCM (5 mL) and water (5 mL)
  2. customThe organic layer was collected via a hydrophobic frit
  3. customthe solvent removed
  4. customThe residue was purified by silica chromatography (Biotage SP4
  5. washeluting a gradient from 20-80% EtOAc in iso-hexane)
  6. customThe compound was further purified by high pH

Sources & evidence

ORD record
ord-ee179f7ca84a4347896763ac94b9dc72
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09115132B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes