Ammonium Chloride → HCID 178523059, compound

HRID 529348Notes

Reaction equation

HRID 529348 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([CH2:12][N:13]([CH:20]2[CH2:22][CH:21]2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])[CH2:8][CH2:7]1)#[N:2].[N-:29]=[N+:30]=[N-:31].[Na+].[Cl-].[NH4+]>CN(C)C=O>[NH:29]1[C:1]([CH2:3][CH2:4][CH2:5][N:6]2[CH2:11][CH2:10][CH:9]([CH2:12][N:13]([CH:20]3[CH2:22][CH:21]3[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])[CH2:8][CH2:7]2)=[N:2][N:31]=[N:30]1

Participants

5

Reactant 3

HCID 25517Ammonium Chloride2×HCID 33557Sodium Azide2×HCID 88962056HCID 88962056, compound

Product 1

HCID 178523059HCID 178523059, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of N-((1-(3-cyanopropyl)piperidin-4-yl)methyl)-2,2,2-trifluoro-N-(2-phenylcyclopropyl)acetamide (260 mg, 0.661 mmol), sodium azide (129 mg, 1.982 mmol), ammonium chloride (159 mg, 2.97 mmol) in N,N-dimethylformamide (DMF) (20 mL) was heated to 110° for 16 hours. Added sodium azide (129 mg, 1.982 mmol) and ammonium chloride (159 mg, 2.97 mmol) and heated to 110° for 16 hours. Concentrated and HPLC purification (reverse phase) was performed. A 7 minute gradient was run (10% AcCN/H2O, 0.1% Formic Acid to 50% ACN/H2O, 0.1% Formic Acid). Obtained 36 mg N20984-94-2(oil) [M+H]+=437.3

Workup

  1. temperaturewas heated to 110° for 16 hours
  2. concentrationConcentrated
  3. customHPLC purification (reverse phase)
  4. customA 7 minute gradient
  5. customObtained 36 mg N20984-94-2(oil) [M+H]+=437.3

Sources & evidence

ORD record
ord-1c451c6607b2459792f0126efe7007f8
Source dataset
uspto-grants-2016_05
Patent number
US09346840B2

Reaction notes

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